WO2020130553A1 - Organic compound and organic electroluminescent element using same - Google Patents
Organic compound and organic electroluminescent element using same Download PDFInfo
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- WO2020130553A1 WO2020130553A1 PCT/KR2019/017842 KR2019017842W WO2020130553A1 WO 2020130553 A1 WO2020130553 A1 WO 2020130553A1 KR 2019017842 W KR2019017842 W KR 2019017842W WO 2020130553 A1 WO2020130553 A1 WO 2020130553A1
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 377
- 238000000034 method Methods 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000011368 organic material Substances 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- -1 aryl phosphine oxide Chemical compound 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 20
- 239000007924 injection Substances 0.000 abstract description 20
- 238000004020 luminiscence type Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 489
- 238000003786 synthesis reaction Methods 0.000 description 489
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 131
- GLJMNHXRCJKURC-UHFFFAOYSA-N 2-bromophenanthridine Chemical compound C1=CC=C2C3=CC(Br)=CC=C3N=CC2=C1 GLJMNHXRCJKURC-UHFFFAOYSA-N 0.000 description 120
- 239000010410 layer Substances 0.000 description 68
- 238000002360 preparation method Methods 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000463 material Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- ABZIUHCROUGWRV-UHFFFAOYSA-N 3-bromophenanthridine Chemical compound C1=CC=C2C3=CC=C(Br)C=C3N=CC2=C1 ABZIUHCROUGWRV-UHFFFAOYSA-N 0.000 description 12
- OMHXBRAVEDGICZ-UHFFFAOYSA-N 6-bromobenzo[h]quinoline Chemical compound C1=CC=C2C(Br)=CC3=CC=CN=C3C2=C1 OMHXBRAVEDGICZ-UHFFFAOYSA-N 0.000 description 12
- GMWZNUNCVLSUGP-UHFFFAOYSA-N 6-bromophenanthridine Chemical compound C1=CC=C2C(Br)=NC3=CC=CC=C3C2=C1 GMWZNUNCVLSUGP-UHFFFAOYSA-N 0.000 description 12
- 0 Cc1nc(*)nc(*)c1 Chemical compound Cc1nc(*)nc(*)c1 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- DEPNUXJYUXKYKU-UHFFFAOYSA-N 5-bromobenzo[h]quinoline Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=N1 DEPNUXJYUXKYKU-UHFFFAOYSA-N 0.000 description 11
- KVGWEOSEQXPZQC-UHFFFAOYSA-N 9-bromobenzo[f]quinoline Chemical compound BrC=1C=CC2=C(C=3C=CC=NC=3C=C2)C=1 KVGWEOSEQXPZQC-UHFFFAOYSA-N 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- VPNLYKPIVSDMAS-UHFFFAOYSA-N 2-bromobenzo[f]quinoline Chemical compound C1=CC=C2C3=CC(Br)=CN=C3C=CC2=C1 VPNLYKPIVSDMAS-UHFFFAOYSA-N 0.000 description 10
- HEFNDUJWUYBIRX-UHFFFAOYSA-N 6-bromobenzo[f]quinoline Chemical compound BrC=1C2=C(C=3C=CC=NC=3C=1)C=CC=C2 HEFNDUJWUYBIRX-UHFFFAOYSA-N 0.000 description 10
- KIXJTAWBORIYDU-UHFFFAOYSA-N 8-bromophenanthridine Chemical compound BrC1=CC2=CN=C3C=CC=CC3=C2C=C1 KIXJTAWBORIYDU-UHFFFAOYSA-N 0.000 description 10
- QMYJMXHKRDLNJN-UHFFFAOYSA-N 9-bromobenzo[f]isoquinoline Chemical compound Brc1ccc2ccc3cnccc3c2c1 QMYJMXHKRDLNJN-UHFFFAOYSA-N 0.000 description 10
- UPXPFVMIDYWQKO-UHFFFAOYSA-N 9-bromobenzo[h]quinoline Chemical compound Brc1ccc2ccc3cccnc3c2c1 UPXPFVMIDYWQKO-UHFFFAOYSA-N 0.000 description 10
- YSDCPFDLZDQZLB-UHFFFAOYSA-N 9-bromophenanthridine Chemical compound BrC=1C=CC2=CN=C3C=CC=CC3=C2C=1 YSDCPFDLZDQZLB-UHFFFAOYSA-N 0.000 description 10
- 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 9
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 description 8
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-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
- 150000004982 aromatic amines Chemical class 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 2
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 2
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GTKMDPKQBVDGOY-UHFFFAOYSA-N C1=C(C=C2C(=C1Br)OC1=C2C=CC=C1)Cl Chemical compound C1=C(C=C2C(=C1Br)OC1=C2C=CC=C1)Cl GTKMDPKQBVDGOY-UHFFFAOYSA-N 0.000 description 2
- USUYEGAONPYNFJ-UHFFFAOYSA-N CC1(C)OB(c(cc2-c(cc3)ccc3-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)cc3c2[o]c2ccccc32)OC1(C)C Chemical compound CC1(C)OB(c(cc2-c(cc3)ccc3-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)cc3c2[o]c2ccccc32)OC1(C)C USUYEGAONPYNFJ-UHFFFAOYSA-N 0.000 description 2
- LLLCFLTXWZGPFS-UHFFFAOYSA-N CC1(C)OB(c(cc2-c3cccc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)cc3c2[o]c2ccccc32)OC1(C)C Chemical compound CC1(C)OB(c(cc2-c3cccc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)cc3c2[o]c2ccccc32)OC1(C)C LLLCFLTXWZGPFS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LWLSVNFEVKJDBZ-UHFFFAOYSA-N N-[4-(trifluoromethoxy)phenyl]-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methyl]piperidine-1-carboxamide Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1CCC(CC1)CC1=CC(=CC=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F LWLSVNFEVKJDBZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
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- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BCAIDIJUBGAHHN-UHFFFAOYSA-N CC1(C)OB(c(cc2-c3nc(-c4ccccc4)nc(-c(cc4)ccc4-c4ccccc4)c3)cc3c2[o]c2ccccc32)OC1(C)C Chemical compound CC1(C)OB(c(cc2-c3nc(-c4ccccc4)nc(-c(cc4)ccc4-c4ccccc4)c3)cc3c2[o]c2ccccc32)OC1(C)C BCAIDIJUBGAHHN-UHFFFAOYSA-N 0.000 description 1
- UQJINNCJXSFLRH-UHFFFAOYSA-N CC1(C)OB(c(cc2-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)cc3c2[s]c2ccccc32)OC1(C)C Chemical compound CC1(C)OB(c(cc2-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)cc3c2[s]c2ccccc32)OC1(C)C UQJINNCJXSFLRH-UHFFFAOYSA-N 0.000 description 1
- QJNFQXIFNBXMJK-UHFFFAOYSA-N CC1(C)OB(c(cc2-c3nc(C4=CCCC=C4)nc(-c4ccccc4)n3)cc3c2[s]c2ccccc32)OC1(C)C Chemical compound CC1(C)OB(c(cc2-c3nc(C4=CCCC=C4)nc(-c4ccccc4)n3)cc3c2[s]c2ccccc32)OC1(C)C QJNFQXIFNBXMJK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Definitions
- the present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, more specifically, a compound having excellent thermal stability, light-emitting ability, electron injection/transporting ability, and one or more organic material layers, thereby luminous efficiency and driving voltage. , It relates to an organic electroluminescent device having improved properties such as life.
- an organic electroluminescent device In an organic electroluminescent device (hereinafter referred to as an'organic EL device'), when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected hole meets the electron, an exciton is formed, and the exciton falls to the ground state to emit light.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
- NPB hole blocking layer
- BCP hole blocking layer
- Alq 3 and the like represented by the following formula
- anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials.
- metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have great advantages in terms of efficiency improvement, are blue, green, and red dopant materials.
- CBP has shown excellent properties as a phosphorescent host material.
- the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device. Therefore, development of an organic material layer material having excellent performance is required.
- An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and can be used as an electron transport layer material having excellent thermal stability, light emission performance, and electron injection and transport ability.
- Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
- X 1 to X 3 are the same as or different from each other, and each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and when CR 2 is plural, a plurality of R 2 s are the same or different from each other Different,
- Y is O or S
- Z 1 to Z 10 are the same or different from each other, and each independently is N or CR 3 , but at least one of Z 1 to Z 10 is N, and when CR 3 is plural, a plurality of R 3 s are the same or different from each other Different,
- a and b are each an integer from 1 to 3
- L 1 and L 2 are the same as or different from each other, and each independently a single bond or an arylene group of C 6 to C 60 ,
- Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,
- c is an integer from 0 to 4, wherein a plurality of R 3 are the same or different from each other,
- R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to alkynyl group of C 40, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 arylboronic group, C 6 ⁇ C 60 aryl phosphine group, and selected from the group consisting of C 6 ⁇ C 60 aryl phosphine oxide group
- the arylene groups of L 1 and L 2 , aryl groups and heteroaryl groups of Ar 1 and Ar 2 , alkyl groups of R 1 to R 3 , alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, deuterium, halogen, cyano group, Nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C Aryl group of 6 ⁇ C 60 , heteroaryl group of 5
- the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, at least among the one or more organic material layers
- an organic electroluminescent device comprising the compound represented by Chemical Formula 1.
- the compound of the present invention is excellent in thermal stability, luminescence, electron transport/injection, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
- FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
- FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.
- the present invention provides a novel compound that can be used as a high-efficiency electron transport layer material because of excellent thermal stability and electron injection/transport performance.
- the compound of Formula 1 according to the present invention is a core made of N-containing 6-membered heteroaromatic ring and N-containing aza phenanthrene ring attached directly or through a linker to one side of a dibenzoic moiety. ) Structure. Accordingly, since the compound of the present invention has a plate-like structure while having asymmetry based on the long axis of the molecule, it is excellent in thermal stability, luminescence, electron transport/injection, and the like. When the compound of Formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminous efficiency and current efficiency, and has a long life.
- the N-containing 6-membered heteroaromatic ring eg, triazine ring, pyrimidine ring, etc.
- EWG electron withdrawing group
- N-containing aza phenanthrene The ring is an electron withdrawing group (EWG).
- EWG electron withdrawing group
- These N-containing 6-membered heteroaromatic rings and N-containing aza phenanthrene rings are introduced at one side of the benzene moiety of the dibenzoic moiety.
- the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring may be introduced to each other in a meta position with respect to the dibenzoic moiety.
- the compound of the present invention has a plate-like structure to induce stacking between molecules, thus increasing electron mobility and thus having better electron transport properties.
- the interaction between the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring is minimized, and the physical and electrochemical stability of the compound itself can be increased.
- the compound of Formula 1 according to the present invention is also effective in inhibiting crystallization of the organic layer compared to a compound in which an N-containing 6-membered heteroaromatic ring and an N-containing azaphenanthrene ring are introduced at ortho or para positions with each other. There is, it is possible to significantly improve the durability and life characteristics of the organic electroluminescent device.
- an N-containing 6-membered heteroaromatic ring can be introduced (bonded) at position 6, which is the active site of the dibenzoic moiety.
- the stability of the molecule of the compound of the present invention may be increased, and steric hindrance of the compound may occur, and thus the passion stability may be significantly increased.
- the N-containing aza phenanthrene ring is introduced at the 8-position of the N-containing 6-membered heteroaromatic ring and the meta-position dibenzoic moiety, the synergistic effect of passion stability can be further exerted.
- the compounds of the present invention are structurally asymmetric.
- the asymmetry of these molecules suppresses crystallization, so that the processability of the compound according to the present invention and the durability of the device can be improved.
- an organic electroluminescent device having a low driving voltage, high efficiency, and long life compared to a conventional electron transport layer material (eg, Alq 3, etc.) can be manufactured.
