JP2007525498A5 - - Google Patents
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- Publication number
- JP2007525498A5 JP2007525498A5 JP2006554290A JP2006554290A JP2007525498A5 JP 2007525498 A5 JP2007525498 A5 JP 2007525498A5 JP 2006554290 A JP2006554290 A JP 2006554290A JP 2006554290 A JP2006554290 A JP 2006554290A JP 2007525498 A5 JP2007525498 A5 JP 2007525498A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- fluoroaryl
- fluoroalkyl
- alkyl
- integer
- 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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- 125000003118 aryl group Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 44
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 20
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 0 *N(*)c1ccccc1 Chemical compound *N(*)c1ccccc1 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- NHPPIJMARIVBGU-UHFFFAOYSA-N 1-iodonaphthalene Chemical compound C1=CC=C2C(I)=CC=CC2=C1 NHPPIJMARIVBGU-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/782,357 US7960587B2 (en) | 2004-02-19 | 2004-02-19 | Compositions comprising novel compounds and electronic devices made with such compositions |
| US10/782,357 | 2004-02-19 | ||
| PCT/US2005/005579 WO2005080525A2 (en) | 2004-02-19 | 2005-02-17 | Aromatic amine compositions and electronic devices made with such compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011074540A Division JP2011173893A (ja) | 2004-02-19 | 2011-03-30 | 新規な化合物を含む組成物、およびそのような組成物で製造された電子デバイス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007525498A JP2007525498A (ja) | 2007-09-06 |
| JP2007525498A5 true JP2007525498A5 (https=) | 2008-04-10 |
| JP4820762B2 JP4820762B2 (ja) | 2011-11-24 |
Family
ID=34861013
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554290A Expired - Fee Related JP4820762B2 (ja) | 2004-02-19 | 2005-02-17 | 新規トリアリールアミン化合物およびその製造方法 |
| JP2011074540A Pending JP2011173893A (ja) | 2004-02-19 | 2011-03-30 | 新規な化合物を含む組成物、およびそのような組成物で製造された電子デバイス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011074540A Pending JP2011173893A (ja) | 2004-02-19 | 2011-03-30 | 新規な化合物を含む組成物、およびそのような組成物で製造された電子デバイス |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7960587B2 (https=) |
| EP (1) | EP1725629B1 (https=) |
| JP (2) | JP4820762B2 (https=) |
| KR (1) | KR101197802B1 (https=) |
| TW (1) | TWI370165B (https=) |
| WO (1) | WO2005080525A2 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004029128A2 (en) | 2002-09-24 | 2004-04-08 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| CA2499364A1 (en) | 2002-09-24 | 2004-04-08 | E. I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| US7317047B2 (en) | 2002-09-24 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
| JP4464277B2 (ja) | 2002-09-24 | 2010-05-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法 |
| US7390438B2 (en) | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
| US7365230B2 (en) | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| JP5214237B2 (ja) * | 2004-03-31 | 2013-06-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電荷輸送材料として使用するトリアリールアミン化合物 |
| US8147962B2 (en) | 2004-04-13 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Conductive polymer composites |
| EP1897096A4 (en) | 2005-06-28 | 2009-08-12 | Du Pont | TRANSPARENT LADDER WITH HIGH WORKING FUNCTION |
| WO2007002740A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
| US8440324B2 (en) | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
| US7838627B2 (en) * | 2005-12-29 | 2010-11-23 | E. I. Du Pont De Nemours And Company | Compositions comprising novel compounds and polymers, and electronic devices made with such compositions |
| US8216680B2 (en) | 2006-02-03 | 2012-07-10 | E I Du Pont De Nemours And Company | Transparent composite conductors having high work function |
| US20080047930A1 (en) | 2006-08-23 | 2008-02-28 | Graciela Beatriz Blanchet | Method to form a pattern of functional material on a substrate |
| US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
| US7821637B1 (en) | 2007-02-22 | 2010-10-26 | J.A. Woollam Co., Inc. | System for controlling intensity of a beam of electromagnetic radiation and method for investigating materials with low specular reflectance and/or are depolarizing |
| US20080251768A1 (en) | 2007-04-13 | 2008-10-16 | Che-Hsiung Hsu | Electrically conductive polymer compositions |
| US8241526B2 (en) | 2007-05-18 | 2012-08-14 | E I Du Pont De Nemours And Company | Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives |
| JP2009164113A (ja) * | 2007-12-12 | 2009-07-23 | Mitsubishi Chemicals Corp | 有機電界発光素子の製造方法及び有機ｅｌディスプレイ |
| WO2010051259A1 (en) * | 2008-10-27 | 2010-05-06 | Plextronics, Inc. | Polyarylamine ketones |
| US8283002B2 (en) * | 2008-11-18 | 2012-10-09 | Plextronics, Inc. | Aminobenzene compositions and related devices and methods |
| US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| KR101561402B1 (ko) | 2009-03-12 | 2015-10-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 코팅 도포를 위한 전기 전도성 중합체 조성물 |
| EP2414481A4 (en) * | 2009-04-03 | 2013-02-20 | Du Pont | ELECTROACTIVE MATERIALS |
| EP2421918B1 (en) | 2009-04-21 | 2020-08-26 | LG Chem, Ltd. | Electrically conductive polymer compositions and films made therefrom |
| TW201100482A (en) | 2009-04-24 | 2011-01-01 | Du Pont | Electrically conductive polymer compositions and films made therefrom |
| US8592239B2 (en) * | 2009-07-27 | 2013-11-26 | E I Du Pont De Nemours And Company | Process and materials for making contained layers and devices made with same |
| KR101790854B1 (ko) | 2009-09-29 | 2017-10-26 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 발광 응용을 위한 중수소화된 화합물 |
| JP2013508375A (ja) | 2009-10-19 | 2013-03-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電子用途用のトリアリールアミン化合物 |
| CN102574773B (zh) | 2009-10-19 | 2014-09-17 | E.I.内穆尔杜邦公司 | 用于电子应用的三芳基胺化合物 |
| US20110101312A1 (en) | 2009-10-29 | 2011-05-05 | E. I. Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
| GB2484253B (en) | 2010-05-14 | 2013-09-11 | Cambridge Display Tech Ltd | Organic light-emitting composition and device |
| JP5727038B2 (ja) | 2010-12-20 | 2015-06-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 電子技術応用のための組成物 |
| JP5966715B2 (ja) * | 2012-07-20 | 2016-08-10 | 東ソー株式会社 | 新規なアリールアミンポリマー、その製造方法及びその用途 |
| US9972783B2 (en) | 2015-03-25 | 2018-05-15 | E I Du Pont De Nemours And Company | High energy triarylamine compounds for hole transport materials |
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| JP5214237B2 (ja) * | 2004-03-31 | 2013-06-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電荷輸送材料として使用するトリアリールアミン化合物 |
-
2004
- 2004-02-19 US US10/782,357 patent/US7960587B2/en active Active
-
2005
- 2005-02-17 JP JP2006554290A patent/JP4820762B2/ja not_active Expired - Fee Related
- 2005-02-17 KR KR1020067019117A patent/KR101197802B1/ko not_active Expired - Fee Related
- 2005-02-17 TW TW094104570A patent/TWI370165B/zh not_active IP Right Cessation
- 2005-02-17 EP EP05713928A patent/EP1725629B1/en not_active Expired - Lifetime
- 2005-02-17 WO PCT/US2005/005579 patent/WO2005080525A2/en not_active Ceased
-
2011
- 2011-03-30 JP JP2011074540A patent/JP2011173893A/ja active Pending
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