U.S. patent application number 15/416032 was filed with the patent office on 2017-07-27 for compound and electronic device including same.
The applicant listed for this patent is Nichem Fine Technology Co., Ltd.. Invention is credited to Chi-Chung Chen, Shwu-Ju SHIEH.
Application Number | 20170213990 15/416032 |
Document ID | / |
Family ID | 59359552 |
Filed Date | 2017-07-27 |
United States Patent
Application |
20170213990 |
Kind Code |
A1 |
SHIEH; Shwu-Ju ; et
al. |
July 27, 2017 |
COMPOUND AND ELECTRONIC DEVICE INCLUDING SAME
Abstract
A compound is disclosed. The compound has a formula of
MA.sub.xL.sub.y, wherein: A is ##STR00001## L is one of
##STR00002## M is a metal having six valence electrons, x is an
integer from 1-3, y is an integer from 0-2, x+y=3, any of
R.sub.a-R.sub.b and R.sub.1-R.sub.3 is independently selected from
a group consisting of hydrogen, deuterium, fluorine, chlorine,
bromine, iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2,
C(.dbd.O)Ar.sup.2, P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of a hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a deuterium, a
halogen, a substituted or unsubstituted alkyl, a substituted or
unsubstituted cycloalkyl and a substituted or unsubstituted
aryl.
Inventors: |
SHIEH; Shwu-Ju; (Hsinchu
County, TW) ; Chen; Chi-Chung; (Hsinchu County,
TW) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Nichem Fine Technology Co., Ltd. |
Hsinchu County |
|
TW |
|
|
Family ID: |
59359552 |
Appl. No.: |
15/416032 |
Filed: |
January 26, 2017 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
62287724 |
Jan 27, 2016 |
|
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L 51/5072 20130101;
H01L 51/0061 20130101; C07C 2603/18 20170501; H01L 51/0058
20130101; C07D 239/74 20130101; C07D 313/06 20130101; H01L 51/0073
20130101; H01L 51/42 20130101; C07D 239/26 20130101; C09K 2211/185
20130101; H01L 51/0057 20130101; C07D 213/22 20130101; C07F 15/0033
20130101; C07D 213/57 20130101; H01L 51/0085 20130101; C09K
2211/1007 20130101; H01L 51/0056 20130101; H01L 51/0072 20130101;
H01L 51/5088 20130101; C07C 255/51 20130101; C07C 2603/98 20170501;
C07D 223/14 20130101; C09K 11/06 20130101; Y02E 10/549 20130101;
H01L 51/006 20130101; C09K 2211/1033 20130101; C07C 2603/99
20170501; H01L 51/5056 20130101; C07D 235/18 20130101; H01L 51/5016
20130101; H01L 51/5096 20130101; C07D 251/24 20130101; C09K
2211/1029 20130101; C07C 211/61 20130101; C07D 213/38 20130101;
C07D 213/06 20130101; H01L 51/0067 20130101; C07D 307/91
20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C07F 15/00 20060101 C07F015/00; C09K 11/06 20060101
C09K011/06 |
Claims
1. A compound having a formula of MA.sub.xL.sub.y, wherein: A is
##STR00091## L is one of ##STR00092## M is a metal having six
valence electrons, x is an integer from 1-3, y is an integer from
0-2, x+y=3, any of R.sub.a-R.sub.b and R.sub.1-R.sub.3 is
independently selected from a group consisting of hydrogen,
deuterium, fluorine, chlorine, bromine, iodine, N(R.sup.1).sub.2,
N(Ar.sup.1).sub.2, C(.dbd.O)Ar.sup.2, P(.dbd.O)Ar.sup.3.sub.2,
S(.dbd.O)Ar.sup.4, S(.dbd.O).sub.2Ar.sup.5,
CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN, NO.sub.2, Si(R.sup.4).sub.3,
B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a linear alkyl having 1 to 40
carbon atoms, a C.sub.1-C.sub.40 alkoxyl, a C.sub.1-C.sub.40
alkylthiol, a C.sub.3-C.sub.40 branched alkyl, a C.sub.3-C.sub.40
cycloalkyl, a C.sub.3-C.sub.40 branched alkoxyl, a C.sub.3-C.sub.40
cyclic alkoxyl, a C.sub.3-C.sub.40 branched alkylthiol and a
C.sub.3-C.sub.40 cyclic alkylthiol, any of R.sup.1-R.sup.6 is one
of a hydrogen and an alkyl, any of Ar.sup.1-Ar.sup.6 is one of a
hydrogen and an aryl, and any of R.sub.4.about.R.sub.11 and
R.sub.13.about.R.sub.15 is independently selected from a group
consisting of a hydrogen, a deuterium, a halogen, a substituted or
unsubstituted alkyl, a substituted or unsubstituted cycloalkyl and
a substituted or unsubstituted aryl.
2. A compound according to claim 1, wherein M is one of platinum
and iridium.
3. A compound according to claim 1, wherein any of R.sub.a-R.sub.b
and R.sub.1-R.sub.3 is independently selected from a group
consisting of a hydrogen, an alkyl having 1 to 4 carbon atoms and
an aryl having 1 to 6 carbon atoms.
4. A compound according to claim 1, wherein any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is one selected
from a group consisting of a hydrogen, a fluorine, a chlorine, a
bromine, an alkyl having 1 to 4 carbon atoms and an aryl having 1
to 6 carbon atoms, and any of R.sup.1-R.sup.6 is one of a hydrogen
and an C1-C6 alkyl.
5. A compound according to claim 4, wherein two adjacent groups of
R.sub.4.about.R.sub.7 are optionally jointed to form a fused
ring.
6. A compound according to claim 5, wherein the fused ring is a
phenyl ring.