- a full color display panel with improved high efficiency and long life characteristics can be manufactured.
- the compound represented by Formula 1 according to the present invention since the compound represented by Formula 1 according to the present invention has excellent electron transport/injection properties, it can be used as one of the electron transport layer and the electron injection layer, which is an organic material layer of the organic electroluminescent device, and is preferable. It can be used as an electron transport layer material. Accordingly, the compound represented by Formula 1 of the present invention may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer/injection layer material, an electron transport auxiliary layer material, more preferably an electron transport layer material.
- the organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve the performance and lifespan characteristics, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can also be maximized.
- Y introduced into the dibenzoic moiety may be O or S.
- Y introduced into the dibenzoic moiety may be O or S.
- L 1 and L 2 are The moieties may be coupled to each other in a meta position.
- the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring are dibenzoic moieties ( Moieties) are coupled to each other in a meta position on one side of the benzene site.
- the compound of the present invention since the compound of the present invention has a plate-like structure, by inducing stacking between molecules, electron mobility is increased and electron injection/transport performance is excellent.
- the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 2, but is not limited thereto.
- X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
- L 1 and L 2 are divalent linkers, which are the same or different from each other, and are each independently a single bond, or an arylene group of C 6 to C 60 .
- L 1 is an arylene group of C 6 ⁇ C 60
- L 2 may be a single bond, specifically L 1 is a phenylene group
- L 2 may be a single bond.
- the compound of Formula 1 according to the present invention may be a compound of Formula 3 or 4 below.
- X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
- Z 1 to Z 10 are the same as or different from each other, and each independently N or CR 3 , provided that at least one of Z 1 to Z 10 is N.
- one of Z 1 to Z 10 is N, and the other may be CR 3 ;
- two of Z 1 to Z 10 is N, and the other may be CR 3 .
- the CR 3 is plural, a plurality of R 3 s are the same as or different from each other.
- any one of Z 1 to Z 4 , Z 9 and Z 10 is CR 3 , and carbon (C) is bonded to L 2 , and in this case, R 3 is not present.
- any one of Z 1 , Z 3 and Z 10 is CR 3 and carbon (C) is bonded to L 2 , in which case R 3 is not present.
- the compound of Formula 1 according to the present invention may be a compound represented by any one of the following Formulas 5 to 7.
- X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
- X 1 to X 3 are the same or different from each other, and each independently is N or CR 2 , but at least one of X 1 to X 3 is N, and when CR 2 is plural, plural R 2 of the same or different from each other. Preferably, at least two of X 1 to X 3 may be N.
- the compound of Formula 1 when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, EWG properties are stronger and electron mobility is faster than that of a pyridine moiety. Accordingly, the compound of Formula 1 according to the present invention may have better electron transporting properties when the N-containing 6-membered heteroaromatic ring is a triazine moiety or pyrimidine moiety.
- the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 8 or 9.
- Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
- Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms.
- Ar 1 and Ar 2 are the same as or different from each other, and may each independently be a phenyl group or a biphenylene group.
- Ar 1 may be a phenyl group
- Ar 2 may be a phenyl group or a biphenyl group.
- the chemical stability of the compound according to the present invention can be improved.
- the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety
- their chemical stability is improved due to blocking of the phenyl group, thereby improving the chemical stability of the compound itself. It can be improved further.
- R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 Alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 hetero atoms
- Aryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group is selected from the group consisting of C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and
- Aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, Deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 3 nuclear atoms Heterocycloalkyl group of 40, C 6 ⁇ C 60 aryl group
- the compound represented by Chemical Formula 1 according to the present invention may be more specifically embodied as any one of the following Chemical Formulas 10 to 15.
- Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
- the compound represented by Chemical Formula 1 according to the present invention may be further embodied as any one of the following Chemical Formulas 16 to 27.
- Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
- the compounds represented by Formula 1 according to the present invention described above are the following exemplary compounds, such as compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D- 12, E-1 to E-12, F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12 It can be further specified as.
- the compound represented by Formula 1 according to the present invention is not limited by those illustrated below.
- alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
- alkenyl (alkenyl) means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
- vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like but is not limited thereto.
- alkynyl (alkynyl) means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.
- Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S Or a hetero atom such as Se.
- heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
- aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- two or more rings may be simply attached to each other (pendant) or a condensed form. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are simply attached to each other or condensed may be included, and condensed form with an aryl group may also be included.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole
- alkyloxy refers to a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
- R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
- Alkylsilyl in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl.
- arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
- alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
- aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms.
- alkylphosphinyl group means a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.
- arylphosphinyl group means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
- arylamine means an amine substituted with aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
- an organic electroluminescent device (hereinafter referred to as'organic EL device') comprising the compound represented by Chemical Formula 1 described above.
- the organic electroluminescent device includes an anode (anode), a cathode (cathode) and at least one organic material layer interposed between the anode and the cathode ( ⁇ ), at least one of the one or more organic material layers It includes a compound represented by the formula (1). At this time, the compound may be used alone, or may be used by mixing two or more.
- the organic material layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
- the electron transport layer includes a compound represented by Chemical Formula 1.
- the compound represented by Formula 1 is an electron transport layer material and is included in the organic electroluminescent device.
- electrons are easily injected from the cathode to the electron transport layer because of the compound of Formula 1, and can also quickly move from the electron transport layer to the light emitting layer, and thus the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
- the structure of the organic electroluminescent device of the present invention is not particularly limited, for example, on the substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (FIGS. 1 and 2). Reference).
- an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.
- the organic electroluminescent device as shown in Figure 1, on the substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and The cathode 200 may have a structure sequentially stacked.
- an electron injection layer may be positioned between the electron transport layer 340 and the cathode 200.
- the organic electroluminescent device of the present invention is a material and method known in the art, except that at least one of the organic material layer 300 (eg, the electron transport layer 340) includes a compound represented by Chemical Formula 1 It can be prepared by forming an organic layer and an electrode.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
- the substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
- examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb
- Conductive polymers such as polythiophene, poly(3-methylthiophene),
- examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer are not particularly limited, and a conventional material known in the art may be used.
- the target compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] using column chromatography (61.6 g, 80% yield).
- the target compound a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, synthesized in ⁇ Step 1>) 3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl 2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), and KOAc (27.9 g, 283.9 mmol) 1,4 -Dioxane was added to 500 ml, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A (52.9 g, yield 71%) was obtained using column chromatography.
- the target compound B [2,4] was prepared in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound b obtained in ⁇ Step 1> was used instead of the compound a used in Step 2 of Preparation Example 1 -diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1 ,3,5-triazine] (52.1 g, Overall yield 35%).
- the target compound c [2 was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound c obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1.
- 4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)- 1,3,5-triazine] (55.1 g, Overall yield 38%).
- the target compound D [2- was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound d obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1.
- ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall yield 40%).
- the target compound E was prepared in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound e obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1 [4- ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)pyrimidine] (53.2 g, Overall yield 37%).
- the target compound F [2 was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound f obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1 4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5 -triazine] (50.4 g, Overall yield 33%).
- the target compound I was prepared in the same manner as in ⁇ Step 2> of Preparative Example 6, except that Compound i obtained in ⁇ Step 1> was used instead of the compound f used in ⁇ Step 2> of Preparative Example 6 [2- ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall yield 36%).
- the target compound J was performed in the same manner as in ⁇ Step 2> of Preparation Example 6, except that the compound j obtained in ⁇ Step 1> was used instead of the compound f used in ⁇ Step 2> of Preparation Example 6 ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall yield 36%).
- Target compound A of preparation example 1 (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 28.5 mmol) )
- Toluene 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours.
- the organic layer was extracted with methylene chloride, and filtered using MgSO 4 .
- the target compound A-1 (4.1 g, yield 75%) was obtained using column chromatography.
- a target compound A-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-4 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-5 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-6 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-7 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-8 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-9 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-10 (3.4 g (yield 62%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound A-12 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 1, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
- a target compound B-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 13, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 13, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound B-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
- a target compound C-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 26, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-8 (3.5 g, yield 65%) was obtained by performing the same process as in Synthesis Example 26, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound C-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
- a target compound D-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-4 (3.6 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 37, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-6 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-7 (3.1 g (yield 58%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 37, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-9 (3.0 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound D-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
- a target compound E-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 49, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-3 (3.5 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 49, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-5 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-6 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-7 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-8 (3.4 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-9 (3.1 g, yield 58%) was obtained by performing the same process as in Synthesis Example 49, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound E-12 (3.2 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 49, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
- a target compound F-3 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-4 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-6 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-7 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-8 (3.4 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 61, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-9 (3.3 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-10 (3.2 g, yield 58%) was obtained by performing the same process as in Synthesis Example 61, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound F-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 61, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
- a target compound G-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 73, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-4 (3.6 g (yield 67%) was obtained by performing the same procedure as in Synthesis Example 73, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 73, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound G-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
- a target compound H-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 85, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 85, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound H-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
- a target compound I-2 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-3 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 97, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 97, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound I-12 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
- a target compound J-3 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 109, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-7 (3.8 g, yield 70%) was obtained by performing the same process as in Synthesis Example 109, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-10 (3.1 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- a target compound J-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
- the compound A-1 synthesized in the synthesis example was subjected to a high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.
- a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 ⁇ was washed with distilled water.
- ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed for 5 minutes using UV.
- the substrate was transferred to a vacuum evaporator.
- DS-205 Doosan Electronics, 80 nm
- NPB Doosan Electronics
- DS-405 Doosan Electronics(30 nm)/ Compound A-1 (30 nm) / LiF (1 nm) / Al (200 nm) was stacked in order to prepare an organic electroluminescent device.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 below was used instead of Compound A-1 used as the electron transport layer material in Example 1.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound A-1 used as the electron transport layer material in Example 1. At this time, the structures of Alq 3 used are as follows.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 used as the electron transport layer material in Example 1 was not used.
- the blue organic electroluminescent devices of Examples 1 to 120 using the compounds (A-1 to J-12) according to the present invention as electron transport layer materials were compared using Alq 3 , a conventional electron transport layer material. It was found that the blue organic electroluminescent device of Example 1 and the blue organic electroluminescent device of Comparative Example 2 without an electron transport layer showed better performance in terms of driving voltage, emission peak, and current efficiency.
Abstract
The present invention relates to a novel organic compound and an organic electroluminescent element comprising same, and more specifically, to an organic compound having excellent electron injection and transport ability, luminescence, and thermal stability, and an organic electroluminescent element which includes the compound, and thus has an improved luminous efficiency, driving voltage, lifespan, etc.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 열적 안정성, 발광능력, 전자 주입/수송 능력이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, more specifically, a compound having excellent thermal stability, light-emitting ability, electron injection/transporting ability, and one or more organic material layers, thereby luminous efficiency and driving voltage. , It relates to an organic electroluminescent device having improved properties such as life.
