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US20070164669A1 - Silicon-contained anthracene compound for organic electroluminescent device - Google Patents

Silicon-contained anthracene compound for organic electroluminescent device Download PDF

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US20070164669A1
US20070164669A1 US11693288 US69328807A US2007164669A1 US 20070164669 A1 US20070164669 A1 US 20070164669A1 US 11693288 US11693288 US 11693288 US 69328807 A US69328807 A US 69328807A US 2007164669 A1 US2007164669 A1 US 2007164669A1
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anthracene
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Chen-Ping Yu
Chia-Liang Tai
Fan-Hsiu Chang
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AU Optronics Corp
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    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0062Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene aromatic compounds comprising a hetero atom, e.g.: N,P,S
    • H01L51/0071Polycyclic condensed heteroaromatic hydrocarbons
    • H01L51/0072Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ringsystem, e.g. phenanthroline, carbazole
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    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0079Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3)
    • H01L51/008Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3) comprising boron
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    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer

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.
Figure US20070164669A1-20070719-C00001

wherein X is an triarylsilyl group having 6 to 20 carbon atoms, an trialkylsilyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms. R1 and R2 is independently a hydrogen, halogen, or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms. R3 to R5 is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.

Description

    RELATED CASES
  • [0001]
    This application is a Divisional patent application of co-pending application Ser. No. 11/179,573, filed 13 Jul. 2005.
  • FIELD OF THE INVENTION
  • [0002]
    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
  • [0003]
    In recent years, the organic electroluminescent 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.
  • [0004]
    The emitting layer is between the metal cathode and transparent anode in the organic electroluminescent 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.
  • [0005]
    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:
    Figure US20070164669A1-20070719-C00002

    wherein substituents R1 to R4 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:
    Figure US20070164669A1-20070719-C00003

    Wherein each of A1 to A4 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, and each of R1 to R8 is 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.
  • [0007]
    In U.S. Pat. No. 6,310,231 disclosed silane compounds as a constituent material of luminescent device are described, which are represented by following formula:
    Figure US20070164669A1-20070719-C00004

    wherein R1 represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, and each of Ar11, Ar12 and Ar13 represents a heteroaryl group.
  • [0008]
    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 electroluminescent device.
  • SUMMARY OF THE INVENTION
  • [0009]
    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 anthracene compound represented by the following formula:
    Figure US20070164669A1-20070719-C00005
  • [0010]
    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 unsubstituted 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 unsubstituted 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 unsubstituted alkyl group having 1 to 12 carbon atoms (more preferably methyl, ethyl, propyl, or butyl).
  • [0011]
    In the compound (A), each R1 and R2 represents hydrogen, halogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (more preferably hydrogen, a substituted or unsubstituted 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 R1 and R2 can be the same or not the same.
  • [0012]
    In the compound (A), each R3, R4 and R5 represents a substituted or unsubstituted 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 unsubstituted alkyl group having 1 to 12 carbon atoms (more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, particularly preferably methyl group, ethyl group, propyl group, or butyl group), wherein R1 and R2 can be the same or not the same.
  • [0013]
    According to the above anthracene compound (A), there are some compounds but not limited:
    Figure US20070164669A1-20070719-C00006
    Figure US20070164669A1-20070719-C00007
    Figure US20070164669A1-20070719-C00008
  • [0014]
    The invention also represents an organic electroluminescent device, which comprising:
  • [0015]
    a substrate;
  • [0016]
    a first electrode layer, which is on the substrate;
  • [0017]
    an organic layer, which is on the first electrode, and the organic layer including the anthracene compound (A) of mention above; and
  • [0018]
    a second electrode layer, which is on the organic layer.
  • [0019]
    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.
  • [0020]
    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
  • [0021]
    FIG. 1 shows the PL intensity in different waves about compound (1) and compound (2);
  • [0022]
    FIG. 2 shows the efficiency of organic light emitting diode material in example 5 and compare example 1; and
  • [0023]
    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
  • [0000]
    Synthesis of Anthracene Compound
  • EXAMPLE 1 Synthesis of 9-bromo-10-triphenysilyl anthracene
  • [0024]
    In a nitrogen atmosphere, 12 g (35.7mmol) 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° C. After mixing and reacting for 30 min, 12 g (40.7 mmol) triphenylsilyl chloride with 50 ml THF were added dropwise slowly into the round-bottom flask at −78° C. After reacting at room temperature for 24 hours, the resulting mixture was subjected to extraction with a mixed solvent (ethyl acetate: H2O), dried over anhydrous MgSO4, 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 Synthesis of 9,10-di-triphenysilyl anthracene (Compound 1)
  • [0025]
    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° 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° C. After reacting at room temperature for 24 hours, the resulting mixture was subjected to extraction with a mixed solvent (ethyl acetate:H2O), dried over anhydrous MgSO4, 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:
    Figure US20070164669A1-20070719-C00009
  • EXAMPLE 3 Synthesis of 9-(2-naphthyl)-10-triphenysilyl anthracene (Compound 2)
  • [0026]
    9-bromo-10-triphenysilyl anthracene (4 g, 7.8 mmol), 2-naphthylboronic acid (1.6 g, 9.4 mmol) and K2CO3 (1.5 g,15.6 mmol) 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 refluxed 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 MgSO4, 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:
    Figure US20070164669A1-20070719-C00010
    TABLE 1
    Device Characteristics of Examples
    CIE CIE
    Operation chromaticity chromaticity
    emitting layer material Voltage Brightness coordinates coordinates Efficiency
    Example Host Dopant (V) (cd/m2) (X axis) (Y axis) (cd/A)
    Example 4*1 anthracene BDM*2 8.5 1000 0.15 0.13 2.1
    compound (1)
    Example 5*1 ADN*3 anthracene 7.0 1000 0.20 0.23 1.7
    compound (1)
    Example 6*1 anthracene BDM*2 8.5 1000 0.14 0.13 2.4
    compound (2)
    Compare ADN*3 BDM*2 7.1 1000 0.15 0.14 2.6
    Example 1*1