7. A compound according to claim 1, wherein any of R.sub.a-R.sub.b,
R.sub.1-R.sub.11 and R.sub.13.about.R.sub.15 is one selected from a
group consisting of a hydrogen, a methyl, an isobutyl, and a
phenyl.
8. A compound according to claim 1, wherein the formula of
MA.sub.xL.sub.y is one selected from a group consisting of the
following formulae 1-1 to 1-17: ##STR00093## ##STR00094##
##STR00095## ##STR00096##
9. A compound according to claim 1, wherein the compound is used as
a material in a light-emitting layer of an organic light emitting
diode (OLED).
10. An electronic device comprising a compound having a formula of
MA.sub.xL.sub.y, wherein: A is ##STR00097## L is one of
##STR00098## M is a metal having six valence electrons, x is an
integer from 1-3, y is an integer from 0-2, x+y=3, any of
R.sub.a-R.sub.b and R.sub.1-R.sub.3 is independently selected from
a group consisting of hydrogen, deuterium, fluorine, chlorine,
bromine, iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2,
C(.dbd.O)Ar.sup.2, P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a halogen, a
substituted or unsubstituted alkyl, a substituted or unsubstituted
cycloalkyl and a substituted or unsubstituted aryl.
11. An electronic device according to claim 10, wherein M is one of
platinum and iridium.
12. An electronic device according to claim 10, wherein, any of
R.sub.a-R.sub.b and R.sub.1-R.sub.3 is independently selected from
a group consisting of a hydrogen, an alkyl having 1 to 4 carbon
atoms and an aryl having 1 to 6 carbon atoms.
13. An electronic device according to claim 10, wherein any of
R.sub.4.about.R.sub.1 and R.sub.13.about.R.sub.15 is one selected
from a group consisting of a hydrogen, a fluorine, a chlorine, a
bromine, an alkyl having 1 to 4 carbon atoms and an aryl having 1
to 6 carbon atoms.
14. An electronic device according to claim 13, wherein two
adjacent groups of R.sub.4.about.R.sub.8 are optionally jointed to
form a fused ring, and the fused ring is a phenyl ring.
15. An electronic device according to claim 10, wherein any of
R.sub.a-R.sub.b, R.sub.1-R.sub.11 and R.sub.13.about.R.sub.15 is
one selected from a group consisting of a hydrogen, a methyl, an
isobutyl and a phenyl.
16. An electronic device according to claim 10, wherein the formula
of MA.sub.xL.sub.y is one selected from a group consisting of the
following formulae 1-1 to 1-17. ##STR00099## ##STR00100##
##STR00101## ##STR00102##
17. An electronic device according to claim 10, wherein the
electronic device is an OLED, and the OLED comprises: a first
electrode; a second electrode; and a light emitting layer disposed
between the first electrode and the second electrode, wherein the
light emitting layer is made of the compound.
18. An electronic device according to claim 17, wherein the
electronic device further comprises an electron transport layer
disposed between the light emitting layer and the first electrode,
an electron injection layer disposed between the electron transport
layer and the first electrode, a hole transport layer disposed
between the light emitting layer and the second electrode, and a
hole injection layer disposed between the hole transport layer and
the second electrode, wherein the first electrode is a cathode and
the second electrode is an anode.
19. An electronic device according to claim 18, wherein any one of
the hole injection layer, the hole transport layer, the light
emitting layer, the electron transport layer, the electron
injection layer and the combination thereof is formed by one of an
evaporation and an ink jet printing method.
20. An electronic device according to claim 10, wherein the
electronic device is used as one selected from a group consisting
of an organic light emitting apparatus, a solar cell apparatus, an
organic transistor, a detection apparatus, a flat panel display, a
computer monitor, a TV, a billboard, a light for interior or
exterior illumination, a signal light for interior or exterior
illumination, a flexible display, a laser printer, a telephone, a
cell phone, a remote control apparatus, a pad computer, a laptop
computer, a digital camera, a camcorder, a viewfinder, a
micro-display, a vehicle electronic apparatus, a large area wall
display, an audio visual screen, a signal apparatus, a theater
screen, a stadium screen, a personal digital assistant (PDA), an
industrial computer, a point of sales (POS) system, a heads-up
display, a fully transparent display and a touch display.
Description
CROSS-REFERENCE TO RELATED APPLICATION AND CLAIM OF PRIORITY
[0001] The application claims the benefit of the U.S. Provisional
Patent Application No. 62/287,724, filed on Jan. 27, 2016, at the
U.S. Intellectual Property Office, the disclosures of which are
incorporated herein in their entirety by reference.
FIELD OF THE INVENTION
[0002] The present invention is related to an organic compound. In
particular, the present invention is related to an organic compound
for use in an electronic device.
BACKGROUND OF THE INVENTION
[0003] It is well known that the organic light emitting diode
(OLED) was initially invented and proposed by the Eastman Kodak
Company through a vacuum evaporation method. Tang and VanSlyke of
the Kodak Company deposited an electron transport material such as
tris(8-hydroxyquinolinato)aluminium (abbreviated as Alq3) on a
transparent indium tin oxide (abbreviated as ITO) glass formed with
an organic layer of aromatic diamine thereon, and subsequently
completed the fabrication of an organic electroluminescent (EL)
device after a metal electrode was vapor-deposited onto the Alq3
layer. The organic EL device has become a new generation lighting
device or display because of high brightness, fast response speed,
light weight, compactness, true color, no difference in viewing
angles, the lack of any LCD backlight plates, and low power
consumption.