유기 전계 발광 소자(이하, '유기 EL 소자'라 함)는 두 전극에 전류, 또는 전압을 인가해 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어져 빛을 내게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In an organic electroluminescent device (hereinafter referred to as an'organic EL device'), when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected hole meets the electron, an exciton is formed, and the exciton falls to the ground state to emit light. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. To date, the hole injection layer and the hole transport layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq 3 and the like represented by the following formula are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials. Particularly, among the light emitting materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have great advantages in terms of efficiency improvement, are blue, green, and red dopant materials. Is being used as To date, CBP has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device. Therefore, development of an organic material layer material having excellent performance is required.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 열안정성, 발광능 및 전자 주입 및 수송능이 우수한 전자수송층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다. An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and can be used as an electron transport layer material having excellent thermal stability, light emission performance, and electron injection and transport ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by Formula 1:
(상기 화학식 1에서,(In the formula 1,
X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하며, X 1 to X 3 are the same as or different from each other, and each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and when CR 2 is plural, a plurality of R 2 s are the same or different from each other Different,
Y는 O 또는 S이고, Y is O or S,
Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 적어도 하나는 N이며, 이때 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 상이하며, Z 1 to Z 10 are the same or different from each other, and each independently is N or CR 3 , but at least one of Z 1 to Z 10 is N, and when CR 3 is plural, a plurality of R 3 s are the same or different from each other Different,
a 및 b는 각각 1 내지 3의 정수이고,a and b are each an integer from 1 to 3,
L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이며,L 1 and L 2 are the same as or different from each other, and each independently a single bond or an arylene group of C 6 to C 60 ,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,
c는 0 내지 4의 정수이고, 이때 복수의 R3는 서로 동일하거나 상이하며,c is an integer from 0 to 4, wherein a plurality of R 3 are the same or different from each other,
R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 arylboronic group, C 6 ~ C 60 aryl phosphine group, and selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,
상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene groups of L 1 and L 2 , aryl groups and heteroaryl groups of Ar 1 and Ar 2 , alkyl groups of R 1 to R 3 , alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, deuterium, halogen, cyano group, Nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C Aryl group of 6 ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C of the group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of the C 60 group And C 6 ~ C 60 is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, wherein when the plurality of substituents, they are the same or different from each other).
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.Further, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, at least among the one or more organic material layers One provides an organic electroluminescent device comprising the compound represented by Chemical Formula 1.
본 발명의 화합물은 열적 안정성, 발광능, 전자 수송/주입능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability, luminescence, electron transport/injection, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
도 1은 본 발명의 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
도 2는 본 발명의 다른 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.
** 부호의 설명 **** Explanation of sign **
100: 양극, 200: 음극,100: anode, 200: cathode,
300: 유기물층, 310: 정공주입층,300: organic layer, 310: hole injection layer,
320: 정공수송층, 330: 발광층,320: hole transport layer, 330: light emitting layer,
340: 전자수송층, 350: 전자주입층 340: electron transport layer, 350: electron injection layer
이하, 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail.
본 발명은 열안정성, 전자 주입/수송능이 우수하여 고효율 전자수송층 재료로 사용될 수 있는 신규 화합물을 제공한다. The present invention provides a novel compound that can be used as a high-efficiency electron transport layer material because of excellent thermal stability and electron injection/transport performance.
구체적으로, 본 발명에 따른 화학식 1의 화합물은 디벤조계 모이어티의 일측에 N-함유 6원 헤테로방향족환 및 N-함유 아자(aza) 페난트렌 환이 직접 또는 링커를 통해 결합되어 이루어진 코어(core) 구조를 포함한다. 이에 따라, 본 발명의 화합물은 분자의 장축을 기준으로 하여 비대칭성을 가지면서 판상형 구조를 갖기 때문에, 열적 안정성, 발광능, 전자 수송/주입능 등이 우수하다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자에 적용할 경우, 유기 전계 발광 소자는 낮은 구동전압과 높은 발광 효율 및 전류 효율을 가지며, 장수명을 갖는다. Specifically, the compound of Formula 1 according to the present invention is a core made of N-containing 6-membered heteroaromatic ring and N-containing aza phenanthrene ring attached directly or through a linker to one side of a dibenzoic moiety. ) Structure. Accordingly, since the compound of the present invention has a plate-like structure while having asymmetry based on the long axis of the molecule, it is excellent in thermal stability, luminescence, electron transport/injection, and the like. When the compound of Formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminous efficiency and current efficiency, and has a long life.
상기 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환(예, 트리아진 환, 피리미딘환 등)은 전자 흡수성이 큰 전자 끌개기(electron withdrawing group, EWG)이고, N-함유 아자 페난트렌 환은 전자 끌개기(electron withdrawing group, EWG)이다. 이러한 N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환은 디벤조계 모이어티의 일측 벤젠 부위에 도입된다. 이때, N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환은 디벤조계 모이어티에 대해 서로 메타(meta) 위치로 도입될 수 있다. 이 경우, 본 발명의 화합물은 판상형 구조를 이루어 분자 간의 스택킹(stacking)이 유도되고, 따라서 전자이동도가 증가되어 더 우수한 전자수송성을 가질 수 있다. 뿐만 아니라, 본 발명의 화합물은 N-함유 6원 헤테로방향족환과 N-함유 아자 페난트렌 환 간의 상호작용이 최소화되고, 화합물 자체의 물적, 전기화학적 안정성이 상승될 수 있다. 또한, 본 발명에 따른 화학식 1의 화합물은 N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환이 서로 오쏘(ortho)나 파라(para) 위치에 도입된 화합물에 비해 유기층의 결정화 억제에도 효과가 있어, 유기 전계 발광 소자의 내구성 및 수명 특성을 크게 향상시킬 수 있다.In the compound of Formula 1, the N-containing 6-membered heteroaromatic ring (eg, triazine ring, pyrimidine ring, etc.) is an electron withdrawing group (EWG) having high electron absorption, and N-containing aza phenanthrene The ring is an electron withdrawing group (EWG). These N-containing 6-membered heteroaromatic rings and N-containing aza phenanthrene rings are introduced at one side of the benzene moiety of the dibenzoic moiety. At this time, the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring may be introduced to each other in a meta position with respect to the dibenzoic moiety. In this case, the compound of the present invention has a plate-like structure to induce stacking between molecules, thus increasing electron mobility and thus having better electron transport properties. In addition, the interaction between the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring is minimized, and the physical and electrochemical stability of the compound itself can be increased. In addition, the compound of Formula 1 according to the present invention is also effective in inhibiting crystallization of the organic layer compared to a compound in which an N-containing 6-membered heteroaromatic ring and an N-containing azaphenanthrene ring are introduced at ortho or para positions with each other. There is, it is possible to significantly improve the durability and life characteristics of the organic electroluminescent device.
또한, N-함유 6원 헤테로방향족환이 디벤조계 모이어티의 활성 사이트(active site)인 6번 위치에 도입(결합)될 수 있다. 이 경우, 본 발명의 화합물은 분자의 안정성이 증가될 수 있고, 또 화합물의 입체장애(steric hindrance)가 발생하여 열정 안정성이 유의적으로 증가될 수 있다. 이와 함께, N-함유 아자 페난트렌 환이 N-함유 6원 헤테로방향족환과 메타 위치인 디벤조계 모이어티의 8번 위치에 도입될 경우, 열정 안정성의 상승 효과가 더 발휘될 수 있다.In addition, an N-containing 6-membered heteroaromatic ring can be introduced (bonded) at position 6, which is the active site of the dibenzoic moiety. In this case, the stability of the molecule of the compound of the present invention may be increased, and steric hindrance of the compound may occur, and thus the passion stability may be significantly increased. Along with this, when the N-containing aza phenanthrene ring is introduced at the 8-position of the N-containing 6-membered heteroaromatic ring and the meta-position dibenzoic moiety, the synergistic effect of passion stability can be further exerted.
게다가, 본 발명의 화합물은 구조적으로 비대칭성을 갖는다. 이러한 분자의 비대칭성은 결정화를 억제하여 본 발명에 따른 화합물의 공정성 및 소자의 내구성이 향상될 수 있다.Moreover, the compounds of the present invention are structurally asymmetric. The asymmetry of these molecules suppresses crystallization, so that the processability of the compound according to the present invention and the durability of the device can be improved.
특히, 본 발명의 화학식 1로 표시되는 화합물을 전자 수송층 재료로 사용시, 종래의 전자 수송층 재료(예, Alq3 등)에 비해 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 고효율 및 장수명 특성이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by Formula 1 of the present invention is used as an electron transport layer material, an organic electroluminescent device having a low driving voltage, high efficiency, and long life compared to a conventional electron transport layer material (eg, Alq 3, etc.) can be manufactured. In addition, a full color display panel with improved high efficiency and long life characteristics can be manufactured.
전술한 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물은 전자 수송/주입 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층인 전자 수송층 및 전자 주입층 중 어느 하나의 재료로 사용될 수 있으며, 바람직하게는 전자수송층 재료로 사용될 수 있다. 이에 따라, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 전자 수송층/주입층 재료, 전자수송 보조층 재료, 더 바람직하게는 전자 수송층 재료로 사용될 수 있다. 이러한 화학식 1의 화합물을 포함하는 본 발명의 유기 전계 발광소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.As described above, since the compound represented by Formula 1 according to the present invention has excellent electron transport/injection properties, it can be used as one of the electron transport layer and the electron injection layer, which is an organic material layer of the organic electroluminescent device, and is preferable. It can be used as an electron transport layer material. Accordingly, the compound represented by Formula 1 of the present invention may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer/injection layer material, an electron transport auxiliary layer material, more preferably an electron transport layer material. The organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve the performance and lifespan characteristics, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can also be maximized.
상기 화학식 1로 표시되는 화합물에서, 디벤조계 모이어티에 도입되는 Y는 O 또는 S일 수 있다. 일례로, 디벤조퓨란계(Y = O) 모이어티, 디벤조티오펜계(Y = S) 모이어티일 수 있다.In the compound represented by Chemical Formula 1, Y introduced into the dibenzoic moiety may be O or S. For example, it may be a dibenzofuran-based (Y = O) moiety, a dibenzothiophene-based (Y = S) moiety.
또, 상기 화학식 1에서, L1 및 L2는 
모이어티에 대해 서로 메타(meta) 위치로 결합될 수 있다. 이러한 L1 및 L2를 통해서 N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환이 디벤조계 모이어티(
모이어티)의 일측 벤젠 부위에 서로 메타 위치로 결합되게 된다. 이에 따라, 본 발명의 화합물은 판상형 구조를 갖기 때문에, 분자 간의 스택킹(stacking)이 유도됨으로써, 전자 이동도가 증가되어 전자 주입/수송능이 우수하다. 일례에 따르면, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 2로 표시되는 화합물 등일 수 있는데, 이에 한정되지 않는다.In addition, in Chemical Formula 1, L 1 and L 2 are The moieties may be coupled to each other in a meta position. Through these L 1 and L 2 , the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring are dibenzoic moieties ( Moieties) are coupled to each other in a meta position on one side of the benzene site. Accordingly, since the compound of the present invention has a plate-like structure, by inducing stacking between molecules, electron mobility is increased and electron injection/transport performance is excellent. According to an example, the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 2, but is not limited thereto.
상기 화학식 2에서,In Chemical Formula 2,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
또, 상기 화학식 1에서, L1 및 L2는 2가(divalent)의 연결기(linker)로서, 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이다. 예를 들어, 상기 화학식 1에서, L1은 C6~C60의 아릴렌기이고, L2는 단일결합일 수 있고, 구체적으로 L1은 페닐렌기이고, L2는 단일결합일 수 있다. 일례에 따르면, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 3 또는 4의 화합물일 수 있다.In addition, in Chemical Formula 1, L 1 and L 2 are divalent linkers, which are the same or different from each other, and are each independently a single bond, or an arylene group of C 6 to C 60 . For example, in Chemical Formula 1, L 1 is an arylene group of C 6 ~C 60 , L 2 may be a single bond, specifically L 1 is a phenylene group, and L 2 may be a single bond. According to an example, the compound of Formula 1 according to the present invention may be a compound of Formula 3 or 4 below.
