U.S. patent application number 11/179573 was filed with the patent office on 2006-10-12 for silicon-contained anthracene compound for organic electroluminescent device.
Invention is credited to Fan-Hsiu Chang, Chia-Liang Tai, Chen-Ping Yu.
Application Number | 20060226768 11/179573 |
Document ID | / |
Family ID | 37082550 |
Filed Date | 2006-10-12 |
United States Patent
Application |
20060226768 |
Kind Code |
A1 |
Yu; Chen-Ping ; et
al. |
October 12, 2006 |
Silicon-contained anthracene compound for organic
electroluminescent device
Abstract
This invention is about anthracene, at least one having silyl
substituted group on ring 9 and 10, the anthracene can be a organic
light emitting diodes(OLED) material and used for organic
electroluminescent device. ##STR1## wherein X is an triarylsilyl
group having 6 to 20 carbon atoms, an trialkylsilyl group having 1
to 12 carbon atoms, a substituted or unsubsituted aryl group having
6 to 20 carbon atoms, a substituted or unsubsituted heteroaryl
group having 2 to 20 carbon atoms, or a substituted or unsubsituted
alkyl group having 1 to 12 carbon atoms. R.sub.1 and R.sub.2 is
independently a hydrogen, halogen, or a substituted or unsubsituted
alkyl group having 1 to 12 carbon atoms. R.sub.3 to R.sub.5 is
independently a substituted or unsubsituted aryl group having 6 to
20 carbon atoms, or a substituted or unsubsituted alkyl group
having 1 to 12 carbon atoms.
Inventors: |
Yu; Chen-Ping; (Hsin-Chu,
TW) ; Tai; Chia-Liang; (Hsin-Chu, TW) ; Chang;
Fan-Hsiu; (Hsin-Chu, TW) |
Correspondence
Address: |
ROSENBERG, KLEIN & LEE
3458 ELLICOTT CENTER DRIVE-SUITE 101
ELLICOTT CITY
MD
21043
US
|
Family ID: |
37082550 |
Appl. No.: |
11/179573 |
Filed: |
July 13, 2005 |
Current U.S.
Class: |
313/504 ;
556/489 |
Current CPC
Class: |
H05B 33/14 20130101;
H01L 51/0072 20130101; H01L 51/0052 20130101; C09K 2211/1055
20130101; C07F 7/081 20130101; C07F 7/0805 20130101; C09K 2211/1007
20130101; H01L 51/008 20130101; C09K 2211/1014 20130101; H01L
51/5012 20130101; H01L 51/0094 20130101; C09K 11/06 20130101; C09K
2211/1029 20130101; C09K 2211/1011 20130101; H01L 51/0054
20130101 |
Class at
Publication: |
313/504 ;
556/489 |
International
Class: |
C07F 7/08 20060101
C07F007/08; H01J 1/62 20060101 H01J001/62 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 8, 2005 |
TW |
094111260 |
Claims
1. An anthracene compound, at least one having a substituted silyl
group on position 9 and 10, the anthracence compound represented by
the following formula: ##STR12## wherein X represents a substituted
silyl group, a substituted or unsubsituted aryl group having 6 to
20 carbon atoms, a substituted or unsubsituted heteroaryl group
having 2 to 20 carbon atoms, or a substituted or unsubsituted alkyl
group having 1 to 20 carbon atoms; each R.sub.1 and R.sub.2
represents hydrogen, halogen, or a substituted or unsubsituted
alkyl group having 1 to 20 carbon atoms, R.sub.1 and R.sub.2 can be
the same or not the same; and each R.sub.3, R.sub.4 and R.sub.5
represents a substituted or unsubsituted aryl group having 6 to 20
carbon atoms, or a substituted or unsubsituted alkyl group having 1
to 12 carbon atoms, R.sub.3, R.sub.4, R.sub.5 can be the same or
not the same.
2. The anthracene compound as claimed in claim 1, wherein X
represents the triarylsilyl group.
3. The anthracene compound as claimed in claim 1, wherein X
represents the triphenylsilyl group.
4. The anthracene compound as claimed in claim 1, wherein X
represents the trialkylsilyl group.
5. The anthracene compound as claimed in claim 4, wherein X
represents the trimethylsilyl group.
