TWI447143B - 電荷輸送性聚合物，有機電致發光元件用組成物，有機電致發光元件，有機ｅｌ顯示器及有機ｅｌ照明 - Google Patents
電荷輸送性聚合物，有機電致發光元件用組成物，有機電致發光元件，有機ｅｌ顯示器及有機ｅｌ照明 Download PDFInfo
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- TWI447143B TWI447143B TW098126902A TW98126902A TWI447143B TW I447143 B TWI447143 B TW I447143B TW 098126902 A TW098126902 A TW 098126902A TW 98126902 A TW98126902 A TW 98126902A TW I447143 B TWI447143 B TW I447143B
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- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 10
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 3
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- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical group N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical group S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 238000004857 zone melting Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2008207411 | 2008-08-11 |
Publications (2)
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| TW201012849A TW201012849A (en) | 2010-04-01 |
| TWI447143B true TWI447143B (zh) | 2014-08-01 |
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| TW098126902A TWI447143B (zh) | 2008-08-11 | 2009-08-11 | 電荷輸送性聚合物，有機電致發光元件用組成物，有機電致發光元件，有機ｅｌ顯示器及有機ｅｌ照明 |
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| US (1) | US8610112B2 (enExample) |
| EP (1) | EP2314639B1 (enExample) |
| JP (2) | JP5491796B2 (enExample) |
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| CN (1) | CN102105511B (enExample) |
| TW (1) | TWI447143B (enExample) |
| WO (1) | WO2010018813A1 (enExample) |
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| US8692234B2 (en) | 2008-04-02 | 2014-04-08 | Mitsubishi Chemical Corporation | Polymer compound, net-like polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescence element, organic electroluminescence element, organic EL display, and organic EL lighting |
| US9577194B2 (en) * | 2010-07-02 | 2017-02-21 | Nissan Chemical Industries, Ltd. | Hole transport compositions and related devices and methods (I) |
| GB2485001A (en) * | 2010-10-19 | 2012-05-02 | Cambridge Display Tech Ltd | OLEDs |
| JP5720191B2 (ja) * | 2010-11-12 | 2015-05-20 | 三菱化学株式会社 | アリールアミンポリマー、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明 |
| JP2012111719A (ja) * | 2010-11-25 | 2012-06-14 | Idemitsu Kosan Co Ltd | 重合性単量体、その重合体を含む有機デバイス用材料、正孔注入輸送材料及び有機エレクトロルミネッセンス素子用材料、並びに有機エレクトロルミネッセンス素子 |
| JP5573697B2 (ja) * | 2011-01-21 | 2014-08-20 | 三菱化学株式会社 | 重合体、有機電界発光素子材料、有機電界発光素子用組成物、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明 |
| WO2012104628A1 (en) * | 2011-01-31 | 2012-08-09 | Cambridge Display Technology Limited | Polymer |
| KR102029108B1 (ko) | 2011-05-13 | 2019-10-07 | 이데미쓰 고산 가부시키가이샤 | 유기 el 다색 발광 장치 |
| JP6031030B2 (ja) * | 2011-06-27 | 2016-11-24 | 新日鉄住金化学株式会社 | 有機電界発光素子用重合体及びそれを用いた有機電界発光素子 |
| KR20130024040A (ko) * | 2011-08-30 | 2013-03-08 | 삼성디스플레이 주식회사 | 광 발광 다이오드 및 이를 포함하는 광 발광 표시 장치 |
| WO2013035275A1 (ja) | 2011-09-09 | 2013-03-14 | 出光興産株式会社 | 含窒素へテロ芳香族環化合物 |
| US9991447B2 (en) | 2011-09-28 | 2018-06-05 | Idemitsu Korea Co., Ltd. | Material for organic electroluminescent element, and organic electroluminescent element produced using same |
| JPWO2013069242A1 (ja) | 2011-11-07 | 2015-04-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| CN104159947B (zh) | 2012-02-23 | 2016-10-05 | 三菱化学株式会社 | 聚合物和有机电致发光元件 |
| US9929347B2 (en) | 2012-03-27 | 2018-03-27 | Sumitomo Chemical Company, Limtied | Polymer compound and light emitting element using same |
| WO2013191137A1 (ja) | 2012-06-18 | 2013-12-27 | 三菱化学株式会社 | 高分子化合物、電荷輸送性ポリマー、有機電界発光素子用組成物、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明 |
| JP6015181B2 (ja) * | 2012-07-13 | 2016-10-26 | 日立化成株式会社 | 硬化性重合体並びにこれを用いた樹脂及び有機ｅｌ素子 |
| CN103833988B (zh) * | 2012-11-27 | 2016-08-03 | 海洋王照明科技股份有限公司 | 含蒽-噻咯并二(苯并噻二唑)共聚物及其制备方法和应用 |
| GB2509718A (en) * | 2013-01-09 | 2014-07-16 | Cambridge Display Tech Ltd | Method for forming a layer of an electronic device and appropriate precursor compounds |
| US10665786B2 (en) | 2013-03-08 | 2020-05-26 | Hitachi Chemical Company, Ltd. | Treatment liquid containing ionic compound, organic electronic element, and method for producing organic electronic element |
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| CN105683255B (zh) | 2013-10-04 | 2018-05-29 | 三菱化学株式会社 | 聚合物、有机电致发光元件用组合物、有机电致发光元件、有机el显示装置和有机el照明 |
| JP6500891B2 (ja) * | 2014-03-25 | 2019-04-17 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
| CN106133938B (zh) * | 2014-04-09 | 2018-06-19 | 住友化学株式会社 | 发光元件和用于该发光元件的组合物 |
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| CN106575718A (zh) | 2014-08-21 | 2017-04-19 | 陶氏环球技术有限责任公司 | 聚合电荷转移层和含有其的有机电子装置 |
| WO2016026122A1 (en) * | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Benzocyclobutenes derived compositions, and electronic devices containing the same |
| CN106715520B (zh) | 2014-09-25 | 2019-05-14 | 住友化学株式会社 | 高分子化合物和使用该高分子化合物的发光元件 |
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| KR102496777B1 (ko) * | 2015-02-25 | 2023-02-06 | 미쯔비시 케미컬 주식회사 | 중합체, 유기 전계 발광 소자용 조성물, 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 |
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| WO2010018813A1 (ja) | 2010-02-18 |
| EP2314639A4 (en) | 2013-08-07 |
| EP2314639A1 (en) | 2011-04-27 |
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| JP5491796B2 (ja) | 2014-05-14 |
| US8610112B2 (en) | 2013-12-17 |
| KR20110039444A (ko) | 2011-04-18 |
| US20110198573A1 (en) | 2011-08-18 |
| CN102105511B (zh) | 2013-01-02 |
| JP4935952B2 (ja) | 2012-05-23 |
| TW201012849A (en) | 2010-04-01 |
| CN102105511A (zh) | 2011-06-22 |
| JP2012015539A (ja) | 2012-01-19 |
| KR101619556B1 (ko) | 2016-05-10 |
| EP2314639B1 (en) | 2019-05-08 |
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