상기 화학식 3 내지 4에서,In Chemical Formulas 3 to 4,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
또, 상기 화학식 1에서, Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 적어도 하나는 N이다. 바람직하게 Z1 내지 Z10 중에서 1개는 N이고, 나머지는 CR3일 수 있고; 또는 Z1 내지 Z10 중에서 2개는 N이고, 나머지는 CR3일 수 있다. 이때, 상기 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 또는 상이하다.Further, in Formula 1, Z 1 to Z 10 are the same as or different from each other, and each independently N or CR 3 , provided that at least one of Z 1 to Z 10 is N. Preferably, one of Z 1 to Z 10 is N, and the other may be CR 3 ; Or two of Z 1 to Z 10 is N, and the other may be CR 3 . In this case, when the CR 3 is plural, a plurality of R 3 s are the same as or different from each other.
다만, 상기 화학식 1에서, Z1 내지 Z4, Z9 및 Z10 중 어느 하나는 CR3로, 탄소(C)가 L2와 결합하고, 이 경우 R3는 존재하지 않는다. 바람직하게, Z1, Z3 및 Z10 중 어느 하나가 CR3로 탄소(C)가 L2와 결합하고, 이 경우 R3는 존재하지 않는다. 일례로, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 5 내지 7 중에서 어느 하나로 표시되는 화합물일 수 있다.However, in Chemical Formula 1, any one of Z 1 to Z 4 , Z 9 and Z 10 is CR 3 , and carbon (C) is bonded to L 2 , and in this case, R 3 is not present. Preferably, any one of Z 1 , Z 3 and Z 10 is CR 3 and carbon (C) is bonded to L 2 , in which case R 3 is not present. For example, the compound of Formula 1 according to the present invention may be a compound represented by any one of the following Formulas 5 to 7.
상기 화학식 5 내지 7에서,In the above formula 5 to 7,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
또, 상기 화학식 1에서, X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하다. 바람직하게 X1 내지 X3 중 적어도 2개는 N일 수 있다. 이와 같이, 상기 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티인 경우, 피리딘 모이어티인 경우에 비해 EWG 특성이 강하고, 전자 이동도도 더 빠르다. 따라서, 본 발명에 따른 화학식 1의 화합물은 N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티일 때 더 우수한 전자수송성을 가질 수 있다.In addition, in Chemical Formula 1, X 1 to X 3 are the same or different from each other, and each independently is N or CR 2 , but at least one of X 1 to X 3 is N, and when CR 2 is plural, plural R 2 of the same or different from each other. Preferably, at least two of X 1 to X 3 may be N. As described above, in the compound of Formula 1, when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, EWG properties are stronger and electron mobility is faster than that of a pyridine moiety. Accordingly, the compound of Formula 1 according to the present invention may have better electron transporting properties when the N-containing 6-membered heteroaromatic ring is a triazine moiety or pyrimidine moiety.
일례로, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 8 또는 9로 표시되는 화합물일 수 있다.For example, the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 8 or 9.
상기 화학식 8 및 9에서,In Chemical Formulas 8 and 9,
Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
또, 상기 화학식 1에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된다. 바람직하게, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 비페닐기(biphenylene group)일 수 있다. 예컨대, Ar1은 페닐기이고, Ar2는 페닐기 또는 비페닐기일 수 있다. 이 경우, 본 발명에 따른 화합물의 화학적 안정성이 향상될 수 있다. 특히, 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티인 경우, 이들의 화학적 안정성이 페닐기의 블록킹(blocking)으로 인해 향상됨으로써, 화합물 자체의 화학적 안정성이 더 향상될 수 있다.In addition, in Chemical Formula 1, Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms. Preferably, Ar 1 and Ar 2 are the same as or different from each other, and may each independently be a phenyl group or a biphenylene group. For example, Ar 1 may be a phenyl group, and Ar 2 may be a phenyl group or a biphenyl group. In this case, the chemical stability of the compound according to the present invention can be improved. In particular, in the compound of Formula 1, when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, their chemical stability is improved due to blocking of the phenyl group, thereby improving the chemical stability of the compound itself. It can be improved further.
또, 상기 화학식 1에서, 
은 하기 치환체 S1 내지 S19로 이루어진 군에서 선택된 치환체일 수 있는데, 이에 한정되지 않는다.In addition, in Chemical Formula 1, May be a substituent selected from the group consisting of the following substituents S1 to S19, but is not limited thereto.
또, 상기 화학식 1에서, R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며, 바람직하게 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기(더 바람직하게 C1~C12의 알킬기), C6~C60의 아릴기(더 바람직하게, C6~C20의 아릴기) 및 핵원자수 5 내지 60의 헤테로아릴기(더 바람직하게, 핵원자수 5 내지 20의 헤테로아릴기)로 이루어진 군에서 선택될 수 있다. 이때, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함한다.In addition, in Chemical Formula 1, R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 Alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 hetero atoms Aryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, is selected from the group consisting of C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ with an aryl amine of the C 60 of, Preferably hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group (more preferably C 1 ~ C 12 alkyl group), C 6 ~ C 60 aryl group (more preferably, C 6 ~ C 20 aryl group) and a heteroaryl group having 5 to 60 nuclear atoms (more preferably, a heteroaryl group having 5 to 20 nuclear atoms). In this case, the heterocycloalkyl group and the heteroaryl group each include one or more heteroatoms selected from the group consisting of N, S, O and Se.
또, 상기 화학식 1에서, 상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 바람직하게 중수소, 할로겐, 시아노기, 니트로기, C1~C20의 알킬기, C6~C30의 아릴기, 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환될 수 있다. 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다.In addition, in Chemical Formula 1, the arylene groups of L 1 and L 2 , aryl groups and heteroaryl groups of Ar 1 and Ar 2 , alkyl groups of R 1 to R 3 , alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups , Aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, Deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 3 nuclear atoms Heterocycloalkyl group of 40, C 6 ~ C 60 aryl group, Heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 aryl force of the pin-oxide group and a C 6 ~ C to 1 substituent at least one selected from the 60 group consisting of aryl amines, and substituted or unsubstituted, preferably deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 20 It may be unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl groups, C 6 to C 30 aryl groups, and 5 to 30 heteroaryl groups. At this time, when the plurality of substituents, the plurality of substituents are the same or different from each other.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 10 내지 15 중 어느 하나로 보다 구체화될 수 있다.The compound represented by Chemical Formula 1 according to the present invention may be more specifically embodied as any one of the following Chemical Formulas 10 to 15.
상기 화학식 10 내지 15에서,In Chemical Formulas 10 to 15,
Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 16 내지 27 중 어느 하나로 더 구체화될 수 있다.The compound represented by Chemical Formula 1 according to the present invention may be further embodied as any one of the following Chemical Formulas 16 to 27.
상기 화학식 16 내지 27에서,In Chemical Formulas 16 to 27,
Y, Z1 내지 Z10, c, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
이상에서 설명한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 예시 화합물, 예컨대 화합물 A-1 내지 A-12, B-1 내지 B-12, C-1 내지 C-12, D-1 내지 D-12, E-1 내지 E-12, F-1 내지 F-12, G-1 내지 G-12, H-1 내지 H-12, I-1 내지 I-12, 및 J-1 내지 J-12로 보다 구체화될 수 있다. 그러나 본 발명에 따른 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compounds represented by Formula 1 according to the present invention described above are the following exemplary compounds, such as compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D- 12, E-1 to E-12, F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12 It can be further specified as. However, the compound represented by Formula 1 according to the present invention is not limited by those illustrated below.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkenyl (alkenyl)" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples of the vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
본 발명에서"알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkynyl (alkynyl)" means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지는 않는다."Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or a condensed form. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지는 않는다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and condensed form with an aryl group may also be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, 모노-뿐만 아니라 디-, 트리-알킬실릴을 포함한다. 또, "아릴실릴"은 탄소수 5 내지 60의 아릴로 치환된 실릴을 의미하고, 모노-뿐만 아니라 디-, 트리-아릴실릴 등의 폴리아릴실릴을 포함한다."Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl. Moreover, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
본 발명에서 "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미한다.In the present invention, "alkyl boron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron group" means a boron group substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "알킬포스피닐기"는 탄소수 1 내지 40의 알킬로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-알킬포스피닐기를 포함한다. 또, 본 발명에서 "아릴포스피닐기"는 탄소수 6 내지 60의 모노아릴 또는 디아릴로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-아릴포스피닐기를 포함한다. In the present invention, "alkylphosphinyl group" means a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, in the present invention, "arylphosphinyl group" means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-아릴아민를 포함한다.In the present invention, "arylamine" means an amine substituted with aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
<유기 전계 발광 소자><Organic electroluminescent device>
한편, 본 발명의 다른 측면은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(이하, '유기 EL 소자')에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (hereinafter referred to as'organic EL device') comprising the compound represented by Chemical Formula 1 described above.
구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device according to the present invention includes an anode (anode), a cathode (cathode) and at least one organic material layer interposed between the anode and the cathode (介在), at least one of the one or more organic material layers It includes a compound represented by the formula (1). At this time, the compound may be used alone, or may be used by mixing two or more.
일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층, 및 전자주입층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송층 물질로 유기 전계 발광 소자에 포함된다. 이러한 유기 전계 발광 소자에서, 전자는 화학식 1의 화합물 때문에, 음극에서 전자수송층으로 용이하게 주입되고, 또한 전자수송층에서 발광층으로 빠르게 이동할 수 있고, 따라서 발광층에서의 정공과 전자의 결합력이 높다. 그러므로, 본 발명의 유기 전계 발광 소자는 발광효율, 전력효율, 휘도 등이 우수하다. According to an example, the organic material layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the electron transport layer includes a compound represented by Chemical Formula 1. At this time, the compound represented by Formula 1 is an electron transport layer material and is included in the organic electroluminescent device. In such an organic electroluminescent device, electrons are easily injected from the cathode to the electron transport layer because of the compound of Formula 1, and can also quickly move from the electron transport layer to the light emitting layer, and thus the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 예컨대 기판 위에, 양극(100), 1층 이상의 유기물층(300) 및 음극(200)이 순차적으로 적층될 수 있다(도 1 및 도 2 참조). 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, for example, on the substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (FIGS. 1 and 2). Reference). In addition, an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.
일례에 따르면, 상기 유기 전계 발광 소자는 도 1에 도시된 바와 같이, 기판 위에, 양극(100), 정공주입층(310), 정공수송층(320), 발광층(330), 전자수송층(340) 및 음극(200)이 순차적으로 적층된 구조를 가질 수 있다. 선택적으로, 도 2에 도시된 바와 같이, 상기 전자수송층(340)과 음극(200) 사이에 전자주입층이 위치할 수 있다. 본 발명의 유기 전계 발광 소자는 상기 유기물층(300) 중 적어도 하나[예컨대, 전자수송층(340)]가 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.According to an example, the organic electroluminescent device, as shown in Figure 1, on the substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and The cathode 200 may have a structure sequentially stacked. Optionally, as illustrated in FIG. 2, an electron injection layer may be positioned between the electron transport layer 340 and the cathode 200. The organic electroluminescent device of the present invention is a material and method known in the art, except that at least one of the organic material layer 300 (eg, the electron transport layer 340) includes a compound represented by Chemical Formula 1 It can be prepared by forming an organic layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
본 발명에서 사용 가능한 기판은 특별히 한정되지 않으며, 비제한적인 예로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 있다.The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
또, 양극 물질의 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지는 않는다.Further, examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
또, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지는 않는다.Further, examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
또한, 정공주입층, 정공수송층, 발광층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer are not particularly limited, and a conventional material known in the art may be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, the present invention is not limited by the following examples.
