JP2004532314A5 - - Google Patents
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- JP2004532314A5 JP2004532314A5 JP2002582109A JP2002582109A JP2004532314A5 JP 2004532314 A5 JP2004532314 A5 JP 2004532314A5 JP 2002582109 A JP2002582109 A JP 2002582109A JP 2002582109 A JP2002582109 A JP 2002582109A JP 2004532314 A5 JP2004532314 A5 JP 2004532314A5
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- JP
- Japan
- Prior art keywords
- polymer
- group
- repeating unit
- charge injection
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 claims description 116
- 239000000178 monomer Substances 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 230000003287 optical effect Effects 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 5
- 230000003381 solubilizing effect Effects 0.000 claims description 5
- 125000005620 boronic acid group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical group C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- -1 8-hydroxyquinoline (aluminum) Chemical compound 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OAKYWZLTBSQZDB-UHFFFAOYSA-N 1,3,5-triphenyl-2,4-dihydrotriazine Chemical group C1N(C=2C=CC=CC=2)NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 OAKYWZLTBSQZDB-UHFFFAOYSA-N 0.000 description 1
- JLDLWTAGIXTWCH-UHFFFAOYSA-N 2-[4-(2-aminophenyl)-6-phenyl-1,3,5-triazin-2-yl]aniline Chemical class NC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC=CC=2)N)=N1 JLDLWTAGIXTWCH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0109108.1A GB0109108D0 (en) | 2001-04-11 | 2001-04-11 | Polymer, its preparation and uses |
| PCT/GB2002/001585 WO2002083760A2 (en) | 2001-04-11 | 2002-04-10 | Conjugated homo-and copolymers comprising substituted or unsubstituted heteroaryl group, its preparation and uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010167160A Division JP5197687B2 (ja) | 2001-04-11 | 2010-07-26 | ポリマー及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004532314A JP2004532314A (ja) | 2004-10-21 |
| JP2004532314A5 true JP2004532314A5 (enExample) | 2010-09-09 |
Family
ID=9912704
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002582109A Pending JP2004532314A (ja) | 2001-04-11 | 2002-04-10 | ポリマー及びその製造方法 |
| JP2010167160A Expired - Fee Related JP5197687B2 (ja) | 2001-04-11 | 2010-07-26 | ポリマー及びその製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010167160A Expired - Fee Related JP5197687B2 (ja) | 2001-04-11 | 2010-07-26 | ポリマー及びその製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7985815B2 (enExample) |
| EP (2) | EP1377627B1 (enExample) |
| JP (2) | JP2004532314A (enExample) |
| AT (2) | ATE544185T1 (enExample) |
| AU (1) | AU2002242900A1 (enExample) |
| DE (1) | DE60234756D1 (enExample) |
| GB (1) | GB0109108D0 (enExample) |
| WO (1) | WO2002083760A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0109108D0 (en) * | 2001-04-11 | 2001-05-30 | Cambridge Display Tech Ltd | Polymer, its preparation and uses |
| DE112006000495B4 (de) * | 2005-03-01 | 2017-11-09 | The Regents Of The University Of California | Mehrschichtige Licht emittierende Polymer-Diode für Festkörper Beleuchtungs-Anwendungen |
| CN102321234A (zh) * | 2005-05-24 | 2012-01-18 | 日立化成工业株式会社 | 共轭聚合物的制造方法 |
| GB0617167D0 (en) | 2006-08-31 | 2006-10-11 | Cdt Oxford Ltd | Compounds for use in opto-electrical devices |
| JP5604804B2 (ja) * | 2008-04-25 | 2014-10-15 | 住友化学株式会社 | 含窒素複素環式化合物を含む組成物 |
| EP2275469A4 (en) | 2008-04-25 | 2012-11-28 | Sumitomo Chemical Co | POLYMER CONNECTION WITH A REST OF NITROGENOUS HETEROCYCLIC COMPOUND |
| JP5691177B2 (ja) * | 2009-01-29 | 2015-04-01 | 住友化学株式会社 | 高分子化合物及びそれを用いる発光素子 |
| JP5340999B2 (ja) * | 2010-03-04 | 2013-11-13 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP4832605B2 (ja) * | 2010-04-20 | 2011-12-07 | 住友化学株式会社 | 有機発光素子 |
| KR101778825B1 (ko) | 2010-05-03 | 2017-09-14 | 메르크 파텐트 게엠베하 | 제형물 및 전자 소자 |
| CN102869672B (zh) * | 2010-05-03 | 2016-05-11 | 默克专利有限公司 | 制剂和电子器件 |
