WO2015125986A1 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
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- WO2015125986A1 WO2015125986A1 PCT/KR2014/001393 KR2014001393W WO2015125986A1 WO 2015125986 A1 WO2015125986 A1 WO 2015125986A1 KR 2014001393 W KR2014001393 W KR 2014001393W WO 2015125986 A1 WO2015125986 A1 WO 2015125986A1
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 22
- 125000005264 aryl amine group Chemical group 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- -1 alkyl boron Chemical compound 0.000 claims description 18
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 41
- WRNKIDLXXXIELU-IEBWSBKVSA-N LSM-3788 Chemical compound C1=CC([C@H]2C3=CC=CC=C3CN([C@@H]2C2)C)=C3C2=CNC3=C1 WRNKIDLXXXIELU-IEBWSBKVSA-N 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 224
- 238000003786 synthesis reaction Methods 0.000 description 224
- 239000010410 layer Substances 0.000 description 64
- 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 55
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 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 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IYERRTIEAMZWGN-UHFFFAOYSA-N 4-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=CC2=C1C=CN2 IYERRTIEAMZWGN-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- MVXAMSQSLSIEFR-UHFFFAOYSA-N 1-(2-bromophenyl)-4-(2-nitrophenyl)indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=CC2=C1C=CN2C1=CC=CC=C1Br MVXAMSQSLSIEFR-UHFFFAOYSA-N 0.000 description 8
- JCHCMDATTFUCPZ-UHFFFAOYSA-N 19-(2-nitrophenyl)-14-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8,10,12,15,17,19-decaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C=1C=2C=C3N(C=4C=CC=CC4C4=CC=CC=C34)C2C=CC1 JCHCMDATTFUCPZ-UHFFFAOYSA-N 0.000 description 8
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 0 *c1c(cc2[n]3c4ccccc4c4ccccc24)c3c(*)c2c1[n]c1c2c(*)c(*)c(*)c1* Chemical compound *c1c(cc2[n]3c4ccccc4c4ccccc24)c3c(*)c2c1[n]c1c2c(*)c(*)c(*)c1* 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- RVGIFKFVCZFLJB-UHFFFAOYSA-N 1-(2-bromophenyl)-5-(2-nitrophenyl)indole Chemical compound BrC1=C(C=CC=C1)N1C=CC2=CC(=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-] RVGIFKFVCZFLJB-UHFFFAOYSA-N 0.000 description 3
- YZLIWDNHHXEQEN-UHFFFAOYSA-N 1-(2-bromophenyl)-5-(5-chloro-2-nitrophenyl)indole Chemical compound BrC1=C(C=CC=C1)N1C=CC2=CC(=CC=C12)C1=C(C=CC(=C1)Cl)[N+](=O)[O-] YZLIWDNHHXEQEN-UHFFFAOYSA-N 0.000 description 3
- GJPMIDKOJLXGNT-UHFFFAOYSA-N 1-(2-bromophenyl)-6-(2-nitrophenyl)indole Chemical compound BrC1=C(C=CC=C1)N1C=CC2=CC=C(C=C12)C1=C(C=CC=C1)[N+](=O)[O-] GJPMIDKOJLXGNT-UHFFFAOYSA-N 0.000 description 3
- MHTMPLVLIPWBNF-UHFFFAOYSA-N 1-(2-bromophenyl)-7-(2-nitrophenyl)indole Chemical compound BrC1=C(C=CC=C1)N1C=CC2=CC=CC(=C12)C1=C(C=CC=C1)[N+](=O)[O-] MHTMPLVLIPWBNF-UHFFFAOYSA-N 0.000 description 3
- WUQVOVDEWWIGBA-UHFFFAOYSA-N 16-(2-nitrophenyl)-14-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=CC=2C=C3N(C=4C=CC=CC4C4=CC=CC=C34)C12 WUQVOVDEWWIGBA-UHFFFAOYSA-N 0.000 description 3
- NGGZFLNXEWOVFA-UHFFFAOYSA-N 17-(2-nitrophenyl)-14-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C=1C=CC=2C=C3N(C=4C=CC=CC4C4=CC=CC=C34)C2C1 NGGZFLNXEWOVFA-UHFFFAOYSA-N 0.000 description 3
- SHOJBUJDHPEZKQ-UHFFFAOYSA-N 18-(2-nitrophenyl)-14-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=2C=C3N(C=4C=CC=CC4C4=CC=CC=C34)C2C=C1 SHOJBUJDHPEZKQ-UHFFFAOYSA-N 0.000 description 3
- WBTPPNRIUBLXFT-UHFFFAOYSA-N 18-(5-chloro-2-nitrophenyl)-14-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound ClC=1C=CC(=C(C1)C1=CC=2C=C3N(C=4C=CC=CC4C4=CC=CC=C34)C2C=C1)[N+](=O)[O-] WBTPPNRIUBLXFT-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- NRDZHTMNMSJGKG-UHFFFAOYSA-N 5-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(NC=C2)C2=C1 NRDZHTMNMSJGKG-UHFFFAOYSA-N 0.000 description 3
- OFPDSZLJFBXAQC-UHFFFAOYSA-N 5-(5-chloro-2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C1=CC=C(NC=C2)C2=C1 OFPDSZLJFBXAQC-UHFFFAOYSA-N 0.000 description 3
- JSVPPCUHRRGCCL-UHFFFAOYSA-N 6-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(C=CN2)C2=C1 JSVPPCUHRRGCCL-UHFFFAOYSA-N 0.000 description 3
- HKNCBGHUEKCKFD-UHFFFAOYSA-N 7-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=CC2=C1NC=C2 HKNCBGHUEKCKFD-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- CIRBFLPBOHHKOC-UHFFFAOYSA-N N-(2,5-dibromophenyl)phenanthridin-6-amine Chemical compound BrC1=C(C=C(C=C1)Br)NC=1N=C2C=CC=CC2=C2C=CC=CC12 CIRBFLPBOHHKOC-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 2
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- RKPPHBJIJYHCHW-UHFFFAOYSA-N C1=CC2=CN=C3C=CC=CC3=C2C2=C1C(N=CN1)=C1C=C2 Chemical group C1=CC2=CN=C3C=CC=CC3=C2C2=C1C(N=CN1)=C1C=C2 RKPPHBJIJYHCHW-UHFFFAOYSA-N 0.000 description 2
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- 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
- 150000001336 alkenes Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- XBHPFCIWRHJDCP-UHFFFAOYSA-N (2-trimethylsilylphenyl) trifluoromethanesulfonate Chemical compound C[Si](C)(C)C1=CC=CC=C1OS(=O)(=O)C(F)(F)F XBHPFCIWRHJDCP-UHFFFAOYSA-N 0.000 description 1
- WTYKIOBQNRWDQP-UHFFFAOYSA-N (3-bromophenyl)-triphenylsilane Chemical compound BrC1=CC=CC([Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 WTYKIOBQNRWDQP-UHFFFAOYSA-N 0.000 description 1
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- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
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- 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
- GZZLAPUQZCXKKT-UHFFFAOYSA-N 1-bromo-3-diphenylphosphorylbenzene Chemical compound BrC1=CC=CC(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GZZLAPUQZCXKKT-UHFFFAOYSA-N 0.000 description 1
- JGGNJDKQZHDKHQ-UHFFFAOYSA-N 1H-indole Chemical group C1=CC=C2NC=CC2=C1.C1=CC=C2NC=CC2=C1 JGGNJDKQZHDKHQ-UHFFFAOYSA-N 0.000 description 1
- WRTAZRGRFBCKBU-UHFFFAOYSA-N 2,5-dibromoaniline Chemical compound NC1=CC(Br)=CC=C1Br WRTAZRGRFBCKBU-UHFFFAOYSA-N 0.000 description 1
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- CNLVYZSUMYQALH-UHFFFAOYSA-N 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole Chemical compound C1=CC(Br)=CC=C1C1=NN=C(C=2C=CC=CC=2)O1 CNLVYZSUMYQALH-UHFFFAOYSA-N 0.000 description 1
- FMBZXHUFHIXHHA-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-phenylphenyl)quinazoline Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 FMBZXHUFHIXHHA-UHFFFAOYSA-N 0.000 description 1
- PLXPMZVMTNSXBA-UHFFFAOYSA-N 2-[3-(3-bromophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2C=C(C=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 PLXPMZVMTNSXBA-UHFFFAOYSA-N 0.000 description 1
- ZCCPIXWQNBPVDR-UHFFFAOYSA-N 2-[3-(4-bromophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ZCCPIXWQNBPVDR-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- LPSLMIOUKRPZDC-UHFFFAOYSA-N 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC(Cl)=NC(C=2C=CC(C)=CC=2)=N1 LPSLMIOUKRPZDC-UHFFFAOYSA-N 0.000 description 1
- QNGVEVOZKYHNGL-UHFFFAOYSA-N 2-chloro-4,6-diphenylpyrimidine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QNGVEVOZKYHNGL-UHFFFAOYSA-N 0.000 description 1
- YTTFZSLFNVFHAQ-UHFFFAOYSA-N 2-chloro-4-(4-naphthalen-1-ylphenyl)quinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C=CC=3)=C21 YTTFZSLFNVFHAQ-UHFFFAOYSA-N 0.000 description 1
- SJAMSUCDGMZEFD-UHFFFAOYSA-N 2-chloro-4-[3-(9,9-dimethylfluoren-2-yl)phenyl]pyrimidine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1C(C=1)=CC=CC=1C1=CC=NC(Cl)=N1 SJAMSUCDGMZEFD-UHFFFAOYSA-N 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- YDXLVFKTOSKBKT-UHFFFAOYSA-N 3-bromo-n,n-diphenylaniline Chemical compound BrC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YDXLVFKTOSKBKT-UHFFFAOYSA-N 0.000 description 1
- UYROTQZLUVRLJT-UHFFFAOYSA-N 4-(4-bromophenyl)-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC(Br)=CC=C1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 UYROTQZLUVRLJT-UHFFFAOYSA-N 0.000 description 1
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 1
- MAWGHOPSCKCTPA-UHFFFAOYSA-N 6-bromo-1h-indole Chemical compound BrC1=CC=C2C=CNC2=C1 MAWGHOPSCKCTPA-UHFFFAOYSA-N 0.000 description 1
- XHZTZKAXCPJABO-UHFFFAOYSA-N 6-chlorophenanthridine Chemical compound C1=CC=C2C(Cl)=NC3=CC=CC=C3C2=C1 XHZTZKAXCPJABO-UHFFFAOYSA-N 0.000 description 1
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
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- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MMWVZGHFFUMWBM-UHFFFAOYSA-N [O-][N+](c1ccccc1-c(cc1)cc2c1[n]1c(cccc3)c3c3ccccc3c1n2)=O Chemical compound [O-][N+](c1ccccc1-c(cc1)cc2c1[n]1c(cccc3)c3c3ccccc3c1n2)=O MMWVZGHFFUMWBM-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- DHUWBNXXQFWIKW-UHFFFAOYSA-N chloro(diphenyl)borane Chemical compound C=1C=CC=CC=1B(Cl)C1=CC=CC=C1 DHUWBNXXQFWIKW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- GDLYCTKVUHXJBM-UHFFFAOYSA-N diphenylborane Chemical compound C=1C=CC=CC=1BC1=CC=CC=C1 GDLYCTKVUHXJBM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
- H10K85/658—Organoboranes
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Definitions
- the present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage, lifespan, etc. of the device are improved.
- 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 and the like according to its function.
- the light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
- a host / dopant system may be used as a light emitting material.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB, BCP, Alq 3 and the like are widely known as a hole injection layer, a hole transport layer, a hole blocking layer, and an electron transport layer, and anthracene derivatives are reported as fluorescent dopant / host materials as light emitting materials.
- phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.
- an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
- the present invention provides a compound represented by Formula 1:
- At least one of R 1 and R 2 , R 2 and R 3, or R 3 and R 4 combine with Formula 2 to form a condensed ring,
- the dotted line represents a site where condensation occurs with the compound of Formula 1.
- X 1 is N or CR 9 ,
- X 2 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
- Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10 , each R 10 may be the same or different,
- R 1 to R 10 are the same or different and are each independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ alkynyl group of C 40 , C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group , C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It is selected from the group consisting of an arylsilyl group, these
- Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group , nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 cycloalkyl group , nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 group of the arylboronic, C 6 ⁇ C 40 aryl phosphine A pin group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group,
- the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises a compound of Formula 1 It is an organic electroluminescent device characterized by.
- At least one of the one or more organic material layers may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, it is preferable that the light emitting layer.
- the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.
- the compound represented by Chemical Formula 1 of the present invention is excellent in thermal stability and phosphorescence property, it may be used as a material of the organic material layer of the organic EL device.
- the compound represented by Chemical Formula 1 of the present invention when used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to a conventional host material can be manufactured, and further, performance And a full color display panel with greatly improved lifespan.
- novel compounds according to the present invention are indolophenanthridine moiety or benzoimidazolophenanthridine moiety in the end of the indole (indole) moiety is fused to form a basic skeleton, such As a structure in which various substituents are bonded to the basic skeleton, it is represented by the formula (1).
- the compound represented by Formula 1 has a wide bandgap due to the indolophenanthridine moiety or the indole moiety bound to the terminal of the benzoimidazolophenanthridine moiety.
- the entire molecule has a bipolar (bipolar) properties, it is possible to increase the binding force between the hole and the electron. Therefore, the compound of Formula 1 may improve the phosphorescence property of the organic EL device and also improve the hole injection ability, transport ability, or luminous efficiency.
- the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, so that the glass transition temperature can be improved, and thus, the conventional CBP (4,4-dicarbazolybiphenyl) May have higher thermal stability.
- the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifespan characteristics.
- the compound represented by the formula (1) of the present invention when adopted as a material of the hole injection / transport layer of the organic EL device as a phosphorescent host material of blue, green, and / or red, the efficiency and lifespan of the conventional CBP are excellent. It can exert an excellent effect. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and the improvement of the life of the organic EL device can lead to the maximization of the performance in the full color organic light emitting panel.
