JP2018505162A5 - - Google Patents
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- Publication number
- JP2018505162A5 JP2018505162A5 JP2017537399A JP2017537399A JP2018505162A5 JP 2018505162 A5 JP2018505162 A5 JP 2018505162A5 JP 2017537399 A JP2017537399 A JP 2017537399A JP 2017537399 A JP2017537399 A JP 2017537399A JP 2018505162 A5 JP2018505162 A5 JP 2018505162A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- diphenyl
- phenyl
- naphthalen
- phenanthroline
- 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
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- -1 4-biphenylyl Chemical group 0.000 claims 5
- 239000002019 doping agent Substances 0.000 claims 5
- 239000000463 material Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000003949 imides Chemical class 0.000 claims 2
- WMZCREDANYEXRT-UHFFFAOYSA-N 1-[phenyl(pyren-1-yl)phosphoryl]pyrene Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1P(C=1C2=CC=C3C=CC=C4C=CC(C2=C43)=CC=1)(=O)C1=CC=CC=C1 WMZCREDANYEXRT-UHFFFAOYSA-N 0.000 claims 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 claims 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 claims 1
- GTPNJFWMUYHPEP-UHFFFAOYSA-N 2-(4-phenylphenyl)-5-[6-[6-[5-(4-phenylphenyl)-1,3,4-oxadiazol-2-yl]pyridin-2-yl]pyridin-2-yl]-1,3,4-oxadiazole Chemical group C1=CC=CC=C1C1=CC=C(C=2OC(=NN=2)C=2N=C(C=CC=2)C=2N=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GTPNJFWMUYHPEP-UHFFFAOYSA-N 0.000 claims 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 claims 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 claims 1
- CELPGKFEUDCZOU-UHFFFAOYSA-N 2-naphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 CELPGKFEUDCZOU-UHFFFAOYSA-N 0.000 claims 1
- YNTQHSDEZACXAP-UHFFFAOYSA-N 3,5-di(pyren-1-yl)pyridine Chemical compound c1cc2ccc3ccc(-c4cncc(c4)-c4ccc5ccc6cccc7ccc4c5c67)c4ccc(c1)c2c34 YNTQHSDEZACXAP-UHFFFAOYSA-N 0.000 claims 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 claims 1
- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 claims 1
- JOWLUTHJWQYFOH-UHFFFAOYSA-N 3-[3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]-5-(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical group C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 JOWLUTHJWQYFOH-UHFFFAOYSA-N 0.000 claims 1
- ACSHDTNTFKFOOH-UHFFFAOYSA-N 3-[4-[3,5-bis(4-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=CC(=CC=2)C=2C=C(C=C(C=2)C=2C=CC(=CC=2)C=2C=NC=CC=2)C=2C=CC(=CC=2)C=2C=NC=CC=2)=C1 ACSHDTNTFKFOOH-UHFFFAOYSA-N 0.000 claims 1
- BSVILDUORGWESI-UHFFFAOYSA-N 3-methyl-2-(4-naphthalen-2-ylphenyl)imidazo[4,5-f][1,10]phenanthroline Chemical compound C1=CC=CC2=CC(C3=CC=C(C=C3)C=3N(C4=C(C5=CC=CN=C5C5=NC=CC=C54)N=3)C)=CC=C21 BSVILDUORGWESI-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 claims 1
- RFVBBELSDAVRHM-UHFFFAOYSA-N 9,10-dinaphthalen-2-yl-2-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C(C=2C=C3C=CC=CC3=CC=2)=C2C(C=CC=C2)=C2C=3C=C4C=CC=CC4=CC=3)C2=C1 RFVBBELSDAVRHM-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- YVVVSJAMVJMZRF-UHFFFAOYSA-N c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 Chemical compound c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 YVVVSJAMVJMZRF-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- UIJLKECZHOSSHF-UHFFFAOYSA-N diphenyl-bis(4-pyridin-3-ylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=NC=CC=1)(C=1C=CC(=CC=1)C=1C=NC=CC=1)C1=CC=CC=C1 UIJLKECZHOSSHF-UHFFFAOYSA-N 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 claims 1
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000003967 siloles Chemical group 0.000 claims 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102015200699.9A DE102015200699A1 (de) | 2015-01-19 | 2015-01-19 | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
| DE102015200699.9 | 2015-01-19 | ||
