JP2022535343A - 化合物、これを含むコーティング組成物およびこれを用いた有機発光素子 - Google Patents
化合物、これを含むコーティング組成物およびこれを用いた有機発光素子 Download PDFInfo
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- JP2022535343A JP2022535343A JP2021570210A JP2021570210A JP2022535343A JP 2022535343 A JP2022535343 A JP 2022535343A JP 2021570210 A JP2021570210 A JP 2021570210A JP 2021570210 A JP2021570210 A JP 2021570210A JP 2022535343 A JP2022535343 A JP 2022535343A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 260
- 239000008199 coating composition Substances 0.000 title claims abstract description 52
- 239000000126 substance Substances 0.000 claims abstract description 63
- 239000010410 layer Substances 0.000 claims description 147
- 125000004432 carbon atom Chemical group C* 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 239000012044 organic layer Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 36
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 2
- -1 1-methylpentyl Chemical group 0.000 description 72
- 238000002347 injection Methods 0.000 description 67
- 239000007924 injection Substances 0.000 description 67
- 230000015572 biosynthetic process Effects 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 230000005525 hole transport Effects 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 238000005406 washing Methods 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000006267 biphenyl group Chemical group 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 150000008040 ionic compounds Chemical class 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 4
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-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
- 125000005577 anthracene group Chemical group 0.000 description 4
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007639 printing Methods 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
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 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 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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Abstract
Description
本出願は、2019年7月17日付で韓国特許庁に提出された韓国特許出願第10-2019-0086310号、および2019年7月16日付で韓国特許庁に提出された韓国特許出願第10-2019-0085898号の出願日の利益を主張し、その内容はすべて本明細書に組み込まれる。
Lは、CR、N、SiR’、または
前記X1~X3は、互いに同一または異なり、それぞれ独立して、CHまたはNであり、
L1は、直接結合;または置換もしくは非置換のアリーレン基であり、
