U.S. patent application number 11/632389 was filed with the patent office on 2008-02-14 for white light emitting organic electroluminescence element, display and illuminator.
Invention is credited to Masato Nishizeki, Tomohiro Oshiyama.
Application Number | 20080038586 11/632389 |
Document ID | / |
Family ID | 35785095 |
Filed Date | 2008-02-14 |
United States Patent
Application |
20080038586 |
Kind Code |
A1 |
Nishizeki; Masato ; et
al. |
February 14, 2008 |
White Light Emitting Organic Electroluminescence Element, Display
and Illuminator
Abstract
A white light emitting organic electroluminescent element
comprising two electrodes having therebetween one or more
constituting layers including a light emission layer, the one or
more constituting layers comprising at least two phosphorescent
compounds, wherein at least one of the phosphorescent compounds is
a green light emitting ortho metalated complex; and a spectral
ratio of the green light emitting ortho metalated complex in ae
emission spectral distribution in a range of 400-800 nm is not less
than 60%.
Inventors: |
Nishizeki; Masato; (Tokyo,
JP) ; Oshiyama; Tomohiro; (Tokyo, JP) |
Correspondence
Address: |
CANTOR COLBURN, LLP
55 GRIFFIN ROAD SOUTH
BLOOMFIELD
CT
06002
US
|
Family ID: |
35785095 |
Appl. No.: |
11/632389 |
Filed: |
July 7, 2005 |
PCT Filed: |
July 7, 2005 |
PCT NO: |
PCT/JP05/12584 |
371 Date: |
January 12, 2007 |
Current U.S.
Class: |
428/704 |
Current CPC
Class: |
H01L 51/008 20130101;
H01L 51/0087 20130101; H01L 51/009 20130101; Y02B 20/181 20130101;
Y02B 20/00 20130101; C09K 2211/1029 20130101; H01L 51/0084
20130101; C09K 2211/1033 20130101; H01L 51/0072 20130101; H01L
51/0067 20130101; H01L 51/0071 20130101; C09K 2211/1022 20130101;
C09K 2211/1074 20130101; C09K 2211/1044 20130101; C09K 2211/185
20130101; H01L 51/5036 20130101; H01L 51/0085 20130101; H05B 33/14
20130101; H01L 51/0062 20130101; H01L 51/0081 20130101; C09K
2211/1092 20130101; C09K 11/06 20130101; H01L 51/5016 20130101;
C09K 2211/1059 20130101; C09K 2211/1096 20130101; C09K 2211/1037
20130101 |
Class at
Publication: |
428/704 |
International
Class: |
B32B 9/04 20060101
B32B009/04 |
Foreign Application Data
Date |
Code |
Application Number |
Jul 16, 2004 |
JP |
2004-210330 |
Claims
1. A white light emitting organic electroluminescent element
comprising two electrodes having therebetween one or more
constituting layers including a light emission layer, the one or
more constituting layers comprising at least two phosphorescent
compounds, wherein at least one of the phosphorescent compounds is
a green light emitting ortho metalated complex; and a spectral
ratio of the green light emitting ortho metalated complex in an
emission spectral distribution in a range of 400-800 nm is not less
than 60%.
2. The white light emitting organic electroluminescent element of
claim 1, wherein at least one of the phosphorescent compounds is a
blue light emitting ortho metalated complex; and a shortest
emission peak wavelength of the blue light emitting ortho metalated
complex is not more than 455 nm.
3. The white light emitting organic electroluminescent element of
claim 1, wherein at least one of the phosphorescent compounds is a
red light emitting ortho metalated complex.
4. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex
has at least one of the substructures represented by Formulas (1)
to (6) or at last one of tautomers of the substructures represented
by Formulas (1) to (6). ##STR413## [wherein, Z11 is an atomic group
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; R.sub.21, R.sub.12 and R.sub.13 each are a
hydrogen atom or a substituent; and M.sub.11 is a metal belonging
to one of Groups 8 to 10 of the periodic table.] ##STR414##
[wherein, Z21 is an atomic group necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring; R.sub.21,
R.sub.22 and R.sub.13 each are a hydrogen atom or a substituent;
and M.sub.21 is a metal belonging to one of Groups 8 to 10 of the
periodic table.] ##STR415## [wherein, Z31 is an atomic group
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; X.sub.31, X.sub.32 and X.sub.33 each are a
carbon atom, --C(R.sub.3)--, a nitrogen atom or --N(R.sub.3)--
(wherein, R.sub.3 is a hydrogen atom or a substituent); C.sub.31 is
a carbon atom; M.sub.31 is a metal belonging to one of Groups 8 to
10 of the periodic table; and a bond between C.sub.31 and N, a bond
between N and X.sub.33, a bond between X.sub.32 and X.sub.33, a
bond between X.sub.31 and X.sub.32, and a bond between C.sub.31 and
X.sub.31 each are a single bond or a double bond.] ##STR416##
[wherein, Z41 is an atomic group necessary to form an aromatic
heterocyclic ring; at least one of X.sub.4 and X.sub.42 is a
nitrogen atom or --N(R.sub.4)-- (wherein, R.sub.4 is a hydrogen
atom or a substituent); M.sub.41 is a metal belonging to one of
Groups 8 to 10 of the periodic table; C.sub.41, C.sub.42 and
C.sub.43 each are a carbon atom; and a bond between C.sub.41 and
C.sub.42, a bond between C.sub.41 and X.sub.42, a bond between
X.sub.41 and X.sub.42, a bond between X.sub.41 and C.sub.43, and a
bond between C.sub.42 and C.sub.43 each are a single bond or a
double bond.] ##STR417## [wherein, Z51 is an atomic group necessary
to form an aromatic hydrocarbon ring or an aromatic heterocyclic
ring; X.sub.51 is an oxygen atom or a sulfur atom; R.sub.51 and
R.sub.52 each are a hydrogen atom or a substituent; and M.sub.51 is
a metal belonging to one of Groups 8 to 10 of the periodic table.]
##STR418## [wherein, Z61 is an atomic group necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring.
X.sub.61, X.sub.62 and X.sub.63 each are a carbon atom,
--C(R.sub.6)--, a nitrogen atom or --N(R.sub.6)-- (wherein, R.sub.6
is a hydrogen atom or a substituent); and M.sub.61 is a metal
belonging to one of Groups 8 to 10 of the periodic table.]
5. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex is
a platinum complex represented by Formula (7). ##STR419## [wherein,
R.sub.1, R.sub.2, R.sub.3, P4, R.sub.5, R.sub.6 and R.sub.7 each
are a hydrogen atom or a substituent, provided that, at least one
of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7
is a substituent; Ra is a substituent; Xa is an oxygen atom or a
sulfur atom; Y.sub.1-L1-Y, is a bidentate ligand; Y, and Y.sub.2
each independently are an oxygen atom, a nitrogen atom, a carbon
atom or a sulfur atom; and L1 is an atomic group necessary to form
a bidentate ligand together with Y.sub.1 and Y.sub.2.]
6. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex is
a metal complex having a substructure represented by Formula (8) or
(9). ##STR420## [wherein, A, B and C each are a hydrogen atom or a
substituent, provided that at least two of A, B and C are
represented by -Xa-(Ra).sub.na (wherein Ra is a substituent, Xa is
an oxygen atom, a sulfur atom or a nitrogen atom, and na is 1 or
2.), which may be the same or different; R.sub.1, R.sub.2, R.sub.3,
R.sub.4 and R.sub.5 each are a hydrogen atom or a substituent; and
M.sub.1 is an element belonging to one Groups 8 to 10 of the
periodic table.] ##STR421## [wherein, Rb, Rc and Rd each are a
substituent; Xb, Xc and Xd each are an oxygen atom, a sulfur atom
or a nitrogen atom; nb, nc and nd each are 1 or 2; R.sub.6,
R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each are a hydrogen atom or
a substituent; and M.sub.2 is an element belonging to one of Groups
8 to 10 of the periodic table.]
7. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex is
a metal complex having a ligand represented by Formula (10), a
metal complex having a substructure represented by Formula (11) or
(12) or a metal complex having a tautomer of the substructure
represented by Formula (11) or (12). ##STR422## [wherein, X.sub.1,
X.sub.2, X.sub.3 and R.sub.4 each independently are a carbon atom
or a nitrogen atom; C.sub.1 and C.sub.2 each are a carbon atom; Z1
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.1, X.sub.1 and X.sub.3; Z2 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.2, X.sub.2 and X.sub.4;
A.sub.1 is a nitrogen atom or a boron atom; R.sub.1 is a
substituent; and a bond between C, and X.sub.1, a bond between
C.sub.2 and X.sub.2, a bond between X.sub.1 and X.sub.3, and a bond
between X.sub.2 and X.sub.4 each are a single bond or a double
bond.] ##STR423## [wherein, C.sub.3, C.sub.4, C.sub.5, C.sub.6 and
C.sub.7 each are a carbon atom; Z3 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with together with C.sub.3, C.sub.4 and
C.sub.5; Z4 represents a group of atoms necessary to form an
aromatic heterocyclic ring together with together with C.sub.6,
C.sub.7 and N; A.sub.2 is a nitrogen atom or a boron atom; R.sub.2
is a substituent; and M.sub.11 is an element belonging to one of
Groups 8 to 10 of the periodic table; and a bond between C.sub.3
and C.sub.4, a bond between C.sub.4 and C.sub.5, a bond between
C.sub.6 and C.sub.7, and a bond between C.sub.7 and N each are a
single bond or a double bond.] ##STR424## [wherein, A.sub.3 is a
nitrogen atom or a boron atom; R.sub.3 is a substituent; R.sub.4
and R.sub.5 each are a substituent; n1 and n2 each are an integer
of 0-3; and M.sub.12 is an element belonging to one of Groups 8 to
10 of the periodic table.]
8. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex is
a metal complex having a ligand represented by Formula (13), a
metal complex having a substructure represented by Formula (14), a
metal complex having a substructure represented by Formula (15) or
a tautomer of the substructure, a metal complex having a ligand
represented by Formula (16), a metal complex having a substructure
represented by Formula (17) or a metal complex having a
substructure represented by Formula (18). ##STR425## [wherein,
X.sub.1, X.sub.2, X.sub.3 and X.sub.4 each independently are a
carbon atom or a nitrogen atom; C.sub.1 and C.sub.2 each are a
carbon atom; Z1 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.1, X.sub.1 and X.sub.3; Z2 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.2, X.sub.2 and X.sub.4;
A.sub.1 is a carbon atom or a silicon atom; R.sub.1 and R.sub.2
each independently are a hydrogen atom or a substituent; and a bond
between C.sub.1 and X.sub.1, a bond between C.sub.2 and X.sub.2, a
bond between X.sub.1 and X.sub.3, and a bond between X.sub.2 and
X.sub.4 each are a single bond or a double bond.] ##STR426##
[wherein, C.sub.3, C.sub.4, C.sub.5, C.sub.6 and X.sub.7 each are a
carbon atom; Z3 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.5, C.sub.3 and C.sub.7; Z4 represents a group of atoms
necessary to form an aromatic heterocyclic ring together with
C.sub.6, C.sub.4 and N; A.sub.2 is a carbon atom or a silicon atom;
R.sub.3 and R.sub.4 each independently are a hydrogen atom or a
substituent. M.sub.11 is an element belonging to one of Groups 8 to
10 of the periodic table; and a bond between C.sub.5 and C.sub.3, a
bond between C.sub.3 and C.sub.7, a bond between C.sub.6 and
C.sub.4, and a bond between C.sub.4 and N each are a single bond or
a double bond.] ##STR427## [wherein, A.sub.3 is a carbon atom or a
silicon atom; R.sub.5 and R.sub.6 each independently are a hydrogen
atom or a substituent; and R.sub.7 and R.sub.8 each independently
are a substituent; n1 and n2 each independently are an integer of
0-3; M.sub.12 is an element belonging to one of Groups 8 to 10 of
the periodic table.] ##STR428## [wherein, X.sub.3, X.sub.4, X.sub.5
and X.sub.6 each independently are a carbon atom or a nitrogen
atom; C.sub.8-C.sub.13 each are a carbon atom; Z5 represents a
group of atoms necessary to form an aromatic hydrocarbon ring or an
aromatic heterocyclic ring together with C.sub.8, X.sub.3 and
X.sub.5; Z6 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.9, X.sub.4 and X.sub.6; Z7 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.10 and C.sub.11; Z8
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.12 and C.sub.13; A.sub.4 is a carbon atom or a silicon atom;
and a bond between X.sub.3 and X.sub.5, a bond between X.sub.4 and
X.sub.6, a bond between C.sub.8 and X.sub.3, and a bond between
C.sub.9 and X.sub.4, a bond between C.sub.10 and C.sub.11 and a
bond between C.sub.12 and C.sub.13 each are a single bond or a
double bond.] ##STR429## [wherein, C.sub.14-C.sub.22 each are a
carbon atom; Z9 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.16, C.sub.14 and C.sub.18; Z11 represents a group of
atoms necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.19 and C.sub.20; Z12
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.21 and C.sub.22; each are an atomic group necessary to form
an aromatic hydrocarbon ring or an aromatic heterocyclic ring; Z10
represents a group of atoms necessary to form an aromatic
heterocyclic ring together with C.sub.17, C.sub.15 and N; A.sub.5
is a carbon atom or a silicon atom; M.sub.21 is an element
belonging to one of Groups 8 to 10 of the periodic table; and a
bond between C.sub.18 and C.sub.14, a bond between C.sub.14 and
C.sub.16, a bond between C.sub.17 and C.sub.15, and a bond between
C.sub.15 and N, a bond between C.sub.19 and C.sub.20, and a bond
between C.sub.21 and C.sub.22 each are a single bond or a double
bond.] ##STR430## [wherein, Z13 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.23 and C.sub.24; Z14
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.25 and C.sub.26; A.sub.5 is a carbon atom or a silicon atom.
R.sub.9 and R.sub.10 each independently are a substituent; n3 and
n4 each is an integer of 0-3; M.sub.22 is an element belonging to
one of Groups 8 to 10 of the periodic table; and a bond between
C.sub.23 and C.sub.24, and a bond between C.sub.25 and C.sub.26
each are a single bond or a double bond.]
9. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex
comprises a platinum complex selected from the group consisting of
Formulas (19)-(27). ##STR431## [wherein, R.sub.1 and R.sub.2 each
are a hydrogen atom or a substituent, provided that at least one of
R.sub.1 and R.sub.2 is the substituent; X.sub.1 and X.sub.2 each
are a carbon atom, a nitrogen atom or a sulfur atom; and Z.sub.1
and Z.sub.2 each are an atomic group necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring; n1 is an integer
of 1 or 2; L1 is a bidentate ligand when n1 is 1; and p1 and q1
each are an integer of 0-4.] ##STR432## [wherein, R.sub.3 and
R.sub.4 each are a hydrogen atom or a substituent, provided that at
least one of R.sub.3 and R.sub.4 is the substituent; n2 is an
integer of 1 or 2; L2 is a bidentate ligand when n2 is 1; and p2
and q2 each are an integer of 0-4.] ##STR433## [wherein, R.sub.5
and R.sub.6 each are a hydrogen atom or a substituent. Z.sub.3 is
an atomic group necessary to form an aromatic hydrocarbon ring or
an aromatic heterocyclic ring; n3 is an integer of 1 or 2; L3 is a
bidentate ligand when n3 is 1; p3 is an integer of 0-3; and q3 is
an integer of 0-4.] ##STR434## [wherein, R.sub.7 and R.sub.8 each
are a hydrogen atom or a substituent. R.sub.9-R.sub.13 each are a
hydrogen atom or a substituent. n4 is an integer of 1 or 2; and L4
is a bidentate ligand when n4 is 1; p4 is an integer of 0-3; and q4
is an integer of 0-4.] ##STR435## [wherein, R.sub.14 and R.sub.15
each are a hydrogen atom or a substituent; Z.sub.4 is an atomic
group necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; n5 is an integer of 1 or 2; L5 is a bidentate
ligand when n5 is 1; p5 is an integer of 0-4; and q5 is an integer
of 0-3.] ##STR436## [wherein, R.sub.16 and R.sub.17 each are a
hydrogen atom or a substituent; R.sub.18-R.sub.22 each are a
hydrogen atom or a substituent; n6 is an integer of 1 or 2; L6 is a
bidentate ligand when n6 is 1; p6 is an integer of 0-3; and q7 is
an integer of 0-4.] ##STR437## [wherein, R.sub.23 and R.sub.24 each
are a hydrogen atom or a substituent; Z.sub.5 is an atomic group
necessary to form an aromatic heterocyclic ring together with a
nitrogen atom; n7 is an integer of 1 or 2; L7 is a bidentate ligand
when n7 is 1; p8 is an integer of 0-3; and q6 is an integer of
0-4.] ##STR438## [wherein, R.sub.25 and R.sub.26 each are a
hydrogen atom or a substituent; Z.sub.6 is an atomic group
necessary to form an aromatic heterocyclic ring together with a
nitrogen atom; n8 is an integer of 1 or 2; L8 is a bidentate ligand
when n8 is 1; p9 is an integer of 0-3; and q7 is an integer of
0-4.] ##STR439## [wherein, R.sub.27 and R.sub.28 each are a
hydrogen atom or a substituent, provided that at least one of
R.sub.27 and R.sub.28 is the substituent; L9 is a divalent linkage
group; X.sub.3 and X.sub.4 each are a carbon atom, a nitrogen atom,
an oxygen atom or a sulfur atom; Z.sub.7 and Z.sub.8 each are an
atomic group necessary to form an aromatic hydrocarbon ring or an
aromatic heterocyclic ring; n9 is an integer of 1 or 2; L9 is a
bidentate ligand when n9 is 1; and p10 and q8 each are an integer
of 0-4.]
10. The white light emitting organic electroluminescent element of
claim 2, wherein the blue light emitting ortho metalated complex
comprises at least one substructure selected from the group
consisting of Formulas (28)-(32) or a tautomer of the substructure.
##STR440## [wherein, C is a carbon atom; N is a nitrogen atom;
Z.sub.11 is an atomic group necessary to form an aromatic
heterocyclic ring together with a carbon atom and a nitrogen atom;
Z.sub.12 is an atomic group necessary to form a non-aromatic ring
together with a carbon atom; and M is a metal.] ##STR441##
[wherein, C is a carbon atom; N is a nitrogen atom; Z.sub.21 and
Z.sub.22 each are an atomic group necessary to form an aromatic
heterocyclic ring together with a carbon atom and a nitrogen atom;
and M is a metal.] ##STR442## [wherein, C is a carbon atom; N is a
nitrogen atom; Z.sub.31 is an atomic group necessary to form an
aromatic heterocyclic ring together with a carbon atom and a
nitrogen atom; Z.sub.32 is an atomic group comprising a carbon
atom, a nitrogen atom or an oxygen atom necessary to form a
5-membered or 6-membered aromatic heterocyclic ring together with a
carbon atom; and M is a metal.] ##STR443## [wherein, C is a carbon
atom; N is a nitrogen atom; Z.sub.41 is an atomic group necessary
to form a ring together with a carbon atom and a nitrogen atom;
Z.sub.42 is an atomic group necessary to form a ring together with
a carbon atom; and M is a metal.] ##STR444## [wherein, C is a
carbon atom; N is a nitrogen atom; Z.sub.51 is an atomic group
necessary to form an aromatic heterocyclic ring together with a
carbon atom and a nitrogen atom; Z.sub.52 is an atomic group to
form an azulene ring together with a carbon atom; and M is a
metal.]
11. The white light emitting organic electroluminescent element of
claim 2 comprising a platinum complex having a substructure
represented by Formula (A) or (B). ##STR445## [wherein, R.sub.1,
R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each are a
hydrogen atom or a substituent, provided that at least one of
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an electron donating
group; and Ra and Rb each are a substituent.] ##STR446## [wherein,
R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and
R.sub.17 each are a hydrogen atom or a substituent, provided that
at least one of R.sub.11 and R.sub.13 is an electron withdrawing
group; and Rc and Rd each are a substituent.]
12. The white light emitting organic electroluminescent element of
claim 2, wherein a shortest emission peak wavelength of the blue
light emitting ortho metalated complex is not more than 450 nm.
13. The white light emitting organic electroluminescent element of
claim 1, wherein the light emission layer or a layer adjacent to
the light emission layer comprises a compound represented by
Formula (33). ##STR447## [wherein, Z.sub.1 is an aromatic
heterocyclic ring which may have a substituent; Z.sub.2 is an
aromatic heterocyclic ring or an aromatic hydrocarbon ring each of
which may have a substituent; and Z.sub.3 is a divalent linkage
group or a single bonding arm; and R.sub.101 is a hydrogen atom or
a substituent.]
14. The white light emitting organic electroluminescent element of
claim 13, wherein Z.sub.1 of the compound represented by Formula
(33) is a 6-membered ring.
15. The white light emitting organic electroluminescent element of
claim 13, wherein Z.sub.2 of the compound represented by Formula
(33) is a 6-membered ring.
16. The white light emitting organic electroluminescent element of
claim 13, wherein Z.sub.3 of the compound represented by Formula
(33) is a single bonding arm.
17. The white light emitting organic electroluminescent element of
claim 13, wherein a molecular weight of the compound represented by
Formula (33) is not less than 450.
18. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-1). ##STR448## [wherein,
R.sub.501-R.sub.507 each independently are a hydrogen atom or a
substituent.]
19. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-2). ##STR449## [wherein,
R.sub.511-R.sub.517 each independently are a hydrogen atom or a
substituent.]
20. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-3). ##STR450## [wherein,
R.sub.521-R.sub.527 each independently are a hydrogen atom or a
substituent.]
21. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-4). ##STR451## [wherein,
R.sub.531-R.sub.537 each independently are a hydrogen atom or a
substituent.]
22. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-5). ##STR452## [wherein,
R.sub.541-R.sub.548 each independently are a hydrogen atom or a
substituent.]
23. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-6). ##STR453## [wherein,
R.sub.551-R.sub.558 each independently are a hydrogen atom or a
substituent.]
24. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-7). ##STR454## [wherein,
R.sub.561-R.sub.567 each independently are a hydrogen atom or a
substituent.]
25. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-8). ##STR455## [wherein,
R.sub.571-R.sub.577 each independently are a hydrogen atom or a
substituent.]
26. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-9). ##STR456## [wherein,
R.sub.581-R.sub.588 each independently are a hydrogen atom or a
substituent.]
27. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (33-10). ##STR457## [wherein,
R.sub.591-R.sub.598 each independently are a hydrogen atom or a
substituent.]
28. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) has at
least one of the groups represented by Formulas (34-1)-(34-10).
##STR458## ##STR459## [wherein, R.sub.502-R.sub.507,
R.sub.512-R.sub.517, R.sub.522-R.sub.527, R.sub.532-R.sub.537,
R.sub.542-R.sub.548, R.sub.552-R.sub.558, R.sub.562-R.sub.567,
R.sub.572-R.sub.577, R.sub.582-R.sub.588 and R.sub.592-R.sub.598,
each independently are a hydrogen atom or a substituent, and the
substituents may be the same with each other or may be
different.]
29. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (35). ##STR460## [wherein,
R.sub.601-R.sub.606 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.601-R.sub.606 is a
group selected from the groups represented by Formulas
(34-1)-(34-10).]
30. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (36). ##STR461## [wherein, R.sub.611-620
each independently are a hydrogen atom or a substituent, provided
that at least one of R.sub.611-R.sub.620 is one group selected from
the groups represented by Formulas (34-1)-(34-10).]
31. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (37). ##STR462## [wherein,
R.sub.621-R.sub.623 each independently are a hydrogen atom or a
substituent, however, at least one of R.sub.621-R.sub.623 is one
group selected from the groups represented by Formulas
(34-1)-(34-10).]
32. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (38). ##STR463## [wherein, P631-R.sub.645
each independently are a hydrogen atom or a substituent, provided
that at least one of R.sub.631-R.sub.645 is one group selected from
the groups represented by Formulas (34-1)-(34-10).]
33. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (39). ##STR464## [wherein,
R.sub.651-R.sub.656 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.651-R.sub.656 is
one group selected from the groups represented by Formulas
(34-1)-(34-10); na is an integer of 0-5; and nb is an integer of
1-6, provided that a sum of na and nb is 6.]
34. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (40). ##STR465## [wherein,
R.sub.661-R.sub.672 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.661-R.sub.672 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
35. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (41). ##STR466## [wherein,
R.sub.681-R.sub.688 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.681-R.sub.688 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
36. The white light emitting organic electroluminescent element of
claim 28, wherein the compound represented by Formula (33) is
represented by Formula (42). ##STR467## [wherein,
R.sub.689-R.sub.700 each independently are a hydrogen atom or a
substituent; L1 is a divalent linkage group; at least one of
R.sub.691-R.sub.700 is one group selected from the groups
represented by Formulas (34-1)-(34-10).]
37. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (43). ##STR468## wherein, R.sub.1 and
R.sub.2 each independently are a hydrogen atom or a substituent; n
and m each are an integer of 1-2; and k and l each are an integer
of 3-4, wherein, n+k=5 and l+m=5.]
38. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (44). ##STR469## [wherein, R.sub.1 and
R.sub.2 each independently are a hydrogen atom or a substituent; n
and m each are an integer of 1-2; and k and l each are an integer
of 3-4, wherein n+k=5 and l+m=5.]
39. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (45). ##STR470## [wherein, R.sub.1 and
R.sub.2 each independently are a hydrogen atom or a substituent; n
and m each are an integer of 1-2; and k and l each are an integer
of 3-4, wherein n+k=5 and l+m=5.]
40. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (46). ##STR471## [wherein, R.sub.1 and
R.sub.2 each independently are a hydrogen atom or a substituent; n
and m each are an integer of 1-2; and k and l each are an integer
of 3-4, wherein n+k=5 and l+m=5.]
41. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (47). ##STR472## [wherein, R.sub.1 and
R.sub.2 each independently are a hydrogen atom or a substituent; n
and m each are an integer of 1-2; k and l each are an integer of
3-4, wherein, n+k=5 and l+m=5; and Z.sub.1, Z.sub.2, Z.sub.3 and
Z.sub.4 each are a 6-membered aromatic heterocyclic ring comprising
at least one nitrogen atom.]
42. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (48). ##STR473## [wherein, o and p each are
an integer of 1-3; Ar.sub.1 and Ar.sub.2 each are an arylene group
or a divalent aromatic heterocyclic group; Z.sub.1 and Z.sub.2 each
are a 6-membered aromatic heterocyclic ring comprising at least one
nitrogen atom; and L is a divalent linkage group.]
43. The white light emitting organic electroluminescent element of
claim 13, wherein the compound represented by Formula (33) is
represented by Formula (49). ##STR474## [wherein, o and p each are
an integer of 1-3; Ar.sub.1 and Ar.sub.2 each are an arylene group
or a divalent aromatic heterocyclic group; Z.sub.1, Z.sub.2,
Z.sub.3 and Z.sub.4 each are a 6-membered aromatic heterocyclic
ring containing at least one nitrogen atom; and L is a divalent
linkage group.]
44. The white light emitting organic electroluminescent element of
claim 6, wherein the light emission layer or a layer adjacent to
the emission layer comprises the two kinds or more of
phosphorescent compounds.
45. A display having the white light emitting organic
electroluminescent element of claim 1.
46. An illuminator having the white light emitting organic
electroluminescent element of claim 1.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to a white light emitting
organic electroluminescent element, a display and an
illuminator.
