WO2014065501A1 - Organic compound and organic electroluminescent element comprising same - Google Patents
Organic compound and organic electroluminescent element comprising same Download PDFInfo
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- WO2014065501A1 WO2014065501A1 PCT/KR2013/007955 KR2013007955W WO2014065501A1 WO 2014065501 A1 WO2014065501 A1 WO 2014065501A1 KR 2013007955 W KR2013007955 W KR 2013007955W WO 2014065501 A1 WO2014065501 A1 WO 2014065501A1
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- substituted
- unsubstituted
- aryl
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- 150000002894 organic compounds Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 239000010410 layer Substances 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000004429 atom Chemical group 0.000 claims description 35
- -1 alkyl boron Chemical compound 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000005104 aryl silyl group Chemical group 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 11
- 125000005264 aryl amine group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 239000011368 organic material Substances 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 description 221
- 238000003786 synthesis reaction Methods 0.000 description 221
- 239000000463 material Substances 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 35
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XIYPPJVLAAXYAB-UHFFFAOYSA-N 2-bromo-6-phenylpyridine Chemical compound BrC1=CC=CC(C=2C=CC=CC=2)=N1 XIYPPJVLAAXYAB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 5
- KHNXJQYQESYSFH-UHFFFAOYSA-N tert-butyl 22-azahexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1(21),2(10),4,6,8,11,15(20),16,18-nonaene-22-carboxylate Chemical compound C12=CC=CC=C2CC2=C1C=C1CCC3=C4C1=C2N(C(=O)OC(C)(C)C)C4=CC=C3 KHNXJQYQESYSFH-UHFFFAOYSA-N 0.000 description 5
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- 0 Cc1c(*)c(C(*)C(*)c2c3c([n]4[Al]C)c(*c5c-6c(*)c(*)c(*)c5*)c-6c2*)c3c4c1* Chemical compound Cc1c(*)c(C(*)C(*)c2c3c([n]4[Al]C)c(*c5c-6c(*)c(*)c(*)c5*)c-6c2*)c3c4c1* 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
- 239000010949 copper Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 3
- IOYQZGLOLAUKED-UHFFFAOYSA-N 2-(3-bromo-5-methylphenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound CC1=CC(Br)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 IOYQZGLOLAUKED-UHFFFAOYSA-N 0.000 description 3
- OOHRWLAEJIWHQB-UHFFFAOYSA-N 2-(3-bromo-5-phenylphenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C(N=1)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 OOHRWLAEJIWHQB-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CKOJZXHTFBJBAO-UHFFFAOYSA-N tert-butyl 15-[2-(chloromethyl)phenyl]-15-azatetracyclo[10.2.1.05,14.08,13]pentadeca-1(14),2,4,6,8(13),11-hexaene-3-carboxylate Chemical compound C1=2C=3C4=CCCC=3C=CC1=CC(C(=O)OC(C)(C)C)=CC=2N4C1=CC=CC=C1CCl CKOJZXHTFBJBAO-UHFFFAOYSA-N 0.000 description 3
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- SAEMLZTYQDFJNB-UHFFFAOYSA-N 15-azatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6,8(13),10,12(15)-heptaene Chemical compound C1=C(C2=C34)CC=CC2=NC3=CC=CC4=C1 SAEMLZTYQDFJNB-UHFFFAOYSA-N 0.000 description 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
- BMDXLLRSUSWZIS-UHFFFAOYSA-N 2-[3-bromo-5-(trifluoromethyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound FC(F)(F)C1=CC(Br)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BMDXLLRSUSWZIS-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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 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 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 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 compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- DHPRFQITOQHVNY-UHFFFAOYSA-N tert-butyl 15-(2-nitrophenyl)-15-azatetracyclo[10.2.1.05,14.08,13]pentadeca-1(14),2,4,6,8(13),11-hexaene-3-carboxylate Chemical compound C1=2C=3C4=CCCC=3C=CC1=CC(C(=O)OC(C)(C)C)=CC=2N4C1=CC=CC=C1[N+]([O-])=O DHPRFQITOQHVNY-UHFFFAOYSA-N 0.000 description 2
- XWVHCOWPKDTZBR-UHFFFAOYSA-N tert-butyl 22-azahexacyclo[17.2.1.03,11.04,9.012,21.015,20]docosa-1(21),2,4(9),5,7,10,12,15(20),18-nonaene-5-carboxylate Chemical compound C1=2C(C(=O)OC(C)(C)C)=CC=CC=2C=C2C1=CC(N1)=C3C2=CCC2=C3C1=CCC2 XWVHCOWPKDTZBR-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 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 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CQKUYQQUGYUDPD-UHFFFAOYSA-N (4-bromophenyl)-diphenylborane Chemical compound C1=CC(Br)=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 CQKUYQQUGYUDPD-UHFFFAOYSA-N 0.000 description 1
- YNLBCLNFEOKEHA-UHFFFAOYSA-N (4-bromophenyl)-diphenylphosphane Chemical compound C1=CC(Br)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNLBCLNFEOKEHA-UHFFFAOYSA-N 0.000 description 1
- HHKQVJLWIUUHPB-UHFFFAOYSA-N (4-chlorophenyl)-triphenylsilane Chemical compound C1=CC(Cl)=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HHKQVJLWIUUHPB-UHFFFAOYSA-N 0.000 description 1
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- BYDMGWHTARYHKO-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenylpyrimidine Chemical compound BrC1=CC=CC(C=2N=C(C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BYDMGWHTARYHKO-UHFFFAOYSA-N 0.000 description 1
- FWESVNIHRVSDDV-UHFFFAOYSA-N 2-(4-bromophenyl)triphenylene Chemical group C1=CC(Br)=CC=C1C1=CC=C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)C3=C1 FWESVNIHRVSDDV-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
- MJFJRWWQVIQVQD-UHFFFAOYSA-N 2-[4-(3-bromophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2C=CC(=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MJFJRWWQVIQVQD-UHFFFAOYSA-N 0.000 description 1
- INJYATWDDJSOIP-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyridine Chemical compound N=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 INJYATWDDJSOIP-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 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
- 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
- HGBMQIPSGRZZEM-UHFFFAOYSA-N 3-bromo-9-(4,6-diphenyl-1,3,5-triazin-2-yl)carbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C(N=1)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 HGBMQIPSGRZZEM-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- GJXAVNQWIVUQOD-UHFFFAOYSA-N 4-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(Br)=CC=C2 GJXAVNQWIVUQOD-UHFFFAOYSA-N 0.000 description 1
- 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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
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Abstract
The present invention relates to a novel compound and an organic electroluminescent element comprising the same, and at least one organic material layer, preferably an emission layer, comprises the novel compound thereby significantly improving light-emitting efficiency, a driving voltage and a life span of the element.
Description
본 발명은 유기 전계 발광 소자용 재료로서 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 which can be used as a material for an organic electroluminescent device, and an organic electroluminescent device in which the luminous efficiency, driving voltage, lifetime, etc. of the device are improved.
유기 전계 발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어졌으며, 비로소 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 EL 소자가 제시되었다. 이후, 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. The study of organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting with Bernanose's observation of organic thin-film emission. In 1987, Tang presented 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 evolved to introduce 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 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 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 from the anode, and electrons are injected into the organic material layer from 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 a 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 materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission 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 낮고 열적 안정성이 매우 좋지 않아 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 the glass transition temperature is low and thermal stability is not very good, and thus it is not satisfactory in terms of lifespan in OLED devices. Therefore, the development of more excellent materials is required.
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.
또한, 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 the following formula (1).
화학식 1 
Formula 1
상기 화학식 1에서,In Chemical Formula 1,
R6 및 R7 또는 R7 및 R8 중 적어도 하나는 하기 화학식 2와 축합 고리를 형성하고,At least one of R 6 and R 7 or R 7 and R 8 forms a condensed ring with the following Chemical Formula 2,
화학식 2 
Formula 2
상기 화학식 2에서,In Chemical Formula 2,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4), Si(Ar5)(Ar6), P(Ar7) 및 B(Ar8)로 구성된 군으로부터 선택되고, X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ) and B (Ar 8 ) Become,
R1 내지 R12 는 서로 같거나 또는 상이하고, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, R 1 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, substituted or unsubstituted C 1 -C 40 alkyl boron group, a substituted or unsubstituted C 6 ~ C 60 aryl group of boron, a substituted or unsubstituted C 6 ~ C 60 aryl phosphine group, a substituted or unsubstituted C 6 ~ C 60 aryl phosphine oxide group is selected from the pin, and the group consisting of a substituted or unsubstituted C 6 ~ C 60 aryl amine, these are combined tile adjacent may form a condensed ring,
Ar1 내지 Ar8 은 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 구성된 군으로부터 선택되며, Ar 1 to Ar 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, substituted or unsubstituted C 1 -C 40 alkyl Boron group, substituted or unsubstituted C 6 ~ C 60 aryl boron group, substituted or unsubstituted C 6 ~ C 60 arylphosphine group, substituted or unsubstituted C 6 ~ C 60 aryl phosphine oxide group, and a substituted or unsubstituted C 6 ~ C 60 arylamine group,
상기 R1~R12 및 Ar1~Ar8에서, '치환 또는 비치환된'이라는 용어가 기재된 치환기, 일례로 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴아민기는, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, 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, C6~C40의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다. 이때 복수 개의 치환기가 도입되는 경우, 이들 치환기는 서로 동일하거나 또는 상이할 수 있다.In R 1 to R 12 and Ar 1 to Ar 8 , substituents having the term 'substituted or unsubstituted' are described, for example, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group , An alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group, an arylamine group are each independently deuterium, halogen, cyano group, nitro A group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a nuclear atom having 5 to 40 heteroaryl groups, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 40 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine group, C 6 of the C 60 of ~ C 60 O Phosphine which may be substituted with one or more substituents selected from oxide groups, and C 6 ~ C 60 aryl group consisting of an amine group. In this case, when a plurality of substituents are introduced, these substituents may be the same or different from each other.
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device comprising a compound represented by the formula (1).
여기서, 상기 1층 이상의 유기물층 중 적어도 하나는 정공 주입층, 정공 수송층 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 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 1 로 표시되는 신규 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층에 적용될 수 있다.Since the novel compound represented by Chemical Formula 1 of the present invention is excellent in thermal stability and phosphorescence property, it can be applied to the light emitting layer of the organic EL device.
따라서, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 물질로 사용할 경우, 종래 호스트 물질에 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 패널을 제조할 수 있다.Therefore, 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 the 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 발명은 종래 유기 EL 소자용 재료 [예: 4,4-dicarbazolybiphenyl (이하, 'CBP'로 표시함)] 보다 분자량이 클 뿐만 아니라, 넓은 에너지 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있는 상기 화학식 1로 표시되는 화합물을 제공하는 것을 특징으로 한다. The present invention not only has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], but also has a wide energy band gap to increase the bonding force between holes and electrons. It can be characterized in that it provides a compound represented by the formula (1).
본 발명에 따라 상기 화학식 1로 표시되는 신규 화합물은, 카바졸(carbazole) 기본 골격에 인돌기(indole)가 융합되어 있으며, 여기에 여러 치환체에 의해 에너지 레벨이 조절됨으로써, 넓은 밴드갭 (sky blue ~ red)을 갖게 된다. 이러한 화합물을 유기 EL 소자에 이용할 경우, 소자의 인광 특성을 개선함과 동시에 정공 주입 능력 및/또는 수송 능력, 효율(발광효율, 전력효율), 구동전압, 수명 특성, 휘도 등이 개선될 수 있다. 따라서, 발광층 뿐만 아니라 여러 치환체의 도입으로 인해 정공 수송층, 정공 주입층 등으로도 응용될 수 있다. 특히, 상기 화합물은 카바졸 기본 골격에 인돌기가 융합되어 있는 구조적 특이성으로 인해, 넓은 밴드갭을 가지면서 정공과 전자의 결합력을 높일 수 있기 때문에, 종래 CBP에 비해 발광층의 호스트 재료로서의 우수한 특성을 나타낼 수 있다.According to the present invention, the novel compound represented by Chemical Formula 1 has an indole fused to a carbazole basic skeleton, and energy levels are controlled by various substituents, thereby wide bandgap (sky blue ~ red). When such a compound is used in an organic EL device, the phosphorescence property of the device may be improved, and the hole injection ability and / or transport capacity, efficiency (luminescence efficiency, power efficiency), driving voltage, lifetime characteristics, luminance, etc. may be improved. . Therefore, the light emitting layer may be applied to a hole transport layer, a hole injection layer, etc. due to the introduction of various substituents. In particular, the compound exhibits excellent properties as a host material of the light emitting layer as compared to the conventional CBP, because the compound has a wide bandgap and can enhance the bond strength between holes and electrons due to the structural specificity in which indole groups are fused to the carbazole base skeleton. Can be.