- Compound represented by the formula (1) of the present invention in combination with the formula (2) in which the condensed ring is formed may be more specifically represented by a compound represented by any one of the following formula (3).
- Such compounds represented by the formulas (3) to (8) are preferred when considering the properties of the organic EL device.
- X 1 , X 2, R 1 to R 8 and Y 1 to Y 8 are the same as defined in Chemical Formula 1, respectively.
- X 1 is N or CR 9 and X 2 is selected from O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) .
- X 1 is N or CR 9
- X 2 is N (Ar 1 ), more preferably X 1 is N, and X 2 is N (Ar 1 ).
- Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10, wherein each R 10 may be the same or different.
- Y 1 to Y 8 are all CR 10, wherein each R 10 may be the same or different.
- Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ C 40 cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ aryl boronic of C 40, a C 6 ⁇ C 40 Aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It is selected from the group consisting of arylsilyls
- Ar 1 to Ar 5 are the same or different from each other, each independently substituted or unsubstituted C 6 ⁇ C 40
- R 1 to R 10 excluding R 1 and R 2 , R 2 and R 3 , and / or at least one of R 3 and R 4 are the same as each other. or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ aryl of C 40 alkynyl group, C 6 ⁇ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C
- R 1 to R 10 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ⁇ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms and It is preferably selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
- an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of the , C 6 -C 40 arylamine group
- Compound represented by the formula (1) of the present invention in combination with the formula (2) formed a condensed ring may be more preferably embodied as a compound represented by any one of the following formulas (9) to (20). Such compounds represented by the formulas (9) to (20) are more preferable in consideration of the characteristics of the organic EL device.
- R 1 to R 8 and Ar 1 are as defined in Formula 1, respectively.
- Ar 1 is C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group, Nuclear atoms of 5 to 40 hetero Aryl group, C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3 to 40 hetero Cycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl It is selected from the group consisting of a phosphine oxide group and a C 6 -C 40 arylsilyl group.
- Ar 1 is preferably a substituted or unsubstituted C 6 ⁇ C 40 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.
- R 1 and R 2, R 2 and R 3, and / or R 3 and R 4 of R 1 to R 8 except for at least one or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ aryl of C 40 alkynyl group, C 6 ⁇ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C
- R 1 to R 8 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ⁇ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, And it is preferably selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
- an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of the , C 6 -C 40 arylamine group
- R 1 to R 10 and Ar 1 to Ar 5 are each independently selected from hydrogen or a substituent group represented by S1 to S204, but are not limited thereto.
- R 1 to R 10 and Ar 1 to Ar 5 may be each independently selected from hydrogen or the following substituent groups.
- alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, and iso-amyl. And hexyl.
- alkenyl is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.
- Alkynyl in the present invention is 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 thereof include ethynyl, 2-propynyl etc. are mentioned.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are pendant or condensed with each other may also be included. Examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. 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 or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furany
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
- R'O- monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
- alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- 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 cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
- heterocycloalkyl include morpholine, piperazine and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
- another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
- the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3) to (8).
- the compound of Formula 1 may be used alone, or two or more may be mixed.
- the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
- the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.
- the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
- the compound of Formula 1 when included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
- the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
- at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be.
- the compound represented by Formula 1 of the present invention may be used as a phosphorescent host material of the light emitting layer.
- the electron injection layer may be further stacked on the electron transport layer.
- the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
- the organic electroluminescent device according to the present invention may be formed using other materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It can be produced by forming an organic material layer and an electrode.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
- examples of the anode 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), indium zinc oxide (IZO); Combinations of metals and oxides 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 are 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.
- 6-chlorophenanthridine (18.8 g, 88.0 mmol), 2,5-dibromoaniline (24.3 g, 96.7 mmol), and 1000 ml of diglyme were added under nitrogen stream and stirred at 160 ° C. for 3 hours. After completion of the reaction, filtered, and recrystallized with EA and Hexane to obtain the target compound N- (2,5-dibromophenyl) phenanthridin-6-amine (29.4 g, 68.6 mmol, yield 78%).
- N- (2,5-dibromophenyl) phenanthridin-6-amine (37.2 g, 87.0 mmol), triphenylphosphine (4.5 g, 17 mmol), palladium acetate (1.2 g, 5 mmol), pstassium carbonate (36.0 g 260) under nitrogen stream mmol) was added to 1000 ml of toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the organic layer filtered to obtain the target compound IPTN-Br (19.0 g, 54.8 mmol, 63% yield) by column chromatography.
- IPTN-Br 30.6 g, 88.0 mmol
- 4-bromo-1H-indole was carried out the same procedure as in ⁇ Step 1> of Preparation Example 1
- IPTN1 (24.3 g, 62.5 mmol, yield 71% )
- IPT-1 (3.56 g, 10.00 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.00 mmol), Cu powder (0.06 g) under nitrogen stream , 1.00 mmol), K 2 CO 3 (2.76 g, 20.00 mmol), Na 2 SO 4 (2.84 g, 20.00 mmol) and nitrobenzene (50 ml) were mixed and stirred at 200 ° C. for 12 hours.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 1 as a light emitting host material when forming the emission layer.
- Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
- Example 1 C 1 6.74 515 40.0
- Example 2 C 2 6.46 518 41.8
- Example 3 C 17 6.71 517 44.2
- Example 4 C 19 6.79 515 41.7
- Example 5 25 6.55 518 41.5
- Example 6 C 27 6.69 515 42.7
- Example 7 C 57 6.69 518 43.0
- Example 8 C 58 6.70 517 43.3
- Example 9 C 73 6.34 515 44.1
- Example 10 C 75 6.70 518 41.4
- Example 11 C 81 6.66 517 42.2
- Example 12 C 83 6.65 518 43.1
- Example 13 C 113 6.65 515 41.1
- Example 14 C 114 6.71 518 42.0
- Example 15 C 129 6.72 515 42.5
- Example 16 131 6.72 518 41.3
- Example 18 C C 139 6.73 517 41.6
- the green organic EL device (Examples 1 to 61) using the compounds (C 1 to C 527) according to the present invention as a light emitting layer is a green organic EL device (Comparative Example 1) using a conventional CBP. Compared with, it can be seen that the better performance in terms of efficiency and driving voltage.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / C 129, C 493, C 496, C 498 + 10% (piq) 2 Ir (acac) (300nm) /
- An organic electroluminescent device was manufactured by laminating in the order of BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
- a red organic electroluminescent device was manufactured in the same manner as in Example 62, except that CBP was used instead of Compound C 129 as a light emitting host material when forming the emission layer.
- red organic electroluminescent devices (Examples 62 to 65) using the compounds (C 129, C 493, C 496 and C 498) according to the present invention as the light emitting layer, the conventional CBP material of the light emitting layer Compared with the red organic electroluminescent element (Comparative Example 2) used, it can be seen that it shows excellent performance in terms of efficiency and driving voltage.
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Abstract
The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and can provide an organic electroluminescent device with improved characteristics, such as luminous efficiency, driving voltage, and lifetime, by introducing a light emitting layer, which uses an indolophenanthridine-based compound as a host material, to the organic electro-luminescent device.
Description
본 발명은 유기 전계 발광 소자의 재료로 사용될 수 있는 신규 유기 화합물 및 이를 포함하여 소자의 발광효율, 구동전압, 수명 등이 향상되는 유기 전계 발광 소자에 관한 것이다. The present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage, lifespan, etc. of the device are improved.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'라 칭함)에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후, 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. Based on Bernanose's observation of organic thin-film luminescence in the 1950s, research on organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 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 the organic electroluminescent device, when a voltage is applied between 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 holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, 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 and the like according to its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대한 연구가 많이 진행되고 있다. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.
현재까지 정공 주입층, 정공 수송층, 정공 차단층, 전자 수송층으로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광 재료로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히, 발광 재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료들은 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red) 도판트 재료로 사용되고 있으며, 현재까지는 CBP가 인광 호스트 재료로 높은 특성을 나타내고 있다.To date, NPB, BCP, Alq 3 and the like are widely known as a hole injection layer, a hole transport layer, a hole blocking layer, and an electron transport layer, and anthracene derivatives are reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.
그러나, 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, OLED 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하는 실정이다. 따라서, 더욱 성능이 뛰어난 재료의 개발이 요구되고 있다.However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and very poor thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of the material which is more excellent in performance is desired.
본 발명은 높은 유리 전이온도로 인해 열적 안정성이 우수하면서, 정공과 전자의 결합력을 향상시킬 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a novel organic compound which is excellent in thermal stability due to a high glass transition temperature and can improve the binding force between holes and electrons.
또, 본 발명은 상기 신규 유기 화합물을 포함하여 구동전압, 발광효율 등이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In addition, an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
화학식 1 
Formula 1
상기 화학식 1에서,In Chemical Formula 1,
R1과 R2, R2과 R3 또는 R3와 R4 중 적어도 하나는 하기 화학식 2와 결합하여 축합 고리를 형성하고,At least one of R 1 and R 2 , R 2 and R 3, or R 3 and R 4 combine with Formula 2 to form a condensed ring,
화학식 2 
Formula 2
상기 화학식 2에서 점선은 화학식 1의 화합물과 축합이 이루어지는 부위이며,In FIG. 2, the dotted line represents a site where condensation occurs with the compound of Formula 1.
X1는 N 또는 CR9 이고,X 1 is N or CR 9 ,
X2는 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고,X 2 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
Y1 내지 Y8 은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 CR10이고, 각각의 R10은 동일하거나 상이할 수 있으며,Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10 , each R 10 may be the same or different,
R1 내지 R10은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 10 are the same or different and are each independently hydrogen, deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ alkynyl group of C 40 , C 6 ~ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group , C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 It is selected from the group consisting of an arylsilyl group, these may combine with adjacent groups to form a condensed ring And
Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group , nuclear atoms heteroaryl of 5 to 40 group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group , nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine A pin group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group,
상기 R1 내지 R10 및 Ar1 내지 Ar5에서, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때, 치환기가 복수개인 경우, 이들은 서로 동일하거나 또는 상이할 수 있다.In the R 1 to R 10 and Ar 1 to Ar 5 , C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 3 ~ C 40 cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 40 aryl boron group, a C 6 to C 40 arylphosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 C 40 alkynyl group, C 6 ~ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 40 group, and It may be substituted with one or more selected from the group consisting of C 6 ~ C 40 arylsilyl group. In this case, when there are a plurality of substituents, they may be the same or different from each other.
또한, 본 발명은 양극, 음극 및 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 1의 화합물을 포함하는 것이 특징인 유기 전계 발광 소자를 제공한다.In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises a compound of Formula 1 It is an organic electroluminescent device characterized by.
여기서, 상기 1층 이상의 유기물층 중 적어도 하나는 정공 주입층, 정공 수송층, 전자수송층, 전자주입층 및 발광층으로 구성된 군으로부터 선택될 수 있으며, 발광층인 것이 바람직하다. 이때, 상기 화학식 1로 표시되는 화합물은 청색, 녹색 또는 적색의 인광 호스트 재료이다.Here, at least one of the one or more organic material layers may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, it is preferable that the light emitting layer. In this case, the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.Since the compound represented by Chemical Formula 1 of the present invention is excellent in thermal stability and phosphorescence property, it may be used as a material of the organic material layer of the organic EL device. In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to a conventional host material can be manufactured, and further, performance And a full color display panel with greatly improved lifespan.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
<신규 화합물><New compound>
본 발명에 따른 신규 화합물은 인돌로페난트리딘 모이어티(indolophenanthridine moiety) 또는 벤조이미다졸로페난트리딘 모이어티(benzoimidazolophenanthridine moiety)의 말단에 인돌(indole) 모이어티가 융합되어 기본 골격을 이루며, 이러한 기본 골격에 다양한 치환체가 결합된 구조로서, 상기 화학식 1로 표시되는 것을 특징으로 한다.The novel compounds according to the present invention are indolophenanthridine moiety or benzoimidazolophenanthridine moiety in the end of the indole (indole) moiety is fused to form a basic skeleton, such As a structure in which various substituents are bonded to the basic skeleton, it is represented by the formula (1).
상기 화학식 1로 표시되는 화합물은 인돌로페난트리딘 모이어티(indolophenanthridine moiety) 또는 벤조이미다졸로페난트리딘 모이어티(benzoimidazolophenanthridine moiety)의 말단에 결합된 인돌(indole) 모이어티로 인해 넓은 밴드갭을 가질 뿐만 아니라, 다양한 방향족 환(aromatic ring) 치환체로 인해 분자 전체가 바이폴라(bipolar) 특성을 가지면서, 정공과 전자의 결합력을 높일 수 있다. 따라서 상기 화학식 1의 화합물은 유기 EL 소자의 인광특성을 개선함과 동시에 정공 주입 능력, 수송 능력 또는 발광효율도 개선할 수 있다. The compound represented by Formula 1 has a wide bandgap due to the indolophenanthridine moiety or the indole moiety bound to the terminal of the benzoimidazolophenanthridine moiety. In addition to having a variety of aromatic ring (aromatic ring) substituents, the entire molecule has a bipolar (bipolar) properties, it is possible to increase the binding force between the hole and the electron. Therefore, the compound of Formula 1 may improve the phosphorescence property of the organic EL device and also improve the hole injection ability, transport ability, or luminous efficiency.
또한, 인돌(indole) 모이어티에 도입된 다양한 방향족 환(aromatic ring) 치환체로 인해 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상될 수 있고, 이로 인해 종래 CBP(4,4-dicarbazolybiphenyl)보다 높은 열적 안정성을 가질 수 있다. 아울러, 상기 화학물은 유기물층의 결정화 억제에도 효과적이기 때문에, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 EL 소자는 내구성 및 수명 특성이 크게 향상될 수 있다.In addition, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, so that the glass transition temperature can be improved, and thus, the conventional CBP (4,4-dicarbazolybiphenyl) May have higher thermal stability. In addition, since the chemical is effective in suppressing crystallization of the organic material layer, the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifespan characteristics.
