WO2017188597A1 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
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- WO2017188597A1 WO2017188597A1 PCT/KR2017/002780 KR2017002780W WO2017188597A1 WO 2017188597 A1 WO2017188597 A1 WO 2017188597A1 KR 2017002780 W KR2017002780 W KR 2017002780W WO 2017188597 A1 WO2017188597 A1 WO 2017188597A1
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- Prior art keywords
- group
- aryl
- formula
- alkyl
- independently
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- 150000002894 organic compounds Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 239000012044 organic layer Substances 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 239000010410 layer Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000004429 atom Chemical group 0.000 claims description 42
- -1 alkyl boron Chemical compound 0.000 claims description 40
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 33
- 239000011368 organic material Substances 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 26
- 125000005104 aryl silyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 125000005264 aryl amine group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 239000008280 blood Substances 0.000 claims description 11
- 210000004369 blood Anatomy 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 5
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 5
- 239000002773 nucleotide Substances 0.000 claims description 3
- 125000003729 nucleotide group Chemical group 0.000 claims description 3
- 239000010977 jade Substances 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 16
- 230000015572 biosynthetic process Effects 0.000 description 122
- 238000003786 synthesis reaction Methods 0.000 description 122
- 238000002360 preparation method Methods 0.000 description 57
- 239000000463 material Substances 0.000 description 46
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 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 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- BEWZJUHGBZQONA-UHFFFAOYSA-N 3-bromo-6-phenyl-9h-carbazole Chemical compound C1=C2C3=CC(Br)=CC=C3NC2=CC=C1C1=CC=CC=C1 BEWZJUHGBZQONA-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 7
- XHFDSEFOADRRGX-UHFFFAOYSA-N 3-chloro-6-triphenylen-2-yl-9H-carbazole Chemical compound ClC=1C=CC=2NC3=CC=C(C=C3C=2C=1)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1 XHFDSEFOADRRGX-UHFFFAOYSA-N 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 4
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 4
- 0 CC(C)CC(C)=*(C1)C2C3C1C3C2 Chemical compound CC(C)CC(C)=*(C1)C2C3C1C3C2 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005092 sublimation method Methods 0.000 description 4
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- IAWRFMPNMXEJCK-UHFFFAOYSA-N 3-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 IAWRFMPNMXEJCK-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 2
- JPIYIAGTHDVLKD-UHFFFAOYSA-N 2-bromo-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Br)=NC=1C1=CC=CC=C1 JPIYIAGTHDVLKD-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- ZZVLQSXHLCYHJB-UHFFFAOYSA-N 3-chloro-6-(3,5-diphenylphenyl)-9H-carbazole Chemical compound C1(=CC=CC=C1)C1=CC(=CC(=C1)C=1C=CC=2NC3=CC=C(C=C3C=2C=1)Cl)C1=CC=CC=C1 ZZVLQSXHLCYHJB-UHFFFAOYSA-N 0.000 description 2
- FXIBQKSOJIYQDY-UHFFFAOYSA-N 3-chloro-6-(3-phenanthren-9-ylphenyl)-9H-carbazole Chemical compound ClC=1C=CC=2NC3=CC=C(C=C3C=2C=1)C1=CC(=CC=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1 FXIBQKSOJIYQDY-UHFFFAOYSA-N 0.000 description 2
- LGZDNHJMGGWQBF-UHFFFAOYSA-N 3-chloro-6-fluoranthen-3-yl-9H-carbazole Chemical compound ClC=1C=CC=2NC3=CC=C(C=C3C=2C=1)C=1C=CC=2C3=CC=CC=C3C3=CC=CC=1C=23 LGZDNHJMGGWQBF-UHFFFAOYSA-N 0.000 description 2
- CABSFELLEWZIAK-UHFFFAOYSA-N 3-chloro-9h-carbazole Chemical compound C1=CC=C2C3=CC(Cl)=CC=C3NC2=C1 CABSFELLEWZIAK-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- KUOJXLNHAYHPTM-UHFFFAOYSA-N C[IH][n]1c2ccccc2c2ccccc12 Chemical compound C[IH][n]1c2ccccc2c2ccccc12 KUOJXLNHAYHPTM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- LDKOCTYZOQNBJM-UHFFFAOYSA-N [9-phenyl-6-(9-phenylcarbazol-3-yl)carbazol-3-yl]boronic acid Chemical compound C12=CC=C(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 LDKOCTYZOQNBJM-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
- 230000008901 benefit Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 235000012736 patent blue V Nutrition 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NGZGJCQVEUFTHA-UHFFFAOYSA-N (3-phenanthren-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C3=CC=CC=C3C3=CC=CC=C3C=2)=C1 NGZGJCQVEUFTHA-UHFFFAOYSA-N 0.000 description 1
- YSDJLONVLIHBRC-UHFFFAOYSA-N (3-triphenylen-2-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 YSDJLONVLIHBRC-UHFFFAOYSA-N 0.000 description 1
- OQSQBELHOFEFQL-UHFFFAOYSA-N (4-dibenzofuran-2-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(OC=2C3=CC=CC=2)C3=C1 OQSQBELHOFEFQL-UHFFFAOYSA-N 0.000 description 1
- XUKACIDLJPTDTL-UHFFFAOYSA-N (4-dibenzothiophen-4-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=C1SC1=CC=CC=C12 XUKACIDLJPTDTL-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- 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
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- BCEMVHZPTKWHDZ-UHFFFAOYSA-N 10-bromo-7-phenylbenzo[c]carbazole Chemical compound C12=CC=C3C=CC=CC3=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 BCEMVHZPTKWHDZ-UHFFFAOYSA-N 0.000 description 1
- MDXQOGLSHJGDIB-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-1,3,5-triazine Chemical compound CC=1C=C(C=C(C1)C)C1=NC=NC=N1 MDXQOGLSHJGDIB-UHFFFAOYSA-N 0.000 description 1
- KVAFGXLNRKRGJJ-UHFFFAOYSA-N 2-(4-naphthalen-1-ylphenyl)quinazoline Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC2=CC=CC=C2C=N1 KVAFGXLNRKRGJJ-UHFFFAOYSA-N 0.000 description 1
- LSUOFHQPCBPIPH-UHFFFAOYSA-N 2-(9h-carbazol-3-yl)-9h-carbazole Chemical compound C1=C2NC3=CC=CC=C3C2=CC=C1C1=CC=C2NC3=CC=CC=C3C2=C1 LSUOFHQPCBPIPH-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
- VOBIWBJOWUGVER-UHFFFAOYSA-N 2-[3-[3-(3-bromophenyl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2C=C(C=CC=2)C=2C=C(C=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 VOBIWBJOWUGVER-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- VDDAVZWCRBHDLQ-UHFFFAOYSA-N 2-phenylquinazoline Chemical compound C1=CC=CC=C1C1=NC=C(C=CC=C2)C2=N1 VDDAVZWCRBHDLQ-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
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- H10K50/00—Organic light-emitting devices
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- 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
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Definitions
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission.
- An organic electroluminescent device having efficiency and improved lifespan characteristics.
- the organic electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device') of blue electroluminescence using anthracene single crystal was observed based on observation of Bernanose organic thin film emission in the 1950s. Research has continued. 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.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color, depending on the light emission color.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
- phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp).
- Metal complex compounds containing Ir, such as 2 are used.
- 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
- An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.
- Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage, high luminous efficiency, and improved lifespan characteristics.
- the present invention provides a compound represented by the following formula (1):
- L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
- Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
- n and m are each independently an integer of 0 to 3
- R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
- the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a 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 ⁇ mono or diaryl phosphine of C 60 blood group
- the present invention provides a composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
- g and j are each independently an integer from 0 to 4.
- h and i are each independently an integer from 0 to 3;
- Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
- R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of each other Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ⁇ C 40 alkyl phosphine group, C 1 ⁇ alkyl Phosphinicosuccinic group of C 40, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl
- the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
- Alkyl as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
- alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- Aryl in the present invention means a monovalent substituent derived from a C6 to C60 aromatic hydrocarbon combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
- Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
- R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- cycloalkyl is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
- condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
- the compound of the present invention is excellent in thermal stability and phosphorescence properties, it can be usefully applied as a material of the organic material layer of the organic electroluminescent device.
- the organic electroluminescent device comprising the compound according to the present invention in the organic material layer enables to manufacture an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life, and furthermore, the performance and lifespan are greatly improved.
- Color display panels can also be manufactured.
- L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
- Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
- n and m are each independently an integer of 0 to 3
- R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
- the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a 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 ⁇ mono or diaryl phosphine of C 60 blood group
- the present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence properties, and more particularly, a wide band gap (sky blue to red) by controlling energy levels by various substituents symmetric or asymmetric to the carbazole base skeleton. It provides a compound having). However, at this time, the coupling position thereof is not particularly limited.
- novel organic compound provided by the present invention is characterized by represented by the following formula (1):
- L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
- Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
- n and m are each independently an integer of 0 to 3
- R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
- the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a 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 ⁇ mono or diaryl phosphine of C 60 blood group
- the compound of Formula 1 which is used as a phosphorescent host in the present invention, has a wide bandgap (sky blue to red) by controlling energy levels by various substituents symmetrical or asymmetric to the carbazole-based skeleton. Therefore, when the compound represented by Chemical Formula 1 is used in the organic material layer of the organic electroluminescent device, the phosphorescence property may be improved, and the electron and / or hole transport ability and the light emission capability may be enhanced.
- the compound represented by Formula 1 of the present invention exhibits excellent properties as a light emitting host material compared to the conventional CBP due to the electrochemical stability due to the substitution of carbazole 3, 6 position, the host material of the light emitting layer More preferably used as.
- the compound represented by Chemical Formula 1 has various aromatic rings bonded to the carbazole-based basic skeleton as a substituent to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature and thus higher than the conventional CBP. May have thermal stability.
- the entire molecule has a bipolar (bipolar) nature of the various aromatic ring substituents to increase the binding force between the hole and the electron, it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP.
- the compound represented by Formula 1 is an N-type material having an electron withdrawing property having a high electron absorbing property
- the substituent bonded to the carbazole base skeleton is excellent when the hole transport compound is used as the second host.
- An organic electroluminescent device having light emission performance, low driving voltage, high efficiency and long life can be manufactured.
- the bandgap is equal to or greater than that of the compound of Formula 1 or a material having a greater LUMO value, when mixed with the compound of Formula 1 in an appropriate ratio, the injected holes and electrons are balanced to provide an organic light emitting device. Can help improve overall performance, especially lifespan.
- Formula 1 may be represented by the following Formula 2:
- L 1 to L 4 , Ar 1 to Ar 3 , n, m, R 1 and R 2 are each as defined in Formula 1.
- the Ar 1 may be selected from the group consisting of substituents of the following Chemical Formulas 3 to 8:
- a and b are each independently an integer of 0 to 4.
- X 1 to X 5 and X 7 to X 12 are each independently N or C (R 3 );
- X 6 is O or S
- R 3 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ mono or diaryl phosphine of C 60 blood
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 3 to R 5 Boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, halogen C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60
- Ar 2 and Ar 3 may be selected from the group consisting of the following substituents:
- Z 1 to Z 5 are the same as or different from each other, and are each independently N or C (R 6 );
- Y 1 and Y 2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, C (R 7 ) (R 8 ), N (R 9 ), O and S, but both Y 1 and Y 2 Not a single bond;
- c is an integer from 0 to 3;
- d and e are each independently an integer of 0 to 4.
- f is an integer from 0 to 2;
- R 6 to R 12 are the same as or different from each other, and are each independently selected from a group consisting of deuterium, a halogen, a cyano group, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, or are bonded to an adjacent group To form a condensed ring,
- the aryl group and heteroaryl group of R 6 to R 12 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alky Neyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine aryl boron group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 of Unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a C 6 -C 60 arylphosphine group, a C 6 -C 60
- the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
- composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
- g and j are each independently an integer from 0 to 4.
- h and i are each independently an integer from 0 to 3;
- Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
- R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of each other Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ⁇ C 40 alkyl phosphine group, C 1 ⁇ alkyl Phosphinicosuccinic group of C 40, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl
- Formula 9 may be represented by the following Formula 10 to 13.
- Ar 4 and Ar 5 , g, h, i, j, R 13 to R 16 are each the same as defined in Formula 9.
- the Ar 4 And Ar 5 may be the same as or different from each other, and may be each independently an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 40 nuclear atoms.
- the compound represented by Formula 9 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto:
- organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
- the organic electroluminescent device includes (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode, At least one of the one or more organic material layers may include a compound represented by Formula 1, and preferably include a composition including at least one of compounds represented by Formula 1 and compounds represented by Formula 9, respectively. have.
- At least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
- the organic material layer including the compound of Formula 1 may be a light emitting layer.
- the light emitting layer of the organic EL device may include a host material, wherein the host material may include the compound of formula (1).
- the compound of Formula 1 when included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
- the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material, and more preferably, the compound of Chemical Formula 9 is the first phosphorescent host of the emission layer, The compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
- the structure of the organic electroluminescent device 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.
- an electron injection layer may be further stacked on the electron transport layer.
- at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer may be represented by Formula 1 according to the present invention.
- It may include a compound, preferably as a host of the light emitting layer may include a compound represented by the formula (1) according to the present invention, more preferably, the compound of formula 9 according to the present invention as a first phosphorescent host of the light emitting layer
- the compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
- the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
- the organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- a ceramic crucible having high thermal conductivity is used as a method of forming the organic layer of the organic electroluminescent device by vacuum deposition, and should be designed so that stepwise and continuous evaporation control is possible and no organic splashing occurs.
