JP2022104953A - 有機エレクトロルミネセンス材料及びデバイス - Google Patents
有機エレクトロルミネセンス材料及びデバイス Download PDFInfo
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- JP2022104953A JP2022104953A JP2022055034A JP2022055034A JP2022104953A JP 2022104953 A JP2022104953 A JP 2022104953A JP 2022055034 A JP2022055034 A JP 2022055034A JP 2022055034 A JP2022055034 A JP 2022055034A JP 2022104953 A JP2022104953 A JP 2022104953A
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- 239000000463 material Substances 0.000 title claims abstract description 91
- 239000003446 ligand Substances 0.000 claims abstract description 65
- 125000003118 aryl group Chemical group 0.000 claims abstract description 48
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 69
- -1 dehydrogen Chemical class 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 238000006467 substitution reaction Methods 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 150000002527 isonitriles Chemical class 0.000 claims description 19
- 150000002825 nitriles Chemical class 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 125000006193 alkinyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 239000002019 doping agent Substances 0.000 description 22
- 230000032258 transport Effects 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 11
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000005580 triphenylene group Chemical group 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
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- 239000002244 precipitate Substances 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229910052754 neon Inorganic materials 0.000 description 4
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 3
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
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- QZLAKPGRUFFNRD-UHFFFAOYSA-N [1]benzoselenolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3[se]C2=C1 QZLAKPGRUFFNRD-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 3
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 3
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 3
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- 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 3
- 230000007246 mechanism Effects 0.000 description 3
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
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- 239000011241 protective layer Substances 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
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- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
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- RIHRJZTTXVLKRU-UHFFFAOYSA-N 4-phenylbenzo[g]quinazoline Chemical compound C1(=CC=CC=C1)C1=NC=NC2=CC3=C(C=C12)C=CC=C3 RIHRJZTTXVLKRU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
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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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- C09B57/00—Other synthetic dyes of known constitution
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F15/0033—Iridium compounds
- C07F15/004—Iridium compounds without a metal-carbon linkage
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
Description
本願は、参照によりその内容全体を本明細書に援用する、2016年11月9日出願の米国仮特許出願第62/419,620号に対する優先権を主張する。
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
2つの隣接するR1は、結合して環を形成又は縮合してもよく、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。
本発明の化合物
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
2つの隣接するR1は、結合して環を形成又は縮合してもよく、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。
次式に基づくLA1~LA178
Xは、BR’、NR’、PR’、O、S、Se、C=O、S=O、SO2、CR’R’’、SiR’R’’、及びGeR’R’’からなる群から選択され、
R’及びR’’は、縮合又は結合して環を形成していてもよく、
各Ra、Rb、Rc、及びRdは、モノ置換から可能な最大置換数、又は無置換を表すことができ、
R’、R’’、Ra、Rb、Rc、及びRdは、それぞれ独立して、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
Ra、Rb、Rc、及びRdの任意の2つの隣接する置換基は、縮合又は結合して、環又は多座配位子を形成していてもよい。
他の材料との組合せ
電荷輸送層は、伝導性ドーパントでドープされ、電荷キャリアの密度を大きく変え、それによりその伝導性を変えることとなる。伝導性は、マトリックス材料中の電荷キャリアを生成することで、又はドーパントのタイプに応じて増加され、半導体のフェルミ準位における変化も達成することができる。正孔輸送層は、p型伝導性ドーパントでドープされることができ、n型伝導性ドーパントは、電子輸送層中に用いられる。
EP01617493、EP01968131、EP2020694、EP2684932、US20050139810、US20070160905、US20090167167、US2010288362、WO06081780、WO2009003455、WO2009008277、WO2009011327、WO2014009310、US2007252140、US2015060804、US2012146012
