WO2019231210A1 - Heterocyclic compound and organic light emitting diode comprising same - Google Patents
Heterocyclic compound and organic light emitting diode comprising same Download PDFInfo
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- WO2019231210A1 WO2019231210A1 PCT/KR2019/006379 KR2019006379W WO2019231210A1 WO 2019231210 A1 WO2019231210 A1 WO 2019231210A1 KR 2019006379 W KR2019006379 W KR 2019006379W WO 2019231210 A1 WO2019231210 A1 WO 2019231210A1
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- same
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 239000011368 organic material Substances 0.000 claims description 31
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 20
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002560 nitrile group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 114
- 239000012044 organic layer Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- -1 2-ethylbutyloxy group Chemical group 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 125000006267 biphenyl group Chemical group 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 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 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000001624 naphthyl group Chemical group 0.000 description 15
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 125000005580 triphenylene group Chemical group 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 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 5
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 229940126543 compound 14 Drugs 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 description 4
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000005581 pyrene group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical group N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
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- 239000003599 detergent Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 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 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- TYOGIUGNZOBBHE-UHFFFAOYSA-N (2-chloro-3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1Cl TYOGIUGNZOBBHE-UHFFFAOYSA-N 0.000 description 1
- UCAKTFSAEMHJJE-UHFFFAOYSA-N (3-chloro-2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1O UCAKTFSAEMHJJE-UHFFFAOYSA-N 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006607 3,3-dimethylbutyloxy group Chemical group 0.000 description 1
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- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- MWIZGXJYCNZVDW-UHFFFAOYSA-N phenanthren-2-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3C=CC2=C1 MWIZGXJYCNZVDW-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- the present specification provides a heterocyclic compound and an organic light emitting device including the same.
- X1 to X3 are the same as or different from each other, and each independently N or CH
- At least one of X1 to X3 is N,
- R1 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxy group , Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted Heteroaryl group,
- Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
- L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
- Y is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Z is substituted or Unsubstituted aryl group,
- a is an integer from 0 to 5
- R1 is the same as or different from each other.
- the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound. .
- the heterocyclic compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.
- FIG. 1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
- FIG. 2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
- the present specification provides a heterocyclic compound represented by Chemical Formula 1.
- substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
- substituted or unsubstituted is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
- a substituent to which two or more substituents are linked may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
- the halogen group may be fluorine, chlorine, bromine or iodine.
- the alkoxy group may be linear, branched or cyclic.
- carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferable that it is C1-C20. More specifically, it is preferable that it is C1-C10.
- the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.
- Specific examples include vinyl groups; 1-propenyl group; Isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; Allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl group; 2, 2-bis (diphenyl- 1-yl) vinyl- 1-yl group; Stilbenyl group; Styrenyl group and the like, but is not limited thereto.
- the alkynyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.
- the phosphine oxide group is specifically a diphenylphosphine oxide group; And dinaphthylphosphine oxide groups, but are not limited thereto.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
- Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
- the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
- the present invention is not limited thereto.
- the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
- the aryl group is a monocyclic aryl group
- carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
- the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
- the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
- the aryl group in the aryloxy group is the same as the example of the aryl group described above.
- the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
- heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
- arylene group is the same as the definition of an aryl group except that it is divalent.
- heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.
- Formula 1 is represented by the following formula 1-1.
- R2 and R ' are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted A substituted aryloxy group or a substituted or unsubstituted heteroaryl group,
- b and m are integers from 0 to 5
- n is an integer from 0 to 1
- R2 is the same as or different from each other
- the R's are the same as or different from each other.
- Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
- R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group or substituted or unsubstituted heteroaryl group,
- b, d and f are each an integer of 0 to 5
- c and e are each an integer of 0 to 4,
- R2 is the same as or different from each other
- R3 is the same as or different from each other
- R4 is the same as or different from each other
- R5 is the same as or different from each other
- R6 is the same as or different from each other.
- Chemical Formula 1 is represented by any one of the following Chemical Formulas 5 to 7.
- X1 is N
- X2 and X3 are CH.
- X2 is N
- X1 and X3 are CH.
- X3 is N, and X1 and X2 are CH.
- X1 and X2 are N, and X3 is CH.
- X1 and X3 are N, and X2 is CH.
- X2 and X3 are N, and X2 is CH.
- X1 to X3 is N.
- the R1 to R6 is hydrogen.
- Z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- Z is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
- Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
- Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group containing any one or more of N, O, and S having 3 to 30 carbon atoms.
- Y is an alkyl group; Silyl groups; Phosphine oxide groups; Aryl group; Or a heteroaryl group,
- Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms,
- Y is a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group; Methyl group; Or silyl group,
- Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Monocyclic aryl groups having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms,
- the monocyclic aryl group having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl groups having 3 to 30 carbon atoms or polycyclic heteroaryl groups having 3 to 30 carbon atoms are deuterium, nitrile, halogen, aryl substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted carbon atoms 6 A silaryl group substituted with an aryl group of 30 to 30, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group including any one or more of N, O or S having 3 to 30 carbon atoms substituted or unsubstituted, or Substituted or unsubstituted with an phosphine oxide group unsubstituted or substituted with an alkyl or aryl group.
- Y is a phenyl group unsubstituted or substituted with a nitrile group, triphenylmethyl group, naphthyl group, phenylnaphthyl group, triphenylsilyl group, or trimethylsilyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Terphenyl group; Triphenylene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; A benzopuropyrimidine group unsubstituted or substituted with a phenyl group; A benzothienopyrimidine group unsubstituted or substituted with a phenyl group; Phosphine oxide groups substituted with phenyl groups; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubsti
- Y may be any one selected from the following substituents.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms to be.
- Ar1 and Ar2 are the same as each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
- Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
- Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
- Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polycyclic group having 6 to 30 carbon atoms.
- Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
- Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
- Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
- Ar1 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
- Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
- L is a direct bond, or a substituted or unsubstituted arylene group.
- L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- L is a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- L is a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.
- L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, substituted Or an unsubstituted divalent quarterphenyl group, a substituted or unsubstituted divalent fluorene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent triphenylene group Or a substituted or unsubstituted divalent phenanthrene group.
- L is a phenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A substituted or unsubstituted bivalent biphenyl group, a divalent terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent quarterphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A divalent fluorene group unsubstituted or substituted with a divalent anthracene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group unsubstituted or
- L is a phenylene group, naphthylene group, divalent biphenyl group, divalent terphenyl group, divalent quarterphenyl group, divalent fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms Group, a bivalent anthracene group, a bivalent pyrene group, a bivalent triphenylene group, or a bivalent phenanthrene group.
- L is a direct bond
- L is a phenylene group.
- L is a divalent naphthyl group.
- heterocyclic compound of Formula 1 may be represented by the following structural formula.
- the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers may include the aforementioned heterocyclic compound.
- the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
- FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
- the first electrode 2 the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, and the electron injection layer
- the structure of the organic light emitting device in which 10) and the second electrode 4 are sequentially stacked is illustrated.
- the compound of the present invention may be included in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and preferably may be included in a light emitting layer.
- 1 and 2 illustrate an organic light emitting device and are not limited thereto.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
- the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 50:50.
- the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 60:40.
- the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 80:20.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host.
- the organic material layer may include a light emitting layer, and the light emitting layer may include an additional host.
- the organic material layer may include a light emitting layer, and the light emitting layer may include an organic compound as an additional host.
- the organic material layer includes a light emitting layer, and the light emitting layer may include a carbazole derivative as an additional host.
- the organic material layer may include a light emitting layer, and the light emitting layer may include a bicarbazole compound as an additional host.
- the organic material layer may include a light emitting layer, and the light emitting layer may include a compound of Formula X as an additional host.
- Ax and Ay are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
- Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or Unsubstituted heteroaryl group,
- x and y are each an integer of 0 to 7,
- Ax and Ay are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms.
- Ax and Ay are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a fluorene group, or a pyrene group.
- Ax and Ay are the same as or different from each other, and are each independently a phenyl group or a biphenyl group.
- Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.
- Rx and Ry are hydrogen.
- the organic material layer may include a light emitting layer, and the light emitting layer may include an additional dopant.
- the organic material layer may include a light emitting layer, and the light emitting layer may include a fluorescent dopant.
- the organic material layer may include a light emitting layer, and the light emitting layer may include a phosphorescent dopant.