[0004] Recently, some interlayers such as an electron transport
layer and a hole transport layer have been added between the
cathode and the anode to increase the current efficiency and power
efficiency of the OLEDs. For example, an OLED 100 shown as FIG. 1
is designed to be formed with a cathode 11, an electron injection
layer 12, an electron transport layer 13, a light emitting layer
15, a hole transport layer 17, a hole injection layer 18, an anode
19 and the a substrate 20.
[0005] In the device function concept, the light emitted by the
OLED 100 results from excitons produced by the recombination of
electrons and holes in the light emitting layer 15, wherein the
formed excitons have configurations with two contrary spin
directions, which include a singlet excited state and a triplet
excited state. Thus, when the two electrons having two contrary
spin directions in each of the electron pairs in the basic state
are excited, about 25% of the excitons transition to the singlet
excited state to form the singlet excitons, and 75% of the excitons
transition to the triplet excited state to form the triplet
excitons. The light generated from the singlet excitons is called
fluorescent light while the light generated from the triplet
excitons is called phosphorescent light.
[0006] So, when a fluorescent material is used as the
light-emitting layer 15 of the OLED 100, about 25% of the excitons
are used to emit light, and the other 75% of the excitons in the
triplet excited state are lost through a non-luminescence
mechanism. For this reason, the general fluorescent material
performs at a maximum quantum yield of 25%, a limit which amounts
to an external quantum efficiency of 5% in the device. If a
phosphorescent material is used as the light-emitting layer 15 of
the OELD 100, the material will be advantageous to perform at a
quantum yield of 75% resulting from the triplet excitons. The
singlet excitons can become triplet excitons through an intersystem
crossing, and accordingly the internal quantum efficiency of the
phosphorescent material will reach 100%. However, when the
above-mentioned two materials are used with the OLED devices, there
will be individual advantages and shortcomings. When a fluorescent
material is used as a material in the OLED devices, the device
lifetime will be long but the light emitting efficiency is low, and
when a phosphorescent material is used, the light emitting
efficiency is high but the device lifetime is short.
[0007] Therefore, to enhance the OLED devices having the advantages
of both good light efficiency and long lifetime, research has been
conducted to introduce heavy atoms such as the transition metals,
e.g. Ir, Pt, Os, Ru, Eu, Re, etc., into the fluorescent materials
in the light emitting layer. Using the heavy atom effect to
generate the spin-orbital coupling, the probability of
transitioning the excitons from the basic state to the triplet
state in the system is improved. Accordingly, the internal quantum
efficiency in the OLED devices can reach 100%.
[0008] In addition, in subsequent studies, it was found that, by
doping impurities in different concentrations in the light emitting
layer in the OLED devices, the transition of the energy of the
light emitting host materials to the dopants to change the colors
of the light emitting materials and the light emitting efficiency
are achieved, so that OLED devices emitting the three colors of
red, green and blue light are obtained. These studies
simultaneously pointed out the importance of the selection of the
materials used in various layers in the OLED devices, where the
materials include hole transport materials, electron transport
materials, host light emitting materials and dopants for different
colors of the light. In addition, it will not be possible to meet
the requirements unless continuous research and improvements to the
physical properties of the materials themselves such as the energy
gap, thermal properties, and morphology are accomplished.
[0009] Although there are a lot of dopant materials related to
emitting the three primary colors red, green and blue, no suitable
solution has been reached. Therefore, the inventors of the present
invention undertook their best efforts to perform the inventive
research and disclosed herein a series of dibenzoxepin pyridine
complexes of metal having six covalent electrons and being the
central atom, as green light emitting dopant materials used for a
light emitting layer in OLED devices.
SUMMARY OF THE INVENTION
[0010] In accordance with one aspect of the present invention, a
compound is disclosed. The compound has a formula of
MA.sub.xL.sub.y, wherein:
A is
##STR00003##
[0011] L is one of
##STR00004##
[0012] M is a metal having six valence electrons, x is an integer
from 1-3, y is an integer from 0-2, x+y=3, any of R.sub.a-R.sub.b
and R.sub.1-R.sub.3 is independently selected from a group
consisting of hydrogen, deuterium, fluorine, chlorine, bromine,
iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2, C(.dbd.O)Ar.sup.2,
P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of a hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a deuterium, a
halogen, a substituted or unsubstituted alkyl, a substituted or
unsubstituted cycloalkyl and a substituted or unsubstituted
aryl.
[0013] In accordance with another aspect of the present invention,
an electronic device made using a compound is disclosed. The
electronic device includes a compound having a formula of
MA.sub.xL.sub.y, wherein:
A is
##STR00005##
[0014] L is one of
##STR00006##
[0015] M is a metal having six valence electrons, x is an integer
from 1-3, y is an integer from 0-2, x+y=3, any of R.sub.a-R.sub.b
and R.sub.1-R.sub.3 is independently selected from a group
consisting of hydrogen, deuterium, fluorine, chlorine, bromine,
iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2,
P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a deuterium, a
halogen, a substituted or unsubstituted alkyl, a substituted or
unsubstituted cycloalkyl and a substituted or unsubstituted
aryl.
[0016] When the compounds disclosed in the present invention are
used as the materials in the electronic device, it is possible to
operate the electronic device at a low operation voltage, so that
the electronic device has an increased lifetime and has an
excellent light emitting efficiency.
[0017] The above objectives and advantages of the present invention
will become more readily apparent to those ordinarily skilled in
the art after reviewing the following detailed descriptions and
accompanying drawings.