BACKGROUND OF THE INVENTION
[0002] As an emission type electronic display device, an
electroluminescent device (ELD) is known. Elements constituting the
ELD include an inorganic electroluminescent element and an organic
electroluminescent element (hereinafter referred to also as an
organic EL element). Inorganic electroluminescent element has been
used for a plane light source, however, a high voltage alternating
current has been required to drive the element. An organic EL
element has a structure in which a light emitting layer containing
a light emitting compound is arranged between a cathode and an
anode, and an electron and a hole were injected into the light
emitting layer and recombined to form an exciton. The element emits
light, utilizing light (fluorescent light or phosphorescent light)
generated by inactivation of the exciton, and the element can emit
light by applying a relatively low voltage, namely, several volts
to several tens of volts. The element has a wide viewing angle and
a high visuality since the element is of self light emission type.
Further, the element is a thin, complete solid element, therefore,
the element is noted from the viewpoint of space saving and
portability.
[0003] For the practical use in the future, an organic EL element
is desired to emit light of high luminance with high efficiency at
a lower power.
[0004] For example, disclosed is an organic EL element exhibiting
higher luminance of emitting light with longer life in which a
stilbene derivative, a distyrylarylene derivative or a
tristyrylarylene derivative doped with a slight amount of a
fluorescent compound is employed (refer to Japanese Patent No.
3093796).
[0005] Also known are: an organic EL element which has an organic
light emitting layer containing 8-hydroxyquinoline aluminum complex
as a host compound doped with a slight amount of a fluorescent
compound (for example, refer to Japanese Patent Publication Open to
Public Inspection (hereafter referred to as JP-A) No. 63-264692);
and an organic EL element which has an organic light emitting layer
containing 8-hydroxyquinoline aluminum complex as a host compound
doped with a quinacridone type dye (for example, refer to JP-A No.
3-255190).
[0006] When light emitted through excited singlet state is used in
the organic EL element as disclosed in the above Patent documents,
the upper limit of the external quantum efficiency (.eta.ext) is
considered to be at most 5%, because the generation probability of
excited species capable of emitting light is 25%, since the
generation ratio of singlet excited species to triplet excited
species is 1:3, and further, external light emission efficiency is
20%.
[0007] Since an organic EL element, employing phosphorescence
through the excited triplet, has been reported by Prinston
University (refer to M. A. Baldo et al., nature, 395, 151-154
(1998)), studies on materials emitting phosphorescence at room
temperature have been actively carried out.
[0008] Examples are also reported in M. A. Baldo et al., Nature,
403(17), 750-753 (2000) or in U.S. Pat. No. 6,097,147.
[0009] As the upper limit of the internal quantum efficiency of the
excited triplet is 100%, the light emission efficiency of the
exited triplet is theoretically four times higher than that of the
excited singlet. Accordingly, light emission employing the excited
triplet may enable almost the same performance as a cold cathode
tube, and it is attracting attention to be applied as an
illuminator.
[0010] For example, S. Lamansky et al., J. Am. Chem. Soc., 123,
4304 (2001) reports that many kinds of heavy metal complexes such
as iridium complexes have been synthesized and studied.
[0011] In above mentioned M. A. Baldo et al., Nature, 403(17),
750-753 (2000), an example employing tris(2-phenylpyridine)iridium
as a dopant has been studied.
[0012] As other examples, M. E. Tompson et al. have reported the
application of L.sub.2Ir(acac) such as (ppy).sub.2Ir(acac) as a
dopant in the 10th International Workshop on Inorganic and Organic
Electroluminescence (EL '00, Hamamatsu), and Moon-Jae Youn. 0 g,
Tetsuo Tsutsui et al., have reported the application of
tris(2-(p-tolyl)pyridine)iridium (Ir(ptpy).sub.3), and
tris(benzo[h]quinoline)iridium (Ir(bzq).sub.3) as a dopant in the
10th International Workshop on Inorganic and Organic
Electroluminescence (EL '00, Hamamatsu). These metal complexes are
generally referred to as an ortho metalated iridium complex.
[0013] Also in aforementioned S. Lamansky et al., J. Am. Chem.
Soc., 123, 4304 (2001), an application of various iridium complexes
to an organic EL elements has been examined.
[0014] In order to obtain a higher emission efficiency, Ikai et al.
have reported an application of a hole transport compound as a host
material of a phosphorescent compound in the 10th International
Workshop on Inorganic and Organic Electroluminescence (EL '00,
Hamamatsu). Also, M. E. Tompson et al., have reported an
application of various electron-transport compounds as a host
material of a phosphorescent compound, which is further doped with
a novel iridium complex.
[0015] An ortho metalated complex having platinum as a central
metal instead of iridium is also attracting attention. Many
examples of this type of complex having a characteristic ligand
have been known (for example, refer to Patent Documents 1-5).
[0016] Since each of the above examples is related to
phosphorescent emission, the luminance, and the emission efficiency
are notably improved compared to the conventional organic EL
elements, however, the emission life of each element have been
shorter than those of the conventional organic EL elements. It has
not been fully easy for a high efficiency phosphorescent material
to satisfactorily shorten the emission wavelength and to improve
the emission life, and a fully satisfactory performance for the
practical use has not been obtained.
[0017] In order to shorten the emission wavelength, known are the
techniques in which an electron withdrawing group such as a
fluorine atom, a trifluoromethyl group or a cyano group, or a
ligand such as a picolinic acid or a pyrazabole ligand is
introduced in phenylpyridine (for example, refer to Patent
Documents 6-10). However, when these ligands are used, the emission
wavelengths are shortened to attain emission of blue light and an
element exhibiting a high efficiency can be obtained. However, the
emission life is notably deteriorated. TABLE-US-00001 Patent
Document 1 Japanese Patent Publication Open to Public Inspection
(hereafter referred to as JP-A) No. 2002-332291 Patent Document 2
JP-A No. 2002-332292 Patent Document 3 JP-A No. 2002-338588 Patent
Document 4 JP-A No. 2002-226495 Patent Document 5 JP-A No.
2002-234894 Patent Document 6 WO 02/15645 Patent Document 7 JP-A
No. 2003-123982 Patent Document 8 JP-A No. 2002-117978 Patent
Document 9 JP-A No. 2003-146996 Patent Document 10 WO 04/016711
[0018] Non-Patent Document 1 [0019] Inorganic Chemistry, Vol. 41,
No. 12, 3055-3066 Non-Patent Document 2 [0020] Applied Physics,
Letters, Vol. 79, Page 2082
[0021] Non-Patent Document 3 [0022] Applied Physics, Letters, Vol.
83, Page 3818
[0023] Non-Patent Document 4 [0024] New Journal of Chemistry, Vol.
26, Page 1171
SUMMARY THE INVENTION
[0025] An object of the invention is to provide an organic EL
element exhibiting a high luminance, a high emission efficiency and
an excellent CIE chromaticy of white light emission, and a display
and an illuminator employing the element.
[0026] One of the aspects of the present invention to achieve the
above abject is a white light emitting organic electroluminescent
element comprising two electrodes having therebetween one or more
constituting layers including a light emission layer, the one or
more constituting layers comprising at least two phosphorescent
compounds, wherein at least one of the phosphorescent compounds is
a green light emitting ortho metalated complex; and a spectral
ratio of the green light emitting ortho metalated complex in ae
emission spectral distribution in a range of 400-800 nm is not less
than 60%.
BRIEF DESCRIPTION OF THE DRAWINGS
[0027] FIG. 1 is a schematic drawing illustrating an example of a
display equipped with a white light emitting organic EL
element.
[0028] FIG. 2 is a schematic drawing of display portion A.
[0029] FIG. 3 is an equivalent circuit diagram of a drive circuit
constituting a pixel.
[0030] FIG. 4 is a schematic drawing of a display based on a
passive matrix method.
[0031] FIG. 5 is a simple schematic drawing of a sealing structure
of white light emitting organic EL element-1.
[0032] FIG. 6 is a schematic drawing of an illuminator equipped
with a white emitting organic EL element.
[0033] FIG. 7 shows a spectral curve of sample GOLED-1 for
measuring spectrum component of green light.
[0034] FIG. 8 shows a spectral curve of sample GOLED-5 for
measuring spectrum component of green light.
DETAILED DESCRIPTION OF THE INVENTION
[0035] The above-described object of the present invention has been
achieved by the following structures 1-46.
[0036] (1) A white light emitting organic electroluminescent
element comprising two electrodes having therebetween one or more
constituting layers including a light emission layer, the one or
more constituting layers comprising at least two phosphorescent
compounds, wherein
[0037] at least one of the phosphorescent compounds is a green
light emitting ortho metalated complex; and
[0038] a spectral ratio of the green light emitting ortho metalated
complex in ae emission spectral distribution in a range of 400-800
nm is not less than 60%.
[0039] (2) The white light emitting organic electroluminescent
element of Item (1), wherein
[0040] at least one of the phosphorescent compounds is a blue light
emitting ortho metalated complex; and
[0041] a shortest emission peak wavelength of the blue light
emitting ortho metalated complex is not more than 455 nm.
[0042] (3) The white light emitting organic electroluminescent
element of Item (1) or (2), wherein [0043] at least one of the
phosphorescent compounds is a red light emitting ortho metalated
complex.
[0044] (4) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein [0045] the blue light emitting
ortho metalated complex has at least one of the substructures
represented by Formulas (1) to (6) or at last one of tautomers of
the substructures represented by Formulas (1) to (6). ##STR1##
[wherein, Z11 is an atomic group necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring; R.sub.11,
R.sub.12 and R.sub.13 each are a hydrogen atom or a substituent;
and M.sub.11 is a metal belonging to one of Groups 8 to 10 of the
periodic table.] ##STR2## [wherein, Z21 is an atomic group
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; R.sub.21, R.sub.22 and R.sub.13 each are a
hydrogen atom or a substituent; and M.sub.21 is a metal belonging
to one of Groups 8 to 10 of the periodic table.] ##STR3## [wherein,
Z31 is an atomic group necessary to form an aromatic hydrocarbon
ring or an aromatic heterocyclic ring; X.sub.31, X.sub.32 and
X.sub.33 each are a carbon atom, --C(R.sub.3)--, a nitrogen atom or
--N(R.sub.3)-- (wherein, R.sub.3 is a hydrogen atom or a
substituent); C.sub.31 is a carbon atom; M.sub.31 is a metal
belonging to one of Groups 8 to 10 of the periodic table; and a
bond between C.sub.31 and N, a bond between N and X.sub.33, a bond
between X.sub.32 and X.sub.33, a bond between X.sub.31 and
X.sub.32, and a bond between C.sub.31 and X.sub.31 each are a
single bond or a double bond.] ##STR4## [wherein, Z41 is an atomic
group necessary to form an aromatic heterocyclic ring; at least one
of X.sub.41 and X.sub.42 is a nitrogen atom or --N(R.sub.4)--
(wherein, R.sub.4 is a hydrogen atom or a substituent); M.sub.41 is
a metal belonging to one of Groups 8 to 10 of the periodic table;
C.sub.41, C.sub.42 and C.sub.43 each are a carbon atom; M.sub.41 is
a metal belonging to one of Groups 8 to 10 of the periodic table;
and a bond between C.sub.41 and C.sub.42, a bond between C.sub.41
and X.sub.42, a bond between X.sub.41 and X.sub.42, a bond between
X.sub.41 and C.sub.43, and a bond between C.sub.42 and C.sub.43
each are a single bond or a double bond.] ##STR5## [wherein, Z51 is
an atomic group necessary to form an aromatic hydrocarbon ring or
an aromatic heterocyclic ring; X.sub.51 is an oxygen atom or a
sulfur atom; R.sub.51 and R.sub.52 each are a hydrogen atom or a
substituent; and M.sub.51 is a metal belonging to one of Groups 8
to 10 of the periodic table.] ##STR6## [wherein, Z61 is an atomic
group necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring. X.sub.61, X.sub.62 and X.sub.63 each are a
carbon atom, --C(R.sub.6)--, a nitrogen atom or --N(R.sub.6)--
(wherein, R.sub.6 is a hydrogen atom or a substituent); and
M.sub.61 is a metal belonging to one of Groups 8 to 10 of the
periodic table.]
[0046] (5) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein
[0047] the blue light emitting ortho metalated complex is a
platinum complex represented by Formula (7). ##STR7## [wherein,
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7
each are a hydrogen atom or a substituent, provided that, at least
one of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and
R.sub.7 is a substituent; Ra is a substituent; Xa is an oxygen atom
or a sulfur atom; Y.sub.1-L.sub.1-Y.sub.1 is a bidentate ligand;
Y.sub.1 and Y.sub.2 each independently are an oxygen atom, a
nitrogen atom, a carbon atom or a sulfur atom; and L.sub.1 is an
atomic group necessary to form a bidentate ligand together with
Y.sub.1 and Y.sub.2.]
[0048] (6) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein
[0049] the blue light emitting ortho metalated complex is a metal
complex having a substructure represented by Formula (8) or (9).
##STR8## [wherein, A, B and C each are a hydrogen atom or a
substituent, provided that at least two of A, B and C are
represented by -Xa-(Ra).sub.na (wherein Ra is a substituent, Xa is
an oxygen atom, a sulfur atom or a nitrogen atom, and na is 1 or
2.), which may be the same or different; R.sub.1, R.sub.2, R.sub.3,
R.sub.4 and R.sub.5 each are a hydrogen atom or a substituent; and
M.sub.1 is an element belonging to one Groups 8 to 10 of the
periodic table.] ##STR9## [wherein, Rb, Rc and Rd each are a
substituent; Xb, Xc and Xd each are an oxygen atom, a sulfur atom
or a nitrogen atom; nb, nc and nd each are 1 or 2; R.sub.6,
R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each are a hydrogen atom or
a substituent; and M.sub.2 is an element belonging to one of Groups
8 to 10 of the periodic table.]
[0050] (7) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein
[0051] the blue light emitting ortho metalated complex is a metal
complex having a ligand represented by Formula (10), a metal
complex having a substructure represented by Formula (11) or (12)
or a metal complex having a tautomer of the substructure
represented by Formula (11) or (12). ##STR10## [wherein, X.sub.1,
X.sub.2, X.sub.3 and R.sub.4 each independently are a carbon atom
or a nitrogen atom; C.sub.1 and C.sub.2 each are a carbon atom; Z1
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.1, X.sub.1 and X.sub.3; Z2 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.2, X.sub.2 and X.sub.4;
A.sub.1 is a nitrogen atom or a boron atom; R.sub.1 is a
substituent; and a bond between C.sub.1 and X.sub.1, a bond between
C.sub.2 and X.sub.2, a bond between X.sub.1 and X.sub.3, and a bond
between X.sub.2 and X.sub.4 each are a single bond or a double
bond.] ##STR11## [wherein, C.sub.3, C.sub.4, C.sub.5, C.sub.6 and
C.sub.7 each are a carbon atom; Z3 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with together with C.sub.3, C.sub.4 and
C.sub.5; Z4 represents a group of atoms necessary to form an
aromatic heterocyclic ring together with together with C.sub.6,
C.sub.7 and N; A.sub.2 is a nitrogen atom or a boron atom; R.sub.2
is a substituent; and M.sub.11 is an element belonging to one of
Groups 8 to 10 of the periodic table; and a bond between C.sub.3
and C.sub.4, a bond between C.sub.4 and C.sub.5, a bond between
C.sub.6 and C.sub.7, and a bond between C.sub.7 and N each are a
single bond or a double bond.] ##STR12## [wherein, A.sub.3 is a
nitrogen atom or a boron atom; R.sub.3 is a substituent; R.sub.4
and R.sub.5 each are a substituent; n1 and n2 each are an integer
of 0-3; and M.sub.12 is an element belonging to one of Groups 8 to
10 of the periodic table.]
[0052] (8) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein
[0053] the blue light emitting ortho metalated complex is a metal
complex having a ligand represented by Formula (13), a metal
complex having a substructure represented by Formula (14), a metal
complex having a substructure represented by Formula (15) or a
tautomer of the substructure, a metal complex having a ligand
represented by Formula (16), a metal complex having a substructure
represented by Formula (17) or a metal complex having a
substructure represented by Formula (18). ##STR13## [wherein,
X.sub.1, X.sub.2, X.sub.3 and X.sub.4 each independently are a
carbon atom or a nitrogen atom; C.sub.1 and C.sub.2 each are a
carbon atom; Z1 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.1, X.sub.1 and X.sub.3; Z2 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.2, X.sub.2 and X.sub.4;
A.sub.1 is a carbon atom or a silicon atom; R.sub.1 and R.sub.2
each independently are a hydrogen atom or a substituent; and a bond
between C.sub.1 and X.sub.1, a bond between C.sub.2 and X.sub.2, a
bond between X.sub.1 and X.sub.3, and a bond between X.sub.2 and
X.sub.4 each are a single bond or a double bond.] ##STR14##
[wherein, C.sub.3, C.sub.4, C.sub.5, C.sub.6 and X.sub.7 each are a
carbon atom; Z3 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.5, C.sub.3 and C.sub.7; Z4 represents a group of atoms
necessary to form an aromatic heterocyclic ring together with
C.sub.6, C.sub.4 and N; A.sub.2 is a carbon atom or a silicon atom;
R.sub.3 and R.sub.4 each independently are a hydrogen atom or a
substituent. M.sub.11 is an element belonging to one of Groups 8 to
10 of the periodic table; and a bond between C.sub.5 and C.sub.3, a
bond between C.sub.3 and C.sub.7, a bond between C.sub.6 and
C.sub.4, and a bond between C.sub.4 and N each are a single bond or
a double bond.] ##STR15## [wherein, A.sub.3 is a carbon atom or a
silicon atom; R.sub.5 and R.sub.6 each independently are a hydrogen
atom or a substituent; and R.sub.7 and R.sub.8 each independently
are a substituent; n1 and n2 each independently are an integer of
0-3; M.sub.12 is an element belonging to one of Groups 8 to 10 of
the periodic table.] ##STR16## [wherein, X.sub.3, X.sub.4, X.sub.5
and X.sub.6 each independently are a carbon atom or a nitrogen
atom; C.sub.8-C.sub.13 each are a carbon atom; Z5 represents a
group of atoms necessary to form an aromatic hydrocarbon ring or an
aromatic heterocyclic ring together with C.sub.8, X.sub.3 and
X.sub.5; Z6 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.9, X.sub.4 and X.sub.6; Z7 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.10 and C.sub.11; Z8
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.12 and C.sub.13; A.sub.4 is a carbon atom or a silicon atom;
and a bond between X.sub.3 and X.sub.5, a bond between X.sub.4 and
X.sub.6, a bond between C.sub.8 and X.sub.3, and a bond between
C.sub.9 and X.sub.4, a bond between C.sub.10 and C.sub.11 and a
bond between C.sub.12 and C.sub.13 each are a single bond or a
double bond.] ##STR17## [wherein, C.sub.14-C.sub.22 each are a
carbon atom; Z9 represents a group of atoms necessary to form an
aromatic hydrocarbon ring or an aromatic heterocyclic ring together
with C.sub.16, C.sub.14 and C.sub.18; Z11 represents a group of
atoms necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.19 and C.sub.20; Z12
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.21 and C.sub.22; each are an atomic group necessary to form
an aromatic hydrocarbon ring or an aromatic heterocyclic ring; Z10
represents a group of atoms necessary to form an aromatic
heterocyclic ring together with C.sub.17, C.sub.15 and N; A.sub.5
is a carbon atom or a silicon atom; M.sub.21 is an element
belonging to one of Groups 8 to 10 of the periodic table; and a
bond between C.sub.18 and C.sub.14, a bond between C.sub.14 and
C.sub.16, a bond between C.sub.17 and C.sub.15, and a bond between
C.sub.15 and N, a bond between C.sub.19 and C.sub.20, and a bond
between C.sub.21 and C.sub.22 each are a single bond or a double
bond.] ##STR18## [wherein, Z13 represents a group of atoms
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring together with C.sub.23 and C.sub.24; Z14
represents a group of atoms necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring together with
C.sub.25 and C.sub.26; A.sub.5 is a carbon atom or a silicon atom.
R.sub.9 and R.sub.10 each independently are a substituent; n3 and
n4 each is an integer of 0-3; M.sub.22 is an element belonging to
one of Groups 8 to 10 of the periodic table; and a bond between
C.sub.23 and C.sub.24, and a bond between C.sub.25 and C.sub.26
each are a single bond or a double bond.]
[0054] (9) The white light emitting organic electroluminescent
element of Item (2) or (3), wherein
[0055] the blue light emitting ortho metalated complex comprises a
platinum complex selected from the group consisting of Formulas
(19)-(27). ##STR19## [wherein, R.sub.1 and R.sub.2 each are a
hydrogen atom or a substituent, provided that at least one of
R.sub.1 and R.sub.2 is the substituent; X.sub.1 and X.sub.2 each
are a carbon atom, a nitrogen atom or a sulfur atom; and Z.sub.1
and Z.sub.2 each are an atomic group necessary to form an aromatic
hydrocarbon ring or an aromatic heterocyclic ring; n1 is an integer
of 1 or 2; L1 is a bidentate ligand when n1 is 1; and p1 and q1
each are an integer of 0-4.] ##STR20## [wherein, R.sub.3 and
R.sub.4 each are a hydrogen atom or a substituent, provided that at
least one of R.sub.3 and R.sub.4 is the substituent; n2 is an
integer of 1 or 2; L2 is a bidentate ligand when n2 is 1; and p2
and q2 each are an integer of 0-4.] ##STR21## [wherein, R.sub.5 and
R.sub.6 each are a hydrogen atom or a substituent. Z3 is an atomic
group necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; n3 is an integer of 1 or 2; L3 is a bidentate
ligand when n3 is 1; p3 is an integer of 0-3; and q3 is an integer
of 0-4.] ##STR22## [wherein, R.sub.7 and R.sub.8 each are a
hydrogen atom or a substituent. R.sub.9-R.sub.13 each are a
hydrogen atom or a substituent. n4 is an integer of 1 or 2; and L4
is a bidentate ligand when n4 is 1; p4 is an integer of 0-3; and q4
is an integer of 0-4.] ##STR23## [wherein, R.sub.14 and R.sub.15
each are a hydrogen atom or a substituent; Z.sub.4 is an atomic
group necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; n5 is an integer of 1 or 2; L5 is a bidentate
ligand when n5 is 1; p5 is an integer of 0-4; and q5 is an integer
of 0-3.] ##STR24## [wherein, R.sub.16 and R.sub.17 each are a
hydrogen atom or a substituent; R.sub.18-R.sub.22 each are a
hydrogen atom or a substituent; n6 is an integer of 1 or 2; L6 is a
bidentate ligand when n6 is 1; p6 is an integer of 0-3; and q7 is
an integer of 0-4.] ##STR25## [wherein, R.sub.23 and R.sub.24 each
are a hydrogen atom or a substituent; Z.sub.5 is an atomic group
necessary to form an aromatic heterocyclic ring together with a
nitrogen atom; n7 is an integer of 1 or 2; L7 is a bidentate ligand
when n7 is 1; p8 is an integer of 0-3; and q6 is an integer of
0-4.] ##STR26## [wherein, R.sub.25 and R.sub.26 each are a hydrogen
atom or a substituent; Z.sub.6 is an atomic group necessary to form
an aromatic heterocyclic ring together with a nitrogen atom; n8 is
an integer of 1 or 2; L8 is a bidentate ligand when n8 is 1; p9 is
an integer of 0-3; and q7 is an integer of 0-4.] ##STR27##
[wherein, R.sub.27 and R.sub.28 each are a hydrogen atom or a
substituent, provided that at least one of R.sub.27 and R.sub.28 is
the substituent; L0 is a divalent linkage group; X.sub.3 and
X.sub.4 each are a carbon atom, a nitrogen atom, an oxygen atom or
a sulfur atom; Z.sub.7 and Z.sub.8 each are an atomic group
necessary to form an aromatic hydrocarbon ring or an aromatic
heterocyclic ring; n9 is an integer of 1 or 2; L9 is a bidentate
ligand when n9 is 1; and p10 and q8 each are an integer of
0-4.]
[0056] (10) The white light emitting organic electroluminescent
element of claims 2 or 3, wherein
[0057] the blue light emitting ortho metalated complex comprises at
least one substructure selected from the group consisting of
Formulas (28)-(32) or a tautomer of the substructure. ##STR28##
[wherein, C is a carbon atom; N is a nitrogen atom; Z.sub.11 is an
atomic group necessary to form an aromatic heterocyclic ring
together with a carbon atom and a nitrogen atom; Z.sub.12 is an
atomic group necessary to form a non-aromatic ring together with a
carbon atom; and M is a metal.] ##STR29## [wherein, C is a carbon
atom; N is a nitrogen atom; Z.sub.21 and Z.sub.22 each are an
atomic group necessary to form an aromatic heterocyclic ring
together with a carbon atom and a nitrogen atom; and M is a metal.]
##STR30## [wherein, C is a carbon atom; N is a nitrogen atom;
Z.sub.31 is an atomic group necessary to form an aromatic
heterocyclic ring together with a carbon atom and a nitrogen atom;
Z.sub.32 is an atomic group comprising a carbon atom, a nitrogen
atom or an oxygen atom necessary to form a 5-membered or 6-membered
aromatic heterocyclic ring together with a carbon atom; and M is a
metal.] ##STR31## [wherein, C is a carbon atom; N is a nitrogen
atom; Z.sub.41 is an atomic group necessary to form a ring together
with a carbon atom and a nitrogen atom; Z.sub.42 is an atomic group
necessary to form a ring together with a carbon atom; and M is a
metal.] ##STR32## [wherein, C is a carbon atom; N is a nitrogen
atom; Z.sub.51 is an atomic group necessary to form an aromatic
heterocyclic ring together with a carbon atom and a nitrogen atom;
Z.sub.52 is an atomic group to form an azulene ring together with a
carbon atom; and M is a metal.]
[0058] (11) The white light emitting organic electroluminescent
element of Item (2) or (3) comprising a platinum complex having a
substructure represented by Formula (A) or (B). ##STR33## [wherein,
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7
each are a hydrogen atom or a substituent, provided that at least
one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an electron
donating group; and Ra and Rb each are a substituent.] ##STR34##
[wherein, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15,
R.sub.16 and R.sub.17 each are a hydrogen atom or a substituent,
provided that at least one of R.sub.11 and R.sub.13 is an electron
withdrawing group; and Rc and Rd each are a substituent.]
[0059] (12) The white light emitting organic electroluminescent
element of any one of Items (2) to (11), wherein
[0060] a shortest emission peak wavelength of the blue light
emitting ortho metalated complex is not more than 450 nm.
[0061] (13) The white light emitting organic electroluminescent
element of any one of Items (1) to (12), wherein
[0062] the light emission layer or a layer adjacent to the light
emission layer comprises a compound represented by Formula (33).
##STR35## [wherein, Z.sub.1 is an aromatic heterocyclic ring which
may have a substituent; Z.sub.2 is an aromatic heterocyclic ring or
an aromatic hydrocarbon ring each of which may have a substituent;
and Z.sub.3 is a divalent linkage group or a single bonding arm;
and R.sub.101 is a hydrogen atom or a substituent.]
[0063] (14) The white light emitting organic electroluminescent
element of Item (13), wherein Z.sub.1 of the compound represented
by Formula (33) is a 6-membered ring.
[0064] (15) The white light emitting organic electroluminescent
element of Item (13) or (14), wherein Z.sub.2 of the compound
represented by Formula (33) is a 6-membered ring.
[0065] (16) The white light emitting organic electroluminescent
element of any one of Items (13) to (15), wherein Z.sub.3 of the
compound represented by Formula (33) is a single bonding arm.
[0066] (17) The white light emitting organic electroluminescent
element of any one of Items (13) to (16), wherein a molecular
weight of the compound represented by Formula (33) is not less than
450.
[0067] (18) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-1).