- the organic material layer may include a light emitting layer, and the light emitting layer may include an iridium-based dopant.
- the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the heterocyclic compound. have.
- the organic material layer may include an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer may include the heterocyclic compound. have.
- the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
- the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
- 2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 187 mmol) and (2-chloro-3-fluorophenyl) boronic acid (48.9 g, 280 mmol) in a nitrogen atmosphere was added to 400 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto.
- intermediate 4A (18.9 g, 32 mmol), bis (pinacolato) diboron (9.0 g, 35 mmol) and potassium acetate (6.3 g, 65 mmol) are mixed, added to 200 ml of dioxane and heated with stirring It was.
- bis (dibenzylideneacetone) palladium (6 g, 1.0 mmol)
- tricyclohexylphosphine 0.6 g, 1.9 mmol
- intermediate 2A 10 g, 20 mmol
- [1,1'-biphenyl] -4-ylboronic acid 8.0 g, 40 mmol
- the mixture was sufficiently stirred, and then stirred thoroughly. Input.
- the temperature was lowered to room temperature and filtered.
- the filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to give compound 1 (9.5 g, 77%).
- Compound 2 (9.5 g, 54%) was synthesized in the same manner as in the synthesis of Compound 1, except that the compound was used instead of [1,1'-biphenyl] -4-ylboronic acid.
- Compound 3 (10.6 g, 83%) was synthesized in the same manner as in the synthesis of Compound 1, except that phenanthrene-2-ylboronic acid was used instead of [1,1'-biphenyl] -4-ylboronic acid.
- Compound 7 (6.6 g, 55%) was synthesized in the same manner as in the synthesis of Compound 6, except that biphenyl-3-ylboronic acid was used instead of phenylboronic acid.
- intermediate 4A 10 g, 17 mmol
- phenylboronic acid 2.2 g, 19 mmol
- intermediate 4A was added to 100 ml of dioxane and stirred and refluxed.
- potassium phosphate 10.9g, 52mmol
- the temperature was lowered to room temperature and filtered.
- the filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 11 (7.4 g, 64%).
- Compound 12 (6.8 g, 57%) was synthesized in the same manner as in the synthesis of Compound 11, except that [1,1'-biphenyl] -4-ylboronic acid was used instead of phenylboronic acid.
- Compound 13 (8.1 g, 70%) was synthesized in the same manner as in the synthesis of Compound 11, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.
- the glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. was used as a detergent
- distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- the hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 kPa on the prepared ITO transparent electrode.
- a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film.
- ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer
- the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW.
- Aluminum was deposited to a thickness of 1000 ⁇ on the electron injection layer to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
- the aluminum was maintained at the deposition rate of 2 ⁇ / sec
- the vacuum during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr It was.
- An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.
- An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.
- the compounds of CE1 to CE3 in Table 1 are as follows.
- the organic light emitting diode was measured voltage and efficiency at a current density of 10mA / cm 2 , the lifetime was measured at a current density of 50mA / cm 2 and the results are shown in Table 1 below.
- LT95 means a time of 95% of the initial luminance.
- the compounds of the present invention showed lower voltage, higher efficiency and longer life compared to CE1 without the dibenzofuran core,
- N-containing monocyclic ring such as CE2
- the N-containing monocyclic ring such as CE2
- the substituent at the position was not the N-containing monocyclic ring, the highest voltage, the lowest current efficiency, and the shortest lifetime were obtained.
- the compound of the present invention when used as a light emitting layer material, it was confirmed that exhibits excellent efficiency and lifespan as compared to the comparative experimental example. It is shown that the electron stability is increased by substituting the aryl group with the 6 and 8 substitution positions of the dibenzofuran substituent.
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Abstract
The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting diode comprising same.
Description
본 발명은 2018년 5월 29일에 한국 특허청에 제출된 한국 특허 출원 제 10-2018-0061013호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다. The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0061013 filed with the Korea Intellectual Property Office on May 29, 2018, the entire contents of which are incorporated herein.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a heterocyclic compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.There is a continuing need for the development of new materials for such organic light emitting devices.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a heterocyclic compound and an organic light emitting device including the same.
본 명세서의 일 실시상태에 따르면 하기 화학식 1로 표시되는 헤테로고리 화합물을 제공한다.According to an exemplary embodiment of the present specification provides a heterocyclic compound represented by the formula (1).
[화학식 1][Formula 1]
상기 화학식 1에 있어서, In Chemical Formula 1,
X1 내지 X3은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CH이며X1 to X3 are the same as or different from each other, and each independently N or CH
X1 내지 X3 중 어느 하나 이상은 N이고,At least one of X1 to X3 is N,
R1은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 카복시기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고, R1 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxy group , Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted Heteroaryl group,
Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
L은 직절결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Y는 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고, Z는 치환 또는 비치환된 아릴기이며,Y is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Z is substituted or Unsubstituted aryl group,
L가 직접결합이고, Y가 치환 또는 비치환된 아릴기인 경우, Y와 Z는 상이하며, When L is a direct bond and Y is a substituted or unsubstituted aryl group, Y and Z are different,
a는 0 내지 5의 정수이고,a is an integer from 0 to 5,
상기 a가 복수일 때, 상기 R1은 서로 같거나 상이하다.When a is a plurality, R1 is the same as or different from each other.
또한, 본 명세서는 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 또는 2층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 헤테로고리 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound. .
본 명세서의 일 실시상태에 따른 헤테로고리 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다. The heterocyclic compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.
도 1은 본 명세서의 일 실시상태에 따르는 유기 발광 소자를 도시한 것이다.1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
도 2는 본 명세서의 일 실시상태에 따르는 유기 발광 소자를 도시한 것이다.2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Description of the code]
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 유기물층3: organic layer
4: 제2 전극4: second electrode
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 전자저지층7: electronic jersey
8: 발광층8: light emitting layer
9: 전자수송층9: electron transport layer
10:전자주입층10: electron injection layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification is demonstrated in detail.
본 명세서는 상기 화학식 1로 표시되는 헤테로고리 화합물을 제공한다.The present specification provides a heterocyclic compound represented by Chemical Formula 1.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, it means that it may further include other components, without excluding the other components unless otherwise stated.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.
본 명세서에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in the present specification are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치, 즉 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 아릴기로 치환된 아릴기, 헤테로아릴기로 치환된 아릴기, 아릴기로 치환된 헤테로고리기, 알킬기로 치환된 아릴기 등일 수 있다. As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
본 명세서에 있어서, 할로겐기는 불소, 염소, 브롬 또는 요오드가 될 수 있다.In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 탄소수 1 내지 20인 것이 바람직하다. 더 구체적으로 탄소수 1 내지 10인 것이 바람직하다. 구체적으로, 메톡시기; 에톡시기; n-프로폭시기; 이소프로폭시기; i-프로필옥시기; n-부톡시기; 이소부톡시기; tert-부톡시기; sec-부톡시기; n-펜틸옥시기; 네오펜틸옥시기; 이소펜틸옥시기; n-헥실옥시기; 3,3-디메틸부틸옥시기; 2-에틸부틸옥시기; n-옥틸옥시기; n-노닐옥시기; n-데실옥시기; 벤질옥시기; p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferable that it is C1-C20. More specifically, it is preferable that it is C1-C10. Specifically, methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group and the like, but is not limited thereto.
본 명세서에 있어서, 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 더 구체적으로는 탄소수 2 내지 20인 것이 바람직하다. 구체적인 예로는 비닐기; 1-프로페닐기; 이소프로페닐기; 1-부테닐기; 2-부테닐기; 3-부테닐기; 1-펜테닐기; 2-펜테닐기; 3-펜테닐기; 3-메틸-1-부테닐기; 1,3-부타디에닐기; 알릴기; 1-페닐비닐-1-일기; 2-페닐비닐-1-일기; 2,2-디페닐비닐-1-일기; 2-페닐-2-(나프틸-1-일)비닐-1-일기; 2,2-비스(디페닐-1-일)비닐-1-일기; 스틸베닐기; 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20. Specific examples include vinyl groups; 1-propenyl group; Isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; Allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl group; 2, 2-bis (diphenyl- 1-yl) vinyl- 1-yl group; Stilbenyl group; Styrenyl group and the like, but is not limited thereto.
본 명세서에 있어서, 알키닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 더 구체적으로는 탄소수 2 내지 20인 것이 바람직하다.In the present specification, the alkynyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.
