JP2017025102A - N−1に結合した捻じれたアリール基をもつ1又は2つのイミダゾール環を含むシクロメタル化四座配位Pt(II)錯体 - Google Patents
N−1に結合した捻じれたアリール基をもつ1又は2つのイミダゾール環を含むシクロメタル化四座配位Pt(II)錯体 Download PDFInfo
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- JP2017025102A JP2017025102A JP2016210601A JP2016210601A JP2017025102A JP 2017025102 A JP2017025102 A JP 2017025102A JP 2016210601 A JP2016210601 A JP 2016210601A JP 2016210601 A JP2016210601 A JP 2016210601A JP 2017025102 A JP2017025102 A JP 2017025102A
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- aryl
- deuterium
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- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 125000003118 aryl group Chemical group 0.000 claims abstract description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 239000010410 layer Substances 0.000 claims description 71
- -1 heteroalkenyl Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 37
- 229910052805 deuterium Inorganic materials 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 125000002252 acyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004104 aryloxy group Chemical group 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 28
- 150000004820 halides Chemical class 0.000 claims description 28
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 150000002527 isonitriles Chemical class 0.000 claims description 28
- 150000002825 nitriles Chemical class 0.000 claims description 28
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 28
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 28
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 28
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002019 doping agent Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000004696 coordination complex Chemical group 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 101100118680 Caenorhabditis elegans sec-61.G gene Proteins 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 34
- 229910052697 platinum Inorganic materials 0.000 abstract description 11
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 10
- 239000000463 material Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- 230000032258 transport Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
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- 235000019439 ethyl acetate Nutrition 0.000 description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940125898 compound 5 Drugs 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- RULKYCDPDKSMSH-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)imidazol-4-yl]-n-phenyl-n-(3-pyrazol-1-ylphenyl)aniline Chemical compound CC1=CC=CC(C)=C1N1C=C(C=2C=C(C=CC=2)N(C=2C=CC=CC=2)C=2C=C(C=CC=2)N2N=CC=C2)N=C1 RULKYCDPDKSMSH-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- VFFHONDIWPCSCM-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)imidazol-4-yl]-n-phenylaniline Chemical compound CC1=CC=CC(C)=C1N1C=C(C=2C=C(NC=3C=CC=CC=3)C=CC=2)N=C1 VFFHONDIWPCSCM-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
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- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical class [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
