WO2017175987A1 - Organic compound and organic electroluminescence device comprising same - Google Patents
Organic compound and organic electroluminescence device comprising same Download PDFInfo
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- WO2017175987A1 WO2017175987A1 PCT/KR2017/002848 KR2017002848W WO2017175987A1 WO 2017175987 A1 WO2017175987 A1 WO 2017175987A1 KR 2017002848 W KR2017002848 W KR 2017002848W WO 2017175987 A1 WO2017175987 A1 WO 2017175987A1
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 8
- 238000005401 electroluminescence Methods 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 239000010410 layer Substances 0.000 claims abstract description 92
- 239000012044 organic layer Substances 0.000 claims abstract description 85
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 239000011368 organic material Substances 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- -1 alkyl boron Chemical compound 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 171
- 230000015572 biosynthetic process Effects 0.000 description 97
- 238000003786 synthesis reaction Methods 0.000 description 97
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 58
- 238000004440 column chromatography Methods 0.000 description 57
- 239000000463 material Substances 0.000 description 54
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 239000002904 solvent Substances 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 14
- YHAHNQXQOZYZLP-UHFFFAOYSA-N 10-bromo-7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C(C=3C(=CC=C(C=3)Br)N3)C3=CC=C21 YHAHNQXQOZYZLP-UHFFFAOYSA-N 0.000 description 13
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- NZZNLINNQZRBFU-UHFFFAOYSA-N ClC1=NC=2C=CC3=C(C=2C(=N1)C1=CC=CC=C1)C(C(=C3)C1=CC=CC=C1)(C)C Chemical compound ClC1=NC=2C=CC3=C(C=2C(=N1)C1=CC=CC=C1)C(C(=C3)C1=CC=CC=C1)(C)C NZZNLINNQZRBFU-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 0 C*(C1*=*)c2cc(cccc3)c3cc2*[C@]1*=*C Chemical compound C*(C1*=*)c2cc(cccc3)c3cc2*[C@]1*=*C 0.000 description 5
- ZPWUQMMOVIYBQE-UHFFFAOYSA-N ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)SC(=C3)C1=CC=CC=C1 Chemical compound ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)SC(=C3)C1=CC=CC=C1 ZPWUQMMOVIYBQE-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- BTAZMXXFCAMGGP-UHFFFAOYSA-N ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)N(C(=C3)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)N(C(=C3)C1=CC=CC=C1)C1=CC=CC=C1 BTAZMXXFCAMGGP-UHFFFAOYSA-N 0.000 description 3
- DMLPOJGSQJKPRG-UHFFFAOYSA-N ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)N=C(O3)C1=CC=CC=C1 Chemical compound ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=CC=C1)N=C(O3)C1=CC=CC=C1 DMLPOJGSQJKPRG-UHFFFAOYSA-N 0.000 description 3
- CLLGKXXZLBTPLH-UHFFFAOYSA-N ClC1=NC=2C=CC3=C(C=2C(=N1)C1=CC=CC=C1)C=C(S3)C1=CC=CC=C1 Chemical compound ClC1=NC=2C=CC3=C(C=2C(=N1)C1=CC=CC=C1)C=C(S3)C1=CC=CC=C1 CLLGKXXZLBTPLH-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- ODBFMBHLQWEVNN-UHFFFAOYSA-N 2-bromo-5H-benzo[b]carbazole Chemical compound BrC=1C=C2C=3C=C4C(=CC=3NC2=CC=1)C=CC=C4 ODBFMBHLQWEVNN-UHFFFAOYSA-N 0.000 description 2
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- YVZDPJWTFNGPCA-UHFFFAOYSA-N BrC1=CC=2C=3C4=C(C=CC=3N(C=2C=C1)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1)C=CC=C4 Chemical compound BrC1=CC=2C=3C4=C(C=CC=3N(C=2C=C1)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1)C=CC=C4 YVZDPJWTFNGPCA-UHFFFAOYSA-N 0.000 description 2
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- ATLDVUFYDLNUJU-UHFFFAOYSA-N ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1)SC(=C3)C1=CC=CC=C1 Chemical compound ClC1=NC2=CC=C3C(=C2C(=N1)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1)SC(=C3)C1=CC=CC=C1 ATLDVUFYDLNUJU-UHFFFAOYSA-N 0.000 description 2
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- NHNCOYOZJQBGGE-UHFFFAOYSA-N ClC1=NC2=CC=C3C(=C2C(=N1)C=1C=CC=2N(C4=CC=CC=C4C=2C=1)C1=CC=CC=C1)SC(=C3)C1=CC=CC=C1 Chemical compound ClC1=NC2=CC=C3C(=C2C(=N1)C=1C=CC=2N(C4=CC=CC=C4C=2C=1)C1=CC=CC=C1)SC(=C3)C1=CC=CC=C1 NHNCOYOZJQBGGE-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000005647 linker 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
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HDDASYSQPSFSLH-UHFFFAOYSA-N (6-borono-9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=C(B(O)O)C=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 HDDASYSQPSFSLH-UHFFFAOYSA-N 0.000 description 1
- LUVUGOUOAXADNE-UHFFFAOYSA-N (7-borono-9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC(B(O)O)=CC=C3C2=C1 LUVUGOUOAXADNE-UHFFFAOYSA-N 0.000 description 1
- CEWPWFRPXWOOCS-UHFFFAOYSA-N (7-phenylbenzo[c]carbazol-10-yl)boronic acid Chemical compound C12=CC=C3C=CC=CC3=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 CEWPWFRPXWOOCS-UHFFFAOYSA-N 0.000 description 1
- AYLPNKHVFZUMJF-UHFFFAOYSA-N (9,9-dimethyl-10-phenylacridin-2-yl)boronic acid Chemical compound C12=CC=C(B(O)O)C=C2C(C)(C)C2=CC=CC=C2N1C1=CC=CC=C1 AYLPNKHVFZUMJF-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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- FQQREHKSHAYSMG-UHFFFAOYSA-N 1,2-dimethylacridine Chemical group C1=CC=CC2=CC3=C(C)C(C)=CC=C3N=C21 FQQREHKSHAYSMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FPJCNJSYOWFWLR-UHFFFAOYSA-N 1,4-dioxin-2-ylboronic acid Chemical compound OB(O)C1=COC=CO1 FPJCNJSYOWFWLR-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
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-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
- 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
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- GCSOJZMPHLRBMJ-UHFFFAOYSA-N thianthren-2-ylboronic acid Chemical compound C1=CC=C2SC3=CC(B(O)O)=CC=C3SC2=C1 GCSOJZMPHLRBMJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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Definitions
- the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, a novel organic compound having excellent hole transporting ability, electron transporting ability, light emitting ability, etc. and the compound as a material of an organic material layer, and thus luminous efficiency.
- the present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.
- the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
- the material included in the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.
- the light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
- a host / dopant system may be used as a light emitting material to increase luminous efficiency through an 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.
- anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
- a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 and (acac) Ir (btp) 2 are known, and as phosphorescent host materials, 4,4- dicarbazolybiphenyl (CBP) is known.
- the existing materials have a low glass transition temperature and poor thermal stability, and thus are not satisfactory in terms of lifespan in the organic EL device, and still need improvement in terms of light emission characteristics.
- An object of the present invention is to provide a novel organic compound that can be used as an organic material layer having excellent light emitting ability, hole transporting ability, hole injection ability and the like.
- Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
- the present invention provides a compound represented by the following formula (1).
- A is a 5-membered ring containing or not containing one or more atoms of N, O, S,
- B is a 6 membered aromatic ring
- Ar 1 is selected from the group consisting of hydrogen, a C 6 ⁇ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms,
- L 1 and L 2 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of a C 6 ⁇ C 60 arylene group and a heteroarylene group having 5 to 60 nuclear atoms, wherein L 1 is Connected to carbon or nitrogen of any one of X 1 , X 2 , Y 1 to Y 4 ,
- X 1 is NR 1 or CR 2 R 3 ,
- X 2 to X 4 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of S, O, NR 4 and CR 5 R 6 , wherein at least one of X 2 and X 4 is a single bond Except that X 3 and X 4 are both single bonds,
- Y 1 to Y 8 and Y 11 to Y 18 are each independently CR 7, wherein a plurality of R 7 are the same as or different from each other,
- R 1 to R 7 are the same as or different from each other, and are each independently selected from hydrogen, 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 (preferably , R 5 and other R 5 are bonded to form a condensed aromatic ring or a condensed heteroaromatic ring,
- the group and heteroaryl group are each independently deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ aryl of C 60 silyl group, C 2 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group,
- the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.
- the compound of the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, light emitting ability, etc., it can be used as an organic material layer material of the organic electroluminescent device, preferably a hole injection layer material, a hole transporting layer material or a light emitting layer material.
- the organic electroluminescent device including the compound of the present invention in the hole injection layer, the hole transport layer and / or the light emitting layer can be greatly improved aspects such as light emission performance, driving voltage, lifespan, efficiency, such organic electroluminescent device It can be effectively applied to a full color display panel and the like.
- the organic compound of the present invention is a 'moiety in which a quinazoline and a 5-membered ring (A) are bonded' or 'two substituents directly connected through a linker group (L 2 )' is directly connected or a linker group (L 1 )
- the substituent is a carbazole moiety, a dimethylfluorene moiety, a dibenzothiophene moiety, a dibenzofuran moiety, a dimethylacridine moiety, a thianthrene (thianthrene) moiety, dibenzodioxin moiety, spirofluorene and the like.
- the compound represented by Formula 1 of the present invention is that a quinazoline is bonded to a 5-membered ring (A) such as cyclopentane, furan, pyrazole, imidazole, oxazole, thiophene, etc. Because of the similar energy level, it can be adjusted higher than the energy level of the dopant, which can be applied as a host material, and has a triplet energy higher than that of the quinazoline-coupled structure. You can expect. In particular, the compound in which thiophene is bound to quinazoline may exhibit a longer wavelength than the compound in which the five-membered ring is bound to quinazoline. In addition, when an aryl group (for example, phenyl, biphenyl) is introduced into the 5-membered ring (A), the thermal stability is improved by blocking the reaction site.
- a aryl group for example, phenyl, biphenyl
- the compound of Formula 1 has a higher molecular weight and glass transition temperature than the compound in which one substituent is bonded to a 'moiety in which a quinazoline and a 5-membered ring are bonded', thereby providing excellent thermal stability.
- the compound of Formula 1 since the compound of Formula 1 has a narrow bandgap, the HOMO energy level and LUMO energy level suitable for the host material of the organic material layer have excellent carrier transport properties and luminescence properties.
- the carbazole moiety forms a condensed aromatic ring (benzocarbazole)
- it may have a narrower band gap, and the organic electroluminescent device including such a compound has a long lifespan. Can be improved.
- the compound represented by Chemical Formula 1 has a high electron-absorbing electron withdrawing group (EWG) such as a nitrogen-containing hetero ring (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since the whole molecule has a bipolar characteristic, it is possible to increase the binding force between the hole and the electron, and exhibit excellent carrier transport and luminescence properties.
- EWG electron-absorbing electron withdrawing group
- a nitrogen-containing hetero ring eg, pyridine group, pyrimidine group, triazine group, etc.
- Such a compound can be used not only as the light emitting layer material of the organic electroluminescent device, but also as the electron injection layer / transport layer material and the life improvement layer material.
- the compound of Formula 1 when the electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group is bonded to the basic skeleton, the hole injection and transport is smooth
- the compound having a large electron donor has high triplet energy, and thus, when used as a hole transporting material, an excellent efficiency increase may be expected due to the triple-triplet fusion effect.
- the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (red phosphorescent host material), an electron transport layer / injection layer material and a hole transport layer / injection layer material, light emitting auxiliary layer Material, life improvement layer material, more preferably, light emitting layer material, electron injection layer material, hole transport layer material.
- the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
- the compound represented by Formula 1 of the present invention may be embodied as a compound represented by any one of the following Formulas 2 to 5.