##STR36## [wherein, R.sub.501-R.sub.507 each independently are a
hydrogen atom or a substituent.]
[0068] (19) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-2).
##STR37## [wherein, R.sub.511-R.sub.517 each independently are a
hydrogen atom or a substituent.]
[0069] (20) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-3).
##STR38## [wherein, R.sub.521-R.sub.527 each independently are a
hydrogen atom or a substituent.]
[0070] (21) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-4).
##STR39## [wherein, R.sub.531-R.sub.537 each independently are a
hydrogen atom or a substituent.]
[0071] (22) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-5).
##STR40## [wherein, R.sub.541-R.sub.548 each independently are a
hydrogen atom or a substituent.]
[0072] (23) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-6).
##STR41## [wherein, R.sub.551-R.sub.558 each independently are a
hydrogen atom or a substituent.]
[0073] (24) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-7).
##STR42## [wherein, R.sub.561-R.sub.567 each independently are a
hydrogen atom or a substituent.]
[0074] (25) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-8).
##STR43## [wherein, R.sub.571-R.sub.577 each independently are a
hydrogen atom or a substituent.]
[0075] (26) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-9).
##STR44## [wherein, R.sub.581-R.sub.588 each independently are a
hydrogen atom or a substituent.]
[0076] (27) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (33-10).
##STR45## [wherein, R.sub.592-R.sub.598 each independently are a
hydrogen atom or a substituent.]
[0077] (28) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) has at least one of the groups
representing by Formulas (34-1)-(34-10). ##STR46## [wherein,
R.sub.502-R.sub.507, R.sub.512-R.sub.517, R.sub.522-R.sub.527,
R.sub.532-R.sub.537, R.sub.542-R.sub.548, R.sub.552-R.sub.558,
R.sub.562-R.sub.567, R.sub.572-R.sub.577, R.sub.582-R.sub.588 and
R.sub.592-R.sub.598, each independently are a hydrogen atom or a
substituent, and the substituents may be the same with each other
or may be different.]
[0078] (29) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (35). ##STR47## [wherein,
R.sub.601-R.sub.606 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.601-R.sub.606 is a
group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0079] (30) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (36). ##STR48## [wherein,
R.sub.611-R.sub.620 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.611-R.sub.620 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0080] (31) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (37). ##STR49## [wherein,
R.sub.621-R.sub.623 each independently are a hydrogen atom or a
substituent, however, at least one of R.sub.621-R.sub.623 is one
group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0081] (32) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (38). ##STR50## [wherein,
R.sub.631-R.sub.645 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.631-R.sub.645 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0082] (33) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (39). ##STR51## [wherein,
R.sub.651-R.sub.656 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.651-R.sub.656 is
one group selected from the groups represented by Formulas
(34-1)-(34-10); na is an integer of 0-5; and nb is an integer of
1-6, provided that a sum of na and nb is 6.]
[0083] (34) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (40). ##STR52## [wherein,
R.sub.661-R.sub.672 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.661-R.sub.672 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0084] (35) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (41). ##STR53## [wherein,
R.sub.681-R.sub.688 each independently are a hydrogen atom or a
substituent, provided that at least one of R.sub.681-R.sub.688 is
one group selected from the groups represented by Formulas
(34-1)-(34-10).]
[0085] (36) The white light emitting organic electroluminescent
element of Item (28), wherein the compound represented by Formula
(33) is represented by Formula (42). ##STR54## [wherein,
R.sub.691-R.sub.700 each independently are a hydrogen atom or a
substituent; L.sub.1 is a divalent linkage group; at least one of
R.sub.691-R.sub.700 is one group selected from the groups
represented by Formulas (34-1)-(34-10).]
[0086] (37) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (43).
##STR55## [wherein, R.sub.1 and R.sub.2 each independently are a
hydrogen atom or a substituent; n and m each are an integer of 1-2;
and k and l each are an integer of 3-4, wherein, n+k=5 and
1+m=5.]
[0087] (38) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (44).
##STR56## [wherein, R.sub.1 and R.sub.2 each independently are a
hydrogen atom or a substituent; n and m each are an integer of 1-2;
and k and l each are an integer of 3-4, wherein n+k=5 and
1+m=5.]
[0088] (39) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (45).
##STR57## [wherein, R.sub.1 and R.sub.2 each independently are a
hydrogen atom or a substituent; n and m each are an integer of 1-2;
and k and l each are an integer of 3-4, wherein n+k=5 and
1+m=5.]
[0089] (40) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (46).
##STR58## [wherein, R.sub.1 and R.sub.2 each independently are a
hydrogen atom or a substituent; n and m each are an integer of 1-2;
and k and 1 each are an integer of 3-4, wherein n+k=5 and
1+m=5.]
[0090] (41) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (47).
##STR59## [wherein, R.sub.1 and R.sub.2 each independently are a
hydrogen atom or a substituent; n and m each are an integer of 1-2;
k and 1 each are an integer of 3-4, wherein, n+k=5 and 1+m=5; and
Z.sub.1, Z.sub.2, Z.sub.3 and Z.sub.4 each are a 6-membered
aromatic heterocyclic ring comprising at least one nitrogen
atom.]
[0091] (42) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (48).
##STR60## [wherein, o and p each are an integer of 1-3; Ar.sub.1
and Ar.sub.2 each are an arylene group or a divalent aromatic
heterocyclic group; Z.sub.1 and Z.sub.2 each are a 6-membered
aromatic heterocyclic ring comprising at least one nitrogen atom;
and L is a divalent linkage group.]
[0092] (43) The white light emitting organic electroluminescent
element of any one of Items (13) to (17), wherein the compound
represented by Formula (33) is represented by Formula (49).
##STR61## [wherein, o and p each are an integer of 1-3; Ar.sub.1
and Ar.sub.2 each are an arylene group or a divalent aromatic
heterocyclic group; Z.sub.1, Z.sub.2, Z.sub.3 and Z.sub.4 each are
a 6-membered aromatic heterocyclic ring containing at least one
nitrogen atom; and L is a divalent linkage group.]
[0093] (44) The white light emitting organic electroluminescent
element of Item (6), wherein the light emission layer or a layer
adjacent to the emission layer comprises the two kinds or more of
phosphorescent compounds.
[0094] (45) A display having the white light emitting organic
electroluminescent element of any one of Items (1) to (44).
[0095] (46) An illuminator having the white light emitting organic
electroluminescent element of any one of Items (1) to (44).
[0096] An organic EL element of the present invention has been able
to achieve an organic EL element exhibiting high emission luminance
and high emission efficiency as well as having high CIE color
purity of white emission by employing an constitution described in
any one of aforesaid items (1)-(7). Further, the present invention
can also provide a display and an illumination utilizing the
aforesaid element.
[0097] In the following, details of each constituent element
according to the present invention will be explained in
succession.
<Green Light Emitting, Red Light Emitting and Blue Light
Emitting Ortho Metalated Complex>
[0098] Green light emitting, red light emitting and blue light
emitting ortho metalated complexes according to the present
invention each will now be explained.
[0099] Green light emitting, red light emitting and blue light
emitting ortho metalated complexes according to the present
invention each are a phosphorescent compound; a layer containing
each ortho metalated complex may be any layer of an organic EL
element of the present invention, however, an emission layer and/or
a positive hole blocking layer are preferably utilized; and in the
case of the complex being contained in an emission layer, it is
possible to provide an organic EL element of the present invention
with effects of improving emission luminance and emission
efficiency in addition to increasing CIE color purity of white
emission, by utilizing the aforesaid complex as an emission dopant
in the aforesaid emission layer.
<Green Light Emitting Ortho Metalated Complex>
[0100] A green light emitting ortho metal complex according to the
present invention will now be explained.
[0101] A green light emitting ortho metal complex according to the
present invention is a phosphorescent compound and has a spectral
component ratio of said green light emitting ortho metal complex,
which occupies the white emission spectral distribution of organic
EL element of the present invention within a region of 400-800 nm,
is not less than 60%, preferably not less than 70% and more
preferably in a range of 70-85%.
[0102] The calculation method of a spectral component ratio
according to the present invention will be detailed in examples
described later, however, the wave forms were compared, utilizing a
white emission spectrum curve obtained at the time of emission of
an element and a green emission spectrum curve obtained by
measurement of an element sample which had been separately prepared
only from a green light emitting ortho metalated complex alone, and
the ratio of an emission spectral component of a green light
emitting ortho metalated complex in a white emission spectral
distribution was calculated.
[0103] A green light emitting ortho metal complex according to the
present invention is an ortho metalated complex which has the
emission maximum wavelength in a range of 500-570 nm and is
comprised of a transition metal as the central metal, and not less
than 70% of energy distribution of the emission spectral is
preferably in a range of 500-570 nm.
[0104] Specifically, utilized can be those having the
above-described emission characteristics among ortho metalated
complexes described in patents such as Japanese Translation of PCT
International Application Publication No. (hereinafter referred to
as JT-PCT) 2003-526876, WO 00/70655 pamphlet, JT-PCT 2002-525808,
WO 01/41512 pamphlet, JT-PCT 2004-506305 and WO 02/15645 pamphlet.
As the central metal, transition metals belonging to the 8-10th
groups of the periodic table are preferable and Ir or Pt is
specifically preferable.
[0105] Further, as a green light emitting ortho metalated complex
according to the present invention, specifically preferably
utilized are complexes represented by following Formula (C) or (D).
##STR62##
[0106] In the formulas, X.sub.1, Y.sub.1, X.sub.2 and Y.sub.2 each
are an oxygen atom or a nitrogen atom; X.sub.1 and Y.sub.1 together
with Z.sub.1, X.sub.2 and Y.sub.2 together with Z.sub.2, each form
a bidentate ligand. m and n are 0 or 1. .beta.-diketones and
salicylic acid derivatives are preferable as a ligand formed by
X.sub.1 and Y.sub.1 together with Z1. Further, .beta.-diketones,
salicylic acid derivatives and picolinic acid derivatives are
preferable as a ligand formed by X.sub.2 and Y.sub.2 together with
Z.sub.2.
[0107] R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are a hydrogen atom or
a substituent, and said substituent includes, for example, an alkyl
group (such as a methyl group, an ethyl group, an isopropyl group,
a hydroxyethyl group, a methoxymethyl group, a trifluoromethyl
group, a t-butyl group, a pentyl group, an octyl group, a nonyl
group and a decyl group), a cycloalkyl group (such as a cyclopentyl
group and a cyclohexyl group), an aralkyl group (such as a benzyl
group and a 2-phenetyl group), an aromatic hydrocarbon group (such
as a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl
group, a xylyl group, a biphenylyl group, a naphtyl group, an
anthoryl group and a phenanthryl group), an aromatic heterocyclic
group (such as a furyl group, a thienyl group, a pyridyl group, a
pyridazinyl group, a pyrimidinyl group, a pyradinyl group, a
triazinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, a quinazolynyl group, a carbazolyl group, a
carbolinyl group, a diazacarbazolyl group (a diazacarbazolyl group
refers to those in which any one of carbon atoms constituting a
carboline ring of said carbolinyl group is substituted by a
nitrogen atom) and a phthalazinyl group), an alkoxyl group (such as
an ethoxy group, an isopropoxy group and a butoxy group), an
aryloxy group (such as a phenoxy group and a naphthyloxy group), a
cyano group, a hydroxyl group, an alkenyl group (such as a vinyl
group), a styryl group, a halogen atom (such as a chlorine atom, a
bromine atom, an iodine atom and a fluorine atom). These groups may
be further substituted.
[0108] Among those described above, a preferable substituent
includes an alkyl group having a carbon number of 1-10, an alkoxyl
group having a carbon number of 1-10 and a halogen atom.
[0109] In the following, preferable green light emitting ortho
metalated complexes are specifically exemplified; however, the
present invention is not limited thereto. ##STR63## ##STR64##
##STR65## <Red Light Emitting Ortho Metalated Complex>
[0110] A red light emitting ortho metal complex according to the
present invention is an ortho metalated complex, which is comprised
of a transition metal as the central metal and has the maximum
emission wavelength in a range of 570-650 nm, and is preferably has
the maximum emission wavelength of not shorter than 590 nm.
Further, not less than 70% of energy distribution of the emission
spectrum is preferably in a range of not shorter than 580 nm.
Specific examples of a red light emitting ortho metalated complex
according to a white light emitting organic EL element of the
present invention include the following compounds. ##STR66##
[0111] Further, as specific examples of a green light emitting
ortho metalated complex and a red light emitting ortho metalated
complex according to the present invention, compounds
conventionally well known in the art can be utilized and utilized
can be compounds described in such as J. Am. Chem. Soc. Vol. 123,
pp. 4304-4312 (2001), Inorganic Chemistry, vol. 40 p. 1704 (2001),
JP-A (hereinafter, JP-A refers to Japanese Patent Publication Open
to Public Inspection No.) 2003-272861, JP-A 2004-111193, Japanese
Patent Application Nos. 2003-150762 and 2003-150763, JP-A Nos.
2001-247859, 2001-181616, 2001-181617, 2002-175884, 2002-332291,
2002-363552, 2002-332291, 2002-338588, WO 00/70655 pamphlet, JP-A
Nos. 2002-203678 and 2001-345183, WO 02/44189 pamphlet, JP-A Nos.
2002-332292, 2003-059667, 2002-332292 and 2002-252888. Further,
combination use thereof is also possible.
<Blue Light Emitting Ortho Metalated Complex>
[0112] A blue light emitting ortho metalated complex according to
the present invention is an ortho metalated complex which is
comprised of a transition metal as the central metal and has the
emission maximum wavelength in a range of 400-500 nm, and the
shortest emission maximum wavelength is preferably not longer than
455 nm.
[0113] As a blue light emitting ortho metalated complex according
to the present invention, complexes classified in seven types of
embodiments described in any one of aforesaid items (4)-(10) are
preferably utilized. In the following, said seven types of
embodiments are classified into (a)-(h) and each thereof will be
specifically explained.
EMBODIMENT (a)
[0114] The case of utilizing a complex, which is provided with at
least one type of partial structures represented by aforesaid
Formulas (1)-(6) or at least one type of a tautomer of each partial
structures represented by said Formulas (1)-(6) as a partial
structure, as a blue light emitting ortho metalated complex.
[0115] A layer containing a metal complex having a partial
structure of Formulas (1)-(6) or a tautomer of said Formulas
(1)-(6) is preferably an emission layer and/or a positive hole
blocking layer, and further, when the metal complex is contained in
an emission layer, it is possible to achieve increase (higher
luminance) of taking out quantum efficiency or elongation of the
emission life, of an organic EL element of the present invention,
by utilizing the complex as an emission dopant in an emission
layer.
[0116] <Formula (1) or Tautomer of Said Formula (1)>
[0117] In Formula (1) or a tautomer of said Formula (1), an
aromatic hydrocarbon ring represented by Z.sub.11 includes such as
a benzene ring, a biphenyl ring, a naphthalene ring, an azulene
ring, an anthrathene ring, a phenanthrene ring, a pyrene ring, a
chrysene ring, a naphthacene ring, a triphenylene ring, a
o-terphenyl ring, a m-terphenyl ring, a p-terphenyl ring, an
acenaphthene ring, a coronene ring, a fluorene ring, a
fluoranthrene ring, a naphthacene ring, a pentacene ring, a
perylene ring, a pentaphene ring, a picene ring, a pyrene ring, a
pyranthrene ring and an anthraathrene ring.
[0118] Preferably utilized among them is a benzene ring. Further,
the aforesaid aromatic hydrocarbon ring may be provided with a
substituent represented by each of R.sub.11, R.sub.12 and R.sub.13
in aforesaid Formula (1).
[0119] In Formula (1) or a tautomer of said Formula (1), an
aromatic hydrocarbon ring represented by Z.sub.11 includes a furan
ring, a thiophene ring, a pyridine ring, a pyridazine ring, a
pyrimidine ring, a pyradine ring, a triazine ring, a benzoimidazole
ring, an oxadiazole ring, a triazole ring, an imidazole ring, a
pyrazole ring, a thiazole ring, an indole ring, a benzoimidazole
ring, a benzothiazole ring, a benzooxazole ring, a quinoxaline
ring, a quinazoline ring, a phthalazine ring, a carbazole ring, a
carboline ring and a ring in which at least one of carbon atoms of
a hydrocarbon ring constituting a carboline ring is further
substituted by a nitrogen atom.
[0120] Preferable among them is a pyridine ring. Further, the
aforesaid aromatic heterocyclic ring may be provided with a
substituent represented by each of R.sub.11, R.sub.12 and R.sub.13
in aforesaid Formula (1).
[0121] In Formula (1) or a tautomer of said Formula (1), a
substituent represented by each of R.sub.11, R.sub.12 and R.sub.13
includes, for example, an alkyl group (such as a methyl group, an
ethyl group, an isopropyl group, a hydroxyethyl group, a
methoxymethyl group, a trifluoromethyl group, a t-butyl group), a
cycloalkyl group (such as a cyclopentyl group and a cyclohexyl
group), an aralkyl group (such as a benzyl group and a 2-phenetyl
group), an aromatic hydrocarbon group (such as a phenyl group, a
p-chlorophenyl group, a mesityl group, a tolyl group, a xylyl
group, a biphenylyl group, a naphtyl group, an anthoryl group and a
phenanthryl group), an aromatic heterocyclic group (such as a furyl
group, a thienyl group, a pyridyl group, a pyridazinyl group, a
pyrimidinyl group, a pyradinyl group, a triazinyl group, an
imidazolyl group, a pyrazolyl group, a thiazolyl group, a
quinazolynyl group, a carbazolyl group, a carbolinyl group, a
diazacarbazolyl group (a diazacarbazolyl group refers to those in
which any one of carbon atoms constituting a carboline ring of said
carbolinyl group is substituted by a nitrogen atom) and a
phthalazinyl group), an alkoxyl group (such as an ethoxy group, an
isopropoxy group and a butoxy group), an aryloxy group (such as a
phenoxy group and a naphthyloxy group), a cyano group, a hydroxyl
group, an alkenyl group (such as a vinyl group), a styryl group, a
halogen atom (such as a chlorine atom, a bromine atom, an iodine
atom and a fluorine atom). These groups may be further provided
with a substituent.
[0122] Among them, in the present invention, at least one of the
above-described groups represented by R.sub.11, R.sub.12 and
R.sub.13 is preferably the above-described aromatic hydrocarbon
group or aromatic heterocyclic group.
[0123] In Formula (1) or a tautomer of said Formula (1), M.sub.11
is a metal (may be either a metal atom or an ion) belonging to the
8th-10th groups of the periodic table, however, preferably utilized
among them are platinum (Pt) and iridium (Ir). Further, in a metal
complex having Formula (1) or a tautomer of said Formula (1) as a
partial structure, M.sub.11 may be either a metal atom or an
ion.
[0124] In the present invention, a metal complex is formed by
forming a coordination bond between Formula (1) or a tautomer of
said Formula (1) (also referred to as complex formation) and a
central metal (also may be an ion) represented by M.sub.11.
[0125] <Formula (2) or Tautomer of Said Formula (2)>
[0126] In Formula (2) or a tautomer of said Formula (2), an
aromatic hydrocarbon ring represented by Z.sub.21 is identical with
an aromatic hydrocarbon ring represented by Z.sub.11 in Formula (1)
or a tautomer of said Formula (1).
[0127] In Formula (2) or a tautomer of said Formula (2), an
aromatic heterocyclic ring represented by Z.sub.21 is identical
with an aromatic heterocyclic ring represented by Z.sub.11 in
Formula (1) or a tautomer of said Formula (1).
[0128] In Formula (2) or a tautomer of said Formula (2), a
substituent represented by each of R.sub.21, R.sub.22 and R.sub.23
is identical with a substituent represented by each of R.sub.11,
R.sub.12 and R.sub.13 in Formula (1) or a tautomer of said Formula
(1).
[0129] In Formula (2) or a tautomer of said Formula (2), a metal
(also may be an ion), which is represented by M.sub.21 and belongs
to the 8th-10th groups of the periodic table, is identical with a
metal (also may be an ion), which is represented by M.sub.11 and
belongs to the 8th-10th groups of the periodic table, in Formula
(1) or a tautomer of said Formula (1).
[0130] <Formula (3) or Tautomer of Said Formula (3)>
[0131] In Formula (3) or a tautomer of said Formula (3), an
aromatic hydrocarbon ring represented by Z.sub.31 is identical with
an aromatic hydrocarbon ring represented by Z.sub.11 in Formula (1)
or a tautomer of said Formula (1).
[0132] In Formula (3) or a tautomer of said Formula (3), an
aromatic heterocyclic ring represented by Z.sub.31 is identical
with an aromatic heterocyclic ring represented by Z.sub.11 in
Formula (1) or a tautomer of said Formula (1).
[0133] In Formula (3) or a tautomer of said Formula (3), a
substituent represented by R.sub.3 of --N(R.sub.3), which is
represented by each of X.sub.31, X.sub.32 and X.sub.33, is
identical with a substituent represented by each of R.sub.11,
R.sub.12 and R.sub.13 in Formula (1) or a tautomer of said Formula
(1).
[0134] In Formula (3) or a tautomer of said Formula (3), a metal
(also may be an ion), which is represented by M.sub.31 and belongs
to the 8th-10th groups of the periodic table, is identical with a
metal (also may be an ion), which is represented by M.sub.11 and
belongs to the 8th-10th groups of the periodic table, in Formula
(1) or a tautomer of said Formula (1).
[0135] <Formula (4) or Tautomer of Said Formula (4)>
[0136] In Formula (4) or a tautomer of said Formula (4), an
aromatic heterocyclic ring represented by Z.sub.41 is identical
with an aromatic heterocyclic ring represented by Z.sub.11 in
Formula (1) or a tautomer of said Formula (1).
[0137] In Formula (4) or a tautomer of said Formula (4), a
substituent represented by each of X.sub.41 X.sub.42 and X.sub.43
is identical with a substituent represented by each of R.sub.11
R.sub.12 and R.sub.13 in Formula (1) or a tautomer of said Formula
(1).
[0138] In Formula (4) or a tautomer of said Formula (4), a metal
(also may be an ion), which is represented by M.sub.41 and belongs
to the 8th-10th groups of the periodic table, is identical with a
metal (also may be an ion), which is represented by M.sub.11 and
belongs to the 8th-10th groups of the periodic table, in Formula
(1) or a tautomer of said Formula (1).
[0139] <Formula (5) or Tautomer of Said Formula (5)>
[0140] In Formula (5) or a tautomer of said Formula (5), an
aromatic hydrocarbon ring represented by Z.sub.51 is identical with
an aromatic hydrocarbon ring represented by Z11 in Formula (1) or a
tautomer of said Formula (1).
[0141] In Formula (5) or a tautomer of said Formula (5), an
aromatic heterocyclic ring represented by Z.sub.51 is identical
with an aromatic heterocyclic ring represented by Z11 in Formula
(1) or a tautomer of said Formula (1).
[0142] In Formula (5) or a tautomer of said Formula (5), a
substituent represented by each of R.sub.51 and R.sub.52 is
identical with a substituent represented by each of R.sub.11,
R.sub.12 and R.sub.13 in Formula (1) or a tautomer of said Formula
(1).
[0143] In Formula (5) or a tautomer of said Formula (5), a metal
(also may be an ion), which is represented by M.sub.51 and belongs
to the 8th-10th groups of the periodic table, is identical with a
metal (also may be an ion), which is represented by M.sub.11 and
belongs to the 8th-10th groups of the periodic table, in Formula
(1) or a tautomer of said Formula (1).
[0144] <Formula (6) or Tautomer of Said Formula (6)>
[0145] In Formula (6) or a tautomer of said Formula (6), an
aromatic hydrocarbon ring represented by Z.sub.61 is identical with
an aromatic hydrocarbon ring represented by Z11 in Formula (1) or a
tautomer of said Formula (1).
[0146] In Formula (6) or a tautomer of said Formula (6), an
aromatic heterocyclic ring represented by Z.sub.61 is identical
with an aromatic heterocyclic ring represented by Z.sub.11 in
Formula (1) or a tautomer of said Formula (1).
[0147] In Formula (6) or a tautomer of said Formula (6), a metal
(also may be an ion), which is represented by M.sub.61 and belongs
to the 8th-10th groups of the periodic table, is identical with a
metal (also may be an ion), which is represented by M.sub.11 and
belongs to the 8th-10th groups of the periodic table, in Formula
(1) or a tautomer of said Formula (1).
[0148] In the following, specific examples of a metal complex,
which is provided with aforesaid Formulas (1)-(6) or a tautomer of
said Formulas (1)-(6) as a partial structure, will be shown,
however the present invention is not limited thereto. ##STR67##
##STR68## ##STR69## ##STR70## ##STR71## ##STR72## ##STR73##
##STR74## ##STR75## ##STR76## ##STR77## ##STR78## ##STR79##
##STR80## ##STR81## ##STR82## ##STR83## ##STR84## ##STR85##
##STR86## ##STR87## ##STR88## ##STR89## ##STR90## ##STR91##
##STR92## ##STR93## ##STR94## ##STR95## ##STR96## ##STR97##
##STR98## ##STR99## ##STR100## ##STR101## ##STR102## ##STR103##
##STR104## ##STR105##
EMBODIMENT (b)
[0149] The case in which a platinum complex represented by
aforesaid Formula (7) is utilized as a blue light emitting ortho
metalated complex.
[0150] <Metal Complex Represented by Formula (7)>
[0151] A platinum complex represented by Formula (7) according to
the present invention will now be explained.
[0152] In Formula (7), R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5,
R.sub.6 and R.sub.7 are a hydrogen atom or a substituent, however,
at least of them is necessarily a substituent. Even in the case
that at least two of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5,
R.sub.6 and R.sub.7 are substituents, they never form a ring by
bonding to each other. Further, Ra is a substituent, and Xa is an
oxygen atom or a sulfur atom.
[0153] In Formula (7), a substituent represented by aforesaid Ra is
not specifically limited and includes an alkyl group (such as a
methyl group, an ethyl group, an isopropyl group and a tert-butyl
group), a cycloalkyl group (such as a cyclohexyl group, a
cyclopentyl group and a cyclopropyl group), an alkenyl group (such
as a vinyl group, an allyl group and a 2-butenyl group), an alkynyl
group (such as an ethynyl group and a propynyl group), an aryl
group (such as a phenyl group, a 2-naphthyl group, a 2-pyridyl
group, a 2-thienyl group and a 3-furyl group) and a heterocyclic
group (a N-morpholyl group and a 2-tetrahydrofuranyl group).
[0154] Among them, Ra is preferably an alkyl group having a carbon
number of 1-30, and Ra-Xa- is preferably an alkoxy group or an
alkylthio group.
[0155] Further, a substituent represented by aforesaid
R.sub.1-R.sub.7 includes, for example, an alkyl group (such as a
methyl group, an isopropyl group and a t-butyl group), a cycloalkyl
group (such as a cyclopentyl group and a cyclopropyl group), an
alkenyl group (such as vinyl group, an allyl group and a 2-butenyl
group), an alkynyl group (such as ethynyl group and a propynyl
group), an aryl group (such as a phenyl group, a 2-naphthyl group,
a 9-phenanthryl group, a 2-pyridyl group, a mesityl group, a
carbazolyl group, a fluorenyl group, a 2-thienyl group and a
3-furyl group), a heterocyclic group (such as a N-morpholyl group
and a 2-tetrahydrofuranyl group), an amino group, an alkylamino
group (such as dimethylamino group and a diphenylamino group), a
halogen atom (such as a fluorine atom, a chlorine atom, a bromine
atom and an iodine atom), an alkoxy group (such as a methoxy group,
an ethoxy group and an isopropoxy group), an aryloxy group (such as
a phenoxy group and a perfluorophenoxy group), an acylamino group
(such as an acetamido group and a benzoylamido group), a
sulfonamido group (such as a methanesulfonamido group, a
butanesulfonamido group and a benzenesulfonamido group), a
carboalkoxy group (such as a carboethoxy group), an aryloxy
carbonyl group (such as a phenoxy carbonyl group), an acyloxy group
(such as an acetoxy group and a benzoyloxy group), an alkylthio
group (such as a methylthio group), a cyano group and a
fluorohydrocarbon group (such as a trifluoromethyl group and a
pentafluorophenyl group).
