JP2012506923A5 - - Google Patents
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- Publication number
- JP2012506923A5 JP2012506923A5 JP2011533415A JP2011533415A JP2012506923A5 JP 2012506923 A5 JP2012506923 A5 JP 2012506923A5 JP 2011533415 A JP2011533415 A JP 2011533415A JP 2011533415 A JP2011533415 A JP 2011533415A JP 2012506923 A5 JP2012506923 A5 JP 2012506923A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- moiety
- polymer
- arylamine
- aryl
- 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.)
- Granted
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- 229920000642 polymer Polymers 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000005264 aryl amine group Chemical group 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 57
- -1 sulfonate ester Chemical class 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001174 sulfone group Chemical group 0.000 claims description 27
- 239000002019 doping agent Substances 0.000 claims description 24
- 150000004982 aromatic amines Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 21
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 21
- 125000005104 aryl silyl group Chemical group 0.000 claims description 21
- 125000005265 dialkylamine group Chemical group 0.000 claims description 21
- 125000005266 diarylamine group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 21
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 21
- 125000004001 thioalkyl group Chemical group 0.000 claims description 21
- 125000005000 thioaryl group Chemical group 0.000 claims description 21
- QJBPBQKYCDQIQV-UHFFFAOYSA-N 4-n-benzo[a]anthracen-1-ylbenzene-1,4-diamine Chemical group C1=CC(N)=CC=C1NC1=CC=CC2=CC=C(C=C3C(C=CC=C3)=C3)C3=C12 QJBPBQKYCDQIQV-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000001475 halogen functional group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims description 19
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 19
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000008054 sulfonate salts Chemical class 0.000 claims description 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000003457 sulfones Chemical group 0.000 claims description 3
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-UHFFFAOYSA-N 0.000 claims description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 2
- 238000012643 polycondensation polymerization Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 claims description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10885108P | 2008-10-27 | 2008-10-27 | |
| US61/108,851 | 2008-10-27 | ||
| PCT/US2009/062105 WO2010051259A1 (en) | 2008-10-27 | 2009-10-26 | Polyarylamine ketones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012506923A JP2012506923A (ja) | 2012-03-22 |
| JP2012506923A5 true JP2012506923A5 (enExample) | 2012-12-13 |
| JP5658161B2 JP5658161B2 (ja) | 2015-01-21 |
Family
ID=41404518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011533415A Active JP5658161B2 (ja) | 2008-10-27 | 2009-10-26 | ポリアリールアミンケトン |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8828274B2 (enExample) |
| EP (1) | EP2350166B1 (enExample) |
| JP (1) | JP5658161B2 (enExample) |
| KR (1) | KR101653801B1 (enExample) |
| WO (1) | WO2010051259A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8097876B2 (en) | 2008-10-27 | 2012-01-17 | Plextronics, Inc. | Charge injection and transport layers |
| US20100147386A1 (en) * | 2008-11-21 | 2010-06-17 | Plextronics, Inc. | Doped interfacial modification layers for stability enhancement for bulk heterojunction organic solar cells |
| KR101797783B1 (ko) * | 2009-09-29 | 2017-11-14 | 솔베이 유에스에이 인크. | 유기 전자 소자, 조성물 및 방법 |
| US8425808B2 (en) * | 2010-04-27 | 2013-04-23 | Xerox Corporation | Semiconducting composition |
| CN107236258A (zh) | 2010-05-11 | 2017-10-10 | 索尔维美国有限公司 | 掺杂的共轭聚合物和装置 |
| US9577194B2 (en) | 2010-07-02 | 2017-02-21 | Nissan Chemical Industries, Ltd. | Hole transport compositions and related devices and methods (I) |
| WO2012121417A1 (en) * | 2011-03-09 | 2012-09-13 | Waseda University | Conducting polymer / redox polymer blends via in-situ oxidative polymerization - preparation methods and application as an electro-active polymeric materials |