[준비예 1] 화합물 A의 합성[Preparation Example 1] Synthesis of Compound A
<단계 1> 화합물 a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine]의 합성<Step 1> Synthesis of compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine]
4-bromo-2-chlorodibenzo[b,d]furan (50 g, 177.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (47.6 g, 177.6 mmol), Pd(PPh3)4 (10.3 g, 8.9 mmol), 및 K2CO3 (73.6 g, 532.8 mmol)을 Toluene 500ml, EtOH 100ml 및 H2O 100ml에 넣고, 12시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] (61.6 g, 수율 80 %)를 얻었다. 4-bromo-2-chlorodibenzo[b,d]furan (50 g, 177.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (47.6 g, 177.6 mmol), Pd(PPh 3 ) 4 (10.3 g, 8.9 mmol), and K 2 CO 3 (73.6 g, 532.8 mmol) were added to 500 ml of Toluene, 100 ml of EtOH and 100 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] using column chromatography (61.6 g, 80% yield).
[LCMS]: 434[LCMS]: 434
<단계 2> 화합물 A [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]의 합성<Step 2> Compound A [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4 -yl)-1,3,5-triazine]
상기 <단계 1>에서 합성된 목적 화합물 a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), 및 KOAc (27.9 g, 283.9 mmol)을 1,4-Dioxane 500ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 A (52.9 g, 수율 71 %)을 얻었다. The target compound a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, synthesized in <Step 1>) 3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl 2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), and KOAc (27.9 g, 283.9 mmol) 1,4 -Dioxane was added to 500 ml, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A (52.9 g, yield 71%) was obtained using column chromatography.
1H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39 (t, 1H), 7.48-7.50 (m, 6H), 7.54 (d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.98 (d, 1H), 8.34-8.38 (m, 4H) 1 H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39 (t, 1H), 7.48-7.50 (m, 6H), 7.54 (d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.98 (d, 1H), 8.34-8.38 (m, 4H)
[LCMS]: 526[LCMS]: 526
[준비예 2] 화합물 B의 합성[Preparation Example 2] Synthesis of Compound B
<단계 1> 화합물 b의 합성<Step 1> Synthesis of compound b
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 b를 얻었다.2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1. A target compound b was obtained by performing the same method as in <Step 1> of Preparation Example 1, except that the compound was used.
<단계 2> 화합물 B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Compound B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d] synthesis of furan-4-yl)phenyl)-1,3,5-triazine]
준비예 1의 <단계 2에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 b를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (52.1 g, Overall 수율 35%)을 얻었다.The target compound B [2,4] was prepared in the same manner as in <Step 2> of Preparation Example 1, except that the compound b obtained in <Step 1> was used instead of the compound a used in Step 2 of Preparation Example 1 -diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1 ,3,5-triazine] (52.1 g, Overall yield 35%).
1H-NMR: δ 1.19 (s, 12H), 7.31 (d, 1H), 7.39 (t, 1H), 7.54 (d, 1H), 7.49-7.50 (m, 6H), 7.61 (d, 1H), 7.73(t, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.94 (s, 1H), 7.98 (d, 1H), 8.36-8.38 (m, 5H) 1 H-NMR: δ 1.19 (s, 12H), 7.31 (d, 1H), 7.39 (t, 1H), 7.54 (d, 1H), 7.49-7.50 (m, 6H), 7.61 (d, 1H), 7.73(t, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.94 (s, 1H), 7.98 (d, 1H), 8.36-8.38 (m, 5H)
[LCMS] : 602[LCMS]: 602
[준비예 3] 화합물 C 의 합성[Preparation Example 3] Synthesis of Compound C
<단계 1> 화합물 c의 합성<Step 1> Synthesis of compound c
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 c를 얻었다.2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1. The target compound c was obtained in the same manner as in <Step 1> of Preparation Example 1, except that was used.
<단계 2> 화합물 C [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Compound C [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d] synthesis of furan-4-yl)phenyl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 c를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 c [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (55.1 g, Overall 수율 38%)을 얻었다.The target compound c [2, was performed in the same manner as in <Step 2> of Preparation Example 1, except that the compound c obtained in <Step 1> was used instead of the compound a used in <Step 2> of Preparation Example 1. 4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)- 1,3,5-triazine] (55.1 g, Overall yield 38%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39 (t, 1H), 7.25 (d, 2H), 7.50-7.52 (m, 6H), 7.54(d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.37 (d, 4H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39 (t, 1H), 7.25 (d, 2H), 7.50-7.52 (m, 6H), 7.54(d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.37 (d, 4H)
[LCMS]: 602[LCMS]: 602
[준비예 4] 화합물 D의 합성[Preparation Example 4] Synthesis of Compound D
<단계 1> 화합물 d의 합성<Step 1> Synthesis of compound d
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 d를 얻었다.2-([1,1'-biphenyl]-4-yl)-4-chloro- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1. Except that 6-phenyl-1,3,5-triazine was used, it was performed in the same manner as in <Step 1> of Preparation Example 1 to obtain the target compound d.
<단계 2> 화합물 D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]의 합성<Step 2> Compound D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2- Synthesis of dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 d를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall 수율 40%)을 얻었다.The target compound D [2- was performed in the same manner as in <Step 2> of Preparation Example 1, except that the compound d obtained in <Step 1> was used instead of the compound a used in <Step 2> of Preparation Example 1. ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall yield 40%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.36 (d, 2H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H) ), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.36 (d, 2H)
[LCMS]: 602[LCMS]: 602
[준비예 5] 화합물 E의 합성[Preparation Example 5] Synthesis of Compound E
<단계 1> 화합물 e의 합성<Step 1> Synthesis of Compound e
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidin을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 e를 얻었다.4-([1,1'-biphenyl]-4-yl)-6-chloro- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1. Except that 2-phenylpyrimidin was used, it was performed in the same manner as in <Step 1> of Preparation Example 1 to obtain the target compound e.
<단계 2> 화합물 E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine]의 합성<Step 2> Compound E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2- Synthesis of dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 e를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine] (53.2 g, Overall 수율 37%)을 얻었다.The target compound E was prepared in the same manner as in <Step 2> of Preparation Example 1, except that the compound e obtained in <Step 1> was used instead of the compound a used in <Step 2> of Preparation Example 1 [4- ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)pyrimidine] (53.2 g, Overall yield 37%).
1H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.85 (d, 2H), 7.98 (d, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H) 1 H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75 (d, 2H) ), 7.76 (s, 1H), 7.82 (s, 1H), 7.85 (d, 2H), 7.98 (d, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H)
[LCMS]: 601[LCMS]: 601
[준비예 6] 화합물 F의 합성[Preparation Example 6] Synthesis of Compound F
<단계 1> 화합물 f의 합성<Step 1> Synthesis of compound f
준비예 1의 <단계 1>에서 사용된 4-bromo-2-chlorodibenzo[b,d]furan 대신 4-bromo-2-chlorodibenzo[b,d]thiophene을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 f를 얻었다.<Except for using 4-bromo-2-chlorodibenzo[b,d]thiophene instead of 4-bromo-2-chlorodibenzo[b,d]furan used in <Step 1> of Preparation Example 1, < The same procedure as in Step 1> was performed to obtain the target compound f.
<단계 2> 화합물 F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]의 합성<Step 2> Compound F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4 -yl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 f를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (50.4 g, Overall 수율 33%)을 얻었다.The target compound F [2, was performed in the same manner as in <Step 2> of Preparation Example 1, except that the compound f obtained in <Step 1> was used instead of the compound a used in <Step 2> of Preparation Example 1 4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5 -triazine] (50.4 g, Overall yield 33%).
1H-NMR: δ 1.20 (s, 12H), 7.48-7.49 (m, 6H), 7.50 (t, 1H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.48-7.49 (m, 6H), 7.50 (t, 1H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H)
[LCMS]: 542[LCMS]: 542
[준비예 7] 화합물 G의 합성[Preparation Example 7] Synthesis of Compound G
<단계 1> 화합물 g의 합성<Step 1> Synthesis of compound g
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 g를 얻었다.2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6. A target compound g was obtained by performing the same procedure as in <Step 1> of Preparation Example 1, except that was used.
<단계 2> 화합물 G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Compound G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d] Synthesis of thiophen-4-yl)phenyl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 g를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (54.4 g, Overall 수율 35%)을 얻었다.Except for using the compound g obtained in <Step 1> instead of the compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 to obtain the target compound G [2, 4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)- 1,3,5-triazine] (54.4 g, Overall yield 35%).
1H-NMR: δ 1.20 (s, 12H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.61(d, 1H), 7.73 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.94 (s, 1H), 8.01 (s, 1H), 8.36-8.38 (m, 5H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.61 (d, 1H), 7.73 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.94 (s, 1H), 8.01 (s, 1H), 8.36-8.38 (m, 5H), 8.45 (d, 1H)
[LCMS] : 618[LCMS]: 618
[준비예 8] 화합물 H의 합성[Preparation Example 8] Synthesis of Compound H
<단계 1> 화합물 h의 합성<Step 1> Synthesis of compound h
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 h를 얻었다.2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6. The target compound h was obtained in the same manner as in <Step 1> of Preparation Example 1, except that was used.
<단계 2> 화합물 H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Compound H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d] Synthesis of thiophen-4-yl)phenyl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 h를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (53.0 g, Overall 수율 32%)을 얻었다.Except for using the compound h obtained in the above <Step 1> instead of the compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 to obtain the target compound H [2, 4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)- 1,3,5-triazine] (53.0 g, Overall yield 32%).
1H-NMR: δ 1.20 (s, 12H), 7.23 (d, 2H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.23 (d, 2H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H)
[LCMS]: 618[LCMS]: 618
[준비예 9] 화합물 I의 합성[Preparation Example 9] Synthesis of Compound I
<단계 1> 화합물 i의 합성<Step 1> Synthesis of Compound i
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 i를 얻었다.2-([1,1'-biphenyl]-4-yl)-4-chloro- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6. Except that 6-phenyl-1,3,5-triazine was used, it was performed in the same manner as in <Step 1> of Preparation Example 1 to obtain the target compound i.
<단계 2> 화합물 I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]의 합성<Step 2> Compound I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2- Synthesis of dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 i를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall 수율 36%)을 얻었다.The target compound I was prepared in the same manner as in <Step 2> of Preparative Example 6, except that Compound i obtained in <Step 1> was used instead of the compound f used in <Step 2> of Preparative Example 6 [2- ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall yield 36%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 2H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 2H), 8.45 (d, 1H)
[LCMS]: 618 [LCMS]: 618
[준비예 10] 화합물 J의 합성[Preparation Example 10] Synthesis of Compound J
<단계 1> 화합물 j의 합성<Step 1> Synthesis of compound j
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 j를 얻었다.4-([1,1'-biphenyl]-4-yl)-6-chloro- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6. Except that 2-phenylpyrimidine was used, it was performed in the same manner as in <Step 1> of Preparation Example 1 to obtain the target compound j.
<단계 2> 화합물 J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine]의 합성<Step 2> Compound J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2- Synthesis of dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 j를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall 수율 36%)을 얻었다.The target compound J was performed in the same manner as in <Step 2> of Preparation Example 6, except that the compound j obtained in <Step 1> was used instead of the compound f used in <Step 2> of Preparation Example 6 ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall yield 36%).
1H-NMR: δ 1.20 (s, 12H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.85 (d, 2H), 7.93 (d, 1H), 8.01 (s, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.85 (d, 2H), 7.93 (d, 1H), 8.01 (s, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H), 8.45 (d, 1H)
[LCMS]: 617[LCMS]: 617
[합성예 1] 화합물 A-1의 합성[Synthesis Example 1] Synthesis of Compound A-1
준비예 1의 목적 화합물 A (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 28.5 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 A-1 (4.1 g, 수율 75 %)을 얻었다.Target compound A of preparation example 1 (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 28.5 mmol) ) Into 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A-1 (4.1 g, yield 75%) was obtained using column chromatography.