- A, B, Ar 1 , L 2 , X 1 to X 4 , Y 1 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
- the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 6 to 8.
- A, B, Ar 1 , L 2 , X 3 , X 4 , Y 5 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
- the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 9 to 11.
- A, B, Ar 1 , L 2 , X 1 , X 2 , Y 5 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
- (* Means a site which binds to L 1 of Formula 1) is preferably represented by any one of the substituents represented by the following A-1 to A-18.
- Ar 1 is as defined in Formula 1,
- R 8 is the same as or different from each other, and each independently selected from hydrogen, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,
- the aryl group of said R 8, heteroaryl groups each independently selected from deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of the, C 6 Aryl group of ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 ⁇ C 40 , aryloxy group of C 6 ⁇ C 60 , alkylsilyl group of C 1 ⁇ C 40 , C 6 An arylsilyl group of ⁇ C 60 , an alkyl boron group of C 2 ⁇ C 40, an aryl boron group of C 6 ⁇ C 60 , an arylphosphine group of C 6 ⁇ C 60 , an arylphosphine oxide group of C 6 ⁇ C 60 , and It may be substituted with one or more substituents selected from the group consisting of C 6 ⁇ C 60
- At this time, at least one of the plurality of R 6 is preferably an aryl group of C 6 ⁇ C 60 , more preferably phenyl.
- R 4 to R 6 are the same as defined in Chemical Formula 1.
- the compound represented by Chemical Formula 1 of the present invention described above may be embodied by the following compounds R1 to R635, but is not limited thereto.
- alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
- alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
- aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
- aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- 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.
- 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 alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
- Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
- the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
- the organic electroluminescent device of the present invention comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1).
- the compound may be used alone, or two or more may be used in combination.
- the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is a compound represented by Formula 1 It may include.
- the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.
- the emission layer may include a host material (preferably, a phosphorescent host material), in which case, the host material may include the compound of Formula 1 above.
- the light emitting layer of the organic EL device of the present invention may include a compound other than the compound of Formula 1 as a host.
- the structure of the organic EL device of the present invention is not particularly limited, but non-limiting examples include a substrate, an anode, a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer, an electron injection layer, and a cathode. It may be a stacked structure sequentially. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the hole transport layer, the electron transport layer, the light emitting layer is represented by the formula (1) It may include a compound represented.
- the structure of the organic EL device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.
- the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes a compound represented by the formula (1). have.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like can be used.
- the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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.
- a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene),
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A1 (5.6g, 12.1mmol, 72% yield).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A2 (8.5g, 11.8mmol, yield 70%).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A5 (9,7g, 12.7mmol, yield 75%).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A6 (9,7g, 12.1mmol, 72% yield).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A8 (9.8g, 11.8mmol, 70% yield).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A9 (5.4g, 11.8mmol, 70% yield).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A10 (5.4g, 11.8mmol, yield 70%).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A11 (8.9g, 12.7mmol, 75% yield).
- the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
- ITO Indium tin oxide
- distilled water glass substrate coated with a thin film of 1500 ⁇ thickness After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- a red organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R41 as the light emitting host material.
- a red organic electroluminescent device was manufactured in the same manner as in Example 1, except that D1 was used instead of the compound R41 as the light emitting host material.
- Example 1 R41 4.0 621 16.5
- Example 2 R42 4.1 621 16.4
- Example 3 R43 4.1 621 17.8
- Example 4 R44 4.3 621 17.2
- Example 5 R45 4.3 621 16.5
- Example 6 R57 4.3 621 17.4
- Example 7 R381 4.2 621 17.8
- Example 8 R383 4.5 621 17.1
- Example 9 R384 4.4 621 17.1
- Example 10 R397 4.3 621 16.3
- Example 11 R399 4.2 621 17.1
- Example 12 R542 4.6 621 15.8
- Example 13 R541 4.2 621 15.8
- Example 14 R551 4.5 621 15.9
- Example 15 R141 4.1 621 16.3
- Example 16 R241 4.2 621 18.7
- Example 17 R556 4.3 621 17.2
- Example 18 R561 4.4 621 16.3
- Example 19 R567 4.1 621 18.7
- Example 20 R571 4.2 621 19.2
- a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was ultrasonically cleaned with distilled water. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out. The substrate was then transferred to a vacuum depositor.
- ITO Indium tin oxide
- M-MTDATA 60 nm) / Compounds 4, 25, 26, 28 of Compound (80 nm) / DS-H522 (Doosan Electronics Co., Ltd.) + 5% DS-501 Doosan Electronics) (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to prepare an organic EL device.
- An organic electroluminescent device was manufactured in the same manner as in Example 33, except that NPB was used instead of the compound R44 used as the hole transport layer.
- the structure of the NPB used is as follows.
- a glass substrate coated with ITO (Indium tin oxide) to 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, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
- ITO Indium tin oxide
- An organic electroluminescent device was manufactured in the same manner as in Example 37, except for depositing at 30 nm using Alq 3 instead of the compound R41 used as the material of the electron transporting layer.
- ADN The structure of ADN used is as follows.
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Abstract
The present invention relates to a novel organic compound and an organic electroluminescence device comprising same, and the compound according to the present invention is used in an organic layer, and desirably, in a light-emitting layer in the organic electroluminescence device, thereby improving the light-emitting efficiency, the driving voltage, and life, among others characteristics, of the organic electroluminescence device.
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 정공 수송능, 전자 수송능, 발광능 등이 우수한 신규 유기 화합물 및 상기 화합물을 유기물층의 재료로서 포함하여 발광효율, 구동전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, a novel organic compound having excellent hole transporting ability, electron transporting ability, light emitting ability, etc. and the compound as a material of an organic material layer, and thus luminous efficiency. The present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서 정공이 유기물층으로 주입되고, 음극에서 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 상기 유기물층에 포함되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material included in 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.
상기 발광 물질은 발광색에 따라 청색, 녹색, 적색의 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색의 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여 발광 물질로서 호스트/도판트 계를 사용할 수 있다.The light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color. In addition, a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때 인광 도판트는 이론적으로 형광 도판트에 비해 최대 4배의 발광 효율을 향상시킬 수 있기 때문에 인광 도판트뿐만 아니라 인광 호스트에 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. In this case, since phosphorescent dopants can theoretically improve luminous efficiency up to 4 times compared to fluorescent dopants, studies on phosphorescent dopants as well as phosphorescent hosts are being conducted.
현재 발광층에 사용되는 형광 도판트/호스트 물질로는 안트라센 유도체들이 알려져 있다. 또한, 발광층에 사용되는 인광 도판트 물질로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등의 Ir을 포함하는 금속 착체 화합물이 알려져 있고, 인광 호스트 물질로는 4,4-dicarbazolybiphenyl(CBP)가 알려져 있다.At present, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. In addition, as a phosphorescent dopant material used in the light emitting layer, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 and (acac) Ir (btp) 2 are known, and as phosphorescent host materials, 4,4- dicarbazolybiphenyl (CBP) is known.
그러나, 기존의 재료들은 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있으며, 발광 특성 측면에서도 여전히 개선이 필요하다.However, the existing materials have a low glass transition temperature and poor thermal stability, and thus are not satisfactory in terms of lifespan in the organic EL device, and still need improvement in terms of light emission characteristics.
본 발명은 발광능, 정공 수송능, 정공 주입능 등이 우수하여 유기물층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel organic compound that can be used as an organic material layer having excellent light emitting ability, hole transporting ability, hole injection ability and the like.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 구동전압이 낮고, 발광효율이 높으며, 수명이 향상된 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
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).
상기 화학식 1에서,In Chemical Formula 1,
A는 N, O, S 중 하나 이상의 원자를 함유 또는 비함유하는 5원 고리이고,A is a 5-membered ring containing or not containing one or more atoms of N, O, S,
B는 6원 방향족 고리이고,B is a 6 membered aromatic ring,
Ar1은 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,Ar 1 is selected from the group consisting of hydrogen, a C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C60의 아릴렌기 및 핵원자수 5 내지 60의 헤테로아릴렌기로 이루어진 군에서 선택되며, 이때 L1은 X1, X2, Y1 내지 Y4 중 어느 하나의 탄소 또는 질소와 연결되고,L 1 and L 2 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of a C 6 ~ C 60 arylene group and a heteroarylene group having 5 to 60 nuclear atoms, wherein L 1 is Connected to carbon or nitrogen of any one of X 1 , X 2 , Y 1 to Y 4 ,
X1은 NR1 또는 CR2R3이고,X 1 is NR 1 or CR 2 R 3 ,
X2 내지 X4는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 S, O, NR4 및 CR5R6로 이루어진 군에서 선택되고, 이때 X2 및 X4 중 하나 이상은 단일결합이며, X3 및 X4가 모두 단일결합인 경우는 제외하고,X 2 to X 4 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of S, O, NR 4 and CR 5 R 6 , wherein at least one of X 2 and X 4 is a single bond Except that X 3 and X 4 are both single bonds,
Y1 내지 Y8 및 Y11 내지 Y18은 각각 독립적으로 CR7이고, 이때 복수의 R7는 서로 동일하거나 상이하며,Y 1 to Y 8 and Y 11 to Y 18 are each independently CR 7, wherein a plurality of R 7 are the same as or different from each other,
R1 내지 R7는 서로 동일하거나 상이하며, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되거나, 혹은 인접한 기와 결합(바람직하게는, R5와 다른 R5가 결합)하여 축합 방향족 고리 또는 축합 헤테로방향족 고리를 형성하며,R 1 to R 7 are the same as or different from each other, and are each independently selected from hydrogen, 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 (preferably , R 5 and other R 5 are bonded to form a condensed aromatic ring or a condensed heteroaromatic ring,
상기 A의 5원 고리와, B의 6원 방향족 고리와, 상기 Ar1의 아릴기, 헤테로아릴기와, 상기 L1 및 L2의 아릴렌기, 헤테로아릴렌기와, 상기 R1 내지 R7의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The 5-membered ring of A, the 6-membered aromatic ring of B, the aryl group and heteroaryl group of Ar 1, the arylene group and heteroarylene group of L 1 and L 2 , and the aryl of R 1 to R 7 The group and heteroaryl group are each independently deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ aryl of C 60 silyl group, C 2 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, and a C 6 ~ C 60 It may be substituted with one or more substituents selected from the group consisting of an arylamine group, wherein when the substituents are plural, they may be the same or different from each other.
또한, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나가 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.
본 발명의 화합물은 내열성, 정공 주입능, 정공 수송능, 발광능 등이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 정공 주입층 재료, 정공 수송층 재료 또는 발광층 재료로 사용될 수 있다.Since the compound of the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, light emitting ability, etc., it can be used as an organic material layer material of the organic electroluminescent device, preferably a hole injection layer material, a hole transporting layer material or a light emitting layer material.
또한, 본 발명의 화합물을 정공 주입층, 정공 수송층 및/또는 발광층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자는 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the hole injection layer, the hole transport layer and / or the light emitting layer can be greatly improved aspects such as light emission performance, driving voltage, lifespan, efficiency, such organic electroluminescent device It can be effectively applied to a full color display panel and the like.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 유기 화합물1. Organic Compound
본 발명의 유기 화합물은 '퀴나졸린과 5원 고리(A)가 결합된 모이어티'에 '직접 연결되거나 링커기(L2)를 통해 연결된 두 개의 치환기'가 직접 연결되거나 링커기(L1)를 통해 연결된 구조를 기본 골격으로 가지는 화합물로, 상기 화학식 1로 표시된다. 이때, 상기 치환기는 카바졸 모이어티, 디메틸플루오렌(dimethylfluorene) 모이어티, 디벤조티오펜(dibenzothiophene) 모이어티, 디벤조퓨란(dibenzofuran) 모이어티, 디메틸아크리딘(dimethylacridine) 모이어티, 티안트렌(thianthrene) 모이어티, 디벤조디옥사인(dibenzodioxin) 모이어티, 스피로플루오렌(spirofluorene) 등 일 수 있다.The organic compound of the present invention is a 'moiety in which a quinazoline and a 5-membered ring (A) are bonded' or 'two substituents directly connected through a linker group (L 2 )' is directly connected or a linker group (L 1 ) A compound having a structure linked through a basic skeleton, and is represented by Chemical Formula 1. In this case, the substituent is a carbazole moiety, a dimethylfluorene moiety, a dibenzothiophene moiety, a dibenzofuran moiety, a dimethylacridine moiety, a thianthrene (thianthrene) moiety, dibenzodioxin moiety, spirofluorene and the like.