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- 229910052796 boron Inorganic materials 0.000 description 2
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- 239000013522 chelant Substances 0.000 description 2
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- QTUGGVBKWIYQSS-UHFFFAOYSA-N 2-iodo-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1I QTUGGVBKWIYQSS-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- BBGBAQOVSYJWBC-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)imidazol-4-yl]-n-[3-[1-(2,6-dimethylphenyl)imidazol-4-yl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(C)=C1N1C=C(C=2C=C(C=CC=2)N(C=2C=CC=CC=2)C=2C=C(C=CC=2)C=2N=CN(C=2)C=2C(=CC=CC=2C)C)N=C1 BBGBAQOVSYJWBC-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- GBKYFASVJPZWLI-UHFFFAOYSA-N [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 Chemical compound [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 GBKYFASVJPZWLI-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- QKVWPNRUXZYLQV-UHFFFAOYSA-N c(cc1c2ccc3)ccc1[s]c2c3-c1cc(-c(cc2)cc3c2c2ccccc2c2ccccc32)ccc1 Chemical compound c(cc1c2ccc3)ccc1[s]c2c3-c1cc(-c(cc2)cc3c2c2ccccc2c2ccccc32)ccc1 QKVWPNRUXZYLQV-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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Abstract
Description
一般に、OLEDは、アノードとカソードとの間に配置され且つそれらと電気的に接続された少なくとも1つの有機層を含む。電流が流された場合、有機層(1又は複数)にアノードは正孔を注入し、カソードは電子を注入する。注入された正孔と電子はそれぞれ反対に帯電した電極に向かって移動する。電子と正孔が同じ分子上に局在する場合、励起エネルギー状態を有する局在化された電子−正孔対である「励起子」が形成される。励起子が発光機構によって緩和するときに光が発せられる。いくつかの場合には、励起子はエキシマー又はエキシプレックス上に局在化されうる。非放射機構、例えば、熱緩和も起こりうるが、通常は好ましくないと考えられる。
及び、Baldoら,“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”)、これらを参照により全体を援用する。燐光は、米国特許第7,279,704号明細書の第5〜6欄に、より詳細に記載されており、これを参照により援用する。
新規な群の四座配位白金(II)化合物を提供する(図3に示すとおりである)。これらの化合物は、(i)それぞれが少なくとも1つの5員の炭素環又はヘテロ環を含む2つの配位子を含み、(ii)それらの配位子のうちの1つが、N−1に結合したねじれた(twisted)アリール基をもつイミダゾール環を含み、且つ(iii)そのイミダゾールと同じ配位子中に、炭素原子を介して白金に結合した6員の炭素環又はヘテロ環を含む。これらの特徴は、これらを一緒にして、それらの化合物をOLEDに用いるために特に適したものにしうる。
有機発光デバイス中の具体的な層に有用として本明細書に記載した物質は、そのデバイス中に存在するその他の広範囲にわたる物質と組み合わせて用いることができる。例えば、本明細書に開示した発光ドーパントは、存在してもよい広い範囲のホスト、輸送層、阻止層、注入層、電極、及びその他の層と組み合わせて用いることができる。以下に記載乃至言及した物質は、本明細書に記載した化合物と組み合わせて有用でありうる物質の非限定例であり、当業者は組み合わせて有用でありうるその他の物質を特定するために文献を容易に参考にすることができる。
フタロシアニン又はポルフィリン誘導体;芳香族アミン誘導体;インドロカルバゾール誘導体;フルオロ炭化水素を含むポリマー;導電性ドーパントを伴うポリマー;導電性ポリマー、例えば、PEDOT/PSS;ホスホン酸及びシラン誘導体などの化合物から誘導される自己組織化モノマー;金属酸化物誘導体、例えば、MoOx;p型半導体有機化合物、例えば、1,4,5,8,9,12−ヘキサアザトリフェニレンヘキサカルボニトリル;金属錯体、及び架橋性化合物。
80mLのホルムアミド中の2−ブロモ−1−(3−クロロフェニル)エタノン(20.15 g, 86 mmol)を250mLの丸底フラスコに入れ、その反応混合物を165℃に2.5時間加熱した。その反応物を次に冷やして、固体を濾過し、水で洗った。濾液をpH12に塩基性化し、酢酸エチルで抽出した。有機層を粗生成物固体と一緒にし、DCM中3〜5%MeOHを用いてシリカゲル上でクロマトグラフィーにかけて、10.9g(71%)の4−(3−クロロフェニル)−1H−イミダゾールを固体として得た。
耐圧フラスコに4−(3−クロロフェニル)−1H−イミダゾール(10.82 g, 60.6 mmol)及び2−ヨード−1,3−ジメチルベンゼン(16.87 g, 72.7 mmol)を仕込んだ。その反応混合物をDMF(60 mL)で希釈し、ヨウ化銅(I)(1.1 g, 6.1 mmol)、N,N−ジメチルエタン−1,2−ジアミン(2.6 mL, 24.2 mmol)、及び炭酸セシウム(23.68 g, 72.7 mmol)を添加した。窒素で脱ガスした後、反応混合物を油浴中で160℃に48時間撹拌し、その後、酢酸エチルで希釈し、セライトを通して濾過した。濾液をLiCl水溶液、食塩水、及び水で洗った。生成物を、DCM中0〜5%のEtOAcを用いてシリカゲル上でのクロマトグラフィーによって精製して、3.8g(22%)の4−(3−クロロフェニル)−1−(2,6−ジメチルフェニル)−1H−イミダゾールを得た。