Y1およびY2は、互いに同一または異なり、それぞれ独立して、NR”、O、またはSであり、
R1、R2、R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;置換もしくは非置換のC2-60アルキニル; 置換もしくは非置換のC2-60アルケニル; 置換もしくは非置換のトリ(C1-60アルキル)シリル;または置換もしくは非置換のトリ(C6-60アリール)シリルであり、
aは、0~4の整数であり、aが2以上の場合、前記R1は、互いに同一または異なり、
bは、0~6の整数であり、bが2以上の場合、前記R2は、互いに同一または異なり、
前記X1~X3がCHの場合、Y1およびY2の少なくとも1つは、NR”またはSであり、
括弧[]内の構造は、互いに同一または異なる。
第1電極と、
第1電極に対向して備えられた第2電極と、
前記第1電極と前記第2電極との間に備えられた1層以上の有機物層と
を含む有機発光素子であって、
前記有機物層のうちの1層以上は、前述したコーティング組成物またはその硬化物を含む、有機発光素子を提供する。
Lの定義は、化学式1における定義と同じであり、
L11~L13は、互いに同一または異なり、それぞれ独立して、化学式1のL1の定義と同じであり、
Y11~Y13およびY21~Y23の定義は、化学式1におけるY1およびY2の定義と同じであり、
R11~R13およびR21~R23の定義は、化学式1におけるR1およびR2と同じであり、
a1~a3は、化学式1におけるaの定義と同じであり、
b1~b3は、化学式1におけるbの定義と同じである。
Lの定義は、化学式1における定義と同じであり、
L11~L13は、互いに同一または異なり、それぞれ独立して、化学式1のL1の定義と同じであり、
Y11~Y13およびY21~Y23の定義は、化学式1におけるY1およびY2の定義と同じであり、
R11~R13およびR21~R23の定義は、化学式1におけるR1およびR2と同じであり、
a1~a3は、化学式1におけるaの定義と同じであり、
b1~b3は、化学式1におけるbの定義と同じである。
Y31およびY32は、それぞれ独立して、N(R33)、O、またはSであり、
X1~X3は、それぞれ独立して、CHまたはNであり、
前記X1~X3がCHの場合、Y31およびY32の少なくとも1つは、N(R33)またはSであり、
R31、R32およびR33は、それぞれ独立して、水素;重水素;ハロゲン;シアノ;置換もしくは非置換のC1-60アルキル;置換もしくは非置換のC1-60アルコキシ;置換もしくは非置換のC2-60アルケニル;置換もしくは非置換のC2-60アルキニル;置換もしくは非置換のC3-60シクロアルキル;置換もしくは非置換のC6-60アリール;置換もしくは非置換のN、O、およびSからなる群より選択されるいずれか1つ以上のヘテロ原子を含むC2-60ヘテロアリール;置換もしくは非置換のトリ(C1-60アルキル)シリル;または置換もしくは非置換のトリ(C6-60アリール)シリルであり、
n1は、それぞれ独立して、1~3の整数であり、
n2は、それぞれ独立して、1~4の整数である。
X1~X3、Y31、Y32、R31、R32、n1およびn2は、化学式10で定義した通りである。
R1~R3は、化学式1のR1およびR2の定義と同じであり、
Xは、ハロゲン基である。
前記化合物とホスト物質を1:1~1:200の重量比で含む。
L20は、直接結合;または置換もしくは非置換のアリーレン基であり、
R100は、水素、重水素、ハロゲン基、ニトリル基、置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基であり、
r100は、0~8の整数であり、前記r100が2以上の場合、R100は、互いに同一または異なる。
前記正孔注入層、正孔輸送層、および発光層は、溶液工程により形成される。
HOMO(eV)=4.8+(Eonset-E1/2(Fc))
m/z [M+H]+ C27H32Cl2N+ 440.2
m/z [M+H]+ C50H58N3 + 700.5
m/z [M+H]+ C131H148Cl3N6 + 1910.1
m/z [M+H]+ C131H142B3N6 + 1832.16
m/z [M+H]+ C26H30Cl2N+ 426.2
m/z [M+H]+ C128H142Cl3N6 + 1868.1
m/z [M+H]+ C128H136B3N6 + 1790.3
m/z [M+H]+ C48H55N4 + 687.4
m/z [M+H]+ C129H145Cl3N7 + 1897.1
m/z [M+H]+ C129H139B3N7 + 1819.1
m/z [M+H]+ C16H19O2 + 243.2
m/z [M+H]+ C68H67O6 + 979.5
m/z [M+H]+ C68H58B3O6 + 1003.5
m/z [M+H]+ C80H88Cl6N3 + 1300.5
m/z [M+H]+ C134H166Cl3N6Si6 + 2132.1
m/z [M+H]+ C134H160B3N6Si6 + 2054.2
m/z [M+H]+ C79H88Cl6N3Si+ 1316.49
m/z [M+H]+ C133H166Cl3N6Si7 + 2148.1