또한, 인돌기가 융합된 카바졸 기본 골격에, 다수 도입된 다양한 방향족 환(aromatic ring) 치환체로 인해 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상되고, 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다. In addition, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the carbazole basic skeleton in which the indole group is fused, thereby improving the glass transition temperature, thereby resulting in higher thermal stability than the conventional CBP. Can have
아울러 본 발명의 신규 화합물은, 카바졸 환 내부에 사이클로헥실이 융합됨으로써, 화합물의 열안정성 향상이 도모되고, 그 화합물을 포함하는 유기막의 안정성, 결정화 억제 면에서도 효과가 있다. 따라서, 본 발명의 화합물을 포함하는 유기 EL 소자는 내구성 및 수명 특성을 크게 향상시킬 수 있다. Moreover, the cyclohexyl fused to the inside of a carbazole ring can improve the thermal stability of a compound, and the novel compound of this invention is also effective in the stability of the organic film containing this compound, and the suppression of crystallization. Therefore, the organic EL device containing the compound of the present invention can greatly improve durability and lifespan characteristics.
추가적으로, 본 발명에 따른 화학식 1의 화합물을 유기 EL 소자의 정공 주입/수송층, 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 발명에 따른 화합물은 유기 EL 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 특히 이러한 소자의 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.In addition, when the compound of Formula 1 according to the present invention is adopted as a hole injection / transport layer, blue, green, and / or red phosphorescent host material of an organic EL device, the compound of Formula 1 may have an excellent effect on efficiency and lifetime compared to conventional CBP. have. Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and the life of the organic EL device, and in particular, the life of the device has a great effect in maximizing the performance in the full color organic light emitting panel.
본 발명에 따른 화학식 1로 표시되는 화합물에서, 상기 화학식 2와 축합고리를 형성하는 치환기, 일례로 R6와 R7 및/또는 R7와 R8을 제외하는 R1 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.In the compound represented by Formula 1 according to the present invention, substituents forming a condensed ring with Formula 2, for example, R 1 to R 12 excluding R 6 and R 7 and / or R 7 and R 8 are the same as each other, or Different, each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 -C 40 alkyl group, substituted or unsubstituted C 2 -C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryl Groups, substituted or unsubstituted heteroaryl groups having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy groups, substituted or unsubstituted C 6 to C 60 aryloxy groups, substituted or the unsubstituted C 1 ~ C 40 alkyl silyl group, a substituted or unsubstituted C 6 ~ C 60 aryl silyl group, a substituted addition Unsubstituted C 1 ~ C 40 alkyl boron group, a substituted or unsubstituted C with 6 ~ C 60 aryl boron group, an aryl phosphonic a substituted or unsubstituted C 6 ~ C 60 ring pingi of, substituted or unsubstituted C 6 of An arylphosphine oxide group of ˜C 60 , and a substituted or unsubstituted C 6 ˜C 60 arylamine group, which may combine with an adjacent group to form a condensed ring.
이때, R6와 R7 및/또는 R7와 R8을 제외하는 R1 내지 R12는 수소, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기인 경우가 바람직하다.At this time, R 1 to R 12 excluding R 6 and R 7 and / or R 7 and R 8 are hydrogen, a substituted or unsubstituted C 6 ~ C 60 aryl group, substituted or unsubstituted 5 to 5 nuclear atoms It is preferable when it is a heteroaryl group of 60.
한편, 상기 화학식 2에서, 상기 점선은 화학식 1의 화합물과 축합이 이루어지는 부위를 의미한다.On the other hand, in Formula 2, the dotted line means a site where the condensation is made with the compound of Formula 1.
본 발명에 따른 화학식 2에서, X는 O, S, Se, N(Ar2), C(Ar3)(Ar4), Si(Ar5)(Ar6), P(Ar7) 및 B(Ar8)로 구성된 군에서 선택되며, 바람직하게는 O, S, N(Ar2), C(Ar3)(Ar4)에서 선택될 수 있으며, 더욱 바람직하게는 N(Ar2)이다. In Formula 2 according to the present invention, X is O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ) and B ( Ar 8 ), preferably selected from O, S, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), and more preferably N (Ar 2 ).
상기 화학식 2에서, Ar1 내지 Ar8 은 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 구성된 군으로부터 선택될 수 있다. In Formula 2, Ar 1 to Ar 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 ~ C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 of the alkynyl group, a substituted or unsubstituted C 3 ~ C 40 cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero Cycloalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or Unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to C 40 alkylsilyl group, substituted or unsubstituted C 6 to C 60 arylsilyl group, substituted or unsubstituted C 1 ~ C 40 alkyl boron group, a substituted or unsubstituted C 6 ~ C 60 aryl boron group, a substituted or unsubstituted C 6 ~ C 60 aryl phosphine , It may be selected from the aryl phosphine oxide group, and a substituted or unsubstituted C 6 ~ C 60 aryl group consisting of an amine group of a substituted or unsubstituted C 6 ~ C 60.
이때 넓은 밴드갭과 열안정성을 고려했을 때, 상기 Ar1 은 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기가 바람직하다. 또한 상기 Ar2 내지 Ar8은 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기가 바람직하다. At this time, considering the wide bandgap and thermal stability, Ar 1 is preferably a substituted or unsubstituted C 6 ~ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms. In addition, Ar 2 to Ar 8 is a substituted or unsubstituted C 1 ~ C 40 Alkyl group, a substituted or unsubstituted C 6 ~ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms desirable.
본 발명의 화학식 1로 표기되는 화합물에서, X는 N(Ar2)이고, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되는 것이 바람직하다. 여기서, 상기 C6~C40의 아릴기, 핵원자수 5~40의 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, 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, C6~C40의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환되거나 또는 비치환될 수 있으며, 이때 복수 개의 치환기가 도입되는 경우 이들 치환기는 서로 동일하거나 또는 상이할 수 있다. In the compound represented by Formula 1 of the present invention, X is N (Ar 2 ), Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 to C 40 aryl group, and a substituted or unsubstituted nucleus. It is preferably selected from the group consisting of heteroaryl groups having 5 to 40 atoms. Here, the C 6 ~ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alke 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, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 40 arylsilyl group , a C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 of the It may be unsubstituted or substituted with one or more substituents selected from the group consisting of arylamine groups, wherein when a plurality of substituents are introduced, these substituents may be the same or different from each other.
본 발명에 따른 화학식 1의 화합물의 치환체인, R1 내지 R12, Ar1 내지 Ar8는 각각 독립적으로 수소, 또는 하기 치환체(작용기) 그룹, 일례로 S1 ~ S192로부터 선택되는 것이 바람직하며, 특히 R1 내지 R12, Ar1 및 Ar2은 수소 또는 하기 치환체 군(S1 ~ S192)으로부터 선택되는 것이 더욱 바람직하다. 그러나 이에 한정되지는 않는다. 다만, 상기 정의된 R1 내지 R12에서, 화학식 2와 축합고리를 형성하는 치환기, 일례로 R6와 R7 및/또는 R7와 R8는 제외된다. R 1 to R 12 , Ar 1 to Ar 8, which are substituents of the compound of formula 1 according to the present invention, are each independently selected from hydrogen or the following substituent (functional group) group, for example, S1 to S192, particularly R 1 to R 12 , Ar 1 and Ar 2 are more preferably selected from hydrogen or the following substituent groups (S1 to S192). However, it is not limited thereto. However, in R 1 to R 12 defined above, substituents forming a condensed ring with Formula 2, for example, R 6 and R 7 and / or R 7 and R 8 are excluded.
본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 6 중 어느 하나의 화학식으로 표시되는 화합물로 보다 구체화될 수 있다. The compound represented by the formula (1) of the present invention can be more specifically embodied by the compound represented by the formula of any one of formulas (3) to (6).
화학식 3 
Formula 3
화학식 4 
Formula 4
화학식 5 
Formula 5
화학식 6 
Formula 6
상기 화학식 3 내지 화학식 6 에서,In Chemical Formulas 3 to 6,
X, R1 내지 R12, Ar1 내지 Ar8은 각각 화학식 1에서 정의된 바와 동일하다.X, R 1 to R 12 , Ar 1 to Ar 8 are the same as defined in Chemical Formula 1.
상기 화학식 3 내지 화학식 6으로 표시되는 화합물의 구체적인 예로는 하기 화학식으로 표시되는 화합물 군이 있다.Specific examples of the compound represented by Formula 3 to Formula 6 include a compound group represented by the following formula.
상기 예시된 화학식에서, Ar1~Ar8, R1~R12는 각각 화학식 1에서 정의된 바와 동일하다. In the above exemplified formulas, Ar 1 to Ar 8 and R 1 to R 12 are the same as defined in Formula 1, respectively.
전술한 화학식에서, X가 N(Ar2)인 경우, Ar1 및 Ar2는 서로 같거나 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되고, In the above formula, when X is N (Ar 2 ), Ar 1 and Ar 2 are the same as or different from each other, each independently represent a substituted or unsubstituted C 6 ~ C 40 aryl group, and a substituted or unsubstituted Selected from the group consisting of heteroaryl groups having 5 to 40 nuclear atoms,
R1 내지 R12는 서로 같거나 동일하며, 각각 독립적으로 수소 또는 S1 ~ S192로 구성된 치환체 군으로부터 선택되는 것이 바람직하며, 수소 또는 하기 예시되는 치환체 군에서 선택되는 것이 더욱 바람직하다.R 1 to R 12 are the same as or identical to each other, and are each independently selected from hydrogen or a substituent group consisting of S1 to S192, and more preferably selected from hydrogen or a substituent group illustrated below.
또한 X가 C(Ar3)(Ar4), Si(Ar5)(Ar6), P(Ar7), B(Ar8)인 경우, Ar3 내지 Ar8는 서로 같거나 동일하며, 각각 독립적으로 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기로 이루어진 군에서 선택되는 것이 바람직하고, 특히 메틸기 또는 페닐기일 때 더욱 바람직하다. 여기서, R1 내지 R12는 서로 같거나 동일하며, 각각 독립적으로 수소 또는 S1 ~ S192로 구성된 치환체 군으로부터 선택되는 것이 바람직하며, 수소 또는 하기 예시되는 치환체 군에서 선택되는 것이 더욱 바람직하다.In addition, when X is C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ), B (Ar 8 ), Ar 3 to Ar 8 are the same or the same as each other, It is preferably selected from the group consisting of C 1 to C 40 alkyl groups, substituted or unsubstituted C 6 to C 60 aryl groups, and particularly preferably methyl or phenyl. Herein, R 1 to R 12 are the same as or the same as each other, and are each independently selected from hydrogen or a substituent group consisting of S1 to S192, and more preferably selected from hydrogen or a substituent group illustrated below.
본 발명에서 사용된 "비치환된 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 포함한다. As used herein, "unsubstituted alkyl" is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl and the like.
"비치환된 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) 등이 있으며, 이에 한정되는 것은 아니다. “Unsubstituted alkenyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, examples of which include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like, but are not limited thereto.
"비치환된 알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에타인일(ethynyl), 2-프로파인일(2-propynyl) 등이 있는데, 이에 제한되는 것은 아니다."Unsubstituted alkynyl" is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, examples being ethynyl , 2-propynyl, and the like, but is not limited thereto.
"비치환된 아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태로 부착될 수 있다. 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 포함되며 이에 한정되는 것은 아니다."Unsubstituted aryl" means a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or condensed form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
"비치환된 헤테로아릴"은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태로 부착될 수 있고, 나아가 아릴기와의 축합된 형태도 포함하는 것으로 해석된다. 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 고리를 포함하고, 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등도 포함하는 것으로 해석한다."Unsubstituted heteroaryl" 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. It is understood that two or more rings may be attached in a simple or condensed form with each other, and further include condensed forms with aryl groups. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
"비치환된 아릴옥시"는 RO-로 표시되는 1가의 치환기로서, 상기 R은 탄소수 5 내지 60의 아릴이다. 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다."Unsubstituted aryloxy" is a monovalent substituent represented by RO-, wherein R is an aryl having 5 to 60 carbon atoms. Examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
"비치환된 알킬옥시"는 R′O-로 표시되는 1가의 치환기로서, 상기 R′는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 포함될 수 있으며 이에 한정되지는 않는다. "Unsubstituted 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 alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
"비치환된 아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다."Unsubstituted arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.
"비치환된 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) 등이 포함되지만 이에 한정되는 것은 아니다. "Unsubstituted cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
"비치환된 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 또는 S와 같은 헤테로 원자로 치환된다. 이의 비제한적인 예로는 모르폴린, 피페라진 등이 있다."Unsubstituted heterocycloalkyl" 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 or S Is substituted with a hetero atom such as Non-limiting examples thereof include morpholine, piperazine and the like.
"알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다."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.
"축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). 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 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3로 표시되는 화합물 내지 화학식 6으로 표시되는 화합물 중 어느 하나 이상을 포함한다. 이때, 상기 화학식 3 내지 화학식 6으로 표시되는 화합물은 단독으로 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer. Is a compound represented by Formula 1, preferably includes any one or more of the compound represented by Formula 3 to the compound represented by Formula 6. At this time, the compounds represented by Formula 3 to Formula 6 may be used alone or in combination of two or more.