| US20130270486A1 (en) * | 2010-12-21 | 2013-10-17 | Sumitomo Chemical Company, Limited | Polymer compound and light-emitting device using same |
| CN103270078B (zh) * | 2010-12-21 | 2015-12-16 | 住友化学株式会社 | 高分子化合物及使用其的发光元件 |
| GB2505893A (en) | 2012-09-13 | 2014-03-19 | Cambridge Display Tech Ltd | Compounds for use in organic optoelectronic devices |
| GB201223283D0 (en) | 2012-12-21 | 2013-02-06 | Cambridge Display Tech Ltd | Polymer and organic electronic device |
| JP6769020B2 (ja) * | 2015-09-30 | 2020-10-14 | 日立化成株式会社 | 電荷輸送性材料、該材料を用いたインク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4487920A (en) | 1983-06-13 | 1984-12-11 | Allied Corporation | Polyamide-polyol-triazine block copolymer and anionic polymerization process |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| JP3069139B2 (ja) * | 1990-03-16 | 2000-07-24 | 旭化成工業株式会社 | 分散型電界発光素子 |
| GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
| JPH04354736A (ja) | 1991-05-31 | 1992-12-09 | Omron Corp | 紙葉類の定圧繰出し装置 |
| JP2675228B2 (ja) | 1992-02-20 | 1997-11-12 | シャープ株式会社 | 紙押え装置 |
| JPH07224162A (ja) | 1994-02-14 | 1995-08-22 | Hoechst Japan Ltd | トリアジンポリマー |
| ATE228545T1 (de) | 1994-05-06 | 2002-12-15 | Bayer Ag | Leitfähige beschichtungen |
| US6255483B1 (en) * | 1995-03-15 | 2001-07-03 | Ciba Specialty Chemicals Corporation | Biphenyl-substituted triazines |
| JP3080359B2 (ja) * | 1996-05-09 | 2000-08-28 | 工業技術院長 | 多分岐重合体およびその製造方法 |
| DE19628719B4 (de) * | 1996-07-17 | 2006-10-05 | Hans-Werner Prof. Dr. Schmidt | Elektronenleitende Schicht in organischen, elektrolumineszierenden Anordnungen |
| ES2168144T3 (es) * | 1996-09-16 | 2002-06-01 | Bayer Ag | Polimeros de triazina y su empleo en disposiciones electroluminiscentes. |
| US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| GB9726810D0 (en) | 1997-12-19 | 1998-02-18 | Zeneca Ltd | Compounds composition & use |
| KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
| GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
| WO2000046321A1 (en) | 1999-02-04 | 2000-08-10 | The Dow Chemical Company | Fluorene copolymers and devices made therefrom |
| JP3310658B1 (ja) | 1999-03-05 | 2002-08-05 | ケンブリッジ ディスプレイ テクノロジー リミテッド | 高分子の合成方法 |
| JP2001151868A (ja) * | 1999-11-24 | 2001-06-05 | Toyota Central Res & Dev Lab Inc | 機能性共重合高分子及びそれを使用した有機電界発光素子、光メモリ、正孔移動素子 |
| US6512082B2 (en) * | 2000-01-05 | 2003-01-28 | Cambridge Display Technology Ltd. | Polymers, their preparation and uses |
| US6821643B1 (en) * | 2000-01-21 | 2004-11-23 | Xerox Corporation | Electroluminescent (EL) devices |
| GB0109108D0 (en) * | 2001-04-11 | 2001-05-30 | Cambridge Display Tech Ltd | Polymer, its preparation and uses |
| GB0125620D0 (en) * | 2001-10-25 | 2001-12-19 | Cambridge Display Tech Ltd | Monomers and low band gap polymers formed therefrom |
| US6730417B2 (en) * | 2002-01-29 | 2004-05-04 | Xerox Corporation | Organic electroluminescent (EL) devices |
| JP2005268022A (ja) | 2004-03-18 | 2005-09-29 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
-
2001
- 2001-04-11 GB GBGB0109108.1A patent/GB0109108D0/en not_active Ceased
-
2002
- 2002-04-10 AT AT09012920T patent/ATE544185T1/de active
- 2002-04-10 DE DE60234756T patent/DE60234756D1/de not_active Expired - Lifetime
- 2002-04-10 EP EP02708540A patent/EP1377627B1/en not_active Expired - Lifetime
- 2002-04-10 EP EP09012920A patent/EP2166582B1/en not_active Expired - Lifetime
- 2002-04-10 US US10/475,027 patent/US7985815B2/en not_active Expired - Fee Related
- 2002-04-10 AU AU2002242900A patent/AU2002242900A1/en not_active Abandoned
- 2002-04-10 JP JP2002582109A patent/JP2004532314A/ja active Pending
- 2002-04-10 WO PCT/GB2002/001585 patent/WO2002083760A2/en not_active Ceased
- 2002-04-10 AT AT02708540T patent/ATE452156T1/de not_active IP Right Cessation
-
2010
- 2010-07-26 JP JP2010167160A patent/JP5197687B2/ja not_active Expired - Fee Related
-
2011
- 2011-07-22 US US13/189,465 patent/US8933182B2/en not_active Expired - Fee Related
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