JP2014507383A5 - - Google Patents
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- JP2014507383A5 JP2014507383A5 JP2013543646A JP2013543646A JP2014507383A5 JP 2014507383 A5 JP2014507383 A5 JP 2014507383A5 JP 2013543646 A JP2013543646 A JP 2013543646A JP 2013543646 A JP2013543646 A JP 2013543646A JP 2014507383 A5 JP2014507383 A5 JP 2014507383A5
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- Prior art keywords
- alkyl
- group
- aryl
- substituted
- compound
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 10
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000005286 illumination Methods 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 230000000007 visual effect Effects 0.000 claims 2
- 230000005669 field effect Effects 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- 108091008695 photoreceptors Proteins 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BYDMGWHTARYHKO-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenylpyrimidine Chemical compound BrC1=CC=CC(C=2N=C(C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BYDMGWHTARYHKO-UHFFFAOYSA-N 0.000 description 1
- BPMSGKUGXMWVBH-UHFFFAOYSA-N 4-(3-bromophenyl)-2,6-diphenylpyrimidine Chemical compound BrC1=CC=CC(C=2N=C(N=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BPMSGKUGXMWVBH-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-N cyclopenta-1,3-dien-1-yl(diphenyl)phosphanium;dichloropalladium;iron(2+) Chemical compound [Cl-].[Cl-].[Fe+2].[Pd+2].C1=C[CH-]C([PH+](C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C([PH+](C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10194757 | 2010-12-13 | ||
| EP10194757.0 | 2010-12-13 | ||
| PCT/EP2011/072040 WO2012080052A1 (en) | 2010-12-13 | 2011-12-07 | Bispyrimidines for electronic applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016137575A Division JP2016183190A (ja) | 2010-12-13 | 2016-07-12 | 電子装置用途のためのビスピリミジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014507383A JP2014507383A (ja) | 2014-03-27 |
| JP2014507383A5 true JP2014507383A5 (https=) | 2016-09-01 |
| JP6012024B2 JP6012024B2 (ja) | 2016-10-25 |
Family
ID=45099108
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013543646A Active JP6012024B2 (ja) | 2010-12-13 | 2011-12-07 | 電子装置用途のためのビスピリミジン |
| JP2016137575A Pending JP2016183190A (ja) | 2010-12-13 | 2016-07-12 | 電子装置用途のためのビスピリミジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016137575A Pending JP2016183190A (ja) | 2010-12-13 | 2016-07-12 | 電子装置用途のためのビスピリミジン |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2651904B1 (https=) |
| JP (2) | JP6012024B2 (https=) |
| KR (2) | KR101979693B1 (https=) |
| CN (1) | CN103261171B (https=) |
| WO (1) | WO2012080052A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103261171B (zh) * | 2010-12-13 | 2016-03-30 | 巴斯夫欧洲公司 | 用于电子应用的双嘧啶类 |
| US9806270B2 (en) | 2011-03-25 | 2017-10-31 | Udc Ireland Limited | 4H-imidazo[1,2-a]imidazoles for electronic applications |
| TWI663154B (zh) | 2011-08-25 | 2019-06-21 | 日商半導體能源研究所股份有限公司 | 發光元件，發光裝置，電子裝置，照明裝置以及新穎有機化合物 |
| KR102021099B1 (ko) | 2011-11-10 | 2019-09-16 | 유디씨 아일랜드 리미티드 | 전자장치 응용을 위한 4h-이미다조[1,2-a]이미다졸 |
| EP2872512B1 (en) | 2012-07-10 | 2017-05-10 | UDC Ireland Limited | Benzimidazo[1,2-a]benzimidazole derivatives for electronic applications |
| EP3248966B1 (en) | 2015-01-20 | 2022-12-21 | Hodogaya Chemical Co., Ltd. | Pyrimidine derivatives and organic electroluminescent devices |
| US20180182980A1 (en) * | 2015-06-03 | 2018-06-28 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
| KR101962758B1 (ko) | 2015-06-17 | 2019-03-27 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
| EP3284801A1 (en) * | 2016-08-19 | 2018-02-21 | Julius-Maximilians-Universität Würzburg | Ligands, electrochromic metallo-polymers obtained therewith and their use |
| WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | Substituted cyclopropyl derivatives |