보다 구체적으로, 본 발명의 화학식 1로 표시되는 화합물은 퀴나졸린에 싸이클로펜탄, 퓨란, 피라졸, 이미다졸, 옥사졸, 싸이오펜 등과 같은 5원 고리(A)가 결합되는 것으로, 이때 퀴나졸린과 유사한 에너지 준위를 갖기 때문에 도펀트의 에너지 준위에 비해 높게 조절될 수 있어 호스트 물질로 적용 가능하고, 퀴나졸린이 결합된 구조보다 높은 삼중항 에너지를 가지기 때문에 유기 전계 발광 소자의 발광층 재료로 사용시 우수한 효율 상승을 기대할 수 있다. 특히, 퀴나졸린에 싸이오펜이 결합된 화합물은 퀴나졸린에 다른 5원 고리가 결합된 화합물에 비해 장파장을 나타낼 수 있다. 또한, 상기 5원 고리(A)에 아릴기(예컨대, 페닐, 비페닐)가 도입될 경우, 반응 위치를 막아서 열안정성이 향상된다.More specifically, the compound represented by Formula 1 of the present invention is that a quinazoline is bonded to a 5-membered ring (A) such as cyclopentane, furan, pyrazole, imidazole, oxazole, thiophene, etc. Because of the similar energy level, it can be adjusted higher than the energy level of the dopant, which can be applied as a host material, and has a triplet energy higher than that of the quinazoline-coupled structure. You can expect. In particular, the compound in which thiophene is bound to quinazoline may exhibit a longer wavelength than the compound in which the five-membered ring is bound to quinazoline. In addition, when an aryl group (for example, phenyl, biphenyl) is introduced into the 5-membered ring (A), the thermal stability is improved by blocking the reaction site.
이러한 상기 화학식 1의 화합물은 '퀴나졸린과 5원 고리가 결합된 모이어티'에 하나의 치환기가 결합된 화합물에 비해 분자량 및 유리전이온도가 높아 열적 안정성이 우수하다. 또한, 화학식 1의 화합물은 좁은 밴드갭을 갖기 때문에 유기물층의 호스트 재료에 적합한 HOMO 에너지 준위, LUMO 에너지 준위를 가져 캐리어 수송성 및 발광 특성도 우수하다. 이때, 상기 화학식 1의 화합물에서, 카바졸 모이어티가 축합 방향족 고리를 형성할 경우(벤조카바졸)에는 더욱 좁은 밴드갭을 가질 수 있고, 이러한 화합물을 포함하는 유기 전계 발광 소자는 수명 특성이 크게 향상될 수 있다.The compound of Formula 1 has a higher molecular weight and glass transition temperature than the compound in which one substituent is bonded to a 'moiety in which a quinazoline and a 5-membered ring are bonded', thereby providing excellent thermal stability. In addition, since the compound of Formula 1 has a narrow bandgap, the HOMO energy level and LUMO energy level suitable for the host material of the organic material layer have excellent carrier transport properties and luminescence properties. In this case, in the compound of Formula 1, when the carbazole moiety forms a condensed aromatic ring (benzocarbazole), it may have a narrower band gap, and the organic electroluminescent device including such a compound has a long lifespan. Can be improved.
나아가, 상기 화학식 1로 표시되는 화합물은 상기 기본 골격에 질소-함유 헤테로고리(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)와 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에 정공과 전자의 결합력을 높일 수 있고, 우수한 캐리어 수송성 및 발광 특성을 나타낼 수 있다. 이러한 화합물은 유기 전계 발광 소자의 발광층 재료뿐만 아니라, 전자주입층/수송층 재료, 수명 개선층 재료로도 사용될 수 있다.Furthermore, when the compound represented by Chemical Formula 1 has a high electron-absorbing electron withdrawing group (EWG) such as a nitrogen-containing hetero ring (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since the whole molecule has a bipolar characteristic, it is possible to increase the binding force between the hole and the electron, and exhibit excellent carrier transport and luminescence properties. Such a compound can be used not only as the light emitting layer material of the organic electroluminescent device, but also as the electron injection layer / transport layer material and the life improvement layer material.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에 발광층 재료뿐만 아니라, 정공주입층/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다. 특히, 큰 전자 주게기가 결합된 화합물은 삼중항 에너지가 높기 때문에 정공 수송 재료로 사용할 경우, TTF(triplet-triplet fusion)효과로 인해 우수한 효율 상승을 기대할 수 있다.In addition, the compound of Formula 1, when the electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group is bonded to the basic skeleton, the hole injection and transport is smooth In addition to the light emitting layer material, it can be usefully used as a hole injection layer / transport layer or a light emitting auxiliary layer material. In particular, the compound having a large electron donor has high triplet energy, and thus, when used as a hole transporting material, an excellent efficiency increase may be expected due to the triple-triplet fusion effect.
따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(적색의 인광 호스트 재료), 전자 수송층/주입층 재료 및 정공 수송층/주입층 재료, 발광보조층 재료, 수명 개선층 재료, 더욱 바람직하게는 발광층 재료, 전자 주입층 재료, 정공 수송층 재료로 사용될 수 있다. 또한, 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (red phosphorescent host material), an electron transport layer / injection layer material and a hole transport layer / injection layer material, light emitting auxiliary layer Material, life improvement layer material, more preferably, light emitting layer material, electron injection layer material, hole transport layer material. In addition, the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 5 중 어느 하나로 표시되는 화합물로 구체화될 수 있다.The compound represented by Formula 1 of the present invention may be embodied as a compound represented by any one of the following Formulas 2 to 5.
상기 화학식 2 내지 5에서,In Chemical Formulas 2 to 5,
A, B, Ar1
, L2, X1 내지 X4, Y1 내지 Y8, Y11 내지 Y18은 상기 화학식 1에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 1 to X 4 , Y 1 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
보다 구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 8 중 어느 하나로 표시되는 화합물일 수 있다.More specifically, the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 6 to 8.
상기 화학식 6 내지 8에서,In Chemical Formulas 6 to 8,
A, B, Ar1
, L2, X3, X4, Y5 내지 Y8, Y11 내지 Y18은 상기 화학식 1에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 3 , X 4 , Y 5 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
또한, 상기 화학식 1로 표시되는 화합물은 하기 화학식 9 내지 11 중 어느 하나로 표시되는 화합물일 수 있다.In addition, the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 9 to 11.
상기 화학식 9 내지 11에서,In Chemical Formulas 9 to 11,
A, B, Ar1
, L2, X1, X2, Y5 내지 Y8, Y11 내지 Y18은 상기 화학식 1에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 1 , X 2 , Y 5 to Y 8 , Y 11 to Y 18 are the same as defined in Chemical Formula 1.
이러한 상기 화학식 1로 표시되는 화합물에서, 
(*는 화학식 1의 L1과 결합하는 부위를 의미함)는 하기 A-1 내지 A-18로 표시되는 치환체 중 어느 하나로 표시되는 것이 바람직하다.In the compound represented by Formula 1, (* Means a site which binds to L 1 of Formula 1) is preferably represented by any one of the substituents represented by the following A-1 to A-18.
상기 A-1 내지 A-18에서,In the above A-1 to A-18,
Ar1은 상기 화학식 1에서 정의한 바와 같고,Ar 1 is as defined in Formula 1,
R8는 서로 동일하거나 상이하며, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되며,R 8 is the same as or different from each other, and each independently selected from hydrogen, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,
상기 R8의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The aryl group of said R 8, heteroaryl groups each independently selected from deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of the, C 6 Aryl group of ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 ~ C 40 , aryloxy group of C 6 ~ C 60 , alkylsilyl group of C 1 ~ C 40 , C 6 An arylsilyl group of ˜C 60 , an alkyl boron group of C 2 ˜C 40, an aryl boron group of C 6 ˜C 60 , an arylphosphine group of C 6 ˜C 60 , an arylphosphine oxide group of C 6 ˜C 60 , and It may be substituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylamine group, wherein when there are a plurality of the substituents, they may be the same or different from each other.
이때, 상기 복수의 R6 중 적어도 하나는 C6~C60의 아릴기인 것이 바람직하고, 페닐인 것이 더욱 바람직하다.At this time, at least one of the plurality of R 6 is preferably an aryl group of C 6 ~ C 60 , more preferably phenyl.
또한, 상기 화학식 1로 표시되는 화합물에서, 
는 하기 B-1 내지 B-12로 표시되는 치환체 중 어느 하나로 표시되는 것이 바람직하다.In addition, in the compound represented by Formula 1, Is preferably represented by any one of substituents represented by B-1 to B-12.
상기 B-1 내지 B-12에서,In the above B-1 to B-12,
R4 내지 R6는 상기 화학식 1에서 정의한 바와 같다.R 4 to R 6 are the same as defined in Chemical Formula 1.
이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 화합물 R1 내지 R635으로 구체화될 수 있으나, 이들로 한정되는 것은 아니다.The compound represented by Chemical Formula 1 of the present invention described above may be embodied by the following compounds R1 to R635, but is not limited thereto.
한편, 본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
본 발명에서 아릴은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 헤테로아릴은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 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 in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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 heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 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 aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 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 alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. 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 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 시클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples of heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
2. 유기 2. Organic
전계Electric field
발광 소자 Light emitting element
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
보다 구체적으로, 본 발명의 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device of the present invention comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is a compound represented by Formula 1 It may include. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.
상기 발광층은 호스트 재료(바람직하게는, 인광 호스트 재료)를 포함할 수 있는데, 이때, 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 발광층은 상기 화학식 1의 화합물 이외의 화합물을 호스트로 포함할 수 있다.The emission layer may include a host material (preferably, a phosphorescent host material), in which case, the host material may include the compound of Formula 1 above. In addition, the light emitting layer of the organic EL device of the present invention may include a compound other than the compound of Formula 1 as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층, 전자 주입층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 정공 수송층, 전자 수송층, 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic EL device of the present invention is not particularly limited, but non-limiting examples include a substrate, an anode, a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer, an electron injection layer, and a cathode. It may be a stacked structure sequentially. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the hole transport layer, the electron transport layer, the light emitting layer is represented by the formula (1) It may include a compound represented. In addition, the structure of the organic EL device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.
한편, 본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.On the other hand, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes a compound represented by the formula (1). have.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like can be used.
또한, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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.
또한, 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 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and 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.
[[
준비예Preparation
1] A1의 합성 1] Synthesis of A1
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 5.8 g (20.2 mmol) of 9-phenyl-9H-carbazole-3-ylboronic acid, 1.0 g of Pd (PPh 3 ) 4 under nitrogen stream mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, followed by stirring at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A1 (5.6g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A1 (5.6g, 12.1mmol, 72% yield).