m/z [M+H]+ C133H160B3N6Si7 + 2070.1
m/z [M+H]+ C38H22Br3Cl6 + 924.7
m/z [M+H]+ C158H178Cl3N6 + 2264.3
m/z [M+H]+ C158H172B3N6 + 2186.4
m/z [M+H]+ C24H22N3 + 352.2
m/z [M+H]+ C54H58N3 + 748.6
m/z [M+H]+ C135H148Cl3N6 + 1958.1
m/z [M+H]+ C135H142B3N6 + 1880.2
m/z [M+H]+ C24H22N3 + 352.2
m/z [M+H]+ C54H58N3 + 748.6
m/z [M+H]+ C135H148Cl3N6 + 1958.1
m/z [M+H]+ C135H142B3N6 + 1880.2
m/z [M+H]+ C24H22N3 + 352.2
m/z [M+H]+ C54H58N3 + 748.6
m/z [M+H]+ C135H148Cl3N6 + 1958.1
m/z [M+H]+ C135H142B3N6 + 1880.2
m/z [M+H]+ C21H19N6 + 355.2
m/z [M+H]+ C51H55N6 + 751.5
m/z [M+H]+ C132H145Cl3N9 + 1961.1
m/z [M+H]+ C132H139B3N9 + 1883.2
m/z [M+H]+ C16H19O2 + 243.2
m/z [M+H]+ C102H106N3O3 + 1420.8
m/z [M+H]+ C102H97B3N3O3 + 1444.8
m/z [M+H]+ C16H18ClO+ 260.1
m/z [M+H]+ C24H19O3 + 355.2
m/z [M+H]+ C75H70Cl3O6 + 1171.4
m/z [M+H]+ C75H64B3O6 + 1093.7
ITO(indium tin oxide)が500Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピル、アセトンの溶剤で超音波洗浄をし乾燥させた後、前記基板を5分間洗浄した後、グローブボックスに基板を輸送させた。
上記の過程で有機物の蒸着速度は0.4~0.7Å/sec を維持し、LiFは0.3Å/sec、アルミニウムは2Å/secの蒸着速度を維持し、蒸着時の真空度は2×10-7~5×10-8torrを維持した。
発光層のドーパントとして、化合物1の代わりに下記表1に記載の化合物(下記の化合物)を用いることを除き、前記実施例1と同様の方法で有機発光素子を製造した。
発光層のドーパントとして、化合物1の代わりに下記表1に記載の化合物(下記の化合物)を用いることを除き、前記実施例1と同様の方法で有機発光素子を製造した。
前記実施例および比較例で製造した有機発光素子に電流を印加した時、10mA/cm2の電流密度での駆動電圧、外部量子効率(external quantum efficiency、EQE)および寿命を測定した結果を、下記表1に示した。この時、外部量子効率(EQE)は、「(放出された光子の数)/(注入された電荷キャリアの数)*100」で求め、T90は、輝度が初期輝度(500nit)から90%に減少するのにかかる時間を意味する。
2・・・陽極
3・・・発光層
4・・・陰極
5・・・正孔注入層
6・・・正孔輸送層
7・・・電子注入および輸送層
Claims (21)
- 下記化学式1で表される化合物:
Lは、CR、N、SiR’、または
前記X1~X3は、互いに同一または異なり、それぞれ独立して、CHまたはNであり、
L1は、直接結合;または置換もしくは非置換のアリーレン基であり、
Y1およびY2は、互いに同一または異なり、それぞれ独立して、NR”、O、またはSであり、
R1、R2、R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;置換もしくは非置換のC2-60アルキニル; 置換もしくは非置換のC2-60アルケニル; 置換もしくは非置換のトリ(C1-60アルキル)シリル;または置換もしくは非置換のトリ(C6-60アリール)シリルであり、
aは、0~4の整数であり、aが2以上の場合、前記R1は、互いに同一または異なり、
bは、0~6の整数であり、bが2以上の場合、前記R2は、互いに同一または異なり、
但し、前記X1~X3がCHである場合には、Y1およびY2の少なくとも1つは、NR”またはSであり、
括弧[]内の構造は、互いに同一または異なる。 - 前記化学式1の括弧[]内の構造は、互いに同一である、請求項1に記載の化合物。
- 前記Lは、CR、N、またはSiR’である、請求項1に記載の化合物。
- 前記Lは、CR、N、またはSiR’であり、前記RおよびR’は、互いに同一または異なり、それぞれ独立して、水素;または炭素数1~10のアルキル基である、請求項1~3、5および6のいずれか一項に記載の化合物。
- 前記Y1およびY2は、NR”であり、前記R”は、置換もしくは非置換の炭素数6~20のアリール基;または置換もしくは非置換の炭素数2~20のヘテロアリール基ある、請求項1~7のいずれか一項に記載の化合物。
- 前記Y1およびY2は、NR”であり、前記R”は、アルキル基、シリル基、アミン基、アリール基、およびヘテロアリール基からなる群より選択される置換基で置換されたアリール基である、請求項1~7のいずれか一項に記載の化合物。