| PCT/EP2015/078749 WO2016116202A1 (de) | 2015-01-19 | 2015-12-07 | Aminophosphazen-basen als n-dotierstoffe in der organischen elektronik |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018505162A JP2018505162A (ja) | 2018-02-22 |
| JP2018505162A5 true JP2018505162A5 (enExample) | 2018-04-12 |
| JP6526211B2 JP6526211B2 (ja) | 2019-06-05 |
Family
ID=55022423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017537399A Expired - Fee Related JP6526211B2 (ja) | 2015-01-19 | 2015-12-07 | 有機エレクトロニクスにおけるn−ドーパントとしてのアミノフォスファゼン塩基 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10230050B2 (enExample) |
| EP (1) | EP3230295B1 (enExample) |
| JP (1) | JP6526211B2 (enExample) |
| KR (1) | KR102073261B1 (enExample) |
| CN (1) | CN107210364B (enExample) |
| DE (1) | DE102015200699A1 (enExample) |
| WO (1) | WO2016116202A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015200699A1 (de) | 2015-01-19 | 2016-07-21 | Siemens Aktiengesellschaft | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
| CN108239117B (zh) * | 2016-12-26 | 2020-08-14 | 青岛博远高分子材料研究院有限公司 | 环状寡聚磷腈化合物及其制备方法和用途 |
| JP7092381B2 (ja) | 2016-12-26 | 2022-06-28 | 青島科技大学 | オリゴホスファゼン化合物及びその調製方法と使用 |
| JP7232016B2 (ja) * | 2018-11-15 | 2023-03-02 | 日本放送協会 | 有機薄膜および有機薄膜の製造方法、有機エレクトロルミネッセンス素子、表示装置、照明装置、有機薄膜太陽電池、薄膜トランジスタ、塗料組成物 |
| CN110172275A (zh) * | 2019-05-22 | 2019-08-27 | 深圳市华星光电半导体显示技术有限公司 | 电子传输层墨水及其制备方法、电致发光器件 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0512990A (ja) * | 1991-06-27 | 1993-01-22 | Canon Inc | Mim型電子放出素子の製造方法 |
| WO2005034260A1 (de) * | 2003-09-19 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
| JP2006278549A (ja) * | 2005-03-28 | 2006-10-12 | Fuji Photo Film Co Ltd | 有機el素子及び有機elディスプレイ |
| US7683536B2 (en) | 2005-03-31 | 2010-03-23 | The Trustees Of Princeton University | OLEDs utilizing direct injection to the triplet state |
| EP1837927A1 (de) | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
| EP1837926B1 (de) * | 2006-03-21 | 2008-05-07 | Novaled AG | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
| JP5683104B2 (ja) * | 2006-03-21 | 2015-03-11 | ノヴァレッド・アクチエンゲゼルシャフト | ドープされた有機半導体材料の製造方法及びそのために用いられる配合物 |
| JP5393945B2 (ja) * | 2006-07-31 | 2014-01-22 | ポリプラスチックス株式会社 | 安定化ポリアセタール樹脂の製造方法、安定化ポリアセタール樹脂、組成物及び成形体 |
| KR102028264B1 (ko) | 2008-06-20 | 2019-10-02 | 유디씨 아일랜드 리미티드 | 환형 포스파젠 화합물 및 유기 발광 다이오드에서 이의 용도 |
| JP2010062334A (ja) * | 2008-09-03 | 2010-03-18 | Japan Vam & Poval Co Ltd | リン拡散用塗布液 |
| US20110266525A1 (en) | 2009-10-29 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| CN103180993B (zh) * | 2010-11-09 | 2016-01-27 | 皇家飞利浦电子股份有限公司 | 有机电致发光器件 |
| EP2724389B1 (de) * | 2011-06-22 | 2018-05-16 | Novaled GmbH | Organisches elektronisches bauelement |
| EP3667752A1 (en) * | 2011-06-22 | 2020-06-17 | Novaled GmbH | Electronic device and compound |
| DE102012217587A1 (de) * | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik |
| JP6305391B2 (ja) * | 2013-03-05 | 2018-04-04 | 株式会社Kyulux | 電荷輸送材料、ホスト材料、薄膜および有機発光素子 |
| DE102014100993A1 (de) * | 2013-12-05 | 2015-06-11 | Osram Opto Semiconductors Gmbh | Organisches lichtemittierendes Bauelement und Verfahren zur Herstellung des organischen lichtemittierenden Bauelements |
| DE102015200699A1 (de) | 2015-01-19 | 2016-07-21 | Siemens Aktiengesellschaft | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
-
2015
- 2015-01-19 DE DE102015200699.9A patent/DE102015200699A1/de not_active Withdrawn
- 2015-12-07 WO PCT/EP2015/078749 patent/WO2016116202A1/de not_active Ceased
- 2015-12-07 US US15/544,490 patent/US10230050B2/en not_active Expired - Fee Related
- 2015-12-07 EP EP15816100.0A patent/EP3230295B1/de not_active Not-in-force
- 2015-12-07 KR KR1020177023143A patent/KR102073261B1/ko not_active Expired - Fee Related
- 2015-12-07 JP JP2017537399A patent/JP6526211B2/ja not_active Expired - Fee Related
- 2015-12-07 CN CN201580073924.7A patent/CN107210364B/zh not_active Expired - Fee Related
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