    *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′-diamine); the electron transport layer is consisted of Alq3 (tris(8-hydroxyquinoline)aluminum).

    *2BDM:
    Figure US20070164669A1-20070719-C00011

    *3ADN:
    Figure US20070164669A1-20070719-C00012
  • [0027]
    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.
  • [0028]
    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).
  • [0029]
    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.

Claims (10)

  1. 1. An organic electroluminescent device, comprising:
    a substrate;
    a first electrode layer, on the substrate;
    an organic layer, on the first electrode, wherein the organic layer at least comprises an anthracene compound, represented by the following formula:
    Figure US20070164669A1-20070719-C00013
    wherein X represents a trialkyl substituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; each R1 and R2 represents hydrogen, halogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R1 and R2 can be the same or not the same; and each R3, R4 and R5 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, R3, R4, R5 can be the same or not the same; and
    a second electrode layer, on the organic layer.
  2. 2. The organic electroluminescent device as claimed in claim 1, wherein the first electrode layer is made of a transparent conductive material.
  3. 3. The organic electroluminescent device as claimed in claim 1, wherein the organic layer further comprises a hole injection layer, a hole transport layer, and an electron transport layer.
  4. 4. The organic electroluminescent device as claimed in claim 3, wherein said anthracene compound is comprised into said hole transport layer.
  5. 5. The organic electroluminescent device as claimed in claim 1, wherein X represents a trimethylsilyl group.
  6. 6. The organic electroluminescent device as claimed in claim 1, wherein X represents the phenyl group and it's derivatives or the anthryl group and it's derivatives.
  7. 7. The organic electroluminescent device 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. 8. The organic electroluminescent device as claimed in claim 1, wherein R1 represents the fluorine, the chlorine, or the bromine.
  9. 9. The organic electroluminescent device as claimed in claim 1, wherein R2 represents the fluorine, the chlorine, or the bromine.
  10. 10. The organic electroluminescent device as claimed in claim 1, wherein R3, R4, and R5 represent the phenyl group or the methyl.
US11693288 2005-04-08 2007-03-29 Silicon-contained anthracene compound for organic electroluminescent device Abandoned US20070164669A1 (en)