구체적으로, 본 발명의 화학식 1로 표시되는 화합물을 유기 EL 소자의 정공 주입/수송층의 재료로, 청색, 녹색 및/또는 적색의 인광 호스트 재료로 채택할 경우, 종래 CBP 대비 효율 및 수명 면에서 월등히 우수한 효과를 발휘할 수 있다. 따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 EL 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 이러한 유기 EL 소자 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화를 가져올 수 있다.Specifically, when the compound represented by the formula (1) of the present invention is adopted as a material of the hole injection / transport layer of the organic EL device as a phosphorescent host material of blue, green, and / or red, the efficiency and lifespan of the conventional CBP are excellent. It can exert an excellent effect. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and the improvement of the life of the organic EL device can lead to the maximization of the performance in the full color organic light emitting panel.
상기 화학식 2와 결합하여 축합고리가 형성된 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 8 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 이러한 화학식 3 내지 화학식 8 로 표시되는 화합물은 유기 EL 소자의 특성을 고려할 때 바람직하다.Compound represented by the formula (1) of the present invention in combination with the formula (2) in which the condensed ring is formed may be more specifically represented by a compound represented by any one of the following formula (3). Such compounds represented by the formulas (3) to (8) are preferred when considering the properties of the organic EL device.
화학식 3 
Formula 3
화학식 4 
Formula 4
화학식 5 
Formula 5
화학식 6 
Formula 6
화학식 7 
Formula 7
화학식 8 
Formula 8
상기 화학식 3 내지 8에서, In Chemical Formulas 3 to 8,
X1, X2, R1 내지 R8 및 Y1 내지 Y8은 각각 상기 화학식 1에서 정의된 바와 같다.X 1 , X 2, R 1 to R 8 and Y 1 to Y 8 are the same as defined in Chemical Formula 1, respectively.
보다 구체적으로, X1는 N 또는 CR9이고, X2는 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로부터 선택된다. 바람직하게는 X1이 N 또는 CR9이고, X2가 N(Ar1)인 경우이고, 더 바람직하게는 X1이 N이고, X2가 N(Ar1)이다.More specifically, X 1 is N or CR 9 and X 2 is selected from O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) . Preferably X 1 is N or CR 9 , X 2 is N (Ar 1 ), more preferably X 1 is N, and X 2 is N (Ar 1 ).
Y1 내지 Y8 은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 CR10 이고, 이때 각각의 R10은 동일하거나 상이할 수 있다. 바람직하게는 Y1 내지 Y8이 모두 CR10이고, 이때 각각의 R10은 동일하거나 상이할 수 있다.Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10, wherein each R 10 may be the same or different. Preferably Y 1 to Y 8 are all CR 10, wherein each R 10 may be the same or different.
또한, Ar1 내지 Ar5 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된다.In addition, Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 40 aryl amine group, a C 3 ~ C 40 cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ aryl boronic of C 40, a C 6 ~ C 40 Aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 It is selected from the group consisting of arylsilyl group.
이때 유기 EL 소자의 특성을 더 고려할 때, 상기 Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환되거나 비치환된 C6~C40의 아릴기, 또는 치환되거나 비치환된 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다. At this time, when considering the characteristics of the organic EL device, Ar 1 to Ar 5 are the same or different from each other, each independently substituted or unsubstituted C 6 ~ C 40 An aryl group, or a substituted or unsubstituted nuclear atom It is preferable that it is a heteroaryl group of the number 5-40.
아울러, 화학식 2와 축합고리를 비형성하는 치환기, 일례로, R1와 R2, R2과 R3, 및/또는 R3와 R4 중 적어도 하나를 제외하는 R1 내지 R10은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 또는 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다. In addition, substituents that form a condensed ring with Formula 2, for example, R 1 to R 10 excluding R 1 and R 2 , R 2 and R 3 , and / or at least one of R 3 and R 4 are the same as each other. or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ aryl of C 40 alkynyl group, C 6 ~ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, a C 3 ~ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ aryl of C 40 A phosphine group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group, or they can combine with adjacent groups to form a condensed ring.
본 발명에서, R1 내지 R10은 각각 독립적으로 수소, 중수소(D), 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기 및 치환 또는 비치환된 C6~C40의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다. In the present invention, R 1 to R 10 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ~ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms and It is preferably selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 arylamine group.
여기서, 상기 R1 내지 R10 및 Ar1 내지 Ar5에서, 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때 치환기가 복수개인 경우, 복수개의 치환기는 서로 동일하거나 또는 상이할 수 있다.Here, in the R 1 to R 10 and Ar 1 to Ar 5 , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of the , C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine is selected from pingi, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group consisting of Of at least one can be replaced. In this case, when there are a plurality of substituents, the plurality of substituents may be the same or different from each other.
상기 화학식 2와 결합하여 축합고리가 형성된 본 발명의 화학식 1로 표시되는 화합물은 보다 바람직하게는 하기 화학식 9 내지 화학식 20 중 어느 하나로 표시되는 화합물로 구체화될 수 있다. 이러한 화학식 9 내지 화학식 20으로 표시되는 화합물은 유기 EL 소자의 특성을 고려할 때 더욱 바람직하다.Compound represented by the formula (1) of the present invention in combination with the formula (2) formed a condensed ring may be more preferably embodied as a compound represented by any one of the following formulas (9) to (20). Such compounds represented by the formulas (9) to (20) are more preferable in consideration of the characteristics of the organic EL device.
화학식 9 
Formula 9
화학식 10 
Formula 10
화학식 11 
Formula 11
화학식 12 
Formula 12
화학식 13 
Formula 13
화학식 14 
Formula 14
화학식 15 
Formula 15
화학식 16 
Formula 16
화학식 17 
Formula 17
화학식 18 
Formula 18
화학식 19 
Formula 19
화학식 20 
Formula 20
상기 화학식 9 내지 20에서, R1 내지 R8 및 Ar1은 각각 상기 화학식 1에서 정의된 바와 같다.In Formulas 9 to 20, R 1 to R 8 and Ar 1 are as defined in Formula 1, respectively.
보다 구체적으로, Ar1 은 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된다.More specifically, Ar 1 is C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group, Nuclear atoms of 5 to 40 hetero Aryl group, C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3 to 40 hetero Cycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl It is selected from the group consisting of a phosphine oxide group and a C 6 -C 40 arylsilyl group.
이때 유기 EL 소자의 특성을 더 고려할 때, 상기 Ar1 은 치환되거나 비치환된 C6~C40의 아릴기, 또는 치환되거나 비치환된 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.At this time, when considering the characteristics of the organic EL device, Ar 1 is preferably a substituted or unsubstituted C 6 ~ C 40 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.
또한, 화학식 2와 축합고리를 비형성하는 치환기, 일례로, R1와 R2, R2과 R3, 및/또는 R3와 R4 중 적어도 하나를 제외하는 R1 내지 R8은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 또는 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다. In addition, the same each other, with a substituent, for example, which is not formed the formula (2) and the condensed ring, R 1 and R 2, R 2 and R 3, and / or R 3 and R 4 of R 1 to R 8, except for at least one or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ aryl of C 40 alkynyl group, C 6 ~ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, a C 3 ~ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ aryl of C 40 A phosphine group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group, or they can combine with adjacent groups to form a condensed ring.
본 발명에서, R1 내지 R8은 각각 독립적으로 수소, 중수소(D), 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 및 치환 또는 비치환된 C6~C40의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다. In the present invention, R 1 to R 8 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ~ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, And it is preferably selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 arylamine group.
여기서, 상기 R1 내지 R8 및 Ar1 내지 Ar5에서, 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때 치환기가 복수개인 경우, 복수개의 치환기는 서로 동일하거나 또는 상이할 수 있다.Here, in the R 1 to R 8 and Ar 1 to Ar 5 , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of the , C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine is selected from pingi, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group consisting of Of at least one can be replaced. In this case, when there are a plurality of substituents, the plurality of substituents may be the same or different from each other.
본 발명에 따른 화학식 1의 화합물에서, R1 내지 R10 및 Ar1 내지 Ar5는 각각 독립적으로, 수소 또는 하기 S1 내지 S204로 표시되는 치환체 군에서 선택되는 것이 바람직하나, 이에 한정되지는 않는다.In the compound of Formula 1 according to the present invention, R 1 to R 10 and Ar 1 to Ar 5 are each independently selected from hydrogen or a substituent group represented by S1 to S204, but are not limited thereto.
보다 바람직하게는 R1 내지 R10 및 Ar1 내지 Ar5 는 각각 독립적으로 수소 또는 하기 치환체 군에서 선택될 수 있다.More preferably, R 1 to R 10 and Ar 1 to Ar 5 may be each independently selected from hydrogen or the following substituent groups.
이상에서 설명한 본 발명의 화합물은 하기 예시된 구조들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compounds of the present invention described above can be further embodied in the structures illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
한편, 본 발명에서의 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있다.Meanwhile, "alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, and iso-amyl. And hexyl.
본 발명에서의 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있다.In the present invention, "alkenyl" is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.
본 발명에서의 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있다."Alkynyl" in the present invention is 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 thereof include ethynyl, 2-propynyl etc. are mentioned.
본 발명에서의 "아릴"은 단독 고리 또는 2 이상의 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 등을 들 수 있다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are pendant or condensed with each other may also be included. Examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.
본 발명에서의 "헤테로아릴"은 핵원자수 5 내지 40의 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 포함하는 것으로 해석한다. 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, 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. 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 or condensed with each other may be included, and is also construed to include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로 상기 R은 탄소수 5 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
본 발명에서의 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure. Interpret as included. Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있다."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 cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
본 발명에서의 "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 등을 들 수 있다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include morpholine, piperazine and the like.
본 발명에서의 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.
본 발명에서의 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명의 화학식 1의 화합물은 하기 합성예를 참조하여 다양하게 합성할 수 있다. 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.The compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
<유기 전계 발광 소자><Organic EL device>
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다. On the other hand, another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
구체적으로, 본 발명의 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 화합물, 바람직하게는 화학식 3 내지 화학식 8로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1의 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). In this case, the compound of Formula 1 may be used alone, or two or more may be mixed.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 이때, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1). At this time, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.
구체적으로, 본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 이와 같이, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.Specifically, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material. As such, when the compound of Formula 1 is included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로, 본 발명의 화학식 1로 표시되는 화합물은 발광층의 인광 호스트 재료로 이용될 수 있다. 한편, 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다. The structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be. Specifically, the compound represented by Formula 1 of the present invention may be used as a phosphorescent host material of the light emitting layer. On the other hand, the electron injection layer may be further stacked on the electron transport layer.
또한, 본 발명에 따른 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
본 발명에 따른 유기 전계 발광 소자는 상기 유기물층 중 1층 이상(예컨대, 발광층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 업계에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device according to the present invention may be formed using other materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It can be produced by forming an organic material 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, 이들에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
또, 양극 물질로는 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 한정되지 않는다.In addition, examples of the anode 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), indium zinc oxide (IZO); Combinations of metals and oxides 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 are not limited thereto.
또, 음극 물질로는 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 한정되지 않는다.In addition, the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질이 사용될 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials 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 with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[준비예 1] IPT-1의 합성Preparation Example 1 Synthesis of IPT-1
<단계 1> 4-(2-nitrophenyl)-1H-indole의 합성<Step 1> Synthesis of 4- (2-nitrophenyl) -1H-indole
질소 기류 하에서 4-bromo-1H-indole (17.25 g, 88.0 mmol), 2-nitrophenylboronic acid (16.1 g, 96.7 mmol), NaOH (10.6 g, 264.0 mmol)과 THF/H2O (1000 ml/500 ml)를 넣고 교반하였다. 40℃에서 Pd(PPh3)4 (5.1 g, 5 mol%)를 넣고, 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물인 4-(2-nitrophenyl)-1H-indole (16.4 g, 68.6 mmol, 수율 78 %)을 획득하였다. 4-bromo-1H-indole (17.25 g, 88.0 mmol), 2-nitrophenylboronic acid (16.1 g, 96.7 mmol), NaOH (10.6 g, 264.0 mmol) and THF / H 2 O (1000 ml / 500 ml) under nitrogen stream ) Was added and stirred. Pd (PPh 3 ) 4 (5.1 g, 5 mol%) was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, the target compound 4- (2-nitrophenyl) -1H-indole (16.4 g, 68.6 mmol, yield 78%) was obtained by column chromatography.
1H-NMR : δ 6.52 (d, 1H), 7.31 (m, 2H), 7.62 (m, 3H), 7.99 (m, 3H), 10.12 (s, 1H) 1 H-NMR: δ 6.52 (d, 1H), 7.31 (m, 2H), 7.62 (m, 3H), 7.99 (m, 3H), 10.12 (s, 1H)
<단계 2> 1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole의 합성<Step 2> Synthesis of 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole
질소 기류 하에서 4-(2-nitrophenyl)-1H-indole (14.8 g, 62.0 mmol), 1-bromo-2-iodobenzene (52.6 g, 186.0 mmol), Cu powder(0.40 g, 6.20 mmol), K2CO3(25.7 g, 186.0 mmol) 및 nitrobenzene(300 ml)를 혼합하고 190℃에서 12시간 동안 교반하였다.4- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol), 1-bromo-2-iodobenzene (52.6 g, 186.0 mmol), Cu powder (0.40 g, 6.20 mmol), K 2 CO under nitrogen stream 3 (25.7 g, 186.0 mmol) and nitrobenzene (300 ml) were mixed and stirred at 190 ° C. for 12 hours.
반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후, 컬럼크로마토그래피로 정제하여 목적 화합물인 1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole (15.8 g, 40.3 mmol, 수율 65%)을 얻었다.After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole (15.8 g, 40.3 mmol, 65% yield).
