CN1919851B - 有机硅氧烷化合物和含有该化合物的有机发光装置 - Google Patents
有机硅氧烷化合物和含有该化合物的有机发光装置 Download PDFInfo
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- CN1919851B CN1919851B CN2006100932590A CN200610093259A CN1919851B CN 1919851 B CN1919851 B CN 1919851B CN 2006100932590 A CN2006100932590 A CN 2006100932590A CN 200610093259 A CN200610093259 A CN 200610093259A CN 1919851 B CN1919851 B CN 1919851B
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- AIPRAPZUGUTQKX-UHFFFAOYSA-N diethoxyphosphorylmethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1 AIPRAPZUGUTQKX-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- OANQELUUJGCUOQ-UHFFFAOYSA-N hexaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 OANQELUUJGCUOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- HTISDHGSRIQJEV-UHFFFAOYSA-N octacyclo[36.4.0.02,7.08,13.014,19.020,25.026,31.032,37]dotetraconta-1(42),2,4,6,8,10,12,14,16,18,20,22,24,26,28,30,32,34,36,38,40-henicosaene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 HTISDHGSRIQJEV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- MGQOSEADQRPWNX-UHFFFAOYSA-N triphenylen-1-ylphosphane Chemical compound C1=CC=CC2=C3C(P)=CC=CC3=C(C=CC=C3)C3=C21 MGQOSEADQRPWNX-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- 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]
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- 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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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
化合物号 | 最大吸收波长(nm) | 最小PL波长(nm) |
A | 368 | 423 |
B | 370 | 428 |
2 | 378 | 446 |
3 | 378 | 446 |
4 | 378 | 448 |
5 | 378 | 438 |
6 | 376 | 436 |
7 | 360,381,396 | 430 |
8 | 358,376,389 | 425 |
9 | 358,376,389 | 423 |
10 | 375 | 441 |
11 | 360,382,401 | 438 |
12 | 371 | 435 |
样品号 | 工作电压(V) | CIE色坐标(~100cd/m2) | 在7.2V的效率(cd/A) |
A | 4.7 | (0.16,0.09) | 0.65(在10V) |
B | 4.6 | (0.16,0.09) | 0.65(在8V) |
2 | 4.2 | (0.15,0.08) | 1.64(在7V) |
3 | 4.4 | (0.16,0.09) | 1.55(在8V) |
4 | 4.4 | (0.16,0.09) | 1.53(在8V) |
5 | 4.2 | (0.16,0.09) | 1.76(在7V) |
6 | 4.5 | (0.15,0.09) | 1.20(在8V) |
7 | 4.7 | (0.13,0.09) | 1.13(在9V) |
8 | 4.6 | (0.13,0.08) | 1.03(在9V) |
9 | 4.6 | (0.14,0.09) | 1.00(在10V) |
10 | 4.7 | (0.15,0.09) | 1.10(在10V) |
11 | 4.5 | (0.15,0.09) | 1.27(在10V) |
12 | 4.5 | (0.15,0.08) | 1.35(在10V) |
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR78720/05 | 2005-08-26 | ||
KR1020050078720A KR101193179B1 (ko) | 2005-08-26 | 2005-08-26 | 오가노실록산 화합물 및 이를 구비한 유기 발광 소자 |
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CN1919851A CN1919851A (zh) | 2007-02-28 |
CN1919851B true CN1919851B (zh) | 2012-11-28 |
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CN2006100932590A Active CN1919851B (zh) | 2005-08-26 | 2006-06-23 | 有机硅氧烷化合物和含有该化合物的有机发光装置 |
Country Status (4)
Country | Link |