[LCMS]: 577[LCMS]: 577
[합성예 2] 화합물 A-2의 합성[Synthesis Example 2] Synthesis of Compound A-2
합성예 1에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-2 (3.9 g, 수율 72%)을 얻었다.A target compound A-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 3] 화합물 A-3의 합성[Synthesis Example 3] Synthesis of Compound A-3
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-3 (3.8 g, 수율 70%)을 얻었다.A target compound A-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 4] 화합물 A-4의 합성[Synthesis Example 4] Synthesis of Compound A-4
합성예 1에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-4 (3.5 g, 수율 65%)을 얻었다.A target compound A-4 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 5] 화합물 A-5의 합성[Synthesis Example 5] Synthesis of Compound A-5
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-5 (3.5 g, 수율 65%)을 얻었다.A target compound A-5 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 6] 화합물 A-6의 합성[Synthesis Example 6] Synthesis of Compound A-6
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-6 (3.9 g, 수율 72%)을 얻었다.A target compound A-6 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 7] 화합물 A-7의 합성[Synthesis Example 7] Synthesis of Compound A-7
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-7 (3.7 g, 수율 67%)을 얻었다.A target compound A-7 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 8] 화합물 A-8의 합성[Synthesis Example 8] Synthesis of Compound A-8
합성예 1에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-8 (3.7 g, 수율 67%)을 얻었다.A target compound A-8 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 9] 화합물 A-9의 합성[Synthesis Example 9] Synthesis of Compound A-9
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-9 (3.4 g, 수율 62%)을 얻었다.A target compound A-9 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 10] 화합물 A-10의 합성[Synthesis Example 10] Synthesis of Compound A-10
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-10 (3.4 g (수율 62%)을 얻었다.A target compound A-10 (3.4 g (yield 62%)) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 11] 화합물 A-11의 합성[Synthesis Example 11] Synthesis of Compound A-11
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-11 (3.3 g, 수율 60%)을 얻었다.A target compound A-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS]: 577[LCMS]: 577
[합성예 12] 화합물 A-12의 합성[Synthesis Example 12] Synthesis of Compound A-12
합성예 1에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-12 (3.3 g, 수율 61%)을 얻었다.A target compound A-12 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 1, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
[LCMS] : 577[LCMS]: 577
[합성예 13] 화합물 B-1의 합성[Synthesis Example 13] Synthesis of Compound B-1
준비예 2에서 합성된 화합물 B (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol) 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 B-1 (3.8 g, 수율 70 %)을 얻었다.Compound B (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.5 g, 24.9) synthesized in Preparation Example 2 mmol) was put in 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound B-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 653[LCMS]: 653
[합성예 14] 화합물 B-2의 합성[Synthesis Example 14] Synthesis of Compound B-2
합성예 13에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-2 (3.9 g, 수율 72%)을 얻었다.A target compound B-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 13, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS]: 653[LCMS]: 653
[합성예 15] 화합물 B-3의 합성[Synthesis Example 15] Synthesis of Compound B-3
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-3 (3.9 g, 수율 73%)을 얻었다.A target compound B-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS]: 653[LCMS]: 653
[합성예 16] 화합물 B-4의 합성[Synthesis Example 16] Synthesis of Compound B-4
합성예 13에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-4 (3.9 g, 수율 73%)을 얻었다.A target compound B-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS]: 653[LCMS]: 653
[합성예 17] 화합물 B-5의 합성[Synthesis Example 17] Synthesis of Compound B-5
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-5 (3.8 g, 수율 70%)을 얻었다.A target compound B-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS]: 653[LCMS]: 653
[합성예 18] 화합물 B-6의 합성[Synthesis Example 18] Synthesis of Compound B-6
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-6 (3.7 g, 수율 68%)을 얻었다.A target compound B-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 19] 화합물 B-7의 합성[Synthesis Example 19] Synthesis of Compound B-7
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-7 (3.7 g, 수율 68%)을 얻었다.A target compound B-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 20] 화합물 B-8의 합성[Synthesis Example 20] Synthesis of Compound B-8
합성예 13에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-8 (3.5 g, 수율 65%)을 얻었다.A target compound B-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 13, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 21] 화합물 B-9의 합성[Synthesis Example 21] Synthesis of Compound B-9
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-9 (3.3 g, 수율 60%)을 얻었다.A target compound B-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 22] 화합물 B-10의 합성[Synthesis Example 22] Synthesis of Compound B-10
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-10 (3.1 g, 수율 57%)을 얻었다.A target compound B-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 23] 화합물 B-11의 합성[Synthesis Example 23] Synthesis of Compound B-11
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-11 (3.2 g, 수율 59%)을 얻었다.A target compound B-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 24] 화합물 B-12의 합성[Synthesis Example 24] Synthesis of Compound B-12
합성예 13에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-12 (3.2 g, 수율 59%)을 얻었다.A target compound B-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
[LCMS] : 653[LCMS]: 653
[합성예 25] 화합물 C-1의 합성[Synthesis Example 25] Synthesis of Compound C-1
준비예 3에서 합성된 화합물 C (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol) 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 C-1 (3.9 g, 수율 72 %)을 얻었다.Compound C (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.5 g, 24.9) synthesized in Preparation Example 3 mmol) was put in 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound C-1 (3.9 g, yield 72%) was obtained using column chromatography.
[LCMS] : 653[LCMS]: 653
[합성예 26] 화합물 C-2의 합성[Synthesis Example 26] Synthesis of Compound C-2
합성예 26에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-2 (3.9 g, 수율 72%)을 얻었다.A target compound C-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 26, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 27] 화합물 C-3의 합성[Synthesis Example 27] Synthesis of Compound C-3
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-3 (3.9 g, 수율 73%)을 얻었다.A target compound C-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 28] 화합물 C-4의 합성[Synthesis Example 28] Synthesis of Compound C-4
합성예 26에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-4 (3.9 g, 수율 73%)을 얻었다.A target compound C-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS]: 653[LCMS]: 653
[합성예 29] 화합물 C-5의 합성[Synthesis Example 29] Synthesis of Compound C-5
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-5 (3.8 g, 수율 70%)을 얻었다.A target compound C-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 30] 화합물 C-6의 합성[Synthesis Example 30] Synthesis of Compound C-6
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-6 (3.7 g, 수율 68%)을 얻었다.A target compound C-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 31] 화합물 C-7의 합성[Synthesis Example 31] Synthesis of Compound C-7
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-7 (3.7 g, 수율 68%)을 얻었다.A target compound C-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 32] 화합물 C-8의 합성[Synthesis Example 32] Synthesis of Compound C-8
합성예 26에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-8 (3.5 g, 수율 65%)을 얻었다.A target compound C-8 (3.5 g, yield 65%) was obtained by performing the same process as in Synthesis Example 26, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 33] 화합물 C-9의 합성[Synthesis Example 33] Synthesis of Compound C-9
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-9 (3.3 g, 수율 60%)을 얻었다.A target compound C-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 34] 화합물 C-10의 합성[Synthesis Example 34] Synthesis of Compound C-10
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-10 (3.1 g, 수율 57%)을 얻었다.A target compound C-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 35] 화합물 C-11의 합성[Synthesis Example 35] Synthesis of Compound C-11
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-11 (3.2 g, 수율 59%)을 얻었다.A target compound C-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 36] 화합물 C-12의 합성[Synthesis Example 36] Synthesis of Compound C-12
합성예 26에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-12 (3.2 g, 수율 59%)을 얻었다.A target compound C-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
[LCMS] : 653[LCMS]: 653
[합성예 37] 화합물 D-1의 합성[Synthesis Example 37] Synthesis of Compound D-1
준비예 4에서 합성된 화합물 D (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 D-1 (3.8 g, 수율 70 %)을 얻었다.Compound D (5 g, 8.3 mmol) synthesized in Preparation Example 4, 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) was added to 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound D-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 653[LCMS]: 653
[합성예 38] 화합물 D-2의 합성[Synthesis Example 38] Synthesis of Compound D-2
합성예 37에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-2 (3.9 g, 수율 72%)을 얻었다.Except for using 3-bromophenanthridine instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was performed to obtain the target compound D-2 (3.9 g, yield 72%).
[LCMS] : 653[LCMS]: 653
[합성예 39] 화합물 D-3의 합성[Synthesis Example 39] Synthesis of Compound D-3
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-3 (3.8 g, 수율 70%)을 얻었다.A target compound D-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 40] 화합물 D-4의 합성[Synthesis Example 40] Synthesis of Compound D-4
합성예 37에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-4 (3.6 g, 수율 66%)을 얻었다.A target compound D-4 (3.6 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 37, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 41] 화합물 D-5의 합성[Synthesis Example 41] Synthesis of Compound D-5
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-5 (3.8 g, 수율 70%)을 얻었다.A target compound D-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 42] 화합물 D-6의 합성[Synthesis Example 42] Synthesis of Compound D-6
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-6 (3.8 g, 수율 70%)을 얻었다.A target compound D-6 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 43] 화합물 D-7의 합성[Synthesis Example 43] Synthesis of Compound D-7
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-7 (3.1 g (수율 58%)을 얻었다.A target compound D-7 (3.1 g (yield 58%)) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 44] 화합물 D-8의 합성[Synthesis Example 44] Synthesis of Compound D-8
합성예 37에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-8 (3.5 g, 수율 65%)을 얻었다.A target compound D-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 37, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 45] 화합물 D-9의 합성[Synthesis Example 45] Synthesis of Compound D-9
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-9 (3.0 g, 수율 55%)을 얻었다.A target compound D-9 (3.0 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 46] 화합물 D-10의 합성[Synthesis Example 46] Synthesis of Compound D-10
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-10 (3.1 g, 수율 58%)을 얻었다.A target compound D-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 47] 화합물 D-11의 합성[Synthesis Example 47] Synthesis of Compound D-11
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-11 (3.2 g, 수율 59%)을 얻었다.A target compound D-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
[LCMS] : 653[LCMS]: 653
[합성예 48] 화합물 D-12의 합성Synthesis Example 48 Synthesis of Compound D-12
합성예 37에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-12 (3.3 g, 수율 62%)을 얻었다.Except for using 2-bromobenzo[f]quinoline instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was performed to obtain the target compound D-12 (3.3 g, yield 62%).