6. The anthracene compound as claimed in claim 1, wherein X
represents the benzyl group and it's derivatives or the anthryl
group and it's derivatives.
7. The anthracene compound as claimed in claim 1, wherein X
represents the furanyl group, the thiophenyl group, the pyrrolyl
group, the pyranyl group, the thiopyranyl group, the pyridinyl
group, the thiazolyl group, the imidazolyl group, the pyrimidinyl
group, or the triazinyl group.
8. The anthracene compound as claimed in claim 1, wherein R.sub.1
represents the fluorine, the chlorine, or the bromine.
9. The anthracene compound as claimed in claim 1, wherein R.sub.2
represents the fluorine, the chlorine or the bromine.
10. The anthracene compound as claimed in claim 1, wherein R.sub.3,
R.sub.4, and R.sub.5 represent the benzyl group or the methyl
group.
11. An organic light emitting diodes (OLED) material, at least
comprising anthracene compounds as claimed in claim 1.
12. An organic electroluminescent device, at least comprising: a
substrate; a first electrode layer, which is on said substrate; an
organic layer, which is on said first electrode, wherein at least
comprises an anthracene compound, represented by the following
formula: ##STR13## wherein X represents a substituted silyl group,
a substituted or unsubsituted aryl group having 6 to 20 carbon
atoms, a substituted or unsubsituted heteroaryl group having 2 to
20 carbon atoms, or a substituted or unsubsituted alkyl group
having 1 to 20 carbon atoms; each R.sub.1 and R.sub.2 represents
hydrogen, halogen, or a substituted or unsubsituted alkyl group
having 1 to 20 carbon atoms, R.sub.1 and R.sub.2 can be the same or
not the same; and each R.sub.3, R.sub.4 and R.sub.5 represents a
substituted or unsubsituted aryl group having 6 to 20 carbon atoms,
or a substituted or unsubsituted alkyl group having I to 12 carbon
atoms, R.sub.3, R.sub.4, R.sub.5 can be the same or not the same;
and a second electrode layer, which is on said organic layer.
13. The organic electroluminescent device as claimed in claim 12,
wherein said first electrode layer represents a transparent
conductive material.
14. The organic electroluminescent device as claimed in claim 12,
wherein said organic layer further comprises a hole injection
layer, a hole transport layer, and an electron transport layer.
15. The organic electroluminescent device as claimed in claim 14,
wherein said anthracene compound is comprised into said hole
transport layer.
16. The organic electroluminescent device as claimed in claim 12,
wherein X represents the tribenzylsilyl of the anthracene
compound.
17. The organic electroluminescent device as claimed in claim 12,
wherein X represents the benzyl group and it's derivatives or the
anthryl group and it's derivatives of the anthracene compound.
18. The organic electroluminescent device as claimed in claim 12,
wherein X represents the furanyl group, the thiophenyl group, the
pyrrolyl group, the pyranyl group, the thiopyranyl group, the
pyridinyl group, the thiazolyl group, the imidazolyl group, the
pyrimidinyl group or the triazinyl group of the anthracene
compound.
19. The organic electroluminescent device as claimed in claim 12,
wherein R.sub.1 represents the fluorine, the chlorine, or the
bromine in the anthracene compound.
20. The organic electroluminescent device as claimed in claim 12,
wherein R.sub.2 represents the fluorine, the chlorine, or the
bromine of the anthracene compound.
21. The organic electroluminescent device as claimed in claim 12,
wherein R.sub.3, R.sub.4, and R.sub.5 represent the benzyl group or
the methyl group of the anthracene compound.
Description
FIELD OF THE INVENTION
[0001] This invention relates to anthracene compound, particular on
the position 9 and 10, and at least one having a substituted silyl
group, the anthracene compound can be an organic light emitting
diode (OLED) material and used for organic electroluminescent
device.
BACKGROUND OF THE INVENTION
[0002] In recent years, the organic electriluminescent device
having high efficiency and fluorescent dyes, can be used for the
flat panel displays bring this technology commercialization. In
various types of flat panel displays, since an OLED, being
developed later than a liquid crystal display (LCD), has many
beneficial characteristics, such as a spontaneous light source, a
wide viewing angle, high response velocity, high brightness, strong
contrast, small thickness, power saving, and a wide operating
temperature, the OLED has been used extensively in small and medium
scale portable display fields.