1H-NMR : δ 6.52 (d, 1H), 7.35 (m, 2H), 7.61 (m, 5H), 7.93 (m, 4H), 8.07 (d, 1H) 1 H-NMR: δ 6.52 (d, 1H), 7.35 (m, 2H), 7.61 (m, 5H), 7.93 (m, 4H), 8.07 (d, 1H)
<단계 3> 13-(2-nitrophenyl)indolo[1,2-f]phenanthridine의 합성Step 3 Synthesis of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine
질소 기류 하에서 1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole (13.8 g, 35.0 mmol), cesium fluoride (15.5 g, 105 mmol), Pd2(dba)3 (0.91 g, 0.875 mmol), dppp (0.7 g, 1.75 mmol)을 CH3CN (150 ml)와 Toluene (150 ml)에 넣고 교반하였다. 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (10.4 g, 35.0 mmol)를 CH3CN (75 ml)와 Toluene (75 ml)에 녹여 서서히 적가한 후 110℃에서 24시간 동안 교반하였다. 반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 13-(2-nitrophenyl)indolo[1,2-f]phenanthridine (7.21 g, 18.6 mmol, 수율 53%)을 얻었다.1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol), cesium fluoride (15.5 g, 105 mmol), Pd 2 (dba) 3 (0.91 g, 0.875 mmol) and dppp (0.7 g, 1.75 mmol) were added to CH 3 CN (150 ml) and Toluene (150 ml) and stirred. 2- (trimethylsilyl) phenyl trifluoromethanesulfonate (10.4 g, 35.0 mmol) was dissolved in CH 3 CN (75 ml) and Toluene (75 ml) and slowly added dropwise, followed by stirring at 110 ° C for 24 hours. After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.21 g, 18.6 mmol, 53% yield).
1H-NMR : δ 6.28 (s, 1H), 7.49 (m, 4H), 7.79 (m, 5H), 7.99 (m, 5H), 8.61 (d, 1H) 1 H-NMR: δ 6.28 (s, 1H), 7.49 (m, 4H), 7.79 (m, 5H), 7.99 (m, 5H), 8.61 (d, 1H)
<단계 4> IPT-1 의 합성Step 4 Synthesis of IPT-1
질소 기류 하에서 13-(2-nitrophenyl)indolo[1,2-f]phenanthridine (5.61 g, 14.4 mmol)과 triphenylphosphine (9.46 g, 36.1 mmol), 1,2-dichlorobenzene (50 ml)를 넣은 후 12시간 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgSO4로 물을 제거하고, 컬럼크로마토그래피를 이용하여 목적 화합물인 IPT-1 (3.95 g, 11.1 mmol, 수율 77 %)을 획득하였다. 12 hours after addition of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol), triphenylphosphine (9.46 g, 36.1 mmol) and 1,2-dichlorobenzene (50 ml) under nitrogen stream Stirred. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was removed with MgSO 4 water, and column chromatography was used to obtain the target compound IPT-1 (3.95 g, 11.1 mmol, yield 77%).
1H-NMR : δ 6.33 (s, 1H), 7.36 (m, 4H), 7.54 (m, 4H), 7.76 (m, 2H), 7.99 (m, 3H), 8.62 (d, 1H), 10.01 (s, 1H) 1 H-NMR: δ 6.33 (s, 1H), 7.36 (m, 4H), 7.54 (m, 4H), 7.76 (m, 2H), 7.99 (m, 3H), 8.62 (d, 1H), 10.01 ( s, 1 H)
[준비예 2] IPT-2와 IPT-3의 합성Preparation Example 2 Synthesis of IPT-2 and IPT-3
<단계 1> 5-(2-nitrophenyl)-1H-indole의 합성<Step 1> Synthesis of 5- (2-nitrophenyl) -1H-indole
4-bromo-1H-indole 대신 5-bromo-1H-indole (17.25 g, 88.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 5-(2-nitrophenyl)-1H-indole (15.7 g, 66.0 mmol, 수율 75 %)을 얻었다.Except for using 5-bromo-1H-indole (17.25 g, 88.0 mmol) instead of 4-bromo-1H-indole was carried out the same procedure as in <Step 1> of Preparation Example 1 to 5- (2-nitrophenyl) -1H-indole (15.7 g, 66.0 mmol, yield 75%) was obtained.
1H-NMR : δ 6.45 (d, 1H), 7.28 (d, 1H), 7.68 (m, 3H), 7.98 (m, 4H), 10.12 (s, 1H) 1 H-NMR: δ 6.45 (d, 1H), 7.28 (d, 1H), 7.68 (m, 3H), 7.98 (m, 4H), 10.12 (s, 1H)
<단계 2> 1-(2-bromophenyl)-5-(2-nitrophenyl)-1H-indole의 합성<Step 2> Synthesis of 1- (2-bromophenyl) -5- (2-nitrophenyl) -1H-indole
4-(2-nitrophenyl)-1H-indole 대신 5-(2-nitrophenyl)-1H-indole (14.8 g, 62.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 1-(2-bromophenyl)-5-(2-nitrophenyl)-1H-indole (16.5 g, 42.2 mmol, 수율 68%)을 얻었다.The same procedure as in <Step 2> of Preparation Example 1 was performed except that 5- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) -1H-indole. 1- (2-bromophenyl) -5- (2-nitrophenyl) -1H-indole (16.5 g, 42.2 mmol, yield 68%) was obtained.
1H-NMR : δ 6.51 (d, 1H), 7.48 (m, 3H), 7.61 (m, 4H), 7.98 (m, 4H), 8.18 (d, 1H) 1 H-NMR: δ 6.51 (d, 1H), 7.48 (m, 3H), 7.61 (m, 4H), 7.98 (m, 4H), 8.18 (d, 1H)
<단계 3> 12-(2-nitrophenyl)indolo[1,2-f]phenanthridine의 합성Step 3 Synthesis of 12- (2-nitrophenyl) indolo [1,2-f] phenanthridine
1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole 대신 1-(2-bromophenyl)-5-(2-nitrophenyl)-1H-indole (13.8 g, 35.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 12-(2-nitrophenyl)indolo[1,2-f]phenanthridine (7.48 g, 19.3 mmol, 수율 55%)을 얻었다.Use of 1- (2-bromophenyl) -5- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole A 12- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.48 g, 19.3 mmol, yield 55%) was obtained by the same procedure as in <Step 3> of Preparation Example 1, except.
1H-NMR : δ 6.28 (s, 1H), 7.48 (m, 2H), 7.64 (m, 6H), 7.98 (m, 6H), 8.61 (d, 1H) 1 H-NMR: δ 6.28 (s, 1H), 7.48 (m, 2H), 7.64 (m, 6H), 7.98 (m, 6H), 8.61 (d, 1H)
<단계 4> IPT-2과 IPT-3의 합성Step 4 Synthesis of IPT-2 and IPT-3
13-(2-nitrophenyl)indolo[1,2-f]phenanthridine 대신 12-(2-nitrophenyl)indolo[1,2-f]phenanthridine (5.61 g, 14.4 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 목적화합물 IPT-2 (1.90 g, 5.33 mmol, 수율 37 %)와 IPT-3 (1.80 g, 5.19 mmol, 수율 36 %)을 얻었다.Preparation Example 1 except 12- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) was used instead of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine The same procedure as in <Step 4> of to give the target compound IPT-2 (1.90 g, 5.33 mmol, 37% yield) and IPT-3 (1.80 g, 5.19 mmol, 36% yield).
IPT-2 의 1H-NMR : δ 6.28 (d, 1H), 7.48 (m, 6H), 7.79 (m, 4H), 8.03 (m, 3H), 8.61 (d, 1H), 10.07 (s, 1H) 1 H-NMR of IPT-2: δ 6.28 (d, 1H), 7.48 (m, 6H), 7.79 (m, 4H), 8.03 (m, 3H), 8.61 (d, 1H), 10.07 (s, 1H )
IPT-3 의 1H-NMR : δ 6.28 (d, 1H), 7.45 (m, 4H), 7.73 (m, 6H), 8.00 (m, 3H), 8.62 (d, 1H), 10.09 (s, 1H) 1 H-NMR of IPT-3: δ 6.28 (d, 1H), 7.45 (m, 4H), 7.73 (m, 6H), 8.00 (m, 3H), 8.62 (d, 1H), 10.09 (s, 1H )
[준비예 3] IPT-4와 IPT-5의 합성Preparation Example 3 Synthesis of IPT-4 and IPT-5
<단계 1> 6-(2-nitrophenyl)-1H-indole의 합성Step 1 Synthesis of 6- (2-nitrophenyl) -1H-indole
4-bromo-1H-indole 대신 6-bromo-1H-indole (17.25 g, 88.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 6-(2-nitrophenyl)-1H-indole (14.9 g, 62.5 mmol, 수율 71 %)을 얻었다.Except for using 6-bromo-1H-indole (17.25 g, 88.0 mmol) instead of 4-bromo-1H-indole was carried out the same procedure as in <Step 1> of Preparation Example 6 to 6- (2-nitrophenyl) -1H-indole (14.9 g, 62.5 mmol, yield 71%) was obtained.
1H-NMR : δ 6.45 (d, 1H), 7.27 (d, 1H), 7.69 (m, 3H), 7.99 (m, 3H), 8.18 (d, 1H), 10.11 (s, 1H) 1 H-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.69 (m, 3H), 7.99 (m, 3H), 8.18 (d, 1H), 10.11 (s, 1H)
<단계 2> 1-(2-bromophenyl)-6-(2-nitrophenyl)-1H-indole의 합성<Step 2> Synthesis of 1- (2-bromophenyl) -6- (2-nitrophenyl) -1H-indole
4-(2-nitrophenyl)-1H-indole 대신 6-(2-nitrophenyl)-1H-indole (14.8 g, 62.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 1-(2-bromophenyl)-6-(2-nitrophenyl)-1H-indole (15.3 g, 39.1 mmol, 수율 63%)을 얻었다.The same procedure as in <Step 2> of Preparation Example 1 was performed except that 6- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) -1H-indole. 1- (2-bromophenyl) -6- (2-nitrophenyl) -1H-indole (15.3 g, 39.1 mmol, 63% yield) was obtained.
1H-NMR : δ 6.50 (d, 1H), 7.33 (t, 1H), 7.56 (m, 6H), 7.98 (m, 3H), 8.44 (d, 1H) 1 H-NMR: δ 6.50 (d, 1H), 7.33 (t, 1H), 7.56 (m, 6H), 7.98 (m, 3H), 8.44 (d, 1H)
<단계 3> 11-(2-nitrophenyl)indolo[1,2-f]phenanthridine의 합성Step 3 Synthesis of 11- (2-nitrophenyl) indolo [1,2-f] phenanthridine
1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole 대신 1-(2-bromophenyl)-6-(2-nitrophenyl)-1H-indole (13.8 g, 35.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 11-(2-nitrophenyl)indolo[1,2-f]phenanthridine (7.48 g, 19.3 mmol, 수율 55%)을 얻었다.Use of 1- (2-bromophenyl) -6- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole Except for the same process as in <Step 3> of Preparation Example 1 except 11- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.48 g, 19.3 mmol, yield 55%) was obtained.
1H-NMR : δ 6.28 (d, 1H), 7.43 (m, 2H), 7.68 (m, 6H), 7.98 (m, 4H), 8.16 (d, 1H), 8.63 (d, 1H), 10.12 (d, 1H) 1 H-NMR: δ 6.28 (d, 1H), 7.43 (m, 2H), 7.68 (m, 6H), 7.98 (m, 4H), 8.16 (d, 1H), 8.63 (d, 1H), 10.12 ( d, 1H)
<단계 4> IPT-4과 IPT-5의 합성Step 4 Synthesis of IPT-4 and IPT-5
13-(2-nitrophenyl)indolo[1,2-f]phenanthridine 대신 11-(2-nitrophenyl)indolo[1,2-f]phenanthridine (5.61 g, 14.4 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 목적화합물 IPT-4 (1.80 g, 5.19 mmol, 수율 36 %)와 IPT-5 (1.95 g, 5.62 mmol, 수율 39 %)을 얻었다.Preparation Example 1 except 11- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) was used instead of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine The same procedure as in <Step 4> of to obtain the target compound IPT-4 (1.80 g, 5.19 mmol, 36% yield) and IPT-5 (1.95 g, 5.62 mmol, 39% yield).
IPT-4 의 1H-NMR : δ 6.28 (d, 1H), 7.43 (m, 5H), 7.73 (m, 4H), 8.00 (m, 2H), 8.11 (m, 2H), 8.61 (d, 1H), 10.08 (s, 1H) 1 H-NMR of IPT-4: δ 6.28 (d, 1H), 7.43 (m, 5H), 7.73 (m, 4H), 8.00 (m, 2H), 8.11 (m, 2H), 8.61 (d, 1H ), 10.08 (s, 1 H)
IPT-5 의 1H-NMR : δ 6.28 (d, 1H), 7.49 (m, 6H), 7.70 (m, 4H), 8.02 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H), 10.09 (s, 1H) 1 H-NMR of IPT-5: δ 6.28 (d, 1H), 7.49 (m, 6H), 7.70 (m, 4H), 8.02 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H ), 10.09 (s, 1H)
[준비예 4] IPT-6의 합성Preparation Example 4 Synthesis of IPT-6
<단계 1> 7-(2-nitrophenyl)-1H-indole의 합성Step 1 Synthesis of 7- (2-nitrophenyl) -1H-indole
4-bromo-1H-indole 대신 7-bromo-1H-indole (17.25 g, 88.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 7-(2-nitrophenyl)-1H-indole (16.5 g, 69.5 mmol, 수율 79 %)을 얻었다.Except for using 7-bromo-1H-indole (17.25 g, 88.0 mmol) instead of 4-bromo-1H-indole was carried out the same procedure as in <Step 1> of Preparation Example 7 to 7- (2-nitrophenyl) -1H-indole (16.5 g, 69.5 mmol, yield 79%) was obtained.