[0156] In Formula (7), Y.sub.1-L.sub.2-Y.sub.2 is a bidentate
ligand; Y.sub.1 and Y.sub.2 each independently are an oxygen atom,
a nitrogen atom, a carbon atom or a sulfur atom; and L.sub.1
together with Y.sub.1 and Y.sub.2 is an atomic group necessary to
form a bidentate ligand.
[0157] Specific examples of a bidentate ligand represented by
Y.sub.1-L.sub.2-Y.sub.2 are not specifically limited; however, are
preferably derivatives of such as phenylpyridine, acetic acid,
acetyl acetone, a thiocarbamic acid derivative, 2-acylphenol and
picolinic acid, which may be provided with a substituent.
[0158] Further, as at least one substituent, which is preferably
introduced at 3p-6p positions of the aforesaid structure together
with such as the aforesaid alkoxy group and alkylthio group and not
to form a ring by bonding to each other, is a group represented by
R.sub.1, R.sub.2, R.sub.3 and R.sub.2 in Formula (7), and at least
one of the substituents represented by R.sub.1-R.sub.4 is
preferably an electron donating substituent. Further, more
preferable are the case in which at least two types are electron
donating substituents.
[0159] Further, most preferable is the case, in which R.sub.2 and
R.sub.4 in Formula (7) are electron donating substituents.
[0160] As an electron donating substituent among the aforesaid
groups includes an alkyl group, an alkoxy group and an alkylamino
group.
[0161] Next, preferable as these substituents are a halogen atom
and more preferably a fluorine atom among them. It is considered
that since a fluorine atom has a .pi. doner property, it may work
like an electron doner, the effect of which can provide preferable
element abilities.
[0162] In the following, with respect to a platinum complex
represented by aforesaid Formula (7) utilized in the present
invention, specific examples will be listed, however, the present
invention is not limited thereto. ##STR106## ##STR107## ##STR108##
##STR109## ##STR110## ##STR111## ##STR112## ##STR113## ##STR114##
##STR115## ##STR116## ##STR117## ##STR118## ##STR119## ##STR120##
##STR121## ##STR122## ##STR123## ##STR124## ##STR125##
EMBODIMENT (c)
[0163] The case in which a platinum complex represented by each of
aforesaid Formulas (8) and (9) as a blue light emitting ortho
metalated complex.
[0164] <Metal Complex Represented by Formula (8)>
[0165] A metal complex represented by aforesaid Formula (8)
according to the present invention will now be explained.
[0166] In Formula (8), A, B and C are a hydrogen atom or a
substituent, however, at least two of them are represented by
aforesaid Formula (2) and may be different from each other. A
substituent represented by A, B and C is not specifically limited
and preferably includes an alkyl group (such as a methyl group, an
isopropyl group and a tert-butyl group), a cycloalkyl group (such
as cyclohexyl group, a cyclopentyl group and a cyclopropyl group),
an alkenyl group (such as vinyl group, an allyl group, a 2-butenyl
group), an alkynyl group (such as an ethynyl group and a propynyl
group), an aryl group (such as a phenyl group, a 2-naphthyl group,
a 9-phenanthryl group, a 2-pyridyl group, a 2-thienyl group, a
3-furyl group, a mesityl group, a carbazolyl group and a fluorenyl
group), a heterocyclic group (such as a N-morpholyl group and a
2-tetrahydrofuranyl group), an amino group (such as a dimethylamino
group and a diphenylamino group), a halogen atom (such as chlorine
atom, a bromine atom and iodine atom), an alkoxy group (a methoxy
group, an ethoxy group and an isopropoxy group), an aryloxy group
(such as a phenoxy group, perfluorophenoxy group), an alkylthio
group (such as methylthio group, an ethylthio group, a propylthio
group, a pentylthio group, a hexylthio group, an octylthio group
and dodecylthio group), an arylthio group (such as a phenylthio
group and a naphthylthio group), a cyano group, a fluorohydrocarbon
group (such as a trifluoromethyl group and a pentafluorophenyl
group), a cyano group, a fluororhydrocarbon group (such as
trifluoromethyl group, pentafluorophenyl group), a silyl group
(such as a triphenylsylyl and trimethylsilyl). Specifically
preferable among them are an amino group, an alkoxy group, an
aryloxy group, an aryl group, an alkylthio group, an arylthio group
and an aryl group. Most preferable are an amino group, an alkoxy
group and an alkylthio group.
[0167] In Formula (8), R.sub.1, R.sub.2, R.sub.3, R.sub.4 and
R.sub.5 are a hydrogen atom or a substituent. Substituents
represented by R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are
identical with those explained above as substituents represented by
A, B and C.
[0168] In Formula (8), M.sub.1 is an element belonging to the 8th,
9th or 10th group of the periodic table. Elements belonging to the
8th, 9th or 10th group of the periodic table are preferably
ruthenium, rhodium, palladium, osmium, iridium and platinum and
most preferably iridium and platinum.
[0169] In Formula (2), Ra is a substituent. The substituents
represented by Ra are identical with those explained as
substituents represented by aforesaid A, B and C. Specifically
preferable among them is an alkyl group.
[0170] In Formula (8), Xa is an oxygen atom, a sulfur atom or a
nitrogen atom. na is 1 or 2.
[0171] In Formula (8), the case, in which all of A, B and C are
Formula (2), is most preferred.
[0172] In Formula (8), when two of A, B, and C are Formula (2), the
case, in which Formula (2) substitutes at 4 and 6p positions, is
most preferable, and the case, in which Formula (2) substitutes at
4 and 4p positions, is preferable.
[0173] <Metal Complex Represented by Formula (9)>
[0174] A metal complex represented by Formula (9) according to the
present invention will now be explained.
[0175] In Formula (9), Rb, Rc and Rd are a substituent, and the
substituents represented by Rb, Rc and Rd are identical with those
explained as substituents represented by A, B and C in aforesaid
Formula (8). Substituents of Ra, Rc and Rd are preferably an alkyl
group.
[0176] In Formula (9), Xb, Xc and Xd are an oxygen atom, a sulfur
atom or a nitrogen atom. The combination of Xb, Xc and Xd is
preferably (1) Xd is a nitrogen atom, and Xb and Xc are an oxygen
atom; (2) Xd is a sulfur atom, and Xb and Xc are an oxygen atom; or
(3) Xb, Xc and Xd are an oxygen atom.
[0177] In Formula (9), nb, nc and nd are 1 or 2.
[0178] In Formula (9), R.sub.6, R.sub.7, R.sub.8, R.sub.9 and
R.sub.10 are a hydrogen atom or a substituent. The substituent
represented by R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are
identical with those explained as substituent represented by A, B
and C in aforesaid Formula (8).
[0179] In formula (9), M.sub.2 is an element belonging to the 8th,
9th or 10th group of the periodic table. Elements belonging to the
8th, 9th or 10th group of the periodic table are preferably
ruthenium, rhodium, palladium, osmium, iridium and platinum and
most preferably iridium and platinum.
[0180] In the following, specific examples of complexes represented
by Formula (8) or (9) will be listed; however, the present
invention is not limited thereto. ##STR126## ##STR127## ##STR128##
##STR129## ##STR130## ##STR131## ##STR132## ##STR133## ##STR134##
##STR135## ##STR136## ##STR137## ##STR138## ##STR139## ##STR140##
##STR141## ##STR142## ##STR143## ##STR144## ##STR145## ##STR146##
##STR147## ##STR148## ##STR149## ##STR150## ##STR151## ##STR152##
##STR153## ##STR154## ##STR155## ##STR156##
EMBODIMENT (d)
[0181] The case in which a metal complex having a ligand
represented by aforesaid Formula (10), a metal complex having a
partial structure represented by following Formula (11) or (12), or
a metal complex having a tautomer of each partial structure
represented by said Formula (11) or (12) is utilized as a blue
light emitting ortho metalated complex.
[0182] <Metal Complex Having Ligand Represented by Formula
(10)>
[0183] A metal complex having a ligand represented by Formula (10)
will now be explained.
[0184] First, a ligand represented by Formula (10) will be
explained.
[0185] In Formula (10), an aromatic hydrocarbon ring which is
formed by each of Z.sub.1 together with C.sub.1, X.sub.1 and
X.sub.3, Z.sub.2 together with C.sub.2, X.sub.2 and X.sub.4,
includes such as a benzene ring, a biphenyl ring, a naphthalene
ring, an azulene ring, an anthrathene ring, a phenanthrene ring, a
pyrene ring, a chrisene ring, a naphthacene ring, a triphenylene
ring, an o-terphenyl ring, a m-terphenyl ring, a p-terphenyl ring,
an acenaphtene ring, a coronene ring, a fluorene ring, a
fluoranthrene ring, a naphthacene ring, a pentacene ring, a
perylene ring, a pentaphene ring, a picene ring, a pyrene ring, a
pyranthrene ring and an anthraathrene ring.
[0186] Preferably utilized among them is a benzene ring. Further,
the aforesaid aromatic hydrocarbon ring may be provided with a
substituent represented by R.sub.1 in aforesaid Formula (10), which
will be described later.
[0187] In Formula (10), an aromatic heterocyclic ring, which is
formed by each of Z.sub.1 together with C.sub.1, X.sub.1 and
X.sub.3, and Z.sub.2 together with C.sub.2, X.sub.2 and X.sub.4
includes such as a furan ring, a thiophene ring, a pyridine ring, a
pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine
ring, a benzoimidazole ring, an oxadiazole ring, a triazole ring,
an imidazole ring, a pyrazole ring, a thiazole ring, an indole
ring, a benzoimidazole ring, a benzothiazole ring, a benzooxazole
ring, a quinoxaline ring, a quinazoline ring, a phthalazine ring, a
carbazole ring, a carboline ring and a ring in which at least one
of carbon atoms of a hydrocarbon ring, which constitutes a
carboline ring, is substituted by a nitrogen atom.
[0188] Preferable among them is a pyridine ring. Further, the
aforesaid aromatic heterocyclic ring may be provided with a
substituent represented by R.sub.1 in aforesaid Formula (10), which
will be described later.
[0189] In Formula (10), a substituent represented by R.sub.1
includes, for example, an alkyl group (such as a methyl group, an
ethyl group, an isopropyl group, a hydroxyethyl group, a
methoxymethyl group, a trifluoromethyl group and a t-butyl group),
a cycloalkyl group (such as a cyclopentyl group and a cyclohexyl
group), an aralkyl group (such as a benzyl group and a 2-phenetyl
group), an aromatic hydrocarbon group (such as a phenyl group, a
p-chlorophenyl group, a mesityl group, a tolyl group, a xylyl
group, a biphenylyl group, a naphtyl group, an anthoryl group and a
phenanthryl group), an aromatic heterocyclic group (such as a furyl
group, a thienyl group, a pyridyl group, a pyridazinyl group, a
pyridinyl group, a pyrimidinyl, a pyradinyl group, a triazinyl
group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a
quinazolynyl group, a carbazolyl group and a phthalazinyl), an
alkoxyl group (such as a methoxy group, an ethoxy group, an
isopropoxy group and a butoxy group), an aryloxy group (such as a
phenoxy group and a naphthyloxy group), a cyano group, a hydroxyl
group, an alkenyl group (such as a vinyl group), a styryl group, a
halogen atom (such as a chlorine atom, a bromine atom, an iodine
atom and a fluorine atom). These groups may be further
substituted.
[0190] Among them, in the present invention, at least one of groups
represented by aforesaid R.sub.1 is preferably the above-described
aromatic hydrocarbon group or aromatic heterocyclic group.
[0191] A coordination bond is formed (also referred to as complex
formation) between a ligand represented by Formula (10) and a
central metal (may be either a metal or an ion) resulting in
formation of a metal complex.
[0192] Herein, when a coordination bond is formed between the
aforesaid ligand and a central metal (which will be described
later), a coordination bond or a covalent bond is preferably formed
with X.sub.3 and/or X.sub.4 among atoms which constitute a ligand
represented by aforesaid Formula (10).
[0193] <Metal Complex Having Formula (11) or Tautomer Thereof as
Partial Structure>
[0194] A metal complex according to the present invention, which is
provided with Formula (11) or a tautomer thereof as a partial
structure, will now be explained.
[0195] In Formula (11), an aromatic hydrocarbon ring formed by
Z.sub.3 together with C.sub.3, C.sub.4 and C.sub.5 is identical
with an aromatic hydrocarbon ring formed by Z.sub.1 together with
C.sub.1, X.sub.1 and X.sub.3 in Formula (10).
[0196] In Formula (11), an aromatic heterocyclic ring formed by
Z.sub.3 together with C.sub.3, C.sub.4 and C.sub.5 is identical
with an aromatic hydrocarbon ring formed by Z.sub.1 together with
C.sub.1, X.sub.1 and X.sub.3 in Formula (10).
[0197] In Formula (11), an aromatic heterocyclic ring, which is
formed by Z.sub.4 together with C.sub.6, C.sub.7 and N includes
such as a pyridine ring, a pyridazine ring, a pyrimidine ring, a
pyrazine ring, a triazine ring, a benzoimidazole ring, an
oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole
ring, a thiazole ring, an indole ring, a benzoimidazole ring, a
benzothiazole ring, a benzooxazole ring, a quinoxaline ring, a
quinazoline ring, a phthalazine ring, a carbazole ring and a ring
in which at least one of carbon atoms of hydrocarbon rings, which
constitutes a carboline ring, is further substituted by a nitrogen
atom. Further, the aforesaid aromatic heterocyclic ring may be
provided with a substituent represented by R.sub.1 in aforesaid
Formula (10).
[0198] In Formula (11), a substituent represented by R.sub.2 is
identical with a substituent represented by R.sub.1 in aforesaid
Formula (10).
[0199] In Formula (11), an element represented by M.sub.11
belonging to the 8th-10th groups of the periodic table is
preferably such as platinum (Pt) and iridium (Ir). Further, in
Formula (11), M.sub.11 may be either a metal or an ion.
[0200] <Metal Complex Having Formula (12) or Tautomer Thereof as
Partial Structure>
[0201] A metal complex, according to the present invention, which
is provided with Formula (12) or a tautomer thereof as a partial
structure, will now be explained.
[0202] In Formula (12), a substituent represented by R.sub.3 is
identical with a substituent represented by R.sub.1 in aforesaid
Formula (10).
[0203] In Formula (12), a substituent represented by R.sub.4 and
R.sub.5 is identical with a substituent represented by R.sub.1 in
aforesaid Formula (10).
[0204] In Formula (12), an element represented by M.sub.12
belonging to the 8th-10th groups of the periodic table is
preferably such as platinum (Pt) and iridium (Ir). Further, in
Formula (12), M.sub.12 may be either a metal or an ion.
[0205] In the following, specific examples of a metal complex
having a ligand represented by Formula (10), a metal complex having
a partial structure represented by aforesaid Formula (11) or (12),
or a metal complex having a tautomer of each partial structure
represented by said Formula (11) or (12) will be listed, however,
the present invention is not limited thereto. ##STR157## ##STR158##
##STR159## ##STR160## ##STR161## ##STR162## ##STR163## ##STR164##
##STR165## ##STR166## ##STR167## ##STR168## ##STR169## ##STR170##
##STR171## ##STR172## ##STR173## ##STR174## ##STR175## ##STR176##
##STR177## ##STR178## ##STR179## ##STR180## ##STR181## ##STR182##
##STR183## ##STR184## ##STR185##
EMBODIMENT (e)
[0206] The case in which a metal complex having a ligand
represented by following Formula (13), a metal complex having a
partial structure represented by following Formula (14), a metal
complex having a partial structure represented by following Formula
(15) or a tautomer thereof as a partial structure, a metal complex
having a ligand represented by following Formula (16), a metal
complex having a partial structure represented by following Formula
(17), or a metal complex having a partial structure represented by
following Formula (18) is utilized as a blue light emitting ortho
metalated complex.
[0207] <Metal Complex Having Ligand Represented by Formula
(13)>
[0208] A metal complex having a ligand represented by Formula (13)
will now be explained.
[0209] First, a ligand represented by Formula (13) will be
explained.
[0210] In Formula (13), an aromatic hydrocarbon ring which is
formed by Z.sub.1 together with C.sub.1, X.sub.1 and X.sub.3
includes such as a benzene ring, a biphenyl ring, a naphthalene
ring, an azulene ring, an anthrathene ring, a phenanthrene ring, a
pyrene ring, a chrisene ring, a naphthacene ring, a triphenylene
ring, an o-terphenyl ring, a m-terphenyl ring, a p-terphenyl ring,
an acenaphtene ring, a coronene ring, a fluorene ring, a
fluoranthrene ring, a naphthacene ring, a pentacene ring, a
perylene ring, a pentaphene ring, a picene ring, a pyrene ring, a
pyranthrene ring and an anthraathrene ring.
[0211] Preferably utilized among them is a benzene ring. Further,
the aforesaid aromatic hydrocarbon ring may be provided with a
substituent represented by each of R.sub.1 and R.sub.2 in aforesaid
Formula (13), which will be described later.
[0212] In Formula (13), an aromatic heterocyclic ring, which is
formed by Z.sub.1 together with C.sub.1, X.sub.1 and X.sub.3
includes such as a furan ring, a thiophene ring, a pyridine ring, a
pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine
ring, a benzoimidazole ring, an oxadiazole ring, a triazole ring,
an imidazole ring, a pyrazole ring, a thiazole ring, an indole
ring, a benzothiazole ring, a benzooxazole ring, a quinoxaline
ring, a quinazoline ring, a phthalazine ring, a carbazole ring, a
carboline ring, a ring in which at least one of carbon atoms of a
hydrocarbon ring, which constitutes a carboline ring, is
substituted by a nitrogen atom.
[0213] Preferable among them is a pyridine ring. Further, the
aforesaid aromatic heterocyclic ring may be provided with a
substituent represented by each of R.sub.1 and R.sub.2 in aforesaid
Formula (13), which will be described later.
[0214] In Formula (13), a substituent each independently
represented by R.sub.1 and R.sub.2 includes, for example, an alkyl
group (such as a methyl group, an ethyl group, an isopropyl group,
a hydroxyethyl group, a methoxymethyl group, a trifluoromethyl
group and a t-butyl group), a cycloalkyl group (such as a
cyclopentyl group and a cyclohexyl group), an aralkyl group (such
as a benzyl group and a 2-phenetyl group), an aromatic hydrocarbon
group (such as a phenyl group, a p-chlorophenyl group, a mesityl
group, a tolyl group, a xylyl group, a biphenylyl group, a naphtyl
group, an anthoryl group and a phenanthryl group), an aromatic
heterocyclic group (such as a furyl group, a thienyl group, a
pyridyl group, a pyridazinyl group, a pyrimidinyl group, a
pyradinyl group, a triazinyl group, an imidazolyl group, a
pyrazolyl group, a thiazolyl group, a quinazolynyl group, a
carbazolyl group and a phthalazinyl), an alkoxyl group (such as a
methoxy group, an ethoxy group, an isopropoxy group and a butoxy
group), an aryloxy group (such as a phenoxy group and a naphthyloxy
group), a cyano group, a hydroxyl group, an alkenyl group (such as
a vinyl group), a styryl group, a halogen atom (such as a chlorine
atom, a bromine atom, an iodine atom and a fluorine atom). These
groups may be further substituted.
[0215] Among them, in the present invention, at least one of groups
represented by aforesaid R.sub.1 and R.sub.2 is preferably the
above-described aromatic hydrocarbon group or aromatic heterocyclic
group.
[0216] A coordination bond is formed (also referred to as complex
formation) between a ligand represented by Formula (13) and a
central metal (may be either a metal or an ion) resulting in
formation of a metal complex.
[0217] Herein, when a coordination bond is formed between the
aforesaid ligand and a cetral metal (which will be described
later), a coordination bond or a covalent bond is preferably formed
with X.sub.3 and/or X.sub.4 among atoms which constitute a ligand
represented by aforesaid Formula (13).
[0218] <Metal Complex Having Partial Structure Represented by
Formula (14)>
[0219] A metal complex provided with a partial structure
represented by Formula (14) according to the present invention will
now be explained.
[0220] In Formula (14), an aromatic hydrocarbon ring formed by
Z.sub.3 together with C.sub.5, C.sub.3 and C.sub.7 is identical
with an aromatic hydrocarbon ring formed by Z.sub.1 together with
C.sub.1, X.sub.1 and X.sub.3 in Formula (13).
[0221] In Formula (14), an aromatic heterocyclic ring formed by
Z.sub.3 together with C.sub.5, C.sub.3 and C.sub.7 is identical
with an aromatic hydrocarbon ring formed by Z.sub.1 together with
C.sub.1, X.sub.1 and X.sub.3 in Formula (13).
[0222] In Formula (14), an aromatic heterocyclic ring, which is
formed by Z.sub.4 together with C.sub.6, C.sub.4 and N includes
such as a pyridine ring, a pyridazine ring, a pyrimidine ring, a
pyrazine ring, a triazine ring, a benzoimidazole ring, an
oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole
ring, a thiazole ring, an indole ring, a benzothiazole ring, a
benzooxazole ring, a quinoxaline ring, a quinazoline ring, a
phthalazine ring, a carbazole ring, a carboline ring and a rings in
which at least one of carbon atoms of a hydrocarbon ring
constituting a carboline ring is substituted by a nitrogen atom.
Further, the aforesaid aromatic heterocyclic ring may be provided
with a substituent represented by each of R.sub.1 and R.sub.2 in
aforesaid Formula (13).
[0223] In Formula (14), a substituent each independently
represented by R.sub.3 and R.sub.4 is identical with a substituent
each independently represented by R.sub.1 and R.sub.2 in aforesaid
Formula (13).
[0224] In Formula (14), M.sub.11 is an element of the VIII group
belonging to the 8th-10th groups of the periodic table, and
preferably utilized are platinum (Pt) and iridium (Ir). Further, in
Formula (14), M.sub.11 may be either a metal or an ion.
[0225] <Metal Complex Having Formula (15) or Tautomer Thereof as
Partial Structure>
[0226] A metal complex according to the present invention, which is
provided with Formula (15) or a tautomer thereof as a partial
structure, will now be explained.
[0227] In Formula (15), a substituent each independently
represented by R.sub.5 and R.sub.6 is identical with a substituent
each independently represented by R.sub.1 and R.sub.2 in aforesaid
Formula (13).
[0228] In Formula (15), at least one of substituents represented by
R.sub.5 and R.sub.6 is an aromatic hydrocarbon group or an aromatic
heterocyclic group.
[0229] In Formula (15), an element represented by M.sub.12
belonging to the 8th-10th groups of the periodic table is identical
with an element represented by M.sub.11 belonging to the 8th-10th
groups of the periodic table in Formula (14).
[0230] <Metal Complex Having Ligand Represented by Formula
(16)>
[0231] A metal complex having a ligand represented by Formula (16)
will now be explained.
[0232] In Formula (16), an aromatic hydrocarbon ring each
independently formed by Z.sub.5 together with C.sub.8, X.sub.3 and
X.sub.5, Z.sub.6 together with C.sub.9, X.sub.4 and X.sub.6,
Z.sub.7 together with C.sub.10 and C.sub.11, and Z.sub.8 together
with C.sub.12 and C.sub.13, is identical with an aromatic
hydrocarbon ring formed by Z.sub.1 together with C.sub.1, X.sub.1
and X.sub.3 in aforesaid Formula (13).
[0233] In Formula (16), an aromatic heterocyclic ring independently
each formed by Z.sub.5 together with C.sub.8, X.sub.3 and X.sub.5,
Z.sub.6 together with C.sub.9, X.sub.4 and X.sub.6, Z.sub.7
together with C.sub.10 and C.sub.11, and Z.sub.8 together with
C.sub.12 and C.sub.13, is identical with an aromatic heterocyclic
ring formed by Z.sub.1 together with C.sub.1, X.sub.1 and X.sub.3
in aforesaid Formula (13).
[0234] <Metal Complex Having Partial Structure Represented by
Formula (17)>
[0235] A metal complex having a partial structure represented by
Formula (17) will now be explained.
[0236] In Formula (17), an aromatic hydrocarbon ring each
independently formed by Z.sub.9 together with C.sub.16, C.sub.14
and C.sub.18, Z.sub.11 together with C.sub.19 and C.sub.20, and
Z.sub.12 together with C.sub.21 and C.sub.22, is identical with an
aromatic hydrocarbon ring formed by Z.sub.1 together with C.sub.1,
X.sub.1 and X.sub.3 in aforesaid Formula (13).
[0237] In Formula (17), an aromatic heterocyclic ring each
independently formed by Z.sub.9 together with C.sub.16, C.sub.14
and C.sub.18, Z11 together with C.sub.19 and C.sub.20, and Z.sub.12
together with C.sub.21 and C.sub.22, is identical with an aromatic
heterocyclic ring formed by Z.sub.1 together with C.sub.1, X.sub.1
and X.sub.3 in aforesaid Formula (13).
[0238] In Formula (17), an aromatic heterocyclic ring formed by
Z.sub.10 together with C.sub.17, C.sub.15 and N is identical with
an aromatic heterocyclic ring formed by Z.sub.4 together with
C.sub.6, C.sub.4 and N in Formula (14).
[0239] In Formula (17), an element represented by M.sub.21
belonging to the 8th-10th groups of the periodic table is identical
with an element represented by M.sub.11 belonging to the 8th-10th
groups of the periodic table in Formula (14).
[0240] <Metal Complex Having Partial Structure Represented by
Formula (18)>
[0241] A metal complex having a partial structure represented by
Formula (18) will now be explained.
[0242] In Formula (18), an aromatic hydrocarbon ring each formed by
Z.sub.13 together with C.sub.23 and C.sub.24, and Z.sub.14 together
with C.sub.25 and C.sub.26, is identical with an aromatic
hydrocarbon ring formed by Z.sub.1 together with C.sub.1, X.sub.1
and X.sub.3 in aforesaid Formula (13).
[0243] In Formula (18), an aromatic hydrocarbon ring each
independently formed by Z.sub.13 together with C.sub.23 and
C.sub.24, and Z14 together with C.sub.25 and C.sub.26, is identical
with an aromatic hydrocarbon ring formed by Z.sub.1 together with
C.sub.1, X.sub.1 and X.sub.3 in aforesaid Formula (13).
[0244] In Formula (18), a substituent each independently
represented by R.sub.9 and R.sub.10 is identical with a substituent
each independently represented by R.sub.1 and R.sub.2 in aforesaid
Formula (13).
[0245] In Formula (18), an element represented by M.sub.22
belonging to the 8th-10th groups of the periodic table is identical
with an element represented by M.sub.11 belonging to the 8th-10th
groups of the periodic table in Formula (14).
[0246] In the following, specific examples of a metal complex
having a ligand represented by Formula (13), a metal complex having
a partial structure represented by Formula (14), a metal complex
having a partial structure represented by Formula (15) or a
tautomer thereof as a partial structure, a metal complex having a
ligand represented by Formula (16), a metal complex having a
partial structure represented by Formula (17), or a metal complex
having a partial structure represented by Formula (18) will be
listed, however, the present invention is not limited thereto.
