CA2851429A1 - Heteroleptic copper complexes for optoelectronic applications - Google Patents
Heteroleptic copper complexes for optoelectronic applications Download PDFInfo
- Publication number
- CA2851429A1 CA2851429A1 CA2851429A CA2851429A CA2851429A1 CA 2851429 A1 CA2851429 A1 CA 2851429A1 CA 2851429 A CA2851429 A CA 2851429A CA 2851429 A CA2851429 A CA 2851429A CA 2851429 A1 CA2851429 A1 CA 2851429A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- branched
- cyclic
- aryl
- heteroaryl
- 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.)
- Abandoned
Links
- 230000005693 optoelectronics Effects 0.000 title claims abstract description 25
- 150000001879 copper Chemical class 0.000 title description 2
- 239000003446 ligand Substances 0.000 claims abstract description 100
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 98
- 125000003118 aryl group Chemical group 0.000 claims abstract description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 59
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 49
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 18
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 18
- -1 1,2,3,4-oxatriazolyl Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims abstract description 15
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 9
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims abstract description 7
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims abstract description 7
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims abstract description 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims abstract description 7
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 7
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims abstract description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 7
- 125000004306 triazinyl group Chemical group 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 125000004122 cyclic group Chemical group 0.000 claims description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
- 239000007787 solid Substances 0.000 claims description 53
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 150000002148 esters Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000004020 conductor Substances 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000007942 carboxylates Chemical class 0.000 claims description 16
- 239000002800 charge carrier Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 150000002466 imines Chemical group 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
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- 238000006467 substitution reaction Methods 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 238000000859 sublimation Methods 0.000 claims description 3
- 230000008022 sublimation Effects 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 157
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 78
- 238000012512 characterization method Methods 0.000 description 49
- 238000000921 elemental analysis Methods 0.000 description 48
- 238000000295 emission spectrum Methods 0.000 description 48
- 239000010949 copper Substances 0.000 description 26
- 239000010410 layer Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000006870 function Effects 0.000 description 11
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 239000005922 Phosphane Substances 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000002105 nanoparticle Substances 0.000 description 6
- 229910000064 phosphane Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 0 C[C@](C*)*(C*CC(*)C[C@](*)C1)C[C@]1N=O Chemical compound C[C@](C*)*(C*CC(*)C[C@](*)C1)C[C@]1N=O 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910017489 Cu I Inorganic materials 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
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- 230000006798 recombination Effects 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 5
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- 230000008859 change Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052802 copper Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004699 copper complex Chemical class 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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- C07F9/50—Organo-phosphines