BRIEF DESCRIPTION OF THE DRAWINGS
[0018] FIG. 1 is an OLED structure according to prior art;
[0019] FIGS. 2 and 3 are NMR spectrums of compounds of the
nitrogen-substituted dibenzoxepinpyridine according to the present
invention;
[0020] FIGS. 4-7 are NMR spectrums of compounds of the dibenzoxepin
pyridine complexes of metal having six covalent electrons and being
the central atom according to the present invention; and
[0021] FIG. 8 is an OLED structure according to one embodiment of
the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
[0022] The present invention will now be described more
specifically with reference to the following embodiments. It is to
be noted that the following descriptions of preferred embodiments
of this invention are presented herein for the purposes of
illustration and description only; they are not intended to be
exhaustive or to be limited to the precise form disclosed.
[0023] The present invention discloses a compound being a metal
complex with at least one dibenzoxepin pyridine ligand or its
derivatives, wherein the compound has a formula of MA.sub.xL.sub.y,
wherein:
A is
##STR00007##
[0024] L is one of
##STR00008##
[0025] M is a metal having six valence electrons, x is an integer
from 1-3, y is an integer from 0-2, x+y=3, any of R.sub.a-R.sub.b
and R.sub.1-R.sub.3 is independently selected from a group
consisting of hydrogen, deuterium, fluorine, chlorine, bromine,
iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2, C(.dbd.O)Ar.sup.2,
P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of a hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a deuterium, a
halogen, a substituted or unsubstituted alkyl, a substituted or
unsubstituted cycloalkyl and a substituted or unsubstituted
aryl.
[0026] Preferably, M is one of iridium and platinum, any of
R.sub.a-R.sub.b and R.sub.1-R.sub.3 is independently selected from
a group consisting of a hydrogen, an alkyl having 1 to 4 carbon
atoms and an aryl having 1 to 6 carbon atoms, and any of
R.sup.1-R.sup.6 is one of a hydrogen and an C1-C6 alkyl, any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is one selected
from a group consisting of a hydrogen, a deuterium, a fluorine, a
chlorine, a bromine, an alkyl having 1 to 4 carbon atoms and an
aryl having 1 to 6 carbon atoms, two adjacent groups of
R.sub.4.about.R.sub.7 are optionally jointed to form a fused ring,
and the fused ring is a phenyl ring.
[0027] More preferably, any of R.sub.a-R.sub.b, R.sub.1-R.sub.11
and R.sub.13.about.R.sub.15 is one selected from a group consisting
of a hydrogen, a methyl, an isobutyl and a phenyl, and any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an phenyl.
[0028] The compound of a metal complex with at least one
dibenzoxepin pyridine ligand or its derivatives possess a light
emitting property, and has a property to transition the excitons
from the singlet excited state into the triplet excited state.
Thus, when the compound or its derivatives are used for a
phosphorescent OLED device, the compound is used as a material of a
light emitting layer.
[0029] The compound of a metal complex with at least one
dibenzoxepin pyridine ligand or its derivatives is represented by
the following Formula 1-0 and Formula 2-0:
##STR00009##
wherein M is iridium or platinum, x is an integer from 1-3, any of
R.sub.a-R.sub.b and R.sub.1-R.sub.3 is independently selected from
a group consisting of hydrogen, deuterium, fluorine, chlorine,
bromine, iodine, N(R.sup.1).sub.2, N(Ar.sup.1).sub.2,
C(.dbd.O)Ar.sup.2, P(.dbd.O)Ar.sup.3.sub.2, S(.dbd.O)Ar.sup.4,
S(.dbd.O).sub.2Ar.sup.5, CR.sup.2.dbd.CR.sup.3Ar.sup.6, CN,
NO.sub.2, Si(R.sup.4).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.6, a
linear alkyl having 1 to 40 carbon atoms, a C.sub.1-C.sub.40
alkoxyl, a C.sub.1-C.sub.40 alkylthiol, a C.sub.3-C.sub.40 branched
alkyl, a C.sub.3-C.sub.40 cycloalkyl, a C.sub.3-C.sub.40 branched
alkoxyl, a C.sub.3-C.sub.40 cyclic alkoxyl, a C.sub.3-C.sub.40
branched alkylthiol and a C.sub.3-C.sub.40 cyclic alkylthiol, any
of R.sup.1-R.sup.6 is one of a hydrogen and an alkyl, any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an aryl, and any of
R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is independently
selected from a group consisting of a hydrogen, a halogen, a
deuterium, a substituted or unsubstituted alky, a substituted or
unsubstituted cycloalkyl 1 and a substituted or unsubstituted
aryl.
[0030] Preferably, A is the compound of the dibenzoxepinpyridine
and the derivatives thereof and can be one selected from the group
consisting of the following.
##STR00010##
[0031] Preferably, any of R.sub.a-R.sub.b and R.sub.1-R.sub.3 is
independently selected from a group consisting of a hydrogen, an
alkyl having 1 to 4 carbon atoms and an aryl having 1 to 6 carbon
atoms, and any of R.sup.1-R.sup.6 is one of a hydrogen and an C1-C6
alkyl, any of R.sub.4.about.R.sub.11 and R.sub.13.about.R.sub.15 is
one selected from a group consisting of a hydrogen, a deuterium, a
fluorine, a chlorine, a bromine, an alkyl having 1 to 4 carbon
atoms and an aryl having 1 to 6 carbon atoms, two adjacent groups
of R.sub.4.about.R.sub.7 are optionally jointed to form a fused
ring, and the fused ring is a phenyl ring.
[0032] More preferably, any of R.sub.a-R.sub.b, R.sub.1-R.sub.11
and R.sub.13.about.R.sub.15 is one selected from a group consisting
of a hydrogen, a methyl, an isobutyl and a phenyl, and any of
Ar.sup.1-Ar.sup.6 is one of a hydrogen and an phenyl.
[0033] More preferably, when L is represented by the following
formula,
##STR00011##
L can be one selected from a group consisting of the following
ligands.