| KR101847347B1 (ko) * | 2017-06-30 | 2018-04-09 | 주식회사 두산 | 유기 화합물 및 이를 이용한 유기 전계 발광 소자 |
| KR101884130B1 (ko) * | 2017-08-29 | 2018-07-31 | 주식회사 두산 | 유기 전계 발광 소자 |
| CN107827826A (zh) * | 2017-11-02 | 2018-03-23 | 上海道亦化工科技有限公司 | 一种嘧啶衍生物及其用途和有机电致发光器件 |
| KR102423551B1 (ko) * | 2017-11-03 | 2022-07-22 | 솔루스첨단소재 주식회사 | 전자수송층용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| KR20190070586A (ko) | 2017-12-13 | 2019-06-21 | 엘지디스플레이 주식회사 | 전자수송 재료용 화합물 및 이를 포함하는 유기 발광 다이오드 |
| WO2020012685A1 (ja) * | 2018-07-09 | 2020-01-16 | コニカミノルタ株式会社 | 薄膜、電子デバイス、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用材料、表示装置、及び、照明装置 |
| JP7406500B2 (ja) * | 2018-10-17 | 2023-12-27 | 保土谷化学工業株式会社 | ピリミジン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
| JP7206816B2 (ja) * | 2018-11-01 | 2023-01-18 | 東ソー株式会社 | 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子 |
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| KR101577465B1 (ko) | 2007-07-05 | 2015-12-14 | 바스프 에스이 | 카르벤 전이 금속 착체 이미터, 및 디실릴카르바졸, 디실릴디벤조푸란, 디실릴디벤조티오펜, 디실릴디벤조포스폴, 디실릴디벤조티오펜 ｓ-옥사이드 및 디실릴디벤조티오펜 ｓ,ｓ-디옥사이드로부터 선택된 1종 이상의 화합물을 포함하는 유기 발광 다이오드 |
| JP2010241687A (ja) | 2007-07-07 | 2010-10-28 | Idemitsu Kosan Co Ltd | クリセン誘導体、及び、有機ｅｌ素子 |
| JP5194596B2 (ja) | 2007-07-11 | 2013-05-08 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| KR100904070B1 (ko) | 2007-07-18 | 2009-06-23 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 이용한 유기광전소자 |
| WO2009037155A1 (en) | 2007-09-20 | 2009-03-26 | Basf Se | Electroluminescent device |
| US8101290B2 (en) | 2007-10-17 | 2012-01-24 | Technical Institute Of Physics And Chemistry Of Chinese Academy Of Sciences | Organic compound having electron-transporting and/or hole-blocking performance and its use and OLEDs comprising the compound |
| WO2009054253A1 (ja) | 2007-10-26 | 2009-04-30 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| WO2009069442A1 (ja) | 2007-11-26 | 2009-06-04 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| JP5317470B2 (ja) * | 2007-12-27 | 2013-10-16 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| KR101504266B1 (ko) | 2007-12-27 | 2015-03-19 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 유기 전계 발광소자용 화합물 및 이것을 사용한 유기 전계 발광소자 |
| JP5207760B2 (ja) | 2008-02-07 | 2013-06-12 | ケミプロ化成株式会社 | 新規なピリミジン系またはトリアジン系誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子 |
| KR101919207B1 (ko) | 2008-11-11 | 2018-11-15 | 유니버셜 디스플레이 코포레이션 | 인광성 에미터 |
| JP5707665B2 (ja) * | 2008-12-03 | 2015-04-30 | 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、該素子を備えた照明装置及び表示装置 |
| US9458182B2 (en) | 2009-01-07 | 2016-10-04 | Basf Se | Silyl- and heteroatom-substituted compounds selected from carbazoles, dibenzofurans, dibenzothiophenes and dibenzophospholes, and use thereof in organic electronics |
| DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
| WO2010090077A1 (ja) * | 2009-02-06 | 2010-08-12 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
| TWI687408B (zh) | 2009-04-28 | 2020-03-11 | 美商環球展覽公司 | 具有甲基-ｄ３取代之銥錯合物 |
| JP4523992B1 (ja) | 2009-07-31 | 2010-08-11 | 富士フイルム株式会社 | 有機電界発光素子 |
| EP2513125B1 (de) | 2009-12-14 | 2014-10-29 | Basf Se | Metallkomplexe, enthaltend diazabenzimidazolcarben-liganden und deren verwendung in oleds |
| CN103261171B (zh) * | 2010-12-13 | 2016-03-30 | 巴斯夫欧洲公司 | 用于电子应用的双嘧啶类 |
-
2011
- 2011-12-07 CN CN201180059544.XA patent/CN103261171B/zh active Active
- 2011-12-07 KR KR1020137018293A patent/KR101979693B1/ko active Active
- 2011-12-07 JP JP2013543646A patent/JP6012024B2/ja active Active
- 2011-12-07 KR KR1020197013664A patent/KR102122490B1/ko active Active
- 2011-12-07 WO PCT/EP2011/072040 patent/WO2012080052A1/en not_active Ceased
- 2011-12-07 EP EP11791571.0A patent/EP2651904B1/en active Active
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2016
- 2016-07-12 JP JP2016137575A patent/JP2016183190A/ja active Pending
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