WO2022225198A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant - Google Patents
Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant Download PDFInfo
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- WO2022225198A1 WO2022225198A1 PCT/KR2022/003947 KR2022003947W WO2022225198A1 WO 2022225198 A1 WO2022225198 A1 WO 2022225198A1 KR 2022003947 W KR2022003947 W KR 2022003947W WO 2022225198 A1 WO2022225198 A1 WO 2022225198A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 67
- 125000001931 aliphatic group Chemical group 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 230000005525 hole transport Effects 0.000 claims description 38
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 37
- 229910052698 phosphorus Inorganic materials 0.000 claims description 35
- 229910052710 silicon Inorganic materials 0.000 claims description 35
- 239000011368 organic material Substances 0.000 claims description 28
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 27
- 125000004104 aryloxy group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000005567 fluorenylene group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 12
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 12
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical class P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 12
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000006757 (C2-C30) heterocyclic group Chemical group 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000002096 quantum dot Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 6
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- 238000003786 synthesis reaction Methods 0.000 description 55
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000005647 linker group Chemical group 0.000 description 11
- -1 such as N Inorganic materials 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000000470 constituent Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 150000003413 spiro compounds Chemical class 0.000 description 7
- HAPOJKSPCGLOOD-UHFFFAOYSA-N Benzo[b]fluorene Chemical compound C1=CC=C2C=C3CC4=CC=CC=C4C3=CC2=C1 HAPOJKSPCGLOOD-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 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 4
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 230000000903 blocking effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 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
- 239000000758 substrate Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- DIXBHJUDXSXBMK-UHFFFAOYSA-N 11,11-diphenylbenzo[b]fluorene Chemical compound C1=CC=CC(=C1)C1(C2=CC3=CC=CC=C3C=C2C2=CC=CC=C12)C1=CC=CC=C1 DIXBHJUDXSXBMK-UHFFFAOYSA-N 0.000 description 3
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- QFPVHUJPACOOEB-UHFFFAOYSA-N 9-naphthalen-2-yl-9-phenylfluorene Chemical compound c1ccc(cc1)C1(c2ccccc2-c2ccccc12)c1ccc2ccccc2c1 QFPVHUJPACOOEB-UHFFFAOYSA-N 0.000 description 3
- GKPVPZKPIQGINT-UHFFFAOYSA-N C1=CC2=C(C=C1)C1(C3=CC=CC=C3C3=C1C=C1C=CC=CC1=C3)C1=C2C=CC=C1 Chemical compound C1=CC2=C(C=C1)C1(C3=CC=CC=C3C3=C1C=C1C=CC=CC1=C3)C1=C2C=CC=C1 GKPVPZKPIQGINT-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- YUFRAQHYKKPYLH-UHFFFAOYSA-N benzo[f]quinoxaline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=N1 YUFRAQHYKKPYLH-UHFFFAOYSA-N 0.000 description 3
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [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
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- 125000005580 triphenylene group Chemical group 0.000 description 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- FFMJAFCTEHLDQG-UHFFFAOYSA-N 1-phenyl-11H-benzo[a]carbazole Chemical compound C1(=CC=CC=C1)C1=CC=CC=2C1=C1NC3=CC=CC=C3C1=CC2 FFMJAFCTEHLDQG-UHFFFAOYSA-N 0.000 description 1
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- LAVLDGSVWFEKJG-UHFFFAOYSA-N 10-phenylphenoxazine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2N1C1=CC=CC=C1 LAVLDGSVWFEKJG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
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- ALIHHRJMNTXXJT-UHFFFAOYSA-N 2-phenyl-1h-benzo[g]indole Chemical compound N1C(C2=CC=CC=C2C=C2)=C2C=C1C1=CC=CC=C1 ALIHHRJMNTXXJT-UHFFFAOYSA-N 0.000 description 1
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- QKEBGAUJUHZNNU-UHFFFAOYSA-N 9h-pyrrolo[2,3-f]quinoxaline Chemical compound N1=CC=NC2=C(NC=C3)C3=CC=C21 QKEBGAUJUHZNNU-UHFFFAOYSA-N 0.000 description 1
- MAOJTGOOFNUUJL-UHFFFAOYSA-N C1=CC=CC2=C3OC4=CC=C(C=CC=C5)C5=C4OC3=CC=C21 Chemical compound C1=CC=CC2=C3OC4=CC=C(C=CC=C5)C5=C4OC3=CC=C21 MAOJTGOOFNUUJL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- HYWNGEYOXQESBM-UHFFFAOYSA-N [1]benzofuro[2,3-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=N1 HYWNGEYOXQESBM-UHFFFAOYSA-N 0.000 description 1
- HDJHJMOTVCXUGP-UHFFFAOYSA-N [1]benzofuro[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3OC2=N1 HDJHJMOTVCXUGP-UHFFFAOYSA-N 0.000 description 1
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 1
- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