- the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained.
- the organic material will be discolored or discolored during deposition.
- the organic material has a characteristic of being deposited by melting or sublimation depending on the material.
- the compound In the case of deposition by the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the case of the melting method The solid is vaporized through the liquid to form an organic layer.
- the melting method since the material undergoes one more phase change than the sublimation method, it is difficult to control the deposition temperature or the uniformity.
- the compound represented by Chemical Formula 1 according to the present invention may be deposited by a sublimation method and may have uniform thin film properties, thereby improving light emission characteristics.
- the compound of Formula 1 according to the present invention when used as a hole injection / transport layer material or a blue, green and / or red phosphorescent host material, an electron injection / transport layer material of an organic electroluminescent device, For example, compared to CBP), the efficiency and lifespan of the organic EL device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
- 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.
- the positive electrode material usable include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- usable negative electrode materials 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.
- 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.
- Step 1 3- Chloro -6- ( Triphenyl 2-yl) -9H- Carbazole (3-chloro-6- ( triphenylen -2-yl) -9H-carbazole)
- Step 1 3- Chloro -6- (3- (phenanthren-9-yl) phenyl) -9H- Carbazole synthesis
- 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in ⁇ step 2> of Preparation Example 5 3-chloro-6- ( Naphthalene-2 instead of (9,9-dimethyl-9H-flowen-2-yl) boronic acid using 3- (phenanthren-9-yl) phenyl) -9H-carbazole (4.53 g, 10 mmol)
- A-6 was obtained by the same procedure as in ⁇ Step 2> of Preparation Example 5, except that ilboonic acid (1.71 g, 10.0 mmol) was used.
- Step 1 3-([1,1 ': 3', 1 "- Terphenyl ] -5'-day) -6- Chloro -9H- Carbazole Synthesis of (3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -6-chloro-9H-carbazole)
- Step 1 3- Chloro -6- ( Fluoranthene -3-yl) -9H- Carbazole (3-chloro-6- ( fluoranthen Synthesis of -3-yl) -9H-carbazole)
- Step 1 4- (6- Chloro -9H- Carbazole -3 days)- N, N - Diphenylaniline synthesis
- Step 1 N-([1,1'- Biphenyl ] -4-yl) -N- (4- (6- Chloro -9H- Carbazole Synthesis of -3-yl) phenyl) -9,9-dimethyl-9H-flowen-2-amine
- a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ 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.
- ITO Indium tin oxide
- m-MTDATA, TCTA, PD-1, BCP used is as follows.
- m-MTDATA 60 nm
- TCTA 80 nm
- 50% was prepared using the following H-27 as the first host and the compound of Table 2 as the second host.
- An organic EL device was fabricated by stacking 1 host + 50% second host + 10% PD-1 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order. .
- Example 10 50% H-27 + 50% J-97 5.49 43.2 200
- Example 11 50% H-27 + 50% J-98 5.45 43.1 180
- Example 12 50% H-27 + 50% J-102 5.59 43.3 155
- Example 13 50% H-27 + 50% J-106 5.35 43.5
- Example 14 50% H-27 + 50% J-110 5.49 43.2 150
- Example 15 50% H-27 + 50% J-114 5.35 42.5
- Example 16 50% H-27 + 50% J-118 5.52 44.2 165
- Example 17 50% H-27 + 50% J-122 5.44 43.6 170
- An organic EL device was manufactured in the same manner as in Example 1, except that 100% of the following CBP was used as a host material in forming the emission layer in Example 1.
- An organic EL device was manufactured in the same manner as in Example 1, except that 100% of J-97 was used as a host material in forming the emission layer in Example 1.
- the organic EL device of Examples 1 to 17 using the compound represented by Chemical Formula 6 of the present invention as the first host material of the light emitting layer uses CBP or J-97 as the sole host material. It was confirmed that the organic EL devices of Comparative Examples 1 and 2 exhibited superior performance in terms of current efficiency and driving voltage.
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission.
- An organic electroluminescent device having efficiency and improved lifespan characteristics.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent device comprising the same and, more specifically, to: a novel carbazole-based compound having excellent thermal stability, phosphorescence characteristics, and the like; and an organic electroluminescent device comprising the same in one or more organic layers, thereby having a low driving voltage, high luminous efficiency, and improved lifespan characteristics.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 열적 안정성 및 인광 특성 등이 우수한 신규한 카바졸계 화합물 및 이를 하나 이상의 유기물층에 포함하여 낮은 구동 전압과 높은 발광 효율 및 향상된 수명 특성을 갖는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission. An organic electroluminescent device having efficiency and improved lifespan characteristics.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 유기 전계 발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구가 이어져 왔다. 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후, 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. The organic electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device') of blue electroluminescence using anthracene single crystal was observed based on observation of Bernanose organic thin film emission in the 1950s. Research has continued. 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 EL 소자에서는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic EL device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
유기 EL 소자의 발광층 형성 재료는 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/도펀트 계를 사용할 수 있다. The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color, depending on the light emission color. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료는 이론적으로 형광 재료에 비해 최대 4배의 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 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 phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, 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 청색(blue), 녹색(green), 적색(red) 도판트 재료로서 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등의 Ir을 포함하는 금속 착체 화합물이 사용되고 있다. 현재까지는 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)가 인광 호스트 재료로서 우수한 특성을 나타내고 있다. Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp). Metal complex compounds containing Ir, such as 2 , are used. To date, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 떨어지기 때문에, OLED 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하는 실정이다. 따라서, 보다 성능이 뛰어난 재료의 개발이 요구되고 있다.However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and low thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of the material which is more excellent in performance is calculated | required.
본 발명은 높은 유리 전이온도를 가지고, 열적 안정성이 우수하면서, 정공과 전자와의 결합력을 향상시킬 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압, 높은 발광 효율을 나타내며 수명 특성 등이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage, high luminous efficiency, and improved lifespan characteristics.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
L1 내지 L4는 서로 동일하거나 상이하고 각각 독립적으로 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며,L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
Ar1은 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기이며;Ar 1 is C 6 ~ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
Ar2 및 Ar3은 서로 상이하고, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되고,Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ~ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
n 및 m는 각각 독립적으로 0 내지 3의 정수이고,n and m are each independently an integer of 0 to 3,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되고; R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, Ar1
내지 Ar3의 아릴기 및 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, a 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 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C substituted with at least 60 group consisting arylsilyl the selected one more substituents or being unsubstituted, a plurality of substituents When substituted with, they may be the same or different from each other.
상기 목적을 달성하기 위하여, 본 발명은 상기 화학식 1로 표시되는 화합물 및 하기 화학식 9로 표시되는 화합물을 포함하는 유기 전계 발광 소자용 조성물을 제공한다:In order to achieve the above object, the present invention provides a composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
[화학식 9][Formula 9]
상기 화학식 9에서,In Chemical Formula 9,
g 및 j는 각각 독립적으로 0 내지 4의 정수이고;g and j are each independently an integer from 0 to 4;
h 및 i는 각각 독립적으로 0 내지 3의 정수이고;h and i are each independently an integer from 0 to 3;
Ar4 및 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 40개의 헤테로아릴기이며;Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
R13 내지 R16은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C40의 알킬포스핀기, C1~C40의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되며, Of R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of each other Alkynyl group, C 6 ~ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ~ C 40 alkyl phosphine group, C 1 ~ alkyl Phosphinicosuccinic group of C 40, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine blood group, C 6 of ~ C 60 aryl phosphine oxide is selected from the pin group and a C 6 ~ C 60 aryl silyl group of the group consisting of,
상기 Ar4, Ar5 및 R13 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, 할로겐C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.Ar 4 , Ar 5, and R 13 to R 16 alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkyloxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl groups , Alkyl boron group, aryl boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group , Halogen 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 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 Aryloxy group of -C 60 , C 1 -C 40 alkyloxy group, arylamine group of C 6 -C 60 , cycloalkyl group of C 3 -C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine of When substituted or unsubstituted with one or more substituents selected from the group consisting of a pinyl group, a C 6 -C 60 arylphosphine oxide group and a C 6 -C 60 arylsilyl group, they are the same as each other. Or may be different and combine with adjacent groups to form a condensed ring.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
본 발명에서 "알킬"은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다."Alkyl" as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다."Aryl" in the present invention means a monovalent substituent derived from a C6 to C60 aromatic hydrocarbon combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 40개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다."Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 "아릴아민"은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.By "cycloalkyl" is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다."Heterocycloalkyl" as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 6 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층의 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability and phosphorescence properties, it can be usefully applied as a material of the organic material layer of the organic electroluminescent device.
또한, 본 발명에 따른 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 우수한 발광 성능, 낮은 구동 전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있도록 하며, 나아가 성능, 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있도록 한다.In addition, the organic electroluminescent device comprising the compound according to the present invention in the organic material layer enables to manufacture an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life, and furthermore, the performance and lifespan are greatly improved. Color display panels can also be manufactured.
하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
L1 내지 L4는 서로 동일하거나 상이하고 각각 독립적으로 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며,L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
Ar1은 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기이며;Ar 1 is C 6 ~ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
Ar2 및 Ar3은 서로 상이하고, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되고,Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ~ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
n 및 m는 각각 독립적으로 0 내지 3의 정수이고,n and m are each independently an integer of 0 to 3,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되고; R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, Ar1
내지 Ar3의 아릴기 및 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, a 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 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C substituted with at least 60 group consisting arylsilyl the selected one more substituents or being unsubstituted, a plurality of substituents When substituted with, they may be the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New Organic Compounds
본 발명은 열적 안정성 및 인광 특성 등이 우수한 신규한 카바졸계 화합물 에 관한 것으로, 보다 상세하게는 카바졸계 기본 골격에 대칭 또는 비대칭의 여러 치환체에 의해 에너지 레벨이 조절됨으로써 넓은 밴드갭 (sky blue ~ red)을 갖는 화합물을 제공한다. 단, 이때 이들의 결합 위치는 특별히 제한되지 않는다.The present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence properties, and more particularly, a wide band gap (sky blue to red) by controlling energy levels by various substituents symmetric or asymmetric to the carbazole base skeleton. It provides a compound having). However, at this time, the coupling position thereof is not particularly limited.
구체적으로, 본 발명에서 제공하는 신규 유기 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다:Specifically, the novel organic compound provided by the present invention is characterized by represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
L1 내지 L4는 서로 동일하거나 상이하고 각각 독립적으로 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며,L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
Ar1은 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기이며;Ar 1 is C 6 ~ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
Ar2 및 Ar3은 서로 상이하고, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되고,Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ~ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
n 및 m는 각각 독립적으로 0 내지 3의 정수이고,n and m are each independently an integer of 0 to 3,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되고; R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, Ar1
내지 Ar3의 아릴기 및 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, a 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 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C substituted with at least 60 group consisting arylsilyl the selected one more substituents or being unsubstituted, a plurality of substituents When substituted with, they may be the same or different from each other.
본 발명에서 인광 호스트로 사용되는 상기 화학식 1의 화합물은, 카바졸계 기본 골격에 대칭 또는 비대칭의 여러 치환체에 의해 에너지 레벨이 조절됨으로써 넓은 밴드갭 (sky blue ~ red)을 갖는다. 따라서, 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층에 사용할 경우 인광특성이 개선됨과 동시에 전자 및/또는 정공 수송 능력, 발광 능력을 높일 수 있다.The compound of Formula 1, which is used as a phosphorescent host in the present invention, has a wide bandgap (sky blue to red) by controlling energy levels by various substituents symmetrical or asymmetric to the carbazole-based skeleton. Therefore, when the compound represented by Chemical Formula 1 is used in the organic material layer of the organic electroluminescent device, the phosphorescence property may be improved, and the electron and / or hole transport ability and the light emission capability may be enhanced.
또한 본 발명의 화학식 1로 표시되는 화합물은 카바졸 3,6번 위치의 치환으로 인한 전기 화학적 안정성으로 인하여 종래의 CBP에 비해 발광 호스트 물질로서 우수한 특성을 나타내기 때문에, 발광층의 호스트(host) 물질로 사용되는 것이 더욱 바람직하다.In addition, the compound represented by Formula 1 of the present invention exhibits excellent properties as a light emitting host material compared to the conventional CBP due to the electrochemical stability due to the substitution of carbazole 3, 6 position, the host material of the light emitting layer More preferably used as.
구체적으로, 상기 화학식 1로 표시되는 화합물은 카바졸계 기본골격에 다양한 방향족 환(aromatic ring)이 치환체로 결합되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상되고 이로 인해 종래 CBP보다 높은 열적 안정성을 가질 수 있다. 또한 다양한 방향족 환 치환체로 인해 분자 전체가 바이폴라(bipolar)한 성격을 가지면서 정공과 전자의 결합력을 높일 수 있기 때문에, 종래 CBP에 비해 발광층의 호스트 재료로서의 우수한 특성을 나타낼 수 있다.Specifically, the compound represented by Chemical Formula 1 has various aromatic rings bonded to the carbazole-based basic skeleton as a substituent to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature and thus higher than the conventional CBP. May have thermal stability. In addition, since the entire molecule has a bipolar (bipolar) nature of the various aromatic ring substituents to increase the binding force between the hole and the electron, it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP.