トルエン(200 mL)中の4−(3−クロロフェニル)−1−(2,6−ジメチルフェニル)−1H−イミダゾール(5.4 g, 19.1 mmol)とアニリン(0.87 ml, 9.5 mmol)を、500mL丸底フラスコ中に入れた。ナトリウムtert−ブトキシド(4.0 g, 41.9 mmol)とジシクロへキシル(2′,6′−ジメトキシ−[1,1′−ビフェニル]−2−イル)ホスフィン(0.783 g, 1.906 mmol)を添加し、その反応混合物を脱ガスした後、Pd2(dba)3(0.44 g, 0.48 mmol)を添加した。これを脱気し、窒素を入れて満たした。反応物を24時間還流しながら撹拌した。その混合物を次にセライトを通して濾過した。次に、濾液を濃縮し、ヘキサン中10〜25%酢酸エチル、次にDCM中10%酢酸エチルを用いてシリカゲル上でのクロマトグラフィーにかけて、2.8g(51%)の3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−(3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)フェニル)−N−フェニルアニリンを白色固体として得た。
酢酸(100 mL)中の3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−(3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)フェニル)−N−フェニルアニリン(1.7 g, 2.9 mmol)及び四塩化白金酸カリウム(1.2 g, 2.9 mmol)を250mLのフラスコに入れ、赤色の懸濁液を得た。その懸濁液を窒素でパージした。その反応混合物を48時間還流しながら撹拌し、その時点で室温に冷やし、100mLの水を添加した。生成物を濾過し、2:1のジクロロメタン:ヘキサンを用いてシリカ上でのカラムクロマトグラフィーによって精製して、0.72g(33%)の化合物1を黄色固体として得た。
500mLの丸底フラスコに、トルエン(200 mL)中の4−(3−クロロフェニル)−1−(2,6−ジメチルフェニル)−1H−イミダゾール(5.39 g, 19.06 mmol)とアニリン(0.870 mL, 9.53 mmol)を仕込んだ。ナトリウムtert−ブトキシド(4.03 g, 41.9 mmol)及びジシクロへキシル(2′,6′−ジメトキシ−[1,1′−ビフェニル]−2−イル)ホスフィン(0.783 g, 1.90 mmol)を添加し、その反応混合物を窒素で脱ガスした後、Pd2(dba)3(0.436 g, 0.477 mmol)を添加した。その反応フラスコを脱気し、窒素を入れて満たし、次に24時間還流しながら撹拌した。セライトを通して未反応混合物を濾過し、濾液を減圧下で濃縮し、ジクロロメタン中10%酢酸エチルを用いるカラムクロマトグラフィーを用いて精製して、1.4g(42%)の3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−フェニルアニリンを固体として得た。
ジオキサン(400 mL)中の1−ブロモ−3−ヨードベンゼン(18.20 g, 64.3 mmol)、1H−ピラゾール(4.38 g, 64.3 mmol)及び(1S,2S)−シクロヘキサン−1,2−ジアミン(1.5 g, 12.9 mmol)を、1Lの丸底フラスコに入れた。ヨウ化銅(I)(0.613 g, 3.22 mmol)及び炭酸カリウム(17.78 g, 129 mmol)を添加し、反応混合物を19時間還流させながら撹拌した。未精製混合物を次ぎにセライトの詰め物を通して濾過した。濾液を400mLのジクロロメタンで希釈し、水で洗った。有機層を濃縮し、ヘキサン中5%酢酸エチルを用いてシリカゲル上でのクロマトグラフィーにかけて、7.3g(51%)の1−(3−ブロモフェニル)−1H−ピラゾールを白色固体として得た。
250mLの丸底フラスコに、トルエン(80 mL)中の3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−フェニルアニリン(1.35 g, 3.98 mmol)、1−(3−ブロモフェニル)−1H−ピラゾール(0.89 g, 3.98 mmol)、及びナトリウムtert−ブトキシド(0.459 g, 4.77 mmol)を仕込んだ。Pd2(dba)3(0.091 g, 0.099 mmol)及びジシクロへキシル(2′,6′−ジメトキシ−[1,1′−ビフェニル]−2−イル)ホスフィン(0.163 g, 0.398 mmol)を添加した。反応フラスコを脱気し、窒素を入れて満たした(2回)。その反応物を18時間還流しながら撹拌し、その時間の後、未精製混合物を濃縮し、ジクロロメタン−ヘキサン1:1、次にジクロロメタン、最後にジクロロメタン中1〜5%酢酸エチルで勾配をつけたもので溶離させることを含むカラムクロマトグラフィーを使用して精製した。これによって、1.18g(62%)のN−(3−(1H−ピラゾール−1−イル)フェニル)−3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−フェニルアニリンを淡黄色泡状物として得た。
N−(3−(1H−ピラゾール−1−イル)フェニル)−3−(1−(2,6−ジメチルフェニル)−1H−イミダゾール−4−イル)−N−フェニルアニリン(1.2 g, 2.5 mmol)及び四塩化白金酸カリウム(1.0 g, 2.5 mmol)を酢酸(100 mL)に添加し、その混合物を、窒素を用いて完全に脱ガスさせ、次に130℃(浴温度)に14時間加熱した。その反応物を室温に冷やし、100mLの水を添加した。20分間撹拌した後、反応混合物を小さなセライト床を通して濾過し、多量の水と次にメタノールで洗った。乾燥させた後、DCMを用いて、セライトから固体を洗い流した。得られた濾液をロータリーエバポレーターで蒸発させて1.4gの黄色固体を得た。その未精製物質を、9:1のDCM:ヘキサンを用いてシリカゲル上でのクロマトグラフィーにかけて、0.94gの化合物2を黄色固体として得た(HPLC純度:97.7%)。生成物はNMR及びLC/MSで確認した。
全てのデバイス例は、高真空(<10−7Torr)熱蒸着によって作製した。アノード電極は、800Åのインジウム錫オキシド(ITO)である。カソードは、10ÅのLiFとそれに続く1000ÅのAlからなる。全てのデバイスは、作製後直ちに窒素グローブボックス(<1ppmのH2O及びO2)中でエポキシ樹脂を用いてシールしたガラス蓋で密封し、吸湿剤をそのパッケージ内に組み込んだ。
Claims (29)
- 下記式を有する化合物。
L1及びL2は独立に、単結合、BR、NR、O、Se、C=O、S=O、SO2、CRR′、SiRR′、及びGeRR′からなる群から選択され;
n1は0又は1であり;
n2は0又は1であり;
n1+n2は少なくとも1に等しく;
Z1及びZ2は独立に、窒素原子又は炭素原子であり;
R1、R2、R3、R4、およびR7は、モノ、ジ、トリ、又はテトラ置換を表すことができ;
R1は任意選択により環Aと縮合していてもよく;
R3は任意選択により環Bと縮合していてもよく;
R4は任意選択により環Cと縮合していてもよく;
R7は任意選択により環Dと縮合していてもよく;
R3及びR4は任意選択により連結して環を形成していてもよく;
環B及び環Cのうち少なくとも1つは、5員の炭素環又はヘテロ環であり;