[0003] The emitting layer is between the metal cathode and
transparent anode in the organic electriluminescent device. When a
DC voltage is applied to the OLED structure, electrons in the
cathode and holes in the transparent conductive layer will be
injected into the emitting layer through the electron transport
layer and the hole transport layer respectively. Due to the
potential difference incurred from the external electrical field,
electrons and holes will move in the emitting layer and recombine
as excitions. When the excitions come back to the ground state by
way of releasing energy, the quantum efficiency is released in a
form of photos to emit light downwards through the transparent
anode. This is the organic electroluminescent principle.
[0004] For example, in U.S. Pat. No. 6,465,115 disclosed anthracene
compound on the hole transport layer, which on position 9 and 10
having aryl group, the structure as following: ##STR2##
[0005] wherein substituents R.sup.1 to R.sup.4 are each
individually hydrogen, or alkyl of from 1 to 24 carbon atoms; aryl
or substituted aryl of from 5 to 20 carbon atoms; or heteroaryl or
substituted of from 5 to 24 carbon atoms; or fluorine, chlorine,
bromine; or cyano group.
[0006] In U.S. Pat. No. 5,759,444 also disclosed anthracene
compound, the structure as following: ##STR3##
[0007] Wherein each of A.sup.1 to A.sup.4 is a substituted or
unsubstituted aryl group having 6 to 16 carbon atoms, and each of
R.sup.1 to R .sup.8is a hydrogen atom independently, a halogen
atom, a substituted or unsubstituted alkoxy group, a substituted or
unsubstituted aryl group or a substituted or unsubstituted amino
group.
[0008] In U.S. Pat. 6,310,231 disclosed silane compounds as a
constituent material of luminescent device are described, which are
represented by following formula: ##STR4##
[0009] wherein R.sup.1 represents an alkyl group, an aryl group, a
heteroaryl group or an alkynyl group, and each of Ar.sup.11,
Ar.sup.12 and Ar.sup.13 represents a heteroaryl group.
[0010] Though the prior investigations described the organic light
emitting diode, it is very important to make new and efficient
organic EL materials to improve the spontaneous light source, a
wide viewing angle, high response velocity, high brightness, strong
contrast, small thickness, power saving, and a wide operating
temperature in the organic electriluminescent device.
SUMMARY OF THE INVENTION
[0011] This invention provides an organic light emitting diode
(OLED) material, which at least one having a substituted silyl
group on the position 9 and 10 of the anthracene compound, said the
anthracence compound represented by the following formula:
##STR5##
[0012] In the compound (A), X represents a substituted silyl group
(more preferably triphenylsilyl group), a trialkylsilyl group
having 1 to 20 carbon atoms (more preferably trimethylsilyl group,
triethylsilyl group, or tripropylsilyl group, particularly
preferably trimethylsilyl group), a substituted or unsubsituted
aryl group having 6 to 20 carbon atoms (more preferably benzyl
group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl
group, 4-ethylbenzyl group, biphenyl group, 4-methylbiphenyl group,
4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, triphenyl group,
naphthyl group, 5-methylnaphthyl group, anthryl group, or pyrenyl
group, particularly preferably benzyl group, naphthyl group,
biphenyl group, triphenyl group, or pyrenyl group etc.), a
substituted or unsubsituted heteroaryl group having 2 to 20 carbon
atoms (more preferably furanyl group, pyrrolyl group, pyridinyl
group, pyrimidinyl group, pyranyl group, thiophenyl group,
thiopyranyl, thiazolyl group, imidazolyl group, carbazole group,
triazinyl group, quinolinyl group, particularly preferably
pyridinyl group, carbazole group, or quinolinyl group), or a
substituted or unsubsituted alkyl group having 1 to 12 carbon atoms
(more preferably methyl, ethyl, propyl, or butyl).