본 명세서에 있어서, 포스핀옥사이드기는 구체적으로 디페닐포스핀옥사이드기; 디나프틸포스핀옥사이드기 등이 있으나 이에 한정되는 것은 아니다.In the present specification, the phosphine oxide group is specifically a diphenylphosphine oxide group; And dinaphthylphosphine oxide groups, but are not limited thereto.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 트리페닐기, 파이레닐기, 페날레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
본 명세서에 있어서, 아릴옥시기 중의 아릴기는 전술한 아릴기의 예시와 같다.In the present specification, the aryl group in the aryloxy group is the same as the example of the aryl group described above.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨라닐기, 피롤기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 피리딜기, 바이피리딜기, 피리미딜기, 트리아지닐기, 트리아졸릴기, 아크리딜기, 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미딜기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀리닐기, 인돌릴기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤리닐기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.
본 명세서에 있어서, 아릴렌기는 2가인 점을 제외하고, 아릴기의 정의와 같다.In the present specification, the arylene group is the same as the definition of an aryl group except that it is divalent.
본 명세서에 있어서, 헤테로아릴렌기는 2가인 점을 제외하고, 헤테로아릴기의 정의와 같다.In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula 1-1.
[화학식 1-1][Formula 1-1]
상기 화학식 1-1에 있어서, 상기 X1 내지 X3, L, Y, Ar1, Ar2, R 및 a는 상기 화학식 1에서 정의한 바와 같고, In Chemical Formula 1-1, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,
R2 및 R'은 서로 같거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 카복시기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고,R2 and R 'are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted A substituted aryloxy group or a substituted or unsubstituted heteroaryl group,
b 및 m은 0 내지 5의 정수이고, b and m are integers from 0 to 5,
b+m≤5이고,b + m ≦ 5,
n은 0 내지 1의 정수이며, n is an integer from 0 to 1,
상기 b가 복수일 때, 상기 R2는 서로 같거나 상이하고, When b is a plurality, R2 is the same as or different from each other,
상기 m이 복수일 때, 상기 R'은 서로 같거나 상이하다.When m is plural, the R's are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2 내지 화학식 4 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에 있어서, 상기 X1 내지 X3, L, Y, Ar1, Ar2, R 및 a는 상기 화학식 1에서 정의한 바와 같고, In Chemical Formulas 2 to 4, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,
R2 내지 R6은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 카복시기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고, R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group or substituted or unsubstituted heteroaryl group,
b, d 및 f는 각각 0 내지 5의 정수이고,b, d and f are each an integer of 0 to 5,
c 및 e는 각각 0 내지 4의 정수이고,c and e are each an integer of 0 to 4,
상기 b가 복수일 때, 상기 R2는 서로 같거나 상이하고,When b is a plurality, R2 is the same as or different from each other,
상기 c가 복수일 때, 상기 R3은 서로 같거나 상이하고,When c is a plurality, R3 is the same as or different from each other,
상기 d가 복수일 때, 상기 R4는 서로 같거나 상이하고,When d is a plurality, R4 is the same as or different from each other,
상기 e가 복수일 때, 상기 R5는 서로 같거나 상이하고,When e is plural, R5 is the same as or different from each other,
상기 f가 복수일 때, 상기 R6은 서로 같거나 상이하다.When f is plural, R6 is the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 5 내지 화학식 7 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 5 to 7.
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 5 내지 7에 있어서, 상기 X1 내지 X3, L, Y, Ar1, Ar2, R 및 a는 상기 화학식 1에서 정의한 바와 같다.In Formulas 5 to 7, wherein X1 to X3, L, Y, Ar1, Ar2, R and a are as defined in the formula (1).
본 명세서의 일 실시상태에 따르면, 상기 X1은 N이고, 상기 X2 및 X3은 CH이다.According to an exemplary embodiment of the present specification, X1 is N, and X2 and X3 are CH.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N이고, 상기 X1 및 X3은 CH이다.According to an exemplary embodiment of the present specification, X2 is N, and X1 and X3 are CH.
본 명세서의 일 실시상태에 따르면, 상기 X3은 N이고, 상기 X1 및 X2는 CH이다.According to an exemplary embodiment of the present specification, X3 is N, and X1 and X2 are CH.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X2는 N이고, 상기 X3은 CH이다.According to an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CH.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X3은 N이고, 상기 X2는 CH이다.According to an exemplary embodiment of the present specification, X1 and X3 are N, and X2 is CH.
본 명세서의 일 실시상태에 따르면, 상기 X2 및 X3은 N이고, 상기 X2는 CH이다.According to an exemplary embodiment of the present specification, X2 and X3 are N, and X2 is CH.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X3은 N이다.According to an exemplary embodiment of the present specification, X1 to X3 is N.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R6은 수소이다. According to an exemplary embodiment of the present specification, the R1 to R6 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 Z는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, Z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Z는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 비페닐기, 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present specification, Z is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다. According to an exemplary embodiment of the present specification, Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Y는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 N, O, 및 S 중 어느 하나 이상을 포함하는 헤테로아릴기이다. According to an exemplary embodiment of the present specification, Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group containing any one or more of N, O, and S having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Y는 알킬기; 실릴기; 포스핀옥사이드기; 아릴기; 또는 헤테로아릴기이고, According to an exemplary embodiment of the present specification, Y is an alkyl group; Silyl groups; Phosphine oxide groups; Aryl group; Or a heteroaryl group,
상기 알킬기; 실릴기; 포스핀옥사이드기; 아릴기; 또는 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기로 치환 또는 비치환된다. The alkyl group; Silyl groups; Phosphine oxide groups; Aryl group; Or a heteroaryl group is unsubstituted or substituted with a deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 탄소수 1 내지 10의 알킬기; 실릴기; 포스핀옥사이드기; 탄소수 6 내지 30의 아릴기; 또는 탄소수 3 내지 30의 헤테로아릴기이고, According to an exemplary embodiment of the present specification, Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms,
상기 탄소수 1 내지 10의 알킬기; 실릴기; 포스핀옥사이드기; 탄소수 6 내지 30의 아릴기; 또는 탄소수 3 내지 30의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기로 치환 또는 비치환된다. The alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms is unsubstituted or substituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 페닐기; 비페닐기; 나프틸기; 터페닐기; 트리페닐렌기; 페난트렌기; 플루오란텐기; 벤조옥사졸기; 벤조티아졸기; 벤조퓨로피리미딘기; 벤조티에노피리미딘기; 포스핀옥사이드기; 피리딘기; 피리미딘기; 트리아진기; 메틸기; 또는 실릴기이고, According to an exemplary embodiment of the present specification, Y is a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group; Methyl group; Or silyl group,
상기 페닐기; 비페닐기; 나프틸기; 터페닐기; 트리페닐렌기; 페난트렌기; 플루오란텐기; 벤조옥사졸기; 벤조티아졸기; 벤조퓨로피리미딘기; 벤조티에노피리미딘기; 포스핀옥사이드기; 피리딘기; 피리미딘기; 트리아진기; 메틸기; 또는 실릴기는 중수소, 니트릴기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기로 치환 또는 비치환된다. The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group; Methyl group; Or the silyl group is unsubstituted or substituted with deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 탄소수 1 내지 10의 알킬기; 실릴기; 포스핀옥사이드기; 탄소수 6 내지 30의 단환의 아릴기; 탄소수 10 내지 30의 다환의 아릴기; 탄소수 3 내지 30의 단환의 헤테로아릴기 또는 탄소수 3 내지 30의 다환의 헤테로아릴기이고, According to an exemplary embodiment of the present specification, Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Monocyclic aryl groups having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms,
상기 탄소수 6 내지 30의 단환의 아릴기; 탄소수 10 내지 30의 다환의 아릴기; 탄소수 3 내지 30의 단환의 헤테로아릴기 또는 탄소수 3 내지 30의 다환의 헤테로아릴기는 중수소, 니트릴기, 할로겐기, 아릴기로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기로 치환된 실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 N, O 또는 S 중 어느 하나 이상을 포함하는 헤테로아릴기, 또는 알킬기 또는 아릴기로 치환 또는 비치환된 포스핀옥사이드기로 치환 또는 비치환된다.The monocyclic aryl group having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl groups having 3 to 30 carbon atoms or polycyclic heteroaryl groups having 3 to 30 carbon atoms are deuterium, nitrile, halogen, aryl substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted carbon atoms 6 A silaryl group substituted with an aryl group of 30 to 30, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group including any one or more of N, O or S having 3 to 30 carbon atoms substituted or unsubstituted, or Substituted or unsubstituted with an phosphine oxide group unsubstituted or substituted with an alkyl or aryl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 니트릴기, 트리페닐메틸기, 나프틸기, 페닐나프틸기, 트리페닐실릴기, 또는 트리메틸실릴기로 치환 또는 비치환된 페닐기; 나프틸기; 비페닐기; 페난트렌기; 터페닐기; 트리페닐렌기; 플루오란텐기; 벤조옥사졸기; 벤조티아졸기; 페닐기로 치환 또는 비치환된 벤조퓨로피리미딘기; 페닐기로 치환 또는 비치환된 벤조티에노피리미딘기; 페닐기로 치환된 포스핀옥사이드기; 페닐기로 치환 또는 비치환된 피리딘기; 페닐기로 치환 또는 비치환된 피리미딘기; 또는 페닐기로 치환 또는 비치환된 트리아진기이다.According to an exemplary embodiment of the present specification, Y is a phenyl group unsubstituted or substituted with a nitrile group, triphenylmethyl group, naphthyl group, phenylnaphthyl group, triphenylsilyl group, or trimethylsilyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Terphenyl group; Triphenylene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; A benzopuropyrimidine group unsubstituted or substituted with a phenyl group; A benzothienopyrimidine group unsubstituted or substituted with a phenyl group; Phosphine oxide groups substituted with phenyl groups; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; Or a triazine group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Y는 하기 치환기들 중 선택되는 어느 하나일 수 있다.According to an exemplary embodiment of the present specification, Y may be any one selected from the following substituents.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms to be.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같고, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같고, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같고, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환의 아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 다환의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 단환의 헤테로아릴기또는 치환 또는 비치환된 탄소수 3 내지 30의 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polycyclic group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted monocyclic heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 나프틸기; 터페닐기; 플루오렌기; 스피로비플루오렌기; 페난트렌기; 트리페닐렌기; 카바졸기; 디벤조퓨란기; 디벤조티오펜기; 벤조나프토퓨란기; 또는 벤조나프토티오펜기이고, According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