- 前記R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;重水素;炭素数1~10のアルキル基;炭素数1~10のアルキル基で置換されたシリル基;炭素数6~20のアリール基で置換されたアミン基;置換もしくは非置換の炭素数6~20のアリール基;置換もしくは非置換の炭素数2~20のヘテロアリール基であり、
前記アリール基およびヘテロアリール基は、炭素数1~10のアルキル基;炭素数1~10のアルキル基で置換されたシリル基;炭素数6~20のアリール基で置換されたアミン基;炭素数6~20のアリール基;および炭素数2~20のヘテロアリール基からなる群より選択される1以上の置換基で置換もしくは非置換である、請求項1~9のいずれか一項に記載の化合物。 - 前記化学式1で表される化合物は、下記化学式10で表される、請求項1に記載の化合物:
Y31およびY32は、それぞれ独立して、N(R33)、O、またはSであり、
X1~X3は、それぞれ独立して、CHまたはNであり、
前記X1~X3がCHの場合、Y31およびY32の少なくとも1つは、N(R33)またはSであり、
R31、R32およびR33は、それぞれ独立して、水素;重水素;ハロゲン;シアノ;置換もしくは非置換のC1-60アルキル;置換もしくは非置換のC1-60アルコキシ;置換もしくは非置換のC2-60アルケニル;置換もしくは非置換のC2-60アルキニル;置換もしくは非置換のC3-60シクロアルキル;置換もしくは非置換のC6-60アリール;置換もしくは非置換のN、O、およびSからなる群より選択されるいずれか1つ以上のヘテロ原子を含むC2-60ヘテロアリール;置換もしくは非置換のトリ(C1-60アルキル)シリル;または置換もしくは非置換のトリ(C6-60アリール)シリルであり、
n1は、それぞれ独立して、1~3の整数であり、
n2は、それぞれ独立して、1~4の整数である。 - 前記Y31およびY32は、それぞれ独立して、N(R33)である、請求項13に記載の化合物。
- 請求項1~14のいずれか1項に記載の化合物を含むコーティング組成物。
- 前記コーティング組成物は、有機発光素子用である、請求項15に記載のコーティング組成物。
- 第1電極と、
第1電極に対向して備えられた第2電極と、
前記第1電極と前記第2電極との間に備えられた1層以上の有機物層と
を含む有機発光素子であって、
前記有機物層のうちの1層以上は、請求項15に記載のコーティング組成物またはその硬化物を含む有機発光素子。 - 前記有機物層は、発光層を含み、前記発光層は、前記コーティング組成物またはその硬化物を含む、請求項17に記載の有機発光素子。
- 前記発光層は、青色発光層である、請求項18に記載の有機発光素子。
- 前記コーティング組成物は、ホスト物質をさらに含み、
前記化合物とホスト物質との重量比が1:1~1:200である、請求項17に記載の有機発光素子。 - 前記コーティング組成物は、ホスト物質をさらに含み、
前記ホスト物質は、下記化学式Aで表される、請求項17に記載の有機発光素子:
L20は、直接結合;または置換もしくは非置換のアリーレン基であり、
R100は、水素、重水素、ハロゲン基、ニトリル基、置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
r100は、0~8の整数であり、前記r100が2以上の場合、R100は、互いに同一または異なる。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021091644A (ja) * | 2019-12-12 | 2021-06-17 | 学校法人関西学院 | 多量体化合物 |
JP2022551399A (ja) * | 2020-05-14 | 2022-12-09 | 季華実験室 | ホウ素窒素化合物、有機電界発光組成物及びそれを含む有機電界発光素子 |
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CN113651838B (zh) * | 2021-02-04 | 2023-03-24 | 中国科学院长春应用化学研究所 | 一种含有多个硼-氧族原子杂化稠环单元的化合物及其制备方法和应用 |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017535540A (ja) * | 2014-10-29 | 2017-11-30 | ヒソン・マテリアル・リミテッドHeesung Material Ltd. | 含窒素多環式化合物及びこれを用いた有機発光素子 |
WO2019035268A1 (ja) * | 2017-08-17 | 2019-02-21 | 学校法人関西学院 | 有機電界発光素子 |
CN109411633A (zh) * | 2018-08-31 | 2019-03-01 | 昆山国显光电有限公司 | 一种有机电致发光器件及其制备方法和显示装置 |
JP2019096823A (ja) * | 2017-11-27 | 2019-06-20 | Jnc株式会社 | 有機電界発光素子 |