R1、R2、R3、R4、R5、R6、およびR7は独立に、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びそれらの組み合わせからなる群から選択され;且つ、
R5及びR6のうち少なくとも1つは水素でも重水素でもない。 - R5及びR6のうち少なくとも1つはアルキルである、請求項1に記載の化合物。
- R5及びR6のそれぞれがアルキルである、請求項1に記載の化合物。
- R5及びR6のうち少なくとも1つは、少なくとも3つの炭素を含むアルキルである、請求項1に記載の化合物。
- R5及びR6のうち少なくとも1つはシクロアルキルである、請求項1に記載の化合物。
- R5及びR6のうち少なくとも1つはアリールである、請求項1に記載の化合物。
- R3又はR4が置換アリールである、請求項1に記載の化合物。
- R3又はR4が2,6−二置換アリールである、請求項7に記載の化合物。
- R3及びR4が、
R′1及びR′2のうち少なくとも1つは水素でも重水素でもなく;
Dは5員又は6員の炭素環又はヘテロ環であり、これは任意選択でR′3でさらに置換されていてもよく;且つ、
R′3は、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びそれらの組み合わせからなる群から選択される。)
である、請求項7に記載の化合物。 - 有機発光デバイスを含み、さらに、
アノード;
カソード;及び
前記アノードとカソードの間に配置された有機層を含み、
前記有機層が下記式を有する化合物を含む、第一のデバイス。
L1及びL2は独立に、単結合、BR、NR、O、Se、C=O、S=O、SO2、CRR′、SiRR′、及びGeRR′からなる群から選択され;
n1は0又は1であり;
n2は0又は1であり;
n1+n2は少なくとも1に等しく;
Z1及びZ2は独立に、窒素原子又は炭素原子であり;
R1、R2、R3、R4、およびR7は、モノ、ジ、トリ、又はテトラ置換を表すことができ;
R1は任意選択により環Aと縮合していてもよく;
R3は任意選択により環Bと縮合していてもよく;
R4は任意選択により環Cと縮合していてもよく;
R7は任意選択により環Dと縮合していてもよく;
R3及びR4は任意選択により連結して環を形成していてもよく;
環B及び環Cのうち少なくとも1つは、5員の炭素環又はヘテロ環であり;
R1、R2、R3、R4、R5、R6、およびR7は独立に、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びそれらの組み合わせからなる群から選択され;且つ、
R5及びR6のうち少なくとも1つは水素でも重水素でもない。 - 前記有機層が発光層であり、且つ前記化合物が発光ドーパントである、請求項19に記載の第一のデバイス。
- 前記有機層がさらにホストを含む、請求項19に記載の第一のデバイス。
- 前記ホストが、トリフェニレンを有するベンゾ縮合チオフェン又はベンゾ縮合フランを含み;
前記ホスト中のいずれかの置換基が、CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH−CnH2n+1、C≡CHCnH2n+1、Ar1、Ar1−Ar2、CnH2n−Ar1からなる群から選択される非縮合置換基であるか、又は非置換であり、
式中、nは1〜10であり;且つ、
Ar1及びAr2は独立に、ベンゼン、ビフェニル、ナフタレン、トリフェニレン、カルバゾール、及びそれらのヘテロ芳香族類縁体からなる群から選択される、請求項21に記載の第一のデバイス。 - 前記ホストが金属錯体である、請求項21に記載の第一のデバイス。
- 前記有機層が発光層であり、且つ前記化合物が非発光ドーパントである、請求項19に記載の第一のデバイス。
- 消費者製品である、請求項19に記載の第一のデバイス。
- 有機発光デバイスである、請求項19に記載の第一のデバイス。
- 発光パネルを含む、請求項19に記載の第一のデバイス。
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JP6804823B2 (ja) | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーArizona Board of Regents on behalf of Arizona State University | 白金錯体およびデバイス |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
US9847497B2 (en) | 2014-02-18 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9847498B2 (en) * | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10008679B2 (en) | 2014-04-14 | 2018-06-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
CN105273712B (zh) | 2014-07-11 | 2017-07-25 | 广东阿格蕾雅光电材料有限公司 | 用于发光二极管的发光材料 |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
US10793546B2 (en) | 2014-08-15 | 2020-10-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
US9920242B2 (en) | 2014-08-22 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US11329244B2 (en) | 2014-08-22 | 2022-05-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
US9865825B2 (en) | 2014-11-10 | 2018-01-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US11930662B2 (en) | 2015-06-04 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Transparent electroluminescent devices with controlled one-side emissive displays |
US10158091B2 (en) * | 2015-08-04 | 2018-12-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
US10461266B2 (en) * | 2016-06-14 | 2019-10-29 | Queen's University At Kingston | Luminescent compounds and methods of using same |