##STR00012## ##STR00013##
And when L is represented by the following formula,
##STR00014##
L can be one selected from a group consisting of the following
ligands.
##STR00015##
[0034] Take the compound represented by Formula 1-0 as an example,
the compound includes the combinations of the following A and L
selected from the followings.
##STR00016## ##STR00017## ##STR00018##
[0035] According to a first embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-1.
##STR00019##
[0036] According to a second embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-2.
##STR00020##
[0037] According to a third embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-3.
##STR00021##
[0038] According to a fourth embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-4.
##STR00022##
[0039] According to a fifth embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-5.
##STR00023##
[0040] According to a sixth embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-6.
##STR00024##
[0041] According to a seventh embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-7.
##STR00025##
[0042] According to a eighth embodiment of the present invention,
the compound of a metal complex with one dibenzoxepin pyridine
ligand is represented by Formula 1-8.
##STR00026##
[0043] According to a ninth embodiment of the present invention,
the compound of a metal complex with one dibenzoxepin pyridine
ligand is represented by Formula 1-9.
##STR00027##
[0044] According to a tenth embodiment of the present invention,
the compound of a metal complex with three dibenzoxepin pyridine
ligands is represented by Formula 1-10.
##STR00028##
[0045] According to an eleventh embodiment of the present
invention, the compound of a metal complex with two dibenzoxepin
pyridine ligands is represented by Formula 1-11.
##STR00029##
[0046] According to a twelfth embodiment of the present invention,
the compound of a metal complex with two dibenzoxepin pyridine
ligands is represented by Formula 1-12.
##STR00030##
[0047] According to a thirteenth embodiment of the present
invention, the compound of a metal complex with two dibenzoxepin
pyridine ligands is represented by Formula 1-13.
##STR00031##
[0048] According to a fourteenth embodiment of the present
invention, the compound of a metal complex with two dibenzoxepin
pyridine ligands is represented by Formula 1-14.
##STR00032##
[0049] According to a fifteenth embodiment of the present
invention, the compound of a metal complex with two dibenzoxepin
pyridine ligands is represented by Formula 1-15.
##STR00033##
[0050] According to a sixteenth embodiment of the present
invention, the compound of a metal complex with two a dibenzoxepin
pyridine ligands is represented by Formula 1-16.
##STR00034##
[0051] According to a seventeenth embodiment of the present
invention, the compound of a metal complex with two dibenzoxepin
pyridine ligands is represented by Formula 1-17.
##STR00035##
[0052] The iridium in each of the above Formulae can be replaced
with platinum. A variety of substituted or unsubstituted compounds
of a metal complex with a dibenzoxepinpyridine belong to the scope
covered by the present invention, and can be synthesized using the
following steps.
Synthesis Method of the First to the Seventeenth Embodiments
[0053] The synthesis method of the compound of an iridium complex
with a dibenzoxepinpyridine includes the following steps.
1. Preparation of a Nitrogen (N)-Substituted Tribenzoxepin (TBO)
Ligand
[0054] 1.1 The synthesis method of the N-substituted TBO ligand
includes the following steps.
[0055] 100 g (1 eq) of diphenyl ether (represented by Formula a)
and n-butyl lithium (n-BuLi) anhydrous tetrahydrofuran (THF) are
put in a 2 L reacting flask, and 587 mL of 2.5M N-butyl lithium is
added to the reacting flask at a temperature of -78.degree. C. to
form a first solution, and then the temperature of the first
solutions is raised to 25.degree. C. and the first solutions reacts
for 24 hours to obtain a semi-product. After the semi-product is
cooled to a temperature of -40.degree. C., trimethyl borate
(B(OMe).sub.3) is added to form a second solution. After its
temperature is raised to 25.degree. C., 3N hydrochloric acid is
added to the second solution until the solution becomes acidic, to
produce 60 g of the compound represented by Formula b. Yield is
52%. The chemical reaction is as follows.
##STR00036##
[0056] 50 g (1 eq) of the compound represented by Formula b and
60.4 g (1 eq) of 2,3-dibromopyridine are put in a 1000 mL reacting
flask, and then 500 mL of isobutanol, 274 g of Cs.sub.2O.sub.3 and
50 mL of water are added. After removing the air from the reaction
flask by vacuum, 3.5 g of tris(dibenzylideneacetone)dipalladium
(Pd.sub.2(dba).sub.3) and 2.22 g of tri-tert-butylphosphonium
tetrafluoroborate (P(t-Bu).sub.3HBF.sub.4) are added and react at a
temperature of 100.degree. C. for 4 hours After being cooled, 200
mL of water is added to terminate the reaction. 600 mL of ethyl
acetate are used to extract the semi-product. After the organic
solvent layer is dried by vacuum, the semi-product is
chromatographed through the silica gel column, and is eluted by
solvent including N-butane and ethyl acetate in a ratio of 3:1.
After the solvents are dried by vacuum, the solvent including
N-butane and ethyl acetate is used to crystallize the product to
obtain 45 g of a yellowish solid, which is the compound represented
by Formula c. Yield is 72% The chemical reaction is as follows.
##STR00037##
[0057] 1.2 Using the same synthesis method and replacing 60.4 g of
2,3-dibromopyridine with 64 g of 2,3-dibromo-4-methyl pyridine or
64 g of 2,3-dibromo-5-methyl pyridine, the compound represented by
Formula d-1 or d-2 is obtained. The chemical reaction is as
follows.
##STR00038##
[0058] 1.3 Using the same synthesis method and replacing 60.4 g of
2,3-dibromopyridine with 69.2 g of 2,3-dibromo-5-chloropyridine,
the compound represented by Formula e is obtained. The chemical
reaction is as follows.