式中、kは1から20までの整数であり;X101からX108はC(CHを含む)又はNであり;Z101はNAr1、O、又はSであり;Ar1は、上記で定義したものと同じ基を有する。
CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07-073529、JP2005112765、JP2007091719、JP2008021687、JP2014-009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018
ホスト:
Z101及びZ102はNR101、O、又はSである。
EP2034538、EP2034538A、EP2757608、JP2007254297、KR20100079458、KR20120088644、KR20120129733、KR20130115564、TW201329200、US20030175553、US20050238919、US20060280965、US20090017330、US20090030202、US20090167162、US20090302743、US20090309488、US20100012931、US20100084966、US20100187984、US2010187984、US2012075273、US2012126221、US2013009543、US2013105787、US2013175519、US2014001446、US20140183503、US20140225088、US2014034914、US7154114、WO2001039234、WO2004093207、WO2005014551、WO2005089025、WO2006072002、WO2006114966、WO2007063754、WO2008056746、WO2009003898、WO2009021126、WO2009063833、WO2009066778、WO2009066779、WO2009086028、WO2010056066、WO2010107244、WO2011081423、WO2011081431、WO2011086863、WO2012128298、WO2012133644、WO2012133649、WO2013024872、WO2013035275、WO2013081315、WO2013191404、WO2014142472
CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601、US20130146848、US2013033172、US2013165653、US2013181190、US2013334521、US20140246656、US2014103305、US6303238、US6413656、US6653654、US6670645、US6687266、US6835469、US6921915、US7279704、US7332232、US7378162、US7534505、US7675228、US7728137、US7740957、US7759489、US7951947、US8067099、US8592586、US8871361、WO06081973、WO06121811、WO07018067、WO07108362、WO07115970、WO07115981、WO08035571、WO2002015645、WO2003040257、WO2005019373、WO2006056418、WO2008054584、WO2008078800、WO2008096609、WO2008101842、WO2009000673、WO2009050281、WO2009100991、WO2010028151、WO2010054731、WO2010086089、WO2010118029、WO2011044988、WO2011051404、WO2011107491、WO2012020327、WO2012163471、WO2013094620、WO2013107487、WO2013174471、WO2014007565、WO2014008982、WO2014023377、WO2014024131、WO2014031977、WO2014038456、WO2014112450
ETL:
実験
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
170 バリア層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (14)
- 式Iで表される配位子LAを含むことを特徴とする化合物。
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
2つの隣接するR1は、結合して環を形成又は縮合してもよく、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。) - Mが、Ir、Rh、Re、Ru、Os、Pt、Au、及びCuからなる群から選択される請求項1に記載の化合物。
- 前記少なくとも1つのR1が、メチル、エチル、プロピル、1-メチルエチル、ブチル、1-メチルプロピル、2-メチルプロピル、ペンチル、1-メチルブチル、2-メチルブチル、3-メチルブチル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、2,2-ジメチルプロピル、シクロペンチル、シクロヘキシル、及びこれらの組合せからなる群から選択される請求項1に記載の化合物。
- 前記化合物が、式M(LA)n(LB)m-nで表され、
式中、Mは、Ir又はPtであり、LBは、二座配位子であり、
MがIrのとき、mは3、nは1、2、又は3であり、
MがPtのとき、mは2、nは1又は2である請求項1に記載の化合物。 - LBが、下記からなる群から選択される請求項8に記載の化合物。
Xは、BR’、NR’、PR’、O、S、Se、C=O、S=O、SO2、CR’R’’、SiR’R’’、及びGeR’R’’からなる群から選択され、
R’及びR’’は、縮合又は結合して環を形成していてもよく、
各Ra、Rb、Rc、及びRdは、モノ置換から可能な最大置換数、又は無置換を表すことができ、
R’、R’’、Ra、Rb、Rc、及びRdは、それぞれ独立して、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
Ra、Rb、Rc、及びRdの任意の2つの隣接する置換基は、縮合又は結合して、環又は多座配位子を形成していてもよい。) - 式Iで表される配位子LAを含むことを特徴とする有機発光デバイス(OLED)に使用するための材料。
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。) - アノードと、カソードと、前記アノードと前記カソードとの間に配置される有機層とを含む有機発光デバイス(OLED)であって、前記有機層が、式Iで表される配位子LAを含む化合物を含むことを特徴とするOLED。
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。) - 有機発光デバイス(OLED)を含む消費者製品であって、前記有機発光デバイス(OLED)が、アノードと、カソードと、前記アノードと前記カソードとの間に配置される有機層とを含み、前記有機層が、式Iで表される配位子LAを含む化合物を含むことを特徴とする消費者製品。
Rは、環Bに縮合しており、式IIで表され、
環Dは、環Cと縮合しており、
環Dは、5員又は6員の炭素環又はヘテロ芳香族環であり、
R1は、モノ置換から可能な最大置換数を表し、
R2、R3、及びR4は、モノ置換から可能な最大置換数、又は無置換を表し、
X1、X2、X3、X4、X5、X6、X7、及びX8は、それぞれ独立して炭素又は窒素であり、
少なくとも2つの隣接するX1、X2、X3、及びX4が、炭素であり、環Cと縮合し、
少なくとも2つの隣接するX5、X6、X7、及びX8が、炭素であり、環Dと縮合し、
R2、R3、及びR4は、それぞれ独立して、水素、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
R2、R3、及びR4の2つの隣接する置換基は、結合して環を形成せず、
各R1は、独立して、重水素、ハロゲン、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、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、
少なくとも1つのR1は、アルキル、シクロアルキル、部分的にフッ素化されたそれらのバリアント、部分的又は完全に重水素化されたそれらのバリアント、及びこれらの組合せからなる群から選択され、
前記少なくとも1つのR1のそれぞれにおいて、Fが結合しているCは、前記芳香環から少なくとも1つの炭素原子分だけ離れており、
LAは、金属Mに配位しており、
LAは、他の配位子と結合して、三座、四座、五座、又は六座配位子を含んでいてもよく、
Mは、他の配位子に配位していてもよい。)
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CN108059645A (zh) | 2018-05-22 |
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CN117903215A (zh) | 2024-04-19 |
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