특히 상기 화학식 1로 표시되는 화합물이 카바졸계 기본 골격에 결합되는 치환체가 전자 흡수성이 큰 전자 끄는 작용기(electron withdrawing) 특성을 가진 N-type 물질일 경우, 정공 수송성 화합물을 제 2호스트로 사용하면 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있다. 또한, 상기 화학식 1의 화합물보다 밴드갭이 동등 이상이거나 LUMO값이 큰 재료이므로, 상기 화학식 1의 화합물과 적정 비율로 혼합하여 사용하는 경우, 주입되는 정공과 전자의 균형을 맞추어, 유기전계 발광소자의 제반 성능, 특히 수명 향상에 도움이 될 수 있다.Particularly, when the compound represented by Formula 1 is an N-type material having an electron withdrawing property having a high electron absorbing property, the substituent bonded to the carbazole base skeleton is excellent when the hole transport compound is used as the second host. An organic electroluminescent device having light emission performance, low driving voltage, high efficiency and long life can be manufactured. In addition, since the bandgap is equal to or greater than that of the compound of Formula 1 or a material having a greater LUMO value, when mixed with the compound of Formula 1 in an appropriate ratio, the injected holes and electrons are balanced to provide an organic light emitting device. Can help improve overall performance, especially lifespan.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 1은 하기 화학식 2로 표시되는 것일 수 있다:According to one preferred embodiment of the present invention, Formula 1 may be represented by the following Formula 2:
[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,
L1 내지 L4, Ar1 내지 Ar3, n, m, R1 및 R2 각각은 화학식 1에서 정의된 바와 같다.L 1 to L 4 , Ar 1 to Ar 3 , n, m, R 1 and R 2 are each as defined in Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 상기 Ar1는 하기 화학식 3 내지 8의 치환기로 이루어진 군에서 선택되는 것일 수 있다:According to one preferred embodiment of the present invention, the Ar 1 may be selected from the group consisting of substituents of the following Chemical Formulas 3 to 8:
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
상기 화학식 3 내지 화학식 8에서,In Chemical Formulas 3 to 8,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
a 및 b는 각각 독립적으로 0 내지 4의 정수이고;a and b are each independently an integer of 0 to 4;
X1 내지 X5 및 X7 내지 X12는 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 5 and X 7 to X 12 are each independently N or C (R 3 );
X6은 O 또는 S이며;X 6 is O or S;
R3 내지 R5는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,R 3 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an alkyl of C 1 ~ C 40 Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ mono or diaryl phosphine of C 60 blood group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ the group consisting of an aryl amine of the C 60 May be selected from or combined with adjacent groups to form a condensed ring,
상기 R3 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, 할로겐C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 3 to R 5 Boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, halogen C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ mono or diaryl phosphine blood group of C 60, C 6 ~ C When substituted or unsubstituted with one or more substituents selected from the group consisting of 60 arylphosphine oxide groups and C 6 -C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar2 및 Ar3은 아래의 치환기로 이루어진 군에서 선택되는 것일 수 있다:According to one preferred embodiment of the present invention, Ar 2 and Ar 3 may be selected from the group consisting of the following substituents:
상기 화학식 A-1 내지 A-24에서,In Chemical Formulas A-1 to A-24,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R6)이며;Z 1 to Z 5 are the same as or different from each other, and are each independently N or C (R 6 );
Y1 및 Y2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합, C(R7)(R8), N(R9), O 및 S로 이루어진 군에서 선택되나, Y1 및 Y2 모두 단일결합은 아니며;Y 1 and Y 2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, C (R 7 ) (R 8 ), N (R 9 ), O and S, but both Y 1 and Y 2 Not a single bond;
c는 0 내지 3의 정수이며; c is an integer from 0 to 3;
d 및 e는 각각 독립적으로 0 내지 4의 정수이며;d and e are each independently an integer of 0 to 4;
f는 0 내지 2의 정수이며;f is an integer from 0 to 2;
R6 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 중수소, 할로겐, 시아노기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, R 6 to R 12 are the same as or different from each other, and are each independently selected from a group consisting of deuterium, a halogen, a cyano group, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, or are bonded to an adjacent group To form a condensed ring,
상기 R6 내지 R12의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The aryl group and heteroaryl group of R 6 to R 12 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alky Neyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine aryl boron group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 of Unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, When substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 본 발명의 화학식1로 표시되는 화합물은 보다 구체적으로 아래의 화합물로 이루어진 군에서 선택될 수 있으나, 이에 한정되는 것은 아니다.According to one preferred embodiment of the present invention, the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 1로 표시되는 화합물 및 하기 화학식 9로 표시되는 화합물을 포함하는 유기 전계 발광 소자용 조성물을 형성할 수 있다: According to one preferred embodiment of the present invention, it is possible to form a composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
[화학식 9][Formula 9]
여기서,here,
g 및 j는 각각 독립적으로 0 내지 4의 정수이고;g and j are each independently an integer from 0 to 4;
h 및 i는 각각 독립적으로 0 내지 3의 정수이고;h and i are each independently an integer from 0 to 3;
Ar4 및 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 40개의 헤테로아릴기이며;Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
R13 내지 R16은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C40의 알킬포스핀기, C1~C40의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되며, Of R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of each other Alkynyl group, C 6 ~ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ~ C 40 alkyl phosphine group, C 1 ~ alkyl Phosphinicosuccinic group of C 40, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine blood group, C 6 of ~ C 60 aryl phosphine oxide is selected from the pin group and a C 6 ~ C 60 aryl silyl group of the group consisting of,
상기 Ar4, Ar5 및 R13 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, 할로겐C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.Ar 4 , Ar 5, and R 13 to R 16 alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkyloxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl groups , Alkyl boron group, aryl boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group , Halogen 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 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 Aryloxy group of -C 60 , C 1 -C 40 alkyloxy group, arylamine group of C 6 -C 60 , cycloalkyl group of C 3 -C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine of When substituted or unsubstituted with one or more substituents selected from the group consisting of a pinyl group, a C 6 -C 60 arylphosphine oxide group and a C 6 -C 60 arylsilyl group, they are the same as each other. Or may be different and combine with adjacent groups to form a condensed ring.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 9은 하기 화학식 10 내지 13로 표시되는 것일 수 있다:According to a preferred embodiment of the present invention, Formula 9 may be represented by the following Formula 10 to 13.
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
상기 화학식 10 내지 화학식 13에서,In Chemical Formulas 10 to 13,
Ar4 및 Ar5, g, h, i, j, R13 내지 R16 각각은 화학식 9에서 정의된 바와 동일하다.Ar 4 and Ar 5 , g, h, i, j, R 13 to R 16 are each the same as defined in Formula 9.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar4
및 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 40개의 헤테로아릴기인 것일 수 있다.According to a preferred embodiment of the present invention, the Ar 4 And Ar 5 may be the same as or different from each other, and may be each independently an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 40 nuclear atoms.
본 발명의 바람직한 한 구현 예에 따르면, 본 발명의 화학식 9로 표시되는 화합물은 보다 구체적으로 아래의 화합물로 이루어진 군에서 선택될 수 있으나, 이에 한정되는 것은 아니다:According to one preferred embodiment of the present invention, the compound represented by Formula 9 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto:
2. 유기 2. Organic
전계Electric field
발광 소자 Light emitting element
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다. On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
구체적으로, 본 발명에 따른 유기 전계 발광 소자는 (i) 양극(anode), (ii) 음극(cathode) 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하며, 바람직하게는 상기 화학식 1로 표시되는 화합물 및 화학식 9로 표시되는 화합물 중 각각 1종 이상을 포함하는 조성물을 포함할 수 있다.Specifically, the organic electroluminescent device according to the present invention includes (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode, At least one of the one or more organic material layers may include a compound represented by Formula 1, and preferably include a composition including at least one of compounds represented by Formula 1 and compounds represented by Formula 9, respectively. have.
본 발명의 일례에 따르면, 상기 유기 전계 발광 소자에 있어서, 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층일 수 있다.According to one embodiment of the present invention, in the organic electroluminescent device, at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Formula 1 may be a light emitting layer.
또한, 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 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다. 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 발광 소자에 포함될 수 있으며, 보다 바람직하게는 상기 화학식 9의 화합물은 발광층의 제1 인광 호스트로, 상기 화학식 1의 화합물은 발광층의 제2 인광 호스트로 사용될 수 있다.In addition, according to an example of the present invention, the light emitting layer of the organic EL 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 the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved. The compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material, and more preferably, the compound of Chemical Formula 9 is the first phosphorescent host of the emission layer, The compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
여기서, 상기 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있으며, 상기한 바와 같이, 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 본 발명에 따른 화학식 1로 표시되는 화합물을 포함할 수 있으며, 바람직하게는 발광층의 호스트로 본 발명에 따른 화학식 1로 표시되는 화합물을 포함할 수 있으며, 보다 바람직하게는 본 발명에 따른 화학식 9의 화합물은 발광층의 제1 인광 호스트로, 상기 화학식 1의 화합물은 발광층의 제2 인광 호스트로 사용될 수 있다.Here, the structure of the organic electroluminescent device 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, an electron injection layer may be further stacked on the electron transport layer. As described above, at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer may be represented by Formula 1 according to the present invention. It may include a compound, preferably as a host of the light emitting layer may include a compound represented by the formula (1) according to the present invention, more preferably, the compound of formula 9 according to the present invention as a first phosphorescent host of the light emitting layer The compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
또한, 본 발명에 따른 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
본 발명에 따른 유기 전계 발광 소자는 상기 유기물층 중 1층 이상 (예컨대, 발광층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 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 formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
한편, 진공 증착법을 통해 유기 전계 발광 소자의 유기물 층을 형성하는 방법으로는 높은 열 전도도를 가진 세라믹 도가니가 사용되며, 단계적이고 지속적인 증발 제어가 가능하고 유기물이 튀는 현상이 없도록 설계되어야 한다. 증발원의 온도 상승이 적절히 이루어지지 않아 지나치게 짧은 시간에 증발온도까지 도달한 유기물은 튀는 현상이 발생되어 증발원의 입구가 막히게 되고, 이로 인해 유기물의 증착 속도가 일정하지 않게 되어 원하는 박막 특성을 얻지 못하게 된다. 또한, 유기물이 증착 도중에 변색 또는 탈색될 가능성도 높아진다. 유기물은 물질에 따라 융해(Melting) 또는 승화(Sublimation)되어 증착되는 특성을 가지는데, 승화 방식으로 증착되는 경우는 화합물이 고체 상태에서 승화 과정을 거쳐 바로 유기물 층을 형성하는 반면, 융해 방식의 경우는 고체가 액체를 거쳐 기화되어 유기물 층을 형성한다. 융해 방식은 승화 방식에 비해 재료가 상변화를 한 단계 더 거치게 되므로, 증착 온도나 균일성을 컨트롤하기가 어렵다. 이때, 본 발명에 따른 화학식 1로 표시되는 화합물은 승화 방식으로 증착되어 균일한 박막 특성을 가질 수 있어 발광 특성이 개선된다.On the other hand, a ceramic crucible having high thermal conductivity is used as a method of forming the organic layer of the organic electroluminescent device by vacuum deposition, and should be designed so that stepwise and continuous evaporation control is possible and no organic splashing occurs. As the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained. . In addition, there is a high possibility that the organic material will be discolored or discolored during deposition. The organic material has a characteristic of being deposited by melting or sublimation depending on the material. In the case of deposition by the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the case of the melting method The solid is vaporized through the liquid to form an organic layer. In the melting method, since the material undergoes one more phase change than the sublimation method, it is difficult to control the deposition temperature or the uniformity. In this case, the compound represented by Chemical Formula 1 according to the present invention may be deposited by a sublimation method and may have uniform thin film properties, thereby improving light emission characteristics.
결과적으로, 본 발명에 따른 화학식 1의 화합물을 유기 전계 발광 소자의 정공 주입/수송층 재료 또는 청색, 녹색 및/또는 적색의 인광 호스트 재료, 전자 주입/수송층 재료로 사용할 경우, 종래의 유기물층 재료(예를 들어, CBP) 비해 유기 전계 발광 소자의 효율 및 수명을 크게 향상시킬 수 있다. 또한 이러한 유기 전계 발광 소자 수명 향상은 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.As a result, when the compound of Formula 1 according to the present invention is used as a hole injection / transport layer material or a blue, green and / or red phosphorescent host material, an electron injection / transport layer material of an organic electroluminescent device, For example, compared to CBP), the efficiency and lifespan of the organic EL device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
한편, 본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다. 또, 사용 가능한 양극 물질 로는 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. Meanwhile, 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. In addition, examples of the positive electrode material usable include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 사용 가능한 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지 않는다.In addition, usable negative electrode materials 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 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
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준비예Preparation
1] A-1의 합성 1] Synthesis of A-1
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단계1Step 1
> A-1의 합성> Synthesis of A-1
질소 기류 하에서 3-브로모-6-페닐-9H-카바졸(3-bromo-6-phenyl-9H-carbazole)(3.22g, 10mmol), [1,1'-바이페닐]-3-일보로닉 산([1,1'-biphenyl]-3-ylboronic acid)(1.98g, 10mmol), K2CO3 (2.76 g, 20 mmol), Pd(PPh3)4 (0.58g, 0.5mmol) 및 THF(60 mL)과 정제수(15ml)을 혼합하고 110℃ 에서 12시간 동안 교반하였다. 상온으로 식힌 후 H2O를 첨가하고 brine을 이용하여 추출하였다. Na2SO4로 수분을 제거한 후 유기층을 농축한 후 컬럼크로마토그래피를 실시하여 목적 화합물인 A-1 (2.77 g, 70%)를 얻었다. 3-bromo-6-phenyl-9H-carbazole (3.22 g, 10 mmol), [1,1'-biphenyl] -3-ylboro under nitrogen stream Nickic acid ([1,1'-biphenyl] -3-ylboronic acid) (1.98 g, 10 mmol), K 2 CO 3 (2.76 g, 20 mmol), Pd (PPh 3 ) 4 (0.58 g, 0.5 mmol) and THF (60 mL) and purified water (15 ml) were mixed and stirred at 110 ° C. for 12 h. After cooling to room temperature, H 2 O was added and extracted using brine. After removing moisture with Na 2 SO 4 , the organic layer was concentrated and subjected to column chromatography to obtain A-1 (2.77 g, 70%) as a target compound.