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- XEMRLVBSKVCUDL-UHFFFAOYSA-N benzo[g]quinoxaline Chemical compound N1=CC=NC2=CC3=CC=CC=C3C=C21 XEMRLVBSKVCUDL-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
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- 238000010295 mobile communication Methods 0.000 description 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- YTIFDAAZLZVHIX-UHFFFAOYSA-N naphtho[1,2-g][1]benzofuran Chemical compound C1=CC=C2C3=CC=C4C=COC4=C3C=CC2=C1 YTIFDAAZLZVHIX-UHFFFAOYSA-N 0.000 description 1
- FYSWUOGCANSBCW-UHFFFAOYSA-N naphtho[1,2-g][1]benzothiole Chemical compound C1=CC=C2C3=CC=C4C=CSC4=C3C=CC2=C1 FYSWUOGCANSBCW-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- MCBJUXFCNBVPNF-UHFFFAOYSA-N phenanthro[9,10-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 MCBJUXFCNBVPNF-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
La présente invention concerne : un composé représenté par la formule chimique 1 ; un élément électrique organique comprenant une première électrode, une seconde électrode et une couche organique entre la première électrode et la seconde électrode ; et un dispositif électronique comprenant l'élément électrique organique. Le composé représenté par la formule chimique 1 peut être incorporé dans la couche organique de l'élément électrique organique, ce qui permet de réduire la tension de commande de ce dernier, d'améliorer son efficacité lumineuse et d'augmenter sa durée de vie.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202280029789.6A CN117203184A (zh) | 2021-04-23 | 2022-03-22 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20210052990 | 2021-04-23 | ||
| KR10-2021-0052990 | 2021-04-23 | ||
| KR10-2021-0057264 | 2021-05-03 | ||
| KR1020210057264A KR20220146987A (ko) | 2021-04-23 | 2021-05-03 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
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| Publication Number | Publication Date |
|---|---|
| WO2022225198A1 true WO2022225198A1 (fr) | 2022-10-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2022/003947 WO2022225198A1 (fr) | 2021-04-23 | 2022-03-22 | Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant |
Country Status (2)
| Country | Link |
|---|---|
| KR (2) | KR102292406B1 (fr) |
| WO (1) | WO2022225198A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117377650A (zh) * | 2021-05-28 | 2024-01-09 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
| WO2023140285A1 (fr) * | 2022-01-21 | 2023-07-27 | 出光興産株式会社 | Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique |
| CN114507222A (zh) * | 2022-03-03 | 2022-05-17 | 上海钥熠电子科技有限公司 | 一种胺类化合物及其在有机电致发光器件中的应用 |
| CN115010609A (zh) * | 2022-06-02 | 2022-09-06 | 南京高光半导体材料有限公司 | 一种含有二苯基芴结构的胺基化合物及有机电致发光器件 |
| WO2024071062A1 (fr) * | 2022-09-29 | 2024-04-04 | 出光興産株式会社 | Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160113783A (ko) * | 2015-03-23 | 2016-10-04 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| KR20170100709A (ko) * | 2016-02-25 | 2017-09-05 | 삼성디스플레이 주식회사 | 아민 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| KR102041137B1 (ko) * | 2019-04-02 | 2019-11-07 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
| CN110437081A (zh) * | 2019-07-15 | 2019-11-12 | 陕西莱特光电材料股份有限公司 | 含三环庚烷的有机化合物及其制备方法和包含该化合物的有机电致发光器件 |
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| KR20210036097A (ko) * | 2019-09-25 | 2021-04-02 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
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| KR20200127628A (ko) * | 2019-05-03 | 2020-11-11 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치 |
| KR20210067946A (ko) * | 2019-11-29 | 2021-06-08 | 주식회사 엘지화학 | 유기 발광 소자 |
-
2021
- 2021-05-03 KR KR1020210057313A patent/KR102292406B1/ko active IP Right Grant
- 2021-10-06 KR KR1020210132092A patent/KR102380419B1/ko active IP Right Grant
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2022
- 2022-03-22 WO PCT/KR2022/003947 patent/WO2022225198A1/fr active Application Filing
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160113783A (ko) * | 2015-03-23 | 2016-10-04 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| KR20170100709A (ko) * | 2016-02-25 | 2017-09-05 | 삼성디스플레이 주식회사 | 아민 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| CN111606813A (zh) * | 2019-02-25 | 2020-09-01 | 北京鼎材科技有限公司 | 化合物、包含其的有机电子发光器件及其应用 |
| CN111662190A (zh) * | 2019-03-08 | 2020-09-15 | 江苏三月光电科技有限公司 | 一种含芘或氮杂芘的有机化合物及其应用 |
| KR102041137B1 (ko) * | 2019-04-02 | 2019-11-07 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
| CN110437081A (zh) * | 2019-07-15 | 2019-11-12 | 陕西莱特光电材料股份有限公司 | 含三环庚烷的有机化合物及其制备方法和包含该化合物的有机电致发光器件 |
| KR20210033119A (ko) * | 2019-09-17 | 2021-03-26 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20210036097A (ko) * | 2019-09-25 | 2021-04-02 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
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| KR102292406B1 (ko) | 2021-08-23 |
| KR102380419B1 (ko) | 2022-03-30 |
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