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 |
|---|---|---|---|
| DE102015200699.9 | 2015-01-19 | ||
| DE102015200699.9A DE102015200699A1 (de) | 2015-01-19 | 2015-01-19 | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
| 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 (https=) | 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 (https=) |
| EP (1) | EP3230295B1 (https=) |
| JP (1) | JP6526211B2 (https=) |
| KR (1) | KR102073261B1 (https=) |
| CN (1) | CN107210364B (https=) |
| DE (1) | DE102015200699A1 (https=) |
| WO (1) | WO2016116202A1 (https=) |
Families Citing this family (6)
| 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 |
| WO2018121005A1 (zh) * | 2016-12-26 | 2018-07-05 | 青岛科技大学 | 寡聚磷腈化合物及其制备方法和用途 |
| 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 |
| 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 |
| US20240166824A1 (en) * | 2021-03-02 | 2024-05-23 | Nippon Shokubai Co., Ltd. | Phosphazene bond-containing polymer |
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 |
| CN1853288B (zh) * | 2003-09-19 | 2010-12-15 | 默克专利有限公司 | 有机电致发光元件 |
| 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 |
| KR101361710B1 (ko) * | 2006-03-21 | 2014-02-10 | 노발레드 아게 | 도핑된 유기 반도체 물질을 제조하는 방법 및 이러한 방법에 사용되는 포뮬레이션 |
| 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 |
| 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 |
| CN102099942B (zh) | 2008-06-20 | 2013-05-15 | 巴斯夫欧洲公司 | 环状磷腈化合物及其在有机发光二极管中的用途 |
| 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 |
| US9502660B2 (en) * | 2011-06-22 | 2016-11-22 | Novaled Gmbh | Electronic device and compound |
| US20140203254A1 (en) | 2011-06-22 | 2014-07-24 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Organic Electronic Component |
| DE102012217587A1 (de) * | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik |
| WO2014136758A1 (ja) | 2013-03-05 | 2014-09-12 | 国立大学法人九州大学 | 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 KR KR1020177023143A patent/KR102073261B1/ko not_active Expired - Fee Related
- 2015-12-07 CN CN201580073924.7A patent/CN107210364B/zh not_active Expired - Fee Related
- 2015-12-07 JP JP2017537399A patent/JP6526211B2/ja not_active Expired - Fee Related
- 2015-12-07 US US15/544,490 patent/US10230050B2/en not_active Expired - Fee Related
- 2015-12-07 WO PCT/EP2015/078749 patent/WO2016116202A1/de not_active Ceased
- 2015-12-07 EP EP15816100.0A patent/EP3230295B1/de not_active Not-in-force
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