1H-NMR: δ 7.45 (m, 6H), 7.61 (d, 2H), 7.75 (m, 7H), 7.90 (m, 5H), 11.66 (s, 1H) 1 H-NMR: δ 7.45 ( m, 6H), 7.61 (d, 2H), 7.75 (m, 7H), 7.90 (m, 5H), 11.66 (s, 1H)
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준비예Preparation
2] A-2의 합성 2] Synthesis of A-2
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단계1Step 1
> A-2의 합성> Synthesis of A-2
준비예 1의 <단계 1>에서 사용된 [1,1'-바이페닐]-3-일보로닉 산([1,1'-biphenyl]-3-ylboronic acid) 대신 [1,1'-바이페닐]-4-일보로닉 산([1,1'-biphenyl]-4-ylboronic acid)(1.98 g, 10mmol)을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-2를 얻었다.[1,1'-bi instead of [1,1'-biphenyl] -3-ylboronic acid ([1,1'-biphenyl] -3-ylboronic acid) used in <Step 1> of Preparation Example 1 The same procedure as in <Step 1> of Preparation Example 1 was performed except that phenyl] -4-ylboronic acid ([1,1'-biphenyl] -4-ylboronic acid) (1.98 g, 10 mmol) was used. This gave A-2.
1H-NMR: δ 7.25 (m, 4H), 7.45 (m, 6H), 7.76 (m, 6H), 7.89 (m, 2H), 7.99 (m, 2H), 11.66 (s, 1H) 1 H-NMR: δ 7.25 (m, 4H), 7.45 (m, 6H), 7.76 (m, 6H), 7.89 (m, 2H), 7.99 (m, 2H), 11.66 (s, 1H)
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준비예Preparation
3] A-3의 합성 3] Synthesis of A-3
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단계1Step 1
> A-3의 합성> Synthesis of A-3
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸(3-bromo-6-phenyl-9H-carbazole) 대신 3-([1,1'-바이페닐]-3-일)-6-브로모-9H-카바졸(3-([1,1'-biphenyl]-3-yl)-6-bromo-9H-carbazole)(3.98 g, 10 mmol)을 사용하고 [1,1'-바이페닐]-3-일보로닉산([1,1'-biphenyl]-3-ylboronic acid) 대신 디벤조[b,d]퓨란-4-일보로닉산(dibenzo[b,d]furan-4-ylboronic acid)(2.12g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-3를 얻었다.3-([1,1'-biphenyl] instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1 3-yl) -6-bromo-9H-carbazole (3-([1,1'-biphenyl] -3-yl) -6-bromo-9H-carbazole) (3.98 g, 10 mmol) was used And dibenzo [b, d] furan-4-ylboronic acid (dibenzo [b] instead of [1,1'-biphenyl] -3-ylboronic acid. A-3 was obtained in the same manner as in <Step 1> of Preparation Example 1, except that, d] furan-4-ylboronic acid) (2.12 g, 10 mmol) was used.
1H-NMR: δ 7.50 (m, 9H), 7.70 (m, 5H), 8.00 (m, 8H), 11.64 (s, 1H) 1 H-NMR: δ 7.50 (m, 9H), 7.70 (m, 5H), 8.00 (m, 8H), 11.64 (s, 1H)
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준비예Preparation
4] A-4의 합성 4] Synthesis of A-4
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단계1Step 1
> A-4의 합성> Synthesis of A-4
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸(3-bromo-6-phenyl-9H-carbazole) 대신 3-([1,1'-바이페닐]-4-일)-6-브로모-9H-카바졸(3-([1,1'-biphenyl]-4-yl)-6-bromo-9H-carbazole)(3.98g, 10mmol)를 사용하고 [1,1'-바이페닐]-3-일보로닉산([1,1'-biphenyl]-3-ylboronic acid) 대신 디벤조[b,d]티오펜-2-일보로닉 산(dibenzo[b,d]thiophen-2-ylboronic acid)(2.28g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-4를 얻었다.3-([1,1'-biphenyl] instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1 4-yl) -6-bromo-9H-carbazole (3-([1,1'-biphenyl] -4-yl) -6-bromo-9H-carbazole) (3.98 g, 10 mmol) Dibenzo [b, d] thiophen-2-ylboronic acid (dibenzo [instead of [1,1'-biphenyl] -3-ylboronic acid) A-4 was obtained in the same manner as in <Step 1> of Preparation Example 1, except that b, d] thiophen-2-ylboronic acid) (2.28 g, 10 mmol) was used.
1H-NMR: δ 7.25 (m, 4H), 7.49 (m, 5H), 7.75 (m, 4H), 7.99 (m, 6H), 8.12 (m, 2H), 8.45 (d, 1H), 11.65 (s, 1H) 1 H-NMR: δ 7.25 (m, 4H), 7.49 (m, 5H), 7.75 (m, 4H), 7.99 (m, 6H), 8.12 (m, 2H), 8.45 (d, 1H), 11.65 ( s, 1 H)
[[
준비예Preparation
5] A-5의 합성 5] Synthesis of A-5
<<
단계1Step 1
> 3-> 3-
클로로Chloro
-6-(-6- (
트리페닐Triphenyl
-2-일)-9H-2-yl) -9H-
카바졸(3-chloro-6-Carbazole (3-chloro-6-
((
triphenylentriphenylen
-2-yl)-9H-carbazole)의 합성-2-yl) -9H-carbazole)
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-6-클로로-9H-카바졸 (2.80g, 10mmol)를 사용하고 [1,1'-바이페닐]-3-일 보로닉 산 대신 트리페닐렌-2-일보로닉 산(2.72g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸을 얻었다.Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-6-chloro-9H-carbazole (2.80 g, 10 mmol) was used, and [1, The same procedure as in <Step 1> of Preparation Example 1 was performed except that triphenylene-2-ylboronic acid (2.72 g, 10 mmol) was used instead of 1'-biphenyl] -3-yl boronic acid. This gave 3-chloro-6- (triphenylen-2-yl) -9H-carbazole.
1H-NMR: δ 7.09 (d, 1H), 7.60 (m, 9H), 7.89 (s, 1H), 7.99 (d, 1H), 8.35 (m, 3H), 9.26 (s, 1H), 9.60 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.09 (d, 1H), 7.60 (m, 9H), 7.89 (s, 1H), 7.99 (d, 1H), 8.35 (m, 3H), 9.26 (s, 1H), 9.60 ( d, 1 H), 11.63 (s, 1 H)
<<
단계2Step 2
> A-5의 합성> Synthesis of A-5
질소 기류 하에서 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸(4.27g, 10.0mmol), (9,9-다이메틸-9H-플로우렌-2-일)보로닉 산(2.38g, 10.0mmol), Cs2CO3
(6.51 g, 20.0 mmol), Pd(OAc)2
(0.11 g, 5 mol%), X-Phos (0.47 g, 1.00 mmol)를 120 ml / 40 ml의 THF/H2O에 넣고 90에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-5(3.51 g, 수율 60%)를 획득하였다.3-chloro-6- (triphenylen-2-yl) -9H-carbazole (4.27 g, 10.0 mmol), (9,9-dimethyl-9H-flowen-2-yl) boronic under nitrogen stream Acid (2.38 g, 10.0 mmol), Cs 2 CO 3 (6.51 g, 20.0 mmol), Pd (OAc) 2 (0.11 g, 5 mol%) and X-Phos (0.47 g, 1.00 mmol) were added to 120 ml / 40 ml of THF / H 2 O and stirred at 90 to 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain the target compound A-5 (3.51 g, yield 60%).
1H-NMR: δ 1.69 (s, 6H), 7.33 (m, 2H), 7.70 (m, 10H), 7.89 (m, 4H), 7.99 (m, 2H), 8.09 (d, 1H), 8.33 (m, 3H), 9.26 (s, 1H), 9.60 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.69 (s, 6H), 7.33 (m, 2H), 7.70 (m, 10H), 7.89 (m, 4H), 7.99 (m, 2H), 8.09 (d, 1H), 8.33 ( m, 3H), 9.26 (s, 1H), 9.60 (d, 1H), 11.63 (s, 1H)
[[
준비예Preparation
6] A-6의 합성 6] Synthesis of A-6
<<
단계1Step 1
> 3-> 3-
클로로Chloro
-6-(3-(페난트렌-9-일)페닐)-9H--6- (3- (phenanthren-9-yl) phenyl) -9H-
카바졸의Carbazole
합성 synthesis
준비예 5의 <단계 1>에서 사용된 트리페닐렌-2-일보로닉 산 대신 (3-(페난트렌-9-일)페닐)보로닉 산(2.98g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 3-클로로-6-(3-(페난트렌-9-일)페닐)-9H-카바졸을 얻었다.Except for using (3- (phenanthrene-9-yl) phenyl) boronic acid (2.98 g, 10 mmol) instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 Was subjected to the same process as in <Step 1> of Preparation Example 5 to obtain 3-chloro-6- (3- (phenanthren-9-yl) phenyl) -9H-carbazole.
1H-NMR: δ 7.09 (d, 1H), 7.66 (m, 10H), 7.95 (m, 5H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 (s, 1H) 1 H-NMR: δ 7.09 (d, 1H), 7.66 (m, 10H), 7.95 (m, 5H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)
<<
단계2Step 2
> A-6의 합성> Synthesis of A-6
준비예 5의 <단계 2>에서 사용된 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸 대신 상기 준비예 6의 <단계 1>에서 얻은 3-클로로-6-(3-(페난트렌-9-일)페닐)-9H-카바졸(4.53g, 10mmol)를 사용하고 (9,9-다이메틸-9H-플로우렌-2-일)보로닉 산 대신 나프탈렌-2-일보로닉 산(1.71g, 10.0mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 2>와 동일한 과정을 수행하여 A-6를 얻었다.Instead of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <step 2> of Preparation Example 5, 3-chloro-6- ( Naphthalene-2 instead of (9,9-dimethyl-9H-flowen-2-yl) boronic acid using 3- (phenanthren-9-yl) phenyl) -9H-carbazole (4.53 g, 10 mmol) A-6 was obtained by the same procedure as in <Step 2> of Preparation Example 5, except that ilboonic acid (1.71 g, 10.0 mmol) was used.
1H-NMR: δ 7.38 (d, 1H), 7.66 (m, 12H), 7.94 (m, 10H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 (s, 1H) 1 H-NMR: δ 7.38 (d, 1H), 7.66 (m, 12H), 7.94 (m, 10H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)
[[
준비예Preparation
7] A-7의 합성 7] Synthesis of A-7
<<
단계1Step 1
> 3-([1,1':3',1"-> 3-([1,1 ': 3', 1 "-
터페닐Terphenyl
]-5'-일)-6-] -5'-day) -6-
클로로Chloro
-9H--9H-
카바졸Carbazole
(3-([1,1':3',1''-terphenyl]-5'-yl)-6-chloro-9H-carbazole)의 합성Synthesis of (3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -6-chloro-9H-carbazole)
준비예 5의 <단계 1>에서 사용된 트리페닐렌-2-일보로닉 산 대신 [1,1':3',1''-터페닐]-5'-일보로닉 산(2.74g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 3-([1,1':3',1''-터페닐]-5'-일)-6-클로로-9H-카바졸을 얻었다.[1,1 ': 3', 1 ''-terphenyl] -5'-ilboronic acid (2.74 g, instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 Except that 10 mmol) was used, the same process as in <Step 1> of Preparation Example 5 was carried out to proceed with 3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl)- 6-chloro-9H-carbazole was obtained.
1H-NMR: δ 7.09 (d, 1H), 7.52 (m, 8H), 7.76 (m, 5H), 7.89 (s, 1H), 8.00 (m, 4H), 11.66 (s, 1H) 1 H-NMR: δ 7.09 (d, 1H), 7.52 (m, 8H), 7.76 (m, 5H), 7.89 (s, 1H), 8.00 (m, 4H), 11.66 (s, 1H)
<<
단계2Step 2
> A-7의 합성> Synthesis of A-7
준비예 5의 <단계 2>에서 사용된 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸 대신 상기 준비예 7의 <단계 1>에서 얻은 3-([1,1':3',1''-터페닐]-5'-일)-6-클로로-9H-카바졸(4.29g, 10mmol)을 사용하고 (9,9-다이메틸-9H-플로우렌-2-일)보로닉 산 대신 9,9'-스파이로바이[플로우렌]-4-일보로닉산 (3.60g, 10.0mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 2>와 동일한 과정을 수행하여 A-7를 얻었다.3-([1,1] obtained in <Step 1> of Preparation Example 7 in place of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 ': 3', 1 ''-terphenyl] -5'-yl) -6-chloro-9H-carbazole (4.29 g, 10 mmol) and (9,9-dimethyl-9H-flowene-2 Same as <Step 2> of Preparation Example 5, except that 9,9'-spirobi [flowene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used instead of boronic acid. The procedure was followed to obtain A-7.