1H-NMR : δ 6.45 (d, 1H), 7.31 (m, 2H), 7.69 (t, 1H), 7.99 (m, 5H), 10.11 (s, 1H) 1 H-NMR: δ 6.45 (d, 1H), 7.31 (m, 2H), 7.69 (t, 1H), 7.99 (m, 5H), 10.11 (s, 1H)
<단계 2> 1-(2-bromophenyl)-7-(2-nitrophenyl)-1H-indole의 합성<Step 2> Synthesis of 1- (2-bromophenyl) -7- (2-nitrophenyl) -1H-indole
4-(2-nitrophenyl)-1H-indole 대신 7-(2-nitrophenyl)-1H-indole (14.8 g, 62.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 1-(2-bromophenyl)-7-(2-nitrophenyl)-1H-indole (16.5 g, 42.2 mmol, 수율 68%)을 얻었다.The same procedure as in <Step 2> of Preparation Example 1 was performed except that 7- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) -1H-indole. 1- (2-bromophenyl) -7- (2-nitrophenyl) -1H-indole (16.5 g, 42.2 mmol, yield 68%) was obtained.
1H-NMR : δ 6.51 (d, 1H), 7.31 (m, 2H), 7.51 (m, 2H), 7.61 (m, 3H), 7.98 (m, 4H), 8.28 (d, 1H) 1 H-NMR: δ 6.51 (d, 1H), 7.31 (m, 2H), 7.51 (m, 2H), 7.61 (m, 3H), 7.98 (m, 4H), 8.28 (d, 1H)
<단계 3> 10-(2-nitrophenyl)indolo[1,2-f]phenanthridine의 합성Step 3 Synthesis of 10- (2-nitrophenyl) indolo [1,2-f] phenanthridine
1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole 대신 1-(2-bromophenyl)-7-(2-nitrophenyl)-1H-indole (13.8 g, 35.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 10-(2-nitrophenyl)indolo[1,2-f]phenanthridine (8.02 g, 20.7 mmol, 수율 59%)을 얻었다.Use of 1- (2-bromophenyl) -7- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole Except for the same process as in <Step 3> of Preparation Example 1 except 10- (2-nitrophenyl) indolo [1,2-f] phenanthridine (8.02 g, 20.7 mmol, 59% yield) was obtained.
1H-NMR : δ 6.28 (d, 1H), 7.44 (m, 3H), 7.61 (m, 2H), 7.71 (m, 2H), 7.98 (m, 7H), 8.58 (d, 1H) 1 H-NMR: δ 6.28 (d, 1H), 7.44 (m, 3H), 7.61 (m, 2H), 7.71 (m, 2H), 7.98 (m, 7H), 8.58 (d, 1H)
<단계 4> IPT-6의 합성Step 4 Synthesis of IPT-6
13-(2-nitrophenyl)indolo[1,2-f]phenanthridine 대신 10-(2-nitrophenyl)indolo[1,2-f]phenanthridine (5.61 g, 14.4 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 목적화합물 IPT-6 (3.65 g, 10.2 mmol, 수율 71 %)를 얻었다.Preparation Example 1 except for using 10- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) instead of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine The target compound IPT-6 (3.65 g, 10.2 mmol, 71% yield) was obtained by the same procedure as in <Step 4>.
1H-NMR : δ 6.31 (d, 1H), 7.31 (m, 2H), 7.55 (m, 5H), 7.78 (m, 2H), 7.99 (m, 4H), 8.60 (d, 1H), 10.09 (s, 1H) 1 H-NMR: δ 6.31 (d, 1H), 7.31 (m, 2H), 7.55 (m, 5H), 7.78 (m, 2H), 7.99 (m, 4H), 8.60 (d, 1H), 10.09 ( s, 1 H)
[준비예 5] IPT-7와 IPT-8의 합성Preparation Example 5 Synthesis of IPT-7 and IPT-8
<단계 1> N-(2,5-dibromophenyl)phenanthridin-6-amine의 합성Step 1 Synthesis of N- (2,5-dibromophenyl) phenanthridin-6-amine
질소 기류 하에서 6-chlorophenanthridine(18.8 g, 88.0 mmol), 2,5-dibromoaniline(24.3 g, 96.7 mmol), 1000ml 의 diglyme 을 넣고 160℃에서 3시간 동안 교반하였다. 반응 종결 후 필터한 후, EA와 Hexane으로 재결정하여 목적 화합물인 N-(2,5-dibromophenyl)phenanthridin-6-amine (29.4 g, 68.6 mmol, 수율 78 %)을 획득하였다. 6-chlorophenanthridine (18.8 g, 88.0 mmol), 2,5-dibromoaniline (24.3 g, 96.7 mmol), and 1000 ml of diglyme were added under nitrogen stream and stirred at 160 ° C. for 3 hours. After completion of the reaction, filtered, and recrystallized with EA and Hexane to obtain the target compound N- (2,5-dibromophenyl) phenanthridin-6-amine (29.4 g, 68.6 mmol, yield 78%).
1H-NMR : δ 4.12 (s, 1H), 6.78 (m, 2H), 7.21 (d, 1H), 7.35 (m, 3H), 7.71 (m, 3H), 7.92 (d, 1H), 8.12 (d, 1H) 1 H-NMR: δ 4.12 (s, 1H), 6.78 (m, 2H), 7.21 (d, 1H), 7.35 (m, 3H), 7.71 (m, 3H), 7.92 (d, 1H), 8.12 ( d, 1H)
<단계 2> IPTN-Br 의 합성<Step 2> Synthesis of IPTN-Br
질소 기류 하에서 N-(2,5-dibromophenyl)phenanthridin-6-amine (37.2 g, 87.0 mmol), triphenylphosphine (4.5 g, 17 mmol), palladium acetate (1.2 g, 5 mmol), pstassium carbonate (36.0 g 260 mmol)을 1000 ml 의 toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 IPTN-Br (19.0 g, 54.8 mmol, 수율 63 %)을 획득하였다. N- (2,5-dibromophenyl) phenanthridin-6-amine (37.2 g, 87.0 mmol), triphenylphosphine (4.5 g, 17 mmol), palladium acetate (1.2 g, 5 mmol), pstassium carbonate (36.0 g 260) under nitrogen stream mmol) was added to 1000 ml of toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the organic layer filtered to obtain the target compound IPTN-Br (19.0 g, 54.8 mmol, 63% yield) by column chromatography.
1H-NMR : δ 7.41 (m, 4H), 7.65 (t, 1H), 7.79 (m, 3H), 7.99 (m, 2H), 8.62 (d, 1H) 1 H-NMR: δ 7.41 (m, 4H), 7.65 (t, 1H), 7.79 (m, 3H), 7.99 (m, 2H), 8.62 (d, 1H)
<단계 3> IPTN1의 합성Step 3 Synthesis of IPTN1
4-bromo-1H-indole 대신 IPTN-Br (30.6 g, 88.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 IPTN1 (24.3 g, 62.5 mmol, 수율 71 %)을 얻었다.Except for using IPTN-Br (30.6 g, 88.0 mmol) instead of 4-bromo-1H-indole was carried out the same procedure as in <Step 1> of Preparation Example 1 IPTN1 (24.3 g, 62.5 mmol, yield 71% )
1H-NMR : δ 7.47 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.99 (m, 6H), 8.28 (d, 1H), 8.62 (d, 1H) 1 H-NMR: δ 7.47 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.99 (m, 6H), 8.28 (d, 1H), 8.62 (d, 1H)
<단계 4> IPT-7과 IPT-8의 합성Step 4 Synthesis of IPT-7 and IPT-8
13-(2-nitrophenyl)indolo[1,2-f]phenanthridine 대신 IPTN1 (5.61 g, 14.4 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 목적화합물 IPT-7 (1.80 g, 5.19 mmol, 수율 36 %)와 IPT-8 (1.65 g, 4.76 mmol, 수율 33 %)을 얻었다.Except for using IPTN1 (5.61 g, 14.4 mmol) instead of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine, the same procedure as in <Step 4> of Preparation Example 1 was performed. 7 (1.80 g, 5.19 mmol, yield 36%) and IPT-8 (1.65 g, 4.76 mmol, yield 33%) were obtained.
IPT-7 의 1H-NMR : δ 7.31 (t, 1H), 7.47 (m, 3H), 7.73 (m, 6H), 8.00 (m, 2H), 8.11 (d, 1H), 8.61 (d, 1H), 10.07 (s, 1H) 1 H-NMR of IPT-7: δ 7.31 (t, 1H), 7.47 (m, 3H), 7.73 (m, 6H), 8.00 (m, 2H), 8.11 (d, 1H), 8.61 (d, 1H ), 10.07 (s, 1 H)
IPT-8 의 1H-NMR : δ 7.30 (t, 1H), 7.49 (m, 3H), 7.72 (m, 4H), 7.88 (d, 1H), 8.02 (m, 2H), 8.18 (m, 2H), 8.62 (d, 1H), 10.09 (s, 1H) 1 H-NMR of IPT-8: δ 7.30 (t, 1H), 7.49 (m, 3H), 7.72 (m, 4H), 7.88 (d, 1H), 8.02 (m, 2H), 8.18 (m, 2H ), 8.62 (d, 1H), 10.09 (s, 1H)
[준비예 6] IPT-9와 IPT-10의 합성Preparation Example 6 Synthesis of IPT-9 and IPT-10
<단계 1> 5-(5-chloro-2-nitrophenyl)-1H-indole의 합성Step 1 Synthesis of 5- (5-chloro-2-nitrophenyl) -1H-indole
2-nitrophenylboronic acid 대신 5-chloro-2-nitrophenylboronic acid (19.47 g, 96.7 mmol)을 사용하는 것을 제외하고는 준비예 2의 <단계 1>과 동일한 과정을 수행하여 5-(5-chloro-2-nitrophenyl)-1H-indole (17.0 g, 62.5 mmol, 수율 71 %)을 얻었다.Except for using 5-chloro-2-nitrophenylboronic acid (19.47 g, 96.7 mmol) instead of 2-nitrophenylboronic acid was carried out the same process as in <Step 1> of Preparation Example 2 to 5- (5-chloro-2- nitrophenyl) -1H-indole (17.0 g, 62.5 mmol, yield 71%) was obtained.
1H-NMR : δ 6.45 (d, 1H), 7.27 (d, 1H), 7.63 (m, 3H), 7.95 (m, 2H), 8.10 (d, 1H), 10.11 (s, 1H) 1 H-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.63 (m, 3H), 7.95 (m, 2H), 8.10 (d, 1H), 10.11 (s, 1H)
<단계 2> 1-(2-bromophenyl)-5-(5-chloro-2-nitrophenyl)-1H-indole의 합성<Step 2> Synthesis of 1- (2-bromophenyl) -5- (5-chloro-2-nitrophenyl) -1H-indole
4-(2-nitrophenyl)-1H-indole 대신 5-(5-chloro-2-nitrophenyl)-1H-indole (16.9 g, 62.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 1-(2-bromophenyl)-5-(5-chloro-2-nitrophenyl)-1H-indole (18.1 g, 42.2 mmol, 수율 68%)을 얻었다.<Step 2> of Preparation Example 1 except that 5- (5-chloro-2-nitrophenyl) -1H-indole (16.9 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) -1H-indole. The same procedure was followed to obtain 1- (2-bromophenyl) -5- (5-chloro-2-nitrophenyl) -1H-indole (18.1 g, 42.2 mmol, 68% yield).
1H-NMR : δ 6.50 (d, 1H), 7.31 (t, 1H), 7.54 (m, 5H), 7.99 (m, 3H), 8.44 (d, 1H) 1 H-NMR: δ 6.50 (d, 1H), 7.31 (t, 1H), 7.54 (m, 5H), 7.99 (m, 3H), 8.44 (d, 1H)
<단계 3> 12-(5-chloro-2-nitrophenyl)indolo[1,2-f]phenanthridine의 합성Step 3 Synthesis of 12- (5-chloro-2-nitrophenyl) indolo [1,2-f] phenanthridine
1-(2-bromophenyl)-4-(2-nitrophenyl)-1H-indole 대신 1-(2-bromophenyl)-5-(5-chloro-2-nitrophenyl)-1H-indole (15.0 g, 35.0 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 12-(5-chloro-2-nitrophenyl)indolo[1,2-f]phenanthridine (8.61 g, 20.4 mmol, 수율 58%)을 얻었다.1- (2-bromophenyl) -5- (5-chloro-2-nitrophenyl) -1H-indole (15.0 g, 35.0 mmol) instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole Except for using the same process as in <Step 3> of Preparation Example 1 12- (5-chloro-2-nitrophenyl) indolo [1,2-f] phenanthridine (8.61 g, 20.4 mmol, Yield 58 %) Was obtained.
1H-NMR : δ 6.25 (d, 1H), 7.47 (m, 2H), 7.64 (m, 5H), 7.99 (m, 4H), 8.16 (d, 1H), 8.68 (d, 1H), 10.12 (d, 1H) 1 H-NMR: δ 6.25 (d, 1H), 7.47 (m, 2H), 7.64 (m, 5H), 7.99 (m, 4H), 8.16 (d, 1H), 8.68 (d, 1H), 10.12 ( d, 1H)
<단계 4> IPT-9과 IPT-10의 합성Step 4 Synthesis of IPT-9 and IPT-10
13-(2-nitrophenyl)indolo[1,2-f]phenanthridine 대신 12-(5-chloro-2-nitrophenyl)indolo[1,2-f]phenanthridine (6.09 g, 14.4 mmol)을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 목적화합물 IPT-9 (1.80 g, 4.61 mmol, 수율 32 %)와 IPT-10 (2.19 g, 5.62 mmol, 수율 39 %)을 얻었다.Except for using 12- (5-chloro-2-nitrophenyl) indolo [1,2-f] phenanthridine (6.09 g, 14.4 mmol) instead of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine Was prepared in the same manner as in <Step 4> of Preparation Example 1 to obtain the target compound IPT-9 (1.80 g, 4.61 mmol, yield 32%) and IPT-10 (2.19 g, 5.62 mmol, yield 39%).