[LCMS] : 653[LCMS]: 653
[합성예 49] 화합물 E-1의 합성[Synthesis Example 49] Synthesis of Compound E-1
준비예 5에서 합성된 화합물 E (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 E-1 (3.8 g, 수율 70 %)을 얻었다.Compound E (5 g, 8.3 mmol) synthesized in Preparation Example 5, 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) was added to 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound E-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 652[LCMS]: 652
[합성예 50] 화합물 E-2의 합성[Synthesis Example 50] Synthesis of Compound E-2
합성예 49에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-2 (3.9 g, 수율 72%)을 얻었다.A target compound E-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 49, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 51] 화합물 E-3의 합성[Synthesis Example 51] Synthesis of Compound E-3
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-3 (3.5 g, 수율 64%)을 얻었다.A target compound E-3 (3.5 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 52] 화합물 E-4의 합성[Synthesis Example 52] Synthesis of Compound E-4
합성예 49에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-4 (3.6 g, 수율 67%)을 얻었다.A target compound E-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 49, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 53] 화합물 E-5의 합성[Synthesis Example 53] Synthesis of Compound E-5
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-5 (3.8 g, 수율 71%)을 얻었다.A target compound E-5 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 54] 화합물 E-6의 합성[Synthesis Example 54] Synthesis of Compound E-6
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-6 (3.8 g, 수율 71%)을 얻었다.A target compound E-6 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 55] 화합물 E-7의 합성[Synthesis Example 55] Synthesis of Compound E-7
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-7 (3.3 g, 수율 61%)을 얻었다.A target compound E-7 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 56] 화합물 E-8의 합성[Synthesis Example 56] Synthesis of Compound E-8
합성예 49에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-8 (3.4 g, 수율 64%)을 얻었다.A target compound E-8 (3.4 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 57] 화합물 E-9의 합성[Synthesis Example 57] Synthesis of Compound E-9
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-9 (3.1 g, 수율 58%)을 얻었다.A target compound E-9 (3.1 g, yield 58%) was obtained by performing the same process as in Synthesis Example 49, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 58] 화합물 E-10의 합성[Synthesis Example 58] Synthesis of Compound E-10
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-10 (3.1 g, 수율 58%)을 얻었다.A target compound E-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 59] 화합물 E-11의 합성[Synthesis Example 59] Synthesis of Compound E-11
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-11 (3.2 g, 수율 59%)을 얻었다.A target compound E-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 60] 화합물 E-12의 합성[Synthesis Example 60] Synthesis of Compound E-12
합성예 49에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-12 (3.2 g, 수율 62%)을 얻었다.A target compound E-12 (3.2 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 49, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
[LCMS] : 652[LCMS]: 652
[합성예 61] 화합물 F-1의 합성[Synthesis Example 61] Synthesis of Compound F-1
준비예 6에서 합성된 화합물 F (5 g, 9.2 mmol), 2-bromophenanthridine (2.4 g, 9.2 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.8 g, 27.7 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 F-1 (3.7 g, 수율 68 %)을 얻었다.Compound F (5 g, 9.2 mmol), 2-bromophenanthridine (2.4 g, 9.2 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.8 g, synthesized in Preparation Example 6) 27.7 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound F-1 (3.7 g, yield 68%) was obtained using column chromatography.
[LCMS] : 593[LCMS]: 593
[합성예 62] 화합물 F-2의 합성[Synthesis Example 62] Synthesis of Compound F-2
합성예 61에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-2 (3.8 g, 수율 69%)을 얻었다.Except for using 3-bromophenanthridine instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was performed to obtain the target compound F-2 (3.8 g, yield 69%).
[LCMS] : 593[LCMS]: 593
[합성예 63] 화합물 F-3의 합성[Synthesis Example 63] Synthesis of Compound F-3
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-3 (3.9 g, 수율 72%)을 얻었다.A target compound F-3 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 64] 화합물 F-4의 합성[Synthesis Example 64] Synthesis of Compound F-4
합성예 61에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-4 (3.9 g, 수율 72%)을 얻었다.A target compound F-4 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 65] 화합물 F-5의 합성[Synthesis Example 65] Synthesis of Compound F-5
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-5 (3.8 g, 수율 70%)을 얻었다.A target compound F-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 66] 화합물 F-6의 합성[Synthesis Example 66] Synthesis of Compound F-6
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-6 (3.6 g, 수율 67%)을 얻었다.A target compound F-6 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 67] 화합물 F-7의 합성[Synthesis Example 67] Synthesis of Compound F-7
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-7 (3.6 g, 수율 67%)을 얻었다.A target compound F-7 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 68] 화합물 F-8의 합성[Synthesis Example 68] Synthesis of Compound F-8
합성예 61에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-8 (3.4 g, 수율 63%)을 얻었다.A target compound F-8 (3.4 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 61, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 69] 화합물 F-9의 합성[Synthesis Example 69] Synthesis of Compound F-9
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-9 (3.3 g, 수율 62%)을 얻었다.A target compound F-9 (3.3 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 70] 화합물 F-10의 합성[Synthesis Example 70] Synthesis of Compound F-10
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-10 (3.2 g, 수율 58%)을 얻었다.A target compound F-10 (3.2 g, yield 58%) was obtained by performing the same process as in Synthesis Example 61, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 71] 화합물 F-11의 합성[Synthesis Example 71] Synthesis of Compound F-11
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-11 (3.3 g, 수율 60%)을 얻었다.A target compound F-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 72] 화합물 F-12의 합성[Synthesis Example 72] Synthesis of Compound F-12
합성예 61에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-12 (3.2 g, 수율 59%)을 얻었다.A target compound F-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 61, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
[LCMS] : 593[LCMS]: 593
[합성예 73] 화합물 G-1의 합성[Synthesis Example 73] Synthesis of Compound G-1
준비예 7에서 합성된 화합물 G (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 G-1 (3.7 g, 수율 69 %)을 얻었다.Compound G (5 g, 8.1 mmol) synthesized in Preparation Example 7, 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) was added to 50 ml of Toluene, 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound G-1 (3.7 g, yield 69%) was obtained using column chromatography.
[LCMS] : 669[LCMS]: 669
[합성예 74] 화합물 G-2의 합성[Synthesis Example 74] Synthesis of Compound G-2
합성예 73에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-2 (3.7 g, 수율 69%)을 얻었다.A target compound G-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 73, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 75] 화합물 G-3의 합성[Synthesis Example 75] Synthesis of Compound G-3
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-3 (3.8 g, 수율 70%)을 얻었다.A target compound G-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 76] 화합물 G-4의 합성[Synthesis Example 76] Synthesis of Compound G-4
합성예 73에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-4 (3.6 g (수율 67%)을 얻었다.A target compound G-4 (3.6 g (yield 67%)) was obtained by performing the same procedure as in Synthesis Example 73, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 77] 화합물 G-5의 합성[Synthesis Example 77] Synthesis of Compound G-5
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-5 (3.6 g, 수율 67%)을 얻었다.A target compound G-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 78] 화합물 G-6의 합성[Synthesis Example 78] Synthesis of Compound G-6
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-6 (3.5 g, 수율 65%)을 얻었다.A target compound G-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 79] 화합물 G-7의 합성[Synthesis Example 79] Synthesis of Compound G-7
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-7 (3.5 g, 수율 65%)을 얻었다.A target compound G-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 80] 화합물 G-8의 합성[Synthesis Example 80] Synthesis of Compound G-8
합성예 73에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-8 (3.4 g, 수율 62%)을 얻었다.A target compound G-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 73, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 81] 화합물 G-9의 합성[Synthesis Example 81] Synthesis of Compound G-9
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-9 (3.3 g, 수율 60%)을 얻었다.A target compound G-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 82] 화합물 G-10의 합성[Synthesis Example 82] Synthesis of Compound G-10
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-10 (2.9 g, 수율 54%)을 얻었다.A target compound G-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 83] 화합물 G-11의 합성[Synthesis Example 83] Synthesis of Compound G-11
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-11 (2.8 g, 수율 53%)을 얻었다.A target compound G-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 84] 화합물 G-12의 합성[Synthesis Example 84] Synthesis of Compound G-12
합성예 73에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-12 (2.8 g, 수율 53%)을 얻었다.A target compound G-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
[LCMS] : 669[LCMS]: 669
[합성예 85] 화합물 H-1의 합성[Synthesis Example 85] Synthesis of Compound H-1
준비예 8에서 합성된 화합물 H (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 H-1 (3.7 g, 수율 69 %)을 얻었다.Compound H (5 g, 8.1 mmol) synthesized in Preparation Example 8, 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound H-1 (3.7 g, yield 69%) was obtained using column chromatography.
[LCMS] : 669[LCMS]: 669
[합성예 86] 화합물 H-2의 합성[Synthesis Example 86] Synthesis of Compound H-2
합성예 85에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-2 (3.7 g, 수율 69%)을 얻었다.A target compound H-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 85, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 87] 화합물 H-3의 합성[Synthesis Example 87] Synthesis of Compound H-3
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-3 (3.8 g, 수율 70%)을 얻었다.A target compound H-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 88] 화합물 H-4의 합성[Synthesis Example 88] Synthesis of Compound H-4
합성예 85에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-4 (3.6 g, 수율 67%)을 얻었다.A target compound H-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 89] 화합물 H-5의 합성[Synthesis Example 89] Synthesis of Compound H-5
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-5 (3.6 g, 수율 67%)을 얻었다.A target compound H-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 90] 화합물 H-6의 합성[Synthesis Example 90] Synthesis of Compound H-6
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-6 (3.5 g, 수율 65%)을 얻었다.A target compound H-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 91] 화합물 H-7의 합성[Synthesis Example 91] Synthesis of Compound H-7
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-7 (3.5 g, 수율 65%)을 얻었다.A target compound H-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 92] 화합물 H-8의 합성[Synthesis Example 92] Synthesis of Compound H-8
합성예 85에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-8 (3.4 g, 수율 62%)을 얻었다.A target compound H-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 85, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 93] 화합물 H-9의 합성[Synthesis Example 93] Synthesis of Compound H-9
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-9 (3.3 g, 수율 60%)을 얻었다.A target compound H-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 94] 화합물 H-10의 합성[Synthesis Example 94] Synthesis of Compound H-10
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-10 (2.9 g, 수율 54%)을 얻었다.A target compound H-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 95] 화합물 H-11의 합성[Synthesis Example 95] Synthesis of Compound H-11
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-11 (2.8 g, 수율 53%)을 얻었다.A target compound H-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 96] 화합물 H-12의 합성[Synthesis Example 96] Synthesis of Compound H-12
합성예 85에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-12 (2.8 g, 수율 53%)을 얻었다.A target compound H-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
[LCMS] : 669[LCMS]: 669
[합성예 97] 화합물 I-1의 합성[Synthesis Example 97] Synthesis of Compound I-1
준비예 9에서 합성된 화합물 I (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 I-1 (4.2 g, 수율 78 %)을 얻었다.Compound I (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, synthesized in Preparation Example 9) 24.3 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound I-1 (4.2 g, yield 78%) was obtained using column chromatography.
[LCMS] : 669[LCMS]: 669
[합성예 98] 화합물 I-2의 합성[Synthesis Example 98] Synthesis of Compound I-2
합성예 97에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-2 (4.1 g, 수율 76%)을 얻었다.A target compound I-2 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 99] 화합물 I-3의 합성[Synthesis Example 99] Synthesis of Compound I-3
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-3 (4.1 g, 수율 76%)을 얻었다.A target compound I-3 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 100] 화합물 I-4의 합성[Synthesis Example 100] Synthesis of Compound I-4
합성예 97에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-4 (3.8 g, 수율 70%)을 얻었다.A target compound I-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 97, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 101] 화합물 I-5의 합성[Synthesis Example 101] Synthesis of Compound I-5
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-5 (3.6 g, 수율 67%)을 얻었다.A target compound I-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 102] 화합물 I-6의 합성[Synthesis Example 102] Synthesis of Compound I-6
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-6 (3.7 g, 수율 68%)을 얻었다.A target compound I-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 103] 화합물 I-7의 합성[Synthesis Example 103] Synthesis of Compound I-7
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-7 (3.7 g, 수율 68%)을 얻었다.A target compound I-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 104] 화합물 I-8의 합성[Synthesis Example 104] Synthesis of Compound I-8
합성예 97에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-8 (3.4 g, 수율 62%)을 얻었다.A target compound I-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 97, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 105] 화합물 I-9의 합성[Synthesis Example 105] Synthesis of Compound I-9
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-9 (3.2 g, 수율 60%)을 얻었다.A target compound I-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 106] 화합물 I-10의 합성[Synthesis Example 106] Synthesis of Compound I-10
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-10 (2.9 g, 수율 54%)을 얻었다.A target compound I-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 107] 화합물 I-11의 합성[Synthesis Example 107] Synthesis of Compound I-11
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-11 (3.3 g, 수율 60%)을 얻었다.A target compound I-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 108] 화합물 I-12의 합성[Synthesis Example 108] Synthesis of Compound I-12
합성예 97에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-12 (2.9 g, 수율 54%)을 얻었다.A target compound I-12 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
[LCMS] : 669[LCMS]: 669
[합성예 109] 화합물 J-1의 합성[Synthesis Example 109] Synthesis of Compound J-1
준비예 10에서 합성된 화합물 J (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-1 (4.2 g, 수율 78 %)을 얻었다.Compound J (5 g, 8.1 mmol) synthesized in Preparation Example 10, 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound J-1 (4.2 g, yield 78%) was obtained using column chromatography.