GC-Mass (이론치: 458.55g/mol, 측정치: 458g/mol)GC-Mass (Theoretical value: 458.55 g / mol, Measured value: 458 g / mol)
1H-NMR: δ 7.25~7.28(m, 2H), 7.50~7.67(m, 13H), 7.85~7.91(m, 3H), 8.15(d, 1H), 8.48(t, 2H), 10.01(s, 1H)1 H-NMR: δ 7.25-7.28 (m, 2H), 7.50-7.67 (m, 13H), 7.85-7.91 (m, 3H), 8.15 (d, 1H), 8.48 (t, 2H), 10.01 (s, 1H)
[[
준비예Preparation
2] A2의 합성 2] Synthesis of A2
질소 기류 하에서 7-(10-bromo-7H-benzo[c]carbazole-7-yl)-2,9-diphenylthieno[2,3-f]quinazoline 10.7g (16.9 mmol), 9H-carbazole-3-ylboronic acid 4.3g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.7- (10-bromo-7H-benzo [c] carbazole-7-yl) -2,9-diphenylthieno [2,3-f] quinazoline 10.7 g (16.9 mmol), 9H-carbazole-3-ylboronic under nitrogen stream Add 4.3 g (20.2 mmol) of acid, 1.0 g (5 mol%) of Pd (PPh 3 ) 4 , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol. Stir for hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A2 (8.5g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A2 (8.5g, 11.8mmol, yield 70%).
GC-Mass (이론치: 718.87g/mol, 측정치: 718g/mol)GC-Mass (Theoretical value: 718.87g / mol, Measured value: 718g / mol)
1H-NMR: δ 7.29(m, 1H), 7.42~7.50(m, 8H), 7.64~7.75(m 15H), 9.05~8.15(m. 7H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 7.29 (m, 1H), 7.42 to 7.50 (m, 8H), 7.64 to 7.75 (m 15H), 9.05 to 8.15 (m. 7H), 8.54 (d, 1H), 10.01 (s, 1H )
[[
준비예Preparation
3] A3의 합성 3] Synthesis of A3
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0 (16.8 mmol), 9-(2,9-diphenylthieno[2,3-f]quinazoline-7-yl)-9H-carbazole-3-ylboronic acid 11.1g (20.2 mmol), Pd(PPh3)4 0.6g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethano l80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.10-bromo-7H-benzo [c] carbazole 5.0 (16.8 mmol), 9- (2,9-diphenylthieno [2,3-f] quinazoline-7-yl) -9H-carbazole-3-ylboronic acid under nitrogen stream 11.1g (20.2 mmol), Pd (PPh 3 ) 4 0.6g (5 mol%), 7.0g (50.6 mmol) potassium carbonate and Toluene / H 2 O / Ethano l80ml / 40ml / 40ml Was stirred.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A3 (8.5g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A3 (8.5g, 11.8mmol, yield 70%).
GC-Mass (이론치: 718.87g/mol, 측정치: 718g/mol)GC-Mass (Theoretical value: 718.87g / mol, Measured value: 718g / mol)
1H-NMR: δ 7.26~7.48(m, 8H), 7.65~7.85(m, 17H), 8.05(d, 1H), 8.15(d, 1H), 8.54(d, 2H), 10.01(s, 1H)1 H-NMR: δ 7.26 to 7.48 (m, 8H), 7.65 to 7.85 (m, 17H), 8.05 (d, 1H), 8.15 (d, 1H), 8.54 (d, 2H), 10.01 (s, 1H)
[[
준비예Preparation
4] A4의 합성 4] Synthesis of A4
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 7-phenyl-7H-benzo[c]carbazole-10-ylboronic acid 6.8g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 6.8 g (20.2 mmol) of 7-phenyl-7H-benzo [c] carbazole-10-ylboronic acid, and Pd (PPh 3 ) 4 under nitrogen stream 1.0 g (5 mol%), 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A4 (6.4g, 12.7mmol, 수율 75%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A4 (6.4g, 12.7mmol, 75% yield).
GC-Mass (이론치: 508.61g/mol, 측정치: 508g/mol)GC-Mass (Theoretical value: 508.61 g / mol, Measured value: 508 g / mol)
1H-NMR: δ 7.45~7.63(m, 15H), 7.88~7.93(m, 4H), 8.15(d, 2H), 8.50(d, 2H), 10.01(s, 1H)1 H-NMR: δ 7.45-7.63 (m, 15H), 7.88-7.73 (m, 4H), 8.15 (d, 2H), 8.50 (d, 2H), 10.01 (s, 1H)
[[
준비예Preparation
5] A5의 합성 5] Synthesis of A5
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 7-(2,9-diphenylthieno[2,3-f]quinazoline-7-yl)-7H-benzo[c]carbazole-10-ylboronic acid 12.1g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 7- (2,9-diphenylthieno [2,3-f] quinazoline-7-yl) -7H-benzo [c] carbazole under nitrogen stream 12.1 g (20.2 mmol) of -10-ylboronic acid, 1.0 g (5 mol%) of Pd (PPh 3 ) 4 , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol Stir at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A5 (9,7g, 12.7mmol, 수율 75%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A5 (9,7g, 12.7mmol, yield 75%).
GC-Mass (이론치: 768.92g/mol, 측정치: 768g/mol)GC-Mass (Theoretical value: 768.92 g / mol, Measured value: 768 g / mol)
1H-NMR: δ 7.42~7.49(m, 6H), 7.63~7.79(m, 20H), 8.05(d, 1H), 8.15(d, 2H), 8.54(d, 2H), 10.01(s, 1H)1 H-NMR: δ 7.42-7.49 (m, 6H), 7.63-7.79 (m, 20H), 8.05 (d, 1H), 8.15 (d, 2H), 8.54 (d, 2H), 10.01 (s, 1H)
[[
준비예Preparation
6] A6의 합성 6] Synthesis of A6
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 9-(4,6-diphenylthieno[3,2-d]quinazoline-2-yl)-6-phenyl-9H-carbazole-3-ylboronic acid 11.6g (20.2 mmol), Pd(PPh3)4
1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 9- (4,6-diphenylthieno [3,2-d] quinazoline-2-yl) -6-phenyl-9H-carbazole under nitrogen stream -3-ylboronic acid 11.6g (20.2 mmol), Pd (PPh 3 ) 4 1.0 g (5 mol%), 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A6 (9,7g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A6 (9,7g, 12.1mmol, 72% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
1H-NMR: δ 7.42~7.50(m, 11H), 7.63~7.81(m, 15H), 8.01(d, 1H), 8.05(d, 1H), 8.15(d, 3H), 8.54(d, 2H), 10.01(s, 1H)1 H-NMR: δ 7.42 to 7.50 (m, 11H), 7.63 to 7.81 (m, 15H), 8.01 (d, 1H), 8.05 (d, 1H), 8.15 (d, 3H), 8.54 (d, 2H) , 10.01 (s, 1H)
[[
준비예Preparation
7] A7의 합성 7] Synthesis of A7
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol) 3-(9-phenyl-9H-carbazole-3-yl)phenylboronic acid 7.4g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethano l80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole 3- (9-phenyl-9H-carbazole-3-yl) phenylboronic acid 7.4 g (20.2 mmol), Pd (PPh 3 ) 4 1.0g (5 mol%), and 7.0g (50.6 mmol) of potassium carbonate and Toluene / H 2 O / Ethano l80ml / 40ml / 40ml were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A7 (6.5g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A7 (6.5g, 12.1mmol, 72% yield).
GC-Mass (이론치: 534.65g/mol, 측정치: 534g/mol)GC-Mass (Theoretical value: 534.65 g / mol, Measured value: 534 g / mol)
1H-NMR: δ 7.25(m, 1H), 7.51~7.69(m, 18H), 7.82(d, 1H), 8.01(d, 1H), 8.14~8.17(m, 3H), 8.53(d, 1H), 10.01(s, 1H)1H-NMR: δ 7.25 (m, 1H), 7.51-7.69 (m, 18H), 7.82 (d, 1H), 8.01 (d, 1H), 8.14-8.17 (m, 3H), 8.53 (d, 1H) , 10.01 (s, 1H)
[[
준비예Preparation
8] A8의 합성 8] Synthesis of A8
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 9.8g (16.9 mmol), 9-phenyl-9'-(4-phenylquinazoline-2-yl)-9H,9'H-3,3'-bicarbazole-6-ylboronic acid 13.3g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.9.8 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 9-phenyl-9 '-(4-phenylquinazoline-2-yl) -9H, 9'H-3,3'-bicarbazole under nitrogen stream Add -6-ylboronic acid 13.3g (20.2 mmol), Pd (PPh 3 ) 4 1.0g (5 mol%), potassium carbonate 7.0g (50.6 mmol) and Toluene / H 2 O / Ethanol 80ml / 40ml / 40ml Stir at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A8 (9.8g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A8 (9.8g, 11.8mmol, 70% yield).
GC-Mass (이론치: 827.97g/mol, 측정치: 827g/mol)GC-Mass (Theoretical value: 827.97 g / mol, Measured value: 827 g / mol)
1H-NMR: δ 7.25(m, 1H), 7.43~7.78(m, 25H), 8.02~8.17(m, 9H), 8.53(d, 1H), 10.01(s, 1H)1 H-NMR: δ 7.25 (m, 1 H), 7.43-77.7 (m, 25 H), 8.02-8.17 (m, 9H), 8.53 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
9] A9의 합성 9] Synthesis of A9
질소 기류 하에서 2-bromo-5H-benzo[b]carbazole 5.0g (16.9 mmol) 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 2-bromo-5H-benzo [b] carbazole under nitrogen stream 5.8 g (20.2 mmol) of 9-phenyl-9H-carbazole-3-ylboronic acid, 1.0 g (5 mol) of Pd (PPh 3 ) 4 %), And 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A9 (5.4g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A9 (5.4g, 11.8mmol, 70% yield).
GC-Mass (이론치: 458.55g/mol, 측정치: 458g/mol)GC-Mass (Theoretical value: 458.55 g / mol, Measured value: 458 g / mol)
1H-NMR: δ 7.28~7.59(m, 16H), 7.88~7.93(m, 3H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 7.28-7.59 (m, 16H), 7.88-7.73 (m, 3H), 8.15 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
10] A10의 합성 10] Synthesis of A10
질소 기류 하에서 8-bromo-11H-benzo[a]carbazole 5.0g (16.9 mmol), 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 8-bromo-11H-benzo [a] carbazole under nitrogen stream, 5.8 g (20.2 mmol) of 9-phenyl-9H-carbazole-3-ylboronic acid, 1.0 g of Pd (PPh 3 ) 4 mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, followed by stirring at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A10 (5.4g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A10 (5.4g, 11.8mmol, yield 70%).
GC-Mass (이론치: 458.55g/mol, 측정치: 458g/mol)GC-Mass (Theoretical value: 458.55 g / mol, Measured value: 458 g / mol)
1H-NMR: δ 7.27~7.33(m, 2H), 7.42~7.65(m, 12H), 7.77~7.84(m, 3H), 8.12~8.14(m, 2H), 8.52~8.54(m, 2H), 10.01(s, 1H)1 H-NMR: δ 7.27-7.73 (m, 2H), 7.42-7.75 (m, 12H), 7.77-7.84 (m, 3H), 8.12-8.14 (m, 2H), 8.52-8.54 (m, 2H), 10.01 (s, 1H)
[[
준비예Preparation
11] A11의 합성 11] Synthesis of A11
질소 기류 하에서 10-bromo-7-(4-phenylquinazoline-2-yl)-7H-benzo[c]carbazole 8.4g (16.9 mmol), 9-phenyl-9H-carbazole-3,6-diyldiboronic acid 6.7g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.8.4 g (16.9 mmol) of 10-bromo-7- (4-phenylquinazoline-2-yl) -7H-benzo [c] carbazole, 6.7 g of 9-phenyl-9H-carbazole-3,6-diyldiboronic acid under nitrogen stream ( 20.2 mmol), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours. .
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A11 (8.9g, 12.7mmol, 수율 75%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A11 (8.9g, 12.7mmol, 75% yield).