IPT-9 의 1H-NMR : δ 6.28 (d, 1H), 7.46 (m, 5H), 7.71 (m, 3H), 8.01 (m, 2H), 8.11 (m, 2H), 8.63 (d, 1H), 10.12 (s, 1H) 1 H-NMR of IPT-9: δ 6.28 (d, 1H), 7.46 (m, 5H), 7.71 (m, 3H), 8.01 (m, 2H), 8.11 (m, 2H), 8.63 (d, 1H ), 10.12 (s, 1H)
IPT-10 의 1H-NMR : δ 6.29 (d, 1H), 7.43 (m, 6H), 7.75 (m, 3H), 8.04 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H), 10.10 (s, 1H) 1 H-NMR of IPT-10: δ 6.29 (d, 1H), 7.43 (m, 6H), 7.75 (m, 3H), 8.04 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H ), 10.10 (s, 1H)
[합성예 1] C 1의 합성Synthesis Example 1 Synthesis of C 1
질소 기류 하에서 IPT-1 (3.56 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) 및 DMF(50 ml)를 혼합하고 상온에서 1시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 필터한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 C 1 (5.47 g, 수율 93%)를 얻었다.Under nitrogen stream, IPT-1 (3.56 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF ( 50 ml) were mixed and stirred at room temperature for 1 hour. After the reaction was completed, water was added to filter the solid compound, and purified by column chromatography to give the title compound C 1 (5.47 g, 93% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 2] C 2의 합성Synthesis Example 2 Synthesis of C 2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenylpyrimidine (2.67 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 2 (4.99 g, 수율 85%)을 얻었다.The same procedure as in Synthesis Example 1 was performed except that 2-chloro-4,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. C 2 (4.99 g, yield 85%) was obtained as the target compound.
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 3] C 17의 합성Synthesis Example 3 Synthesis of C 17
질소 기류 하에서 화합물인 IPT-1 (3.56 g, 10.00 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.66 g, 12.00 mmol), Cu powder(0.06 g, 1.00 mmol), K2CO3(2.76 g, 20.00 mmol), Na2SO4(2.84 g, 20.00 mmol) 및 nitrobenzene(50 ml)를 혼합하고 200℃에서 12시간 동안 교반하였다. IPT-1 (3.56 g, 10.00 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.00 mmol), Cu powder (0.06 g) under nitrogen stream , 1.00 mmol), K 2 CO 3 (2.76 g, 20.00 mmol), Na 2 SO 4 (2.84 g, 20.00 mmol) and nitrobenzene (50 ml) were mixed and stirred at 200 ° C. for 12 hours.
반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 C 17 (4.91 g, 수율 74%)을 얻었다. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound C 17 (4.91 g, 74% yield).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 4] C 19의 합성Synthesis Example 4 Synthesis of C 19
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenylpyridine (4.63 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 19 (4.17 g, 수율 63%)를 얻었다.Synthesis except using 2- (3-bromophenyl) -4,6-diphenylpyridine (4.63 g, 12.00 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Example 3 was performed to obtain C 19 (4.17 g, yield 63%) as a target compound.
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 5] C 25의 합성Synthesis Example 5 Synthesis of C 25
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (4.63 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 25 (4.17 g, 수율 63%)를 얻었다.2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.63 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine g, 12.00 mmol) was obtained in the same manner as in Synthesis Example 3 to obtain C 25 (4.17 g, yield 63%) of the title compound.
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 6] C 27의 합성Synthesis Example 6 Synthesis of C 27
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (4.63 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 27 (4.57 g, 수율 69%)을 얻었다.2- (4'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.63 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine g, 12.00 mmol) was obtained in the same manner as in Synthesis Example 3 to obtain C 27 (4.57 g, 69%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 7] C 57의 합성Synthesis Example 7 Synthesis of C 57
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 57 (5.52 g, 수율 94%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 57 (5.52 g, yield 94%).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 8] C 58의 합성Synthesis Example 8 Synthesis of C 58
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 58 (5.28 g, 수율 90%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 58 (5.28 g, 90% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 9] C 73의 합성Synthesis Example 9 Synthesis of C 73
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 73 (4.91 g, 수율 74%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 73 (4.91 g, yield 74%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 10] C 75의 합성Synthesis Example 10 Synthesis of C 75
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 75 (4.57 g, 수율 69%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 75 (4.57 g, 69% yield).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 11] C 81의 합성Synthesis Example 11 Synthesis of C 81
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 81 (4.57 g, 수율 63%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 81 (4.57 g, 63% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 12] C 83의 합성Synthesis Example 12 Synthesis of C 83
IPT-1 대신 IPT-2 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 83 (4.96 g, 수율 67%)을 얻었다.Except for using IPT-2 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 83 (4.96 g, 67% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 13] C 113의 합성Synthesis Example 13 Synthesis of C 113
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 113 (5.35 g, 수율 91%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 113 (5.35 g, 91% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 14] C 114의 합성Synthesis Example 14 Synthesis of C 114
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 114 (5.28 g, 수율 90%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 114 (5.28 g, 90% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 15] C 129의 합성Synthesis Example 15 Synthesis of C 129
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 129 (5.11 g, 수율 77%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 129 (5.11 g, yield 77%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 16] C 131의 합성Synthesis Example 16 Synthesis of C 131
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 131 (4.70 g, 수율 71%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 131 (4.70 g, 71% yield).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 17] C 137의 합성Synthesis Example 17 Synthesis of C 137
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 137 (5.03 g, 수율 68%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 137 (5.03 g, yield 68%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 18] C 139의 합성Synthesis Example 18 Synthesis of C 139
IPT-1 대신 IPT-3 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 139 (4.96 g, 수율 67%)을 얻었다.Except for using IPT-3 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 139 (4.96 g, 67% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 19] C 169의 합성Synthesis Example 19 Synthesis of C 169
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 169 (5.41 g, 수율 92%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 169 (5.41 g, 92% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 20] C 170의 합성Synthesis Example 20 Synthesis of C 170
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 170 (5.28 g, 수율 90%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 170 (5.28 g, 90% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 21] C 185의 합성Synthesis Example 21 Synthesis of C 185
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 185 (4.71 g, 수율 71%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 185 (4.71 g, yield 71%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 22] C 187의 합성Synthesis Example 22 Synthesis of C 187
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 187 (4.50 g, 수율 68%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 187 (4.50 g, yield 68%).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 23] C 193의 합성Synthesis Example 23 Synthesis of C 193
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 193 (5.03 g, 수율 68%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 193 (5.03 g, yield 68%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 24] C 195의 합성Synthesis Example 24 Synthesis of C 195
IPT-1 대신 IPT-4 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 195 (4.37 g, 수율 59%)을 얻었다.Except for using IPT-4 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 195 (4.37 g, 59% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 25] C 225의 합성Synthesis Example 25 Synthesis of C 225
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 225 (5.58 g, 수율 95%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 225 (5.58 g, yield 95%).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 26] C 226의 합성Synthesis Example 26 Synthesis of C 226
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 226 (5.46 g, 수율 93%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 226 (5.46 g, 93% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 27] C 241의 합성Synthesis Example 27 Synthesis of C 241
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 241 (5.24 g, 수율 79%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 241 (5.24 g, yield 79%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 28] C 243의 합성Synthesis Example 28 Synthesis of C 243
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 243 (5.29 g, 수율 80%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 243 (5.29 g, yield 80%).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 29] C 249의 합성Synthesis Example 29 Synthesis of C 249
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 249 (5.40 g, 수율 73%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 249 (5.40 g, 73% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 30] C 251의 합성Synthesis Example 30 Synthesis of C 251
IPT-1 대신 IPT-5 (3.56 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 251 (4.96 g, 수율 67%)을 얻었다.Except for using IPT-5 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 251 (4.96 g, 67% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 31] C 281의 합성Synthesis Example 31 Synthesis of C 281
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 281 (5.35 g, 수율 91%)을 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 281 (5.35 g, 91% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 32] C 282의 합성Synthesis Example 32 Synthesis of C 282
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 282 (5.46 g, 수율 93%)을 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 282 (5.46 g, 93% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 33] C 297의 합성Synthesis Example 33 Synthesis of C 297
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 297 (4.91 g, 수율 74%)을 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 297 (4.91 g, yield 74%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 34] C 299의 합성Synthesis Example 34 Synthesis of C 299
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 299 (5.36 g, 수율 81%)를 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 299 (5.36 g, yield 81%).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 35] C 305의 합성Synthesis Example 35 Synthesis of C 305
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 305 (5.70 g, 수율 77%)를 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 305 (5.70 g, yield 77%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 36] C 307의 합성Synthesis Example 36 Synthesis of C 307
IPT-1 대신 IPT-6 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 307 (4.96 g, 수율 67%)을 얻었다.Except for using IPT-6 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 307 (4.96 g, 67% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 37] C 337의 합성Synthesis Example 37 Synthesis of C 337
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 337 (5.35 g, 수율 91%)을 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 337 (5.35 g, 91% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 38] C 338의 합성Synthesis Example 38 Synthesis of C 338
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 338 (5.28 g, 수율 90%)을 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 338 (5.28 g, 90% yield).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 39] C 353의 합성Synthesis Example 39 Synthesis of C 353
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 353 (4.91 g, 수율 74%)을 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound C 353 (4.91 g, yield 74%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 40] C 355의 합성Synthesis Example 40 Synthesis of C 355
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 355 (4.65 g, 수율 76%)를 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 355 (4.65 g, yield 76%).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 41] C 361의 합성Synthesis Example 41 Synthesis of C 361
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 361 (5.70 g, 수율 77%)를 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 361 (5.70 g, yield 77%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 42] C 363의 합성Synthesis Example 42 Synthesis of C 363
IPT-1 대신 IPT-7 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 363 (5.25 g, 수율 71%)을 얻었다.Except for using IPT-7 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 363 (5.25 g, yield 71%).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 43] C 393의 합성Synthesis Example 43 Synthesis of C 393
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 393 (5.35 g, 수율 91%)을 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 393 (5.35 g, 91% yield).
GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol) GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)
[합성예 44] C 394의 합성Synthesis Example 44 Synthesis of C 394
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 C 394 (5.46 g, 수율 93%)를 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound C 394 (5.46 g, yield 93%).
GC-Mass (이론치: 586.68 g/mol, 측정치: 586 g/mol)GC-Mass (Theoretical value: 586.68 g / mol, Measured value: 586 g / mol)
[합성예 45] C 409의 합성Synthesis Example 45 Synthesis of C 409
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 C 409 (4.65 g, 수율 70%)를 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain the title compound C 409 (4.65 g, yield 70%).
GC-Mass (이론치: 663.77 g/mol, 측정치: 663 g/mol)GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)
[합성예 46] C 411의 합성Synthesis Example 46 Synthesis of C 411
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 C 411 (4.65 g, 수율 76%)을 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound C 411 (4.65 g, yield 76%).
GC-Mass (이론치: 661.79 g/mol, 측정치: 661 g/mol)GC-Mass (Theoretical value: 661.79 g / mol, Measured value: 661 g / mol)
[합성예 47] C 417의 합성Synthesis Example 47 Synthesis of C 417
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 417 (5.33 g, 수율 72%)을 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound C 417 (5.33 g, 72% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 48] C 419의 합성Synthesis Example 48 Synthesis of C 419
IPT-1 대신 IPT-8 (3.56 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 C 419 (5.40 g, 수율 73%)를 얻었다.Except for using IPT-8 (3.56 g, 10.00 mmol) in place of IPT-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound C 419 (5.40 g, 73% yield).
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 49] C 162의 합성Synthesis Example 49 Synthesis of C 162
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 (3-bromophenyl)triphenylsilane (4.98 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 162 (4.21 g, 수율 61%)를 얻었다.The same procedure as in Synthesis Example 15 was carried out except that (3-bromophenyl) triphenylsilane (4.98 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine. C 162 (4.21 g, yield 61%) was obtained.
GC-Mass (이론치: 690.90 g/mol, 측정치: 690 g/mol)GC-Mass (Theoretical value: 690.90 g / mol, Measured value: 690 g / mol)
[합성예 50] C 167의 합성Synthesis Example 50 Synthesis of C 167
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole (3.61 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 167 (3.75 g, 수율 65%)를 얻었다.Use 2- (4-bromophenyl) -5-phenyl-1,3,4-oxadiazole (3.61 g, 12.00 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 15 was carried out to obtain a target compound C 167 (3.75 g, yield 65%).
GC-Mass (이론치: 576.64 g/mol, 측정치: 576 g/mol)GC-Mass (Theoretical value: 576.64 g / mol, Measured value: 576 g / mol)
[합성예 51] C 168의 합성Synthesis Example 51 Synthesis of C 168
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole (4.52 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 168 (4.50 g, 수율 69%)를 얻었다.4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole (4.52 g, 12.00 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using mmol), the same process as in Synthesis Example 15 was carried out to obtain C 168 (4.50 g, 69% yield) of the title compound.
GC-Mass (이론치: 651.76 g/mol, 측정치: 651 g/mol)GC-Mass (Theoretical value: 651.76 g / mol, Measured value: 651 g / mol)
[합성예 52] C 458의 합성Synthesis Example 52 Synthesis of C 458
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)pyrimidine (4.59 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 458 (5.69 g, 수율 81%)를 얻었다.2-chloro-4- (3- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) pyrimidine (instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine 4.59 g, 12.00 mmol) was obtained in the same manner as in Synthesis Example 15 to obtain C 458 (5.69 g, yield 81%) as a target compound.