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TW94111260 2005-04-08
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US11179573 US20060226768A1 (en) 2005-04-08 2005-07-13 Silicon-contained anthracene compound for organic electroluminescent device
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090108735A1 (en) * 2007-10-26 2009-04-30 Begley William J Oled device with fluoranthene electron transport materials
US20090110957A1 (en) * 2007-10-26 2009-04-30 Begley William J Oled device with certain fluoranthene host
US20090108736A1 (en) * 2007-10-26 2009-04-30 Begley William J Phosphorescent oled device with certain fluoranthene host
US20100117520A1 (en) * 2008-11-12 2010-05-13 Begley William J Oled device with fluoranthene electron injection materials
US20100244677A1 (en) * 2009-03-31 2010-09-30 Begley William J Oled device containing a silyl-fluoranthene derivative
US8420229B2 (en) 2007-10-26 2013-04-16 Global OLED Technologies LLC OLED device with certain fluoranthene light-emitting dopants

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5420249B2 (en) * 2005-12-08 2014-02-19 メルク パテント ゲーエムベーハー New materials for organic electroluminescent devices
JP2007230951A (en) * 2006-03-02 2007-09-13 Canon Inc Silyl compound, luminescent material and organic electroluminescent element using the same
WO2007129702A1 (en) * 2006-05-09 2007-11-15 Idemitsu Kosan Co., Ltd. Silicon-containing compound and organic electroluminescent device utilizing the same
US20100133996A1 (en) * 2007-05-09 2010-06-03 Dongjin Semichem Co., Ltd Novel anthracene typed compound and the organic electroluminescence display device using the same
KR100857023B1 (en) * 2007-05-21 2008-09-05 (주)그라쎌 Organic electroluminescent compounds and organic light emitting diode using the same
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5635308A (en) * 1994-04-26 1997-06-03 Tdk Corporation Phenylanthracene derivative and organic EL element
US5972247A (en) * 1998-03-20 1999-10-26 Eastman Kodak Company Organic electroluminescent elements for stable blue electroluminescent devices
US6777111B1 (en) * 1999-08-04 2004-08-17 Kabushiki Kaisha Chuo Kenkyusho Electro luminescent element
US7129386B2 (en) * 2003-06-27 2006-10-31 Canon Kabushiki Kaisha Substituted anthryl derivative and electroluminescence device using the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5635308A (en) * 1994-04-26 1997-06-03 Tdk Corporation Phenylanthracene derivative and organic EL element
US5972247A (en) * 1998-03-20 1999-10-26 Eastman Kodak Company Organic electroluminescent elements for stable blue electroluminescent devices
US6777111B1 (en) * 1999-08-04 2004-08-17 Kabushiki Kaisha Chuo Kenkyusho Electro luminescent element
US7129386B2 (en) * 2003-06-27 2006-10-31 Canon Kabushiki Kaisha Substituted anthryl derivative and electroluminescence device using the same

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090108735A1 (en) * 2007-10-26 2009-04-30 Begley William J Oled device with fluoranthene electron transport materials
US20090110957A1 (en) * 2007-10-26 2009-04-30 Begley William J Oled device with certain fluoranthene host
US20090108736A1 (en) * 2007-10-26 2009-04-30 Begley William J Phosphorescent oled device with certain fluoranthene host
US8431242B2 (en) 2007-10-26 2013-04-30 Global Oled Technology, Llc. OLED device with certain fluoranthene host
US8076009B2 (en) 2007-10-26 2011-12-13 Global Oled Technology, Llc. OLED device with fluoranthene electron transport materials
US8129039B2 (en) 2007-10-26 2012-03-06 Global Oled Technology, Llc Phosphorescent OLED device with certain fluoranthene host
US8420229B2 (en) 2007-10-26 2013-04-16 Global OLED Technologies LLC OLED device with certain fluoranthene light-emitting dopants
US8088500B2 (en) 2008-11-12 2012-01-03 Global Oled Technology Llc OLED device with fluoranthene electron injection materials
US20100117520A1 (en) * 2008-11-12 2010-05-13 Begley William J Oled device with fluoranthene electron injection materials
US20100244677A1 (en) * 2009-03-31 2010-09-30 Begley William J Oled device containing a silyl-fluoranthene derivative

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US20060226768A1 (en) 2006-10-12 application
US7449593B2 (en) 2008-11-11 grant

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