여기서, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 바람직하게는 정공 주입/수송층, 발광층 또는 전자수송층일 수 있고, 보다 바람직하게는 발광층일 수 있다.Here, the one or more organic material layers 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, preferably a hole injection / transport layer, a light emitting layer or an electron transport layer, more preferably It may be a light emitting layer.
본 발명의 일례에 따르면, 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 호스트로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다. 상기 화학식 1로 표시되는 화합물은 청색, 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 발광 소자에 포함될 수 있다. According to one embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1). As such, when the compound of Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved. The compound represented by Chemical Formula 1 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, or a dopant material.
전술한 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. 이때, 본 발명의 화합물은 발광층의 인광 호스트로 이용될 수 있다. 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다. The structure of the organic EL device according to the present invention described above 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. In this case, the compound of the present invention may be used as a phosphorescent host of the light emitting layer. An 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 1층 이상의 유기물층 (예컨대, 발광층, 정공수송층 및/또는 전자수송층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device according to the present invention is known in the art, except that the at least one organic material layer (eg, the light emitting layer, the hole transport layer and / or the electron transport layer) is formed to include the compound represented by Formula 1 above. It can be prepared by forming other organic material layers and electrodes using materials and methods that are present.
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, 이들에만 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.
사용 가능한 양극 물질의 비제한적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지 않는다.Non-limiting examples of anode materials that can be used include metals such as vanadium, chromium, copper, zinc, 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.
사용 가능한 음극 물질의 비제한적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지 않는다.Non-limiting examples of negative electrode materials that can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys 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 준비예 및 합성예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 준비예 및 합성예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 준비예 및 합성예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Preparation Examples and Synthesis Examples. However, the following Preparation Examples and Synthesis Examples are merely illustrative of the present invention and the present invention is not limited by the following Preparation Examples and Synthesis Examples.
[준비예 1] IC-1과 IC-2의 합성Preparation Example 1 Synthesis of IC-1 and IC-2
<단계 1> 4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole의 합성<Step 1> Synthesis of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole
질소 기류 하에서 4-bromo-2,6-dihydro-1H-benzo[def]carbazole (3.38 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder(0.15 g, 2.48 mmol), K2CO3(3.42 g, 24.79 mmol), Na2SO4(3.53 g, 24.79 mmol) 및 nitrobenzene(100 ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. 4-bromo-2,6-dihydro-1H-benzo [def] carbazole (3.38 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder (0.15 g, 2.48 mmol), K under nitrogen stream 2 CO 3 (3.42 g, 24.79 mmol), Na 2 SO 4 (3.53 g, 24.79 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 h.
반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole (3.06 g, 8.80 mmol, 수율 71%)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 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (3.06 g, 8.80 mmol, 71% yield).
1H-NMR : δ 2.83 (m, 4H), 7.03 (m, 2H), 7.31 (m, 2H), 7.53 (m, 4H), 7.76 (d, 1H) 1 H-NMR: δ 2.83 (m, 4H), 7.03 (m, 2H), 7.31 (m, 2H), 7.53 (m, 4H), 7.76 (d, 1H)
<단계 2> 4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole의 합성<Step 2> Synthesis of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole
질소 기류 하에서 3.06 g (8.80 mmol)의 4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole, 1.61 g (9.67 mmol)의 2-nitrophenylboronic acid, 1.06 g (26.37 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 필터링하였다. 필터링된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole (2.82 g, 7.22 mmol, 수율 82 %)을 획득하였다. 3.06 g (8.80 mmol) of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole, 1.61 g (9.67 mmol) of 2-nitrophenylboronic acid, 1.06 g (26.37 mmol) under nitrogen stream NaOH and 100 ml / 50 ml of THF / H 2 O were added and 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. Removing the solvent of the filtered organic layer and then using column chromatography 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (2.82 g, 7.22 mmol, yield) 82%) was obtained.
1H-NMR : δ 2.84 (m, 4H), 7.01 (d, 1H), 7.33 (t, 1H), 7.59 (m, 7H), 7.99 (m, 3H) 1 H-NMR: δ 2.84 (m, 4H), 7.01 (d, 1H), 7.33 (t, 1H), 7.59 (m, 7H), 7.99 (m, 3H)
<단계 3> IC-1과 IC-2의 합성Step 3 Synthesis of IC-1 and IC-2
질소 기류 하에서 4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 2.82 g (7.22 mmol)과 triphenylphosphine 4.73 g (18.05 mmol), 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgSO4로 물을 제거하고, 컬럼크로마토그래피를 이용하여 목적 화합물인 IC-1 (0.99 g, 2.75 mmol, 수율 38 %) 과 IC-2 (0.97 g, 2.74 mmol, 수율 37 %)을 각각 획득하였다. 2.82 g (7.22 mmol) of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole with 4.73 g (18.05 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene under nitrogen stream After stirring for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was removed with water using MgSO 4 , and column chromatography was used to form IC-1 (0.99 g, 2.75 mmol, yield 38%) and IC-2 (0.97 g, 2.74 mmol, yield 37%). Were obtained respectively.
IC-1 의 1H-NMR : δ 2.83 (m, 4H), 7.00 (d, 1H), 7.30 (m, 2H), 7.54 (m, 8H), 7.76 (d, 1H), 8.12 (d, 1H), 10.01 (s, 1H) 1 H-NMR of IC-1: δ 2.83 (m, 4H), 7.00 (d, 1H), 7.30 (m, 2H), 7.54 (m, 8H), 7.76 (d, 1H), 8.12 (d, 1H ), 10.01 (s, 1H)
IC-2 의 1H-NMR : δ 2.84 (m, 4H), 7.00 (d, 1H), 7.28 (m, 3H), 7.56 (m, 7H), 7.77 (d, 1H), 8.12 (d, 1H), 10.21 (s, 1H) 1 H-NMR of IC-2: δ 2.84 (m, 4H), 7.00 (d, 1H), 7.28 (m, 3H), 7.56 (m, 7H), 7.77 (d, 1H), 8.12 (d, 1H ), 10.21 (s, 1H)
[준비예 2] IC-3과 IC-4의 합성Preparation Example 2 Synthesis of IC-3 and IC-4
<단계 1> 6-(biphenyl-4-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole의 합성Step 1 Synthesis of 6- (biphenyl-4-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole
1-bromobenzene 대신 4-bromobiphenyl (8.67 g, 37.18 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 6-(biphenyl-4-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.Except for using 4-bromobiphenyl (8.67 g, 37.18 mmol) instead of 1-bromobenzene, 6- (biphenyl-4-yl) -4-bromo was carried out in the same manner as in <Step 1> of Preparation Example 1 -2,6-dihydro-1H-benzo [def] carbazole was obtained.
1H-NMR : δ 2.84 (m, 4H), 7.01 (m, 2H), 7.31 (m, 2H), 7.64 (m, 7H), 7.79 (m, 3H) 1 H-NMR: δ 2.84 (m, 4H), 7.01 (m, 2H), 7.31 (m, 2H), 7.64 (m, 7H), 7.79 (m, 3H)
<단계 2> 6-(biphenyl-4-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole 의 합성<Step 2> Synthesis of 6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H-benzo [def] carbazole
4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 6-(biphenyl-4-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole (3.72 g, 8.80 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 6-(biphenyl-4-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.6- (biphenyl-4-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole (instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole ( 3.72 g, 8.80 mmol) was subjected to the same process as in <Step 2> of Preparation Example 1, except that 6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6 -dihydro-1H-benzo [def] carbazole was obtained.
1H-NMR : δ 2.85 (m, 4H), 7.01 (d, 1H), 7.28 (t, 1H), 7.51 (m, 6H), 7.69 (m, 7H), 7.98 (m, 3H) 1 H-NMR: δ 2.85 (m, 4H), 7.01 (d, 1H), 7.28 (t, 1H), 7.51 (m, 6H), 7.69 (m, 7H), 7.98 (m, 3H)
<단계 3> IC-3과 IC-4의 합성Step 3 Synthesis of IC-3 and IC-4
4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 6-(biphenyl-4-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole (3.27 g, 7.22 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 목적 화합물 IC-3과 IC-4를 각각 얻었다.4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole instead of 6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6-dihydro- Except that 1H-benzo [def] carbazole (3.27 g, 7.22 mmol) was used, the same procedure as in <Step 3> of Preparation Example 1 was performed to obtain target compounds IC-3 and IC-4, respectively.
IC-3 의 1H-NMR : δ 2.83 (m, 4H), 6.91 (d, 1H), 7.28 (m, 2H), 7.49 (m, 7H), 7.66 (m, 6H), 8.11 (d, 1H), 10.07 (s, 1H) 1 H-NMR of IC-3: δ 2.83 (m, 4H), 6.91 (d, 1H), 7.28 (m, 2H), 7.49 (m, 7H), 7.66 (m, 6H), 8.11 (d, 1H ), 10.07 (s, 1 H)
IC-4 의 1H-NMR : δ 2.83 (m, 4H), 6.90 (d, 1H), 7.29 (m, 3H), 7.52 (m, 6H), 7.67 (m, 6H), 8.11 (d, 1H), 10.22 (s, 1H) 1 H-NMR of IC-4: δ 2.83 (m, 4H), 6.90 (d, 1H), 7.29 (m, 3H), 7.52 (m, 6H), 7.67 (m, 6H), 8.11 (d, 1H ), 10.22 (s, 1H)
[준비예 3] IC-5과 IC-6의 합성Preparation Example 3 Synthesis of IC-5 and IC-6
<단계 1> 6-(biphenyl-3-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole의 합성<Step 1> Synthesis of 6- (biphenyl-3-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole
1-bromobenzene 대신 3-bromobiphenyl (8.67 g, 37.18 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 6-(biphenyl-3-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.Except for using 3-bromobiphenyl (8.67 g, 37.18 mmol) instead of 1-bromobenzene, 6- (biphenyl-3-yl) -4-bromo was carried out in the same manner as in <Step 1> of Preparation Example 1 -2,6-dihydro-1H-benzo [def] carbazole was obtained.
1H-NMR : δ 2.84 (m, 4H), 6.97 (m, 2H), 7.28 (m, 2H), 7.48 (m, 8H), 7.76 (d, 1H), 8.01 (s, 1H) 1 H-NMR: δ 2.84 (m, 4H), 6.97 (m, 2H), 7.28 (m, 2H), 7.48 (m, 8H), 7.76 (d, 1H), 8.01 (s, 1H)
<단계 2> 6-(biphenyl-3-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole 의 합성<Step 2> Synthesis of 6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H-benzo [def] carbazole
4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 6-(biphenyl-3-yl)-4-bromo-2,6-dihydro-1H-benzo[def]carbazole(3.73 g, 8.8 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 6-(biphenyl-3-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.6- (biphenyl-3-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole ( 3.73 g, 8.8 mmol) was subjected to the same process as in <Step 2> of Preparation Example 1, except that 6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6 -dihydro-1H-benzo [def] carbazole was obtained.
1H-NMR : δ 2.83 (m, 4H), 6.95 (d, 1H), 7.28 (t, 1H), 7.51 (m, 10H), 7.73 (m, 2H), 8.02 (m, 3H) 1 H-NMR: δ 2.83 (m, 4H), 6.95 (d, 1H), 7.28 (t, 1H), 7.51 (m, 10H), 7.73 (m, 2H), 8.02 (m, 3H)
<단계 3> IC-5과 IC-6의 합성Step 3 Synthesis of IC-5 and IC-6
4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 6-(biphenyl-3-yl)-4-(2-nitrophenyl)-2,6-dihydro-1H-benzo[def]carbazole (3.3 g, 7.22 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 목적화합물 IC-5과 IC-6를 각각 얻었다.6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6-dihydro- instead of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole Except that 1H-benzo [def] carbazole (3.3 g, 7.22 mmol) was used, the same procedure as in <Step 3> of Preparation Example 1 was performed to obtain target compounds IC-5 and IC-6, respectively.