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US (1) | US7887932B2 (zh) |
JP (1) | JP5449643B2 (zh) |
KR (1) | KR101193179B1 (zh) |
CN (1) | CN1919851B (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101193180B1 (ko) * | 2005-11-14 | 2012-10-19 | 삼성디스플레이 주식회사 | 전도성 고분자 조성물 및 이로부터 얻은 막을 구비한 전자소자 |
KR101243917B1 (ko) * | 2005-12-19 | 2013-03-14 | 삼성디스플레이 주식회사 | 전도성 고분자 조성물 및 이로부터 얻은 막을 구비한 전자소자 |
JP5105808B2 (ja) * | 2006-09-19 | 2012-12-26 | 保土谷化学工業株式会社 | ジスチリルベンゼン誘導体及びこれを用いた三次元メモリ材料、光制限材料、光造形用光硬化樹脂の硬化材料、並びに二光子蛍光顕微鏡用蛍光色素材料。 |
KR20080043199A (ko) * | 2006-11-13 | 2008-05-16 | 한국전자통신연구원 | 실리콘 나노점을 포함하는 발광층을 갖는 마이크로 크기의반도체 발광 소자, 이를 이용한 반도체 발광 소자 어레이,및 그 제조방법 |
JP5233185B2 (ja) * | 2007-07-04 | 2013-07-10 | 富士ゼロックス株式会社 | カルバゾール含有化合物 |
JP5130001B2 (ja) * | 2007-07-27 | 2013-01-30 | 富士フイルム株式会社 | 有機電界発光素子 |
KR101041145B1 (ko) * | 2008-07-09 | 2011-06-13 | 삼성모바일디스플레이주식회사 | 폴리실세스퀴옥산 공중합체, 그의 제조방법, 이를 이용하는폴리실세스퀴옥산 공중합체 박막, 및 이를 이용하는유기전계발광표시장치 |
JP5407841B2 (ja) * | 2009-12-24 | 2014-02-05 | 信越化学工業株式会社 | 反応性シリル基を有するトリアリールアミン誘導体及び無機材料並びに色素増感型光電変換素子 |
FI123292B (fi) * | 2011-06-14 | 2013-01-31 | Silecs Oy | Silaanimonomeerit ja niistä saatavat korkean taitekertoimen omaavat polymeerit |
JP5894945B2 (ja) | 2013-02-18 | 2016-03-30 | 信越化学工業株式会社 | 蛍光性化合物、その製造方法、及び蛍光性樹脂組成物 |
KR102263350B1 (ko) * | 2013-08-14 | 2021-06-11 | 듀폰 도레이 스페셜티 머티리얼즈 가부시키가이샤 | 신규한 오가노폴리실록산, 이를 포함하는 표면 처리제, 이를 포함하는 수지 조성물, 및 이의 겔상물 또는 경화물 |
JP2015071781A (ja) * | 2014-11-25 | 2015-04-16 | 株式会社東芝 | 希土類金属を含む蛍光体とそれを含む発光性組成物、およびその製造法、ならびに蛍光体を含む発光素子 |
JP7158100B2 (ja) * | 2016-09-30 | 2022-10-21 | 日産化学株式会社 | 架橋性オルガノポリシロキサン組成物、その硬化物及びled装置 |
CN109524244B (zh) * | 2017-09-19 | 2020-07-28 | 国家纳米科学中心 | 一种含氮二维共轭碳材料及其制备方法与应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5645948A (en) * | 1996-08-20 | 1997-07-08 | Eastman Kodak Company | Blue organic electroluminescent devices |
US6201051B1 (en) * | 1996-12-04 | 2001-03-13 | Bayer Aktiengesellschaft | Conducting organic-inorganic hybrid materials |
US6307083B1 (en) * | 1999-04-07 | 2001-10-23 | Fuji Photo Film Co., Ltd. | Specific silane compounds, method of synthesizing them, luminescent device materials comprising them, and luminescent devices containing such materials |
US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
US4672265A (en) | 1984-07-31 | 1987-06-09 | Canon Kabushiki Kaisha | Electroluminescent device |
US5635563A (en) | 1991-04-01 | 1997-06-03 | Tomoegawa Paper Co., Ltd. | Polyaniline derivatives and their production process |
WO1995001871A1 (en) | 1993-07-09 | 1995-01-19 | The Regents Of The University Of California | Electroluminescent diodes utilizing blends of polymers |
DE69608446T3 (de) | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2,7-aryl-9-substituierte fluorene und 9-substituierte fluorenoligomere und polymere |