1H-NMR: δ 7.47 (m, 16H), 7.65 (d, 1H), 7.77 (m, 7H), 7.89 (m, 10H), 11.66 (s, 1H) 1 H-NMR: δ 7.47 (m, 16H), 7.65 (d, 1H), 7.77 (m, 7H), 7.89 (m, 10H), 11.66 (s, 1H)
[[
준비예Preparation
8] A-8의 합성 8] Synthesis of A-8
<<
단계1Step 1
> 3-> 3-
클로로Chloro
-6-(-6- (
플루오란센Fluoranthene
-3-일)-9H--3-yl) -9H-
카바졸(3-chloro-6-Carbazole (3-chloro-6-
((
fluoranthenfluoranthen
-3-yl)-9H-carbazole)의 합성Synthesis of -3-yl) -9H-carbazole)
준비예 5의 <단계 1>에서 사용된 트리페닐렌-2-일보로닉 산 대신 플루오란센-3-일보로닉 산(2.46g, 10mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 3-클로로-6-(플루오란센-3-일)-9H-카바졸을 얻었다.Except for using fluoranthene-3-ylboronic acid (2.46g, 10mmol) instead of the triphenylene-2-ylboronic acid used in <step 1> of Preparation Example 5 of Preparation Example 5 The same procedure as in <Step 1> was followed to obtain 3-chloro-6- (fluoranthene-3-yl) -9H-carbazole.
1H-NMR: δ 7.09 (d, 1H), 7.37 (d, 1H), 7.50 (m, 3H), 7.66 (m, 4H), 7.89 (s, 1H), 8.00 (m, 3H), 8.42 (d, 2H), 11.65 (s, 1H) 1 H-NMR: δ 7.09 (d, 1H), 7.37 (d, 1H), 7.50 (m, 3H), 7.66 (m, 4H), 7.89 (s, 1H), 8.00 (m, 3H), 8.42 ( d, 2H), 11.65 (s, 1H)
<<
단계2Step 2
> A-8의 합성> Synthesis of A-8
준비예 5의 <단계 2>에서 사용된 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸 대신 상기 준비예 8의 <단계 1>에서 얻은 3-클로로-6-(플루오란센-3-일)-9H-카바졸(4.01g, 10mmol)를 사용하고 (9,9-다이메틸-9H-플루오렌-2-일)보로닉 산 대신 (4-(트리페닐실릴)페닐)보로닉 산(3.80g, 10.0mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 2>와 동일한 과정을 수행하여 A-8를 얻었다.3-Chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 3-chloro-6- (obtained in <Step 1> of Preparation Example 8 above Fluoransen-3-yl) -9H-carbazole (4.01 g, 10 mmol) was used instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (4- (triphenylsilyl) A-8 was obtained in the same manner as in <Step 2> of Preparation Example 5, except that (phenyl) boronic acid (3.80 g, 10.0 mmol) was used.
1H-NMR: δ 7.37 (m, 17H), 7.65 (m, 4H), 7.77 (m, 3H), 7.89 (m, 4H), 7.99 (m, 2H), 8.10 (d, 2H), 8.42 (d, 2H), 11.66 (s, 1H) 1 H-NMR: δ 7.37 (m, 17H), 7.65 (m, 4H), 7.77 (m, 3H), 7.89 (m, 4H), 7.99 (m, 2H), 8.10 (d, 2H), 8.42 ( d, 2H), 11.66 (s, 1H)
[[
준비예Preparation
9] A-9의 합성 9] Synthesis of A-9
<<
단계1Step 1
> 4-(6-> 4- (6-
클로로Chloro
-9H--9H-
카바졸Carbazole
-3-일)--3 days)-
N,NN, N
--
다이페닐아닐린의Diphenylaniline
합성 synthesis
준비예 5의 <단계 1>에서 사용된 트리페닐렌-2-일보로닉 산 대신 (4-(디페닐아미노)페닐)보로닉 산(2.89g, 10mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 4-(6-클로로-9H-카바졸-3-일)-N,N-디페닐아닐린을 얻었다.Preparation above except that (4- (diphenylamino) phenyl) boronic acid (2.89 g, 10 mmol) was used instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 4- (6-chloro-9H-carbazol-3-yl) -N, N-diphenylaniline was obtained in the same manner as in <Step 1> of Example 5.
1H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 4H), 7.77 (d, 1H), 7.89 (s, 1H), 7.99 (d, 1H), 11.65 (s, 1H) 1 H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 4H), 7.77 (d, 1H), 7.89 (s, 1H), 7.99 ( d, 1 H), 11.65 (s, 1 H)
<<
단계2Step 2
> A-9의 합성> Synthesis of A-9
준비예 5의 <단계 2>에서 사용된 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸 대신 상기 준비예 9의 <단계 1>에서 얻은 4-(6-클로로-9H-카바졸-3-일)-N,N-디페닐아닐린(4.44g, 10mmol)을 사용하고 (9,9-디메틸-9H-플로우렌-2-일)보로닉 산 대신 (7-페닐-7H-벤조[c]카바졸-10-일)보로닉 산(3.37g, 10.0mmol) 을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 2>와 동일한 과정을 수행하여 A-9를 얻었다.4- (6-chloro- obtained in <Step 1> of Preparation Example 9 instead of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 9H-carbazol-3-yl) -N, N-diphenylaniline (4.44 g, 10 mmol) was used instead of (9,9-dimethyl-9H-flowen-2-yl) boronic acid (7-phenyl A-9 was prepared by the same procedure as in <Step 2> of Preparation Example 5, except that -7H-benzo [c] carbazol-10-yl) boronic acid (3.37 g, 10.0 mmol) was used. Got it.
1H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 11H), 7.77 (d, 2H), 7.90 (m, 6H), 8.13 (d, 1H), 8.30 (d, 1H), 8.54 (d, 1H), 11.65 (s, 1H) 1 H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 11H), 7.77 (d, 2H), 7.90 (m, 6H), 8.13 ( d, 1H), 8.30 (d, 1H), 8.54 (d, 1H), 11.65 (s, 1H)
[[
준비예Preparation
10] A-10의 합성 10] Synthesis of A-10
<<
단계1Step 1
> N-([1,1'-> N-([1,1'-
바이페닐Biphenyl
]-4-일)-N-(4-(6-] -4-yl) -N- (4- (6-
클로로Chloro
-9H--9H-
카바졸Carbazole
-3-일)페닐)-9,9-디메틸-9H-플로우렌-2-아민의 합성Synthesis of -3-yl) phenyl) -9,9-dimethyl-9H-flowen-2-amine
준비예 5의 <단계 1>에서 사용된 트리페닐렌-2-일보로닉 산 대신 (4-([1,1'-바이페닐]-4-일(9,9-디메틸-9H-플로우렌-2-일)아미노)페닐)보로닉 산(4.81g, 10mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 1>과 동일한 과정을 수행하여 N-([1,1'-바이페닐]-4-일)-N-(4-(6-클로로-9H-카바졸-3-일)페닐)-9,9-디메틸-9H-플로우렌-2-아민을 얻었다.(4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-flowene) instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 Except for using 2--2-yl) amino) phenyl) boronic acid (4.81 g, 10 mmol), N-([1,1'-bi) was carried out in the same manner as in <Step 1> of Preparation Example 5 above. Phenyl] -4-yl) -N- (4- (6-chloro-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-9H-flowen-2-amine.
1H-NMR: δ 1.69 (s, 6H), 7.11 (m, 2H), 7.55 (m, 17H), 7.77 (m, 3H), 7.89 (m, 3H), 7.99 (d, 1H), 11.67 (s, 1H) 1 H-NMR: δ 1.69 (s, 6H), 7.11 (m, 2H), 7.55 (m, 17H), 7.77 (m, 3H), 7.89 (m, 3H), 7.99 (d, 1H), 11.67 ( s, 1 H)
<<
단계2Step 2
> A-10의 합성> Synthesis of A-10
준비예 5의 <단계 2>에서 사용된 3-클로로-6-(트리페닐렌-2-일)-9H-카바졸 대신 상기 준비예 10의 <단계 1>에서 얻은 N-([1,1'-바이페닐]-4-일)-N-(4-(6-클로로-9H-카바졸-3-일)페닐)-9,9-디메틸-9H-플로우렌-2-아민 (6.37g, 10mmol)을 사용하고 (9,9-디메틸-9H-플로우렌-2-일)보로닉 산 대신 (9-페닐-9H-카바졸-3-일)보로닉 산(2.87g, 10.0mmol)을 사용하는 것을 제외하고는 상기 준비예 5의 <단계 2>와 동일한 과정을 수행하여 A-10를 얻었다.N-([1,1] obtained in <Step 1> of Preparation Example 10 in place of the 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 '-Biphenyl] -4-yl) -N- (4- (6-chloro-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-9H-flowren-2-amine (6.37 g , 10 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) instead of (9,9-dimethyl-9H-flowen-2-yl) boronic acid A-10 was obtained by performing the same process as in <Step 2> of Preparation Example 5 except for using.
1H-NMR: δ 1.69 (s, 6H), 7.16 (m, 2H), 7.50 (m, 20H), 7.87 (m, 14H), 8.55 (d, 1H), 11.67 (s, 1H) 1 H-NMR: δ 1.69 (s, 6H), 7.16 (m, 2H), 7.50 (m, 20H), 7.87 (m, 14H), 8.55 (d, 1H), 11.67 (s, 1H)
[[
준비예Preparation
11] A-11의 합성 11] Synthesis of A-11
<<
단계1Step 1
> A-> A-
11 의Of 11
합성 synthesis
질소 기류 하에서 3-브로모-6-페닐-9H-카바졸 (3.22 g, 10 mmol), 11-페닐-11,12-디하이드로인돌[2,3-a]카바졸(3.32g, 10mmol), Pd(OAc)2 (0.22g, 1mmol), P(t-Bu)3 (0.47ml, 2mmol), NaO(t-Bu) (1.92g, 20mmol) 및 톨루엔 (100ml)를 혼합하고 110℃ 에서 2시간 동안 교반하였다. 반응이 종결된 후 톨루엔을 농축하고, 고체염을 filter 한 뒤, 재결정으로 정제하여 목적 화합물인 A-11 (2.86 g, 수율 50%)을 얻었다.3-bromo-6-phenyl-9H-carbazole (3.22 g, 10 mmol), 11-phenyl-11,12-dihydroindole [2,3-a] carbazole (3.32 g, 10 mmol) under a nitrogen stream , Pd (OAc) 2 (0.22g, 1mmol), P ( t -Bu) 3 (0.47ml, 2mmol), NaO ( t -Bu) (1.92g, 20mmol) and toluene (100ml) and mix at 110 ° C Stir for 2 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound A-11 (2.86 g, yield 50%).
1H-NMR: δ 7.16 (m, 2H), 7.50 (m, 17H), 7.90 (m, 4H), 8.12 (d, 1H), 8.55 (d, 2H), 11.66 (s, 1H) 1 H-NMR: δ 7.16 (m, 2H), 7.50 (m, 17H), 7.90 (m, 4H), 8.12 (d, 1H), 8.55 (d, 2H), 11.66 (s, 1H)
[[
준비예Preparation
12] A-12의 합성 12] Synthesis of A-12
<<
단계1Step 1
> A-12의 합성> Synthesis of A-12
준비예 11의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-6-(페닐-d5)-9H-카바졸(3.27g, 10mmol)를 사용하고 11-페닐-11,12-디하이드로인돌[2,3-a]카바졸 대신 14H-벤조[c]벤조[4,5]티에노[2,3-a]카바졸(3.23g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 11의 <단계 1>과 동일한 과정을 수행하여 A-12를 얻었다.3-bromo-6- (phenyl-d5) -9H-carbazole (3.27 g, 10 mmol) was used instead of the 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 11 14H-benzo [c] benzo [4,5] thieno [2,3-a] carbazole (3.23 g, 10 mmol) instead of 11-phenyl-11,12-dihydroindole [2,3-a] carbazole A-12 was obtained by performing the same process as <Step 1> of Preparation Example 11, except for using).
1H-NMR: δ 7.16 (t, 1H), 7.35 (m, 2H), 7.66 (m, 7H), 7.90 (m, 4H), 8.50 (m, 4H), 11.66 (s, 1H) 1 H-NMR: δ 7.16 (t, 1H), 7.35 (m, 2H), 7.66 (m, 7H), 7.90 (m, 4H), 8.50 (m, 4H), 11.66 (s, 1H)
[[
준비예Preparation
13] A-13의 합성 13] Synthesis of A-13
<<
단계1Step 1
> A-13의 합성> Synthesis of A-13
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-9H-카바졸 (2.46g, 10mmol)를 사용하고 [1,1'-바이페닐]-3-일 보로닉산 대신 (4-(디벤조[b,d]티오펜-4-일)페닐)보로닉 산(3.04g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-13를 얻었다.Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'-by Preparation Example 1 except that (4- (dibenzo [b, d] thiophen-4-yl) phenyl) boronic acid (3.04 g, 10 mmol) was used instead of phenyl] -3-yl boronic acid. A-13 was obtained by performing the same procedure as in <Step 1>.