IC-5 의 1H-NMR : δ 2.83 (m, 4H), 6.87 (d, 1H), 7.28 (m, 2H), 7.50 (m, 11H), 7.78 (d, 1H), 8.05 (m, 2H), 10.01 (s, 1H) 1 H-NMR of IC-5: δ 2.83 (m, 4H), 6.87 (d, 1H), 7.28 (m, 2H), 7.50 (m, 11H), 7.78 (d, 1H), 8.05 (m, 2H ), 10.01 (s, 1H)
IC-6 의 1H-NMR : δ 2.83 (m, 4H), 6.87 (d, 1H), 7.27 (m, 3H), 7.51 (m, 10H), 7.78 (d, 1H), 8.04 (m, 2H), 10.12 (s, 1H) 1 H-NMR of IC-6: δ 2.83 (m, 4H), 6.87 (d, 1H), 7.27 (m, 3H), 7.51 (m, 10H), 7.78 (d, 1H), 8.04 (m, 2H ), 10.12 (s, 1H)
[준비예 4] IC-7의 합성Preparation Example 4 Synthesis of IC-7
<단계 1> tert-butyl 4-bromo-1H-benzo[def]carbazole-6(2H)-carboxylate의 합성Step 1 Synthesis of tert-butyl 4-bromo-1H-benzo [def] carbazole-6 (2H) -carboxylate
4-bromo-2,6-dihydro-1H-benzo[def]carbazole (16.33 g, 60.0 mmol), Di-tert-butyldicarbonate (26.0 ml, 113.2 mmol), 4-Dimethylaminopyridine (7.35 g, 60.1 mmol)을 Acetonitrile 300 ml에 녹이고, 상온에서 2시간 교반하였다. 반응이 종료 된 후에 물을 붓고, 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 tert-butyl 4-bromo-1H-benzo[def]carbazole-6(2H)-carboxylate (20.55 g, 55.2 mmol, 수율 92%)을 얻었다.Acetonitrile of 4-bromo-2,6-dihydro-1H-benzo [def] carbazole (16.33 g, 60.0 mmol), Di-tert-butyldicarbonate (26.0 ml, 113.2 mmol), 4-Dimethylaminopyridine (7.35 g, 60.1 mmol) It was dissolved in 300 ml and stirred at room temperature for 2 hours. After the reaction was completed, water was poured, 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 the title compound tert-butyl 4-bromo-1H-benzo [def] carbazole-6 (2H) -carboxylate (20.55 g, 55.2 mmol, 92% yield).
1H-NMR : δ 1.59 (s, 9H), 2.85 (m, 4H), 7.03 (d, 1H), 7.27 (m, 3H), 7.51 (d, 1H) 1 H-NMR: δ 1.59 (s, 9H), 2.85 (m, 4H), 7.03 (d, 1H), 7.27 (m, 3H), 7.51 (d, 1H)
<단계 2> tert-butyl 4-(2-nitrophenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate의 합성Synthesis of tert-butyl 4- (2-nitrophenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate
4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 tert-butyl 4-(2-nitrophenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate (3.28 g, 8.8 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 tert-butyl 4-(2-nitrophenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate을 얻었다.Tert-butyl 4- (2-nitrophenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate (3.28 g) instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole , 8.8 mmol), except that tert-butyl 4- (2-nitrophenyl) -1H-benzo [def] carbazole-6 (2H) was carried out in the same manner as in <Step 2> of Preparation Example 1. -carboxylate was obtained.
1H-NMR : δ 1.59 (s, 9H), 2.85 (m, 4H), 7.28 (m, 2H), 7.51 (m, 3H), 7.71 (d, 1H), 7.99 (m, 3H) 1 H-NMR: δ 1.59 (s, 9H), 2.85 (m, 4H), 7.28 (m, 2H), 7.51 (m, 3H), 7.71 (d, 1H), 7.99 (m, 3H)
<단계 3> IC-7-1과 IC-10-1의 합성Step 3 Synthesis of IC-7-1 and IC-10-1
4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 tert-butyl 4-(2-nitrophenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate (2.99 g, 7.22 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 목적화합물 IC-7-1과 IC-10-1을 얻었다.Tert-butyl 4- (2-nitrophenyl) -1H-benzo [def] carbazole-6 (2H)-instead of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole Except for using carboxylate (2.99 g, 7.22 mmol), the same procedure as in <Step 3> of Preparation Example 1 was carried out to obtain the target compounds IC-7-1 and IC-10-1.
IC-7-1 의 1H-NMR : δ 1.60 (s, 9H), 2.84 (m, 4H), 7.29 (m, 3H), 7.50 (m, 3H), 7.61 (d, 1H), 8.03 (d, 1H), 10.04 (s, 1H) 1 H-NMR of IC-7-1: δ 1.60 (s, 9H), 2.84 (m, 4H), 7.29 (m, 3H), 7.50 (m, 3H), 7.61 (d, 1H), 8.03 (d , 1H), 10.04 (s, 1H)
IC-10-1 의 1H-NMR : δ 1.60 (s, 9H), 2.83 (m, 4H), 7.27 (m, 3H), 7.51 (m, 3H), 7.61 (d, 1H), 8.04 (d, 1H), 10.13 (s, 1H) 1 H-NMR of IC-10-1: δ 1.60 (s, 9H), 2.83 (m, 4H), 7.27 (m, 3H), 7.51 (m, 3H), 7.61 (d, 1H), 8.04 (d , 1H), 10.13 (s, 1H)
<단계 3> IC-7의 합성Step 3 Synthesis of IC-7
질소 기류 하에서 IC-7-1 (4.74 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder(0.15 g, 2.48 mmol), K2CO3(3.42 g, 24.79 mmol), Na2SO4(3.53 g, 24.79 mmol) 및 nitrobenzene(100 ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. IC-7-1 (4.74 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder (0.15 g, 2.48 mmol), K 2 CO 3 (3.42 g, 24.79 mmol), Na under a stream of nitrogen. 2 SO 4 (3.53 g, 24.79 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 h.
반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후, 유기화합물을 Silica-gel (500 g)과 함께 Toluene 2000 ml에 넣고 110℃에서 12시간을 교반하였고, filter로 silica-gel을 제거하고 Toluene을 농축하여 목적화합물 IC-7 (2.80 g, 7.81 mmol, 수율 63%)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, the organic compound was added to 2000 ml of Toluene with Silica-gel (500 g) and stirred at 110 ° C. for 12 hours. The silica-gel was removed with a filter and the toluene was concentrated. (2.80 g, 7.81 mmol, yield 63%) were obtained.
1H-NMR : δ 2.84 (m, 4H), 7.33 (m, 4H), 7.52 (m, 6H), 7.91 (d, 1H), 8.04 (d, 1H), 8.55 (d, 1H), 10.03 (s, 1H) 1 H-NMR: δ 2.84 (m, 4H), 7.33 (m, 4H), 7.52 (m, 6H), 7.91 (d, 1H), 8.04 (d, 1H), 8.55 (d, 1H), 10.03 ( s, 1 H)
[준비예 5] IC-8의 합성Preparation Example 5 Synthesis of IC-8
<단계 1> IC-8의 합성Step 1 Synthesis of IC-8
1-bromobenzene 대신 4-bromobiphenyl (8.67 g, 37.18 mmol)을 사용하는 것을 제외하고는, 상기 준비예 4의 <단계 3>과 동일한 과정을 수행하여 IC-8을 얻었다.Except for using 4-bromobiphenyl (8.67 g, 37.18 mmol) instead of 1-bromobenzene, IC-8 was obtained by the same procedure as in <Step 3> of Preparation Example 4.
1H-NMR : δ 2.85 (m, 4H), 7.35 (m, 4H), 7.48 (m, 6H), 7.69 (m, 4H), 7.96 (m, 2H), 8.53 (d, 1H), 10.04 (s, 1H) 1 H-NMR: δ 2.85 (m, 4H), 7.35 (m, 4H), 7.48 (m, 6H), 7.69 (m, 4H), 7.96 (m, 2H), 8.53 (d, 1H), 10.04 ( s, 1 H)
[준비예 6] IC-9의 합성Preparation Example 6 Synthesis of IC-9
<단계 1> IC-9의 합성Step 1 Synthesis of IC-9
1-bromobenzene 대신 3-bromobiphenyl (8.67 g, 37.18 mmol)을 사용하는 것을 제외하고는, 상기 준비예 4의 <단계 3>과 동일한 과정을 수행하여 IC-9을 얻었다.Except for using 3-bromobiphenyl (8.67 g, 37.18 mmol) instead of 1-bromobenzene, IC-9 was obtained by the same procedure as in <Step 3> of Preparation Example 4.
1H-NMR : δ 2.85 (m, 4H), 7.33 (m, 4H), 7.42 (m, 5H), 7.67 (m, 5H), 7.92 (m, 2H), 8.53 (d, 1H), 10.04 (s, 1H) 1 H-NMR: δ 2.85 (m, 4H), 7.33 (m, 4H), 7.42 (m, 5H), 7.67 (m, 5H), 7.92 (m, 2H), 8.53 (d, 1H), 10.04 ( s, 1 H)
[준비예 7] IC-10의 합성Preparation Example 7 Synthesis of IC-10
<단계 1> IC-10의 합성<Step 1> Synthesis of IC-10
IC-7-1 대신 IC-10-1 (4.74 g, 12.40 mmol)을 사용하는 것을 제외하고는, 상기 준비예 4의 <단계 3>과 동일한 과정을 수행하여 IC-10을 얻었다.Except for using IC-10-1 (4.74 g, 12.40 mmol) instead of IC-7-1, IC-10 was obtained by the same process as <Step 3> of Preparation Example 4.
1H-NMR : δ 2.83 (m, 4H), 7.31 (m, 4H), 7.51 (m, 8H), 7.92 (d, 1H), 10.09 (s, 1H) 1 H-NMR: δ 2.83 (m, 4H), 7.31 (m, 4H), 7.51 (m, 8H), 7.92 (d, 1H), 10.09 (s, 1H)
[준비예 8] IC-11의 합성Preparation Example 8 Synthesis of IC-11
<단계 1> IC-11의 합성Step 1 Synthesis of IC-11
IC-7-1 대신 IC-10-1 (4.74 g, 12.40 mmol)을 사용하는 것을 제외하고는, 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 IC-11을 얻었다.Except for using IC-10-1 (4.74 g, 12.40 mmol) instead of IC-7-1, IC-11 was obtained by the same process as <Step 1> of Preparation Example 5.
1H-NMR : δ 2.84 (m, 4H), 7.32 (m, 4H), 7.51 (m, 7H), 7.76 (m, 5H), 7.99 (d, 1H), 10.08 (s, 1H) 1 H-NMR: δ 2.84 (m, 4H), 7.32 (m, 4H), 7.51 (m, 7H), 7.76 (m, 5H), 7.99 (d, 1H), 10.08 (s, 1H)
[준비예 9] IC-12의 합성Preparation Example 9 Synthesis of IC-12
<단계 1> IC-12의 합성Step 1 Synthesis of IC-12
IC-7-1 대신 IC-10-1 (4.74 g, 12.40 mmol)을 사용하는 것을 제외하고는, 상기 준비예 6의 <단계 1>과 동일한 과정을 수행하여 IC-12를 얻었다.Except for using IC-10-1 (4.74 g, 12.40 mmol) instead of IC-7-1, IC-12 was obtained by the same process as <Step 1> of Preparation Example 6.
1H-NMR : δ 2.84 (m, 4H), 7.35 (m, 4H), 7.54 (m, 6H), 7.79 (m, 6H), 8.01 (d, 1H), 10.11 (s, 1H) 1 H-NMR: δ 2.84 (m, 4H), 7.35 (m, 4H), 7.54 (m, 6H), 7.79 (m, 6H), 8.01 (d, 1H), 10.11 (s, 1H)
[준비예 10] IC-13과 IC-14의 합성Preparation Example 10 Synthesis of IC-13 and IC-14
<단계 1> 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole의 합성<Step 1> Synthesis of 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole
4-bromo-2,6-dihydro-1H-benzo[def]carbazole 대신 4,8-dibromo-2,6-dihydro-1H-benzo[def]carbazole (4.35 g, 12.40 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.4,8-dibromo-2,6-dihydro-1H-benzo [def] carbazole (4.35 g, 12.40 mmol) instead of 4-bromo-2,6-dihydro-1H-benzo [def] carbazole , 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole was obtained in the same manner as in <Step 1> of Preparation Example 1.
1H-NMR : δ 2.84 (m, 4H), 7.03 (s, 2H), 7.39 (s, 2H), 7.49 (m, 5H) 1 H-NMR: δ 2.84 (m, 4H), 7.03 (s, 2H), 7.39 (s, 2H), 7.49 (m, 5H)
<단계 2> 4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole의 합성<Step 2> Synthesis of 4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole
4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole (3.76 g, 8.80 mmol)을 사용하는 것과 2-nitrophenylboronic acid 대신 phenylboronic acid (3.22 g, 26.37 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (3.76 g, 8.80 instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole mmol) and phenylboronic acid (3.22 g, 26.37 mmol) instead of 2-nitrophenylboronic acid, the same process as in <Step 2> of Preparation Example 1 was carried out to 4-bromo-6,8 -diphenyl-2,6-dihydro-1H-benzo [def] carbazole was obtained.
1H-NMR : δ 2.84 (m, 4H), 7.08 (m, 2H), 7.39 (m, 4H), 7.53 (m, 8H) 1 H-NMR: δ 2.84 (m, 4H), 7.08 (m, 2H), 7.39 (m, 4H), 7.53 (m, 8H)
<단계 3> 4-(2-nitrophenyl)-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole 의 합성
<Step 3> 4- (2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole Synthesis of
4-bromo-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole (3.73 g, 8.80 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 4-(2-nitrophenyl)-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole을 얻었다.4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole (3.73 g, 8.80 instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole Except for using mmol), 4- (2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [def] was carried out in the same manner as in <Step 2> of Preparation Example 1 above. ] carbazole was obtained.