GC-Mass (이론치: 702.84 g/mol, 측정치: 702 g/mol)GC-Mass (Theoretical value: 702.84 g / mol, Measured value: 702 g / mol)
[합성예 53] C 477의 합성Synthesis Example 53 Synthesis of C 477
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 3-bromo-N,N-diphenylaniline (4.59 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 477 (3.90 g, 수율 65%)를 얻었다.Same as Synthesis Example 15 except that 3-bromo-N, N-diphenylaniline (4.59 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The process was carried out to obtain the title compound C 477 (3.90 g, yield 65%).
GC-Mass (이론치: 599.72 g/mol, 측정치: 599 g/mol)GC-Mass (Theoretical value: 599.72 g / mol, Measured value: 599 g / mol)
[합성예 54] C 480의 합성Synthesis Example 54 Synthesis of C 480
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 (3-bromophenyl)diphenylphosphineoxide (4.29 g, 12.00 mmol)를 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 480 (3.73 g, 수율 59%)를 얻었다.The same procedure as in Synthesis Example 15 was carried out except that (3-bromophenyl) diphenylphosphineoxide (4.29 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine. C 480 (3.73 g, 59% yield) as the target compound was obtained.
GC-Mass (이론치: 632.69 g/mol, 측정치: 632 g/mol)GC-Mass (Theoretical value: 632.69 g / mol, Measured value: 632 g / mol)
[합성예 55] C 483의 합성Synthesis Example 55 Synthesis of C 483
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-dip-tolyl-1,3,5-triazine (3.55 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 483 (3.76 g, 수율 61%)를 얻었다.Use 2-chloro-4,6-dip-tolyl-1,3,5-triazine (3.55 g, 12.00 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 15 was carried out to obtain C 483 (3.76 g, yield 61%) as the target compound.
GC-Mass (이론치: 615.72 g/mol, 측정치: 615 g/mol)GC-Mass (Theoretical value: 615.72 g / mol, Measured value: 615 g / mol)
[합성예 56] C 479의 합성Synthesis Example 56 Synthesis of C 479
질소 기류 하에서 IPT-3 (3.56 g, 10.00 mmol), Triethylamine (1.21 g, 12.00 mmol), chlorodiphenylborane (2.41 g, 12.00 mmol) 및 Toluene (50 ml)을 혼합하고 110℃에서 6시간 동안 교반하였다. 반응이 종결된 후 Toluene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 C 479 (2.29 g, 수율 44%)를 얻었다. Under nitrogen stream, IPT-3 (3.56 g, 10.00 mmol), Triethylamine (1.21 g, 12.00 mmol), chlorodiphenylborane (2.41 g, 12.00 mmol) and Toluene (50 ml) were mixed and stirred at 110 ° C. for 6 hours. After completion of the reaction, toluene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound C 479 (2.29 g, 44% yield).
GC-Mass (이론치: 520.43 g/mol, 측정치: 520 g/mol) GC-Mass (Theoretical value: 520.43 g / mol, Measured value: 520 g / mol)
[합성예 57] C 493의 합성Synthesis Example 57 Synthesis of C 493
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 493 (3.25 g, 수율 58%)를 얻었다.The same procedure as in Synthesis Example 15 was repeated except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine. C 493 (3.25 g, yield 58%) was obtained as the target compound.
GC-Mass (이론치: 560.65 g/mol, 측정치: 560 g/mol)GC-Mass (Theoretical value: 560.65 g / mol, Measured value: 560 g / mol)
[합성예 58] C 496의 합성Synthesis Example 58 Synthesis of C 496
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (4.40 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 496 (3.71 g, 수율 54%)를 얻었다.Use 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 15 was carried out to obtain C 496 (3.71 g, yield 54%) as a target compound.
GC-Mass (이론치: 686.80 g/mol, 측정치: 686 g/mol)GC-Mass (Theoretical value: 686.80 g / mol, Measured value: 686 g / mol)
[합성예 59] C 498의 합성Synthesis Example 59 Synthesis of C 498
2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(biphenyl-4-yl)-2-(4-chlorophenyl)quinazoline (4.71 g, 12.00 mmol)을 사용하는 것을 제외하고는 합성예 15와 동일한 과정을 수행하여 목적 화합물인 C 498 (4.21 g, 수율 59%)를 얻었다.4- (biphenyl-4-yl) -2- (4-chlorophenyl) quinazoline (4.71 g, 12.00 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for the same procedure as in Synthesis Example 15, the title compound C 498 (4.21 g, yield 59%) was obtained.
GC-Mass (이론치: 712.84 g/mol, 측정치: 712 g/mol)GC-Mass (Theoretical value: 712.84 g / mol, Measured value: 712 g / mol)
[합성예 60] C 509의 합성Synthesis Example 60 Synthesis of C 509
IPT-1 대신 IPT-9 (3.91 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 중간 화합물인 IPT-9-1 (5.38 g, 수율 77%)을 얻었다.Except for using IPT-9 (3.91 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain an intermediate compound IPT-9-1 (5.38 g, yield 77%).
질소 기류 하에서 5.38 g (7.70 mmol)의 4-bromo-1H-indole, 1.18 g (9.67 mmol)의 phenylboronic acid, 1.06 g (26.4 mmol)의 NaOH과 100 ml / 50 ml의 THF/H2O를 넣고 교반하였다. 40℃에서 0.51 g (5 mol%)의 Pd(PPh3)4를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 509 (4.73 g, 6.39 mmol, 수율 83 %)를 얻었다. Under nitrogen stream, add 5.38 g (7.70 mmol) of 4-bromo-1H-indole, 1.18 g (9.67 mmol) of phenylboronic acid, 1.06 g (26.4 mmol) of NaOH, and 100 ml / 50 ml of THF / H 2 O Stirred. 0.51 g (5 mol%) of Pd (PPh 3 ) 4 was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C 509 (4.73 g, 6.39 mmol, 83% yield) by column chromatography.
GC-Mass (이론치: 739.86 g/mol, 측정치: 739 g/mol)GC-Mass (Theoretical value: 739.86 g / mol, Measured value: 739 g / mol)
[합성예 61] C 513의 합성Synthesis Example 61 Synthesis of C 513
phenylboronic acid 대신 9-phenyl-9H-carbazol-3-ylboronic acid (2.78 g, 9.67 mmol)을 사용하는 것을 제외하고는 합성예 60과 동일한 과정을 수행하여 목적 화합물인 C 513 (5.34 g, 전체 수율 59%)을 얻었다.Except for using 9-phenyl-9H-carbazol-3-ylboronic acid (2.78 g, 9.67 mmol) instead of phenylboronic acid, the same procedure as in Synthesis Example 60 was carried out to obtain the target compound C 513 (5.34 g, overall yield 59 %) Was obtained.
GC-Mass (이론치: 905.05 g/mol, 측정치: 904 g/mol)GC-Mass (Theoretical value: 905.05 g / mol, Measured value: 904 g / mol)
[합성예 62] C 515의 합성Synthesis Example 62 Synthesis of C 515
IPT-1 대신 IPT-9 (3.91 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 중간 화합물인 IPT-9-1 (5.38 g, 수율 77%)을 얻었다.Except for using IPT-9 (3.91 g, 10.00 mmol) instead of IPT-1 was carried out in the same manner as in Synthesis Example 3 to obtain an intermediate compound IPT-9-1 (5.38 g, yield 77%).
질소 기류 하에서 6.98 g (10.00 mmol)의 4-bromo-1H-indole, 3.55 g (21.0 mmol)의 diphenylamine, Pd(dba)2 (0.22 g, 0.4 mmol), (t-Bu)3P (0.12 g, 0.6 mmol), sodium tert-butoxide (2.88 g, 30.0 mmol) 을 100 ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 515 (6.73 g, 8.1 mmol, 수율 81 %)를 얻었다. 6.98 g (10.00 mmol) of 4-bromo-1H-indole, 3.55 g (21.0 mmol) of diphenylamine, Pd (dba) 2 (0.22 g, 0.4 mmol), (t-Bu) 3 P (0.12 g) under nitrogen stream , 0.6 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C 515 (6.73 g, 8.1 mmol, yield 81%).
GC-Mass (이론치: 830.97 g/mol, 측정치: 830 g/mol)GC-Mass (Theoretical value: 830.97 g / mol, Measured value: 830 g / mol)
[합성예 63] C 525의 합성Synthesis Example 63 Synthesis of C 525
IPT-9 대신 IPT-10 (3.91 g, 10.00 mmol)을 사용하는 것과 phenylboronic acid 대신 dibenzo[b,d]thiophen-4-ylboronic acid (2.21 g, 9.67 mmol)을 사용하는 것을 제외하고는 합성예 60과 동일한 과정을 수행하여 목적 화합물인 C 525 (4.31 g, 전체 수율 51%)를 얻었다.Synthesis Example 60 except for using IPT-10 (3.91 g, 10.00 mmol) instead of IPT-9 and dibenzo [b, d] thiophen-4-ylboronic acid (2.21 g, 9.67 mmol) instead of phenylboronic acid To obtain the target compound C 525 (4.31 g, 51% overall yield) was carried out in the same process.
GC-Mass (이론치: 846.01 g/mol, 측정치: 845 g/mol)GC-Mass (Theoretical value: 846.01 g / mol, Measured value: 845 g / mol)
[합성예 64] C 527의 합성Synthesis Example 64 Synthesis of C 527
IPT-9 대신 IPT-10 (3.91 g, 10.00 mmol)을 사용하는 것과 diphenylamine 대신 diphenylborane (3.49 g, 21.0 mmol)을 사용하는 것을 제외하고는 합성예 62과 동일한 과정을 수행하여 목적 화합물인 C 527 (4.55 g, 전체 수율 55%)를 얻었다.Except for using IPT-10 (3.91 g, 10.00 mmol) instead of IPT-9 and diphenylborane (3.49 g, 21.0 mmol) instead of diphenylamine was carried out in the same manner as in Synthesis Example 62 to give the target compound C 527 ( 4.55 g, total yield 55%) was obtained.
GC-Mass (이론치: 827.78 g/mol, 측정치: 827 g/mol)GC-Mass (Theoretical value: 827.78 g / mol, Measured value: 827 g / mol)
[실시예 1 ~ 61] 녹색 유기 EL 소자의 제작Examples 1 to 61 Fabrication of Green Organic EL Device
합성예 1~56, 60~64에서 합성한 화합물 C 1 ~ C 527을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.Compounds C 1 to C 527 synthesized in Synthesis Examples 1 to 56 and 60 to 64 were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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 ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ C 1 ~ C 527의 각각의 화합물 + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / C 1 to C 527 each compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 ( An organic EL device was fabricated by stacking in the order of 30 nm) / LiF (1 nm) / Al (200 nm).
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
[비교예 1] 녹색 유기 EL 소자의 제작Comparative Example 1 Fabrication of Green Organic EL Device
발광층 형성시 발광 호스트 물질로서 화합물 C 1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 EL 소자를 제작하였다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 1 as a light emitting host material when forming the emission layer.
[평가예 1][Evaluation Example 1]
실시예 1 ~ 61 및 비교예 1에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic EL devices produced in Examples 1 to 61 and Comparative Example 1, the 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.