상기 페닐기; 비페닐기; 나프틸기; 터페닐기; 플루오렌기; 스피로비플루오렌기; 페난트렌기; 트리페닐렌기; 카바졸기; 디벤조퓨란기; 디벤조티오펜기; 벤조나프토퓨란기; 또는 벤조나프토티오펜기는 중수소; 할로겐기; 탄소수 1 내지 10의 알킬기; 탄소수 1 내지 10의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 및 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기로 이루어진 군에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다. The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Halogen group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 나프틸기; 터페닐기; 플루오렌기; 스피로비플루오렌기; 페난트렌기; 트리페닐렌기; 카바졸기; 디벤조퓨란기; 디벤조티오펜기; 벤조나프토퓨란기; 또는 벤조나프토티오펜기이고, According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
상기 페닐기; 비페닐기; 나프틸기; 터페닐기; 플루오렌기; 스피로비플루오렌기; 페난트렌기; 트리페닐렌기; 카바졸기; 디벤조퓨란기; 디벤조티오펜기; 벤조나프토퓨란기; 또는 벤조나프토티오펜기는 중수소; 페닐기; 나프틸기; 및 메틸기로 이루어진 군에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Phenyl group; Naphthyl group; And one or more substituents selected from the group consisting of methyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 페닐기로 치환 또는 비치환된 카바졸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1는 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 페닐기로 치환 또는 비치환된 카바졸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar2는 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트렌기; 페닐기로 치환 또는 비치환된 카바졸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 탄소수 6 내지 30의 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 탄소수 6 내지 30의 단환의 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 탄소수 10 내지 30의 다환의 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 나프틸렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 쿼터페닐기, 치환 또는 비치환된 2가의 플루오렌기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 트리페닐렌기, 또는 치환 또는 비치환된 2가의 페난트렌기이다.According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, substituted Or an unsubstituted divalent quarterphenyl group, a substituted or unsubstituted divalent fluorene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent triphenylene group Or a substituted or unsubstituted divalent phenanthrene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 페닐렌기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 나프틸렌기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 비페닐기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 터페닐기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 쿼터페닐기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 플루오렌기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 안트라센기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 파이렌기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 트리페닐렌기, 또는 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 페난트렌기이다.According to an exemplary embodiment of the present specification, L is a phenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A substituted or unsubstituted bivalent biphenyl group, a divalent terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent quarterphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A divalent fluorene group unsubstituted or substituted with a divalent anthracene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and having 1 to 10 carbon atoms. Or a divalent phenanthrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 페닐렌기, 나프틸렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 쿼터페닐기, 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 2가의 플루오렌기, 2가의 안트라센기, 2가의 파이렌기, 2가의 트리페닐렌기, 또는 2가의 페난트렌기이다.According to an exemplary embodiment of the present specification, L is a phenylene group, naphthylene group, divalent biphenyl group, divalent terphenyl group, divalent quarterphenyl group, divalent fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms Group, a bivalent anthracene group, a bivalent pyrene group, a bivalent triphenylene group, or a bivalent phenanthrene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합이다.According to an exemplary embodiment of the present specification, L is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L은 페닐렌기이다.According to an exemplary embodiment of the present specification, L is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L is a divalent naphthyl group.
본 명세서의 또 하나의 실시상태에 따르면, 상기 화학식 1의 헤테로고리 화합물은 하기 구조식들로 표시될 수 있다.According to yet an embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be represented by the following structural formula.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 또는 2층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 헤테로고리 화합물을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers may include the aforementioned heterocyclic compound.
예컨대, 본 발명의 유기 발광 소자의 구조는 도 1 에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
도 1에는 기판(1) 위에 제1 전극(2), 유기물층(3), 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다.1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
도 2에는 기판(1) 위에 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자저지층(7), 발광층(8), 전자수송층(9), 전자주입층(10) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 본 발명의 화합물은 특히 정공주입층, 정공수송층, 전자저지층, 발광층, 전자수송층, 전자주입층에 포함될 수 있고, 바람직하게는 발광층에 포함될 수 있다. 2, the first electrode 2, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, and the electron injection layer The structure of the organic light emitting device in which 10) and the second electrode 4 are sequentially stacked is illustrated. In particular, the compound of the present invention may be included in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and preferably may be included in a light emitting layer.
상기 도 1 및 2는 유기 발광 소자를 예시한 것이며 이에 한정되지 않는다. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 포함한다.In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
본 발명의 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 호스트와 도펀트를 90:10 내지 50:50의 질량비로 포함한다.The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 50:50.
본 발명의 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 호스트와 도펀트를 90:10 내지 60:40의 질량비로 포함한다.The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 60:40.
본 발명의 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 호스트와 도펀트를 90:10 내지 80:20의 질량비로 포함한다.The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 80:20.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 호스트로 포함한다.In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 추가의 호스트를 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an additional host.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 유기화합물을 추가의 호스트로 포함할 수 있다.In one embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an organic compound as an additional host.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 카바졸 유도체를 추가의 호스트로 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer may include a carbazole derivative as an additional host.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 비카바졸 화합물을 추가의 호스트로 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a bicarbazole compound as an additional host.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 X의 화합물을 추가의 호스트로 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound of Formula X as an additional host.
[화학식 X][Formula X]
상기 화학식 X에 있어서, In Chemical Formula X,
Ax 및 Ay는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, Ax and Ay are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
Rx 및 Ry는 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고,Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or Unsubstituted heteroaryl group,
x 및 y는 각각 0 내지 7의 정수이고,x and y are each an integer of 0 to 7,
x 및 y가 각각 복수일 때, 괄호안의 치환기는 서로 같거나 상이하다.When x and y are each plural, substituents in parentheses are the same or different from each other.
본 발명의 일 실시상태에 있어서, 상기 Ax 및 Ay는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 아릴기이다.In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms.
본 발명의 일 실시상태에 있어서, 상기 Ax 및 Ay는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 비페닐기, 터페닐기, 안트라센기, 페난트렌기, 트리페닐렌기, 플루오렌기 또는 파이렌기이다.In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a fluorene group, or a pyrene group.