1H-NMR : δ 2.89 (m, 4H), 7.41 (m, 4H), 7.53 (m, 11H), 7.94 (m, 3H) 1 H-NMR: δ 2.89 (m, 4H), 7.41 (m, 4H), 7.53 (m, 11H), 7.94 (m, 3H)
<단계 4> IC-13과 IC-14의 합성Step 4 Synthesis of IC-13 and IC-14
4-(2-nitrophenyl)-6-phenyl-2,6-dihydro-1H-benzo[def]carbazole 대신 4-(2-nitrophenyl)-6,8-diphenyl-2,6-dihydro-1H-benzo[def]carbazole (3.37 g, 7.22 mmol)을 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 목적화합물 IC-13과 IC-14를 얻었다.4- (2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [instead of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole Except for using def] carbazole (3.37 g, 7.22 mmol), the target compounds IC-13 and IC-14 were obtained by the same procedure as in <Step 3> of Preparation Example 1.
IC-13 의 1H-NMR : δ 2.87 (m, 4H), 7.42 (m, 6H), 7.54 (m, 10H), 7.94 (s, 1H), 10.04 (s, 1H) 1 H-NMR of IC-13: δ 2.87 (m, 4H), 7.42 (m, 6H), 7.54 (m, 10H), 7.94 (s, 1H), 10.04 (s, 1H)
IC-14 의 1H-NMR : δ 2.87 (m, 4H), 7.43 (m, 5H), 7.57 (m, 9H), 7.89 (s, 1H), 10.12 (s, 1H) 1 H-NMR of IC-14: δ 2.87 (m, 4H), 7.43 (m, 5H), 7.57 (m, 9H), 7.89 (s, 1H), 10.12 (s, 1H)
[준비예 11] IC-15의 합성Preparation Example 11 Synthesis of IC-15
<단계 1> tert-butyl 4-(2-(chloromethyl)phenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate의 합성Step 1 Synthesis of tert-butyl 4- (2- (chloromethyl) phenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate
2-nitrophenylboronic acid 대신 2-(chloromethyl)phenylboronic acid (1.50 g, 8.80 mmol)을 사용하는 것을 제외하고는, 상기 준비예 4의 <단계 2>와 동일한 과정을 수행하여 tert-butyl 4-(2-(chloromethyl)phenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate을 얻었다.Except for using 2- (chloromethyl) phenylboronic acid (1.50 g, 8.80 mmol) instead of 2-nitrophenylboronic acid, tert-butyl 4- (2- (chloromethyl) phenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate was obtained.
1H-NMR : δ 1.59 (s, 9H), 2.84 (m, 4H), 4.53 (s, 2H), 7.18 (m, 2H), 7.42 (m, 2H), 7.55 (m, 2H), 7.74 (m, 3H) 1 H-NMR: δ 1.59 (s, 9H), 2.84 (m, 4H), 4.53 (s, 2H), 7.18 (m, 2H), 7.42 (m, 2H), 7.55 (m, 2H), 7.74 ( m, 3H)
<단계 2> tert-butyl 4,5-dihydrobenzo[def]indeno[2,1-a]carbazole-12(11H)-carboxylate과 tert-butyl 1,2-dihydrobenzo[def]indeno[1,2-b]carbazole-6(12H)-carboxylate의 합성Step 2 tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate and tert-butyl 1,2-dihydrobenzo [def] indeno [1,2-b ] Synthesis of carbazole-6 (12H) -carboxylate
질소 기류 하에서 tert-butyl 4-(2-(chloromethyl)phenyl)-1H-benzo[def]carbazole-6(2H)-carboxylate (8.36 g, 20.00 mmol), Pd(OAc)2 (0.23 g, 1.00 mmol), 2-(di-tert-butylphosphino)biphenyl ligand (JohnPhos, 0.60 g, 2.00 mmol), TEA (5.6 ml, 40.00 mmol) 및 Toluene (100 ml)를 혼합하고 110℃에서 12시간 동안 교반하였다. Tert-butyl 4- (2- (chloromethyl) phenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate (8.36 g, 20.00 mmol), Pd (OAc) 2 (0.23 g, 1.00 mmol) under nitrogen stream ), 2- (di-tert-butylphosphino) biphenyl ligand (JohnPhos, 0.60 g, 2.00 mmol), TEA (5.6 ml, 40.00 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C. for 12 hours.
반응이 종결된 후 Toluene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 tert-butyl 4,5-dihydrobenzo[def]indeno[2,1-a]carbazole-12(11H)-carboxylate (2.06 g, 5.40 mmol, 수율 27%)과 tert-butyl 1,2-dihydrobenzo[def]indeno[1,2-b]carbazole-6(12H)-carboxylate (2.21 g, 5.80 mmol, 수율 29%)을 얻었다.After completion of the reaction, toluene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and then purified by column chromatography, to obtain tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate (2.06 g, 5.40 mmol, yield). 27%) and tert-butyl 1,2-dihydrobenzo [def] indeno [1,2-b] carbazole-6 (12H) -carboxylate (2.21 g, 5.80 mmol, yield 29%).
tert-butyl 4,5-dihydrobenzo[def]indeno[2,1-a]carbazole-12(11H)-carboxylate의 1H-NMR : δ 1.59 (s, 9H), 2.83 (m, 4H), 4.11 (s, 2H), 7.21 (m, 3H), 7.42 (m, 1H), 7.53 (m, 1H), 7.74 (m, 2H), 7.98 (d, 1H) 1 H-NMR of tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate: δ 1.59 (s, 9H), 2.83 (m, 4H), 4.11 ( s, 2H), 7.21 (m, 3H), 7.42 (m, 1H), 7.53 (m, 1H), 7.74 (m, 2H), 7.98 (d, 1H)
tert-butyl 1,2-dihydrobenzo[def]indeno[1,2-b]carbazole-6(12H)-carboxylate의 1H-NMR : δ 1.59 (s, 9H), 2.83 (m, 4H), 4.11 (s, 2H), 7.22 (m, 3H), 7.44 (m, 1H), 7.51 (m, 1H), 7.74 (m, 2H), 7.89 (d, 1H) 1 H-NMR of tert-butyl 1,2-dihydrobenzo [def] indeno [1,2-b] carbazole-6 (12H) -carboxylate: δ 1.59 (s, 9H), 2.83 (m, 4H), 4.11 ( s, 2H), 7.22 (m, 3H), 7.44 (m, 1H), 7.51 (m, 1H), 7.74 (m, 2H), 7.89 (d, 1H)
<단계 3> IC-15의 합성Step 3 Synthesis of IC-15
질소 기류 하에서 tert-butyl 4,5-dihydrobenzo[def]indeno[2,1-a]carbazole-12(11H)-carboxylate (2.06 g, 5.40 mmol)을 THF 50 ml에 녹인 다음 0℃에서 Potassium tert-butoxide (1.81 g, 16.13 mmol) 넣고 10분 동안 교반하였다. 그리고 Iodomethane (2.29 g, 16.13 mmol)을 넣고 상온에서 12시간 동안 교반하였다. Under nitrogen stream, tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate (2.06 g, 5.40 mmol) was dissolved in 50 ml of THF, followed by Potassium tert- at 0 ° C. butoxide (1.81 g, 16.13 mmol) was added and stirred for 10 minutes. Iodomethane (2.29 g, 16.13 mmol) was added thereto, followed by stirring at room temperature for 12 hours.
반응이 종결된 후 THF를 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 유기화합물을 Silica-gel (150 g)과 함께 Toluene 200 ml에 넣고 110℃에서 12시간을 교반하였고, filter로 silica-gel을 제거하고 Toluene을 농축하여 목적 화합물 IC-15 (1.02 g, 3.29 mmol, 수율 61%) 을 얻었다.After the reaction was completed, THF 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, the organic compound was added to Silica-gel (150 g) in 200 ml of Toluene and stirred for 12 hours at 110 ° C. The silica-gel was removed with a filter and the toluene was concentrated to give the target compound IC-15 ( 1.02 g, 3.29 mmol, 61% yield).
1H-NMR : δ 1.57 (s, 6H), 2.83 (m, 4H), 7.23 (m, 3H), 7.55 (m, 2H), 7.75 (m, 2H), 7.91 (d, 1H), 10.13 (s, 1H) 1 H-NMR: δ 1.57 (s, 6H), 2.83 (m, 4H), 7.23 (m, 3H), 7.55 (m, 2H), 7.75 (m, 2H), 7.91 (d, 1H), 10.13 ( s, 1 H)
[준비예 12] IC-16의 합성Preparation Example 12 Synthesis of IC-16
<단계 1> IC-16의 합성Step 1 Synthesis of IC-16
tert-butyl 4,5-dihydrobenzo[def]indeno[2,1-a]carbazole-12(11H)-carboxylate 대신 tert-butyl 1,2-dihydrobenzo[def]indeno[1,2-b]carbazole-6(12H)-carboxylate (2.06 g, 5.40 mmol)을 사용하는 것을 제외하고는 준비예 11의 <단계 3>과 동일한 과정을 수행하여 목적화합물 IC-16 (1.08 g, 3.51 mmol, 수율 65%)을 얻었다.tert-butyl 1,2-dihydrobenzo [def] indeno [1,2-b] carbazole-6 instead of tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate Except for using (12H) -carboxylate (2.06 g, 5.40 mmol) in the same manner as in <Step 3> of Preparation Example 11 to give the target compound IC-16 (1.08 g, 3.51 mmol, 65% yield) Got it.
1H-NMR : δ 1.57 (s, 6H), 2.83 (m, 4H), 7.24 (m, 3H), 7.51 (m, 2H), 7.72 (m, 2H), 7.93 (d, 1H), 10.08 (s, 1H) 1 H-NMR: δ 1.57 (s, 6H), 2.83 (m, 4H), 7.24 (m, 3H), 7.51 (m, 2H), 7.72 (m, 2H), 7.93 (d, 1H), 10.08 ( s, 1 H)
[합성예 1] Inv-1의 합성Synthesis Example 1 Synthesis of Inv-1
질소 기류 하에서 준비예 1에서 제조된 화합물인 IC-1 (1.07 g, 3.00 mmol), 2-bromo-6-phenylpyridine (0.84 g, 3.60 mmol), Cu powder(0.027 g, 0.40 mmol), K2CO3(0.55 g, 0.40 mmol), Na2SO4(0.57 g, 4.00 mmol) 및 nitrobenzene(100 ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. IC-1 (1.07 g, 3.00 mmol), 2-bromo-6-phenylpyridine (0.84 g, 3.60 mmol), Cu powder (0.027 g, 0.40 mmol), K 2 CO, which was a compound prepared in Preparation Example 1, under nitrogen stream. 3 (0.55 g, 0.40 mmol), Na 2 SO 4 (0.57 g, 4.00 mmol) and nitrobenzene (100 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 컬럼 크로마토그래피(Hexane:EA = 3:1 (v/v))로 정제하여 목적 화합물인 Inv-1 (1.23 g, 수율 80 %)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 (Hexane: EA = 3: 1 (v / v)) to give the title compound Inv-1 (1.23 g, yield 80%).
GC-Mass (이론치: 511.61 g/mol, 측정치: 511 g/mol)GC-Mass (Theoretical value: 511.61 g / mol, Measured value: 511 g / mol)
[합성예 2] Inv-2의 합성Synthesis Example 2 Synthesis of Inv-2
질소 기류 하에서 준비예 1에서 제조된 화합물인 IC-1 (1.07 g, 3.00 mmol)을 DMF 100 ml에 녹이고 여기에 NaH (0.11 g, 4.50 mmol)를 넣고 1시간 교반하였다. 여기에 DMF 100ml에 녹인 2-chloro-4,6-diphenyl-1,3,5-triazine (0.96 g, 3.60 mmol)을 천천히 첨가하였다. 3시간 동안 교반한 후 반응을 종료시키고 혼합물을 실리카 필터링하고 물과 메탄올로 씻은 후 용매를 제거하였다. 용매가 제거된 고체를 컬럼 크로마토그래피 (Hexane:EA = 1:1 (v/v))로 정제하여 목적 화합물인 Inv-2 (1.38 g, 수율 78 %)을 얻었다.Under nitrogen stream, IC-1 (1.07 g, 3.00 mmol), a compound prepared in Preparation Example 1, was dissolved in 100 ml of DMF, and NaH (0.11 g, 4.50 mmol) was added thereto and stirred for 1 hour. To this was slowly added 2-chloro-4,6-diphenyl-1,3,5-triazine (0.96 g, 3.60 mmol) dissolved in 100 ml of DMF. After stirring for 3 hours, the reaction was terminated, the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed. The solvent-free solid was purified by column chromatography (Hexane: EA = 1: 1 (v / v)) to obtain Inv-2 (1.38 g, yield 78%) as a target compound.
GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)
[합성예 3] Inv-3의 합성Synthesis Example 3 Synthesis of Inv-3
2-bromo-6-phenylpyridine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-3 (1.50 g, 수율 75 %)를 얻었다. Inv, which was synthesized in the same manner as in Synthesis Example 1, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6-phenylpyridine -3 (1.50 g, yield 75%) was obtained.
GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)
[합성예 4] Inv-4의 합성Synthesis Example 4 Synthesis of Inv-4
2-bromo-6-phenylpyridine 대신 2-(4-bromophenyl)triphenylene를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-4 (1.65 g, 수율 78 %)를 얻었다. Except for using 2- (4-bromophenyl) triphenylene instead of 2-bromo-6-phenylpyridine, it was synthesized in the same manner as in Synthesis Example 1 to obtain the target compound Inv-4 (1.65 g, yield 78%).
GC-Mass (이론치: 660.26 g/mol, 측정치: 660 g/mol)GC-Mass (Theoretical value: 660.26 g / mol, Measured value: 660 g / mol)
[합성예 5] Inv-5의 합성Synthesis Example 5 Synthesis of Inv-5
2-bromo-6-phenylpyridine 대신 3-bromo-9-phenyl-9H-carbazole를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-5 (1.37 g, 수율 76 %)를 얻었다. Inv-5 (1.37 g, 76% yield), which was synthesized in the same manner as in Synthesis Example 1, except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-6-phenylpyridine. Got.
GC-Mass (이론치: 599.24 g/mol, 측정치: 599 g/mol)GC-Mass (Theoretical value: 599.24 g / mol, Measured value: 599 g / mol)
[합성예 6] Inv-6의 합성Synthesis Example 6 Synthesis of Inv-6
2-bromo-6-phenylpyridine 대신 4-bromodibenzo[b,d]thiophene를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-6 (1.22 g, 수율 75 %)를 얻었다. Synthesis was performed in the same manner as in Synthesis Example 1, except that 4-bromodibenzo [b, d] thiophene was used instead of 2-bromo-6-phenylpyridine to obtain Inv-6 (1.22 g, yield 75%) as a target compound. .
GC-Mass (이론치: 540.17 g/mol, 측정치: 540 g/mol)GC-Mass (Theoretical value: 540.17 g / mol, Measured value: 540 g / mol)
[합성예 7] Inv-7의 합성Synthesis Example 7 Synthesis of Inv-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenylpyrimidine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-7 (1.53 g, 수율 78 %)을 얻었다. Except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, the compound was synthesized in the same manner as in Synthesis Example 1 Phosphorus Inv-7 (1.53 g, yield 78%) was obtained.
GC-Mass (이론치: 664.28 g/mol, 측정치: 664 g/mol)GC-Mass (Theoretical value: 664.28 g / mol, Measured value: 664 g / mol)
[합성예 8] Inv-8의 합성Synthesis Example 8 Synthesis of Inv-8
IC-1 과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 IC-2와 2-chloro-4,6-diphenylpyrimidine를 각각 사용한 것을 제외하고는, 상기 합성예 2와 동일한 방법으로 합성하여 목적 화합물인 Inv-8 (1.25 g, 수율 71 %)를 얻었다. The same method as Synthesis Example 2, except that IC-2 and 2-chloro-4,6-diphenylpyrimidine were used instead of IC-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, respectively. It synthesize | combined and obtained Inv-8 (1.25 g, yield 71%) which is a target compound.
GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)
[합성예 9] Inv-9의 합성Synthesis Example 9 Synthesis of Inv-9
IC-1과 2-bromo-6-phenylpyridine 대신 IC-2와 2-bromo-4,6-diphenylpyridine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-9 (1.41 g, 수율 80 %)를 얻었다. Inv-9 (1.41), which was synthesized in the same manner as in Synthesis Example 1, except that IC-2 and 2-bromo-4,6-diphenylpyridine were used instead of IC-1 and 2-bromo-6-phenylpyridine. g, yield 80%) was obtained.
GC-Mass (이론치: 587.24 g/mol, 측정치: 587 g/mol)GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)
[합성예 10] Inv-10의 합성Synthesis Example 10 Synthesis of Inv-10
IC-1 대신 IC-2를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-10 (1.50 g, 수율 75 %)를 얻었다. Except for using IC-2 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-10 (1.50 g, yield 75%) as a target compound.
GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)
[합성예 11] Inv-11의 합성Synthesis Example 11 Synthesis of Inv-11
IC-1과 2-bromo-6-phenylpyridine 대신 IC-2와 2-(3-bromo-5-methylphenyl)-4,6-diphenyl-1,3,5-triazine 를 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-11 (1.61 g, 수율 79 %)를 얻었다. Except for the use of IC-2 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was carried out in the same manner as in Synthesis example 1 to obtain Inv-11 (1.61 g, 79%) as a target compound.
GC-Mass (이론치: 679.27 g/mol, 측정치: 679 g/mol)GC-Mass (Theoretical value: 679.27 g / mol, Measured value: 679 g / mol)
[합성예 12] Inv-12의 합성Synthesis Example 12 Synthesis of Inv-12
IC-1과 2-bromo-6-phenylpyridine 대신 IC-2와 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,6-diphenyl-1,3,5-triazine를 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-12 (1.58 g, 수율 72 %)를 얻었다. Except for using IC-2 and 2- (3-bromo-5- (trifluoromethyl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-12 (1.58 g, yield 72%) as a target compound.
GC-Mass (이론치: 733.25 g/mol, 측정치: 733 g/mol)GC-Mass (Theoretical value: 733.25 g / mol, Measured value: 733 g / mol)
[합성예 13] Inv-13의 합성Synthesis Example 13 Synthesis of Inv-13
IC-1 대신 IC-3을 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-13 (1.32 g, 수율 75 %)을 얻었다. Except for using IC-3 instead of IC-1, and synthesized in the same manner as in Synthesis Example 1 to obtain the title compound Inv-13 (1.32 g, yield 75%).
GC-Mass (이론치: 587.24 g/mol, 측정치: 587 g/mol)GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)
[합성예 14] Inv-14의 합성Synthesis Example 14 Synthesis of Inv-14
IC-1 대신 IC-3을 사용한 것을 제외하고는, 상기 합성예 2와 동일한 방법으로 합성하여 목적 화합물인 Inv-14 (1.50 g, 수율 75 %)를 얻었다. Except for using IC-3 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 2 to obtain Inv-14 (1.50 g, yield 75%) as a target compound.
GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)
[합성예 15] Inv-15의 합성Synthesis Example 15 Synthesis of Inv-15
IC-1 대신 IC-3을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-15 (1.69 g, 수율 76 %)를 얻었다. Except for using IC-3 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-15 (1.69 g, yield 76%) as a target compound.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 16] Inv-16의 합성Synthesis Example 16 Synthesis of Inv-16
IC-1 대신 IC-3을 사용한 것을 제외하고는, 상기 합성예 7과 동일한 방법으로 합성하여 목적 화합물인 Inv-16 (1.57 g, 수율 71 %)를 얻었다. Except for using IC-3 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 7 to obtain Inv-16 (1.57 g, 71% yield) as a target compound.
GC-Mass (이론치: 740.29 g/mol, 측정치: 740 g/mol)GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)
[합성예 17] Inv-17의 합성Synthesis Example 17 Synthesis of Inv-17
IC-1 대신 IC-4를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-17 (1.45 g, 수율 75 %)를 얻었다. Except for using IC-4 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-17 (1.45 g, yield 75%).
GC-Mass (이론치: 643.27 g/mol, 측정치: 643 g/mol)GC-Mass (Theoretical value: 643.27 g / mol, Measured value: 643 g / mol)
[합성예 18] Inv-18의 합성Synthesis Example 18 Synthesis of Inv-18
IC-2 대신 IC-4를 사용한 것을 제외하고는, 상기 합성예 11과 동일한 방법으로 합성하여 목적 화합물인 Inv-18 (1.65 g, 수율 73 %)를 얻었다. Except for using IC-4 instead of IC-2, the synthesis was carried out in the same manner as in Synthesis Example 11 to obtain Inv-18 (1.65 g, yield 73%) as a target compound.
GC-Mass (이론치: 755.30 g/mol, 측정치: 755 g/mol)GC-Mass (Theoretical value: 755.30 g / mol, Measured value: 755 g / mol)
[합성예 19] Inv-19의 합성Synthesis Example 19 Synthesis of Inv-19
IC-1과 2-bromo-6-phenylpyridine 대신 IC-4와 2-(5-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-19 (1.84 g, 수율 75 %)를 얻었다. Except for using IC-4 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was performed in the same manner as in Synthesis example 1 to obtain Inv-19 (1.84 g, yield 75%) as a target compound.
GC-Mass (이론치: 817.32 g/mol, 측정치: 817 g/mol)GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)
[합성예 20] Inv-20의 합성Synthesis Example 20 Synthesis of Inv-20
IC-1 대신 IC-5를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-20 (1.37 g, 수율 78 %)를 얻었다. Except for using IC-5 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain Inv-20 (1.37 g, yield 78%) as a target compound.
GC-Mass (이론치: 587.24 g/mol, 측정치: 587 g/mol)GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)
[합성예 21] Inv-21의 합성Synthesis Example 21 Synthesis of Inv-21
IC-1 대신 IC-5를 사용한 것을 제외하고는, 상기 합성예 2와 동일한 방법으로 합성하여 목적 화합물인 Inv-21 (1.50 g, 수율 75 %)를 얻었다. Except for using IC-5 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 2 to obtain Inv-21 (1.50 g, yield 75%) as a target compound.
GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)
[합성예 22] Inv-22의 합성Synthesis Example 22 Synthesis of Inv-22
IC-1 대신 IC-5를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-22 (1.78 g, 수율 80 %)를 얻었다. Except for using IC-5 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-22 (1.78 g, yield 80%) as a target compound.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 23] Inv-23의 합성Synthesis Example 23 Synthesis of Inv-23
IC-1 대신 IC-5를 사용한 것을 제외하고는, 상기 합성예 7과 동일한 방법으로 합성하여 목적 화합물인 Inv-23 (1.64 g, 수율 74 %)를 얻었다. Except for using IC-5 instead of IC-1, and synthesized in the same manner as in Synthesis Example 7 to obtain the title compound Inv-23 (1.64 g, 74% yield).
GC-Mass (이론치: 740.29 g/mol, 측정치: 740 g/mol)GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)
[합성예 24] Inv-24의 합성Synthesis Example 24 Synthesis of Inv-24
IC-1 대신 IC-6을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-24 (1.50 g, 수율 78 %)를 얻었다. Except for using IC-6 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-24 (1.50 g, yield 78%) as a target compound.
GC-Mass (이론치: 643.27 g/mol, 측정치: 643 g/mol)GC-Mass (Theoretical value: 643.27 g / mol, Measured value: 643 g / mol)
[합성예 25] Inv-25의 합성Synthesis Example 25 Synthesis of Inv-25
IC-2 대신 IC-6을 사용한 것을 제외하고는, 상기 합성예 11과 동일한 방법으로 합성하여 목적 화합물인 Inv-25 (1.65 g, 수율 73 %)를 얻었다. Except for using IC-6 instead of IC-2, the synthesis was carried out in the same manner as in Synthesis Example 11 to obtain Inv-25 (1.65 g, yield 73%) as a target compound.
GC-Mass (이론치: 755.30 g/mol, 측정치: 755 g/mol)GC-Mass (Theoretical value: 755.30 g / mol, Measured value: 755 g / mol)
[합성예 26] Inv-26의 합성Synthesis Example 26 Synthesis of Inv-26
IC-1과 2-bromo-6-phenylpyridine 대신 IC-6과 2-(5-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-26 (1.74 g, 수율 71 %)를 얻었다. Except for the use of IC-6 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was carried out in the same manner as in Synthesis example 1 to obtain Inv-26 (1.74 g, 71% yield) as a target compound.
GC-Mass (이론치: 817.32 g/mol, 측정치: 817 g/mol)GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)
[합성예 27] Inv-27의 합성Synthesis Example 27 Synthesis of Inv-27
IC-1과 2-bromo-6-phenylpyridine 대신 IC-7과 3-bromo-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole 을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-27 (1.65 g, 수율 73 %)를 얻었다. Except for using IC-7 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole instead of IC-1 and 2-bromo-6-phenylpyridine, respectively Then, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain Inv-27 (1.65 g, yield 73%) as a target compound.
GC-Mass (이론치: 754.28 g/mol, 측정치: 754 g/mol)GC-Mass (Theoretical value: 754.28 g / mol, Measured value: 754 g / mol)
[합성예 28] Inv-28의 합성Synthesis Example 28 Synthesis of Inv-28
IC-1과 2-bromo-6-phenylpyridine 대신 IC-7과 (4-bromophenyl)diphenylborane 을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-28 (1.43 g, 수율 80 %)를 얻었다. Synthesis was performed in the same manner as in Synthesis Example 1, except that IC-7 and (4-bromophenyl) diphenylborane were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Yield 80%).
GC-Mass (이론치: 598.26 g/mol, 측정치: 598 g/mol)GC-Mass (Theoretical value: 598.26 g / mol, Measured value: 598 g / mol)
[합성예 29] Inv-29의 합성Synthesis Example 29 Synthesis of Inv-29
IC-1과 2-bromo-6-phenylpyridine 대신 IC-7과 (4-bromophenyl)diphenylphosphine 을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-29 (1.41 g, 수율 76 %)를 얻었다. Synthesis was carried out in the same manner as in Synthesis Example 1, except that IC-7 and (4-bromophenyl) diphenylphosphine were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Yield 76%).