1H-NMR: δ 7.22 (m, 5H), 7.66 (m, 6H), 7.93 (m, 3H), 8.19 (d, 1H), 8.32 (d, 1H), 8.45 (d, 1H), 8.55 (d, 1H), 11.66 (s, 1H) 1 H-NMR: δ 7.22 (m, 5H), 7.66 (m, 6H), 7.93 (m, 3H), 8.19 (d, 1H), 8.32 (d, 1H), 8.45 (d, 1H), 8.55 ( d, 1 H), 11.66 (s, 1 H)
[[
준비예Preparation
14] A-14의 합성 14] Synthesis of A-14
<<
단계1Step 1
> A-14의 합성> Synthesis of A-14
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-9H-카바졸(2.46g, 10mmol)을 사용하고 [1,1'-바이페닐]-3-일보로닉 산 대신 (4-(디벤조[b,d]퓨란-2-일)페닐)보로닉 산(2.88g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-14를 얻었다.Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'-by Preparation Example 1, except that (4- (dibenzo [b, d] furan-2-yl) phenyl) boronic acid (2.88 g, 10 mmol) was used instead of phenyl] -3-ylboronic acid. A-14 was obtained by performing the same procedure as in <Step 1>.
1H-NMR: δ 7.40 (m, 9H), 7.63 (d, 1H), 7.77 (m, 5H), 7.99 (m, 2H), 8.19 (d, 1H), 11.64 (s, 1H) 1 H-NMR: δ 7.40 (m, 9H), 7.63 (d, 1H), 7.77 (m, 5H), 7.99 (m, 2H), 8.19 (d, 1H), 11.64 (s, 1H)
[[
준비예Preparation
15] A-15의 합성 15] Synthesis of A-15
<<
단계1Step 1
> A-15의 합성> Synthesis of A-15
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-9H-카바졸(2.46g, 10mmol)를 사용하고 [1,1'-바이페닐]-3-일보로닉 산 대신 (3-(9,9-디메틸-9H-플루오렌-2-일)페닐)보로닉 산(3.14g, 10mmol)을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-15를 얻었다.Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'-by Preparation Example except for using (3- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) boronic acid (3.14 g, 10 mmol) instead of phenyl] -3-ylboronic acid A-15 was obtained by performing the same procedure as in <Step 1> of 1.
1H-NMR: δ 1.69 (s, 6H), 7.28 (m, 3H), 7.55 (m, 5H), 7.77 (m, 3H), 7.99 (m, 5H), 8.09 (d, 1H), 8.19 (d, 1H), 11.66 (s, 1H) 1 H-NMR: δ 1.69 (s, 6H), 7.28 (m, 3H), 7.55 (m, 5H), 7.77 (m, 3H), 7.99 (m, 5H), 8.09 (d, 1H), 8.19 ( d, 1 H), 11.66 (s, 1 H)
[[
준비예Preparation
16] A-16의 합성 16] Synthesis of A-16
<<
단계1Step 1
> A-16의 합성> Synthesis of A-16
준비예 1의 <단계 1>에서 사용된 3-브로모-6-페닐-9H-카바졸 대신 3-브로모-9H-카바졸(2.46g, 10mmol)를 사용하고 [1,1'-바이페닐]-3-일보로닉 산 대신 (3-(트리페닐렌-2-일)페닐)보로닉 산(3.48g, 10mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 A-16를 얻었다.Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'-by <Step 1> of Preparation Example 1, except that (3- (triphenylen-2-yl) phenyl) boronic acid (3.48g, 10mmol) was used instead of phenyl] -3-ylboronic acid. The same procedure was followed to obtain A-16.
1H-NMR: δ 7.20 (t, 1H), 7.50 (m, 12H), 7.90 (m, 3H), 8.19 (d, 1H), 8.33 (d, 1H), 8.46 (m, 2H), 9.11 (d, 1H), 9.60 (d, 1H), 11.66 (s, 1H) 1 H-NMR: δ 7.20 (t, 1H), 7.50 (m, 12H), 7.90 (m, 3H), 8.19 (d, 1H), 8.33 (d, 1H), 8.46 (m, 2H), 9.11 ( d, 1H), 9.60 (d, 1H), 11.66 (s, 1H)
[[
합성예Synthesis Example
1] J-1의 합성 1] Synthesis of J-1
질소 기류 하에서 A-1 (3.95g, 10mmol), 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (3.88g, 10mmol), Pd(OAc)2 (0.22g, 1mmol), P(t-Bu)3 (0.47ml, 2mmol), NaO(t-Bu) (1.92g, 20mmol) 및 톨루엔(400ml)를 혼합하고 110℃ 에서 2시간 동안 교반하였다. 반응이 종결된 후 톨루엔을 농축하고, 고체염을 filter 한 뒤, 재결정으로 정제하여 목적 화합물인 J-1 (3.51 g, 수율 50%)을 얻었다.A-1 (3.95 g, 10 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10 mmol), Pd (OAc) 2 under nitrogen stream (0.22 g, 1 mmol), P ( t- Bu) 3 (0.47 ml, 2 mmol), NaO ( t -Bu) (1.92 g, 20 mmol) and toluene (400 ml) were mixed and stirred at 110 ° C. for 2 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound J-1 (3.51 g, yield 50%).
[Mass]: 702[Mass]: 702
[[
합성예Synthesis Example
2] J-2의 합성 2] Synthesis of J-2
A-1 대신 A-2 (3.95g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-([1,1'-바이페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진(4.64g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-2 (3.97 g, 수율 51%)를 얻었다.Use A-2 (3.95 g, 10.0 mmol) instead of A-1 and 2-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Synthesis Example 1 except using '-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine (4.64 g, 10.0 mmol) The same procedure as in the title compound J-2 (3.97 g, yield 51%) was obtained.
[Mass]: 778 [Mass]: 778
[[
합성예Synthesis Example
3] J-3의 합성 3] Synthesis of J-3
A-1 대신 A-3 (4.85g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(3'-브로모-[1,1'-바이페닐]-3-일)-4,6-디페닐-1,3,5-트리아진(4.64g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-3 (4.51 g, 수율 52%)를 얻었다.Use A-3 (4.85 g, 10.0 mmol) instead of A-1 and 2- (3'-bromine instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Synthesis Example 1 except that mother- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 10.0 mmol) was used The same procedure was followed to obtain the title compound J-3 (4.51 g, yield 52%).
[Mass]: 869.04 [Mass]: 869.04
[[
합성예Synthesis Example
4] J-4의 합성 4] Synthesis of J-4
A-1 대신 A-4 (5.01g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 4-([1,1'-바이페닐]-4-일)-6-(3-브로모페닐)-2-페닐피리미딘(4.63g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-4 (4.68 g, 수율 53%)를 얻었다.Use A-4 (5.01 g, 10.0 mmol) instead of A-1 and 4-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was carried out except that '-biphenyl] -4-yl) -6- (3-bromophenyl) -2-phenylpyrimidine (4.63 g, 10.0 mmol) was used. The compound J-4 (4.68 g, yield 53%) was obtained.
[Mass]: 884.11 [Mass]: 884.11
[[
합성예Synthesis Example
5] J-5의 합성 5] Synthesis of J-5
A-1 대신 A-5 (5.85g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4,6-비스(3,5-디메틸페닐)-1,3,5-트리아진(3.68g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-5 (4.71 g, 수율 54%)를 얻었다.Use A-5 (5.85 g, 10.0 mmol) instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using 6-bis (3,5-dimethylphenyl) -1,3,5-triazine (3.68g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to the target compound J-5 ( 4.71 g, yield 54%) was obtained.
[Mass]: 873.12 [Mass]: 873.12
[[
합성예Synthesis Example
6] J-6의 합성 6] Synthesis of J-6
A-1 대신 A-6 (5.45g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(4-브로모페닐)-4,6-디페닐-1,3,5-트리아진(3.88g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-6 (4.69 g, 수율 55%)를 얻었다.Use A-6 (5.45 g, 10.0 mmol) instead of A-1 and 2- (4-bromo instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using phenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to provide the target compound J-6 (4.69 g , Yield 55%) was obtained.
[Mass]: 853.04 [Mass]: 853.04
[[
합성예Synthesis Example
7] J-7의 합성 7] Synthesis of J-7
A-1 대신 A-7 (7.09g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 4'-(4-브로모페닐)-4,4''-디-tert-부틸-2,2':6',2''-터피리딘(5.00g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-7 (6.32 g, 수율 56%)를 얻었다.Use A-7 (7.09 g, 10.0 mmol) instead of A-1 and replace 4 '-(4-bromine with 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Morphenyl) -4,4 ''-di-tert-butyl-2,2 ': 6', 2 ''-terpyridine (5.00 g, 10.0 mmol) was used in the same procedure as in Synthesis Example 1 Was carried out to obtain the title compound J-7 (6.32 g, yield 56%).
[Mass]: 1129.46 [Mass]: 1129.46
[[
합성예Synthesis Example
8] J-8의 합성 8] Synthesis of J-8
A-1 대신 A-8 (7.01g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 5-브로모아이소프탈로니트릴(2.07g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-8 (4.71 g, 수율 57%)를 얻었다.Use A-8 (7.01 g, 10.0 mmol) instead of A-1 and 5-bromoisophthalonitrile instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using (2.07g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-8 (4.71 g, yield 57%).
[Mass]: 828.06 [Mass]: 828.06
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합성예Synthesis Example
9] J-9의 합성 9] Synthesis of J-9
A-1 대신 A-9 (7.01 g, 10.0 mmol) 를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4,6-비스(4-(트리플루오루메틸)페닐)-1,3,5-트리아진(4.48g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-9 (6.20 g, 수율 58%)를 얻었다.Use A-9 (7.01 g, 10.0 mmol) instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-bis (4- (trifluororumethyl) phenyl) -1,3,5-triazine (4.48g, 10.0mmol) the same procedure as in Synthesis Example 1 was carried out to give the target compound J -9 (6.20 g, yield 58%) was obtained.
[Mass]: 1069.13 [Mass]: 1069.13
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합성예Synthesis Example
10] J-10의 합성 10] Synthesis of J-10
A-1 대신 A-10 (8.44g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 5,5'-(6-(3-브로모페닐)-1,3,5-트리아진-2,4-디일)디퀴놀린 (4.90 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-10 (7.39 g, 수율 59%)를 얻었다.Use A-10 (8.44 g, 10.0 mmol) instead of A-1 and 5,5 '-(6 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was carried out except that-(3-bromophenyl) -1,3,5-triazine-2,4-diyl) diquinoline (4.90 g, 10.0 mmol) was used. The compound J-10 (7.39 g, yield 59%) was obtained.
[Mass]: 1253.53 [Mass]: 1253.53
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합성예Synthesis Example
11] J-11의 합성 11] Synthesis of J-11
1 대신 A-11 (5.73g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 4-브로모-2-플루오루디벤조[b,d]퓨란(2.65g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-11 (4.54 g, 수율 60%)를 얻었다.Use A-11 (5.73 g, 10.0 mmol) instead of 1 and 4-bromo-2-fluororudy instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using benzo [b, d] furan (2.65g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-11 (4.54 g, yield 60%).
[Mass]: 757.87 [Mass]: 757.87
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합성예Synthesis Example
12] J-12의 합성 12] Synthesis of J-12
A-1 대신 A-12 (5.69g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 (4-브로모페닐)디페닐 포스핀 옥사이드(3.57g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-12 (4.99 g, 수율 59%)를 얻었다.Use A-12 (5.69 g, 10.0 mmol) instead of A-1 and (4-bromophenyl) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using diphenyl phosphine oxide (3.57g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-12 (4.99 g, 59% yield).
[Mass]: 846.01 [Mass]: 846.01
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합성예Synthesis Example
13] J-13의 합성 13] Synthesis of J-13
A-1 대신 A-13 (4.25g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-([1,1'-바이페닐]-4-일)-4-(4-브로모페닐)-6-(4-플루오루페닐)피리딘(4.81g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-13 (4.79 g, 수율 58%)를 얻었다.Use A-13 (4.25 g, 10.0 mmol) instead of A-1 and 2-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Same as Synthesis Example 1 except using '-biphenyl] -4-yl) -4- (4-bromophenyl) -6- (4-fluoroluphenyl) pyridine (4.81 g, 10.0 mmol) The procedure was carried out to obtain the title compound J-13 (4.79 g, yield 58%).
[Mass]: 826.01 [Mass]: 826.01
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합성예Synthesis Example
14] J-14의 합성 14] Synthesis of J-14
A-1 대신 A-14 (4.25g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4-페닐퀴나졸린 (2.85g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-14 (3.49 g, 수율 57%)를 얻었다.Use A-14 (4.25 g, 10.0 mmol) instead of A-1 and 2-bromo-4- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using phenylquinazoline (2.85g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-14 (3.49 g, yield 57%).
[Mass]: 613.72[Mass]: 613.72
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합성예Synthesis Example
15] J-15의 합성 15] Synthesis of J-15
A-1 대신 A-15 (4.35 g, 10.0 mmol) 를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4-(4-(나프탈렌-1-일)페닐)퀴나졸린(4.11g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-15 (4.28 g, 수율 56%)를 얻었다.Use A-15 (4.35 g, 10.0 mmol) instead of A-1 and 2-bromo-4- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using (4- (naphthalen-1-yl) phenyl) quinazolin (4.11g, 10.0mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-15 (4.28 g, yield 56% )
[Mass]: 765.96[Mass]: 765.96
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합성예Synthesis Example
16] J-16의 합성 16] Synthesis of J-16
A-1 대신 A-16 (4.69g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4,6-디페닐-1,3,5-트리아진(3.12g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-16 (3.85 g, 수율 55%)를 얻었다.Use A-16 (4.69 g, 10.0 mmol) instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using 6-diphenyl-1,3,5-triazine (3.12g, 10.0mmol) was carried out the same process as in Synthesis Example 1 to the target compound J-16 (3.85 g, 55% yield) Got.