##STR186## ##STR187## ##STR188## ##STR189## ##STR190## ##STR191##
##STR192## ##STR193## ##STR194## ##STR195## ##STR196## ##STR197##
##STR198## ##STR199## ##STR200## ##STR201## ##STR202## ##STR203##
##STR204## ##STR205## ##STR206## ##STR207## ##STR208## ##STR209##
##STR210## ##STR211## ##STR212## ##STR213## ##STR214## ##STR215##
##STR216## ##STR217## ##STR218## ##STR219## ##STR220## ##STR221##
##STR222##
EMBODIMENT (f)
[0247] The case in which at least one type of a platinum complex
selected from a group comprised of following Formula (19)-(27) as
the aforesaid blue light emitting ortho metalated complex.
[0248] <Platinum Complex Represented by Formula (19)>
[0249] A platinum complex represented by Formula (19) according to
the present invention will now be explained. In the present
invention, those represented by a tautomer of said Formula (19) are
also included.
[0250] In Formula (19), a substituent each independently
represented by R.sub.1 and R.sub.2 includes, for example, an alkyl
group (such as a methyl group, an ethyl group, an isopropyl group,
a hydroxyethyl group, a methoxymethyl group, a trifluoromethyl
group and a t-butyl group), a cycloalkyl group (such as a
cyclopentyl group and a cyclohexyl group), an aralkyl group (such
as a benzyl group and a 2-phenetyl group), an aryl group (such as a
phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl
group, a xylyl group, a biphenylyl group, a naphtyl group, an
anthoryl group and a phenanthryl group), an aromatic heterocyclic
group (such as a furyl group, a thienyl group, a pyridyl group, a
pyridazinyl group, a pyrimidinyl group, a pyradinyl group, a
triazinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, a quinazolynyl group, a carbazolyl group and a
phthalazinyl), an alkoxyl group (such as a methoxy group, an ethoxy
group, an isopropoxy group and a butoxy group), an aryloxy group
(such as a phenoxy group and a naphthyloxy group), a cyano group, a
hydroxyl group, an alkenyl group (such as a vinyl group), a styryl
group, a halogen atom (such as a chlorine atom, a bromine atom, an
iodine atom and a fluorine atom). These groups may be further
substituted.
[0251] In Formula (19), an aromatic hydrocarbon ring or an aromatic
heterocyclic ring includes, for example, a benzene ring, a
naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine
ring, a pyrazine ring, a triadine ring, a furan ring, a thiophen
ring, a pyrol ring, an imidazole ring, a pyrazole ring, a triazole
ring and a tetrazole ring. Preferable among them is a benzene
ring.
[0252] In Formula (19), an aromatic hydrocarbon ring or an aromatic
heterocyclic ring formed by Z.sub.4 together with C.sub.6, C.sub.4
and N includes such as a pyridine ring, a pyridazine ring, a
pyrimidine ring, a pyrazine ring, a triazine ring, a benzoimidazole
ring, a benzothiazole ring, a benzooxazole ring, a quinazoline ring
and a phthalazine ring. Preferable among them is a pyridine
ring.
[0253] In Formula (19), n1 is an integer of 1 or 2, and L1 is a
bidentate ligand when n1 is 1. A bidentate ligand represented by L1
includes such as oxycarboxylic acid, oxyaldehyde and derivatives
thereof (such as salicic aldehyde and oxyacetophenonato), a dioxy
compound (such as biphenolato), diketones (such as acetylacetonato,
dibenzoylmethanate, diethylmalonato and ethylacetoacetato),
oxyquinones (such as pyromeconato, oxynaphtoqunonato and
oxyanthraquinonato), tropolones (such as troponato and
hinokitiolato), an N-oxide compound, aminocarboxylic acid and the
similar compounds (such as glycinato, alaninato, anthranilato and
picolinato), hydroxylamines (such as aminophenolato, ethanolaminato
and mercaptoethylaminato), oxines (such as 8-oxyquinolinato),
aldimines (such as salicylaldiminato), oxyoximes (such as
benzoinoximato and salicylaldoximato), an oxyazo compound (such as
oxyazobenzonato and phenylazonaphtholato), nitrosonaphthols (such
as .beta.-nitrosa-.alpha.-naphtholato), triazenes (such as
diazoaminobenzento), biurets (such as biuretato and a polypeptide
group), formazenes and ditizones (such as diphenylcarbazonato and
diphenylthiocarbazonato), biguanides (such as biguanidato) and
glyoximes (such as dimethylglyoximato).
[0254] In the following, Formulas and specific examples of a
bidentate ligand preferably utilized in the present invention will
be listed; however, the present invention is not limited thereto.
##STR223##
[0255] In the Formulas of bidentate ligands described above, Ra-Rv
each are an alkyl group (for example, a methyl group, an ethyl
group, an isopropyl group, a hydroxyethyl group, a methoxymethyl
group, a trifluoromethyl group and a t-butyl group) or a alkyl
halogenide group (for example, the aforesaid alkyl groups, at least
one of hydrogen atoms of which is substituted by such as a fluorine
atom, a chlorine atom, a bromine atom or a iodine atom).
[0256] In the Formulas of bidentate ligands described above,
Ara-Arc are an aryl group (such as a phenyl group, a p-chlorophenyl
group, a mesityl group, a tolyl group, a xylyl group, a biphenyl
group, a naphthyl group, an anthoryl group and phenanthoryl group)
or an aromatic heterocyclic group (such as a furyl group, a thienyl
group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a
pyradinyl group, a triazinyl group, an imidazolyl group, a
pyrazolyl group, a thiazolyl group, a quinazolynyl group, a
carbazolyl group, a carbolinyl group, a diazacarbazolyl group (a
diazacarbazolyl group refers to the aforesaid carbolinyl group, any
one of carbon atoms constituting a carboline ring of which is
substituted by a nitrogen atom) and a phthalazinyl group).
[0257] <Platinum Complex Represented by Formula (20)>
[0258] A platinum complex represented by Formula (20) according to
the present invention will now be explained.
[0259] In Formula (20), a substituent represented by each of
R.sub.3 and R.sub.4 is identical with a substituent represented by
each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0260] In Formula (20), a bidentate ligand represented by L2 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0261] <Platinum Complex Represented by Formula (21)>
[0262] A platinum complex represented by Formula (21) according to
the present invention will now be explained.
[0263] In Formula (21), a substituent represented by each of
R.sub.5 and R.sub.6 is identical with a substituent represented by
each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0264] In Formula (21), a bidentate ligand represented by L3 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0265] In Formula (21), an aromatic hydrocarbon ring formed by
Z.sub.3 together with C (a carbon atom) includes such as a benzene
ring, a biphenyl ring, a naphthalene ring, an azulene ring, an
anthrathene ring, a phenanthrene ring, a pyrene ring, a chrisene
ring, a naphthacene ring, a triphenylene ring, an o-terphenyl ring,
a m-terphenyl ring, a p-terphenyl ring, an acenaphtene ring, a
coronene ring, a fluorene ring, a fluoranthrene ring, a naphthacene
ring, a pentacene ring, a perylene ring, a pentaphene ring, a
picene ring, a pyrene ring, a pyranthrene ring and an anthraathrene
ring. Further, the aforesaid aromatic hydrocarbon ring may be
provided with a substituent represented by each of R.sub.1 and
R.sub.2 in aforesaid Formula (19).
[0266] In Formula (21), an aromatic heterocyclic ring formed by
Z.sub.3 together with C (a carbon atom) includes such as a furan
ring, a thiophene ring, a pyridine ring, a pyridazine ring, a
pyrimidine ring, a pyrazine ring, a triazine ring, a benzoimidazole
ring, an oxadiazole ring, a triazole ring, an imidazole ring, a
pyrazole ring, a thiazole ring, an indole ring, a benzoimidazole, a
benzothiazole ring, a benzooxazole ring, a quinoxaline ring, a
quinazoline ring, a phthalazine ring, a carbazole ring, a carboline
ring and a ring in which at least one of carbon atoms of
hydrocarbon ring constituting a carboline ring is substituted by a
nitrogen atom. Further, the aforesaid aromatic heterocyclic ring
may be provided with a substituent represented by each of R.sub.1
and R.sub.2 in aforesaid Formula (19).
<Platinum Complex Represented by Formula (22)>
[0267] A platinum complex represented by Formula (22) according to
the present invention will now be explained.
[0268] In Formula (22), a substituent represented by each of
R.sub.7-R.sub.13 is identical with a substituent represented by
each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0269] In Formula (22), a bidentate ligand represented by L4 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
<Platinum Complex Represented by Formula (23)>
[0270] A platinum complex represented by Formula (23) according to
the present invention will now be explained.
[0271] In Formula (23), a substituent represented by each of
R.sub.14 and R.sub.15 is identical with a substituent represented
by each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0272] In Formula (23), a bidentate ligand represented by L5 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0273] In Formula (23), an aromatic hydrocarbon ring formed by
Z.sub.4 together with C (a carbon atom) is identical with an
aromatic hydrocarbon ring formed by Z.sub.3 together with C (a
carbon atom) in aforesaid Formula (21).
[0274] In Formula (23), an aromatic heterocyclic ring formed by
Z.sub.4 together with C (a carbon atom) is identical with an
aromatic heterocyclic ring formed by Z.sub.3 together with C (a
carbon atom) in aforesaid Formula (21).
<Platinum Complex Represented by Formula (24)>
[0275] A platinum complex represented by Formula (24) according to
the present invention will now be explained.
[0276] In Formula (24), a substituent represented by each of
R.sub.16-R.sub.22 is identical with a substituent represented by
each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0277] In Formula (23), a bidentate ligand represented by L6 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
<Platinum Complex Represented by Formula (25)>
[0278] A platinum complex represented by Formula (25) according to
the present invention will now be explained.
[0279] In Formula (25), a substituent represented by each of
R.sub.23 and R.sub.24 is identical with a substituent represented
by each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0280] In Formula (25), a bidentate ligand represented by L7 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0281] In Formula (25), an aromatic heterocyclic ring, which is
formed by each of Z.sub.5 together with N includes such as a
pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine
ring, a triazine ring, a benzoimidazole ring, an oxadiazole ring, a
triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring,
an indole ring, a benzoimidazole, a benzothiazole ring, a
benzooxazole ring, a quinoxaline ring, a quinazoline ring, a
phthalazine ring, a carbazole ring, a carboline ring and a ring in
which at least one of carbon atoms of hydrocarbon ring constituting
a carboline ring is substituted by a nitrogen atom. Further, the
aforesaid aromatic heterocyclic ring may be provided with a
substituent represented by each of R.sub.1 and R.sub.2 in aforesaid
Formula (19).
<Platinum Complex Represented by Formula (26)>
[0282] A platinum complex represented by Formula (26) according to
the present invention will now be explained.
[0283] In Formula (26), a substituent represented by each of
R.sub.25 and R.sub.26 is identical with a substituent represented
by each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0284] In Formula (26), a bidentate ligand represented by L8 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0285] In Formula (26), an aromatic heterocyclic ring, which is
formed by each of Z.sub.6 together with N includes such as a
pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine
ring, a triazine ring, a benzoimidazole ring, an oxadiazole ring, a
triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring,
an indole ring, a benzoimidazole, a benzothiazole ring, a
benzooxazole ring, a quinoxaline ring, a quinazoline ring, a
phthalazine ring, a carbazole ring, a carboline ring and a ring in
which at least one of carbon atoms of hydrocarbon ring constituting
a carboline ring is substituted by a nitrogen atom. Further, the
aforesaid aromatic heterocyclic ring may be provided with a
substituent represented by each of R.sub.1 and R.sub.2 in aforesaid
Formula (19).
<Platinum Complex Represented by Formula (27)>
[0286] A platinum complex represented by Formula (27) according to
the present invention will now be explained.
[0287] In Formula (27), a substituent represented by each of
R.sub.27 and R.sub.28 is identical with a substituent represented
by each of R.sub.1 and R.sub.2 in aforesaid Formula (19).
[0288] In Formula (27), a bidentate ligand represented by L9 is
identical with a bidentate ligand represented by L1 in aforesaid
Formula (19).
[0289] In Formula (27), a 5-membered or 6-membered ring formed by
Z.sub.7 is identical with a 5-membered or 6-membered ring formed by
Z.sub.1 in Formula (19).
[0290] In Formula (27), a 5-membered or 6-membered ring formed by
Z.sub.8 is identical with a 5-membered or 6-membered ring formed by
Z.sub.2 in Formula (19).
[0291] In Formula (27), as a divalent connecting group represented
by L0, utilized can be a group containing a hetero atom (for
example, a divalent group containing a chalcogen atom such as --O--
and --S--, and --N(R)-- group, wherein R is a hydrogen atom or an
alkyl group and said alkyl group is an alkyl group described as a
substituent represented by each of R.sub.1 and R.sub.2 in aforesaid
Formula (19)) in addition to a hydrocarbon group such as an
alkylene group (such as an ethylene group, a trimethilene group, a
tetramethylene group, a propylene group, an ethylethylene group, a
pentaethylene group, a hexamethylene group,
2,2,4-trimethylhexamethylene group, a heptamethylene group, an
octamethylene group, a nonamethylene group, a decamethylene group,
an undecamethylene group, a dodecamethylene group, a cyclohexylene
group (such as 1,6-cyclohexanediyl group), a cyclopentylene group
(such as 1,5-cyclopentanediyl group)), an alkenylene group (such as
a vinylene group and a propenylene group), an alkynylene group
(such as an ethylenylene group and a 3-pentynylene group) and an
arylene group.
[0292] In the following, specific examples of a platinum complex
compound utilized as an organic EL element material of the present
invention will be listed; however, the present invention is not
limited thereto. Herein, in specific examples listed below, each
surrounding of an aryl group incapable of free rotation or an
aromatic heterocyclic group incapable of free rotation is indicated
by a dotted line.
[0293] <Aryl Group Incapable of Free Rotation, Aromatic
Heterocyclic Group Incapable of Free Rotation>
[0294] In the present invention, "an aryl group incapable of free
rotation or an aromatic heterocyclic group incapable of free
rotation" means a substituent in a bond of which is incapable of
free rotation due to steric hindrance.
[0295] Herein, as the state of being incapable of free rotation,
not only the case, in which free rotation is physically impossible
due to the aforesaid aryl group or aromatic heterocyclic group
being close to such as other substituents arranged in the
surrounding, but also the case, in which a bond rotation barrier
exists due to conformation energy with respect to a substituent
bonded through a bonding axis of an aryl group or a bonding axis of
an aromatic heterocyclic group, can be defined as an aryl group
incapable of free rotation or an aromatic heterocyclic group
incapable of free rotation.
[0296] Herein, conformation energy to produce a bond rotation
barrier is preferably not less than 25 kcal/mol.
[0297] Further, in the present invention, an aryl group or an
aromatic heterocyclic group each is preferably in the state of
being physically incapable of free rotation.
[0298] An aryl group utilizable as an aryl group incapable of free
rotation includes such as a phenyl group, a tolyl group, a xylyl
group, a biphenyl group, a naphthyl group, an anthryl group and a
phenanthryl group.
[0299] An aromatic heterocyclic group utilizable as an aromatic
heterocyclic group incapable of free rotation includes such as a
furyl group, a thienyl group, a pyridyl group, a pyridazynyl group,
an pyrimizinyl group, a prazinyl group, a triazinyl group, an
imidazolyl group, a pyrazolyl group, a thiazoliyl group, a
quinazolinyl group and a phthalazinyl group. ##STR224## ##STR225##
##STR226## ##STR227## ##STR228## ##STR229## ##STR230## ##STR231##
##STR232## ##STR233## ##STR234## ##STR235## ##STR236## ##STR237##
##STR238## ##STR239##
EMBODIMENT g
[0300] The case in which at least one type of a platinum complex
selected from a group comprising following Formulas (28)-(32) as
the aforesaid blue light emitting ortho metalated complex.
[0301] A metal complex compound provided with a specific structure,
which is represented by each of Formulas (28)-(32) according to the
present invention, will now be explained.
[0302] In Formula (28) described above, Z.sub.11 together with a
carbon atom and a nitrogen atom is an atomic group necessary to
form an aromatic heterocyclic ring; Z.sub.12 together with a carbon
atom is an atomic group necessary to form a non-aromatic ring; and
M is a metal. An aromatic heterocyclic group formed by Z.sub.11
includes such as a pyridine ring, a pyridazine ring, a pyrimidine
ring, a pyrazine ring, a triazine ring, a benzoimidazole ring, a
benzothiazole ring, a benzooxazole ring, a quinazoline ring and a
phthalazine ring. A non-aromatic ring formed by Z.sub.12 includes,
for example, the rings described below. ##STR240##
[0303] In Formula (28), a non-aromatic ring represented by Z.sub.12
is preferably R-2 or R-6.
[0304] Next, Formula (29) will be explained.
[0305] In Formula (29), each of Z.sub.21 and Z.sub.22, together
with a carbon atom and a nitrogen atom, is an atomic group
necessary to form an aromatic heterocyclic ring and M is a metal.
An aromatic ring formed by Z.sub.21 includes aromatic heterocyclic
rings similar to aforesaid Z.sub.11, and an aromatic heterocyclic
ring formed by Z.sub.22 includes such as a pyrrole ring, a pyrazole
ring, an imidazole ring, a triazole ring, an indole ring and a
benzoimidazole ring. Preferable are the case of a pyrrole ring or a
triazole ring.
[0306] Next, Formula (30) will be explained.
[0307] In Formula (30), Z.sub.31, together with a carbon atom and a
nitrogen atom, is an atomic group necessary to form an aromatic
heterocyclic ring; Z.sub.32, together with a carbon atom, is an
atomic group comprising a carbon, nitrogen or oxygen atom necessary
to form a 5-membered aromatic ring; and M is a metal. An aromatic
heterocyclic ring formed by Z.sub.31 includes aromatic heterocyclic
rings similar to aforesaid Z.sub.11, and a 5-membered aromatic ring
formed by Z.sub.32 includes such as a pyrrole ring, a furan ring,
an imidazole ring, a pyrazole ring, an oxazole ring and an
oxadizole ring. Preferable is a nitrogen-containing aromatic
heterocyclic ring and more preferably is a nitrogen-containing
aromatic heterocyclic ring having a plural number of nitrogen atoms
or an oxygen atoms.
[0308] Next, Formula (31) will be explained.
[0309] In Formula (31), Z.sub.41, together with a carbon atom and a
nitrogen atom, is an atomic group necessary to form an aromatic
heterocyclic ring; Z.sub.42, together with a carbon atom, is an
atomic group necessary to form a ring; and M is a metal. An
aromatic heterocyclic ring formed by Z.sub.31 includes aromatic
heterocyclic rings similar to an aromatic heterocyclic group
similar to aforesaid Z.sub.11; and a ring formed by Z.sub.42 may be
either an aromatic ring or a non-aromatic ring, however, is
preferably a non-aromatic ring.
[0310] Next, Formula (32) will be explained.
[0311] In Formula (32), Z.sub.51, together with a carbon atom and a
nitrogen atom, is an atomic group necessary to form an aromatic
heterocyclic ring; Z.sub.52, together with a carbon atom, is an
atomic group necessary to form an azulene ring; and M is a metal.
An aromatic heterocyclic ring formed by Z.sub.51 includes aromatic
heterocyclic rings similar to aforesaid Z.sub.11.
[0312] In Formulas (28)-(32) explained above, a ring formed by
Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, Z.sub.32,
Z.sub.41, Z.sub.42, Z.sub.51 and Z.sub.52 may be further provided
with a substituent, and the substituents may bond to each other to
further form a ring. Further, in Formulas (28)-(32), M is
preferably a metal belonging to the 8th-10th groups of the periodic
table, more preferably iridium, osmium or platinum, and most
preferably iridium.
[0313] In the following, specific examples represented any one of
Formulas (28)-(32) will be listed, however, the present invention
is not limited thereto. ##STR241## ##STR242## ##STR243## ##STR244##
##STR245## ##STR246## ##STR247## ##STR248## ##STR249## ##STR250##
##STR251## ##STR252##
EMBODIMENT h
[0314] The case in which at least one type of a platinum complex
represented by following Formula (A) or (B) as the aforesaid blue
light emitting ortho metalated complex.
[0315] At least one type of a platinum complex represented by
following Formula (A) or (B) according to the present invention
will now be explained.
[0316] <Platinum Complex Having Ligand Represented by Formula
(A)>
[0317] A platinum complex having a partial structure represented by
Formula (A) according to the present invention will be
explained.
[0318] A platinum complex represented by Formula (A) according to
the present invention will be explained.
[0319] In Formula (A), a substituent represented by each of
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.2 and R.sub.7
includes, for example, an alkyl group (such as a methyl group, an
ethyl group, a propyl group, an isopropyl group, t-butyl group, a
pentyl group, a hexyl group, an octyl group, a dodecyl group, a
tridecyl group, a tetradecyl group and a pentadecyl group), a
cycloalkyl group (such as a cyclopentyl group and a cyclohexyl
group), an alkenyl group (such as a vinyl group and an allyl
group), an alkynyl group (such as a propargyl group), an aryl group
(such as a phenyl group, a tolyl group, a xylyl group, a naphthyl
group, a biphenylyl group, an anthoryl group, a phnathryl group, a
mesityl group and a fluorenyl group), a heterocyclic group (such as
a pyridyl group, a thiazolyl group, a oxazolyl group, an imidazolyl
group, a furyl group, a pyrrolyl group, a pyradinyl group, a
pyrimidinyl group, a pyridazinyl group, a selenazolyl group, a
sulforanyl group, a piperidinyl group, a pyrazolyl group, a
tetrazolyl group and a carbazolyl group), an alkoxyl group (such as
a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy
group, a hexyloxy group, an octyloxy group and a dodecyloxy group),
a cycloalkoxy group (such as cyclopentyloxy group and a
cyclohexyloxy group), an aryloxy group (such as a phenoxy group and
a naphthyloxy group), an alkylthio group (such as a methylthio
group, an ethylthio group, a propylthio group, a pentylthio group,
a hexylthio group, an octylthio group and a dodecylthio group), a
cycloalkylthio group (such as cyclopentylthio group and a
cyclohecylthio group), an arylthio group (such as a phenylthio
group and a naphthylthio group), alkoxycarbonyl group (such as a
methyloxycarbonyl group, an ethyloxycarbonyl group, a
butyloxycarbonyl group, an octyloxycarbonyl group and a
dodecyloxycarbonyl group), an aryloxycarbonyl group (such as a
phenyloxycarbonyl group and a naphthyloxycarbonyl group), a
sulfamoyl group (such as an aminosulfonyl group, a
methylaminosulfonyl group, a dimethylaminosulfonyl group, a
butylaminosulfonyl group, a hexylaminosulfonyl group, a
cyclohexylaminosulfonyl group, an octylaminosulfonyl group, a
dodecylaminosulfonyl group, a phenylaminosulfonyl group, a
naphthylaminosulfonyl group and a 2-pyridylaminosulfonyl group), an
ureido group (such as a methylureido, an ethylureido group, a
pentylureido group, a cyclohexylureido group, an octylureido group,
a dodecylureido group, a phenylureido group, a naphthylureido group
and a 2-pyridylaminoureido group), an acyl group (such as an acetyl
group, an ethylcarbonyl group, a propylcarbonyl group, a
pentylcarbonyl group, a cyclohexylcarbonyl group, an octylcarbonyl
group, a 2-ethylhexylcarbonyl group, a dodecylcarbonyl group, a
phenylcarbonyl group, a naphthylcarbonyl group and a
pyridylcarbonyl group), an acyloxy group (such as an acetyloxy
group, an ethylcarbonyloxy group, a butylcarbonyloxy group, an
octylcarbonyloxy group, a dodecylcarbonyloxy group and a
phenylcarbonyloxy group), an amido group (such as a
methylcarbonylamino group, an ethylcarbonylamino group, a
dimethylcarbonylamino group, a propylcarbonylamino group, a
pentylcarbonylamino group, a cyclohexylcarbonylamino group, a
2-ethylhexylcarbonylamino group, an octylcarbonylamino group, a
dodecylcarbonylamino group, a phenylcarbonylamino group and a
naphthylcarbonylamino group), a carbamoyl group (such as an
aminocarbonyl group, a methyaminocarbonyl group, a
dimethylaminocarbonyl group, a propylaminocarbonyl group, a
pentylaminocarbonyl group, a cyclohexylaminocarbonyl group, an
octylaminocarbonyl group, a 2-ethylhexylaminocarbonyl group, a
dodecylaminocarbonyl group, a phenylaminocarbonyl group, a
naphthylaminocarbonyl group and a 2-pyridylaminocarbonyl group), a
sulfinyl group (such as a methylsulfinyl group, an ethylsulfinyl
group, a butylsulfinyl group, a cyclohexylsulfinyl group, a
2-ethylhexylsulfinyl group, a dodecylsulfinyl group, a
phenylsulfinyl group, a naphthylsulfinyl group and a
2-pyridylsulfinyl group), an alkylsulfonyl group or an arylsulfonyl
group (such as a methylsulfonyl group, an ethylsulfonyl group, a
butylsulfonyl group, an cyclohexylsulfonyl group, a
2-ethylhexylsulfonyl group, a dodecylsulfonyl group, a
phenylsulfonyl group, a naphthylsulfonyl group and a
2-pyridylsulfonyl group), an amido group (an amino group, an
ethylamino group, a dimethylamino group, a butylamino group, a
cyclopentylamino group, a 2-ethylhexylamino group, a dodcylamino
group, an anilino group, a naphthylamino group and a 2-pyridyl
amino group), a nitro group, a cyano group, a silyl group (such as
a trimethylsilyl group, a t-butylmethylsilyl group, a
dimethylphenylsilyl group and a triphenylsilyl group).
[0320] In the present invention, at least one of groups represented
by R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is preferably an electron
donating group; it is more preferable that at least two of
aforesaid groups represented by R.sub.1, R.sub.2, R.sub.3 and
R.sub.4 are electron donating groups and .sigma.p of at least one
of said electron donating groups is not more than -0.20; and it is
most preferable that the aforesaid electron donating group is
introduced to R.sub.2 or R.sub.4 of Formula (A).
[0321] <Electron Donating Group Having up of Not More Than
-0.20>
[0322] Herein, an electron donating group having 6p of not more
than -0.20 includes such as a cyclopropyl group (-0.21), a
cyclohexyl group (-0.22), a tert-butyl group (-0.20),
--CH.sub.2Si(CH.sub.3).sub.3 (-0.21), an amino group (-0.66), a
hydroxylamino group (-0.34), --NHNH.sub.2 (-0.55), --NHCONH.sub.2
(-0.24), --NHCH.sub.3 (-0.84), --NHC.sub.2H.sub.5 (-0.61),
--NHCONHC.sub.2H.sub.5 (-0.26), --NHC.sub.4H.sub.9 (-0.51),
--NHC.sub.6H.sub.5 (-0.40), --N.dbd.CHC.sub.6H.sub.5 (-0.55), --OH
(-0.37), --OCH.sub.3 (-0.27), --OCH.sub.2COOH (-0.33),
--OC.sub.2H.sub.5 (-0.24), --OC.sub.3H.sub.7 (-0.25),
--OCH(CH.sub.3).sub.2 (-0.45), --OC.sub.5H.sub.11 (-0.34) and
--OCH.sub.2C.sub.6H.sub.5 (-0.42), however, the present invention
is not limited thereto.
[0323] In Formula (A), a substituent represented by each of Ra and
Rb is identical with a substituent represented by each of R.sub.1,
R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 in Formula
(A), however, preferable is the case in which both Ra and Rb are
alkyl groups.
[0324] <Platinum Complex Having Ligand Represented by Formula
(B)>
[0325] A platinum complex having a partial structure represented by
Formula (B) will now be explained.