GC-Mass (이론치: 706.60g/mol, 측정치: 706g/mol)GC-Mass (Theoretical value: 706.60 g / mol, Measured value: 706 g / mol)
1H-NMR: δ 2.0(s, 2H), 7.45~7.58(m, 15H), 7.72~7.78(m,5H),8.02~8.06(m, 4H), 8.16~8.18(m, 4H), 8.54(d, 1H)1H-NMR: δ 2.0 (s, 2H), 7.45 ~ 7.58 (m, 15H), 7.72 ~ 7.78 (m, 5H), 8.02 ~ 8.06 (m, 4H), 8.16 ~ 8.18 (m, 4H), 8.54 ( d, 1H)
[[
준비예Preparation
12] A12의 합성 12] Synthesis of A12
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 9,9-dimethyl-9H-fluoren-2-ylboronic acid 4.8 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole under nitrogen stream, 4.8 g (20.2 mmol) of 9,9-dimethyl-9H-fluoren-2-ylboronic acid, 1.0 g of Pd (PPh 3 ) 4 (5 mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A12 (5.0g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A12 (5.0g, 12.1mmol, 72% yield).
GC-Mass (이론치: 409.52g/mol, 측정치: 409g/mol)GC-Mass (Theoretical value: 409.52 g / mol, Measured value: 409 g / mol)
1H-NMR: δ 1.73(m, 6H), 7.25(m, 1H), 7.34(m, 1H), 7.55~7.62(m, 7H), 7.76(s, 2H), 7.76~7.79(m, 3H), 8.16(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1H-NMR: δ 1.73 (m, 6H), 7.25 (m, 1H), 7.34 (m, 1H), 7.55-7.82 (m, 7H), 7.76 (s, 2H), 7.76-7.79 (m, 3H) , 8.16 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
13] A13의 합성 13] Synthesis of A13
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), dibenzo[b,d]thiophen-2-ylboronic acid 4.6 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 4.6 g (20.2 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid, 1.0 g (5 of Pd (PPh 3 ) 4 under nitrogen stream mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, followed by stirring at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A13 (4.7g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A13 (4.7g, 11.8mmol, 70% yield).
GC-Mass (이론치: 399.51g/mol, 측정치: 399g/mol)GC-Mass (Theoretical value: 399.51 g / mol, Measured value: 399 g / mol)
1H-NMR: δ 7.50~7.51(m, 2H), 7.65~7.76(m, 6H), 7.88~7.89(m, 2H), 7.98~8.00(m, 3H), 8.15(d, 1H), 8.45~49(d, 2H), 10.01(s, 1H)1H-NMR: δ 7.50-7.51 (m, 2H), 7.65-7.72 (m, 6H), 7.88-7.89 (m, 2H), 7.98-8.00 (m, 3H), 8.15 (d, 1H), 8.45- 49 (d, 2H), 10.01 (s, 1H)
[[
준비예Preparation
14] A14의 합성 14] Synthesis of A14
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), dibenzo[b,d]furane-2-ylboronic acid 4.3 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole under nitrogen stream, 4.3 g (20.2 mmol) of dibenzo [b, d] furane-2-ylboronic acid, 1.0 g (5 of Pd (PPh 3 ) 4 mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, followed by stirring at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A14 (4.5g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A14 (4.5g, 11.8mmol, 70% yield).
GC-Mass (이론치: 383.44g/mol, 측정치: 383g/mol)GC-Mass (Theoretical value: 383.44 g / mol, Measured value: 383 g / mol)
1H-NMR: δ 7.35~38(m, 2H), 7.65~7.85 (m, 12H), 8.15(d, 1H), 8.53(d, 1H), 10.01(s, 1H)1 H-NMR: δ 7.35-38 (m, 2H), 7.65-7.85 (m, 12H), 8.15 (d, 1H), 8.53 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
15] A15의 합성 15] Synthesis of A15
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol) 9,9'-spirobi[fluorene]-2-ylboronic acid 7.3 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole under nitrogen stream 9,9'-spirobi [fluorene] -2-ylboronic acid 7.3 g (20.2 mmol), Pd (PPh 3 ) 4 1.0 g ( 5 mol%), and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A15 (9.0g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A15 (9.0g, 12.1mmol, 72% yield).
GC-Mass (이론치: 531.64g/mol, 측정치: 531g/mol)GC-Mass (Theoretical value: 531.64 g / mol, Measured value: 531 g / mol)
1H-NMR: δ 7.16~7.35(m, 8H), 7.65~7.75(m, 11H), 7.86~7.89(m,3H), 8.16(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 7.16 to 7.35 (m, 8H), 7.65 to 7.75 (m, 11H), 7.86 to 7.89 (m, 3H), 8.16 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
16] A16의 합성 16] Synthesis of A16
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), thianthren-2-ylboronic acid 5.3 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 5.3 g (20.2 mmol) of thianthren-2-ylboronic acid, 1.0 g (5 mol%) of Pd (PPh 3 ) 4 , and potassium under nitrogen stream 7.0 g (50.6 mmol) of carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A16 (5.2g, 12.0mmol, 수율 71%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A16 (5.2g, 12.0mmol, 71% yield).
GC-Mass (이론치: 431.57g/mol, 측정치: 431g/mol)GC-Mass (Theoretical value: 431.57 g / mol, Measured value: 431 g / mol)
1H-NMR: δ 6.99(m, 2H), 7.21~7.24(m, 5H), 7.63~7.67(m, 5H), 7.76(s, 1H), 7.87(d, 1H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 6.99 (m, 2H), 7.21 to 7.44 (m, 5H), 7.63 to 7.57 (m, 5H), 7.76 (s, 1H), 7.87 (d, 1H), 8.15 (d, 1H) , 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
17] A17의 합성 17] Synthesis of A17
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), dibenzo[b,e][1,4]dioxin-2-ylboronic acid 4.6 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 4.6 g (20.2 mmol) of dibenzo [b, e] [1,4] dioxin-2-ylboronic acid, Pd (PPh 3 ) under nitrogen stream 4 1.0g (5 mol%), 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A17 (4.9g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A17 (4.9g, 12.1mmol, 72% yield).
GC-Mass (이론치: 399.44g/mol, 측정치: 399g/mol)GC-Mass (Theoretical value: 399.44 g / mol, Measured value: 399 g / mol)
1H-NMR: δ 6.83(m, 2H), 7.13~7.16(m, 3H), 7.41~7.43(m, 2H), 7.63~7.67(m, 5H), 7.76(s, 1H), 7.87(d, 1H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 6.83 (m, 2H), 7.13 to 7.16 (m, 3H), 7.41 to 7.43 (m, 2H), 7.63 to 7.57 (m, 5H), 7.76 (s, 1H), 7.87 (d, 1H), 8.15 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
18] A18의 합성 18] Synthesis of A18
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-ylboronic acid 6.7 g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 6.7 g (20.2 mmol) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-ylboronic acid, Pd ( PPh 3 ) 4 1.0g (5 mol%), and 7.0g (50.6 mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A18 (6.1g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A18 (6.1g, 12.1mmol, 72% yield).
GC-Mass (이론치: 500.63g/mol, 측정치: 500g/mol)GC-Mass (Theoretical value: 500.63 g / mol, Measured value: 500 g / mol)
1H-NMR: δ 1.72(m, 6H), 6.35~6,54(m, 3H), 6.73~6.79(m, 4H), 7.11~7.20(m, 5H), 7.63~7.68(m, 5H), 7.76(s, 1H), 7.87(d, 1H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)1 H-NMR: δ 1.72 (m, 6H), 6.35-6,54 (m, 3H), 6.73-6.69 (m, 4H), 7.11-7.20 (m, 5H), 7.63-7.68 (m, 5H), 7.76 (s, 1H), 7.87 (d, 1H), 8.15 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H)
[[
준비예Preparation
19] A19의 합성 19] Synthesis of A19
질소 기류 하에서 10-bromo-7-(4-phenylbenzo[h]quinazolin-2-yl)-7H-benzo[c]carbazole 9.3g(16.9 mmol), 9-phenyl-9H-carbazole-3,6-diyldiboronic acid 6.7g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%) 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.10-bromo-7- (4-phenylbenzo [h] quinazolin-2-yl) -7H-benzo [c] carbazole 9.3 g (16.9 mmol), 9-phenyl-9H-carbazole-3,6-diyldiboronic under nitrogen stream 6.7g (20.2 mmol) acid, 1.0g (5 mol%) of Pd (PPh 3 ) 4, 7.0g (50.6 mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added for 3 hours at 110 ℃. Was stirred.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A19 (9,2g, 12.1mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A19 (9,2g, 12.1mmol, 72% yield).
GC-Mass (이론치: 756.66g/mol, 측정치: 756g/mol)GC-Mass (Theoretical value: 756.66 g / mol, Measured value: 756 g / mol)
1H-NMR: δ 2.0(s, 2H), 7.45~8.12(m, 27H), 8.16~8.81(m, 3H), 8.54(d, 1H)1H-NMR: δ 2.0 (s, 2H), 7.45 ~ 8.12 (m, 27H), 8.16 ~ 8.81 (m, 3H), 8.54 (d, 1H)
[[
준비예Preparation
20] A20의 합성 20] Synthesis of A20
질소 기류 하에서 10-bromo-7-(4-phenylquinazolin-2-yl)-7H-benzo[c]carbazole 8.4g (16.9 mmol), 9,9-dimethyl-9H-fluorene-2,7-diyldiboronic acid 5.7g (20.2 mmol), Pd(PPh3)4 1.0g (5 mol%), 및 potassium carbonate 7.0g (50.6 mmol)와 Toluene/H2O/Ethanol 80ml/40ml/40ml를 넣고 110℃에서 3시간 동안 교반하였다.8.4 g (16.9 mmol) of 10-bromo-7- (4-phenylquinazolin-2-yl) -7H-benzo [c] carbazole under nitrogen stream, 9,9-dimethyl-9H-fluorene-2,7-diyldiboronic acid 5.7 Add g (20.2 mmol), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol for 3 hours at 110 ° C. Stirred.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A20 (7.8g, 11.8mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A20 (7.8g, 11.8mmol, yield 70%).
GC-Mass (이론치: 657.57g/mol, 측정치: 657g/mol)GC-Mass (Theoretical value: 657.57 g / mol, Measured value: 657 g / mol)
1H-NMR: δ 1.72(s, 6H), 2.0(s, 2H), 7.17(d, 1H), 7.34(s, 1H), 7.41(m, 1H), 7.51(m, 2H), 7.56(s, 1H), 7.64~7.67(m, 5H), 7.78~8.03(m, 9H), 8.16~8.81(m, 3H), 8.54(d, 1H)1 H-NMR: δ 1.72 (s, 6H), 2.0 (s, 2H), 7.17 (d, 1H), 7.34 (s, 1H), 7.41 (m, 1H), 7.51 (m, 2H), 7.56 (s , 1H), 7.64-7.57 (m, 5H), 7.78-8.03 (m, 9H), 8.16-8.81 (m, 3H), 8.54 (d, 1H)
[[
합성예Synthesis Example
1] R41의 합성 1] Synthesis of R41
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-2,9-diphenylthieno[2,3-f]quinazoline 5.0g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6g (12.1mmol), 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline 5.0g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R41 6.3g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R41 6.3g (7.9mmol, 65% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
[[
합성예Synthesis Example
2] R42의 합성 2] Synthesis of R42
질소 기류 하에서 A1 5.6g (12.1mmol), 3-chloro-1,8-diphenylthieno[3,2-f]quinazoline 5.0g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6g (12.1mmol), 3-chloro-1,8-diphenylthieno [3,2-f] quinazoline 5.0g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R42 6.3g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R42 6.3g (7.9mmol, 65% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
[[
합성예Synthesis Example
3] R43의 합성 3] Synthesis of R43
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-2-phenyl-9-(9-phenyl-9H-carbazole-3-yl)thieno[2,3-f]quinazoline 7.2g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 7-chloro-2-phenyl-9- (9-phenyl-9H-carbazole-3-yl) thieno [2,3-f] quinazoline 7.2 g (13.4 mmol) under a nitrogen stream, Pd 2 (dba) 3 0.6g ( 5 mol%), into the tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R43 7.3g (7.7mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R43 7.3g (7.7mmol, 63% yield).