GC-Mass (이론치: 618.22 g/mol, 측정치: 618 g/mol)GC-Mass (Theoretical value: 618.22 g / mol, Measured value: 618 g / mol)
[합성예 30] Inv-30의 합성Synthesis Example 30 Synthesis of Inv-30
IC-1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 IC-7과 (4-chlorophenyl)triphenylsilane 을 사용한 것을 제외하고는, 상기 합성예 2와 동일한 방법으로 합성하여 목적 화합물인 Inv-30 (1.56 g, 수율 75 %)를 얻었다. Synthesis was carried out in the same manner as in Synthesis Example 2, except that IC-7 and (4-chlorophenyl) triphenylsilane were used instead of IC-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The compound Inv-30 (1.56 g, yield 75%) was obtained.
GC-Mass (이론치: 692.26 g/mol, 측정치: 692 g/mol)GC-Mass (Theoretical value: 692.26 g / mol, Measured value: 692 g / mol)
[합성예 31] Inv-31의 합성Synthesis Example 31 Synthesis of Inv-31
IC-1 대신 IC-7를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-31 (1.50 g, 수율 75 %)를 얻었다. Except for using IC-7 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-31 (1.50 g, yield 75%).
GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)
[합성예 32] Inv-32의 합성Synthesis Example 32 Synthesis of Inv-32
IC-1 대신 IC-10을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-32 (1.51 g, 수율 76 %)를 얻었다. Except for using IC-10 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-32 (1.51 g, 76% yield).
GC-Mass (이론치: 665.28 g/mol, 측정치: 665 g/mol)GC-Mass (Theoretical value: 665.28 g / mol, Measured value: 665 g / mol)
[합성예 33] Inv-33의 합성Synthesis Example 33 Synthesis of Inv-33
IC-1과 2-bromo-6-phenylpyridine 대신 IC-10과 2-(3-bromo-5-methylphenyl)-4,6-diphenyl-1,3,5-triazine 를 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-33 (1.63 g, 수율 80 %)를 얻었다. Except for the use of IC-10 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was carried out in the same manner as in Synthesis example 1 to obtain Inv-33 (1.63 g, yield 80%) as a target compound.
GC-Mass (이론치: 679.27 g/mol, 측정치: 679 g/mol)GC-Mass (Theoretical value: 679.27 g / mol, Measured value: 679 g / mol)
[합성예 34] Inv-34의 합성Synthesis Example 34 Synthesis of Inv-34
IC-1과 2-bromo-6-phenylpyridine 대신 IC-10과 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,6-diphenyl-1,3,5-triazine를 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-12 (1.65 g, 수율 75 %)를 얻었다. Except for using IC-10 and 2- (3-bromo-5- (trifluoromethyl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-12 (1.65 g, yield 75%) as a target compound.
GC-Mass (이론치: 733.25 g/mol, 측정치: 733 g/mol)GC-Mass (Theoretical value: 733.25 g / mol, Measured value: 733 g / mol)
[합성예 35] Inv-35의 합성Synthesis Example 35 Synthesis of Inv-35
IC-1 대신 IC-11을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-35 (1.78 g, 수율 80 %)를 얻었다. Except for using IC-11 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-35 (1.78 g, yield 80%).
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 36] Inv-36의 합성Synthesis Example 36 Synthesis of Inv-36
IC-1 대신 IC-11을 사용한 것을 제외하고는, 상기 합성예 7과 동일한 방법으로 합성하여 목적 화합물인 Inv-16 (1.573g, 수율 78 %)를 얻었다. Except for using IC-11 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 7 to obtain Inv-16 (1.573 g, yield 78%) as a target compound.
GC-Mass (이론치: 740.29 g/mol, 측정치: 740 g/mol)GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)
[합성예 37] Inv-37의 합성Synthesis Example 37 Synthesis of Inv-37
IC-1 대신 IC-8을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-37 (1.67 g, 수율 75 %)를 얻었다. Except for using IC-8 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-37 (1.67 g, yield 75%).
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 38] Inv-38의 합성Synthesis Example 38 Synthesis of Inv-38
IC-1과 2-bromo-6-phenylpyridine 대신 IC-8과 2-(3-bromo-5-methylphenyl)-4,6-diphenyl-1,3,5-triazine를 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-38 (1.61 g, 수율 71 %)를 얻었다. Except for using IC-8 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was performed in the same manner as in Synthesis example 1 to obtain Inv-38 (1.61 g, 71% yield) as a target compound.
GC-Mass (이론치: 755.30 g/mol, 측정치: 755 g/mol)GC-Mass (Theoretical value: 755.30 g / mol, Measured value: 755 g / mol)
[합성예 39] Inv-39의 합성Synthesis Example 39 Synthesis of Inv-39
IC-1과 2-bromo-6-phenylpyridine 대신 IC-4와 2-(5-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine을 각각 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-39 (1.84 g, 수율 75 %)를 얻었다. Except for using IC-4 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 2-bromo-6-phenylpyridine, respectively, Synthesis was performed in the same manner as in Synthesis example 1 to obtain Inv-39 (1.84 g, yield 75%) as a target compound.
GC-Mass (이론치: 817.32 g/mol, 측정치: 817 g/mol)GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)
[합성예 40] Inv-40의 합성Synthesis Example 40 Synthesis of Inv-40
IC-1 대신 IC-9을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-40 (1.67 g, 수율 75 %)를 얻었다. Except for using IC-9 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-40 (1.67 g, yield 75%) as a target compound.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 41] Inv-41의 합성Synthesis Example 41 Synthesis of Inv-41
IC-1 대신 IC-9를 사용한 것을 제외하고는, 상기 합성예 7과 동일한 방법으로 합성하여 목적 화합물인 Inv-41 (1.64 g, 수율 74 %)를 얻었다. Except for using IC-9 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 7 to obtain Inv-41 (1.64 g, 74% yield) as a target compound.
GC-Mass (이론치: 740.29 g/mol, 측정치: 740 g/mol)GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)
[합성예 42] Inv-42의 합성Synthesis Example 42 Synthesis of Inv-42
IC-1 대신 IC-12를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-42 (1.78 g, 수율 80 %)를 얻었다. Except for using IC-12 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-42 (1.78 g, yield 80%).
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 43] Inv-43의 합성Synthesis Example 43 Synthesis of Inv-43
IC-1 대신 IC-13을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-43 (1.58 g, 수율 71 %)를 얻었다. Except for using IC-13 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-43 (1.58 g, 71% yield).
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 44] Inv-44의 합성Synthesis Example 44 Synthesis of Inv-44
IC-1 대신 IC-14을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-44 (1.76 g, 수율 79 %)를 얻었다. Except for using IC-14 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-44 (1.76 g, yield 79%).
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 45] Inv-45의 합성Synthesis Example 45 Synthesis of Inv-45
IC-1 대신 IC-15을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-45 (1.48 g, 수율 80 %)를 얻었다. Except for using IC-15 instead of IC-1, the synthesis was carried out in the same manner as in Synthesis Example 3 to obtain Inv-45 (1.48 g, yield 80%) as a target compound.
GC-Mass (이론치: 616.26 g/mol, 측정치: 616 g/mol)GC-Mass (Theoretical value: 616.26 g / mol, Measured value: 616 g / mol)
[합성예 46] Inv-46의 합성Synthesis Example 46 Synthesis of Inv-46
IC-1 대신 IC-16을 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 합성하여 목적 화합물인 Inv-46 (1.42 g, 수율 77 %)를 얻었다. Except for using IC-16 instead of IC-1, and synthesized in the same manner as in Synthesis Example 3 to obtain the title compound Inv-46 (1.42 g, yield 77%).
GC-Mass (이론치: 616.26 g/mol, 측정치: 616 g/mol)GC-Mass (Theoretical value: 616.26 g / mol, Measured value: 616 g / mol)
[합성예 47] Inv-47의 합성Synthesis Example 47 Synthesis of Inv-47
2-bromo-6-phenylpyridine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-47 (1.58 g, 수율 71 %)를 얻었다. Inv, which was synthesized in the same manner as in Synthesis Example 1, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6-phenylpyridine -47 (1.58 g, yield 71%) was obtained.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 48] Inv-48의 합성Synthesis Example 48 Synthesis of Inv-48
2-bromo-6-phenylpyridine 대신 2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-48 (1.56 g, 수율 70%)를 얻었다. Synthesis was performed in the same manner as in Synthesis Example 1, except that 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6-phenylpyridine. Inv-48 (1.56 g, yield 70%) was obtained.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 49] Inv-49의 합성Synthesis Example 49 Synthesis of Inv-49
2-bromo-6-phenylpyridine 대신 2-(3'-bromobiphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-49 (1.56 g, 수율 70%)를 얻었다. Synthesis in the same manner as in Synthesis Example 1, except that 2- (3'-bromobiphenyl-4-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6-phenylpyridine Inv-49 (1.56 g, yield 70%) was obtained.
GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)
[합성예 50] Inv-50의 합성Synthesis Example 50 Synthesis of Inv-50
2-bromo-6-phenylpyridine 대신 N-(biphenyl-4-yl)-N-(4-bromophenyl)biphenyl-4-amine를 사용한 것을 제외하고는, 상기 합성예 1과 동일한 방법으로 합성하여 목적 화합물인 Inv-50 (1.69 g, 수율 75%)를 얻었다. Except for using N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine instead of 2-bromo-6-phenylpyridine, the compound was synthesized in the same manner as in Synthesis Example 1 Inv-50 (1.69 g, yield 75%) was obtained.
GC-Mass (이론치: 753.31 g/mol, 측정치: 753 g/mol)GC-Mass (Theoretical value: 753.31 g / mol, Measured value: 753 g / mol)
[실시예 1] 유기 EL 소자의 제작Example 1 Fabrication of Organic EL Device
합성예 1에서 합성된 화합물 Inv-1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 EL 소자를 제조하였다.The compound Inv-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, 합성예 1의 화합물 Mat-1를 호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 화합물 Inv-1 + 10 % Ir(ppy)3(300nm) / BCP(10 nm) / Alq3(30 nm) / LiF(1 nm) / Al(200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다.On the prepared ITO transparent electrode, using the compound Mat-1 of Synthesis Example 1 as a host, m-MTDATA (60 nm) / TCTA (80 nm) / compound Inv-1 + 10% Ir (ppy) 3 ( An organic EL device was fabricated by laminating in order of 300 nm) / BCP (10 nm) / Alq 3 (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.
[실시예 2 ~ 50] 유기 EL 소자의 제조[Examples 2 to 50] Fabrication of Organic EL Device
실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Inv-1 대신 합성예 2 내지 50에서 각각 합성된 화합물 (Inv-2 ~ Inv-50)을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 유기 EL 소자를 제조하였다.Example 1, except that the compound (Inv-2 ~ Inv-50) synthesized in Synthesis Examples 2 to 50 instead of the compound Inv-1 used as the light emitting host material when forming the light emitting layer in Example 1, The organic EL device was fabricated as described above.
[비교예 1] 유기 EL 소자의 제작Comparative Example 1 Fabrication of Organic EL Device
발광층 형성시 발광 호스트 물질로서 사용된 화합물 Inv-1 대신 CBP를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 EL 소자를 제작하였다. CBP의 구조는 하기와 같다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Inv-1 used as the light emitting host material when forming the emission layer. The structure of CBP is as follows.