##STR00039##
[0059] 1.4 Instead, 30 g (1 eq) of the compound represented by
Formula e and 13.1 g (1 eq) of phenylboric acid are added to a 1 L
reaction flask, 200 mL of toluene and 20 mL of ethanol are added,
and then 3 eq. of K.sub.2CO.sub.3 aqueous solution (which is 44.5 g
of K.sub.2CO.sub.3 dissolved in 120 mL of water) are added. After
removing the air from the reaction flask by vacuum, 0.602 g of
Pd(OAc).sub.2 and 3.76 g of dicyclohexylphosphino)biphenyl
(P(Cy).sub.2(2-biphenyl)) are added under a nitrogen atmosphere,
the solution is heated and refluxed t at a temperature of
100.degree. C. for 12 hours. It is cooled after the reaction is
terminated. After the organic solvent layer is dried by vacuum, the
semi-product is eluted by solvent including N-butane and ethyl
acetate in a ratio of 3:1, and is chromatographed and purified
through the silica gel column. The compound represented by Formula
f is obtained. The chemical reaction is as follows.
##STR00040##
[0060] The compounds represented by Formula c, Formula d-1, Formula
d-2, Formula e and Formula f are all N-substituted TBO ligands. In
addition, bromine in the reactant 2,3-dibromopyridine can be
replaced by the other halogen elements, so that 2,3-diiodopyridine
can also be a candidate as a reactant. Moreover, it can be seen
from the above chemical reactions that, if an iridium complex with
at least one dibenzoxepin pyridine ligand having a substituted
group on the pyridinyl group contained in the dibenzoxepin pyridine
ligand, then the 4th, 5th, or 6th position on the reactant
2,3-dibromopyridine (or 2,3-diiodopyridine instead) should be
substituted by a prior substitution reaction.
2. Preparation of an Iridium Dimer
2.1 Preparation of N-Substituted TBO Iridium Dimer
[0061] Taking the compound of the N-substituted TBO ligand (N-TBO)
represented by Formula c as an example, the synthesis method of the
N-substituted TBO iridium dimer includes the following steps.
[0062] 10 g (1 eq) of iridium (III) chloride and 16.7 g (2.2 eq) of
N-TBO ligand are added in a 250 mL round bottomed flask. 120 mL of
2-ethoxyethanol and 40 mL water are then added. The mixture is
refluxed for 24 hrs at a temperature of 120.degree. C. under a
nitrogen atmosphere to form the product. After cooling to room
temperature, the product is washed using methanol and is filtered
to obtain the precipitate. The precipitate is dried in vacuum, and
17 g of the N-substituted iridium dimer represented by Formula g is
obtained. Yield is 83.7%. The chemical reaction is as follows.
##STR00041##
2.2 Preparation of Ir(2-phenylpyridine).sub.2 dimer
(Ir(ppy).sub.2Cl dimer)
[0063] 50 g (1 eq) of iridium (III) chloride and 52.8 g (2.4 eq) of
2-phenylpyridine are added in a 1000 mL round bottomed flask. 300
mL of 2-ethoxyethanol and 100 mL water are then added. The mixture
is refluxed for 24 hrs at a temperature of 120.degree. C. under a
nitrogen atmosphere to form the product. After cooling to room
temperature, the product is washed using methanol and is filtered
to obtain the precipitate. The precipitate is dried in vacuum, and
68 g of the Ir(ppy).sub.2Cl dimer represented by Formula h is
obtained. Yield is 89%. The chemical reaction is as follows.
##STR00042##
3. Preparation of an Iridium Trifluoromethanesulfonate (Iridium
Triflate)
[0064] 3.1 Dissolve 5.0 g of the compound represented by Formula g
in 100 mL of dichloromethane (CH.sub.2Cl.sub.2) to form a first
solution. Dissolve 1.97 g of silver triflate (AgOTf) in 20 mL of
methanol to form a second solution. Add the second solution to the
first solution at a temperature of 0.degree. C. to form a mixture.
The mixture is stirred at room temperature for 6 hours. The mixture
is then poured through a celite plug to remove silver chloride
(AgCl) to form a third solution. The solvent contained in the third
solution is evaporated by vacuum, and 5.2 g of the iridium triflate
compound represented by Formula i is obtained. The chemical
reaction is as follows.
##STR00043##
[0065] 3.2 Dissolve 5.0 g of the compound represented by Formula h
in 100 mL of dichloromethane (CH.sub.2Cl.sub.2) to form a first
solution. Dissolve 2.63 g of silver triflate (AgOTf) in 20 mL of
methanol to form a second solution. Add the second solution to the
first solution at a temperature of 0.degree. C. to form a mixture.
The mixture is stirred at room temperature for 6 hours. The mixture
is then poured through a celite plug to remove silver chloride
(AgCl) to form a third solution. The solvent contained in the third
solution is evaporated by vacuum, and 5.9 g of the iridium triflate
compound represented by Formula j is obtained. The chemical
reaction is as follows.
##STR00044##
4. Preparation of the Iridium Complex with at Least One
Dibenzoxepin Pyridium Ligand
[0066] 4.1 Dissolve 5 g (1 eq) of the compound represented by
Formula g, 3.5 g (10 eq) of acetyl acetate (acac) and 9.6 g (20 eq)
of potassium carbonate (K.sub.2CO.sub.3) in 100 mL of
2-ethoxyethanol and react for at a temperature of 80.degree. C. for
24 hours. After being cooled and filtered by a vacuum filter, the
product is eluted with water and methanol, and is dried by vacuum,
to obtain a yellowish solid. The yellowish solid is dissolved and
poured through a celite filter and is washed with CH.sub.2Cl.sub.2
to obtain a semi-product. CH.sub.2Cl.sub.2 is removed from the
semi-product by vacuum, to obtain the iridium complex with two
dibenzoxepin pyridine ligands represented by Formula 1-12. The
chemical reaction is as follows.