[LCMS] : 668[LCMS]: 668
[합성예 110] 화합물 J-2의 합성[Synthesis Example 110] Synthesis of Compound J-2
합성예 109에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-2 (4.1 g, 수율 76%)을 얻었다.The same procedure as in Synthesis Example 109 was performed, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, to obtain the target compound J-2 (4.1 g, yield 76%).
[LCMS] : 668[LCMS]: 668
[합성예 111] 화합물 J-3의 합성[Synthesis Example 111] Synthesis of Compound J-3
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-3 (3.7 g, 수율 68%)을 얻었다.A target compound J-3 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 112] 화합물 J-4의 합성[Synthesis Example 112] Synthesis of Compound J-4
합성예 109에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-4 (3.8 g, 수율 70%)을 얻었다.A target compound J-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 109, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 113] 화합물 J-5의 합성[Synthesis Example 113] Synthesis of Compound J-5
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-5 (3.6 g, 수율 67%)을 얻었다.The same procedure as in Synthesis Example 109 was performed, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, to obtain the target compound J-5 (3.6 g, yield 67%).
[LCMS] : 668[LCMS]: 668
[합성예 114] 화합물 J-6의 합성[Synthesis Example 114] Synthesis of Compound J-6
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-6 (3.7 g, 수율 68%)을 얻었다.A target compound J-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 115] 화합물 J-7의 합성[Synthesis Example 115] Synthesis of Compound J-7
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-7 (3.8 g, 수율 70%)을 얻었다.A target compound J-7 (3.8 g, yield 70%) was obtained by performing the same process as in Synthesis Example 109, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 116] 화합물 J-8의 합성[Synthesis Example 116] Synthesis of Compound J-8
합성예 109에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-8 (3.2 g, 수율 60%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was performed to obtain the target compound J-8 (3.2 g, yield 60%).
[LCMS] : 668[LCMS]: 668
[합성예 117] 화합물 J-9의 합성[Synthesis Example 117] Synthesis of Compound J-9
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-9 (3.2 g, 수율 60%)을 얻었다.A target compound J-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 118] 화합물 J-10의 합성[Synthesis Example 118] Synthesis of Compound J-10
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-10 (3.1 g, 수율 54%)을 얻었다.A target compound J-10 (3.1 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 119] 화합물 J-11의 합성[Synthesis Example 119] Synthesis of Compound J-11
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-11 (3.3 g, 수율 60%)을 얻었다.A target compound J-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
[LCMS] : 668[LCMS]: 668
[합성예 120] 화합물 J-12의 합성[Synthesis Example 120] Synthesis of Compound J-12
합성예 109에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-12 (3.0 g, 수율 56%)을 얻었다.Except for using 2-bromobenzo[f]quinoline instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was performed to obtain the target compound J-12 (3.0 g, yield 56%).
[LCMS] : 668[LCMS]: 668
[실시예 1] 청색 유기 전계 발광 소자의 제작[Example 1] Preparation of blue organic electroluminescent device
합성예에서 합성된 화합물 A-1를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.The compound A-1 synthesized in the synthesis example was subjected to a high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 Å was washed with distilled water. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed for 5 minutes using UV. The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/95 wt%의 ADN + 5 wt%의 DS-405(㈜두산전자)(30 nm)/화합물 A-1(30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/95 wt% of ADN + 5 wt% of DS-405 (Doosan Electronics)(30 nm)/ Compound A-1 (30 nm) / LiF (1 nm) / Al (200 nm) was stacked in order to prepare an organic electroluminescent device.
이때, 사용된 NPB, ADN의 구조는 각각 하기와 같다.At this time, the structures of the NPB and ADN used are as follows.
[실시예 2~120] 청색 유기 전계 발광 소자의 제작[Examples 2 to 120] Preparation of blue organic electroluminescent device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1 대신 하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 below was used instead of Compound A-1 used as the electron transport layer material in Example 1.
[비교예 1] 청색 유기 전계 발광 소자의 제작[Comparative Example 1] Preparation of blue organic electroluminescent device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1 대신 Alq3을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때, 사용된 Alq3의 구조는 각각 하기와 같다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound A-1 used as the electron transport layer material in Example 1. At this time, the structures of Alq 3 used are as follows.
[비교예 2] 청색 유기 전계 발광 소자의 제작[Comparative Example 2] Preparation of blue organic electroluminescent device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1을 사용하지 않은 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 used as the electron transport layer material in Example 1 was not used.
[평가예 1][Evaluation Example 1]
실시예 1 내지 120 및 비교예 1~2 에서 제작된 각각의 청색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For each blue organic electroluminescent device produced in Examples 1 to 120 and Comparative Examples 1 to 2, driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. Shown.
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물(A-1~J-12)을 전자 수송층 재료로 사용한 실시예 1~120의 청색 유기 전계 발광 소자는 종래 전자 수송층 재료인 Alq3를 사용한 비교예 1의 청색 유기 전계 발광 소자 및 전자 수송층이 없는 비교예 2의 청색 유기 전계 발광 소자에 비해 구동전압, 발광 피크 및 전류효율 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 120 using the compounds (A-1 to J-12) according to the present invention as electron transport layer materials were compared using Alq 3 , a conventional electron transport layer material. It was found that the blue organic electroluminescent device of Example 1 and the blue organic electroluminescent device of Comparative Example 2 without an electron transport layer showed better performance in terms of driving voltage, emission peak, and current efficiency.
Claims (15)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the formula (1):[화학식 1][Formula 1]
(상기 화학식 1에서,(In the formula 1,X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하며, X 1 to X 3 are the same as or different from each other, and each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and when CR 2 is plural, a plurality of R 2 s are the same or different from each other Different,Y는 O 또는 S이고, Y is O or S,Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 적어도 하나는 N이며, 이때 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 상이하며, Z 1 to Z 10 are the same or different from each other, and each independently is N or CR 3 , but at least one of Z 1 to Z 10 is N, and when CR 3 is plural, a plurality of R 3 s are the same or different from each other Different,a 및 b는 각각 1 내지 3의 정수이고,a and b are each an integer from 1 to 3,L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이며,L 1 and L 2 are the same as or different from each other, and each independently a single bond or an arylene group of C 6 to C 60 ,Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,c는 0 내지 4의 정수이고, 이때 복수의 R3는 서로 동일하거나 상이하며,c is an integer from 0 to 4, wherein a plurality of R 3 are the same or different from each other,R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 arylboronic group, C 6 ~ C 60 aryl phosphine group, and selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene groups of L 1 and L 2 , aryl groups and heteroaryl groups of Ar 1 and Ar 2 , alkyl groups of R 1 to R 3 , alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, deuterium, halogen, cyano group, Nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C Aryl group of 6 ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C of the group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of the C 60 group And C 6 ~ C 60 is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, wherein when the plurality of substituents, they are the same or different from each other). - 제1항에 있어서,According to claim 1,상기 화학식 1에서, In Chemical Formula 1,상기 L1 및 L2는모이어티에 대해 서로 메타(meta) 위치로 결합되는 화합물. L 1 and L 2 are
Compounds that are bonded to each other in a meta position to the moiety. - 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 2로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by Formula 2 below:[화학식 2][Formula 2]
(상기 식에서,(In the above formula,X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,L1은 페닐렌인 화합물.L 1 is phenylene.
- 제1항에 있어서, According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 3 또는 4로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by Formula 3 or 4 below:[화학식 3][Formula 3]
[화학식 4][Formula 4]
(상기 식에서,(In the above formula,X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 5 내지 7 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of the following Formulas 5 to 7:[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
(상기 식에서,(In the above formula,X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,X1 내지 X3 중 적어도 2개는 N인 화합물.At least 2 of X 1 to X 3 are N compounds.
- 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 8 또는 9로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by Formula 8 or 9 below:[화학식 8][Formula 8]
[화학식 9][Formula 9]
(상기 식에서,(In the above formula,Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 10 내지 15 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of the following Formulas 10 to 15:[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
(상기 식에서,(In the above formula,Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 16 내지 27 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of the following Formulas 16 to 27:[화학식 16][Formula 16]
[화학식 17][Formula 17]
[화학식 18][Formula 18]
[화학식 19][Formula 19]
[화학식 20][Formula 20]
[화학식 21][Formula 21]
[화학식 22][Formula 22]
[화학식 23][Formula 23]
[화학식 24][Formula 24]
[화학식 25][Formula 25]
[화학식 26][Formula 26]
[화학식 27][Formula 27]
(상기 식에서,(In the above formula,Y, Z1 내지 Z10, c, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , R 1 are each as defined in claim 1). - 제1항에 있어서,According to claim 1,상기 화학식 1에서,모이어티는 하기 치환체 S1 내지 S19로 이루어진 군에서 선택된 치환체인 화합물:In Chemical Formula 1,
The moiety is a compound selected from the group consisting of the following substituents S1 to S19:.
. - 제1항에 있어서,According to claim 1,상기 화학식 1에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 비페닐기인 화합물.In Formula 1, Ar 1 and Ar 2 are the same as or different from each other, and each independently a phenyl group or a biphenyl compound.
- 제1항에 있어서,According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화합물 A-1 내지 A-12, B-1 내지 B-12, C-1 내지 C-12, D-1 내지 D-12, E-1 내지 E-12, F-1 내지 F-12, G-1 내지 G-12, H-1 내지 H-12, I-1 내지 I-12, 및 J-1 내지 J-12로 이루어진 군에서 선택된 화합물:Compound represented by Formula 1 is the following compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D-12, E-1 to E-12, Compounds selected from the group consisting of F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12:
.
. - (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제13항 중 어느 한 항에 기재된 유기 화합물을 포함하는 유기 전계 발광 소자. An organic electroluminescent device comprising at least one of the one or more organic material layers comprising the organic compound according to any one of claims 1 to 13.
- 제14항에 있어서,The method of claim 14,상기 유기 화합물을 포함하는 유기물층은 전자 수송층인 유기 전계 발광 소자.The organic material layer including the organic compound is an organic electroluminescent device that is an electron transport layer.
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| KR20170013152A (en) * | 2015-07-27 | 2017-02-06 | 희성소재 (주) | Hetero-cyclic compound and organic light emitting device using the same |
| KR20170057660A (en) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | Heterocyclic compound and organic electronic device using the same |
| KR20170102000A (en) * | 2015-02-13 | 2017-09-06 | 코니카 미놀타 가부시키가이샤 | Aromatic heterocyclic derivatives, organic electroluminescent devices using the same, lighting devices and display devices |
| KR20180071621A (en) * | 2016-12-20 | 2018-06-28 | 희성소재 (주) | Organic light emitting device and composition for organic layer of organic light emitting device |
| KR20180076289A (en) * | 2016-12-27 | 2018-07-05 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
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| KR20170013152A (en) * | 2015-07-27 | 2017-02-06 | 희성소재 (주) | Hetero-cyclic compound and organic light emitting device using the same |
| KR20170057660A (en) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | Heterocyclic compound and organic electronic device using the same |
| KR20180071621A (en) * | 2016-12-20 | 2018-06-28 | 희성소재 (주) | Organic light emitting device and composition for organic layer of organic light emitting device |
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| WO2021083030A1 (en) * | 2019-10-31 | 2021-05-06 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, electronic component and electronic apparatus |
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