[0326] A platinum complex represented by Formula (B) will now be
explained.
[0327] In Formula (B), a substituent represented by each of
R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and
R.sub.17 is identical with a substituent represented by each of
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 in
Formula (1). Herein, at least one of R.sub.11 and R.sub.12 is an
electron attracting group; the both of R.sub.11 and R.sub.12 are
preferably electron attracting groups, and it is furthermore
preferable that 6p of the aforesaid electron attracting group is
not less than 0.10.
[0328] <Electron Attracting Group Having .sigma.p of not Less
than 0.10>
[0329] An electron attracting group having 6p of not less than 0.10
includes such as --B(OH).sub.2 (0.12), bromine atom (0.23),
chlorine atom (0.23), iodine atom (0.18), --CBr.sub.3 (0.29),
--CCl.sub.3 (0.33), --CCF.sub.3 (0.54), --CN (0.66), --CHO (0.42),
--COOH (0.45), --CONH.sub.2 (0.36), --CH.sub.2SO.sub.2CF.sub.3
(0.31), --COCH.sub.3 (0.45), 3-varenyl group (0.19),
--CF(CF.sub.3).sub.2 (0.53), --CO.sub.2C.sub.2H.sub.5 (0.45),
--CF.sub.2CF.sub.2CF.sub.2CF.sub.3 (0.52), --C.sub.6F.sub.5 (0.41),
2-benzooxazolyl group (0.33), 2-benzothiazolyl group (0.29),
--C.dbd.O(C.sub.6H.sub.5) (0.43), --OCF.sub.3 (0.35),
--CSO.sub.2CH.sub.3 (0.36), --SO.sub.2(CH.sub.2) (0.57),
--SO.sub.2CH.sub.3 (0.72), --COCH.sub.2CH.sub.3 (0.48),
--COCH(CH.sub.3).sub.2 (0.47) and --COC(CH.sub.3).sub.3 (0.32),
however, the present invention is not limited thereto.
[0330] In Formula (B), a substituent represented by each of Rc and
Rd is identical with a substituent represented by each of R.sub.1,
R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 in Formula
(1), however, the both of Rc and Rd are preferably alkyl
groups.
[0331] In the following, specific examples of a platinum complex
having a partial structure represented by Formula (A) or (B)
according to the present invention will be listed; however, the
present invention is not limited thereto. ##STR253## ##STR254##
##STR255## ##STR256## ##STR257## ##STR258## ##STR259## ##STR260##
##STR261## ##STR262## ##STR263## ##STR264## ##STR265## ##STR266##
##STR267## ##STR268##
[0332] Metal complexes according to an organic EL element of the
present invention (specifically, ortho metalated complexes of each
of green, blue and red) can be synthesized by applying a method
described, for example, in Organic Letter, vol. 13, No. 16, pp.
2579-2581 (2001), Inorganic Chemistry, vol. 30, No. 8, pp.
1685-1687 (1991), J. Am. Chem. Soc., vol. 123, p. 4304 (2001),
Inorganic Chemistry, vol. 40, No. 7, pp. 1704-1711 (2001),
Inorganic Chemistry, vol. 41, No. 12, pp. 3055-3066 (2002), and New
Journal of Chemistry, vol. 26, p. 1171 (2002); and further in
references described in these literatures.
[0333] <Application of Organic EL Element Material Containing
Metal Complex to Organic EL Element>
[0334] In the case of preparing an organic EL element by utilizing
a phosphorescent compound according to the present invention, said
phosphorescient compound is preferably utilized in an emission
layer or a positive hole blocking layer among the constituent
layers of an organic EL element (details of which will be described
later). Further, in an emission layer, said phosphorescent compound
is preferably utilized as an emission dopant.
[0335] (Emission Host and Emission Dopant)
[0336] The mixing ratio of an emission dopant against an emission
host, which is a host compound as a primary component in an
emission layer, is preferably adjusted in a range of not less than
0.1 weight % and less than 30 weight %.
[0337] Herein, plural types of compounds may be mixed to be
utilized as an emission dopant, and the partner to be mixed may be
another metal complex having a different structure, a
phosphorescent dopant or a fluorescent dopant having another
structure.
[0338] An embodiment wherein a phosphorescence emitting compound
according to the present invention is preferably utilized includes
the following embodiments.
[0339] (a) The case in which at least two types of phosphorescence
emitting compounds different from each other are contained in the
same emission layer.
[0340] (b) The case in which at least two types of phosphorescence
emitting compounds different from each other are contained in
different emission layers, respectively.
[0341] (b) The case in which two types out of three types of
phosphorescence emitting compounds different from each other are
contained in the same emission layer and the remaining one type is
contained in an emission layer different from the emission layer in
which aforesaid two types are contained.
[0342] Further, a dopant (such as a phosphorescent dopant and a
fluorescent dopant) utilizable in combination with a
phosphorescence emitting compound according to the present
invention, which is utilized as an emission dopant, will be
explained.
[0343] An emission dopant is roughly classified into tow types, a
fluorescent dopant which emits fluorescence and a phosphorescent
dopant which emits phosphorescence.
[0344] A typical example of the former (a fluorescent dopant)
includes such as cumarin type dye, pyran type dye, cyanine type
dye, croconium type dye, squalium type dye, oxobenzanthrathene type
dye, fluoresceine type dye, Rhodamine type dye, pyrylium type dye,
perillene type dye, stylben type dye, polythiophene type dye or a
rare earth complex type fluorescent substance.
[0345] A typical example of the latter (a phosphorescent dopant) is
preferably a complex type compound containing a metal belonging to
the 8th, 9th or 10th group of the periodic table, more preferably
an iridium compound and an osmium compound and most preferably an
iridium compound.
[0346] Specifically, these are compounds described in the following
patent publications:
[0347] Such as WO 00/70655 pamphlet; JP-A Nos. 2002-280178,
2001-181616, 2002-280179, 2001-181617, 2002-280180, 2001-247859,
2002-299060, 2001-313178, 2002-302671, 2001-345183 and 2002-324679;
WO 02/15645 pamphlet; JP-A Nos. 2002-332291, 2002-50484,
2002-332292, 2002-83684, 2002-540572, 2002-117978, 2002-338588,
2002-170684 and 2002-352960; WO 01/93642 pamphlet, JP-A Nos.
2002-50483, 2002-100476, 2002-173674, 2002-359082, 2002-175884,
2002-363552, 2002-184582 and 2003-7469; Japanese Translation of PCT
International Application Publication No. 2002-525808; JP-A
2003-7471; Japanese Translation of PCT International Application
Publication No. 2002-525833; JP-A Nos. 2003-31366, 2002-226495,
2002-234894, 2002-235076, 2002-241751, 2001-319779, 2001-319780,
2002-62824, 2002-100474, 2002-203679, 2002-343572 and
2002-203678.
[0348] Compounds which can be utilized in combination with a
phosphorescence emitting compound according to the present
invention will be partly listed below. ##STR269## ##STR270##
[0349] (Emission Host)
[0350] An emission host means a compound a mixing ratio (weight) of
which is largest in an emission layer comprising at least two types
of compounds, and other compounds are called as dopant compounds
(or simply as dopants). For example, when an emission layer is
comprised of two types, compound A and compound B, and the mixing
ratio A/B=10/90, compound A is a dopant compound and compound B is
a host compound. Further, when an emission layer is comprised of
three types, compound A, compound B and compound C, and the mixing
ratio A/B/C=5/10/85, compound A and compound B are dopant compounds
and compound C is a host compound.
[0351] An emission host utilized in the present invention is not
specifically limited with respect to the structure, however,
typically includes those having a basic skeleton of such as a
carbazole derivative, a triarylamine derivative, an aromatic borane
derivative, a nitrogen-containing heterocyclic compound, a
thiophene derivative, a furan derivative and oligoarylene compound,
or such as a carboline derivative and a diazacarbazole derivative
(wherein, a diazacarbazole derivative is those at least one carbon
atom of a hydrocarbon ring, which constitutes a carboline ring of a
carboline derivative, is substituted by a nitrogen atom).
[0352] Among them, preferably utilized are such as a carboline
derivative, a diazacarbazole derivative and a compound represented
by above-described Formula (33).
[0353] <Compound Represented by Formula (33)>
[0354] A compound represented by Formula (33) according to the
present invention will now be explained.
[0355] The inventors of the present invention, as a result of
extensive study, have found that an organic EL element, which is
prepared by containing a compound represented by aforesaid Formula
(33) in an emission layer or in an adjacent layer to said emission
layer and utilizing a phosphorescence emitting compound described
later in an emission layer, exhibits increased emission efficiency
and prolonged life.
[0356] In aforesaid Formula (33), Z.sub.1 is an aromatic
heterocyclic ring which may be provided with a substituent; Z.sub.2
is an aromatic heterocyclic ring or an aromatic hydrocarbon ring
which may be provided with a substituent; and Z.sub.3 is a divalent
connecting group or a simple bonding hand. R.sub.101 is a hydrogen
atom or a substituent.
[0357] In aforesaid Formula (33), an aromatic heterocyclic ring
represented by Z.sub.1 and Z.sub.2 includes such as a furan ring, a
thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine
ring, a pyradine ring, a triazine ring, a benzoimidazole ring, an
oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole
ring, a thiazole ring, an indole ring, a benzoimidazole ring, a
benzothiazole ring, a benzooxazole ring, a quinoxaline ring, a
quinazoline ring, a phthalazine ring, a carbazole ring, a carboline
ring and a ring in which a carbon atom of a hydrocarbon ring
constituting a carboline ring is further substituted by a nitrogen
atom. Further, the aforesaid aromatic heterocyclic ring may be
provided with a substituent represented by R.sub.101, which will be
described later.
[0358] In aforesaid Formula (33), an aromatic hydrocarbon ring
represented by Z.sub.2 includes such as a benzene ring, a biphenyl
ring, a naphthalene ring, an azulene ring, an anthrathene ring, a
phenanthrene ring, a pyrene ring, a chrisene ring, a naphthacene
ring, a triphenylene ring, an o-terphenyl ring, a m-terphenyl ring,
a p-terphenyl ring, an acenaphtene ring, a coronene ring, a
fluorene ring, a fluoranthrene ring, a naphthacene ring, a
pentacene ring, a perylene ring, a pentaphene ring, a picene ring,
a pyrene ring, a pyranthrene ring and an anthraathrene ring.
Further, the aforesaid aromatic hydrocarbon ring may be provided
with a substituent represented by R.sub.101 which will be described
later.
[0359] In Formula (33), a substituent represented by R.sub.11
includes such as an alkyl group (such as a methyl group, an ethyl
group, a propyl group, an isopropyl group, t-butyl group, a pentyl
group, a hexyl group, an octyl group, a dodecyl group, a tridecyl
group, a tetradecyl group and a pentadecyl group), a cycloalkyl
group (such as a cyclopentyl group and a cyclohexyl group), an
alkenyl group (such as a vinyl group and an allyl group), an
alkynyl group (such as a ethynyl group and a propargyl group), an
aryl group (such as a phenyl group and a naphthyl group), an
aromatic heterocyclic group (such as a furyl group, a thienyl
group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a
pyradinyl group, a triazinyl group, an imidazolyl group, a
pyrazolyl group, a thiazolyl group, a quinazolyl group and a
phthalazinyl group), a heterocyclic group (such as a pyrrolidyl
group, an imidazolidyl group, a morpholyl group and a oxazolidyl
group), an alkoxyl group (such as a methoxy group, an ethoxy group,
a propyloxy group, a pentyloxy group, a hexyloxy group, an octyloxy
group and a dodecyloxy group), a cycloalkoxy group (such as
cyclopentyloxy group and a cyclohexyloxy group), an aryloxy group
(such as a phenoxy group and a naphthyloxy group), an alkylthio
group (such as a methylthio group, an ethylthio group, a propylthio
group, a pentylthio group, a hexylthio group, an octylthio group
and a dodecylthio group), a cycloalkylthio group (such as
cyclopentylthio group and a cyclohecylthio group), an arylthio
group (such as a phenylthio group and a naphthylthio group),
alkoxycarbonyl group (such as a methyloxycarbonyl group, an
ethyloxycarbonyl group, a butyloxycarbonyl group, an
octyloxycarbonyl group and a dodecyloxycarbonyl group), an
aryloxycarbonyl group (such as a phenyloxycarbonyl group and a
naphthyloxycarbonyl group), a sulfamoyl group (such as an
aminosulfonyl group, a methylaminosulfonyl group, a
dimethylaminosulfonyl group, a butylaminosulfonyl group, a
hexylaminosulfonyl group, a cyclohexylaminosulfonyl group, an
octylaminosulfonyl group, a dodecylaminosulfonyl group, a
phenylaminosulfonyl group, a naphthylaminosulfonyl group and a
2-pyridylaminosulfonyl group), an acyl group (such as an acetyl
group, an ethylcarbonyl group, a propylcarbonyl group, a
pentylcarbonyl group, a cyclohexylcarbonyl group, an octylcarbonyl
group, a 2-ethylhexylcarbonyl group, a dodecylcarbonyl group, a
phenylcarbonyl group, a naphthylcarbonyl group and a
pyridylcarbonyl group), an acyloxy group (such as an acetyloxy
group, an ethylcarbonyloxy group, a butylcarbonyloxy group, an
octylcarbonyloxy group, a dodecylcarbonyloxy group and a
phenylcarbonyloxy group), an amido group (such as a
methylcarbonylamino group, an ethylcarbonylamino group, a
dimethylcarbonylamino group, a propylcarbonylamino group, a
pentylcarbonylamino group, a cyclohexylcarbonylamino group, a
2-ethylhexylcarbonylamino group, an octylcarbonylamino group, a
dodecylcarbonylamino group, a phenylcarbonylamino group and a
naphthylcarbonylamino group), a carbamoyl group (such as an
aminocarbonyl group, a methyaminocarbonyl group, a
dimethylaminocarbonyl group, a propylaminocarbonyl group, a
pentylaminocarbonyl group, a cyclohexylaminocarbonyl group, an
octylaminocarbonyl group, a 2-ethylhexylaminocarbonyl group, a
dodecylaminocarbonyl group, a phenylaminocarbonyl group, a
naphthylaminocarbonyl group and a 2-pyridylaminocarbonyl group), an
ureido group (such as a methylureido group, an ethylureido group, a
pentyl ureido group, a cyclohexylureido group, an octylureido
group, a dodecylureido group, a phenylureido group, a
naphthylureido group and a 2-pyridylureido group), a sulfinyl group
(such as a methylsulfinyl group, an ethylsulfinyl group, a
butylsulfinyl group, a cyclohexylsulfinyl group, a
2-ethylhexylsulfinyl group, a dodecylsulfinyl group, a
phenylsulfinyl group, a naphthylsulfinyl group and a
2-pyridylsulfinyl group), an alkylsulfonyl group (such as a
methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl
group, an cyclohexylsulfonyl group, a 2-ethylhexylsulfonyl group
and a dodecylsulfonyl group), an arylsulfonyl group (such as a
phenylsulfonyl group, a naphthylsulfonyl group and a
2-pyridylsulfonyl group), an amino group (an amino group, an
ethylamino group, a dimethylamino group, a butylamino group, a
cyclopentylamino group, a 2-ethylhexylamino group, a dodcylamino
group, an anilino group, a naphthylamino group and a 2-pyuridyl
amino group), a halogen atom (such as a fluorine atom, a chlorine
atom and a bromine atom), a fluorohydrocarbon group (such as a
fluoromethyl group, trifluoromethyl group, pentafluoroethyl group
and pentafluorophenyl group), a cyano group, a nitro group, a
hydroxyl group, a mercapto group, a silyl group (such as
trimethylsilyl group, t-isopropylsilyl group and a triphenylsilyl
group).
[0360] These substituents may be further substituted by the
above-described substituents. Further, a plural number of these
substituents may bond to each other to form a ring.
[0361] Preferable substituents are an alkyl group, a cycloalkyl
group, a fluorohydrocarbon group, an aryl group and an aromatic
heterocyclic group.
[0362] A divalent connecting group may be those containing a hetero
atom in addition to a hydrocarbon group such as alkylene,
alkenylene, alkynylene and arylene; also may be those arising from
a compound having an aromatic heterocyclic ring (also referred to
as a hetero aromatic compound) such as a thiophene-2,5-diyl group
and a pyridine-2,3-diyl group; and may be a chalcogen atom such as
oxygen and sulfur. Further, a divalent connecting group may be a
group, which bonds via a hetero atom, such as an alkylimino group,
a dialkylsilanediyl group and a diarylgermandiyl.
[0363] A simple bonding hand is a bonding hand to directly connect
substituents to be combined with each other.
[0364] In the present invention, Z.sub.1 of aforesaid Formula (33)
is preferably a 6-membered ring. Thereby, higher emission
efficiency can be obtained and the life is further prolonged.
[0365] Further, in the present invention, Z.sub.2 of aforesaid
Formula (33) is preferably a 6-membered ring. Thereby, higher
emission efficiency can be obtained and the life is further
prolonged.
[0366] Further, it is preferable to make the both Z.sub.1 and
Z.sub.2 of aforesaid Formula (33) be a 6-membered ring, because
furthermore high emission efficiency can be obtained. Further, it
is preferable because the life is furthermore prolonged.
[0367] A compound represented by aforesaid Formula (33) is
preferably a compound represented by each of aforesaid Formula
(33-1)-(33-13).
[0368] In aforesaid Formula (33-1), R.sub.501-R.sub.507 each
independently are a hydrogen atom or a substituent.
[0369] By utilizing a compound represented by aforesaid Formula
(33-1), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0370] In aforesaid Formula (33-2), R.sub.511-R.sub.517 each
independently are a hydrogen atom or a substituent.
[0371] By utilizing a compound represented by aforesaid Formula
(33-2), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0372] In aforesaid Formula (33-3), R.sub.521-R.sub.527 each
independently are a hydrogen atom or a substituent.
[0373] By utilizing a compound represented by aforesaid Formula
(33-3), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0374] In aforesaid Formula (33-4), R.sub.531-R.sub.537 each
independently are a hydrogen atom or a substituent.
[0375] By utilizing a compound represented by aforesaid Formula
(33-4), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0376] In aforesaid Formula (33-5), R.sub.541-R.sub.548 each
independently are a hydrogen atom or a substituent.
[0377] By utilizing a compound represented by aforesaid Formula
(33-5), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0378] In aforesaid Formula (33-6), R.sub.551-R.sub.558 each
independently are a hydrogen atom or a substituent.
[0379] By utilizing a compound represented by aforesaid Formula
(33-6), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0380] In aforesaid Formula (33-7), R.sub.561-R.sub.567 each
independently are a hydrogen atom or a substituent.
[0381] By utilizing a compound represented by aforesaid Formula
(33-7), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0382] In aforesaid Formula (33-8), R.sub.571-R.sub.577 each
independently are a hydrogen atom or a substituent.
[0383] By utilizing a compound represented by aforesaid Formula
(33-8), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0384] In aforesaid Formula (33-9), R.sub.581-R.sub.588 each
independently are a hydrogen atom or a substituent.
[0385] By utilizing a compound represented by aforesaid Formula
(33-9), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0386] In aforesaid Formula (33-10), R.sub.591-R.sub.598 each
independently are a hydrogen atom or a substituent.
[0387] By utilizing a compound represented by aforesaid Formula
(33-10), an organic EL element having higher emission efficiency
can be prepared. Further, the life of the organic EL element can be
prolonged.
[0388] Further, a compound represented by aforesaid Formula (33) is
preferably a compound having at least one group represented by any
one of aforesaid Formulas (3-1)-(3-10). In particular, it is
preferable that 2-4 of groups represented by any one of aforesaid
Formulas (34-1)-(34-10) are provided in a molecule. Herein,
included is the case wherein, in a structure represented by
aforesaid Formula (33), the part except R.sub.101 is substituted by
any one of aforesaid Formulas (34-1)-(34-10).
[0389] Herein, a compound represented by aforesaid Formula
(35)-(49) is specifically preferable with respect to obtaining an
effect of the present invention.
[0390] In aforesaid Formula (35), R.sub.601-R.sub.606 are a
hydrogen atom or a substituent, however, at least one of
R.sub.601-R.sub.606 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0391] By utilizing a compound represented by aforesaid Formula
(35), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0392] In aforesaid Formula (36), R.sub.611-R.sub.620 are a
hydrogen atom or a substituent, however, at least one of
R.sub.611-R.sub.620 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0393] By utilizing a compound represented by aforesaid Formula
(36), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0394] In aforesaid Formula (37), R.sub.621-R.sub.623 are a
hydrogen atom or a substituent, however, at least one of
R.sub.621-R.sub.623 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0395] By utilizing a compound represented by aforesaid Formula
(37), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0396] In aforesaid Formula (38), R.sub.631-R.sub.645 are a
hydrogen atom or a substituent, however, at least one of
R.sub.631-R.sub.645 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0397] By utilizing a compound represented by aforesaid Formula
(38), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0398] In aforesaid Formula (39), R.sub.651-R.sub.656 are a
hydrogen atom or a substituent, however at least one of
R.sub.651-R.sub.656 is a group represented by any one of aforesaid
Formula (34-1)-(34-10). na is an integer of 0-5 and nb is an
integer of 1-6, however, the sum of na and nb is 6.
[0399] By utilizing a compound represented by aforesaid Formula
(39), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0400] In aforesaid Formula (40), R.sub.661-R.sub.672 are a
hydrogen atom or a substituent, however, at least one of
R.sub.661-R.sub.672 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0401] By utilizing a compound represented by aforesaid Formula
(40), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0402] In aforesaid Formula (41), R.sub.681-R.sub.688 are a
hydrogen atom or a substituent, however, at least one of
R.sub.681-R.sub.688 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0403] By utilizing a compound represented by aforesaid Formula
(41), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0404] In aforesaid Formula (42), R.sub.691-R.sub.700 are a
hydrogen atom or a substituent, however, at least one of
R.sub.691-R.sub.700 is a group represented by any one of aforesaid
Formula (34-1)-(34-10).
[0405] In Formula (42), as a divalent connecting group represented
by L.sub.1, utilized can be a group containing a hetero atom (for
example, a divalent group containing a chalcogen atom such as --O--
and --S--, and --N(R)-- group, wherein R is a hydrogen atom or an
alkyl group and said alkyl group is identical with an alkyl group
represented by R.sub.101 in aforesaid Formula (33)) in addition to
a hydrocarbon group such as an alkylene group (such as an ethylene
group, a trimethilene group, a tetramethylene group, a propylene
group, an ethylethylene group, a pentamethylene group, a
hexamethylene group, 2,2,4-trimethylhexamethylene group, a
heptamethylene group, an octamethylene group, a nonamethylene
group, a decamethylene group, an undecamethylene group, a
dodecamethylene group, a cyclohexylene group (such as
1,6-cyclohexanediyl group), a cyclopentylene group (such as
1,5-cyclopentanediyl group)), an alkenylene group (such as a
vinylene group and a propenylene group), an alkynylene group (such
as an ethylenylene group and a 3-pentynylene group) and an arylene
group.
[0406] Further, in each of the above-described alkenylene group,
alkynylene group and arylene group, at least one of carbon atoms,
which constitute a divalent connecting group, may be substituted by
a charcogen atom (such as oxygen and sulfur) or aforesaid --N(R)--
group.
[0407] Further, as a divalent group represented by L.sub.1, for
example, a group having a divalent heterocyclic group is utilized
and listed are such as a oxazolediyl group, a pyrimidinediyl group,
a pyridazinediyl group, a pyradinediyl group, a pyrrolinediyl
group, an imidazolinediyl group, an imidazolidinediyl group, a
pyrazolidinediyl group, a pyrazolinediyl group, a piperidinediyl
group, a piperadinediyl group, a morpholinediyl group and a
quinuclidinediyl group; and also listed may be a divalent
connecting group arising from a compound having an aromatic
heterocyclic ring (also referred to as a hetero aromatic compound)
such as a thiophene-2,5-diyl group and a pyridine-2,3-diyl
group.
[0408] Further, also listed may be a group which bonds via a hetero
atom such as an alkylimino group, a dialkylsilanediyl group and an
allylgermanediyl group.
[0409] By utilizing a compound represented by aforesaid Formula
(42), an organic EL element having higher emission efficiency can
be prepared. Further, the life of the organic EL element can be
prolonged.
[0410] In a compound represented by each of aforesaid Formulas
(43)-(47), a substituent represented by each of R.sub.1 and R.sub.2
is identical with a substituent represented by R.sub.101 in
aforesaid Formula (33).
[0411] In aforesaid Formula (47), a 6-membered aromatic
heterocyclic ring containing at least one nitrogen atom represented
by each of Z.sub.1, Z.sub.2, Z.sub.3 and Z.sub.4 includes such as a
pyridine ring, a pyridazine ring, a pyrimidine ring and a pyradine
ring.
[0412] In aforesaid Formula (48), a 6-membered aromatic
heterocyclic ring containing at least one nitrogen atom represented
by each of Z.sub.1 and Z.sub.2 includes such as a pyridine ring, a
pyridazine ring, a pyrimidine ring and a pyradine ring.
[0413] In aforesaid Formula (48), an arylen group represented by
each of Ar.sub.1 and Ar.sub.2 includes o-phenylene group, a
m-phenylene group, a p-phenylene group, a naphthalenediyl group, an
anthracenediyl group, a naphthacenediyl group, a pyrenediyl group,
a naphthylnaphthalenediyl group, a biphenyldiyl group (such as
3,3'-biphenyldiyl group and a 3,6-biphenyldiyl group), a
terphenyldiyl group, a quaterphenyldiyl group, a quinquiphenyldiyl
group, a sexiphenyldiyl group, a septiphenyldiyl group, an
octiphenyldiyl group, a nobiphenyldiyl group and a deciphenyldiyl
group. Further, the aforesaid arylene group may be provided with a
substituent which will be described later.
[0414] In aforesaid Formula (48), a divalent aromatic heterocyclic
group represented by each of Ar.sub.1 and Ar.sub.2 includes a
divalent group derived from such as a furan ring, a thiophene ring,
a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyradine
ring, a triazine ring, a benzoimidazole ring, an oxadiazole ring, a
triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring,
an indole ring, a benzoimidazole ring, a benzothiazole ring, a
benzooxazole ring, a quinoxaline ring, a quinazoline ring, a
phthalazine ring, a carbazole ring, a carboline ring and a ring in
which at least one of carbon atoms of a hydrocarbon ring
constituting a carboline ring is further substituted by a nitrogen
atom. Further, the aforesaid aromatic heterocyclic group may be
provided with a substituent represented by aforesaid R.sub.101.
[0415] In aforesaid Formula (48), a divalent connecting group
represented by L is identical with a divalent connecting group
represented by L.sub.1 in aforesaid Formula (42), however,
preferable are an alkylene group and a divalent group containing a
charcogen atom such as --O-- and --S--, and most preferable is an
alkylene group.
[0416] In aforesaid Formula (49), an arylen group represented by
each of Ar.sub.1 and Ar.sub.2 is identical with an arylen group
represented by each of Ar.sub.1 and Ar.sub.2 in aforesaid Formula
(48).
[0417] In aforesaid Formula (49), an aromatic heterocyclic group
represented by each of Ar.sub.1 and Ar.sub.2 is identical with an
aromatic heterocyclic group represented by each of Ar.sub.1 and
Ar.sub.2 in aforesaid Formula (48).
[0418] In aforesaid Formula (49), a 6-membered aromatic
heterocyclic ring containing at least one nitrogen atom represented
by each of Z.sub.1, Z.sub.2, Z.sub.3 and Z.sub.4 includes such as a
pyridine ring, a pyridazine ring, a pyrimidine ring and a pyridine
ring.