US10672997B2 (en) * | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3620461B1 (en) | 2016-07-05 | 2022-04-20 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
CN106281301B (zh) * | 2016-08-10 | 2018-10-30 | 青岛大学 | 一种有机磷酸锌光致变色材料及其制备方法 |
US10177323B2 (en) | 2016-08-22 | 2019-01-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
KR20180023297A (ko) * | 2016-08-25 | 2018-03-07 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
KR20240014475A (ko) | 2016-10-12 | 2024-02-01 | 아리조나 보드 오브 리젠츠 온 비하프 오브 아리조나 스테이트 유니버시티 | 협대역 적색 인광성 4좌 백금(ii) 착물 |
US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
US11053268B2 (en) * | 2017-01-20 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2018140765A1 (en) | 2017-01-27 | 2018-08-02 | Jian Li | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
KR102474204B1 (ko) | 2017-07-21 | 2022-12-06 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
US11957044B2 (en) | 2017-09-05 | 2024-04-09 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
EP3461831B1 (en) | 2017-09-29 | 2021-09-01 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
US11594688B2 (en) | 2017-10-17 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
US11825735B2 (en) * | 2017-11-28 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3503234B1 (en) * | 2017-12-20 | 2020-11-04 | Novaled GmbH | Organic electronic device comprising an inverse coordination complex and a method for preparing the same |
KR20200061483A (ko) * | 2018-11-23 | 2020-06-03 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
CN111377970B (zh) * | 2018-12-28 | 2022-12-23 | 广东阿格蕾雅光电材料有限公司 | 一种n`n`c`n型四齿铂(ii)配合物的制备及应用 |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
KR20200115795A (ko) * | 2019-03-26 | 2020-10-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 전자 장치 |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009267170A (ja) * | 2008-04-25 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009267176A (ja) * | 2008-04-25 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009266943A (ja) * | 2008-04-23 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009272339A (ja) * | 2008-04-30 | 2009-11-19 | Fujifilm Corp | 有機電界発光素子 |
JP6061595B2 (ja) * | 2011-09-30 | 2017-01-18 | ユニバーサル ディスプレイ コーポレイション | N−1に結合した捻じれたアリール基をもつ1又は2つのイミダゾール環を含むシクロメタル化四座配位Pt(II)錯体 |
Family Cites Families (158)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
EP0650955B1 (en) | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
EP1325671B1 (en) | 2000-08-11 | 2012-10-24 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
US6893743B2 (en) | 2000-10-04 | 2005-05-17 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
CN100440568C (zh) | 2001-06-20 | 2008-12-03 | 昭和电工株式会社 | 发光材料和有机发光装置 |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
EP2264122A3 (en) | 2002-08-27 | 2011-05-11 | Fujifilm Corporation | Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
EP2241570B1 (en) | 2003-03-24 | 2014-08-13 | University Of Southern California | Biphenyl- and fluorenyl-pyrazole derivatives and iridium complexes thereof |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
US7345301B2 (en) | 2003-04-15 | 2008-03-18 | Merck Patent Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
JP4673744B2 (ja) | 2003-05-29 | 2011-04-20 | 新日鐵化学株式会社 | 有機電界発光素子 |