GC-Mass (이론치: 960.15g/mol, 측정치: 960g/mol)GC-Mass (Theoretical value: 960.15 g / mol, Measured value: 960 g / mol)
[[
합성예Synthesis Example
4] R44의 합성 4] Synthesis of R44
질소 기류 하에서 A1 5.6g (12.1mmol), 4-(7-chloro-2-phenylthieno[2,3-f]quinazoline-9-yl)-N,N-diphenylaniline 7.2g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 4- (7-chloro-2-phenylthieno [2,3-f] quinazoline-9-yl) -N, N-diphenylaniline 7.2 g (13.4 mmol), Pd 2 dba) 3 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol), sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene were added and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R44 7.1g (7.4mmol, 수율 61%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R44 7.1g (7.4mmol, 61% yield).
GC-Mass (이론치: 962.17g/mol, 측정치: 962g/mol)GC-Mass (Theoretical value: 962.17g / mol, Measured value: 962g / mol)
[[
합성예Synthesis Example
5] R45의 합성 5] Synthesis of R45
질소 기류 하에서 A3 8.5g (11.8mmol), bromobenzene 2.0g (13.0mmol), Pd2(dba)3 0.7g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 4.1g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.8.5 g (11.8 mmol) of A3, 2.0 g (13.0 mmol) of bromobenzene, 0.7 g (5 mol%) of Pd 2 (dba) 3 , 0.1 g (0.6 mmol) of tri- tert- butylphosphine, and Sodium tert-butoxide 4.1 under nitrogen stream g (35.4mmol) and Toluene 100ml were added and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R45 6.1g (7.7mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R45 6.1g (7.7mmol, 65% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
[[
합성예Synthesis Example
6] R57의 합성 6] Synthesis of R57
질소 기류 하에서 A2 8.5g (11.8mmol), 2-chloro-4-phenylquinazoline 3.1g (13.0mmol), Pd2(dba)3 0.7g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 4.1g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A2 8.5g (11.8mmol), 2- chloro-4-phenylquinazoline 3.1g (13.0mmol), Pd 2 (dba) 3 0.7g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) And sodium tert-butoxide 4.1g (35.4mmol) and Toluene 100ml were added and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R57 7.1g (7.7mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R57 7.1g (7.7mmol, 65% yield).
GC-Mass (이론치: 923.09g/mol, 측정치: 923g/mol)GC-Mass (Theoretical value: 923.09 g / mol, Measured value: 923 g / mol)
[[
합성예Synthesis Example
7] R381의 합성 7] Synthesis of R381
질소 기류 하에서 A4 6.4g (12.7mmol), 7-chloro-2,9-diphenylthieno[2,3-f]quinazoline 5.2g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.4g (12.7mmol), 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline 5.2g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R381 7.1g (8.4mmol, 수율 66%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R381 7.1g (8.4mmol, 66% yield).
GC-Mass (이론치: 845.02g/mol, 측정치: 845g/mol)GC-Mass (Theoretical value: 845.02 g / mol, Measured value: 845 g / mol)
[[
합성예Synthesis Example
8] R383의 합성 8] Synthesis of R383
질소 기류 하에서 A4 6.4g (12.7mmol), 7-chloro-2-phenyl-9-(9-phenyl-9H-carbazole-3-yl)thieno[2,3-f]quinazoline 7.5g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.4 g (12.7 mmol) A4, 7-chloro-2-phenyl-9- (9-phenyl-9H-carbazole-3-yl) thieno [2,3-f] quinazoline 7.5 g (13.9 mmol), under nitrogen stream Pd 2 (dba) 3 0.6g ( 5 mol%), into the tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R383 8.4g (8.4mmol, 수율 66%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain 8.4g (8.4mmol, 66% yield) of the target compound R383.
GC-Mass (이론치: 1010.21g/mol, 측정치: 1010g/mol)GC-Mass (Theoretical value: 1010.21 g / mol, Measured value: 1010 g / mol)
[[
합성예Synthesis Example
9] R384의 합성 9] Synthesis of R384
질소 기류 하에서 A4 6.4g (12.7mmol), 4-(7-chloro-2-phenylthieno[2,3-f]quinazoline-9-yl)-N,N-diphenylaniline 7.5g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.4 g (12.7 mmol) A4, 4- (7-chloro-2-phenylthieno [2,3-f] quinazoline-9-yl) -N, N-diphenylaniline 7.5 g (13.9 mmol), Pd 2 dba) 3 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol), 3.6g (38.0mmol) of sodium tert-butoxide and 100ml of Toluene were added and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R384 8.5g (8.4mmol, 수율 66%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain 8.5g (8.4mmol, 66% yield) of the target compound R384.
GC-Mass (이론치: 1012.23g/mol, 측정치: 1012g/mol)GC-Mass (Theoretical value: 1012.23 g / mol, Measured value: 1012 g / mol)
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합성예Synthesis Example
10] R397의 합성 10] Synthesis of R397
질소 기류 하에서 A5 9.7g (12.7mmol), 2-chloro-4-phenylquinazoline 3.4g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A5 9.7g (12.7mmol), 2- chloro-4-phenylquinazoline 3.4g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) And sodium tert-butoxide 3.6g (38.0mmol) and Toluene 100ml were added and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R397 8.0g (8.2mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain 8.0g (8.2mmol, yield 65%) of the title compound R397.
GC-Mass (이론치: 973.15g/mol, 측정치: 973g/mol)GC-Mass (Theoretical value: 973.15 g / mol, Measured value: 973 g / mol)
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합성예Synthesis Example
11] R399의 합성 11] Synthesis of R399
질소 기류 하에서 A5 9.7g (12.7mmol), 2-bromodibenzo[b,d]furane 3.4g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.9.7 g (12.7 mmol) of A5, 3.4 g (13.9 mmol) of 2-bromodibenzo [b, d] furane, 0.6 g (5 mol%) of Pd 2 (dba) 3 , 0.1 g (0.6 of tri- tert- butylphosphine) mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml of Toluene were added and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R399 7.3g (7.8mmol, 수율 62%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R399 7.3g (7.8mmol, 62% yield).
GC-Mass (이론치: 935.10g/mol, 측정치: 935g/mol)GC-Mass (Theoretical value: 935.10 g / mol, Measured value: 935 g / mol)
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합성예Synthesis Example
12] R542의 합성 12] Synthesis of R542
질소 기류 하에서 A6 9.1g (12.1mmol), bromobenzene 3.4g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.9.1 g (12.1 mmol) A6, 3.4 g (13.9 mmol) bromobenzene, 0.6 g (5 mol%) Pd 2 (dba) 3 , 0.1 g (0.6 mmol) tri- tert- butylphosphine, and sodium tert-butoxide 3.6 g (38.0mmol) and Toluene 100ml were added and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R542 6.9g (7.8mmol, 수율 62%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the target compound R542 6.9g (7.8mmol, 62% yield).
GC-Mass (이론치: 871.06g/mol, 측정치: 871g/mol)GC-Mass (Theoretical value: 871.06 g / mol, Measured value: 871 g / mol)
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합성예Synthesis Example
13] R541의 합성 13] Synthesis of R541
질소 기류 하에서 A7 6.5g (12.1mmol), 7-chloro-2,9-diphenylthieno[2,3-f]quinazoline 4.4g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 의 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.5g (12.1mmol), 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline 4.4g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - tert -butylphosphine 0.1g (0.6mmol) and put 100ml of Toluene and Sodium tert-butoxide 3.5g (36.4mmol) was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R541 6.8g (7.8mmol, 수율 64%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R541 6.8g (7.8mmol, 64% yield).
GC-Mass (이론치: 871.06g/mol, 측정치: 871g/mol)GC-Mass (Theoretical value: 871.06 g / mol, Measured value: 871 g / mol)
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합성예Synthesis Example
14] R551의 합성 14] Synthesis of R551
질소 기류 하에서 A8 9.8g (11.8mmol), 3-chloro-1,8-diphenylthieno[3,2-f]quinazoline 4.3g (13.0mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.4g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.9.8 g (11.8 mmol), 3-chloro-1,8-diphenylthieno [3,2-f] quinazoline 4.3 g (13.0 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R551 8.4g (7.2mmol, 수율 61%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R551 8.4g (7.2mmol, 61% yield).
GC-Mass (이론치: 1164.38g/mol, 측정치: 1164g/mol)GC-Mass (Theoretical value: 1164.38 g / mol, Measured value: 1164 g / mol)
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합성예Synthesis Example
15] R141의 합성 15] Synthesis of R141
질소 기류 하에서 A9 5.4g (11.8mmol), 7-chloro-2,9-diphenylthieno[2,3-f]quinazoline 4.2g (13.0mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.4g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.4 g (11.8 mmol) A7, 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline 4.2 g (13.0 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R141 5.7g (7.2mmol, 수율 61%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R141 5.7g (7.2mmol, 61% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
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합성예Synthesis Example
16] R241의 합성 16] Synthesis of R241
질소 기류 하에서 A10 5.4g (11.8mmol), 7-chloro-2,9-diphenylthieno[2,3-f]quinazoline 4.8g (13.0mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.4g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.4 g (11.8 mmol) of A10, 4.8 g (13.0 mmol) of 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline, Pd 2 (dba) 3 0.6 g (5 mol%), under nitrogen stream - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R241 5.7g (7.2mmol, 수율 61%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R241 5.7g (7.2mmol, 61% yield).
GC-Mass (이론치: 794.96g/mol, 측정치: 794g/mol)GC-Mass (Theoretical value: 794.96 g / mol, Measured value: 794 g / mol)
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합성예Synthesis Example
17] R556의 합성 17] Synthesis of R556
질소 기류 하에서 A11 8.9g (12.7mmol), 3-chloro-1,8-diphenylthieno[3,2-f]quinazoline 4.6g (13.9mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.6g (38.0mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.8.9 g (12.7 mmol), 3-chloro-1,8-diphenylthieno [3,2-f] quinazoline 4.6 g (13.9 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R556 7.7g (7.7mmol, 수율 61%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R556 7.7g (7.7mmol, 61% yield).
GC-Mass (이론치: 999.19g/mol, 측정치: 999g/mol)GC-Mass (Theoretical value: 999.19 g / mol, Measured value: 999 g / mol)
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합성예Synthesis Example
18] R561의 합성 18] Synthesis of R561
질소 기류 하에서 A1 5.6g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.1g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1 g (13.4 mmol), Pd 2 (dba) 3 0.6 g under nitrogen stream put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R561 6.4g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R561 6.4g (7.9mmol, 65% yield).
GC-Mass (이론치: 804.98g/mol, 측정치: 804g/mol)GC-Mass (Theoretical value: 804.98 g / mol, Measured value: 804 g / mol)
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합성예Synthesis Example
19] R567의 합성 19] Synthesis of R567
질소 기류 하에서 A1 5.6g (12.1mmol), 3-chloro-1,8-diphenylfuro[3,2-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1 under nitrogen stream, 4.8 g (13.4 mmol) 3-chloro-1,8-diphenylfuro [3,2-f] quinazoline, Pd 2 (dba) 3 0.6 g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R567 6.0g (7.7mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R567 6.0g (7.7mmol, 63% yield).
GC-Mass (이론치: 778.90g/mol, 측정치: 778g/mol)GC-Mass (Theoretical value: 778.90g / mol, Measured value: 778g / mol)
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합성예20Synthesis Example 20
] R571의 합성Synthesis of R571
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-1,2,9-triphenyl-1H-pyrrolo[2,3-f]quinazoline 5.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 7-chloro-1,2,9-triphenyl-1H-pyrrolo [2,3-f] quinazoline 5.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R571 6.4g (7.5mmol, 수율 62%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R571 6.4g (7.5mmol, 62% yield).