| EP2729532A1 (en) | 2011-07-05 | 2014-05-14 | Plextronics, Inc. | Vertically phase-separating semiconducting organic material layers |
| JP6269489B2 (ja) | 2011-10-04 | 2018-01-31 | 日産化学工業株式会社 | 正孔注入層および輸送層のための改善されたドーピング法 |
| WO2013156125A1 (de) * | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Vernetzbare sowie vernetzte polymere, verfahren zu deren herstellung sowie deren verwendung |
| US9112157B2 (en) | 2012-05-15 | 2015-08-18 | Solvay Usa, Inc. | Hole transport materials including OLED applications |
| WO2014039687A1 (en) | 2012-09-06 | 2014-03-13 | Plextronics, Inc. | Electroluminescent devices comprising insulator-free metal grids |
| EP3032621A1 (en) | 2014-12-10 | 2016-06-15 | VARTA Micro Innovation GmbH | Electrode for an electrochemical element with an organic electrolyte, electrochemical elements comprising the electrode and polymeric material and its use as electrode active material or as electrode binder |
| CN107406714B (zh) | 2014-12-15 | 2021-09-28 | 日产化学工业株式会社 | 含有空穴载体材料以及含氟聚合物的组合物及其用途 |
| WO2016140916A1 (en) | 2015-03-03 | 2016-09-09 | Solvay Usa, Inc. | Compositions containing hole carrier compounds and polymeric acids, and uses thereof |
| US10407581B2 (en) | 2015-04-22 | 2019-09-10 | Nissan Chemical Industries, Ltd. | Non-aqueous compositions having sulfonated polythiophenes suitable for use in organic electronics |
| CN107849376B (zh) | 2015-07-17 | 2021-11-30 | 日产化学工业株式会社 | 适用于有机电子的包含金属纳米颗粒的非水性油墨组合物 |
| WO2017126677A1 (en) | 2016-01-20 | 2017-07-27 | Nissan Chemical Industries, Ltd. | Non-aqueous ink compositions containing transition metal complexes, and uses thereof in organic electronics |
| KR102374183B1 (ko) * | 2016-06-17 | 2022-03-14 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
| CN110235264B (zh) | 2017-01-18 | 2022-08-23 | 日产化学株式会社 | 含有磺化共轭聚合物的墨液组合物 |
| KR102564836B1 (ko) | 2017-01-18 | 2023-08-09 | 닛산 가가쿠 가부시키가이샤 | 잉크 조성물 |
| KR102677529B1 (ko) | 2017-06-20 | 2024-06-24 | 닛산 가가쿠 가부시키가이샤 | 비수계 잉크 조성물 |
| KR102244800B1 (ko) | 2017-12-11 | 2021-04-26 | 주식회사 엘지화학 | 유기 발광 소자 및 이의 제조방법 |
| JP7447793B2 (ja) | 2018-09-25 | 2024-03-12 | 日産化学株式会社 | インク組成物 |
| JP2020127007A (ja) * | 2019-02-01 | 2020-08-20 | 株式会社リコー | 光電変換素子、太陽電池モジュール、電源モジュール、及び電子機器 |
| JP2021150647A (ja) * | 2020-03-17 | 2021-09-27 | 株式会社リコー | 光電変換素子、光電変換モジュール、電子機器、及び電源モジュール |
| WO2022212557A1 (en) * | 2021-03-31 | 2022-10-06 | Quadratic 3D, Inc. | Photohardenable compositions, methods, and a stabilizer |
| CN115594829B (zh) * | 2022-10-24 | 2025-02-18 | 吉林大学 | 一种具有电化学位点的聚芳砜/聚芳酮类电致变色聚合物薄膜及其制备方法和应用 |
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| JPH11251067A (ja) * | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
| AT410729B (de) | 2000-04-27 | 2003-07-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
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| KR20070102661A (ko) | 2004-09-24 | 2007-10-19 | 플렉스트로닉스, 인크 | 광기전 전지에서의 헤테로 원자를 갖는 위치 규칙적폴리(3-치환 티오펜) |
| KR101269256B1 (ko) | 2004-09-24 | 2013-05-29 | 플렉스트로닉스, 인크 | 헤테로 원자를 갖는 위치 규칙적 폴리(3-치환 티오펜)를 포함하는 전기발광 소자 |
| WO2006086480A2 (en) | 2005-02-10 | 2006-08-17 | Plextronics, Inc. | Hole injection/transport layer compositions and devices |
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| JP2006302636A (ja) * | 2005-04-20 | 2006-11-02 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置および照明装置 |
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| JP2009536656A (ja) | 2006-05-09 | 2009-10-15 | ユニバーシティ オブ ワシントン | 有機発光装置向けの架橋可能な正孔輸送物質 |
| KR101477703B1 (ko) | 2006-06-13 | 2015-01-02 | 솔베이 유에스에이 인크. | 풀러렌 및 그의 유도체를 포함하는 유기 광기전력 소자 |
| JP4985441B2 (ja) * | 2007-02-13 | 2012-07-25 | 三菱化学株式会社 | 高分子化合物、有機電界発光素子材料、有機電界発光素子用組成物および有機電界発光素子 |
| US8283002B2 (en) | 2008-11-18 | 2012-10-09 | Plextronics, Inc. | Aminobenzene compositions and related devices and methods |
-
2009
- 2009-10-26 US US12/606,162 patent/US8828274B2/en not_active Expired - Fee Related
- 2009-10-26 JP JP2011533415A patent/JP5658161B2/ja active Active
- 2009-10-26 WO PCT/US2009/062105 patent/WO2010051259A1/en not_active Ceased
- 2009-10-26 EP EP09752578.6A patent/EP2350166B1/en not_active Not-in-force
- 2009-10-26 KR KR1020117009489A patent/KR101653801B1/ko active Active
-
2014
- 2014-07-31 US US14/447,809 patent/US20140339532A1/en not_active Abandoned
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