[Mass]: 700.85[Mass]: 700.85
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합성예Synthesis Example
17] J-17의 합성 17] Synthesis of J-17
A-1 대신 3-페닐-9H-카바졸(2.43g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(3'-브로모-[1,1'-바이페닐]-3-일)-4,6-디페닐-1,3,5-트리아진 (4.64 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-17 (3.38 g, 수율 54%)를 얻었다.3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- Except using (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 10.0 mmol) Was carried out in the same manner as in Synthesis Example 1 to obtain J-17 (3.38 g, yield 54%) as a target compound.
[Mass]: 626.76[Mass]: 626.76
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합성예Synthesis Example
18] J-18의 합성 18] Synthesis of J-18
A-1 대신 3-페닐-9H-카바졸(2.43g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(3''-브로모-[1,1':3',1''-터페닐]-3-일)-4,6-디페닐-1,3,5-트리아진(5.40g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-18 (3.72 g, 수율 53%)를 얻었다.3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3 ''-bromo- [1,1 ': 3', 1 ''-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (5.40 g, 10.0 Except for using mmol), the same procedure as in Synthesis Example 1 was performed to obtain J-18 (3.72 g, yield 53%) as a target compound.
[Mass]: 702.86[Mass]: 702.86
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합성예Synthesis Example
19] J-19의 합성 19] Synthesis of J-19
A-1 대신 3-페닐-9H-카바졸(2.43g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 4-([1,1'-바이페닐]-4-일)-6-(3'-브로모-[1,1'-바이페닐]-3-일)-2-페닐피리미딘(5.39g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-19 (3.64 g, 수율 52%)를 얻었다.3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1, 4- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ([1,1'-biphenyl] -4-yl) -6- (3'-bromo- [1,1'-biphenyl] -3-yl) -2-phenylpyrimidine (5.39 g, 10.0 Except for using mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-19 (3.64 g, yield 52%).
[Mass]: 701.87[Mass]: 701.87
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합성예Synthesis Example
20] J-20의 합성 20] Synthesis of J-20
A-1 대신 3-([1,1'-바이페닐]-3-일)-9H-카바졸(3.19g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(4''-브로모-[1,1':3',1''-터페닐]-4-일)-4,6-디페닐-1,3,5-트리아진(5.40g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-20 (3.97 g, 수율 51%)를 얻었다.3-([1,1'-biphenyl] -3-yl) -9H-carbazole (3.19 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6- 2- (4 ''-bromo- [1,1 ': 3', 1 ''-terphenyl] -4-yl) -4,6-diphenyl instead of diphenyl-1,3,5-triazine Except for using -1,3,5-triazine (5.40g, 10.0mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-20 (3.97 g, yield 51%).
[Mass]: 778.96[Mass]: 778.96
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합성예Synthesis Example
21] J-21의 합성 21] Synthesis of J-21
A-1 대신 3-([1,1'-바이페닐]-4-일)-9H-카바졸(3.19g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모-4-페닐퀴나졸린 (2.85g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-21 (2.61 g, 수율 50%)를 얻었다.3-([1,1'-biphenyl] -4-yl) -9H-carbazole (3.19 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6- Except for using 2-bromo-4-phenylquinazoline (2.85g, 10.0mmol) instead of diphenyl-1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to give the target compound J- 21 (2.61 g, yield 50%) was obtained.
[Mass]: 523.64[Mass]: 523.64
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합성예Synthesis Example
22] H-3의 합성 22] Synthesis of H-3
A-1 대신 9H,9'H-3,3'-바이카바졸(3.32g, 10.0mmol)을 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 1-브로모-3-메틸벤젠(3.42g, 20.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-3 (2.51 g, 수율 49%)를 얻었다.9H, 9'H-3,3'-bicarbazole (3.32 g, 10.0 mmol) instead of A-1, 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 Except for using 1-bromo-3-methylbenzene (3.42g, 20.0mmol) instead of triazine was carried out the same procedure as in Synthesis Example 1 H-3 (2.51 g, yield 49%) of the target compound Got.
[Mass]: 512.66[Mass]: 512.66
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합성예Synthesis Example
23] H-21의 합성 23] Synthesis of H-21
A-1 대신 9-페닐-9H,9'H-3,3'-바이카바졸(4.08g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-다이페닐-1,3,5-트라이진 대신 2-브로모트리페닐렌(3.07g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-21 (3.04 g, 수율 48%)를 얻었다.9-phenyl-9H, 9'H-3,3'-bicarbazole (4.08 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1 Except for using 2-bromotriphenylene (3.07g, 10.0mmol) instead of, 3,5-triazine was subjected to the same process as in Synthesis Example 1 H-21 (3.04 g, yield 48) %) Was obtained.
[Mass]: 634.78[Mass]: 634.78
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합성예Synthesis Example
24] H-27의 합성 24] Synthesis of H-27
A-1 대신 9-페닐-9H,9'H-3,3'-바이카바졸(4.08g, 10.0mmol) 를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-브로모디벤조[b,d]퓨란(2.47g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-27 (2.70 g, 수율 47%)를 얻었다.9-phenyl-9H, 9'H-3,3'-bicarbazole (4.08 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1 Except for using 2-bromodibenzo [b, d] furan (2.47g, 10.0mmol) instead of 3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to give the target compound H-27 (2.70). g, yield 47%).
[Mass]: 574.68[Mass]: 574.68
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합성예Synthesis Example
25] H-62의 합성 25] Synthesis of H-62
A-1 대신 9-페닐-9H,9'H-3,3'-바이카바졸(4.08g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 1-플루오로-4-아이도벤젠 (2.22g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-62 (2.31 g, 수율 46%)를 얻었다.9-phenyl-9H, 9'H-3,3'-bicarbazole (4.08 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1 Except for using 1-fluoro-4-idodobenzene (2.22g, 10.0mmol) instead of, 3,5-triazine was subjected to the same procedure as in Synthesis Example 1 H-62 (2.31 g) , Yield 46%) was obtained.
[Mass]: 502.59[Mass]: 502.59
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합성예Synthesis Example
26] H-66의 합성 26] Synthesis of H-66
질소 기류 하에서 (9,9'-디페닐-9H,9'H-[3,3'-바이카바졸]-6-일)보로닉 산 (5.28g, 10mmol), 4-브로모디벤조[b,d]퓨란(2.47g, 10mmol), K2CO3 (2.76g, 20mmol), Pd(PPh3)4(0.58g, 0.5mmol) 및 THF(60 mL)과 정제수(15ml)을 혼합하고 110℃ 에서 12시간 동안 교반하였다. 상온으로 식힌 후 H2O를 첨가하고 brine을 이용하여 추출하였다. MgSO4로 수분을 제거한 후 유기층을 농축한 후 컬럼크로마토그래피를 실시하여 목적 화합물인 H-66 (2.92 g, 45%)를 얻었다. (9,9'-diphenyl-9H, 9'H- [3,3'-bicarbazol] -6-yl) boronic acid (5.28 g, 10 mmol), 4-bromodibenzo [b under nitrogen stream , d] furan (2.47g, 10mmol), K 2 CO 3 (2.76g, 20mmol), Pd (PPh 3 ) 4 (0.58g, 0.5mmol) and THF (60 mL) and purified water (15ml) Stir at 12 ° C. for 12 h. After cooling to room temperature, H 2 O was added and extracted using brine. Water was removed with MgSO 4 , the organic layer was concentrated and column chromatography was performed to obtain H-66 (2.92 g, 45%) as a target compound.
[Mass]: 650.78 [Mass]: 650.78
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합성예Synthesis Example
27] H-120의 합성 27] Synthesis of H-120
(9,9'-디페닐-9H,9'H-[3,3'-바이카바졸]-6-일)보로닉 산 대신 (7-페닐-7H-벤조[c]카바졸-10-일)보로닉 산(3.37g, 10.0mmol)를 사용하고 4-브로모디벤조[b,d]퓨란 대신 10-브로모-7-페닐-7H-벤조[c]카바졸(3.72g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 26과 동일한 과정을 수행하여 목적 화합물인 H-120 (2.57 g, 수율 44%)를 얻었다.(7-phenyl-7H-benzo [c] carbazole-10- instead of (9,9'-diphenyl-9H, 9'H- [3,3'-bicarbazol] -6-yl) boronic acid I) 10-bromo-7-phenyl-7H-benzo [c] carbazole (3.72 g, 10.0 mmol) using boronic acid (3.37 g, 10.0 mmol) instead of 4-bromodibenzo [b, d] furan Except for using), the same procedure as in Synthesis Example 26 was carried out to obtain the target compound H-120 (2.57 g, yield 44%).
[Mass]: 584.72[Mass]: 584.72
[[
합성예Synthesis Example
28] H-129의 합성 28] Synthesis of H-129
A-1 대신 9-([1,1'-바이페닐]-3-일)-9H,9'H-3,3'-바이카바졸(4.84g, 10.0mmol)를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 3'-브로모-[1,1'-바이페닐]-3-카보니트릴 (2.58g, 10.0mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-129 (2.84 g, 수율 43%)를 얻었다.Use 9-([1,1'-biphenyl] -3-yl) -9H, 9'H-3,3'-bicarbazole (4.84 g, 10.0 mmol) instead of A-1 and 2- (3 -Bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 3'-bromo- [1,1'-biphenyl] -3-carbonitrile (2.58 g, 10.0 mmol) Except for using the same procedure as in Synthesis Example 1 to obtain the target compound H-129 (2.84 g, 43% yield).
[Mass]: 661.81[Mass]: 661.81
[[
합성예Synthesis Example
29] H-139의 합성 29] Synthesis of H-139
A-1 대신 9H,9'H-2,3'-바이카바졸 (3.32g, 10.0mmol) 를 사용하고 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 3-브로모-1,1'-바이페닐 (4.66 g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 H-139 (2.80 g, 수율 44%)를 얻었다.9H, 9'H-2,3'-bicarbazole (3.32 g, 10.0 mmol) instead of A-1, 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 Except for using 3-bromo-1,1'-biphenyl (4.66 g, 20.0 mmol) instead of triazine was carried out the same procedure as in Synthesis Example 1 H-139 (2.80 g, yield) 44%).
[Mass]: 636.80[Mass]: 636.80
[[
실시예Example
1~9] 유기 EL 소자의 제조 1 ~ 9] Fabrication of Organic EL Device
ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having 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, H-27을 제 1호스트로, 하기 J-97을 각각 제 2호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 10 % 제 1 호스트 + 90 % 제 2 호스트 + 10 % PD-1(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, m-MTDATA (60 nm) / TCTA (80 nm) / 10% first host using H-27 as the first host and J-97 as the second host, respectively An organic EL device was fabricated by stacking + 90% second host + 10% PD-1 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
사용된 m-MTDATA, TCTA, PD-1, BCP 의 구조는 하기와 같다.The structure of m-MTDATA, TCTA, PD-1, BCP used is as follows.
하기 표 1과 같이 제 1 호스트 및 제 2 호스트의 사용 비율을 조정하여 유기 EL 소자를 제작하였다. 실시예 1 내지 9 에서 각각 제조된 유기 EL 소자에 대하여, 전류밀도 10mA/㎠ 에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.As shown in Table 1 below, the use ratio of the first host and the second host was adjusted to produce an organic EL device. For organic EL devices manufactured in Examples 1 to 9, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.
| 샘플Sample | 호스트Host | 구동 전압Driving voltage | 전류효율Current efficiency | 수명 T95 Life span T 95 |
| (V)(V) | (cd/A)(cd / A) | (hrs)(hrs) | ||
| 실시예 1Example 1 | 10% H-27 + 90% J-9710% H-27 + 90% J-97 | 5.535.53 | 44.544.5 | 140140 |
| 실시예 2Example 2 | 20% H-27 + 80% J-9720% H-27 + 80% J-97 | 5.625.62 | 45.145.1 | 150150 |
| 실시예 3Example 3 | 30% H-27 + 70% J-9730% H-27 + 70% J-97 | 5.595.59 | 45.545.5 | 160160 |
| 실시예 4Example 4 | 40% H-27 + 60% J-9740% H-27 + 60% J-97 | 5.65.6 | 43.743.7 | 175175 |
| 실시예 5Example 5 | 50% H-27 + 50% J-9750% H-27 + 50% J-97 | 5.495.49 | 43.243.2 | 200200 |
| 실시예 6Example 6 | 60% H-27 + 40% J-9760% H-27 + 40% J-97 | 5.355.35 | 43.543.5 | 180180 |
| 실시예 7Example 7 | 70% H-27 + 30% J-9770% H-27 + 30% J-97 | 5.395.39 | 42.842.8 | 165165 |
| 실시예 8Example 8 | 80% H-27 + 20% J-9780% H-27 + 20% J-97 | 5.335.33 | 42.242.2 | 155155 |
| 실시예 9Example 9 | 90% H-27 + 10% J-9790% H-27 + 10% J-97 | 5.355.35 | 42.342.3 | 145145 |
[[
실시예Example
10~17] 유기 EL 소자의 제조 10 ~ 17] Fabrication of Organic EL Device
실시예 1과 같이 준비된 ITO 투명 전극 위에, 하기 H-27을 제 1호스트로, 표 2의화합물을 제 2호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 50 % 제 1 호스트 + 50 % 제 2 호스트 + 10 % PD-1(300nm) / BCP(10nm) / Alq3(30 nm) / LiF(1 nm) / Al(200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다.On the ITO transparent electrode prepared as in Example 1, m-MTDATA (60 nm) / TCTA (80 nm) / 50% was prepared using the following H-27 as the first host and the compound of Table 2 as the second host. An organic EL device was fabricated by stacking 1 host + 50% second host + 10% PD-1 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order. .