[0013] In the compound (A), each R.sub.2 and R.sub.2 represents
hydrogen, halogen, or a substituted or unsubsituted alkyl group
having 1 to 20 carbon atoms (more preferably hydrogen, a
substituted or unsubsituted alkyl group having 1 to 4 carbon atoms,
fluorine, chlorine, or bromine, particularly preferably hydrogen,
methyl group, ethyl group, propyl group, butyl group, fluorine,
chlorine, or bromine), wherein R.sub.1 and R.sub.2 can be the same
or not the same.
[0014] In the compound (A), each R.sub.3, R.sub.4 and R.sub.5
represents a substituted or unsubsituted aryl group having 6 to 20
carbon atoms (more preferably benzyl group, 2-methylbenzyl group,
3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group,
biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group,
4-cyclohexylbiphenyl group, triphenyl group, naphthyl group,
5-methylnaphthyl group, anthryl group, or pyrenyl group,
particularly preferably benzyl group, naphthyl group, biphenyl
group, triphenyl group, or pyrenyl group etc.), or a substituted or
unsubsituted alkyl group having 1 to 12 carbon atoms (more
preferably a substituted or unsubsituted alkyl group having 1 to 4
carbon atoms, particularly preferably methyl group, ethyl group,
propyl group, or butyl group), wherein R.sub.1 and R.sub.2 can be
the same or not the same.
[0015] According to the above anthracene compound (A), there are
some compounds but not limited: ##STR6## ##STR7##
[0016] The invention also represents an organic electroluminescent
device, which comprising:
[0017] a substrate;
[0018] a first electrode layer, which is on the substrate;
[0019] an organic layer, which is on the first electrode, and the
organic layer including the anthracene compound (A) of mention
above; and
[0020] a second electrode layer, which is on the organic layer.
[0021] The substrate more preferably glass substrate, the first
electrode layer more preferably a transparent conductive material,
perfect preferably indium tin oxide film, the organic layer more
preferably including a hole injection layer, a hole transport
layer, a light emitting layer, a electron transport layer and a
electron injection layer, wherein the anthracene compound (A) is in
the light emitting layer; the second electrode layer more
preferably a metal layer, perfect preferably Aluminum in the
organic electroluminescent device.
[0022] Typical organic emitting materials were formed of a
conjugated organic host material and a conjugated organic
activating agent having condensed benzene rings. However, for the
production of full color OLED display panel, it is necessary to
have efficient red, green and blue (RGB) EL materials with proper
chromaticity and sufficient luminance efficiency. The guest-host
doped system offers a ready avenue fir achieving such an objective,
mainly because doping an emissive dopant of high luminescent
property into a host can raise the efficiency of radiative
recombination. In this application also having dopant in the
emissive layer, such as BDM. etc.
BRIEF DESCRIPTION OF THE DRAWINGS
[0023] FIG. 1 shows the PL intensity in different waves about
compound (1) and compound (2);
[0024] FIG. 2 shows the efficiency of organic light emitting diode
material in example 5 and compare example 1; and
[0025] FIG. 3(a) and FIG. 3(b) show the different of organic light
emitting diode material in the CIE chromaticity coordinates between
example 5 and compare example 1, wherein both the horizontal axis
represent voltage, the vertical axis represents CIEx in FIG. 3(a),
and the vertical axis represents CIEy in FIG. 3(b).
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Synthesis of anthracene compound
EXAMPLE 1
Sythesis of 9-bromo-10-triphenysilyl anthracene
[0026] In a nitrogen atmosphere, 12 g (35.7 mmol) of
9,10-dibromoanthracene, and 300 ml of tetrahydrofuran (THF) were
added to a round-bottom flask. Next, 14.4 ml (35.7 mmol, 2.5M) of
n-butyl lithium was added dropwise slowly into the round-bottom
flask at -78.degree. C. After mixing and reacting for 30 min, 12 g
(40.7 mmol) triphenylsilyl chloride with 50ml THF were added
dropwise slowly into the round-bottom flask at -78.degree. C. After
reacting at room temperature for 24 hours, the resulting mixture
was subjected to extraction with a mixed solvent (ethyl acetate:
H.sub.2O), dried over anhydrous MgSO.sub.4, filtered, and
condensed, then the crude product was purified by column
chromatography (n-hexane/acetyl acetate=15/1), A 9.0 g of pure
9-bromo-10-triphenysilyl anthracene was collected.