US5928566A (en) | 1995-11-29 | 1999-07-27 | International Business Machines Corporation | Plasticized, antiplasticized and crystalline conducting polymers |
US5834100A (en) | 1996-06-25 | 1998-11-10 | Northwestern University | Organic light-emitting dioddes and methods for assembly and emission control |
US5728801A (en) | 1996-08-13 | 1998-03-17 | The Dow Chemical Company | Poly (arylamines) and films thereof |
US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
JP3518255B2 (ja) * | 1997-06-12 | 2004-04-12 | 凸版印刷株式会社 | 有機薄膜el素子 |
TW558561B (en) * | 1997-07-22 | 2003-10-21 | Sumitomo Chemical Co | Hole transporting polymer and organic electroluminescence device using the same |
JPH11329734A (ja) | 1998-03-10 | 1999-11-30 | Mitsubishi Chemical Corp | 有機電界発光素子 |
GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
JP3890796B2 (ja) | 1999-01-25 | 2007-03-07 | 住友化学株式会社 | 高分子発光素子 |
US6214937B1 (en) | 1999-03-26 | 2001-04-10 | The University Of Akron | Star-block polymers having multiple polyisobutylene-containing diblock copolymer arms radiating from a siloxane core and method for the synthesis thereof |
NO314525B1 (no) | 1999-04-22 | 2003-03-31 | Thin Film Electronics Asa | Fremgangsmåte ved fremstillingen av organiske halvledende innretninger i tynnfilm |
US6281285B1 (en) | 1999-06-09 | 2001-08-28 | Dow Corning Corporation | Silicone resins and process for synthesis |
JP2001196174A (ja) * | 2000-01-07 | 2001-07-19 | Tdk Corp | 有機el表示装置 |
US20010043043A1 (en) * | 2000-01-07 | 2001-11-22 | Megumi Aoyama | Organic electroluminescent display panel and organic electroluminescent device used therefor |
US6517958B1 (en) | 2000-07-14 | 2003-02-11 | Canon Kabushiki Kaisha | Organic-inorganic hybrid light emitting devices (HLED) |
US6927301B2 (en) | 2000-10-27 | 2005-08-09 | The Regents Of The University Of Michigan | Well-defined nanosized building blocks for organic/inorganic nanocomposites |
US6558575B2 (en) | 2001-02-07 | 2003-05-06 | Agfa-Gevaert | Perparation of improved ZnS:Mn phosphors |
US6623711B2 (en) | 2001-03-27 | 2003-09-23 | Samsung Electronics Co., Ltd. | Siloxane-based resin and method for forming insulating film between interconnect layers in semiconductor devices by using the same |
CA2381833C (en) | 2002-04-16 | 2011-02-15 | American Dye Source, Inc. | Hybrid organic-inorganic light emitting polymers |
US6830830B2 (en) | 2002-04-18 | 2004-12-14 | Canon Kabushiki Kaisha | Semiconducting hole injection materials for organic light emitting devices |
KR100552683B1 (ko) | 2002-06-21 | 2006-02-20 | 삼성에스디아이 주식회사 | 청색 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
KR100695106B1 (ko) | 2002-12-24 | 2007-03-14 | 삼성에스디아이 주식회사 | 청색 발광 고분자 및 이를 채용한 유기 전계 발광 소자 |
JP4325197B2 (ja) | 2003-01-15 | 2009-09-02 | 三菱化学株式会社 | 有機電界発光素子 |
KR100522687B1 (ko) | 2003-02-04 | 2005-10-20 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