US7569692B2 (en) | 2003-06-02 | 2009-08-04 | Fujifilm Corporation | Organic electroluminescent devices and metal complex compounds |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
KR101044087B1 (ko) | 2003-11-04 | 2011-06-27 | 다카사고 고료 고교 가부시키가이샤 | 백금 착체 및 발광소자 |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
KR100934890B1 (ko) | 2004-03-11 | 2010-01-06 | 미쓰비시 가가꾸 가부시키가이샤 | 전하 수송막용 조성물 및 이온 화합물, 이를 이용한 전하 수송막 및 유기 전계 발광 장치, 및 유기 전계 발광 장치의제조 방법 및 전하 수송막의 제조 방법 |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4749744B2 (ja) | 2004-03-31 | 2011-08-17 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
US7655323B2 (en) | 2004-05-18 | 2010-02-02 | The University Of Southern California | OLEDs utilizing macrocyclic ligand systems |
US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
JP4894513B2 (ja) | 2004-06-17 | 2012-03-14 | 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材料、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 |
BRPI0512641A (pt) | 2004-06-28 | 2008-03-25 | Ciba Sc Holding Ag | complexos metálicos eletroluminescentes com triazóis e benzotriazóis |
US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
WO2006009024A1 (ja) | 2004-07-23 | 2006-01-26 | 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 |
US7579093B2 (en) * | 2004-09-17 | 2009-08-25 | Fujifilm Corporation | Organic electroluminescent device |
JP4500735B2 (ja) | 2004-09-22 | 2010-07-14 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4531509B2 (ja) | 2004-09-27 | 2010-08-25 | 富士フイルム株式会社 | 発光素子 |
DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
US7597967B2 (en) | 2004-12-17 | 2009-10-06 | Eastman Kodak Company | Phosphorescent OLEDs with exciton blocking layer |
US20060134461A1 (en) | 2004-12-17 | 2006-06-22 | Shouquan Huo | Organometallic materials and electroluminescent devices |
KR101272435B1 (ko) | 2004-12-30 | 2013-06-07 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기금속 착체 |
US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
JP4773109B2 (ja) | 2005-02-28 | 2011-09-14 | 高砂香料工業株式会社 | 白金錯体及び発光素子 |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
US7771845B2 (en) | 2005-03-14 | 2010-08-10 | Fujifilm Corporation | Organic electroluminescent device |
EP2562840A1 (en) | 2005-03-16 | 2013-02-27 | UDC Ireland Limited | Platinum complex compound and organic electroluminescent device |
JP4727262B2 (ja) | 2005-03-16 | 2011-07-20 | 富士フイルム株式会社 | 有機電界発光素子 |
WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | 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材料、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 |
WO2006114966A1 (ja) | 2005-04-18 | 2006-11-02 | 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 |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
CN103746080B (zh) | 2005-05-31 | 2019-03-08 | 通用显示公司 | 发射磷光的二极管中的苯并[9,10]菲基质 |
US8709614B2 (en) | 2005-06-07 | 2014-04-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic metal complex and its use in organic electroluminescent device |
US7638072B2 (en) | 2005-06-27 | 2009-12-29 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