본 발명의 일 실시상태에 있어서, 상기 Ax 및 Ay는 서로 같거나 상이하고, 각각 독립적으로 페닐기 또는 비페닐기이다.In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and are each independently a phenyl group or a biphenyl group.
본 발명의 일 실시상태에 있어서, 상기 Rx 및 Ry는 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 또는 치환 또는 비치환된 알킬기이다. In one embodiment of the present invention, Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.
본 발명의 일 실시상태에 있어서, 상기 Rx 및 Ry는 수소이다. In one embodiment of the present invention, Rx and Ry are hydrogen.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 추가의 도펀트를 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an additional dopant.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 형광 도펀트를 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a fluorescent dopant.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광 도펀트를 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a phosphorescent dopant.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 이리듐계 도펀트를 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an iridium-based dopant.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 헤테로고리 화합물을 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the heterocyclic compound. have.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 전자주입층, 전자수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자수송층, 또는 전자 주입 및 수송층은 상기 헤테로고리 화합물을 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer may include the heterocyclic compound. have.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 전자저지층, 또는 정공저지층을 포함하고, 상기 전자저지층, 또는 정공저지층은 상기 헤테로고리 화합물을 포함할 수 있다.In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
상기 화학식 1의 헤테로고리 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The preparation method of the heterocyclic compound of Formula 1 and the manufacture of an organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
하기 제조방법에서 치환기의 종류 및 치환위치를 달리하여 본 명세서에 기재된 모든 화합물을 제조할 수 있다. In the following preparation method, all compounds described in the present specification may be prepared by changing the type and the substitution position of the substituents.
[ [
제조예Production Example
]]
제조예Production Example
1: 화합물 1A 내지 1D의 제조 1: Preparation of Compounds 1A to 1D
1) 화합물 1A의 제조1) Preparation of Compound 1A
질소 분위기에서 2-클로로-4,6-디페닐-1,3,5-트리아진 (50.0 g, 187 mmol)와 (2-클로로-3-플루오로페닐)보론산 (48.9 g, 280 mmol)를 테트라하이드로퓨란 400 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(77.6 g, 561 mmol)를 물 210 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(6.5 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 1A(52.1 g, 77%)을 제조하였다. 2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 187 mmol) and (2-chloro-3-fluorophenyl) boronic acid (48.9 g, 280 mmol) in a nitrogen atmosphere Was added to 400 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 1A (52.1 g, 77%) through ethyl acetate recrystallization.
MS: [M+H]+ = 362MS: [M + H] < + > = 362
2) 화합물 1B의 제조2) Preparation of Compound 1B
질소 분위기에서 화합물 1A (52.1 g, 144 mmol)와 (3-클로로-2-히드록시페닐)보론산 (37.6 g, 216 mmol)를 테트라하이드로퓨란 400 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(77.6 g, 561 mmol)를 물 210 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(6.5 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 헥산과 에틸아세테이트 컬럼을 통해 화합물 1B(32.0 g, 49%)을 제조하였다. Compound 1A (52.1 g, 144 mmol) and (3-chloro-2-hydroxyphenyl) boronic acid (37.6 g, 216 mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 1B (32.0 g, 49%) through hexane and ethyl acetate column.
MS: [M+H]+ = 454MS: [M + H] < + > = 454
3) 화합물 1C의 제조3) Preparation of Compound 1C
질소 분위기에서 화합물 1B (32.0 g, 144 mmol)를 클로로포름 300ml에 녹여 투입하고 0℃에서 충분히 교반한후 N-브로모석시드이미드(11.8g, 71 mmol)를 부분적으로 천천히 적가하였다. 서서히 상온으로 승온한 후 1시간 반응 후 물을 투입하여 반응을 종결하였다. 이후 물과 싸이오황산 나트륨 용액을 이용하여 각각 2회 추출한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 1C(31.9 g, 85%)을 제조하였다.Compound 1B (32.0 g, 144 mmol) was dissolved in 300 ml of chloroform in a nitrogen atmosphere, sufficiently stirred at 0 ° C., and N-bromosuccisidimide (11.8 g, 71 mmol) was added slowly dropwise thereto. After gradually raising the temperature to room temperature, the reaction was terminated by adding water after the reaction for 1 hour. After extracting twice each using water and sodium thiosulfate solution, the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was dried, and then compound 1C (31.9 g, 85%) was prepared through ethyl acetate recrystallization.
MS: [M+H]+ = 532MS: [M + H] < + > = 532
4) 화합물 1D의 제조4) Preparation of Compound 1D
질소 분위기에서 화합물 1C(31.9 g, 60 mmol)을 다이메틸로픔아마이드 200 ml에 넣고 교반하였다. 이후 포타슘카보네이트(16.6 g, 120 mmol)를 투입한 후 환류하였다. 2시간 후 상온으로 온도를 낮추고 여과하였다. 여과물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 감압증류 후 에틸 아세테이트를 이용해 재결정하였다. 생성된 고체를 여과 후 건조하여 화합물 1D(21.8 g, 71%)을 제조하였다.Compound 1C (31.9 g, 60 mmol) was added to 200 ml of dimethyllotamide in a nitrogen atmosphere and stirred. Then potassium carbonate (16.6 g, 120 mmol) was added and refluxed. After 2 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 1D (21.8 g, 71%).
MS: [M+H]+ = 512MS: [M + H] < + > = 512
제조예Production Example
2: 화합물 2A 내지 2B의 제조 2: Preparation of Compounds 2A to 2B
1) 화합물 2A의 제조1) Preparation of Compound 2A
질소 분위기에서 화합물 1D (25.0 g, 49 mmol)와 페닐보론산 (7.2 g, 59 mmol)를 테트라하이드로퓨란 200 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(20.3 g, 147 mmol)를 물 60 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(1.7 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 2A(19.2 g, 77%)을 제조하였다. Compound 1D (25.0 g, 49 mmol) and phenylboronic acid (7.2 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 2A (19.2 g, 77%) through ethyl acetate recrystallization.
MS: [M+H]+ = 510MS: [M + H] < + > = 510
2) 화합물 2B의 제조2) Preparation of Compound 2B
질소 분위기에서 중간체 2A(19.2 g, 38 mmol) ,비스(피나콜라토)다이보론(10.2g, 45mmol) 및 아세트산칼륨(7.4 g, 75 mmol)을 섞고, 디옥산 200 ml에 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스(디벤질리딘아세톤)팔라듐(0.7 g, 1.1 mmol)과 트리사이클로헥실포스핀(0.7 g, 2.3 mmol)을 넣고 3시간 동안 가열, 교반하였다. 반응 종료 후, 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고, 유기층을 무수황산마그네슘으로 건조하였다. 감압 증류 후 에탄올로 재결정하여 화합물 2B(18.1g, 80%)를 제조하였다.Intermediate 2A (19.2 g, 38 mmol), bis (pinacolato) diboron (10.2 g, 45 mmol) and potassium acetate (7.4 g, 75 mmol) are mixed in a nitrogen atmosphere, added to 200 ml of dioxane and heated with stirring It was. At reflux, bis (dibenzylideneacetone) palladium (0.7 g, 1.1 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, and the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, compound 2B (18.1 g, 80%) was prepared by recrystallization with ethanol.
MS: [M+H]+ = 602MS: [M + H] < + > = 602
제조예Production Example
3: 화합물 3A 내지 3B의 제조 3: Preparation of Compounds 3A to 3B
1) 화합물 3A의 제조1) Preparation of Compound 3A
질소 분위기에서 화합물 1D (25.0 g, 49 mmol)와 [1,1'-비페닐]-4-일보론산 (11.6 g, 59 mmol)를 테트라하이드로퓨란 200 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(20.3 g, 147 mmol)를 물 60 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(1.7 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 3A(23.8 g, 83%)을 제조하였다. Compound 1D (25.0 g, 49 mmol) and [1,1'-biphenyl] -4-ylboronic acid (11.6 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After 12 hours of reaction, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 3A (23.8 g, 83%) through ethyl acetate recrystallization.