US20040209116A1 (en) | 2003-04-21 | 2004-10-21 | Xiaofan Ren | Organic light emitting devices with wide gap host materials |
US6999222B2 (en) | 2003-08-13 | 2006-02-14 | The Regents Of The University Of California | Plasmon assisted enhancement of organic optoelectronic devices |
KR100773522B1 (ko) | 2003-10-02 | 2007-11-07 | 삼성에스디아이 주식회사 | 사이클로펜타페난트렌계 화합물 및 이를 이용한 유기 전계발광 소자 |
US20050123760A1 (en) | 2003-10-15 | 2005-06-09 | Cammack J. K. | Light-emitting nanoparticle compositions |
KR100718103B1 (ko) | 2003-12-09 | 2007-05-14 | 삼성에스디아이 주식회사 | 발광 고분자 및 이를 이용한 유기 전계 발광 소자 |
KR100773524B1 (ko) | 2003-12-24 | 2007-11-07 | 삼성에스디아이 주식회사 | 이핵 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 |
KR100682860B1 (ko) | 2004-01-27 | 2007-02-15 | 삼성에스디아이 주식회사 | 스피로플루오렌계 고분자 및 이를 이용한 유기 전계 발광소자 |
US7294961B2 (en) | 2004-03-29 | 2007-11-13 | Articulated Technologies, Llc | Photo-radiation source provided with emissive particles dispersed in a charge-transport matrix |
JP2006108458A (ja) | 2004-10-07 | 2006-04-20 | Canon Inc | 発光素子及び表示装置 |
KR101156426B1 (ko) | 2005-08-25 | 2012-06-18 | 삼성모바일디스플레이주식회사 | 실세스퀴옥산계 화합물 및 이를 구비한 유기 발광 소자 |
KR101193180B1 (ko) | 2005-11-14 | 2012-10-19 | 삼성디스플레이 주식회사 | 전도성 고분자 조성물 및 이로부터 얻은 막을 구비한 전자소자 |
KR101243917B1 (ko) | 2005-12-19 | 2013-03-14 | 삼성디스플레이 주식회사 | 전도성 고분자 조성물 및 이로부터 얻은 막을 구비한 전자소자 |
-
2005
- 2005-08-26 KR KR1020050078720A patent/KR101193179B1/ko active IP Right Grant
-
2006
- 2006-06-07 US US11/448,142 patent/US7887932B2/en not_active Expired - Fee Related
- 2006-06-23 CN CN2006100932590A patent/CN1919851B/zh active Active
- 2006-08-28 JP JP2006230835A patent/JP5449643B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5645948A (en) * | 1996-08-20 | 1997-07-08 | Eastman Kodak Company | Blue organic electroluminescent devices |
US6201051B1 (en) * | 1996-12-04 | 2001-03-13 | Bayer Aktiengesellschaft | Conducting organic-inorganic hybrid materials |
US6307083B1 (en) * | 1999-04-07 | 2001-10-23 | Fuji Photo Film Co., Ltd. | Specific silane compounds, method of synthesizing them, luminescent device materials comprising them, and luminescent devices containing such materials |
US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
Non-Patent Citations (2)
Title |
---|
Thomas Müller, et al..1,3-dimethyl-1,3-bis(2,3,4-triphenyl-1-naphthyl)disilxane hexane solvate..《Acta. Cryst.》.2003,第E59卷o1838-o1839. * |
ThomasMüller et al..1 |
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Publication number | Publication date |
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JP5449643B2 (ja) | 2014-03-19 |
CN1919851A (zh) | 2007-02-28 |
KR101193179B1 (ko) | 2012-10-19 |
JP2007063273A (ja) | 2007-03-15 |
US20070048532A1 (en) | 2007-03-01 |
KR20070024121A (ko) | 2007-03-02 |
US7887932B2 (en) | 2011-02-15 |
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