##STR00045##
[0067] In a 250 mL round bottomed flask, dissolve 5 g of the
compound represented by Formula g and 1.3 g (2.4 eq) of
2-phenylpyridine in 100 mL of 2-ethoxy ethanol to form a solution.
React the solution at a temperature of 80.degree. C. for 24 hours
to form a mixture. The mixture is then poured onto a celite bed and
the product is eluted using CH.sub.2Cl.sub.2. The CH.sub.2Cl.sub.2
contained in the product is evaporated by vacuum, and 3.2 g of the
compound represented by Formula 1-1 is obtained. The yield is 55%.
The chemical reaction is as follows.
##STR00046##
[0068] 4.3 Alternatively, add and dissolve 5 g (1 eq) of the
compound represented by Formula g and 1.3 g (1.2 eq) of
2-phenylpyridine in 100 mL 2-ethoxyethanol in a 250 mL round
bottomed flask to react at a temperature of 80.degree. C. for 24
hours to obtain the product. Use vacuum distillation to remove the
2-ethoxyethanol solvent, and add methanol to obtain a solid
mixture. The solid mixture is dissolved in dichloroethane
(CH.sub.2Cl.sub.2) and the solution is poured through a celite
filter and is eluted with CH.sub.2Cl.sub.2 to obtain a
semi-product. CH.sub.2Cl.sub.2 is removed from the semi-product by
vacuum, and 100 mL of N-hexane is added to elute all solid
composition. The solid composition is dried by vacuum, and is
dissolved in CH.sub.2Cl.sub.2 and elute the product by
CH.sub.2Cl.sub.2 solvent by a silica column. After removing the
solvent, 3.2 g of the yellowish-orange solid, which is the compound
represented by Formula 1-1, are obtained. Yield is 55%. The
chemical reaction is as follows.
##STR00047##
[0069] 4.4 If the reactant 2-phenylpyridine is replaced by the
compound represented in the following reaction, using similar
reaction steps, the compound represented by Formula 1-10, Formula
1-2, Formula 1-3 or Formula 1-4 will be respectively obtained. The
chemical reactions are as follows.
##STR00048##
[0070] 4.5 Alternatively, in a 250 mL round bottomed flask,
dissolve 5 g (1 eq) of the compound represented by Formula j and
2.9 g (1.2 eq) of the compound represented by Formula c in 100 mL
of 2-ethoxy ethanol to form a solution. React the solution at a
temperature of 80.degree. C. for 24 hours to form a mixture. The
mixture is then poured onto a celite bed and the product is eluted
using CH.sub.2Cl.sub.2. The CH.sub.2Cl.sub.2 contained in the
product is evaporated by vacuum, and the compound represented by
Formula 1-8 is obtained. The chemical reaction is as follows.
##STR00049##
[0071] Table 3 shows several compounds as examples of the iridium
complexes with at least one dibenzoxepinpyridine having
combinations of different ligands A and L, but it is not limited to
the examples in Table 3. These compounds can also be synthesized
using the above steps.
TABLE-US-00001 TABLE 3 ##STR00050## ##STR00051## ##STR00052##
##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057##
##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062##
##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067##
##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072##
##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077##
##STR00078## ##STR00079## ##STR00080## ##STR00081##
[0072] General Purification Method
[0073] The iridium complexes with at least one dibenzoxepin
pyridine ligand are purified by heating with zone refine
sublimation in a vacuum environment of 10.sup.-6 torr.
[0074] It can be seen from the above descriptions that all the
N-substituted dibenzoxepinpyridine compounds and the iridium
complexes with at least one dibenzoxepinpyridine are within the
scope of the present invention. In addition, several N-substituted
dibenzoxepinpyridine compounds and iridium complexes with at least
one dibenzoxepinpyridine synthesized in the present invention were
analyzed by a nuclear magnetic resonance (NMR) spectrometer to
identify their structures. The spectrum diagrams of the compounds
represented by Formulae c, d-1, 1-8, 1-1 and 1-12 synthesized in
the present invention are sequentially shown in FIGS. 2-7.
Accordingly, the obtained compounds are confirmed as the
N-substituted dibenzoxepinpyridine compounds or the iridium
complexes with at least one dibenzoxepinpyridine.
[0075] OLED Device
[0076] The steps to manufacture an OLED device using the iridium
complexes with at least one dibenzoxepinpyridine of the present
invention are as follows.
[0077] Pretreatment to the Substrate
[0078] First, dipping an ITO glass substrate having a thickness of
1500 .ANG. of the ITO layer in distilled water containing a
detergent (supplied by Fischer Co.). The ITO glass substrate is
washed using ultrasonic for 30 minutes, washed twice by distilled
water using ultrasonic for 10 minutes each time, washed with
isopropanol, acetone, and methanol solvents using ultrasonic, and
dried with nitrogen gas. The dried ITO glass substrate is then put
in an oxygen plasma cleaner to treat the surface of the ITO glass
substrate using oxygen plasma for 5 minutes to clean the surface,
so as to increase the work function of the ITO glass surface.
[0079] Coating of the Organic Layer
[0080] The treated ITO glass substrate is placed in a vacuum
evaporation machine and a variety of organic materials are
sequentially deposited on the ITO glass substrate, to manufacture
the OLED device.
[0081] It is possible to use an ink jet printing method to replace
the evaporation method. The variety of organic materials are coated
on the ITO glass substrate using an ink-jet printer, and then are
hardened using a baking process to manufacture the OLED device. If
the ink-jet printing method is used, the consumption of the organic
materials will be much less than when using the evaporation method.