표 1
Table 1
| 샘플 | 호스트 | 구동 전압(V) | EL 피크(nm) | 전류효율(cd/A) |
| 실시예 1 | C 1 | 6.74 | 515 | 40.0 |
| 실시예 2 | C 2 | 6.46 | 518 | 41.8 |
| 실시예 3 | C 17 | 6.71 | 517 | 44.2 |
| 실시예 4 | C 19 | 6.79 | 515 | 41.7 |
| 실시예 5 | C 25 | 6.55 | 518 | 41.5 |
| 실시예 6 | C 27 | 6.69 | 515 | 42.7 |
| 실시예 7 | C 57 | 6.69 | 518 | 43.0 |
| 실시예 8 | C 58 | 6.70 | 517 | 43.3 |
| 실시예 9 | C 73 | 6.34 | 515 | 44.1 |
| 실시예 10 | C 75 | 6.70 | 518 | 41.4 |
| 실시예 11 | C 81 | 6.66 | 517 | 42.2 |
| 실시예 12 | C 83 | 6.65 | 518 | 43.1 |
| 실시예 13 | C 113 | 6.65 | 515 | 41.1 |
| 실시예 14 | C 114 | 6.71 | 518 | 42.0 |
| 실시예 15 | C 129 | 6.72 | 515 | 42.5 |
| 실시예 16 | C 131 | 6.72 | 518 | 41.3 |
| 실시예 17 | C 137 | 6.75 | 518 | 41.9 |
| 실시예 18 | C 139 | 6.73 | 517 | 41.6 |
| 실시예 19 | C 169 | 6.73 | 517 | 41.5 |
| 실시예 20 | C 170 | 6.48 | 517 | 41.4 |
| 실시예 21 | C 185 | 6.86 | 517 | 41.2 |
| 실시예 22 | C 187 | 6.61 | 518 | 41.1 |
| 실시예 23 | C 193 | 6.51 | 517 | 42.5 |
| 실시예 24 | C 195 | 6.77 | 515 | 43.1 |
| 실시예 25 | C 225 | 6.66 | 518 | 39.2 |
| 실시예 26 | C 226 | 6.65 | 518 | 41.3 |
| 실시예 27 | C 241 | 6.65 | 517 | 39.7 |
| 실시예 28 | C 243 | 6.64 | 515 | 38.9 |
| 실시예 29 | C 249 | 6.64 | 518 | 41.3 |
| 실시예 30 | C 251 | 6.63 | 518 | 41.3 |
| 실시예 31 | C 281 | 6.63 | 518 | 41.3 |
| 실시예 32 | C 282 | 6.62 | 518 | 41.2 |
| 실시예 33 | C 297 | 6.62 | 518 | 41.2 |
| 실시예 34 | C 299 | 6.62 | 517 | 42.9 |
| 실시예 35 | C 305 | 6.48 | 515 | 39.6 |
| 실시예 36 | C 307 | 6.86 | 518 | 40.4 |
| 실시예 37 | C 337 | 6.61 | 518 | 40.1 |
| 실시예 38 | C 338 | 6.70 | 517 | 40.8 |
| 실시예 39 | C 353 | 6.73 | 518 | 40.7 |
| 실시예 40 | C 355 | 6.75 | 518 | 40.5 |
| 실시예 41 | C 361 | 6.77 | 517 | 40.4 |
| 실시예 42 | C 363 | 6.76 | 515 | 41.7 |
| 실시예 43 | C 393 | 6.72 | 518 | 41.5 |
| 실시예 44 | C 394 | 6.70 | 515 | 42.7 |
| 실시예 45 | C 409 | 6.66 | 518 | 42.7 |
| 실시예 46 | C 411 | 6.81 | 518 | 43.1 |
| 실시예 47 | C 417 | 6.66 | 518 | 43.5 |
| 실시예 48 | C 419 | 6.81 | 518 | 41.4 |
| 실시예 49 | C 162 | 6.68 | 517 | 42.2 |
| 실시예 50 | C 167 | 6.66 | 517 | 42.0 |
| 실시예 51 | C 168 | 6.70 | 515 | 41.8 |
| 실시예 52 | C 458 | 6.70 | 518 | 42.0 |
| 실시예 53 | C 477 | 6.51 | 518 | 42.5 |
| 실시예 54 | C 480 | 6.77 | 517 | 41.3 |
| 실시예 55 | C 483 | 6.46 | 515 | 41.3 |
| 실시예 56 | C 479 | 6.71 | 518 | 41.6 |
| 실시예 57 | C 509 | 6.72 | 518 | 41.5 |
| 실시예 58 | C 513 | 6.70 | 515 | 42.7 |
| 실시예 59 | C 515 | 6.51 | 518 | 42.5 |
| 실시예 60 | C 525 | 6.70 | 518 | 42.0 |
| 실시예 61 | C 527 | 6.70 | 517 | 40.8 |
| 비교예 1 | CBP | 6.93 | 516 | 38.2 |
| Sample | Host | Drive voltage (V) | EL peak (nm) | Current efficiency (cd / A) |
| Example 1 | C 1 | 6.74 | 515 | 40.0 |
| Example 2 | C 2 | 6.46 | 518 | 41.8 |
| Example 3 | C 17 | 6.71 | 517 | 44.2 |
| Example 4 | C 19 | 6.79 | 515 | 41.7 |
| Example 5 | C 25 | 6.55 | 518 | 41.5 |
| Example 6 | C 27 | 6.69 | 515 | 42.7 |
| Example 7 | C 57 | 6.69 | 518 | 43.0 |
| Example 8 | C 58 | 6.70 | 517 | 43.3 |
| Example 9 | C 73 | 6.34 | 515 | 44.1 |
| Example 10 | C 75 | 6.70 | 518 | 41.4 |
| Example 11 | C 81 | 6.66 | 517 | 42.2 |
| Example 12 | C 83 | 6.65 | 518 | 43.1 |
| Example 13 | C 113 | 6.65 | 515 | 41.1 |
| Example 14 | C 114 | 6.71 | 518 | 42.0 |
| Example 15 | C 129 | 6.72 | 515 | 42.5 |
| Example 16 | C 131 | 6.72 | 518 | 41.3 |
| Example 17 | C 137 | 6.75 | 518 | 41.9 |
| Example 18 | C 139 | 6.73 | 517 | 41.6 |
| Example 19 | C 169 | 6.73 | 517 | 41.5 |
| Example 20 | C 170 | 6.48 | 517 | 41.4 |
| Example 21 | C 185 | 6.86 | 517 | 41.2 |
| Example 22 | C 187 | 6.61 | 518 | 41.1 |
| Example 23 | C 193 | 6.51 | 517 | 42.5 |
| Example 24 | C 195 | 6.77 | 515 | 43.1 |
| Example 25 | C 225 | 6.66 | 518 | 39.2 |
| Example 26 | C 226 | 6.65 | 518 | 41.3 |
| Example 27 | C 241 | 6.65 | 517 | 39.7 |
| Example 28 | C 243 | 6.64 | 515 | 38.9 |
| Example 29 | C 249 | 6.64 | 518 | 41.3 |
| Example 30 | C 251 | 6.63 | 518 | 41.3 |
| Example 31 | C 281 | 6.63 | 518 | 41.3 |
| Example 32 | C 282 | 6.62 | 518 | 41.2 |
| Example 33 | C 297 | 6.62 | 518 | 41.2 |
| Example 34 | C 299 | 6.62 | 517 | 42.9 |
| Example 35 | C 305 | 6.48 | 515 | 39.6 |
| Example 36 | C 307 | 6.86 | 518 | 40.4 |
| Example 37 | C 337 | 6.61 | 518 | 40.1 |
| Example 38 | C 338 | 6.70 | 517 | 40.8 |
| Example 39 | C 353 | 6.73 | 518 | 40.7 |
| Example 40 | C 355 | 6.75 | 518 | 40.5 |
| Example 41 | C 361 | 6.77 | 517 | 40.4 |
| Example 42 | C 363 | 6.76 | 515 | 41.7 |
| Example 43 | C 393 | 6.72 | 518 | 41.5 |
| Example 44 | C 394 | 6.70 | 515 | 42.7 |
| Example 45 | C 409 | 6.66 | 518 | 42.7 |
| Example 46 | C 411 | 6.81 | 518 | 43.1 |
| Example 47 | C 417 | 6.66 | 518 | 43.5 |
| Example 48 | C 419 | 6.81 | 518 | 41.4 |
| Example 49 | C 162 | 6.68 | 517 | 42.2 |
| Example 50 | C 167 | 6.66 | 517 | 42.0 |
| Example 51 | C 168 | 6.70 | 515 | 41.8 |
| Example 52 | C 458 | 6.70 | 518 | 42.0 |
| Example 53 | C 477 | 6.51 | 518 | 42.5 |
| Example 54 | C 480 | 6.77 | 517 | 41.3 |
| Example 55 | C 483 | 6.46 | 515 | 41.3 |
| Example 56 | C 479 | 6.71 | 518 | 41.6 |
| Example 57 | C 509 | 6.72 | 518 | 41.5 |
| Example 58 | C 513 | 6.70 | 515 | 42.7 |
| Example 59 | C 515 | 6.51 | 518 | 42.5 |
| Example 60 | C 525 | 6.70 | 518 | 42.0 |
| Example 61 | C 527 | 6.70 | 517 | 40.8 |
| Comparative Example 1 | CBP | 6.93 | 516 | 38.2 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물(C 1 ~ C 527)을 발광층으로 사용한 녹색 유기 EL 소자(실시예 1 내지 61)는, 종래 CBP를 사용한 녹색 유기 EL 소자(비교예 1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1, the green organic EL device (Examples 1 to 61) using the compounds (C 1 to C 527) according to the present invention as a light emitting layer is a green organic EL device (Comparative Example 1) using a conventional CBP. Compared with, it can be seen that the better performance in terms of efficiency and driving voltage.
[실시예 62 ~ 65] 적색 유기 EL 소자의 제작Examples 62 to 65 Fabrication of Red Organic EL Device
합성예 15, 57~59에서 합성한 화합물 C 129, C 493, C 496 및 C 498을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.Compounds C 129, C 493, C 496 and C 498 synthesized in Synthesis Examples 15, 57 to 59 were subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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 ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ C 129, C 493, C 496, C 498의 각각의 화합물 + 10 % (piq)2Ir(acac) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / C 129, C 493, C 496, C 498 + 10% (piq) 2 Ir (acac) (300nm) / An organic electroluminescent device was manufactured by laminating in the order of BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
[비교예 2] 적색 유기 EL 소자의 제작Comparative Example 2 Fabrication of Red Organic EL Device
발광층 형성시 발광 호스트 물질로서 화합물 C 129 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 62와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 62, except that CBP was used instead of Compound C 129 as a light emitting host material when forming the emission layer.
상기 실시예 62 ~ 65 및 비교예 2에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), CBP and BCP used in Examples 62 to 65 and Comparative Example 2 are as follows.
[평가예 2][Evaluation Example 2]
실시예 62 ~ 65 및 비교예 2에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each of the organic EL devices manufactured in Examples 62 to 65 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
표 2
TABLE 2
| 샘플 | 호스트 | 구동 전압(V) | 전류효율(cd/A) |
| 실시예 62 | C 129 | 4.6 | 13.3 |
| 실시예 63 | C 493 | 4.63 | 12.9 |
| 실시예 64 | C 496 | 4.6 | 12.7 |
| 실시예 65 | C 498 | 4.59 | 13 |
| 비교예 2 | CBP | 5.25 | 8.2 |
| Sample | Host | Drive voltage (V) | Current efficiency (cd / A) |
| Example 62 | C 129 | 4.6 | 13.3 |
| Example 63 | C 493 | 4.63 | 12.9 |
| Example 64 | C 496 | 4.6 | 12.7 |
| Example 65 | C 498 | 4.59 | 13 |
| Comparative Example 2 | CBP | 5.25 | 8.2 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물(C 129, C 493, C 496 및 C 498)을 발광층으로 사용한 적색 유기 전계 발광 소자(실시예 62~65)는, 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예 2)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2, red organic electroluminescent devices (Examples 62 to 65) using the compounds (C 129, C 493, C 496 and C 498) according to the present invention as the light emitting layer, the conventional CBP material of the light emitting layer Compared with the red organic electroluminescent element (Comparative Example 2) used, it can be seen that it shows excellent performance in terms of efficiency and driving voltage.
Claims (8)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,R1과 R2, R2과 R3 또는 R3와 R4 중 적어도 하나는 하기 화학식 2와 결합하여 축합 고리를 형성하고,At least one of R 1 and R 2 , R 2 and R 3, or R 3 and R 4 combine with Formula 2 to form a condensed ring,[화학식 2][Formula 2]
상기 화학식 2에서 점선은 화학식 1의 화합물과 축합이 이루어지는 부위이며,In FIG. 2, the dotted line represents a site where condensation occurs with the compound of Formula 1.X1 는 N 또는 CR9 이고,X 1 is N or CR 9 ,X2는 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고,X 2 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),Y1 내지 Y8 은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 CR10 이고, 각각의 R10은 동일하거나 상이할 수 있으며,Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10 , each R 10 may be the same or different,R1 내지 R10은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 10 are the same or different and are each independently hydrogen, deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ alkynyl group of C 40 , C 6 ~ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group , C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 It is selected from the group consisting of an arylsilyl group, these may combine with adjacent groups to form a condensed ring AndAr1 내지 Ar5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group , nuclear atoms heteroaryl of 5 to 40 group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group , nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine A pin group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group,상기 R1 내지 R10 및 Ar1 내지 Ar5에서, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있다.In the R 1 to R 10 and Ar 1 to Ar 5 , C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 3 ~ C 40 cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 40 aryl boron group, a C 6 to C 40 arylphosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 C 40 alkynyl group, C 6 ~ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 40 group, and It may be substituted with one or more selected from the group consisting of C 6 ~ C 40 arylsilyl group. - 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 8 중 어느 하나로 표시되는 것을 특징으로 하는 화합물.The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 8.[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
화학식 3 내지 8에서,In Chemical Formulas 3 to 8,X1, X2, R1 내지 R8 및 Y1 내지 Y8은 각각 청구항 1에서 정의한 바와 같다.X 1 , X 2, R 1 to R 8 and Y 1 to Y 8 are as defined in claim 1, respectively. - 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 9 내지 20 중 어느 하나로 표시되는 것을 특징으로 하는 화합물.The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 9 to 20.[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
[화학식 18][Formula 18]
[화학식 19][Formula 19]
[화학식 20][Formula 20]
상기 화학식 9 내지 20에서,In Chemical Formulas 9 to 20,R1 내지 R8 및 Ar1은 각각 청구항 1에서 정의한 바와 같다.R 1 to R 8 and Ar 1 are each as defined in claim 1. - 제1항에 있어서, 상기 Ar1은 치환 또는 비치환된 C6~C40의 아릴기, 또는 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기이며, According to claim 1, Ar 1 is a substituted or unsubstituted C 6 ~ C 40 aryl group, or substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,상기 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물.The C 6 ~ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine groups, C 3 to C 40 cycloalkyl groups, heterocycloalkyl groups of 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 40 of the arylboronic group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group substituted with one or more substituents selected from the group consisting of groups or Compound which is unsubstituted.
- 제1항에 있어서, 상기 R1 내지 R10은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소(D), 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 및 치환 또는 비치환된 C6~C40의 아릴아민기로 이루어진 군에서 선택되며,The method of claim 1, wherein R 1 to R 10 are the same as or different from each other, and each independently hydrogen, deuterium (D), a substituted or unsubstituted C 6 ~ C 40 aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 40 atoms, and a substituted or unsubstituted C 6 to C 40 arylamine group,상기 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물.The C 6 ~ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms, the C 6 ~ C 40 arylamine group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 6 ~ C 40 aryl group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ~ aryloxy C 40, C 1 ~ C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 groups of an alkyl boron, C 6 ~ C 40 from the arylboronic group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ arylsilyl group the group consisting of C 40 of Compound unsubstituted or substituted with one or more substituents selected.
- 제1항에 있어서, 상기 Ar1 내지 Ar5 및 R1 내지 R10은 각각 독립적으로 수소, 또는 하기 S1 내지 S204로 표시되는 치환체 군에서 선택되는 것을 특징으로 하는 화합물.The method of claim 1, wherein Ar 1 to Ar 5 and R 1 to R 10 are each independently selected from hydrogen or a substituent group represented by S1 to S204.
- 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode;상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 6, characterized in that the organic electroluminescent device.
- 제7항에 있어서, 상기 화합물을 포함하는 적어도 하나의 유기물층은 발광층인 것을 특징으로 하는 유기 전계 발광 소자.The organic electroluminescent device according to claim 7, wherein at least one organic material layer including the compound is a light emitting layer.
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