[0419] In aforesaid Formula (49), a divalent connecting group
represented by L is identical with a divalent connecting group
represented by L.sub.1 is in aforesaid Formula (42), however,
preferable are an alkylene group and a divalent group containing a
charcogen atom such as --O-- and --S--, and most preferable is an
alkylene group.
[0420] In the following, specific examples represented by Formula
(33) according to the present invention will be shown; however, the
present invention is not limited thereto. TABLE-US-00002 COM- POUND
CENTRAL MOIETY A 1 ##STR271## ##STR272## 2 ##STR273## ##STR274## 3
##STR275## ##STR276## 4 ##STR277## ##STR278## 5 ##STR279##
##STR280## 6 ##STR281## ##STR282## 7 ##STR283## ##STR284## 8
##STR285## ##STR286## 9 ##STR287## ##STR288## 10 ##STR289##
##STR290## 11 ##STR291## ##STR292## 12 ##STR293## ##STR294## 13
##STR295## ##STR296## 14 ##STR297## ##STR298## 15 ##STR299##
##STR300## 16 ##STR301## ##STR302## 17 ##STR303## ##STR304## 18
##STR305## ##STR306## 19 ##STR307## ##STR308## 20 ##STR309##
##STR310## 21 ##STR311## ##STR312## 22 ##STR313## ##STR314## 23
##STR315## ##STR316## 24 ##STR317## ##STR318## 25 ##STR319##
##STR320## 26 ##STR321## ##STR322## 27 ##STR323## ##STR324## 28
##STR325## ##STR326## 29 ##STR327## ##STR328## 30 ##STR329##
##STR330## 31 ##STR331## ##STR332## 32 ##STR333## ##STR334## 33
##STR335## ##STR336## 34 ##STR337## ##STR338## 35 ##STR339##
##STR340## 36 ##STR341## ##STR342## 37 ##STR343## ##STR344## 38
##STR345## ##STR346## 39 ##STR347## ##STR348## 40 ##STR349##
##STR350## 41 ##STR351## ##STR352## 42 ##STR353## ##STR354## 43
##STR355## ##STR356## 44 ##STR357## ##STR358## 45 ##STR359##
##STR360## 46 ##STR361## ##STR362## 47 ##STR363## ##STR364## 48
##STR365## ##STR366## 49 ##STR367## ##STR368## 50 ##STR369##
##STR370## 51 ##STR371## ##STR372## 52 ##STR373## ##STR374## 53
##STR375## ##STR376## 54 ##STR377## ##STR378## 55 ##STR379##
##STR380## 56 ##STR381## ##STR382## 57 ##STR383## ##STR384## 58
##STR385## ##STR386## 59 ##STR387## ##STR388##
[0421] ##STR389## ##STR390## ##STR391## ##STR392## ##STR393##
##STR394## ##STR395## ##STR396## ##STR397## ##STR398## ##STR399##
##STR400## ##STR401## ##STR402## ##STR403##
[0422] The emission host employed in the present invention may be a
low molecular weight compound, a polymer compound having a repeat
unit, or a low molecular compound having a polymerizable group, for
example. a vinyl group or an epoxy group (a vacuum evaporated
polymerizable host).
[0423] The emission host is preferably a compound which prevents
elongation of the wavelength of the emission and has a high Tg (a
glass transition temperature), while having a hole transport
property or an electron transport property.
[0424] As specific examples of an emission host, preferable are the
compounds described in the following documents, for example: JP-A
Nos. 2001-257076, 2002-308855, 2001-313179, 2002-319491,
2001-357977, 2002-334786, 2002-8860, 2002-334787, 2002-15871,
2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579,
2002-105445, 2002-343568, 2002-141173, 2002-352957, 2002-203683,
2002-363227, 2002-231453, 2003-3165, 2002-234888, 2003-27048,
2002-255934, 2002-260861, 2002-280183, 2002-299060, 2002-302516,
2002-305083, 2002-305084 and 2002-308837.
[0425] Next, constitutions of typical organic EL elements will be
described.
<<Constituting Layers of Organic EL Element>>
[0426] The constituting layers of the organic EL element of the
present invention will be explained.
[0427] Preferable examples of the constituting layers of the
organic EL element of the present invention will be shown below,
however, the present invention is not limited thereto. (i)
Anode/Hole transport layer/Light emission layer/Hole blocking
layer/Electron transport layer/Cathode (ii) Anode/Electron blocking
layer/Light emission layer/Hole blocking layer/Electron transport
layer/Cathode (iii) Anode/Hole transport layer/Electron blocking
layer/Light emission layer/Hole blocking layer/Electron transport
layer/Cathode (iv) Anode/Hole transport layer/Electron blocking
layer/Light emission layer/Hole blocking layer/Electron transport
layer/Cathode (v) Anode/Hole transport layer/Electron blocking
layer/Light emission layer/Hole blocking layer/Electron transport
layer/Cathode buffer layer/Cathode (vi) Anode/Anode buffer
layer/Hole transport layer/Electron blocking layer/Light emission
layer/Hole blocking layer/Electron transport layer/Cathode buffer
layer/Cathode (vii) Anode/Anode buffer layer/Hole transport
layer/Electron blocking layer/Light emission layer/Hole blocking
layer/Electron transport layer/Cathode buffer layer/Cathode
<<Blocking Layer (Electron Blocking Layer, Hole Blocking
Layer>>
[0428] A blocking layer of the present invention (for example, an
electron blocking layer, an electron hole blocking layer) will be
explained.
[0429] In the present invention, the material for the organic EL
element of the present invention is preferably used, for example,
in the hole blocking layer or in the electron blocking layer, and
more preferably in the hole blocking layer.
[0430] When the material for the organic EL element of the present
invention is used, for example, in the hole blocking layer or in
the electron blocking layer, the metal complex of the present
invention described in any one of the above Items (1) to (17) may
be incorporated in the hole blocking layer or in the electron
blocking layer, in a state of 100% by weight or in a state of being
mixed with another organic compound (for example, a compound used
in the constituting layer of the organic EL element of the present
invention).
[0431] The thickness of the blocking layer of the present invention
is preferably 3 nm-100 nm, and more preferably 5 nm-30 nm.
<<Hole Blocking Layer>>
[0432] The hole blocking layer has a function of an electron
transport layer in a broad sense and contains a material having an
ability of transporting electrons, however, an extremely poor
ability of transporting holes, which can increase a recombination
probability of electrons and holes by transporting electrons while
blocking holes.
[0433] The hole blocking layer, for example, disclosed in JP-A Nos.
11-204258 and 11-204359, and the hole blocking layer described in
page 237 of "Organic EL element and its frontier of
industrialization" (published by NTS Corporation, Nov. 30, 1998),
can be used as the hole blocking layer of the present invention.
Further, when necessary, the constitution of an electron transport
layer which will be described later can also be used as the hole
blocking layer of the present invention.
[0434] In the present invention, it is preferable to use a compound
represented by the above Formula (33) in a layer adjacent to the
light emission layer, namely, in a hole blocking layer or in an
electron blocking layer, and specifically preferable is to use it
in the hole blocking layer.
<<Hole Transport Layer>>
[0435] The hole transport layer contains a hole transport material
having a hole transport ability. A hole injection layer and an
electron blocking layer are included in a hole transport layer in a
broad sense. The hole transport layer may either be an single layer
or a lamination layer containing a plurality of layers.
[0436] The hole transport material is not specifically limited, and
can be arbitrarily selected from commonly used hole
injection-transport materials in a photo conduction material or
from the materials known in the art in a hole injection layer or in
a hole transport layer of an organic EL element.
[0437] A hole transport material means a compound having a hole
injection ability, a hole transport ability or an electron blocking
ability, and it may be an organic substance or an inorganic
substance. Examples of a hole transport material include: a
triazole derivative, an oxadiazole derivative, an imidazole
derivative, a polyarylalkane derivative, a pyrazoline derivative, a
pyrazolone derivative, a phenylenediamine derivative, an arylamine
derivative, an amino substituted chalcone derivative, an oxazole
derivative, a styrylanthracene derivative, a fluorenone derivative,
a hydrazone derivative, a stilbene derivative, a silazane
derivative, an aniline-containing copolymer, and an
electroconductive oligomer, specifically, a thiophene oligomer.
[0438] As the hole transport material, those described above are
used, however, a porphyrin compound, an aromatic tertiary amine
compound and a styrylamine compound are preferable, and,
specifically, an aromatic tertiary amine compound is
preferable.
[0439] Typical examples of the aromatic tertiary amine compound and
styrylamine compound include:
N,N,N',N'-tetraphenyl-4,4'-diaminophenyl,
N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine
(TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane,
1,1-bis(4-di-p-tolylaminophenyl)cyclohexane,
N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl,
1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane,
bis(4-dimethylamino-2-methylphenyl)phenylmethane,
bis(4-di-p-tolylaminophenyl)phenylmethane,
N,N'-diphenyl-N,N'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl,
N,N,N',N'-tetraphenyl-4,4'-diaminodiphenylether,
4,4'-bis(diphenylamino)quardriphenyl, N,N,N-tri(p-tolyl)amine,
4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene,
4-N,N-diphenylamino-(2-diphenylvinyl)benzene,
3-methoxy-4'-N,N-diphenylaminostylbene, N-phenylcarbazole,
compounds described in U.S. Pat. No. 5,061,569 which have two
condensed aromatic rings in the molecule thereof such as
4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and compounds
described in JP-A No. 4-308688 such as
4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]-triphenylamine
(MTDATA) in which three triphenylamine units are bonded in a
starburst form.
[0440] A polymer in which the material mentioned above is
introduced in the polymer chain or a polymer having the above
mentioned material as the polymer main chain can also be used.
[0441] As a hole injecting material or a hole transport material,
inorganic compounds such as p-Si and p-SiC are usable. Further, the
hole transport material preferably has a high Tg.
[0442] The hole transport layer can be formed by preparing a thin
layer of the above-mentioned hole transport material using a known
method such as a vacuum deposition method, a spin coat method, a
cast method, an inkjet method, or an LB method. The thickness of
the hole transport layer is not specifically limited, however, it
is ordinarily from 5 nm to 5000 nm. The hole transport layer may be
composed of a single layer structure containing one or more of the
materials mentioned above.
<<Electron Transport Layer>>
[0443] The electron transport layer contains a material having an
electron transport ability, and in a broad sense an electron
injection layer or a hole blocking layer are included in an
electron transport layer. The electron transport layer can be
provided as a single layer or as a plurality of layers.
[0444] The following materials have been known as an electron
transport material (which serves also as a hole blocking material)
used in a single electron transport layer or in the electron
transport layer closest to the cathode when plural electron
transport layers are employed.
[0445] The electron transport layer has a function of transporting
electrons injected from a cathode to a emission layer, and the
material used in the electron transport layer can be optionally
selected from the compounds known in the art.
[0446] Examples of the material used in the electron transport
layer (hereafter, referred to as the electron transport material)
include: a nitro-substituted fluorene derivative, a diphenylquinone
derivative, a thiopyran dioxide derivative, a carbodiimide, a
fluolenylidenemethane derivative, an anthraquinodimethane, an
anthrone derivative, and an oxadiazole derivative. Moreover, a
thiadiazole derivative which is formed by substituting the oxygen
atom in the oxadiazole ring of the foregoing oxadiazole derivative
with a sulfur atom, and a quinoxaline derivative having a
quinoxaline ring known as an electron withdrawing group are usable
as the electron transport material.
[0447] A polymer in which the material mentioned above is
introduced in the polymer chain or a polymer having the material as
the polymer main chain can be also used.
[0448] A metal complex of an 8-quinolynol derivative such as
aluminum tris(8-quinolynol) (Alq), aluminum
tris(5,7-dichloro-8-quinolynol), aluminum
tris(5,7-dibromo-8-quinolynol), aluminum
tris(2-methyl-8-quinolynol), aluminum tris(5-methyl-8-quinolynol),
or zinc bis(8-quinolynol) (Znq), and a metal complex formed by
replacing the central metal of the foregoing complexes with another
metal atom such as In, Mg, Cu, Ca, Sn, Ga or Pb, can be used as the
electron transport material. Furthermore, a metal free or
metal-containing phthalocyanine, and a derivative thereof, in which
the molecular terminal is replaced by a substituent such as an
alkyl group or a sulfonic acid group, are also preferably used as
the electron transport material. The distyrylpyrazine derivative
exemplified as a material for the emission layer may preferably be
employed as the electron transport material. An inorganic
semiconductor such as n-Si and n-SiC may also be used as the
electron transport material in a similar way as in the hole
injection layer or in the hole transport layer.
[0449] The electron transport layer can be formed employing the
above described electron transport materials and by forming into a
film using a known method such as a vacuum deposition method, a
spin coat method, a cast method, an inkjet method or an LB method.
The thickness of electron transport layer is not specifically
limited, however, is ordinarily from 5 to 5000 nm. The electron
transport layer may be composed of a single layer containing one
kind or two or more kinds of the above-mentioned electron transport
materials.
[0450] Next, the injection layer used as one of the constituting
layers of the organic EL element of the present invention will be
explained.
<<Injection Layer>>: Electron Injection Layer, Hole
Injection Layer
[0451] The injection layer is optionally provided, for example, an
electron injection layer or a hole injection layer, and may be
provided between the anode and the emission layer or the hole
transport layer, and between the cathode and the emission layer or
the electron transport layer as described above.
[0452] The injection layer herein referred to is a layer provided
between the electrode and an organic layer in order to reduce the
driving voltage or to improve of light emission efficiency. As the
injection layer, there are a hole injection layer (an anode buffer
layer) and an electron injection layer (a cathode buffer layer),
which are described in "Electrode Material" pages 123-166, Div. 2
Chapter 2 of "Organic EL element and its frontier of
industrialization" (published by NTS Corporation, Nov. 30, 1998) in
detail.
[0453] The anode buffer layer (a hole injection layer) is described
in, for example, JP-A Nos. 9-45479, 9-260062, and 8-288069, and its
examples include a phthalocyanine buffer layer represented by a
copper phthalocyanine layer, an oxide buffer layer represented by a
vanadium oxide layer, an amorphous carbon buffer layer, and a
polymer buffer layer employing an electroconductive polymer such as
polyaniline (emeraldine) or polythiophene.
[0454] The cathode buffer layer (an electron injection layer) is
described in, for example, JP-A Nos. 6-325871, 9-17574, and
10-74586, in detail, and its examples include a metal buffer layer
represented by a strontium or aluminum layer, an alkali metal
compound buffer layer represented by a lithium fluoride layer, an
alkali earth metal compound buffer layer represented by a magnesium
fluoride layer, and an oxide buffer layer represented by an
aluminum oxide.
[0455] The buffer layer (an injection layer) is preferably very
thin and has a thickness of preferably from 0.1 to 100 nm depending
on the kind of the material used.
[0456] The injection layer can be formed by preparing a thin layer
of the above-mentioned injection material using a known method such
as a vacuum deposition method, a spin coat method, a cast method,
an inkjet method, or an LB method. The thickness of the injection
layer is not specifically limited, however, it is ordinarily from 5
nm to 5000 nm. The injection layer may be composed of a single
layer structure containing one kind or two or more kinds of the
materials mentioned above.
<<Anode>>
[0457] For the anode of the organic EL element, a metal, an alloy,
or an electroconductive compound each having a high working
function (not less than 4 eV), and mixture thereof are preferably
used as the electrode material. Specific examples of such an
electrode material include a metal such as Au, CuI and a
transparent electroconductive material such as indium tin oxide
(ITO), SnO.sub.2, or ZnO. A material capable of forming an
amorphous and transparent conductive layer such as IDIXO
(In.sub.2O.sub.3--ZnO) may also be used. The anode may be prepared
by forming a thin layer of the electrode material according to a
depositing or sputtering method, and by forming the layer into a
desired pattern according to a photolithographic method. When
required precision of the pattern is not so high (not less than 100
.mu.m), the pattern may be formed by depositing or sputtering of
the electrode material through a mask having a desired form. When
light is emitted through the anode, the transmittance of the anode
is preferably 10% or more, and the sheet resistance of the anode is
preferably not more than several hundred ohm/sq. The thickness of
the layer is ordinarily within the range of from 10-1000 nm, and
preferably from 10-200 nm, although it may vary due to kinds of
materials used.
<<Cathode>>
[0458] On the other hand, for the cathode, a metal (also referred
to as an electron injecting metal), an alloy, and an
electroconductive compound each having a low working function (not
more than 4 eV), and a mixture thereof are used as the electrode
material. Specific examples of such an electrode material include
sodium, sodium-potassium alloy, magnesium, lithium, a
magnesium/copper mixture, a magnesium/silver mixture, a
magnesium/aluminum mixture, magnesium/indium mixture, an
aluminum/aluminum oxide (Al.sub.2O.sub.3) mixture, indium, a
lithium/aluminum mixture, and a rare-earth metal. Among them, a
mixture of an electron injecting metal and a metal higher in the
working function than that of the electron injecting metal, such as
the magnesium/silver mixture, magnesium/aluminum mixture,
magnesium/indium mixture, aluminum/aluminum oxide (Al.sub.2O.sub.3)
mixture, lithium/aluminum mixture, or aluminum is suitable from the
view point of the electron injecting ability and resistance to
oxidation. The cathode can be prepared forming a thin layer of such
an electrode material by a method such as a deposition or
spattering method. The sheet resistance as the cathode is
preferably not more than several hundred ohm/sq, and the thickness
of the layer is ordinarily from 10 nm-1000 nm, and preferably from
50 nm-200 nm. It is preferable in increasing the light emission
efficiency that either the anode or the cathode of the organic EL
element is transparent or semi-transparent.
<<Substrate (Also Referred to as Base Plate, Base or
Support)>>
[0459] The substrate employed for the organic EL element of the
present invention is not restricted to specific kinds of materials
such as glass and plastic, as far as it is transparent. Examples of
the substrate preferably used include glass, quartz and light
transmissible plastic film. Specifically preferred one is a resin
film capable of providing flexibility to the organic EL
element.
[0460] Examples of the resin film include films of polyethylene
terephthalate (PET), polyethylene naphthalate (PEN),
polyethersulfone (PES), polyetherimide, polyetheretherketone,
polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC),
cellulose triacetate (TAC) and cellulose acetate propionate
(CAP).
[0461] The surface of the resin film may have a layer of an
inorganic or organic compound or a hybrid layer of both compounds
which is preferably a high barrier film having a moisture
permeability of not more than 0.01 g/m.sup.2dayat.
[0462] The external light emission efficiency of the organic
electroluminescence element of the present invention is preferably
not less than 1%, and more preferably not less than 2% at room
temperature. Herein, external quantum yield (%) is represented by
the following formula: External quantum yield (%)=((the number of
photons emitted to the exterior of the organic EL element)/(the
number of electrons supplied to the organic EL
element)).times.100
[0463] A hue improving filter such as a color filter may be used in
combination.
[0464] When used as an illuminator, a film being subjected to a
surface roughening treatment (for example, an antiglare film) may
be used together, in order to reduce the emission irregularity.
[0465] When used as a multicolored display, at least two organic EL
elements having different emission maximum wavelengths are used. A
preferable example of manufacturing an organic EL element will now
be explained.
<<Preparation Method of Organic EL Element>>
[0466] For one example, the preparation of the organic EL element,
which has the following constitution will be described: Anode/Hole
injection layer/Hole transport layer/Emission layer/Electron
transport layer/Cathode buffer layer/Cathode.
[0467] A thin layer of a desired material for an electrode such as
a material of the anode is formed on a suitable substrate by a
vacuum deposition or sputtering method to prepare the anode so that
the thickness of the layer is not more than 1 .mu.m and preferably
within the range of from 10 to 200 nm. Then organic compound thin
layers including the hole injection layer, the hole transport
layer, the emission layer, the hole blocking layer and the electron
transport layer, which constitute the organic EL element, are
formed on the resulting anode.
[0468] As methods for formation of the thin layers, as the same as
described above, there are a vacuum deposition method and a wet
process (for example, a spin coating method, a cast method, an
inkjet method, and a printing method), however, a vacuum deposition
method, a spin coating method, an inkjet method and a printing
method are preferably used, since a uniform layer without a pinhole
can be formed. Different methods may be used for formation of
different layers. When the vacuum deposition method is used for the
thin layer formation method, although conditions of the vacuum
deposition differs due to kinds of materials used, vacuum
deposition is preferably carried out at a boat temperature of
50-450.degree. C., at a degree of vacuum of from 10.sup.-6 to
10.sup.-2 Pa, at a deposition speed of 0.01-50 nm/second, and at a
substrate temperature of -50-300.degree. C. to form a layer with a
thickness of 0.1 nm-5 .mu.m.
[0469] After these layers has been formed, a thin layer of a
material for a cathode is formed thereon to prepare a cathode,
employing, for example, a vacuum deposition method or sputtering
method to give a thickness of not more than 1 .mu.m, and preferably
50-200 nm. Thus, a desired organic EL element is obtained. It is
preferred that the layers from the hole injection layer to the
cathode are continuously formed under one time of vacuuming to
obtain an organic EL element. However, on the way of the layer
formation under vacuum, a different layer formation method by
taking the layer out of the vacuum chamber may be inserted. When
the different method is used, the process is required to be carried
out under a dry inert gas atmosphere.
<<Display>>
[0470] The display of the present invention will now be
explained.
[0471] In the present invention, the display may be single color or
may be multicolor, however, a multicolor display will now be
explained. In the multicolor display of the present invention, the
emission layer only is formed using a shadow mask, and the other
layers, besides the emission layer, can be formed all over the
substrate employing a vacuum method, a cast method, a spin coat
method an inkjet method or a printing method.
[0472] When the emission layer only is formed by patterning, the
layer formation, although not specifically limited, is carried out
preferably according to a vacuum deposition method, an inkjet
method or a printing method. When a vacuum deposition method is
used as the layer formation method, patterning of the layer is
preferably carried out employing a shadow mask.
[0473] Further, the organic EL element can be prepared in the
reverse order, in which the cathode, the electron transport layer,
the hole blocking layer, the emission layer, the hole transport
layer, and the anode are formed in that order. When a direct
current voltage, a voltage of 2 to 40 V is applied to thus obtained
multicolor display, setting the anode as a + polarity and the
cathode as a - polarity, light emission is observed. When a voltage
with the reverse polarity is applied, no current flows and no light
emission is observed. When an alternating current is applied, light
emission is observed only when + is applied to the anode and - is
applied to the cathode. Arbitrary wave shape of alternating current
may be used.
[0474] The multicolor display can be used as a display for
indication, a display, or various light emission sources. The
display for indication or the display, which employs three kinds of
organic EL elements emitting a blue light, a red light and a green
light can present a full color image.
[0475] Examples of the display or the display include a television,
a personal computer, a mobile device or an AV device, a display for
text broadcasting, and an information display used in a car. The
display may be used as specifically a display for reproducing a
still image or a moving image. When the display is used as a
display for reproducing a moving image, the driving method may be
either a simple matrix (passive matrix) method or an active matrix
method.
[0476] Examples of an illuminator include a home lamp, a room lamp
in a car, a backlight for a watch or a liquid crystal, a light
source for boarding advertisement, a signal device, a light source
for a photo memory medium, a light source for an
electrophotographic copier, a light source for an optical
communication instrument, and a light source for an optical sensor,
however, are not limited thereto.
<<Illuminator>>
[0477] The illuminator of the present invention will now be
explained.
[0478] The organic EL element of the present invention may be an
organic EL element having a resonator structure. The organic EL
element having a resonator structure is applied to a light source
for a photo-memory medium, a light source for an
electrophotographic copier, a light source for an optical
communication instrument, or a light source for a photo-sensor,
however, its application is not limited thereto. In the above
application, a laser oscillation may be carried out.
[0479] The organic EL element of the present invention can be used
as a lamp such as an illuminating lamp or a light source for
exposure, as a projection device for projecting an image, or as a
display for directly viewing a still image or a moving image. When
the element is used in a display for reproducing a moving image,
the driving method may be either a simple matrix (passive matrix)
method or an active matrix method. The display can present a full
color image by employing two or more kinds of organic EL elements
each emitting light with a different color.
[0480] One of the examples of the display containing the organic EL
element of the present invention will be explained below employing
Figures.
[0481] FIG. 1 is a schematic drawing of one example of a display
containing an organic EL element. FIG. 1 is a display such as that
of a cellular phone, displaying image information due to light
emission from the organic EL.
[0482] Display 1 contains a display section A having plural pixels
and a control section B carrying out image scanning based on image
information to display an image in the display section A.
[0483] The control section B is electrically connected to the
display section A, transmits a scanning signal and an image data
signal to each of the plural pixels based on image information from
the exterior, and conducts image scanning which emits light from
each pixel due to the scanning signal according to the image data
signal, whereby an image is displayed on the display section A.
[0484] FIG. 2 is a schematic drawing of a display section A.
[0485] The display section A contains a substrate, plural pixels 3,
and a wiring section containing plural scanning lines 5 and plural
data lines 6. The main members of the display section A will be
explained below.
[0486] In FIG. 2, light from pixels 3 is emitted in the direction
of an arrow (downward).
[0487] The plural scanning lines 5 and plural data lines 6 of the
wiring section 2 each are composed of an electroconductive
material, the lines 5 and the lines 6 being crossed with each other
at a right angle, and connected with the pixels 3 at the crossed
points (not illustrated).
[0488] The pixel 3, when the scanning signal is applied from the
scanning lines 5, receives the data signal from the data lines 6,
and emits light corresponding to the image data received. By
providing red light emitting pixels, green light emitting pixels,
and blue light emitting pixels side by side on the same substrate,
a full color image can be displayed.
[0489] Next, an emission process of pixels will be explained.
[0490] FIG. 3 is a schematic drawing of a pixel.
[0491] The pixel contains an organic EL element 10, a switching
transistor 11, a driving transistor 12, and a capacitor 13. When a
pixel with a red light emitting organic EL element, a pixel with a
green light emitting organic EL element, and a pixel with a blue
light emitting organic EL element are provided side by side on the
same substrate, a full color image can be displayed.
[0492] In FIG. 3, an image data signal is applied through the data
lines 6 from the control section B to a drain of the switching
transistor 11, and when a scanning signal is applied to a gate of
the switching transistor 11 through the scanning lines 5 from the
control section B, the switching transistor 11 is switched on, and
the image signal data applied to the drain is transmitted to the
capacitor 13 and the gate of the driving transistor 12.
[0493] The capacitor 13 is charged according to the electric
potential of the image data signal transmitted, and the driving
transistor 12 is switched on. In the driving transistor 12, the
drain is connected to an electric source line 7, and the source to
an organic EL element 10. Current is supplied from the electric
source line 7 to the organic EL element 10 according to the
electric potential of the image data signal applied to the
gate.
[0494] The scanning signal is transmitted to the next scanning line
5 according to the successive scanning of the control section B,
the switching transistor 11 is switched off. Even if the switching
transistor 11 is switched off, the driving transistor 12 is turned
on since the capacitor 13 maintains a charged potential of image
data signal, and light emission from the organic EL element 10
continues until the next scanning signal is applied. When the next
scanning signal is applied according the successive scanning, the
driving transistor 12 works according to an electric potential of
the next image data signal synchronized with the scanning signal,
and light is emitted from the organic EL element 10.
[0495] That is, light is emitted from the organic EL element 10 in
each of the plural pixels 3 due to the switching transistor 11 as
an active element and the driving transistor 12 each being provided
in the organic EL element 10 of each of the plural pixels 3. This
emission process is called an active matrix process.
[0496] Herein, light emission from the organic EL element 10 may be
emission with plural gradations according to image signal data of
multiple value having plural gradation potentials, or emission due
to on-off according to a binary value of the image data
signals.