CN110790782A (zh) * | 2019-11-11 | 2020-02-14 | 北京大学深圳研究生院 | 一种深蓝色有机发光材料及其制备方法与应用 |
JP2021501126A (ja) * | 2017-09-15 | 2021-01-14 | エルティー・マテリアルズ・カンパニー・リミテッドLT Materials Co., Ltd. | ヘテロ環化合物およびこれを含む有機発光素子 |
US20210193927A1 (en) * | 2019-12-18 | 2021-06-24 | Samsung Display Co., Ltd. | Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic device including organic light-emitting device |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7023452B2 (ja) * | 2016-06-17 | 2022-02-22 | 株式会社Kyulux | 発光材料、有機発光素子および化合物 |
US20190378991A1 (en) * | 2016-11-23 | 2019-12-12 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture, composition, and organic electronic component |
JP7213181B2 (ja) * | 2017-06-30 | 2023-01-26 | 住友化学株式会社 | 発光素子及びその製造に有用な高分子化合物 |
KR102000547B1 (ko) | 2017-08-16 | 2019-07-16 | 주식회사 이엘에프 | 미세 전류를 이용하는 마스크 팩 |
KR20190086310A (ko) | 2018-01-12 | 2019-07-22 | 주식회사 케이티 | LTE URLLC에서 legacy 데이터 채널 다중화 방법 및 장치 |
-
2020
- 2020-07-16 WO PCT/KR2020/009377 patent/WO2021010767A1/ko unknown
- 2020-07-16 CN CN202080034285.4A patent/CN113825761B/zh active Active
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- 2020-07-16 TW TW109124094A patent/TWI777192B/zh active
- 2020-07-16 JP JP2021570210A patent/JP7286220B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017535540A (ja) * | 2014-10-29 | 2017-11-30 | ヒソン・マテリアル・リミテッドHeesung Material Ltd. | 含窒素多環式化合物及びこれを用いた有機発光素子 |
WO2019035268A1 (ja) * | 2017-08-17 | 2019-02-21 | 学校法人関西学院 | 有機電界発光素子 |
JP2021501126A (ja) * | 2017-09-15 | 2021-01-14 | エルティー・マテリアルズ・カンパニー・リミテッドLT Materials Co., Ltd. | ヘテロ環化合物およびこれを含む有機発光素子 |
JP2019096823A (ja) * | 2017-11-27 | 2019-06-20 | Jnc株式会社 | 有機電界発光素子 |
CN109411633A (zh) * | 2018-08-31 | 2019-03-01 | 昆山国显光电有限公司 | 一种有机电致发光器件及其制备方法和显示装置 |
CN110790782A (zh) * | 2019-11-11 | 2020-02-14 | 北京大学深圳研究生院 | 一种深蓝色有机发光材料及其制备方法与应用 |
US20210193927A1 (en) * | 2019-12-18 | 2021-06-24 | Samsung Display Co., Ltd. | Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic device including organic light-emitting device |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021091644A (ja) * | 2019-12-12 | 2021-06-17 | 学校法人関西学院 | 多量体化合物 |
JP2022551399A (ja) * | 2020-05-14 | 2022-12-09 | 季華実験室 | ホウ素窒素化合物、有機電界発光組成物及びそれを含む有機電界発光素子 |
JP7461466B2 (ja) | 2020-05-14 | 2024-04-03 | 季華実験室 | ホウ素窒素化合物、有機電界発光組成物及びそれを含む有機電界発光素子 |
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