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- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11189397.0 | 2011-11-16 | ||
| EP11189397 | 2011-11-16 | ||
| EP11195010.1A EP2594571A1 (de) | 2011-11-16 | 2011-12-21 | Kupfer-Komplexe für optoelektronische Anwendungen |
| EP11195010.1 | 2011-12-21 | ||
| PCT/EP2012/072927 WO2013072508A1 (de) | 2011-11-16 | 2012-11-16 | Heteroleptische kupfer-komplexe für optoelektronische anwendungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2851429A1 true CA2851429A1 (en) | 2013-05-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2851429A Abandoned CA2851429A1 (en) | 2011-11-16 | 2012-11-16 | Heteroleptic copper complexes for optoelectronic applications |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9985225B2 (enExample) |
| EP (2) | EP2594571A1 (enExample) |
| JP (1) | JP5908105B2 (enExample) |
| KR (1) | KR20140093959A (enExample) |
| CN (1) | CN104066740B (enExample) |
| CA (1) | CA2851429A1 (enExample) |
| HK (1) | HK1201840A1 (enExample) |
| WO (1) | WO2013072508A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009030475A1 (de) * | 2009-06-24 | 2011-01-05 | Hartmut Prof. Dr. Yersin | Kupfer-Komplexe für optoelektronische Anwendungen |
| KR102796297B1 (ko) | 2013-12-20 | 2025-04-17 | 유디씨 아일랜드 리미티드 | 매우 짧은 감쇠 시간을 갖는 고효율 ｏｌｅｄ 장치 |
| EP2993176A1 (de) | 2014-09-02 | 2016-03-09 | cynora GmbH | Metall(i)-komplexe für verbesserte leitfähigkeit |
| DE102015216658A1 (de) | 2014-09-02 | 2016-03-03 | Cynora Gmbh | Strukturell Stabilisierte Kupfer(I)-Komplexe |
| WO2016037963A1 (de) | 2014-09-08 | 2016-03-17 | Cynora Gmbh | Stabilisierte optisch aktive schicht und verfahren zur herstellung |
| WO2016037964A1 (de) | 2014-09-08 | 2016-03-17 | Cynora Gmbh | Verbesserte optisch aktive schicht und verfahren zur herstellung |
| WO2016041802A1 (en) | 2014-09-16 | 2016-03-24 | Cynora Gmbh | Light-emitting layer suitable for bright luminescence |
| WO2016079097A1 (de) * | 2014-11-18 | 2016-05-26 | Cynora Gmbh | Kupfer(i)komplexe für optoelektronische anwendungen |
| CN111668392B (zh) | 2015-06-03 | 2024-01-23 | Udc 爱尔兰有限责任公司 | 具有极短衰减时间的高效oled装置 |
| CN104961770B (zh) * | 2015-06-17 | 2017-05-31 | 中国计量学院 | 一种基于吡啶基膦配体的亚铜配合物绿色磷光材料 |
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| JP3965319B2 (ja) | 2001-03-08 | 2007-08-29 | ザ ユニヴァーシティ オブ ホンコン | 有機金属発光材料 |
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| CN101172986A (zh) | 2002-08-16 | 2008-05-07 | 南加利福尼亚大学 | 含阴离子配体的有机发光材料 |
| EP1534799A4 (en) | 2002-08-16 | 2008-02-27 | Univ Southern California | ORGANIC FLUORES AND CORRESPONDING DEVICES |
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| JP4557651B2 (ja) * | 2003-10-01 | 2010-10-06 | キヤノン株式会社 | 発光性銅配位化合物及び有機発光素子 |
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| DE102004032527A1 (de) | 2004-07-06 | 2006-02-02 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
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| US20060073360A1 (en) | 2004-09-28 | 2006-04-06 | Fuji Photo Film Co., Ltd. | Organic electroluminescent device |
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| DE102009030475A1 (de) * | 2009-06-24 | 2011-01-05 | Hartmut Prof. Dr. Yersin | Kupfer-Komplexe für optoelektronische Anwendungen |
| CN102010448B (zh) * | 2010-11-12 | 2013-02-13 | 中国科学院长春应用化学研究所 | 铜(i)配合物及其应用 |
| EP2540730A1 (de) | 2011-06-29 | 2013-01-02 | cynora GmbH | Kupfer(I)komplexe, insbesondere für optoelektronische Bauelemente |
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- 2012-11-16 KR KR1020147013915A patent/KR20140093959A/ko not_active Withdrawn
- 2012-11-16 EP EP12809626.0A patent/EP2780345B1/de active Active
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|---|---|
| CN104066740B (zh) | 2017-05-10 |
| EP2780345A1 (de) | 2014-09-24 |
| HK1201840A1 (en) | 2015-09-11 |
| EP2780345B1 (de) | 2017-04-12 |
| JP5908105B2 (ja) | 2016-04-26 |
| US9985225B2 (en) | 2018-05-29 |
| JP2015505820A (ja) | 2015-02-26 |
| EP2594571A1 (de) | 2013-05-22 |
| CN104066740A (zh) | 2014-09-24 |
| WO2013072508A1 (de) | 2013-05-23 |
| KR20140093959A (ko) | 2014-07-29 |
| US20140326981A1 (en) | 2014-11-06 |
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