GC-Mass (이론치: 854.01g/mol, 측정치: 854g/mol)GC-Mass (Theoretical value: 854.01 g / mol, Measured value: 854 g / mol)
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합성예Synthesis Example
21] R581의 합성 21] Synthesis of R581
질소 기류 하에서 A12 5.0g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.1g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1 g (13.4 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R581 6.1g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R581 6.1g (7.9mmol, 65% yield).
GC-Mass (이론치: 775.94g/mol, 측정치: 775g/mol)GC-Mass (Theoretical value: 775.94 g / mol, Measured value: 775 g / mol)
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합성예Synthesis Example
22] R582의 합성 22] Synthesis of R582
질소 기류 하에서 A12 5.0g (12.1mmol), 7-chloro-2,9-diphenylfuro[2,3-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol), 7-chloro-2,9-diphenylfuro [2,3-f] quinazoline 4.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R582 5.6g (7.7mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R582 5.6g (7.7mmol, 63% yield).
GC-Mass (이론치: 729.86g/mol, 측정치: 729g/mol)GC-Mass (Theoretical value: 729.86 g / mol, Measured value: 729 g / mol)
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합성예23Synthesis Example 23
] R583의 합성Synthesis of R583
질소 기류 하에서 A12 5.0g (12.1mmol), 7-chloro-1,2,9-triphenyl-1H-pyrrolo[2,3-f]quinazoline 5.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol) Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol) of A12, 7-chloro-1,2,9-triphenyl-1H-pyrrolo [2,3-f] quinazoline 5.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) Toluene 100ml and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R583 6.1g (7.5mmol, 수율 62%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R583 6.1g (7.5mmol, 62% yield).
GC-Mass (이론치: 804.98g/mol, 측정치: 804g/mol)GC-Mass (Theoretical value: 804.98 g / mol, Measured value: 804 g / mol)
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합성예Synthesis Example
24] R584의 합성 24] Synthesis of R584
질소 기류 하에서 A13 4.7g (11.8mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.0g (13.0mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.4g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.4.7 g (11.8 mmol) of A13, 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0 g (13.0 mmol), Pd 2 (dba) 3 0.6 g under nitrogen stream put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R584 5.7g (7.7mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R584 5.7g (7.7mmol, 65% yield).
GC-Mass (이론치: 745.93g/mol, 측정치: 745g/mol)GC-Mass (Theoretical value: 745.93 g / mol, Measured value: 745 g / mol)
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합성예Synthesis Example
25] R587의 합성 25] Synthesis of R587
질소 기류 하에서 A14 4.5g (11.8mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.0g (13.0mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.4g (35.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.4.5g (11.8mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0g (13.0mmol), Pd 2 (dba) 3 0.6g under nitrogen stream put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R587 5.6g (7.7mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R587 5.6g (7.7mmol, 65% yield).
GC-Mass (이론치: 729.86g/mol, 측정치: 729g/mol)GC-Mass (Theoretical value: 729.86 g / mol, Measured value: 729 g / mol)
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합성예Synthesis Example
26] R590의 합성 26] Synthesis of R590
질소 기류 하에서 A15 6.5g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.1g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.5g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1g (13.4mmol), Pd 2 (dba) 3 0.6g (under nitrogen stream) put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R590 6.9g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the target compound R590 6.9g (7.9mmol, 65% yield).
GC-Mass (이론치: 878.07g/mol, 측정치: 878g/mol)GC-Mass (Theoretical value: 878.07 g / mol, Measured value: 878 g / mol)
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합성예Synthesis Example
27] R593의 합성 27] Synthesis of R593
질소 기류 하에서 A16 5.2g (12.0mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.0g (13.2mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (35.9mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.2 g (12.0 mmol) of A16, 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0 g (13.2 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (35.9mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R593 6.1g (7.8mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R593 6.1g (7.8mmol, 65% yield).
GC-Mass (이론치: 778.00g/mol, 측정치: 778g/mol)GC-Mass (Theoretical value: 778.00g / mol, Measured value: 778g / mol)
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합성예Synthesis Example
28] R596의 합성 28] Synthesis of R596
질소 기류 하에서 A17 4.9g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.1g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.Under nitrogen stream, A17 4.9 g (12.1 mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1 g (13.4 mmol), Pd 2 (dba) 3 0.6 g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R596 5.9g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R596 5.9g (7.9mmol, 65% yield).
GC-Mass (이론치: 745.85g/mol, 측정치: 745g/mol)GC-Mass (Theoretical value: 745.85 g / mol, Measured value: 745 g / mol)
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합성예Synthesis Example
29] R599의 합성 29] Synthesis of R599
질소 기류 하에서 A18 6.1g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta[f]quinazoline 5.1g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.6.1g (12.1mmol), 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1g (13.4mmol), Pd 2 (dba) 3 0.6g under nitrogen stream put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R599 6.7g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R599 6.7g (7.9mmol, 65% yield).
GC-Mass (이론치: 847.06g/mol, 측정치: 847g/mol)GC-Mass (Theoretical value: 847.06 g / mol, Measured value: 847 g / mol)
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합성예Synthesis Example
30] R608의 합성 30] Synthesis of R608
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-1,9-diphenyl-1H-pyrazolo[3,4-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 7-chloro-1,9-diphenyl-1 H-pyrazolo [3,4-f] quinazoline 4.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g (5 mol) put%), tri- tert -butylphosphine 0.1g ( 0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R608 6.1g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R608 6.1g (7.9mmol, 65% yield).
GC-Mass (이론치: 778.90g/mol, 측정치: 778g/mol)GC-Mass (Theoretical value: 778.90g / mol, Measured value: 778g / mol)
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합성예Synthesis Example
31] R611의 합성 31] Synthesis of R611
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-2,9-diphenyloxazolo[4,5-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 7-chloro-2,9-diphenyloxazolo [4,5-f] quinazoline 4.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R611 6.2g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give 6.2 g (7.9 mmol, Yield 65%) of the target compound R611.
GC-Mass (이론치: 779.88g/mol, 측정치: 799g/mol)GC-Mass (Theoretical value: 779.88 g / mol, Measured value: 799 g / mol)
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합성예Synthesis Example
32] R614의 합성 32] Synthesis of R614
질소 기류 하에서 A1 5.6g (12.1mmol), 7-chloro-1,2,9-triphenyl-1H-imidazo[4,5-f]quinazoline 5.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.6 g (12.1 mmol) A1, 7-chloro-1,2,9-triphenyl-1 H-imidazo [4,5-f] quinazoline 5.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R614 6.8g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R614 6.8g (7.9mmol, 65% yield).
GC-Mass (이론치: 854.99g/mol, 측정치: 854g/mol)GC-Mass (Theoretical value: 854.99g / mol, Measured value: 854g / mol)
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합성예Synthesis Example
33] R615의 합성 33] Synthesis of R615
질소 기류 하에서 A12 5.0g (12.1mmol), 7-chloro-1,9-diphenyl-1H-pyrazolo[3,4-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol) of A12, 7-chloro-1,9-diphenyl-1H-pyrazolo [3,4-f] quinazoline 4.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g (5 mol) put%), tri- tert -butylphosphine 0.1g ( 0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R615 5.8g (7.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R615 5.8g (7.9mmol, 65% yield).
GC-Mass (이론치: 729.87g/mol, 측정치: 729g/mol)GC-Mass (Theoretical value: 729.87 g / mol, Measured value: 729 g / mol)
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합성예Synthesis Example
34] R616의 합성 34] Synthesis of R616
질소 기류 하에서 A12 5.0g (12.1mmol), 7-chloro-2,9-diphenyloxazolo[4,5-f]quinazoline 4.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol), 7-chloro-2,9-diphenyloxazolo [4,5-f] quinazoline 4.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R616 5.6g (7.7mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R616 5.6g (7.7mmol, 63% yield).
GC-Mass (이론치: 730.85g/mol, 측정치: 730g/mol)GC-Mass (Theoretical value: 730.85 g / mol, Measured value: 730 g / mol)
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합성예Synthesis Example
35] R617의 합성 35] Synthesis of R617
질소 기류 하에서 A12 5.0g (12.1mmol), 7-chloro-1,2,9-triphenyl-1H-imidazo[4,5-f]quinazoline 5.8g (13.4mmol), Pd2(dba)3 0.6g (5 mol%), tri-tert-butylphosphine 0.1g (0.6mmol) 및 Sodium tert-butoxide 3.5g (36.4mmol)와 Toluene 100ml를 넣고 110℃에서 4시간 동안 교반하였다.5.0 g (12.1 mmol) of A12, 7-chloro-1,2,9-triphenyl-1H-imidazo [4,5-f] quinazoline 5.8 g (13.4 mmol), Pd 2 (dba) 3 0.6 g put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R617 6.1g (7.5mmol, 수율 62%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to give the title compound R617 6.1g (7.5mmol, 62% yield).
GC-Mass (이론치: 805.96g/mol, 측정치: 805g/mol)GC-Mass (Theoretical value: 805.96 g / mol, Measured value: 805 g / mol)
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합성예Synthesis Example
36] R621의 합성 36] Synthesis of R621
질소 기류 하에서 A19 9.2g (12.1 mmol), 7-bromo-2,9-diphenylthieno[2,3-f]quinazoline 6.1g (14.5 mmol), Pd(PPh3)4 0.7g (5 mol%) 및 potassium carbonate 7.0g (36.3 mmol)를 Toluene/H2O/Ethanol 80ml/40ml/40ml에 넣고 110℃에서 3시간 동안 교반하였다.9.19 g (12.1 mmol) of A19, 6.1 g (14.5 mmol) of 7-bromo-2,9-diphenylthieno [2,3-f] quinazoline, 0.7 g (5 mol%) of Pd (PPh 3 ) 4 and potassium under nitrogen stream 7.0 g (36.3 mmol) of carbonate was added to 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R621 (9.1g, 8.7mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound R621 (9.1g, 8.7mmol, 72% yield).
GC-Mass (이론치: 1049.25g/mol, 측정치: 1049g/molGC-Mass (Theoretical value: 1049.25 g / mol, Measured value: 1049 g / mol
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합성예Synthesis Example
37] R622의 합성 37] Synthesis of R622
질소 기류 하에서 A19 7.8g (11.8 mmol), 7-bromo-2,9-diphenylthieno[2,3-f]quinazoline 5.9g (14.2 mmol), Pd(PPh3)4 0.7g (5 mol%) 및 potassium carbonate 4.9g (35.4 mmol)를 Toluene/H2O/Ethanol 80ml/40ml/40ml에 넣고 110℃에서 3시간 동안 교반하였다.7.8 g (11.8 mmol) of A19, 5.9 g (14.2 mmol) of 7-bromo-2,9-diphenylthieno [2,3-f] quinazoline, 0.7 g (5 mol%) of Pd (PPh 3 ) 4 and potassium under nitrogen stream 4.9 g (35.4 mmol) of carbonate was added to 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R622 (8.1g, 8.5mmol, 수율 72%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound R622 (8.1g, 8.5mmol, 72% yield).
GC-Mass (이론치: 950.16g/mol, 측정치: 950g/mol)GC-Mass (Theoretical value: 950.16 g / mol, Measured value: 950 g / mol)
[[
실시예Example
1 내지 32] 적색 유기 1 to 32] red organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically washed with distilled water glass substrate coated with a thin film of 1500 증류 thickness. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/90% 합성예 1 내지 30, 36, 37의 각각의 화합물 + 10% (piq)2Ir(acac) (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / 90% of each compound of Synthesis Examples 1 to 30, 36 and 37 + 10% (piq) 2 Ir (acac) (300 nm) on the thus prepared ITO transparent electrode / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.
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비교예Comparative example
1] One]
발광 호스트 물질로서 화합물 R41 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 1과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R41 as the light emitting host material.
[[
비교예Comparative example
2] 2]
발광 호스트 물질로서 화합물 R41 대신 D1을 사용하는 것을 제외하고는 상기 실시예 1과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 1, except that D1 was used instead of the compound R41 as the light emitting host material.