[0497] The electric potential of the capacitor 13 may maintain till
the next application of the scanning signal, or may be discharged
immediately before the next scanning signal is applied.
[0498] In the present invention, light emission may be carried out
employing a passive matrix method as well as the active matrix
method as described above. The passive matrix method is one in
which light is emitted from the organic EL element according to the
data signal only when the scanning signals are scanned.
[0499] FIG. 4 is a schematic drawing of a display employing a
passive matrix method. In FIG. 4, pixels 3 are provided between the
scanning lines 5 and the data lines 6, crossing with each
other.
[0500] When scanning signal is applied to scanning line 5 according
to successive scanning, pixel 3 connecting the scanning line 5
emits according to the image data signal. The passive matrix method
has no active element in the pixel 3, which reduces manufacturing
cost of a display.
[0501] The organic EL element of the present invention can be
applied to an organic EL element emitting substantially white light
as an illuminator. White light is obtained by mixing plural color
lights, which are emitted from plural emission compounds. A
combination of the plural color lights may be that of lights of
three primary colors, blue, green, and red colors, each having a
different emission maximum wavelength, or that of lights of
complementary colors such as blue and yellow colors, or blue green
and orange colors, each having a different emission maximum
wavelength.
[0502] A combination of light emitting materials for obtaining
plural color lights may be a combination of materials emitting
plural fluorescent or phosphorescent light (light emission
dopants), or a combination of a fluorescent or phosphorescent light
emitting-material and a colorant which emit light under excitation
due to excitation light from the light emitting-material. In the
white light emitting organic EL element of the present invention,
preferable is a combination of only plural light emitting
dopants.
[0503] Examples of a layer construction of an organic EL element to
obtain a plurality of emitting colors include: a method to mix a
plurality of emitting dopants in an emitting layer; a method to
provide a plurality of emitting layers each containing an emitting
dopant exhibiting a different emitting wavelength from other
dopant; and a method to mount minute pixels emitting lights of
different wavelengths in a matrix arrangement on a substrate.
[0504] In the organic EL element emitting white light of the
present invention, pattering may be carried out by using a mask, if
necessary, while a layer is formed or by ink-jet printing.
Patterning may be carried out only for an electrode, for an
electrode and an emitting lay or for all the layers of the organic
EL element.
[0505] Light emitting materials used in the light emitting layer
are not specifically limited. For example, a back light used in a
liquid crystal display is prepared by arbitrary selecting materials
from platinum-complexes relating to the present invention or from
known light emitting compounds and by using the selected materials
in combination to emit white light, so that the emitted light fits
the wavelength range corresponding to the CF (color filter)
property.
[0506] The white light emitting organic EL element of the present
invention may be suitably used for a variety of emitting light
source, an illuminator for household use or in a vehicle, a kind of
a lamp such as a light source for exposure, or for a display
device, for example, as a back light of a liquid crystal
display.
[0507] Other examples of the usage include: a backlight of a watch,
an advertisement signboard, a traffic light, a light source for an
optical memory medium, a light source for an electrophotographic
copier, a light source for an optical communication processor, a
light source for a light sensor and electric appliances for
household use having a display device.
EXAMPLES
[0508] In the following, the present invention will be explained
using examples, however, the present invention is not limited
thereto.
[0509] Here, a list of compounds used in the examples (the
compounds listed in the tables as well as those which are not
listed in the tables but evaluated and only the results are given)
will be shown. ##STR404## ##STR405## ##STR406## ##STR407##
##STR408## ##STR409## ##STR410## ##STR411## ##STR412##
Example 1
Preparation of White Light Emitting Prganic EL Element 1-1
Inventive
[0510] On a 25 mm.times.25 mm.times.0.5 mm glass substrate, an
indium-tin oxide anode (ITO, indium/tin=95/5 in molar ratio) was
formed via a sputtering method employing a direct current power
source (thickness: 200 nm). The surface resistance of the anode was
10 .OMEGA./sq. Subsequently, in order to obtain 65% of emission
component of green light when a current of 10 mA/cm.sup.2 was
passed through the fabricated element, prepared was:
polyvinylcarbazole (hole transporting binder polymer)/BDM-1 (blue
light emitting ortho metalated complex)/GDM-1
tris(2-phenylpyridine)iridium complex (green light emitting ortho
metalated
complex)/RDM-1:bis(2-benzothiophene[b]-2-yl-pyridine)acetylacet-
onate-iridium complex (red light emitting ortho metalated
complex)/2-(4-biphenilyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole
(electron transport material)=200/2/5/2/50 (in weight ratio),
followed by dissolving in dichloroethane and spin coating to form a
light emission layer of the thickness of 100 nm.
[0511] A patterned mask (a mask to form an emission area of 5
mm.times.5 mm) was placed on the obtained light emission layer, and
0.5 nm thickness of lithium fluoride layer as a cathode buffer
layer and 150 nm thickness of aluminum layer as the cathode were
deposited in a vacuum evaporation apparatus. Aluminum lead wires
were connected to the anode and the cathode to prepare an emission
element. The emission element was sealed with a glass container
using a UV-curable adhesive (XNR5493, produced by Nagase-Ciba Ltd.)
in a nitrogen-filled glove box to obtain a White Light Emitting
Organic EL Element 1-1 (Inventive) as shown in FIG. 5.
<<Preparation of White Light Emitting Organic EL Elements 1-2
to 1-15>>
[0512] White Light Emitting Organic EL Elements 1-2 to 1-12
(Inventive) and 1-13 to 1-15 (Comparative) were prepared in the
same manner as White Light Emitting Organic EL Element 1-1 except
that the materials listed in Table 1 were used and the spectral
ratio of green light emission in the emission spectrum of each
element was adjusted as shown in Table 1.
<<Preparation of GOLED-1 for Measuring Spectral Ratio of
Green Light Emission>>
[0513] In order to use for measuring the spectral ratio of green
light emission of a white light emitting organic EL element while a
current of 10 mA/cm.sup.2 is passed, GOLED-1 for measuring spectral
ratio of green light emission was prepared as follows.
[0514] On a 25 mm.times.25 mm.times.0.5 mm glass substrate, an
indium-tin oxide anode (ITO, indium/tin=95/5 in molar ratio) was
formed via a sputtering method employing a direct current power
source (thickness: 200 nm). The surface resistance of the anode was
10 .OMEGA./sq. Subsequently, a solution of: polyvinylcarbazole
(hole transporting binder polymer)/tris(2-phenylpyridine)iridium
complex (green light emitting ortho metalated
complex)/2-(4-biphenilyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole
(electron transport material)=200/10/50 (in weight ratio)
dissolving in dichloroethane was spin coated to form a light
emission layer of the thickness of 100 nm. A patterned mask (a mask
to form an emission area of 5 mm.times.5 mm) was placed on the
obtained light emission layer, and 0.5 nm thickness of lithium
fluoride layer as a cathode buffer layer and 150 nm thickness of
aluminum layer as the cathode were deposited in a vacuum
evaporation apparatus. Aluminum lead wires were connected to the
anode and the cathode to prepare an emission element. The emission
element was sealed with a glass container using a UV-curable
adhesive (XNR5493, produced by Nagase-Ciba Ltd.) in a
nitrogen-filled glove box to obtain a green light emitting element
as a comparative sample. The spectral curve of green emission
obtained from the green light emitting element is shown in FIG.
7.
<<Preparation of GOLED-2 to 4 for Measuring Spectral Ratio of
Green Light Emission>>
[0515] GOLED-2 to 4 for Measuring Spectral Ratio of Green Light
Emission were prepared in the same manner as GOLED-1 except that
materials for green light emission were changed as shown in Table
1. TABLE-US-00003 TABLE 1 Constitution of light emission layer
(thickness 100 nm) Spectral Used material and added amount (in
weight ratio) ratio of Hole Blue light Green light Red light
Electron green light Sample transport emitting emitting emitting
transport emission name material material material material
material (%)*1 Remarks 1-1 PVK 200 BMD-1 2 GDM-1 5 RDM-1 2 ET-1 50
65 Inventive 1-2 PVK 200 BMD-1 2 GDM-2 5 RDM-2 2 ET-2 50 67
Inventive 1-3 PVK 200 BMD-2 2 GDM-1 5 RDM-1 2 ET-1 50 69 Inventive
1-4 PVK 200 BMD-3 2 GDM-1 5 RDM-2 2 ET-2 50 66 Inventive 1-5 PVK
200 BMD-4 2 GDM-1 5 RDM-1 2 ET-1 50 68 Inventive 1-6 PVK 200 BMD-5
2 GDM-3 5 RDM-2 2 ET-2 50 70 Inventive 1-7 PVK 200 BMD-6 2 GDM-1 5
RDM-1 2 ET-1 50 68 Inventive 1-8 PVK 200 BMD-7 2 GDM-1 5 RDM-2 2
ET-2 50 70 Inventive 1-9 PVK 200 BMD-8 2 GDM-1 5 RDM-2 2 ET-2 50 63
Inventive 1-10 PVK 200 BMD-9 2 GDM-4 5 RDM-2 2 ET-1 50 67 Inventive
1-11 PVK 200 BMD-10 4 GDM-4 5 RDM-2 2 ET-1 50 65 Inventive 1-12 PVK
200 BMD-11 5 GDM-1 5 RDM-2 2 ET-1 50 66 Inventive 1-13 PVK 200 BD-1
1 GDM-1 5 RDM-1 1 ET-1 50 59 Comparative 1-14 PVK 200 BD-2 10 GDM-1
0.5 RDM-2 2 ET-2 50 55 Comparative 1-15 PVK 200 BGD-1 8 GDM-1 0.3
RDM-2 0.1 ET-2 50 35 Comparative GOLED-1 PVK 200 -- GDM-1 10 -- 50
*2 GOLED-2 PVK 200 -- GDM-2 10 -- 50 *2 GOLED-3 PVK 200 -- GDM-3 10
-- 50 *2 GOLED-4 PVK 200 -- GDM-4 10 -- 50 *2 *1Measured while 10
mA/cm.sup.2 of current was passed through the element *2
Comparative Sample
<<Spectral Ratio of Green Light Emission of Green Light
Emitting Ortho Metalated Complex>>
[0516] Comparison of the spectral curves was carried out using the
spectral curve of white light emission obtained from each obtained
element and the spectral curve of green light emission obtained
from each of GOLED-1 to 4 for measuring the spectral ratio (for
example, when an element employing GDM-1 was measured, comparison
of the spectral curve was carried out using GOLED-1 in which GDM-1
was employed), and the spectral ratio of a green light emitting
ortho metalated complex in the emission spectrum of a white light
was calculated.
[0517] Here, the emission spectrum in the wavelength range of 400
nm-800 nm obtained when 10 mA/cm.sup.2 of current was passed
through each element was used as the white light emission
spectrum.
[0518] The calculation method of the spectral ratio was as follows:
The two spectral curves of white light emission and green light
emission were standardized using the emission maximum of the green
light emission. When the areas surrounded by each standardized
spectral curve and the abscissa axis (wavelength axis) were
designated as white light emission intensity (ELwhite) and green
light emission intensity (ELgreen), the value of:
Agreen=(Elgreen)/(Elwhite) was adopted as a spectral ratio of green
light emitting ortho metalated complex. When a white light emitting
element contains no green light emitting compound, the spectral
ratio of green light emission is 0 without calculation.
<<Emission Luminance, Emission Efficiency>>
[0519] Light emission was carried out by passing a direct current
through each of the obtained Organic El Elements 1-1 to 1-15 using
Source measure unit 2400 produced by Toyo Technica Inc., and
measured were an emission luminance (cd/m.sup.2) while 10 V direct
current was applied and an emission efficiency (lm/W) while a
current of 2.5 mA/cm.sup.2 was passed through.
<<CIE Chromaticity of White Light>>
[0520] A direct current of 10 mA/cm.sup.2 was passed through each
of the obtained Organic El Elements 1-1 to 1-15 and each light
emission spectrum was measured using Spectrum Analyzer PMA-11
produced by Hamamatsu Photonics K.K. The results were shown in the
values of CIE chromaticity coordinates.
[0521] The CIE chromaticity coordinate of the white light of the
present invention is preferably (0.28-0.38, 0.28-0.38) and
specifically preferably (0.33, 0.33).
[0522] The results were shown in Table 2. TABLE-US-00004 TABLE 2
CIE Wavelength of chromaticity blue light Emission Luminance
Emission efficiency of white light emission peak Sample while 10 V
while 2.5 mA/cm.sup.2 while 10 while 10 name applied (cd/m.sup.2)
passed (lm/W) mA/cm.sup.2 passed mA/cm.sup.2 passed (nm) Remarks
1-1 37000 9.6 (0.31, 0.33) 448 Inventive 1-2 39000 10.2 (0.33,
0.33) 448 Inventive 1-3 40000 10.5 (0.34, 0.33) 450 Inventive 1-4
37000 9.8 (0.33, 0.33) 450 Inventive 1-5 39000 10.3 (0.33, 0.36)
454 Inventive 1-6 37000 10.9 (0.32, 0.34) 443 Inventive 1-7 38000
10.4 (0.33, 0.35) 445 Inventive 1-8 42000 11.2 (0.35, 0.35) 452
Inventive 1-9 35000 9.2 (0.30, 0.33) 446 Inventive 1-10 38000 10.1
(0.32, 0.33) 445 Inventive 1-11 41000 9.8 (0.35, 0.36) 452
Inventive 1-12 39000 10.1 (0.35, 0.35) 456 Inventive 1-13 25000 5.6
(0.35, 0.36) 450 Comparative 1-14 36000 8.3 (0.38, 0.45) 460
Comparative 1-15 27000 6.8 (0.31, 0.36) 471 Comparative
[0523] It is clear, from Table 2, that the white light emitting
organic EL elements of the present invention each exhibit a high
emission luminance and a high emission efficiency as well as
exhibiting a CIE chromaticity lying in the preferable range. The
element samples in which BDM-1 in element sample 1-1 was replaced
with each of the above described blue light emitting dopants BDM-10
to 45 also exhibited preferable effects.
Example 2
Preparation of White Light Emitting Organic EL Element 2-1
[0524] On a 25 mm.times.25 mm.times.0.5 mm glass substrate, an
indium-tin oxide anode (ITO, indium/tin=95/5 in molar ratio) was
formed via a sputtering method employing a direct current power
source (thickness: 200 nm). The surface resistance of the anode was
10 .OMEGA./sq. On the anode, N,N'-dinaphthyl-N,N'-diphenylbenzidine
(.alpha.-NPD) was deposited by vacuum evaporation with a thickness
of 30 nm as a hole transport layer. After that, host material HM-1
and blue light emitting material BDM-1 were co-deposited in
depositing rates of 3 nm/sec and 0.3 nm/sec, respectively, by
vacuum evaporation to form a first light emission layer having a
thickness of 10 nm. Subsequently, a host material
4,4'-N,N'-dicarbazolebiphenyl (CBP) and green light emitting
material GDM-1 were co-deposited in depositing rates of 3 nm/sec
and 0.5 nm/sec, respectively, by vacuum evaporation to form a
second light emission layer having a thickness of 20 nm. Further, a
host material CBP and red light emitting material RDM-1 were
co-deposited in depositing rates of 3 nm/sec and 0.1 nm/sec,
respectively, by vacuum evaporation to form a third light emission
layer having a thickness of 10 nm.
[0525] After that, a BCP layer having a thickness of 10 nm was
formed as a hole blocking layer.
[0526] Further, an Alq.sub.3 layer having a thickness of 25 nm was
vacuum evaporated to form an electron transport layer. On the
organic compound layers, a patterned mask (a mask to form an
emission area of 5 mm.times.5 mm) was placed, and 0.5 nm thickness
of lithium fluoride layer as a cathode buffer layer and 150 nm
thickness of aluminum layer as the cathode were deposited in a
vacuum evaporation apparatus. Aluminum lead wires were connected to
the anode and the cathode to prepare an emission element. The
emission element was sealed with a glass container using a
UV-curable adhesive (XNR5493, produced by Nagase-Ciba Ltd.) in a
nitrogen-filled glove box to obtain White Light Emitting Organic EL
Element 2-1 of the present invention.
<<Preparation of White Light Emitting Organic EL Elements 2-2
to 2-19>>
[0527] White Light Emitting Organic EL Elements 2-2 to 2-19 each
were prepared in the same manner as White Light Emitting Organic EL
Elements 2-1, except that the materials and layer constitutions
listed in Tables 3-5 were employed.
<<Preparation of GOLED-5 for Measuring Spectral Ratio of
Green Light Emission>>
[0528] In order to use for measuring the spectral ratio of green
light emission of the elements prepared in Example 2 while a
current of 10 mA/cm.sup.2 is passed, GOLED-5 for measuring spectral
ratio of green light emission was prepared as follows.
[0529] On a 25 mm.times.25 mm.times.0.5 mm glass substrate, an
indium-tin oxide anode (ITO, indium/tin=95/5 in molar ratio) was
formed via a sputtering method employing a direct current power
source (thickness: 200 nm). The surface resistance of the anode was
10 .OMEGA./sq. On the anode, .alpha.-NPD was deposited by vacuum
evaporation with a thickness of 30 nm as a hole transport layer.
After that, host material CBP and green light emitting material
GDM-1 were co-deposited in depositing rates of 3 nm/sec and 0.5
nm/sec, respectively, by vacuum evaporation to form a green light
emission layer having a thickness of 40 nm. Subsequently, a BCP
layer having a thickness of 10 nm was formed as a hole blocking
layer. Further, an Alq.sub.3 layer having a thickness of 25 nm was
vacuum evaporated to form an electron transport layer.
[0530] On the electron transport layer, a patterned mask (a mask to
form an emission area of 5 mm.times.5 mm) was placed, and 0.5 nm
thickness of lithium fluoride layer as a cathode buffer layer and
150 nm thickness of aluminum layer as the cathode were deposited in
a vacuum evaporation apparatus. Aluminum lead wires were connected
to the anode and the cathode to prepare an emission element. The
emission element was sealed with a glass container using a
UV-curable adhesive (XNR5493, produced by Nagase-Ciba Ltd.) in a
nitrogen-filled glove box to obtain a green light emitting element
as a comparative sample. The spectral curve of green light emission
obtained from the green light emitting element is shown in FIG.
8.
<<Preparation of GOLED-6 to 8 for Measuring Spectral Ratio of
Green Light Emission>>
[0531] GOLED-6 to 8 for Measuring Spectral Ratio of Green Light
Emission were prepared in the same manner as GOLED-5 except that
materials or green light emission were changed as shown in Table 1.
TABLE-US-00005 TABLE 3 First emission layer Second emission layer
Third emission layer Spectral ratio (material and added (material
and added (material and added of green amount (wt %)) amount (wt
%)) amount (wt %)) emission while Sample Host Emission Host
Emission Host Emission 10 mA/cm.sup.2 name *1 material material *1
material material *1 material material passed (%) Remarks 2-1 20
HM-1 90 BDM-1 10 20 CBP 93 GDM-1 7 20 CBP 85 RDM-1 15 68 Inv. 2-2
30 HM-2 90 BDM-1 10 20 CBP 87 GDM-1 10 -- -- -- 66 Inv. RDM-2 3 2-3
30 HM-1 85 BDM-2 10 20 CBP 85 RDM-1 15 -- -- -- 69 Inv. GDM-1 5 2-4
30 HM-2 85 BDM-2 10 20 CBP 85 RDM-2 15 -- -- -- 70 Inv. GDM-2 5 2-5
30 HM-1 84 BDM-1 10 -- -- -- -- -- -- 66 Inv. GDM-1 4 RDM-1 2 2-6
30 HM-2 84 BDM-2 10 -- -- -- -- -- -- 67 Inv. GDM-1 4 RDM-2 2 2-7
10 HM-3 90 BDM-3 10 10 CBP 87 GDM-3 10 -- -- -- 68 Inv. RDM-1 3 2-8
10 HM-3 85 BDM-4 10 10 CBP 85 RDM-2 15 -- -- -- 65 Inv. GDM-4 5 2-9
20 HM-4 84 BDM-5 10 -- -- -- -- -- -- 70 Inv. GDM-1 4 RDM-1 2 2-10
20 HM-5 84 BDM-6 10 -- -- -- -- -- -- 64 Inv. GDM-2 4 RDM-2 2 *1
Layer thickness (nm) Inv.: Inventive
[0532] TABLE-US-00006 TABLE 4 First emission layer Second emission
layer Third emission layer Spectral ratio (material and added
(material and added (material and added of green amount (wt %))
amount (wt %)) amount (wt %)) emission while Sample Host Emission
Host Emission Host Emission 10 mA/cm.sup.2 name *1 material
material *1 material material *1 material material passed (%)
Remarks 2-11 20 HM-1 84 BDM-7 10 -- -- -- -- -- -- 68 Inv. GDM-1 4
RDM-2 2 2-12 20 HM-2 84 BDM-8 10 -- -- -- -- -- -- 70 Inv. GDM-1 4
RDM-2 2 2-13 20 HM-1 84 BDM-9 10 -- -- -- -- -- -- 65 Inv. GDM-2 4
2-14 20 HM-2 90 RDM-2 2 BDM-9 10 20 CBP 87 GDM-1 10 -- -- -- 70
Inv. RDM-1 3 2-15 30 HM-1 84 BDM-10 10 -- -- -- -- -- -- 68 Inv.
GDM-1 4 RDM-2 2 2-16 30 HM-2 84 BDM-11 10 -- -- -- -- -- -- 69 Inv.
GDM-1 4 RDM-2 2 2-17 20 -- -- BM-1 100 20 CBP 93 GDM-1 7 20 CBP 85
RDM-1 15 65 Comp. 2-18 20 HM-1 90 BD-2 10 20 CBP 93 GDM-1 7 20 CBP
85 RDM-2 15 55 Comp. 2-19 25 HM-1 90 BGD-1 10 -- -- -- 20 CBP 85
RDM-2 15 -- Comp. GOLED-5 30 CBP 93 GDM-1 7 -- -- -- -- -- -- *2
GOLED-6 30 CBP 93 GDM-2 7 -- -- -- -- -- -- *2 GOLED-7 30 CBP 93
GDM-3 7 -- -- -- -- -- -- *2 GOLED-8 30 CBP 93 GDM-4 7 *2 *1 Layer
thickness (nm), *2 Comparative Sample Inv.: Inventive, Comp.:
Comparative
[0533] TABLE-US-00007 TABLE 5 Hole transport Hole blocking Electron
transport layer layer layer Hole Hole Electron Sample Thickness
transport Thickness blocking Thickness transport name (nm) material
(nm) material (nm) layer Remarks 2-1 40 .alpha.-NPD 10 BCP 20
Alq.sub.3 Inv. 2-2 40 .alpha.-NPD 10 BAlq 20 ET-2 Inv. 2-3 40
.alpha.-NPD 10 BAlq 20 Alq.sub.3 Inv. 2-4 40 .alpha.-NPD 10 BAlq 20
ET-2 Inv. 2-5 40 HT-1 10 HB-1 20 Alq.sub.3 Inv. 2-6 40 HT-1 10 HB-1
20 ET-2 Inv. 2-7 40 .alpha.-NPD 10 BAlq 20 Alq.sub.3 Inv. 2-8 40
.alpha.-NPD 10 BAlq 20 Alq.sub.3 Inv. 2-9 40 HT-1 10 HB-1 20
Alq.sub.3 Inv. 2-10 40 HT-1 10 HB-1 20 Alq.sub.3 Inv. 2-11 40 HT-1
10 HB-1 20 Alq.sub.3 Inv. 2-12 40 HT-1 10 HB-1 20 Alq.sub.3 Inv.
2-13 40 HT-1 10 HB-1 20 Alq.sub.3 Inv. 2-14 40 HT-1 10 HB-1 20 ET-2
Inv. 2-15 40 HT-1 10 HB-1 20 Alq.sub.3 Inv. 2-16 40 HT-1 10 HB-1 20
Alq.sub.3 Inv. 2-17 40 .alpha.-NPD -- -- 30 ET-2 Comp. 2-18 40
.alpha.-NPD 10 BCP 20 ET-2 Comp. 2-19 40 .alpha.-NPD 10 BCP 20 ET-2
Comp. GOLED-5 40 .alpha.-NPD 10 BCP 20 Alq.sub.3 *1 GOLED-6 40
.alpha.-NPD 10 BCP 20 Alq.sub.3 *1 GOLED-7 40 .alpha.-NPD 10 BCP 20
Alq.sub.3 *1 GOLED-8 40 .alpha.-NPD 10 BCP 20 Alq.sub.3 *1 *1
Comparative Sample Inv.: Inventive, Comp.: Comparative
[0534] Obtained White Light Emitting Organic EL Elements 2-1 to
2-19 each were evaluated in the same manner as described in Example
1.
[0535] The obtained results are shown in Table 6. TABLE-US-00008
TABLE 6 CIE Wavelength of chromaticity blue light Emission
Luminance Emission efficiency of white light emission peak Sample
while 10 V while 2.5 mA/cm.sup.2 while 10 while 10 name applied
(cd/m.sup.2) passed (lm/W) mA/cm.sup.2 passed mA/cm.sup.2 passed
(nm) Remarks 2-1 71000 13.5 (0.31, 0.33) 447 Inventive 2-2 75000
10.7 (0.33, 0.33) 447 Inventive 2-3 81000 11.0 (0.34, 0.36) 450
Inventive 2-4 83000 14.0 (0.34, 0.35) 450 Inventive 2-5 80000 11.6
(0.33, 0.33) 447 Inventive 2-6 76000 11.9 (0.32, 0.34) 450
Inventive 2-7 76000 12.0 (0.33, 0.33) 449 Inventive 2-8 73000 11.2
(0.34, 0.35) 453 Inventive 2-9 88000 13.6 (0.33, 0.36) 442
Inventive 2-10 86000 10.7 (0.33, 0.35) 445 Inventive 2-11 87000
11.0 (0.33, 0.35) 452 Inventive 2-12 83000 10.5 (0.33, 0.35) 446
Inventive 2-13 79000 10.8 (0.32, 0.34) 445 Inventive 2-14 82000
10.3 (0.30, 0.33) 445 Inventive 2-15 85000 11.1 (0.35, 0.36) 452
Inventive 2-16 83000 10.6 (0.36, 0.36) 446 Inventive 2-17 40000 7.2
(0.35, 0.36) 450 Comparative 2-18 62000 10.3 (0.38, 0.35) 460
Comparative 2-19 58000 8.6 (0.31, 0.33) 471 Comparative
[0536] It is clear, from Table 6, that the white light emitting
organic EL elements of the present invention each exhibit a high
emission luminance and a high emission efficiency as well as
exhibiting a CIE chromaticity lying in the preferable range. The
element samples in which BDM-1 in element sample 1-1 was replaced
with each of the above described blue light emitting dopants BDM-10
to 45 also exhibited preferable effects.
Example 3
Preparation of White Light Emitting Element and White Light
Emitting Illuminator
[0537] Each of the elements prepared in Example 1 or in Example 2
was provided with the sealing container having the same structure
in the same method as in Example 1 to form flat lamps. In FIG. 6 a
schematic illustration of the flat lamp is shown. FIG. 6(a) shows a
schematic illustration of a plain view and FIG. 6(b) shows a
schematic illustration of the cross-section.
[0538] When an electric current was passed through the flat lamp,
almost white light emission was obtained, and it was found that the
flat lamp can be used as an illuminator.
Possibility for the Practical Use
[0539] According to the present invention, obtained were an organic
EL element exhibiting a high emission luminance, a high emission
efficiency and a high purity CIE chromaticity of white light, and a
display and an illuminator employing the above organic EL
element.
* * * * *