Thus the material cost to manufacture the OLED electronic device is
dramatically reduced.
[0082] Alternatively, it is possible to use an aluminum coated
glass as a substrate to manufacture the OLED device. After cleaning
the substrate, an evaporation or ink jet printing method is used to
coat a variety of the organic materials in a coating sequence that
is reverse of the order mentioned above to manufacture the OLED
device.
[0083] Evaluation to the OLED Device
[0084] FIG. 8 is a structure of an OLED device 200 manufactured
according to the disclosures in the present invention. As shown in
FIG. 8, it includes, from bottom to top, an ITO (as an anode) layer
29 coated on a glass substrate 30, a hole injection layer 28, which
includes a first hole injection (HI-1) layer 28-1 and a second hole
injection (HI-2) layer 28-2 containing a hole injection dopant
(HID) material therein, a hole transport layer 27, which including
a first hole transport (HT-1) layer 27-1 and a second hole
transport (HT-2) layer 27-2, a light emitting layer 25, which
contains a green light emitting host (GH1) material and a green
light emitting dopant (GD) material, an electron transport (ETL)
layer 23 containing an electron transport dopant (ETD) material, an
electron injection (EI) layer 22, and a cathode 21. If necessary, a
hole block layer (not shown) can be disposed between the light
emitting layer 25 and the electron transport layer 23, or an
electron block layer (not shown) can be disposed between the light
emitting layer 25 and the hole transport layer 27. The material and
thickness of each layer used in the OLED devices for the evaluation
are shown in Table 4. Table 5 further shows the formulae of the
materials.
TABLE-US-00002 TABLE 4 layer dopant green host green dopant dopant
hole hole in hole hole hole in light in light electron in hole Hole
transport injection injection transport transport emitting emitting
transport transport injection anode layer 1 layer 2 layer 2 layer 1
layer 2 layer layer layer layer layer cathode material ITO HAT HI-2
HAT HT-1 HT-2 GH Formula ETL Liq Liq Al 1-1, 1-8, 1-12, 1-13 or
1-15 thickness 1500 100 1235 65 100 100 360 40 227.5 122.5 15 1500
(.ANG.) coating -- 1 2 2 3 4 5 5 6 6 7 8 sequence
TABLE-US-00003 TABLE 5 ##STR00082## (HAT) HI-1 ##STR00083## HI-2
##STR00084## HT-1 ##STR00085## HT-2 ##STR00086## GH Compound
represented GD by Formula 1-1, 1-8, 1-12, 1-13 or 1-15 ##STR00087##
ETL ##STR00088## (Liq) ETD
[0085] Table 6 shows the evaluation results of the OLED devices,
which include Examples 1-8 using the compounds represented by
Formula 1-1, 1-8, 1-12, 1-13 and 1-15, and the Comparative Examples
1-2 using the previous compounds. It can be seen from Table 6 that
for the OLED devices using the compounds represented by Formula
1-1, 1-8, 1-12, 1-13 and 1-15 of the present invention, the current
efficiency reaches up to the range of 65.2-78.7 cd/A, and the
operation voltage is only in the 2.87-3.21 V range. In comparison,
the OLED devices using the prior materials in Comparative Examples
1-2, the current efficiency can only reach the range of 63.6-66.2
cd/A, and the operation voltage is in the range of 2.95-3.0V. It
can be seen that the OLED device using the metal complex with at
least one dibenzoxepinpyridine ligand, in which the metal is a
central atom having six covalent electrons as a dopant for the
green light emitting layer, has a higher current efficiency and a
low operation voltage and comparable chroma values for the green
color. Moreover, due to the low operation voltage, it is assured
that the light emitting material has a longer life time and the
OLED device use substantially less power.
TABLE-US-00004 TABLE 6 at 1000 nits Compound, chroma, CIE Operation
current represented system voltage efficiency Example by color ( x,
y ) (V) (cd/A) 1 Formula green ( 0.356, 0.609) 3.01 78.7 1-1 2
Formula green (0.350, 0.611) 2.91 75.5 1-8 3 Formula green ( 0.361,
0.615) 2.87 70.8 1-12 4 Formula green (0.345, 0.617) 3.06 68.5 1-13
5 Formula green (0.348, 0.620) 3.21 65.2 1-15 Comparative Formula
green (0.308, 0.629) 3.0 63.6 Example 1 A-1 Comparative Formula
green (0.314, 0.630) 2.95 66.2 Example 2 A-2 ##STR00089##
##STR00090##
[0086] Each of the electronic devices mentioned above can be
applied to any device or apparatus having a display, such as one
selected from a group consisting of an organic light emitting
apparatus, a solar cell apparatus, an organic transistor, a
detection apparatus, a computer monitor, a TV, a billboard, a light
for interior or exterior illumination, a signaling light for
interior or exterior illumination, a flexible display, a laser
printer, a telephone, a cell phone, a remote control apparatus, a
pad computer, a laptop computer, a digital camera, a camcorder, a
viewfinder, a micro-display, a vehicle electronic apparatus, a
large area wall display, a theater screen, a stadium screen, a
signaling apparatus, a personal digital assistant (PDA), a laptop
computer, an industrial computer, a point of sales (POS), a
heads-up display, a fully transparent display, and a touch
display.
[0087] While the invention has been described in terms of what is
presently considered to be the most practical and preferred
embodiments, it is to be understood that the invention needs not be
limited to the disclosed embodiments. On the contrary, it is
intended to cover various modifications and similar arrangements
included within the spirit and scope of the appended claims, which
are to be accorded with the broadest interpretation so as to
encompass all such modifications and similar structures.
* * * * *