MS: [M+H]+ = 586MS: [M + H] < + > = 586
1) 화합물 3B의 제조1) Preparation of Compound 3B
질소 분위기에서 중간체 3A(23.8 g, 41 mmol), 비스(피나콜라토)다이보론(11.3g, 45mmol) 및 아세트산칼륨(7.4 g, 75 mmol)을 섞고, 디옥산 200 ml에 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스(디벤질리딘아세톤)팔라듐(0.7 g, 1.2 mmol)과 트리사이클로헥실포스핀(0.7 g, 2.4 mmol)을 넣고 5시간 동안 가열, 교반하였다. 반응 종료 후, 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고, 유기층을 무수황산마그네슘으로 건조하였다. 감압 증류 후 에탄올로 재결정하여 화합물 3B(24.2g, 88%)를 제조하였다.Intermediate 3A (23.8 g, 41 mmol), bis (pinacolato) diboron (11.3 g, 45 mmol) and potassium acetate (7.4 g, 75 mmol) are mixed in a nitrogen atmosphere, added to 200 ml of dioxane and heated with stirring It was. Bis (dibenzylideneacetone) palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added under reflux, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, and the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. Compound 3B (24.2 g, 88%) was prepared by recrystallization with ethanol after distillation under reduced pressure.
MS: [M+H]+ = 678MS: [M + H] < + > = 678
제조예Production Example
4: 화합물 4A 내지 4B의 제조 4: Preparation of Compounds 4A-4B
1) 화합물 4A의 제조1) Preparation of Compound 4A
질소 분위기에서 화합물 1D (25.0 g, 49 mmol)와 [1,1'-비페닐]-3-일보론산 (11.6 g, 59 mmol)를 테트라하이드로퓨란 200 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(20.3 g, 147 mmol)를 물 60 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(1.7 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 4A(18.9 g, 66%)을 제조하였다. Compound 1D (25.0 g, 49 mmol) and [1,1'-biphenyl] -3-ylboronic acid (11.6 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 4A (18.9 g, 66%) through ethyl acetate recrystallization.
MS: [M+H]+ = 586MS: [M + H] < + > = 586
2) 화합물 4B의 제조2) Preparation of Compound 4B
질소 분위기에서 중간체 4A(18.9 g, 32 mmol) ,비스(피나콜라토)다이보론(9.0g, 35mmol) 및 아세트산칼륨(6.3 g, 65 mmol)을 섞고, 디옥산 200 ml에 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스(디벤질리딘아세톤)팔라듐(0.6 g, 1.0 mmol)과 트리사이클로헥실포스핀(0.6 g, 1.9 mmol)을 넣고 5시간 동안 가열, 교반하였다. 반응 종료 후, 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고, 유기층을 무수황산마그네슘으로 건조하였다. 감압 증류 후 에탄올로 재결정하여 화합물 4B(10.9g, 50%)를 제조하였다.In a nitrogen atmosphere, intermediate 4A (18.9 g, 32 mmol), bis (pinacolato) diboron (9.0 g, 35 mmol) and potassium acetate (6.3 g, 65 mmol) are mixed, added to 200 ml of dioxane and heated with stirring It was. At reflux, bis (dibenzylideneacetone) palladium (0.6 g, 1.0 mmol) and tricyclohexylphosphine (0.6 g, 1.9 mmol) were added thereto, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, and the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. Compound 4B (10.9 g, 50%) was prepared by recrystallization with ethanol after distillation under reduced pressure.
MS: [M+H]+ = 678MS: [M + H] < + > = 678
제조예Production Example
5: 화합물 1 내지 15의 제조 5: Preparation of Compounds 1-15
1) 화합물 1의 합성1) Synthesis of Compound 1
질소 분위기에서 중간체 2A (10g, 20mmol) 및 [1,1'-비페닐]-4-일보론산 (8.0g, 40mmol)를 다이옥세인 100ml에 넣고 교반 및 환류 하였다. 이 후 포타슘포스페이트(12.5g, 59mmol)를 물 40ml에 녹여 투입한 후 충분히 교반 후 비스(디벤질리딘아세톤)팔라듐(0.3g, 0.6mmol)과 트리사이클로헥실포스핀(0.3mg, 1.2mmol)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 여과하였다. 여과물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 감압증류 후 에틸 아세테이트를 이용해 재결정하였다. 생성된 고체를 여과 후 건조하여 화합물 1(9.5g, 77%)을 제조하였다.In a nitrogen atmosphere, intermediate 2A (10 g, 20 mmol) and [1,1'-biphenyl] -4-ylboronic acid (8.0 g, 40 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (12.5g, 59mmol) in 40ml of water, the mixture was sufficiently stirred, and then stirred thoroughly. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to give compound 1 (9.5 g, 77%).
MS: [M+H]+ = 628MS: [M + H] < + > = 628
2) 화합물 2의 합성2) Synthesis of Compound 2
[1,1'-비페닐]-4-일보론산 대신 상기 화합물을 사용한 것을 제외하고, 화합물 1의 합성과 같은 방법을 통해 화합물 2(9.5g, 54%)을 합성하였다.Compound 2 (9.5 g, 54%) was synthesized in the same manner as in the synthesis of Compound 1, except that the compound was used instead of [1,1'-biphenyl] -4-ylboronic acid.
MS: [M+H]+ = 704MS: [M + H] < + > = 704
3) 화합물 3의 합성3) Synthesis of Compound 3
[1,1'-비페닐]-4-일보론산 대신 페난트렌-2-일보론산을 사용한 것을 제외하고, 화합물 1의 합성과 같은 방법을 통해 화합물 3(10.6g, 83%)을 합성하였다.Compound 3 (10.6 g, 83%) was synthesized in the same manner as in the synthesis of Compound 1, except that phenanthrene-2-ylboronic acid was used instead of [1,1'-biphenyl] -4-ylboronic acid.
MS: [M+H]+ = 652MS: [M + H] < + > = 652
4) 화합물 4의 합성4) Synthesis of Compound 4
질소 분위기에서 화합물 2B (10.0 g, 17 mmol)와 2-클로로벤조[d]티아졸 (3.1 g, 18 mmol)를 테트라하이드로퓨란 100 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(6.9 g, 49 mmol)를 물 20 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(0.6 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 4(4.5 g, 44%)을 제조하였다. Compound 2B (10.0 g, 17 mmol) and 2-chlorobenzo [d] thiazole (3.1 g, 18 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.9 g, 49 mmol) was dissolved in 20 ml of water, and stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.6 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 4 (4.5 g, 44%) through ethyl acetate recrystallization.
MS: [M+H]+ = 609MS: [M + H] < + > = 609
5) 화합물 5의 합성5) Synthesis of Compound 5
2-클로로벤조[d]티아졸 대신 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을제외하고, 상기 화합물 4의 합성과 같은 방법을 통해 화합물 5(8.7g, 74%)을 합성하였다.Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine in place of 2-chlorobenzo [d] thiazole, Compound 5 (8.7 g) was prepared in the same manner as in the synthesis of Compound 4. , 74%).
MS: [M+H]+ = 707MS: [M + H] < + > = 707
6) 화합물 6의 합성6) Synthesis of Compound 6
질소 분위기에서 중간체 3A (10g, 17mmol) 및 페닐보론산 (2.2g, 19mmol)를 다이옥세인 100ml에 넣고 교반 및 환류 하였다. 이 후 포타슘포스페이트(10.9g, 52mmol)를 물 30ml에 녹여 투입한 후 충분히 교반 후 비스(디벤질리딘아세톤)팔라듐(0.3g, 0.6mmol)과 트리사이클로헥실포스핀(0.3mg, 1.2mmol)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 여과하였다. 여과물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 감압증류 후 에틸 아세테이트를 이용해 재결정하였다. 생성된 고체를 여과 후 건조하여 화합물 6(6.8g, 63%)을 제조하였다.In a nitrogen atmosphere, intermediate 3A (10 g, 17 mmol) and phenylboronic acid (2.2 g, 19 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (10.9g, 52mmol) in 30ml of water, the mixture was sufficiently stirred, and then stirred thoroughly. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 6 (6.8 g, 63%).
MS: [M+H]+ = 628MS: [M + H] < + > = 628
7)화합물 7의 합성7) Synthesis of Compound 7
페닐보론산 대신 비페닐-3-일보론산을 사용한 것을 제외하고, 상기 화합물 6의 합성과 같은 방법을 통해 화합물 7(6.6g, 55%)을 합성하였다.Compound 7 (6.6 g, 55%) was synthesized in the same manner as in the synthesis of Compound 6, except that biphenyl-3-ylboronic acid was used instead of phenylboronic acid.