[실험예]Experimental Example
실시예 1 내지 50, 및 비교예 1 에서 각각 제조된 녹색 유기 EL 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For green organic EL devices prepared in Examples 1 to 50 and Comparative Example 1, 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) | 전류효율(cd/A) |
| 실시예 1 | Inv-1 | 6.55 | 41.5 |
| 실시예 2 | Inv-2 | 6.49 | 41.0 |
| 실시예 3 | Inv-3 | 6.53 | 41.3 |
| 실시예 4 | Inv-4 | 6.55 | 40.9 |
| 실시예 5 | Inv-5 | 6.50 | 41.0 |
| 실시예 6 | Inv-6 | 6.52 | 41.2 |
| 실시예 7 | Inv-7 | 6.51 | 41.5 |
| 실시예 8 | Inv-8 | 6.44 | 40.8 |
| 실시예 9 | Inv-9 | 6.50 | 41.6 |
| 실시예 10 | Inv-10 | 6.45 | 41.3 |
| 실시예 11 | Inv-11 | 6.58 | 40.8 |
| 실시예 12 | Inv-12 | 6.60 | 41.0 |
| 실시예 13 | Inv-13 | 6.55 | 41.2 |
| 실시예 14 | Inv-14 | 6.50 | 41.7 |
| 실시예 15 | Inv-15 | 6.65 | 42.1 |
| 실시예 16 | Inv-16 | 6.60 | 41.5 |
| 실시예 17 | Inv-17 | 6.62 | 41.9 |
| 실시예 18 | Inv-18 | 6.50 | 41.7 |
| 실시예 19 | Inv-19 | 6.45 | 40.5 |
| 실시예 20 | Inv-20 | 6.52 | 41.5 |
| 실시예 21 | Inv-21 | 6.50 | 40.9 |
| 실시예 22 | Inv-22 | 6.60 | 41.5 |
| 실시예 23 | Inv-23 | 6.45 | 41.8 |
| 실시예 24 | Inv-24 | 6.52 | 40.8 |
| 실시예 25 | Inv-25 | 6.55 | 41.2 |
| 실시예 26 | Inv-26 | 6.58 | 41.5 |
| 실시예 27 | Inv-27 | 6.61 | 42.1 |
| 실시예 28 | Inv-28 | 6.50 | 41.6 |
| 실시예 29 | Inv-29 | 6.55 | 41.0 |
| 실시예 30 | Inv-30 | 6.50 | 41.3 |
| 실시예 31 | Inv-31 | 6.60 | 40.8 |
| 실시예 32 | Inv-32 | 6.55 | 41.5 |
| 실시예 33 | Inv-33 | 6.55 | 41.2 |
| 실시예 34 | Inv-34 | 6.50 | 41.7 |
| 실시예 35 | Inv-35 | 6.65 | 42.1 |
| 실시예 36 | Inv-36 | 6.60 | 41.3 |
| 실시예 37 | Inv-37 | 6.62 | 40.9 |
| 실시예 38 | Inv-38 | 6.50 | 41.2 |
| 실시예 39 | Inv-39 | 6.45 | 40.6 |
| 실시예 40 | Inv-40 | 6.52 | 41.0 |
| 실시예 41 | Inv-41 | 6.50 | 40.7 |
| 실시예 42 | Inv-42 | 6.60 | 41.1 |
| 실시예 43 | Inv-43 | 6.45 | 41.0 |
| 실시예 44 | Inv-44 | 6.52 | 40.5 |
| 실시예 45 | Inv-45 | 6.55 | 40.9 |
| 실시예 46 | Inv-46 | 6.50 | 42.0 |
| 실시예 47 | Inv-47 | 6.51 | 41.9 |
| 실시예 48 | Inv-48 | 6.50 | 41.8 |
| 실시예 49 | Inv-49 | 6.45 | 42.1 |
| 실시예 50 | Inv-50 | 6.45 | 41.5 |
| 비교예 1 | CBP | 6.93 | 38.2 |
| Sample | Host | Drive voltage (V) | Current efficiency (cd / A) |
| Example 1 | Inv-1 | 6.55 | 41.5 |
| Example 2 | Inv-2 | 6.49 | 41.0 |
| Example 3 | Inv-3 | 6.53 | 41.3 |
| Example 4 | Inv-4 | 6.55 | 40.9 |
| Example 5 | Inv-5 | 6.50 | 41.0 |
| Example 6 | Inv-6 | 6.52 | 41.2 |
| Example 7 | Inv-7 | 6.51 | 41.5 |
| Example 8 | Inv-8 | 6.44 | 40.8 |
| Example 9 | Inv-9 | 6.50 | 41.6 |
| Example 10 | Inv-10 | 6.45 | 41.3 |
| Example 11 | Inv-11 | 6.58 | 40.8 |
| Example 12 | Inv-12 | 6.60 | 41.0 |
| Example 13 | Inv-13 | 6.55 | 41.2 |
| Example 14 | Inv-14 | 6.50 | 41.7 |
| Example 15 | Inv-15 | 6.65 | 42.1 |
| Example 16 | Inv-16 | 6.60 | 41.5 |
| Example 17 | Inv-17 | 6.62 | 41.9 |
| Example 18 | Inv-18 | 6.50 | 41.7 |
| Example 19 | Inv-19 | 6.45 | 40.5 |
| Example 20 | Inv-20 | 6.52 | 41.5 |
| Example 21 | Inv-21 | 6.50 | 40.9 |
| Example 22 | Inv-22 | 6.60 | 41.5 |
| Example 23 | Inv-23 | 6.45 | 41.8 |
| Example 24 | Inv-24 | 6.52 | 40.8 |
| Example 25 | Inv-25 | 6.55 | 41.2 |
| Example 26 | Inv-26 | 6.58 | 41.5 |
| Example 27 | Inv-27 | 6.61 | 42.1 |
| Example 28 | Inv-28 | 6.50 | 41.6 |
| Example 29 | Inv-29 | 6.55 | 41.0 |
| Example 30 | Inv-30 | 6.50 | 41.3 |
| Example 31 | Inv-31 | 6.60 | 40.8 |
| Example 32 | Inv-32 | 6.55 | 41.5 |
| Example 33 | Inv-33 | 6.55 | 41.2 |
| Example 34 | Inv-34 | 6.50 | 41.7 |
| Example 35 | Inv-35 | 6.65 | 42.1 |
| Example 36 | Inv-36 | 6.60 | 41.3 |
| Example 37 | Inv-37 | 6.62 | 40.9 |
| Example 38 | Inv-38 | 6.50 | 41.2 |
| Example 39 | Inv-39 | 6.45 | 40.6 |
| Example 40 | Inv-40 | 6.52 | 41.0 |
| Example 41 | Inv-41 | 6.50 | 40.7 |
| Example 42 | Inv-42 | 6.60 | 41.1 |
| Example 43 | Inv-43 | 6.45 | 41.0 |
| Example 44 | Inv-44 | 6.52 | 40.5 |
| Example 45 | Inv-45 | 6.55 | 40.9 |
| Example 46 | Inv-46 | 6.50 | 42.0 |
| Example 47 | Inv-47 | 6.51 | 41.9 |
| Example 48 | Inv-48 | 6.50 | 41.8 |
| Example 49 | Inv-49 | 6.45 | 42.1 |
| Example 50 | Inv-50 | 6.45 | 41.5 |
| Comparative Example 1 | CBP | 6.93 | 38.2 |
실험 결과, 본 발명에 따른 화학식 1로 표시되는 화합물(화합물 Inv-1 내지 Inv-50)을 발광층의 호스트 물질로 사용하는 실시예 1 내지 50에서 각각 제조된 유기 EL 소자는 종래 CBP를 사용하는 비교예 1의 유기 EL 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.As a result of the experiment, the organic EL devices manufactured in Examples 1 to 50 using the compounds represented by Formula 1 according to the present invention (Compounds Inv-1 to Inv-50) as host materials of the light emitting layer were compared using conventional CBP. It was confirmed that the organic EL device of Example 1 exhibited better performance in terms of current efficiency and driving voltage.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.
Claims (8)
- 하기 화학식 1로 표시되는 화합물: Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 식에서,WhereR6 및 R7 또는 R7 및 R8 중 적어도 하나는 하기 화학식 2와 축합 고리를 형성하고,At least one of R 6 and R 7 or R 7 and R 8 forms a condensed ring with the following Chemical Formula 2,[화학식 2] [Formula 2]
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4), Si(Ar5)(Ar6), P(Ar7) 및 B(Ar8)로 구성된 군으로부터 선택되고, X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ) and B (Ar 8 ) Become,R1 내지 R12 는 서로 같거나 또는 상이하고, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이들은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, R 1 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, substituted or unsubstituted C 1 -C 40 alkyl boron group, a substituted or unsubstituted C 6 ~ C 60 aryl group of boron, a substituted or unsubstituted C 6 ~ C 60 aryl phosphine group, a substituted or unsubstituted C 6 ~ C 60 aryl phosphine oxide group is selected from the pin, and the group consisting of a substituted or unsubstituted C 6 ~ C 60 aryl amine, these are combined tile adjacent may form a condensed ring,Ar1 내지 Ar8 은 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 니트로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기, 치환 또는 비치환된 C1~C40의 알킬보론기, 치환 또는 비치환된 C6~C60의 아릴보론기, 치환 또는 비치환된 C6~C60의 아릴포스핀기, 치환 또는 비치환된 C6~C60의 아릴포스핀옥사이드기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 구성된 군으로부터 선택되며,Ar 1 to Ar 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, substituted or unsubstituted C 1 -C 40 alkyl Boron group, substituted or unsubstituted C 6 ~ C 60 aryl boron group, substituted or unsubstituted C 6 ~ C 60 arylphosphine group, substituted or unsubstituted C 6 ~ C 60 aryl phosphine oxide group, and a substituted or unsubstituted C 6 ~ C 60 arylamine group,상기 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C6~C40의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다.The C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ group C 60 aryl silyl group, C 1 ~ alkyl boron C 40 of, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C of The arylamine groups of 6 to C 60 are each independently deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 6 to C 40 arylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ arylamine group of C 60 of It may be substituted with one or more substituents selected from the group consisting of. - 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 6 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 6.[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
상기 식에서,WhereX, R1 내지 R12, Ar1 내지 Ar8은 각각 제1항에서 정의된 바와 동일하다.X, R 1 to R 12 , Ar 1 to Ar 8 are the same as defined in claim 1, respectively. - 제 1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식으로 표시되는 화합물 군 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 a compound group represented by the following Chemical Formula:
상기 식에서,WhereR1 내지 R12, Ar1 내지 Ar8은 각각 제1항에서 정의된 바와 동일하다.R 1 to R 12 , Ar 1 to Ar 8 are the same as defined in claim 1, respectively. - 제1항에 있어서, 상기 Ar1 은 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되며, According to claim 1, Ar 1 is selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,상기 Ar2 내지 Ar8은 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되며, Ar 2 to Ar 8 are each independently a substituted or unsubstituted C 1 ~ C 40 alkyl group, a substituted or unsubstituted C 6 ~ C 60 aryl group, and a substituted or unsubstituted nuclear atom of 5 to 60 Is selected from the group consisting of heteroaryl groups,여기서, C1~C40의 알킬기, C6~C40의 아릴기 및 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, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C6~C40의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 하나 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물.Here, C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group and the number of nuclear atoms of 5 to 40 heteroaryl group, each independently selected from deuterium, halogen, cyano, C alkyl group of 1 ~ C 40, C 2 of the ~ of C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 Alkyloxy group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl group, C 6 to C 40 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl amine group selected from the group consisting of Compounds, which are unsubstituted or substituted with one or more substituents.
- 제1항에 있어서, 상기 X는 N(Ar2)이며, Ar1 및 Ar2는 서로 같거나 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되며, The method of claim 1, wherein X is N (Ar 2 ), Ar 1 and Ar 2 are the same as or different from each other, each independently substituted or unsubstituted C 6 ~ C 40 aryl group, and substituted or unsubstituted Selected from the group consisting of heteroaryl groups having 5 to 40 nuclear atoms,상기 C6~C40의 아릴기 및 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, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C6~C40의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 하나 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물.The C 6 ~ C 40 aryl group and 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 3 ~ C 40 cycloalkyl groups, heterocycloalkyl groups having 3 to 40 nuclear atoms, alkylsilyl groups of C 1 to C 40 , arylsilyl groups of C 6 to C 40 , alkylboron groups of C 1 to C 40 , C 6 to C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ substituted with one or more substituents selected from the aryl group consisting of an amine group of the C 60, or an unsubstituted of Compound which is characterized in that.
- 제 1항에 있어서, 상기 X는 N(Ar2)이며, R1 내지 R12 및 Ar1 내지 Ar2는 서로 같거나 또는 상이하며, 각각 독립적으로 수소 및 하기 치환체 군으로부터 선택되는 것을 특징으로 하는 화합물:The method of claim 1, wherein X is N (Ar 2 ), R One To R 12 And Ar One To Ar 2 It is the same as or different from each other, each independently selected from hydrogen and the following substituent group compound:
단, 상기 R1 내지 R12 중에서 화학식 2와 축합고리를 형성하는 R6와 R7 또는 R7와 R8는 제외된다. However, R 6 and R 7 or R 7 and R 8 forming a condensed ring with Formula 2 in R 1 to R 12 are excluded. - 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 제 1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. 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 the compound according to any one of claims 1 to 6. An organic electroluminescent device, characterized in that.
- 제7항에 있어서, 상기 화합물을 포함하는 적어도 하나의 유기물층은 정공 주입층, 정공 수송층 및 발광층으로 구성된 군으로부터 선택되는 것을 특징으로 하는 유기 전계 발광 소자.The organic electroluminescent device according to claim 7, wherein the at least one organic compound layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer.
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| WO2011116866A1 (en) * | 2010-03-24 | 2011-09-29 | Merck Patent Gmbh | Polymers of 8,9-dihydrobenzo[def]carbazole and their use as organic semiconductors |
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| WO2011116866A1 (en) * | 2010-03-24 | 2011-09-29 | Merck Patent Gmbh | Polymers of 8,9-dihydrobenzo[def]carbazole and their use as organic semiconductors |
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| HE,Z. ET AL.: "Largely Enhanced Efficiency with a PFN/Al Bilayer Cathode in High Efficiency Bulk Heterojunction Photovoltaic Cells with a Low Bandgap Polycarbazole Donor.", ADVANCED MATERIALS., vol. 23, 2011, pages 3086 - 3089 * |
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