US20090039771A1 (en) | 2005-07-01 | 2009-02-12 | Konica Minolta Holdings, Inc. | Organic electroluminescent element material, organic electroluminescent element, display device and lighting device |
WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
JP4792262B2 (ja) | 2005-09-09 | 2011-10-12 | 富士フイルム株式会社 | 有機電界発光素子及び錯体化合物 |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | 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 |
KR20080085000A (ko) | 2005-12-01 | 2008-09-22 | 신닛테츠가가쿠 가부시키가이샤 | 유기 전계 발광소자 |
EP1956022B1 (en) | 2005-12-01 | 2012-07-25 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
TWI391396B (zh) | 2006-02-10 | 2013-04-01 | Universal Display Corp | 環化金屬之咪唑并〔1,2-f〕啡啶及二咪唑〔1,2-a:1’,2’-c〕喹唑啉配位體的金屬錯合物、與其等電子及苯基化類似物 |
US8142909B2 (en) | 2006-02-10 | 2012-03-27 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
KR101453109B1 (ko) | 2006-04-26 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그들을 이용한 유기 전기 발광 소자 |
EP2018090A4 (en) | 2006-05-11 | 2010-12-01 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENCE DEVICE |
CN101461074B (zh) | 2006-06-02 | 2011-06-15 | 出光兴产株式会社 | 有机电致发光元件用材料及使用了它的有机电致发光元件 |
JP2008037848A (ja) | 2006-08-10 | 2008-02-21 | Takasago Internatl Corp | 白金錯体及び発光素子 |
JP5203207B2 (ja) | 2006-08-23 | 2013-06-05 | 出光興産株式会社 | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | 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材料 |
JP4388590B2 (ja) | 2006-11-09 | 2009-12-24 | 新日鐵化学株式会社 | 有機電界発光素子用化合物及び有機電界発光素子 |
EP2518045A1 (en) | 2006-11-24 | 2012-10-31 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element using the same |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
EP2112994B1 (en) | 2007-02-23 | 2011-01-26 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
JPWO2008108407A1 (ja) | 2007-03-06 | 2010-06-17 | 国立大学法人 長崎大学 | 金属錯体、発光素子、表示装置 |
JP5081010B2 (ja) * | 2007-03-26 | 2012-11-21 | 富士フイルム株式会社 | 有機電界発光素子 |
JP5435883B2 (ja) | 2007-03-28 | 2014-03-05 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
WO2008132085A1 (de) | 2007-04-26 | 2008-11-06 | Basf Se | Silane enthaltend phenothiazin-s-oxid oder phenothiazin-s,s-dioxid-gruppen und deren verwendung in oleds |
US8440826B2 (en) | 2007-06-22 | 2013-05-14 | Basf Se | Light emitting Cu (I) complexes |
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 |
US8221907B2 (en) | 2007-07-07 | 2012-07-17 | Idemitsu Kosan Co., Ltd. | Chrysene derivative and organic electroluminescent device using the same |
TW200909560A (en) | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Organic electroluminescence device and material for organic electroluminescence devcie |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
KR20100044200A (ko) | 2007-07-07 | 2010-04-29 | 이데미쓰 고산 가부시키가이샤 | 나프탈렌 유도체, 유기 el 소자용 재료 및 그것을 사용한 유기 el 소자 |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
WO2009008100A1 (ja) | 2007-07-10 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 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 |
KR20100065302A (ko) | 2007-07-27 | 2010-06-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무기 나노입자를 포함하는 전기 전도성 중합체의 수성 분산물 |
KR101630883B1 (ko) | 2007-08-08 | 2016-06-15 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
JP5438941B2 (ja) * | 2007-09-25 | 2014-03-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