MS: [M+H]+ = 704MS: [M + H] < + > = 704
8) 화합물 8의 합성8) Synthesis of Compound 8
페닐보론산 대신 나프탈렌-2-일보론산을 사용한 것을 제외하고, 상기 화합물 6의 합성과 같은 방법을 통해 화합물 8(9.0g, 78%)을 합성하였다.Synthesis of Compound 6 was repeated except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid. Compound 8 (9.0 g, 78%) was synthesized through the method.
MS: [M+H]+ = 678MS: [M + H] < + > = 678
9) 화합물 9의 합성9) Synthesis of Compound 9
질소 분위기에서 화합물 3B (10.0 g, 15 mmol)와 2-클로로벤조[d]티아졸 (2.7 g, 16 mmol)를 테트라하이드로퓨란 100 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(6.1 g, 44 mmol)를 물 20 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(0.5 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 9(8.1 g, 80%)을 제조하였다. Compound 3B (10.0 g, 15 mmol) and 2-chlorobenzo [d] thiazole (2.7 g, 16 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.1 g, 44 mmol) was dissolved in 20 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 9 (8.1 g, 80%) through ethyl acetate recrystallization.
MS: [M+H]+ = 685MS: [M + H] < + > = 685
10) 화합물 10의 합성10) Synthesis of Compound 10
2-클로로벤조[d]티아졸 대신 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을 제외하고, 상기 화합물 9의 합성과 같은 방법을 통해 화합물 10(9.1g, 79%)을 합성하였다.Compound 10 (9.1 g) was prepared in the same manner as in the synthesis of Compound 9, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chlorobenzo [d] thiazole. , 79%) was synthesized.
MS: [M+H]+ = 783MS: [M + H] < + > = 783
11) 화합물 11의 합성11) Synthesis of Compound 11
질소 분위기에서 중간체 4A (10g, 17mmol) 및 페닐보론산 (2.2g, 19mmol)를 다이옥세인 100ml에 넣고 교반 및 환류 하였다. 이 후 포타슘포스페이트(10.9g, 52mmol)를 물 30ml에 녹여 투입한 후 충분히 교반 후 비스(디벤질리딘아세톤)팔라듐(0.3g, 0.6mmol)과 트리사이클로헥실포스핀(0.3mg, 1.2mmol)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 여과하였다. 여과물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 감압증류 후 에틸 아세테이트를 이용해 재결정하였다. 생성된 고체를 여과 후 건조하여 화합물 11(7.4g, 64%)을 제조하였다.In a nitrogen atmosphere, intermediate 4A (10 g, 17 mmol) and phenylboronic acid (2.2 g, 19 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (10.9g, 52mmol) in 30ml of water, the mixture was sufficiently stirred, and then stirred thoroughly. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 11 (7.4 g, 64%).
MS: [M+H]+ = 678MS: [M + H] < + > = 678
12) 화합물 12의 합성12) Synthesis of Compound 12
페닐보론산 대신 [1,1'-비페닐]-4-일보론산을 사용한 것을 제외하고, 상기 화합물 11의 합성과 같은 방법을 통해 화합물 12(6.8g, 57%)을 합성하였다.Compound 12 (6.8 g, 57%) was synthesized in the same manner as in the synthesis of Compound 11, except that [1,1'-biphenyl] -4-ylboronic acid was used instead of phenylboronic acid.
MS: [M+H]+ = 704MS: [M + H] < + > = 704
13) 화합물 13의 합성13) Synthesis of Compound 13
페닐보론산 대신 나프탈렌-2-일보론산을 사용한 것을 제외하고, 상기 화합물 11의 합성과 같은 방법을 통해 화합물 13(8.1g, 70%)을 합성하였다.Compound 13 (8.1 g, 70%) was synthesized in the same manner as in the synthesis of Compound 11, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.
MS: [M+H]+ = 678MS: [M + H] < + > = 678
14) 화합물 14의 합성14) Synthesis of Compound 14
질소 분위기에서 화합물 4B (10.0 g, 15 mmol)와 2-클로로벤조[d]티아졸 (2.7 g, 16 mmol)를 테트라하이드로퓨란 100 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(6.1 g, 44 mmol)를 물 20 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(0.5 g, 3 mol%)을 투입하였다. 12시간 반응 후 상온으로 온도를 낮추고 유기층과 물층을 분리한 후 유기층을 감압 증류하였다. 증류물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 건조한 후 에틸아세테이트 재결정을 통해 화합물 14(4.2 g, 42%)을 제조하였다. Compound 4B (10.0 g, 15 mmol) and 2-chlorobenzo [d] thiazole (2.7 g, 16 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.1 g, 44 mmol) was dissolved in 20 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 14 (4.2 g, 42%) through ethyl acetate recrystallization.
MS: [M+H]+ = 685MS: [M + H] < + > = 685
15) 화합물 15의 합성15) Synthesis of Compound 15
2-클로로벤조[d]티아졸 대신 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을 제외하고, 상기 화합물 14의 합성과 같은 방법을 통해 화합물 15(6.9g, 60%)을 합성하였다.Compound 15 (6.9 g) was prepared in the same manner as in the synthesis of Compound 14, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chlorobenzo [d] thiazole. , 60%).
MS: [M+H]+ = 783MS: [M + H] < + > = 783
[[
실험예Experimental Example
]]
<<
실험예Experimental Example
1> 1>
ITO(indium tin oxide)가 1,300Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.The glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에 하기 HI-1 화합물을 50Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 HT-1 화합물을 250Å의 두께로 열 진공 증착하여 정공수송층을 형성하고, HT-1 증착막 위에 하기 HT-2 화합물을 50Å 두께로 진공 증착하여 전자저지층을 형성하였다. 상기 HT-2 증착막 위에 발광층으로서 앞서 제조한 화합물 1, 하기 YGH-1 화합물, 및 인광도펀트 YGD-1을 44:44:12의 중량비로 진공증착하여 400Å 두께의 발광층을 형성하였다. 상기 발광층 위에 하기 ET-1 화합물을 250Å의 두께로 진공 증착하여 전자수송층을 형성하고, 상기 전자수송층 위에 하기 ET-2 화합물 및 Li를 98:2의 중량비로 진공 증착하여 100Å 두께의 전자주입층을 형성하였다. 상기 전자주입층 위에 1000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. The hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 kPa on the prepared ITO transparent electrode. A hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film. Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1, prepared as a light emitting layer on the HT-2 deposited film by vacuum deposition at a weight ratio of 44:44:12, form a light emitting layer having a thickness of 400 kHz. The following ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW. Formed. Aluminum was deposited to a thickness of 1000 Å on the electron injection layer to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 Å/sec를 유지하였고, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 ~ 5 × 10-8 torr를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the aluminum was maintained at the deposition rate of 2 Å / sec, the vacuum during deposition was maintained at 1 × 10 -7 ~ 5 × 10 -8 torr It was.
<<
실험예Experimental Example
2 내지 15> 2 to 15>
상기 실험예 1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.
<비교 <Comparison
실험예Experimental Example
1 내지 3> 1 to 3
상기 실험예 1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1의 CE1 내지 CE3의 화합물은 하기와 같다.An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1. The compounds of CE1 to CE3 in Table 1 are as follows.
상기 실험예 및 비교실험예에서 유기 발광 소자를 10mA/cm2의 전류 밀도에서 전압과 효율을 측정하였고, 50mA/cm2의 전류 밀도에서 수명을 측정하여 그 결과를 하기 표 1에 나타내었다. 이때, LT95는 초기 휘도 대비 95%가 되는 시간을 의미한다. In the above experimental example and the comparative example, the organic light emitting diode was measured voltage and efficiency at a current density of 10mA / cm 2 , the lifetime was measured at a current density of 50mA / cm 2 and the results are shown in Table 1 below. In this case, LT95 means a time of 95% of the initial luminance.