실시예 10~17 에서 각각 제조된 유기 EL 소자에 대하여, 전류밀도 10mA/㎠에서의 구동전압, 전류효율 및 발광피크를 측정하였고, 그 결과를 하기 표 2에 나타내었다.For the organic EL devices manufactured in Examples 10 to 17, the driving voltage, the current efficiency, and the light emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
| 샘플Sample | 호스트Host | 구동 전압Driving voltage | 전류효율Current efficiency | 수명 T95 Life span T 95 |
| (V)(V) | (cd/A)(cd / A) | (hrs)(hrs) | ||
| 실시예 10Example 10 | 50% H-27 + 50% J-9750% H-27 + 50% J-97 | 5.495.49 | 43.243.2 | 200200 |
| 실시예 11Example 11 | 50% H-27 + 50% J-9850% H-27 + 50% J-98 | 5.455.45 | 43.143.1 | 180180 |
| 실시예 12Example 12 | 50% H-27 + 50% J-10250% H-27 + 50% J-102 | 5.595.59 | 43.343.3 | 155155 |
| 실시예 13Example 13 | 50% H-27 + 50% J-10650% H-27 + 50% J-106 | 5.355.35 | 43.543.5 | 160160 |
| 실시예 14Example 14 | 50% H-27 + 50% J-11050% H-27 + 50% J-110 | 5.495.49 | 43.243.2 | 150150 |
| 실시예 15Example 15 | 50% H-27 + 50% J-11450% H-27 + 50% J-114 | 5.355.35 | 42.542.5 | 140140 |
| 실시예 16Example 16 | 50% H-27 + 50% J-11850% H-27 + 50% J-118 | 5.525.52 | 44.244.2 | 165165 |
| 실시예 17Example 17 | 50% H-27 + 50% J-12250% H-27 + 50% J-122 | 5.445.44 | 43.643.6 | 170170 |
[[
비교예Comparative example
1] 유기 EL 소자의 제조 1] Fabrication of Organic EL Device
실시예 1 에서 발광층 형성시 호스트 물질로서 하기 CBP를 100% 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 유기 EL 소자를 제작하였다.An organic EL device was manufactured in the same manner as in Example 1, except that 100% of the following CBP was used as a host material in forming the emission layer in Example 1.
[비교예 2] 유기 EL 소자의 제조Comparative Example 2 Fabrication of Organic EL Device
실시예 1 에서 발광층 형성시 호스트 물질로서 J-97을 100% 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 유기 EL 소자를 제작하였다.An organic EL device was manufactured in the same manner as in Example 1, except that 100% of J-97 was used as a host material in forming the emission layer in Example 1.
전술한 비교예 1~2에서 각각 제조된 유기 EL 소자에 대하여, 전류밀도 10mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 3에 나타내었다.For organic EL devices manufactured in Comparative Examples 1 and 2, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.
| 샘플Sample | 호스트Host | 구동 전압Driving voltage | 전류효율Current efficiency | 수명 T95 Life span T 95 |
| (V)(V) | (cd/A)(cd / A) | (hrs)(hrs) | ||
| 비교예 1Comparative Example 1 | 100% CBP100% CBP | 6.936.93 | 38.238.2 | 100100 |
| 비교예 2Comparative Example 2 | 100% J-97100% J-97 | 6.596.59 | 41.141.1 | 115115 |
상기 표 1 내지 3을 살펴보면, 본 발명의 화학식 6로 표시되는 화합물을 발광층의 제 1호스트 물질로 사용하는 실시예 1~17의 유기 EL 소자는 종래 CBP 또는 J-97을 단독 호스트 물질로 사용하는 비교예 1~2의 유기 EL 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.Referring to Tables 1 to 3, the organic EL device of Examples 1 to 17 using the compound represented by Chemical Formula 6 of the present invention as the first host material of the light emitting layer uses CBP or J-97 as the sole host material. It was confirmed that the organic EL devices of Comparative Examples 1 and 2 exhibited superior performance in terms of current efficiency and driving voltage.
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 열적 안정성 및 인광 특성 등이 우수한 신규한 카바졸계 화합물 및 이를 하나 이상의 유기물층에 포함하여 낮은 구동 전압과 높은 발광 효율 및 향상된 수명 특성을 갖는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission. An organic electroluminescent device having efficiency and improved lifespan characteristics.
Claims (13)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,L1 내지 L4는 서로 동일하거나 상이하고 각각 독립적으로 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며,L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,Ar1은 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기이며;Ar 1 is C 6 ~ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;Ar2 및 Ar3은 서로 상이하고, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되고,Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ~ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,n 및 m는 각각 독립적으로 0 내지 3의 정수이고,n and m are each independently an integer of 0 to 3,R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되고; R 1 and R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group , C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine group , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, Ar1 내지 Ar3의 아릴기 및 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, a 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 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C substituted with at least 60 group consisting arylsilyl the selected one more substituents or being unsubstituted, a plurality of substituents When substituted with, they may be the same or different from each other. - 제 1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 2로 표시되는 화합물:Formula 1 is a compound represented by the following formula (2):[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,L1 내지 L4, Ar1 내지 Ar3, n, m, R1 및 R2 각각은 제1항에서 정의된 바와 같다.L 1 to L 4 , Ar 1 to Ar 3 , n, m, R 1 and R 2 are each as defined in claim 1. - 제 1항에 있어서,The method of claim 1,상기 Ar1은 하기 화학식 3 내지 8의 치환기로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물:Ar 1 is a compound characterized in that it is selected from the group consisting of substituents of the following Chemical Formulas 3 to 8:[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
상기 화학식 3 내지 화학식 8에서,In Chemical Formulas 3 to 8,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;a 및 b는 각각 독립적으로 0 내지 4의 정수이고;a and b are each independently an integer of 0 to 4;X1 내지 X5 및 X7 내지 X12는 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 5 and X 7 to X 12 are each independently N or C (R 3 );X6은 O 또는 S이며;X 6 is O or S;R3 내지 R5는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,R 3 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an alkyl of C 1 ~ C 40 Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ mono or diaryl phosphine of C 60 blood group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ the group consisting of an aryl amine of the C 60 May be selected from or combined with adjacent groups to form a condensed ring,상기 R3 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, 할로겐C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 3 to R 5 Boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, halogen C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ mono or diaryl phosphine blood group of C 60, C 6 ~ C When substituted or unsubstituted with one or more substituents selected from the group consisting of 60 arylphosphine oxide groups and C 6 -C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other. - 제 1항에 있어서,The method of claim 1,상기 Ar2 및 Ar3은 아래의 치환기로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물:Ar 2 and Ar 3 is a compound, characterized in that selected from the group consisting of:
상기 화학식 A-1 내지 A-24에서,In Chemical Formulas A-1 to A-24,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R6)이며;Z 1 to Z 5 are the same as or different from each other, and are each independently N or C (R 6 );Y1 및 Y2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합, C(R7)(R8), N(R9), O 및 S로 이루어진 군에서 선택되나, Y1 및 Y2 모두 단일결합은 아니며;Y 1 and Y 2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, C (R 7 ) (R 8 ), N (R 9 ), O and S, but both Y 1 and Y 2 Not a single bond;c는 0 내지 3의 정수이며; c is an integer from 0 to 3;d 및 e는 각각 독립적으로 0 내지 4의 정수이며;d and e are each independently an integer of 0 to 4;f는 0 내지 2의 정수이며;f is an integer from 0 to 2;R6 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 중수소, 할로겐, 시아노기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, R 6 to R 12 are the same as or different from each other, and are each independently selected from a group consisting of deuterium, a halogen, a cyano group, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, or are bonded to an adjacent group To form a condensed ring,상기 R6내지 R12의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The aryl group and heteroaryl group of R 6 to R 12 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alky Neyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 arylamine aryl boron group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 of Unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, When substituted with a plurality of substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 아래의 화합물로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물: Compound represented by Formula 1 is selected from the group consisting of the following compounds:
- 제1항에 따른 화학식 1로 표시되는 화합물 및 하기 화학식 9로 표시되는 화합물을 포함하는 유기 전계 발광 소자용 조성물:An organic electroluminescent device composition comprising a compound represented by Formula 1 according to claim 1 and a compound represented by Formula 9 below:[화학식 9] [Formula 9]
여기서,here,g 및 j는 각각 독립적으로 0 내지 4의 정수이고;g and j are each independently an integer from 0 to 4;h 및 i는 각각 독립적으로 0 내지 3의 정수이고;h and i are each independently an integer from 0 to 3;Ar4 및 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 40개의 헤테로아릴기이며;Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;R13 내지 R16은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C40의 알킬포스핀기, C1~C40의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택되며, Of R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of each other Alkynyl group, C 6 ~ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ~ C 40 alkyl phosphine group, C 1 ~ alkyl Phosphinicosuccinic group of C 40, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine blood group, C 6 of ~ C 60 aryl phosphine oxide is selected from the pin group and a C 6 ~ C 60 aryl silyl group of the group consisting of,상기 Ar4, Ar5 및 R13 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, 할로겐C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 모노 또는 디아릴포스피닐기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴실릴기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.Ar 4 , Ar 5, and R 13 to R 16 alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkyloxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl groups , Alkyl boron group, aryl boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group , Halogen 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 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 Aryloxy group of -C 60 , C 1 -C 40 alkyloxy group, arylamine group of C 6 -C 60 , cycloalkyl group of C 3 -C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine of When substituted or unsubstituted with one or more substituents selected from the group consisting of a pinyl group, a C 6 -C 60 arylphosphine oxide group and a C 6 -C 60 arylsilyl group, they are the same as each other. Or may be different and combine with adjacent groups to form a condensed ring. - 제 6항에 있어서,The method of claim 6,상기 화학식 9은 하기 화학식 10 내지 화학식 13으로 표시되는 화합물:Formula 9 is a compound represented by Formula 10 to Formula 13:[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
상기 화학식 10 내지 화학식 13에서,In Chemical Formulas 10 to 13,Ar4 및 Ar5, g, h, i, j, R13 내지 R16 각각은 제9항에서 정의된 바와 동일하다.Ar 4 and Ar 5 , g, h, i, j, R 13 to R 16 are each as defined in claim 9. - 제6항에 있어서, The method of claim 6,상기 Ar4 및 Ar5는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 40개의 헤테로아릴기인 것을 특징으로 하는 화합물. Ar 4 And Ar 5 is the same as or different from each other, and each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups.
- 제6항에 있어서,The method of claim 6,상기 화학식 9로 표시되는 화합물은 아래의 화합물로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물: Compound represented by Formula 9 is selected from the group consisting of the following compounds:
- (i) 양극, (ii) 음극 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,(i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중 적어도 하나는 제1항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자.At least one of the one or more organic material layers comprises the compound of claim 1 characterized in that the organic electroluminescent device.
- 제10항에 있어서, The method of claim 10,상기 화합물을 포함하는 유기물층은 발광층, 발광 보조층, 정공 수송층, 정공 주입층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되며,The organic material layer including the compound is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transport layer, a hole injection layer, an electron transport layer and an electron injection layer,상기 화합물은 하기 화학식 1 및 화학식 9로 표시되는 화합물이며, 상기 화학식 1로 표시되는 화합물 또는 화학식 9로 표시되는 화합물 중 각각 1종 이상 포함하는 것을 특징으로 하는 유기 전계 발광 소자:The compound is a compound represented by the following formula (1) and formula (9), the organic electroluminescent device comprising at least one of each of the compound represented by the formula (1) or the compound represented by the formula (9):[화학식 1][Formula 1]
[화학식 9][Formula 9]
상기 화학식 1 및 화학식 9에서,In Chemical Formula 1 and Chemical Formula 9,L1 내지 L4, Ar1 내지 Ar3, n, m, R1 및 R2 각각은 제1항에서 정의된 바와 동일하고;L 1 to L 4 , Ar 1 to Ar 3 , n, m, R 1 and R 2 are each as defined in claim 1;Ar4 및 Ar5, g, h, i, j, R13 내지 R16 각각은 제9항에서 정의된 바와 동일하다.Ar 4 and Ar 5 , g, h, i, j, R 13 to R 16 are each as defined in claim 9. - 제11항에 있어서,The method of claim 11,상기 화학식 1 및 화학식 9로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 특징인 유기 전계 발광 소자.The organic material layer comprising the compound represented by Formula 1 and Formula 9 is an emission layer, characterized in that the organic electroluminescent device.
- 제12항에 있어서,The method of claim 12,상기 화학식 1 및 화학식 9로 표시되는 화합물은 인광 호스트인 것을 특징으로 하는 유기 전계 발광 소자.The compound represented by Formula 1 and Formula 9 is a phosphorescent host, characterized in that the organic electroluminescent device.
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| US20180166634A1 (en) * | 2016-12-14 | 2018-06-14 | Samsung Electronics Co., Ltd. | Organic light-emitting device and compound |
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| Publication number | Publication date |
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| KR20170123955A (en) | 2017-11-09 |
| KR102577726B1 (en) | 2023-09-14 |
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