JP2011500648A (ja) | 2007-10-17 | 2011-01-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 架橋カルベンリガンドを有する遷移金属錯体およびoledにおけるその使用 |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
EP2216313B1 (en) | 2007-11-15 | 2013-02-20 | Idemitsu Kosan Co., Ltd. | Benzochrysene derivative and organic electroluminescent device using the same |
US8759819B2 (en) | 2007-11-22 | 2014-06-24 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
KR101583097B1 (ko) | 2007-11-22 | 2016-01-07 | 이데미쓰 고산 가부시키가이샤 | 유기 el 소자 및 유기 el 재료 함유 용액 |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2009100991A1 (en) | 2008-02-12 | 2009-08-20 | Basf Se | Electroluminescent metal complexes with dibenzo[f,h]quinoxalines |
JP4531842B2 (ja) | 2008-04-24 | 2010-08-25 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4562805B2 (ja) | 2008-04-24 | 2010-10-13 | 富士フイルム株式会社 | 白金錯体 |
JP2009267171A (ja) | 2008-04-25 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009267244A (ja) | 2008-04-28 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
WO2010027583A1 (en) * | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
ATE503037T1 (de) | 2008-10-17 | 2011-04-15 | Atotech Deutschland Gmbh | Spannungsreduzierte ni-p/pd-stapel für waferoberfläche |
US8815415B2 (en) * | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
CN102449108B (zh) | 2009-04-06 | 2015-06-24 | 代表亚利桑那州立大学行事的亚利桑那董事会 | 四配位铂络合物的合成以及它们在发光器件中的应用 |
JP4598137B1 (ja) | 2009-07-31 | 2010-12-15 | 富士フイルム株式会社 | 有機電界発光素子の製造方法 |
JP2010185068A (ja) | 2009-08-31 | 2010-08-26 | Fujifilm Corp | 有機電界発光素子 |
JP4551480B1 (ja) | 2009-08-31 | 2010-09-29 | 富士フイルム株式会社 | 有機電界発光素子 |
JP5627896B2 (ja) | 2009-09-30 | 2014-11-19 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
JP5671248B2 (ja) | 2010-03-31 | 2015-02-18 | ユー・ディー・シー アイルランド リミテッド | 有機薄膜及び有機電界発光素子 |
JP5608404B2 (ja) | 2010-03-31 | 2014-10-15 | ユー・ディー・シー アイルランド リミテッド | 白金錯体、発光材料、有機電界発光素子、表示装置及び照明装置 |
TW201841932A (zh) * | 2011-02-23 | 2018-12-01 | 美商環球展覽公司 | 新穎四牙鉑錯合物 |
US9238668B2 (en) | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US9871214B2 (en) * | 2015-03-23 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2012
- 2012-08-17 US US13/588,968 patent/US9783564B2/en active Active
- 2012-09-26 EP EP12186152.0A patent/EP2574613B1/en active Active
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009266943A (ja) * | 2008-04-23 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009267170A (ja) * | 2008-04-25 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009267176A (ja) * | 2008-04-25 | 2009-11-12 | Fujifilm Corp | 有機電界発光素子 |
JP2009272339A (ja) * | 2008-04-30 | 2009-11-19 | Fujifilm Corp | 有機電界発光素子 |
JP6061595B2 (ja) * | 2011-09-30 | 2017-01-18 | ユニバーサル ディスプレイ コーポレイション | N−1に結合した捻じれたアリール基をもつ1又は2つのイミダゾール環を含むシクロメタル化四座配位Pt(II)錯体 |
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US20170240579A9 (en) | 2017-08-24 |
US9783564B2 (en) | 2017-10-10 |
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KR20130035919A (ko) | 2013-04-09 |
US10214551B2 (en) | 2019-02-26 |
KR101984891B1 (ko) | 2019-05-31 |
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EP2574613A1 (en) | 2013-04-03 |
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