EXAMPLE 2
Sythesis of 9, 10-di-triphenysilyl anthracene (Compound 1)
[0027] In a nitrogen atmosphere, 9 g (17.5 mmol) of
9-bromo-10-triphenysily anthracene, and 200 ml of tetrahydrofuran
(THF) were added to a round-bottom flask. Next, 7.7 ml (19.3 mmol,
2.5M) of n-butyl lithium was added dropwise slowly into the
round-bottom flask at -78.degree. C. After mixing and reacting for
30 min, 6.2 g (21.2 mmol) triphenylsilyl chloride with 50 ml THF
added dropwise slowly into the round-bottom flask at -78.degree. C.
After reacting at room temperature for 24 hours, the resulting
mixture was subjected to extraction with a mixed solvent (ethyl
acetate:H.sub.2O), dried over anhydrous MgSO.sub.4, filtered, and
condensed, then the crude product was purified by column
chromatography (n-hexane/acetyl acetate=15/1), A 4.2 g of pure
9,10-di-triphenysilyl anthracene was collected, the reaction was
following: ##STR8##
EXAMPLE 3
Sythesis of 9-(2-naphthyl)-10-triphenysilyl anthracene (Compound
2)
[0028] 9-bromo-10-triphenysilyl anthracene (4 g, 7.8 mmol),
2-naphthylboronic acid (1.6 g, 9.4 mmol) and K.sub.2CO.sub.3 (1.5
g,15.6 mmmol) were dissolved in the solvent mixture of 50 mL
ethylene glycol dimethyl ether and 75 mL water. The stirred
solution was added tetrakis (triphenylphosphine) palladium (0) and
the mixture refuxed under N2 for 16 hours. The reaction mixture was
cooled and the water extracted with acetyl acetate three times. The
combined organic phase was washed with portions of brine. The
organic layer was then dried with MgSO.sub.4, filtered, and
evaporated of solvent. The crude material was purified by column
chromatography (n-hexane/acetyl acetate=10/1) to give
9-(2-naphthyl)-10-triphenysilyl anthracene (Compound 2), the
reaction was following: ##STR9## TABLE-US-00001 TABLE 1 Device
Characteristics of Examples CIE CIE Operation chromaticity
chromaticity emitting layer material Voltage Brightness coordinates
coordinates Efficiency Example Host Dopant (V) (cd/m.sup.2) (X
axis) (Y axis) (cd/A) Example 4*.sup.1 anthracene BDM*.sup.2 8.5
1000 0.15 0.13 2.1 compound (1) Example 5*.sup.1 ADN*.sup.3
anthracene 7.0 1000 0.20 0.23 1.7 compound (1) Example 6*.sup.1
anthracene BDM*.sup.2 8.5 1000 0.14 0.13 2.4 compound (2) Compare
ADN*.sup.3 BDM*.sup.2 7.1 1000 0.15 0.14 2.6 Example 1*.sup.1
*.sup.1The hole injection layer is consisted of 2T-NATA
(4,4',4''-tri(N-(2-naphthyl)-N-aniline)-triphenyl amine); the hole
transport layer is consisted of NPB
(N,N'-di-1-naphthyl-N,N'-diphenyl-1,1'-biphenyl-1,1'-biphenyl-4,4'-diamin-
e); the electron transport layer is consisted of Alq.sub.3 (tris
(8-hydroxyquinoline) aluminum). *.sup.2BDM: ##STR10## *.sup.3ADN:
##STR11##
[0029] From table 1, in the present invention, the host material of
emitting layer being the anthracene compound, as Example 4 and 6,
the CIE chromaticity coordinates (Y axis) from 0.14 to 0.13. So the
organic electroluminescent element approaches to blue light.
Furthermore, this invention also can be dopant, as Example 5.
[0030] Comparing the Example 5 with the Example 1, it is known the
efficiency and the color gamut of the present compound (Example 5)
better than the Example 1 from FIG. 2, FIG. 3(a) and FIG. 3(b).
[0031] Those skilled in the art will readily observe that numerous
modifications and alterations of the device and method may be made
while relating the teachings of the invention. Accordingly, the
above disclosure should be construed as limited only by the meters
and bounds of appended claims.
* * * * *