| 화합물compound | 전압(V)(@10mA/cm2)Voltage (V) (@ 10mA / cm 2 ) | 효율(Cd/A)(@10mA/cm2)Efficiency (Cd / A) (@ 10mA / cm 2 ) | 색좌표(x,y)Color coordinates (x, y) | 수명(h)(LT95 at 50mA/cm2)Life (h) (LT 95 at 50mA / cm 2 ) | |
| 실험예 1Experimental Example 1 |
화합물 1 |
3.83.8 | 8080 | 0.45, 0.540.45, 0.54 | 100100 |
| 실험예 2Experimental Example 2 |
화합물 2 |
3.93.9 | 8282 | 0.46, 0.530.46, 0.53 | 120120 |
| 실험예 3Experimental Example 3 |
화합물 3 |
4.04.0 | 7878 | 0.45, 0.530.45, 0.53 | 150150 |
| 실험예 4Experimental Example 4 |
화합물 4 |
3.93.9 | 8181 | 0.45, 0.540.45, 0.54 | 125125 |
| 실험예 5Experimental Example 5 | 화합물 5Compound 5 | 3.73.7 | 8282 | 0.45, 0.540.45, 0.54 | 150150 |
| 실험예 6Experimental Example 6 |
화합물 6 |
3.83.8 | 8080 | 0.45, 0.540.45, 0.54 | 110110 |
| 실험예 7Experimental Example 7 |
화합물 7 |
3.93.9 | 8181 | 0.46, 0.530.46, 0.53 | 135135 |
| 실험예 8Experimental Example 8 |
화합물 8 |
4.04.0 | 8484 | 0.45, 0.540.45, 0.54 | 128128 |
| 실험예 9Experimental Example 9 |
화합물 9 |
4.34.3 | 8181 | 0.45, 0.540.45, 0.54 | 115115 |
| 실험예 10Experimental Example 10 |
화합물 10 |
3.93.9 | 8282 | 0.45, 0.540.45, 0.54 | 130130 |
| 실험예 11Experimental Example 11 | 화합물 11Compound 11 | 3.73.7 | 8484 | 0.46, 0.530.46, 0.53 | 100100 |
| 실험예 12Experimental Example 12 | 화합물 12Compound 12 | 3.83.8 | 8383 | 0.45, 0.540.45, 0.54 | 160160 |
| 실험예 13Experimental Example 13 | 화합물 13Compound 13 | 4.14.1 | 8080 | 0.46, 0.530.46, 0.53 | 105105 |
| 실험예 14Experimental Example 14 | 화합물 14Compound 14 | 4.04.0 | 8080 | 0.45, 0.540.45, 0.54 | 100100 |
| 실험예 15Experimental Example 15 | 화합물 15Compound 15 | 3.83.8 | 8080 | 0.45, 0.540.45, 0.54 | 105105 |
| 비교실험예 1Comparative Experimental Example 1 | CE1CE1 | 4.54.5 | 7070 | 0.46, 0.540.46, 0.54 | 8080 |
| 비교실험예 2Comparative Experimental Example 2 | CE2CE2 | 4.04.0 | 7575 | 0.47, 0.530.47, 0.53 | 3030 |
|
비교실험예 3 |
CE3CE3 | 6.06.0 | 4545 | 0.43, 0.530.43, 0.53 | 55 |
본 발명의 화합물은 디벤조퓨란 코어를 포함하지 않는 CE1과 비교하여, 더 낮은 전압, 높은 효율 및 장수명의 특성을 보였고, The compounds of the present invention showed lower voltage, higher efficiency and longer life compared to CE1 without the dibenzofuran core,
CE2와 같이 N함유 단환고리가 디벤조퓨란의 2번 위치에 결합하는 경우, 본 발명의 화합물을 사용한 실험예 1 내지 15에 비해 낮은 효율 및 현저히 짧은 수명을 보였고, CE3와 같이 디벤조퓨란의 1번 위치의 치환기가 N함유 단환고리가 아닌 경우에는 가장 높은 전압과, 낮은 전류효율 및 가장 짧은 수명을 나타냈다.When the N-containing monocyclic ring, such as CE2, is bonded to position 2 of the dibenzofuran, it showed lower efficiency and significantly shorter lifespan compared to Experimental Examples 1 to 15 using the compound of the present invention. When the substituent at the position was not the N-containing monocyclic ring, the highest voltage, the lowest current efficiency, and the shortest lifetime were obtained.
따라서, 본 발명의 화합물을 발광층 물질로 사용할 경우, 비교 실험예에 비하여 효율 및 수명이 우수한 특성을 나타내는 것을 확인할 수 있었다. 이는 디벤조퓨란치환기의 6번과 8번 치환위치를 아릴기로 치환함에 따라 전자안정성이 증가된것으로 보여진다. Therefore, when the compound of the present invention is used as a light emitting layer material, it was confirmed that exhibits excellent efficiency and lifespan as compared to the comparative experimental example. It is shown that the electron stability is increased by substituting the aryl group with the 6 and 8 substitution positions of the dibenzofuran substituent.
Claims (8)
- 하기 화학식 1로 나타내는 헤테로고리 화합물:Heterocyclic compounds represented by the formula (1):[화학식 1] [Formula 1]상기 화학식 1에 있어서, In Chemical Formula 1,X1 내지 X3은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CH이며X1 to X3 are the same as or different from each other, and each independently N or CHX1 내지 X3 중 어느 하나 이상은 N이고,At least one of X1 to X3 is N,R1은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 카복시기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고, R1 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxy group , Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted Heteroaryl group,Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,L은 직절결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,Y는 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고, Y is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,Z는 치환 또는 비치환된 아릴기이며,Z is a substituted or unsubstituted aryl group,L가 직접결합이고, Y가 치환 또는 비치환된 아릴기인 경우, Y와 Z는 상이하며, When L is a direct bond and Y is a substituted or unsubstituted aryl group, Y and Z are different,a는 0 내지 5의 정수이고,a is an integer from 0 to 5,상기 a가 복수일 때, 상기 R1은 서로 같거나 상이하다.When a is a plurality, R1 is the same as or different from each other.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 내지 4 중 어느 하나로 나타내는 헤테로고리 화합물:The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 4 below:[화학식 2][Formula 2][화학식 3][Formula 3][화학식 4][Formula 4]상기 화학식 2 내지 4에 있어서, 상기 X1 내지 X3, L, Y, Ar1, Ar2, R 및 a는 상기 화학식 1에서 정의한 바와 같고, In Chemical Formulas 2 to 4, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,R2 내지 R6은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 카보닐기, 치환 또는 비치환된 카복시기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴옥시기, 또는 치환 또는 비치환된 헤테로아릴기이고, R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group or substituted or unsubstituted heteroaryl group,b, d 및 f는 각각 0 내지 5의 정수이고,b, d and f are each an integer of 0 to 5,c 및 e는 각각 0 내지 4의 정수이고,c and e are each an integer of 0 to 4,상기 b가 복수일 때, 상기 R2는 서로 같거나 상이하고,When b is a plurality, R2 is the same as or different from each other,상기 c가 복수일 때, 상기 R3은 서로 같거나 상이하고,When c is a plurality, R3 is the same as or different from each other,상기 d가 복수일 때, 상기 R4는 서로 같거나 상이하고,When d is a plurality, R4 is the same as or different from each other,상기 e가 복수일 때, 상기 R5는 서로 같거나 상이하고,When e is plural, R5 is the same as or different from each other,상기 f가 복수일 때, 상기 R6은 서로 같거나 상이하다.When f is plural, R6 is the same as or different from each other.
- 청구항 1에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환의 아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 다환의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 단환의 헤테로아릴기 또는 치환 또는 비치환된 탄소수 3 내지 30의 다환의 헤테로아릴기인 것인 헤테로고리 화합물.The method according to claim 1, Ar1 and Ar2 are the same as or different from each other, each independently substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted polycyclic aryl group having 6 to 30 carbon atoms, substituted Or an unsubstituted monocyclic heteroaryl group having 3 to 30 carbon atoms or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms.
- 청구항 1에 있어서, 상기 L은 직접결합, 또는 탄소수 6 내지 30의 치환 또는 비치환된 아릴렌기인 것인 헤테로고리 화합물.The heterocyclic compound according to claim 1, wherein L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- 청구항 1에 있어서, 상기 Y는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 N, O, 및 S 중 어느 하나 이상을 포함하는 헤테로아릴기인 것인 헤테로고리 화합물.The method according to claim 1, wherein Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group including any one or more of N, O, and S having 3 to 30 carbon atoms.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나인 것인 헤테로고리 화합물:The heterocyclic compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:
- 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 또는 2층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 6 중 어느 한 항의 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound according to any one of claims 1 to 6. Phosphorescent organic light-emitting device.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 포함는 것인 유기 발광 소자.The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
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| CN114349742A (en) * | 2021-11-18 | 2022-04-15 | 上海和辉光电股份有限公司 | Organic electroluminescent compound containing phenanthrene and application thereof |
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