사용된 m-MTDATA, TCTA, (piq)2Ir(acac), BCP, Alq3, CBP 및 D1의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, (piq) 2 Ir (acac), BCP, Alq 3 , CBP and D1 used are as follows.
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평가예Evaluation example
1] One]
실시예 1 내지 32, 비교예 1 및 2에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 발광피크 및 전류효율을 측정하고, 그 결과를 하기 표 1에 나타내었다.For each organic electroluminescent device fabricated in Examples 1 to 32 and Comparative Examples 1 and 2, the driving voltage, the light emission peak, and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. It was.
| 샘플Sample | 발광층 호스트Light emitting layer host | 구동전압 (V)Drive voltage (V) | 발광피크 (nm)Luminous peak (nm) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | R41R41 | 4.04.0 | 621621 | 16.516.5 |
| 실시예 2Example 2 | R42R42 | 4.14.1 | 621621 | 16.416.4 |
| 실시예 3Example 3 | R43R43 | 4.14.1 | 621621 | 17.817.8 |
| 실시예 4Example 4 | R44R44 | 4.34.3 | 621621 | 17.217.2 |
| 실시예 5Example 5 | R45R45 | 4.34.3 | 621621 | 16.516.5 |
| 실시예 6Example 6 | R57R57 | 4.34.3 | 621621 | 17.417.4 |
| 실시예 7Example 7 | R381R381 | 4.24.2 | 621621 | 17.817.8 |
| 실시예 8Example 8 | R383R383 | 4.54.5 | 621621 | 17.117.1 |
| 실시예 9Example 9 | R384R384 | 4.44.4 | 621621 | 17.117.1 |
| 실시예 10Example 10 | R397R397 | 4.34.3 | 621621 | 16.316.3 |
| 실시예 11Example 11 | R399R399 | 4.24.2 | 621621 | 17.117.1 |
| 실시예 12Example 12 | R542R542 | 4.64.6 | 621621 | 15.815.8 |
| 실시예 13Example 13 | R541R541 | 4.24.2 | 621621 | 15.815.8 |
| 실시예 14Example 14 | R551R551 | 4.54.5 | 621621 | 15.915.9 |
| 실시예 15Example 15 | R141R141 | 4.14.1 | 621621 | 16.316.3 |
| 실시예 16Example 16 | R241R241 | 4.24.2 | 621621 | 18.718.7 |
| 실시예 17Example 17 | R556R556 | 4.34.3 | 621621 | 17.217.2 |
| 실시예 18Example 18 | R561R561 | 4.44.4 | 621621 | 16.316.3 |
| 실시예 19Example 19 | R567R567 | 4.14.1 | 621621 | 18.718.7 |
| 실시예 20Example 20 | R571R571 | 4.24.2 | 621621 | 19.219.2 |
| 실시예 21Example 21 | R581R581 | 3.03.0 | 621621 | 15.915.9 |
| 실시예 22Example 22 | R582R582 | 3.13.1 | 621621 | 17.517.5 |
| 실시예 23Example 23 | R583R583 | 3.33.3 | 621621 | 15.915.9 |
| 실시예 24Example 24 | R584R584 | 3.53.5 | 621621 | 15.215.2 |
| 실시예 25Example 25 | R587R587 | 3.23.2 | 621621 | 16.716.7 |
| 실시예 26Example 26 | R590R590 | 3.53.5 | 623623 | 15.315.3 |
| 실시예 27Example 27 | R593R593 | 3.13.1 | 621621 | 16.216.2 |
| 실시예 28Example 28 | R596R596 | 3.03.0 | 621621 | 16.116.1 |
| 실시예 29Example 29 | R599R599 | 3.23.2 | 621621 | 17.317.3 |
| 실시예 30Example 30 | R608R608 | 3.33.3 | 621621 | 15.115.1 |
| 실시예 31Example 31 | R621R621 | 3.53.5 | 621621 | 16.316.3 |
| 실시예 32Example 32 | R622R622 | 3.63.6 | 621621 | 15.515.5 |
| 비교예 1Comparative Example 1 | CBPCBP | 5.75.7 | 622622 | 9.29.2 |
| 비교예 2Comparative Example 2 | D1D1 | 4.24.2 | 622622 | 14.714.7 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 적색 유기 전계 발광 소자의 발광층 재료로 사용한 경우(실시예 1 내지 32)가 종래 CBP를 적색 유기 전계 발광 소자의 발광층 재료로 사용한 경우(비교예 1)에 비해 효율 및 구동전압이 우수한 것을 알 수 있었고, D1을 적색 유기 전계 발광 소자의 발광층 재료로 사용한 경우(비교예 2)에 비해 효율이 우수한 것을 알 수 있었다.As shown in Table 1 above, when the compound according to the present invention was used as the light emitting layer material of the red organic electroluminescent device (Examples 1 to 32), when the conventional CBP was used as the light emitting layer material of the red organic electroluminescent device (Comparative Example) It was found that the efficiency and the driving voltage were superior to those of 1), and that the efficiency was superior to that of the case where D1 was used as the light emitting layer material of the red organic EL device (Comparative Example 2).
[[
실시예Example
33 내지 36] 유기 33 to 36] organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 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 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was ultrasonically cleaned with distilled water. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out. The substrate was then transferred to a vacuum depositor.
상기와 같이 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/ 합성예 4, 25, 26, 28의 각각의 화합물 (80 nm)/DS-H522(㈜두산전자) + 5% DS-501(㈜두산전자) (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순서로 유기 전계 발광 소자를 제조하였다.M-MTDATA (60 nm) / Compounds 4, 25, 26, 28 of Compound (80 nm) / DS-H522 (Doosan Electronics Co., Ltd.) + 5% DS-501 Doosan Electronics) (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to prepare an organic EL device.
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비교예Comparative example
3] 3]
정공 수송층 물질로 사용된 화합물 R44 대신 NPB를 사용하는 것을 제외하고는 실시예 33과 동일한 과정으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 33, except that NPB was used instead of the compound R44 used as the hole transport layer.
사용된 NPB의 구조는 하기와 같다.The structure of the NPB used is as follows.
[[
평가예Evaluation example
2] 2]
실시예 33 내지 36, 비교예 4에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each organic electroluminescent device manufactured in Examples 33 to 36 and Comparative Example 4, the driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
| 샘플Sample | 정공 수송층Hole transport layer | 구동 전압 (V)Driving voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 33Example 33 | R44R44 | 2.92.9 | 22.222.2 |
| 실시예 34Example 34 | R587R587 | 3.03.0 | 24.524.5 |
| 실시예 35Example 35 | R590R590 | 3.63.6 | 36.836.8 |
| 실시예 36Example 36 | R596R596 | 3.93.9 | 34.834.8 |
| 비교예 3Comparative Example 3 | NPBNPB | 5.35.3 | 18.018.0 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 유기 전계 발광 소자의 정공 수송층 재료로 사용한 경우(실시예 33 내지 36)가 종래 NPB를 사용한 유기 전계 발광 소자의 정공 수송층 재료로 사용한 경우(비교예 3)에 비해 효율 및 구동전압이 우수한 것을 알 수 있었다.As shown in Table 2 above, when the compound according to the present invention was used as the hole transporting layer material of the organic electroluminescent device (Examples 33 to 36), it was used as the hole transporting layer material of the organic electroluminescent device using conventional NPB (comparatively). It was found that the efficiency and the driving voltage were superior to those of Example 3).
[[
실시예Example
37 내지 43] 유기 37 to 43] organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205(㈜두산전자) (80 nm)/NPB (15 nm)/ADN + 5% DS-405(㈜두산전자) (30 nm)/ 합성예 1, 18, 31 내지 35의 각각의 화합물 (80 nm) /LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the prepared ITO transparent electrode, DS-205 (Doosan Electronics Co., Ltd.) (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / Synthesis Examples 1, 18 , 31 to 35 each compound (80 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.
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비교예Comparative example
4] 유기 4] organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
전자 수송층의 물질로 사용된 화합물 R41 대신 Alq3을 사용하여 30 nm로 증착하는 것을 제외하고는 실시예 37과 동일한 과정으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 37, except for depositing at 30 nm using Alq 3 instead of the compound R41 used as the material of the electron transporting layer.
사용된 ADN의 구조는 하기와 같다.The structure of ADN used is as follows.
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평가예Evaluation example
3] 3]
실시예 37 내지 43, 비교예 4에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 3에 나타내었다.For the organic electroluminescent devices manufactured in Examples 37 to 43 and Comparative Example 4, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.
| 샘플Sample | 전자 수송층Electron transport layer | 구동전압 (V)Drive voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) | 발광피크 (nm)Luminous peak (nm) |
| 실시예 37Example 37 | R41R41 | 2.82.8 | 9.99.9 | 458458 |
| 실시예 38Example 38 | R561R561 | 2.92.9 | 9.89.8 | 458458 |
| 실시예 39Example 39 | R611R611 | 3.03.0 | 9.99.9 | 458458 |
| 실시예 40Example 40 | R614R614 | 3.13.1 | 10.610.6 | 458458 |
| 실시예 41Example 41 | R615R615 | 3.43.4 | 11.811.8 | 458458 |
| 실시예 42Example 42 | R616R616 | 3.53.5 | 12.312.3 | 458458 |
| 실시예 43Example 43 | R617R617 | 3.43.4 | 13.213.2 | 458458 |
| 비교예 4Comparative Example 4 | Alq3 Alq 3 | 5.25.2 | 5.45.4 | 458458 |
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물을 유기 전계 발광 소자의 전자 수송층 재료로 사용한 경우(실시예 38 내지 43)가 종래 Alq3를 사용한 유기 전계 발광 소자의 정공 수송층 재료로 사용한 경우(비교예 4)에 비해 효율 및 구동전압이 우수한 것을 알 수 있었다.As shown in Table 3 above, when the compound according to the present invention was used as an electron transporting layer material of an organic electroluminescent device (Examples 38 to 43), it was used as a hole transporting layer material of an organic electroluminescent device using conventional Alq 3 ( It was found that the efficiency and the driving voltage were superior to those of Comparative Example 4).
Claims (10)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,A는 N, O, S 중 하나 이상의 원자를 함유 또는 비함유하는 5원 고리이고,A is a 5-membered ring containing or not containing one or more atoms of N, O, S,B는 6원 방향족 고리이고,B is a 6 membered aromatic ring,Ar1은 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,Ar 1 is selected from the group consisting of hydrogen, a C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms,L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C60의 아릴렌기 및 핵원자수 5 내지 60의 헤테로아릴렌기로 이루어진 군에서 선택되며, 이때 L1은 X1, X2, Y1 내지 Y4 중 어느 하나의 탄소 또는 질소와 연결되고,L 1 and L 2 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of a C 6 ~ C 60 arylene group and a heteroarylene group having 5 to 60 nuclear atoms, wherein L 1 is Connected to carbon or nitrogen of any one of X 1 , X 2 , Y 1 to Y 4 ,X1은 NR1 또는 CR2R3이고,X 1 is NR 1 or CR 2 R 3 ,X2 내지 X4는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 S, O, NR4 및 CR5R6로 이루어진 군에서 선택되고, 이때 X2 및 X4 중 하나 이상은 단일결합이며, X3 및 X4가 모두 단일결합인 경우는 제외하고,X 2 to X 4 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of S, O, NR 4 and CR 5 R 6 , wherein at least one of X 2 and X 4 is a single bond Except that X 3 and X 4 are both single bonds,Y1 내지 Y8 및 Y11 내지 Y18은 각각 독립적으로 CR7이고, 이때 복수의 R7는 서로 동일하거나 상이하며,Y 1 to Y 8 and Y 11 to Y 18 are each independently CR 7, wherein a plurality of R 7 are the same as or different from each other,R1 내지 R7는 서로 동일하거나 상이하며, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되거나, 혹은 인접한 기와 결합하여 축합 방향족 고리 또는 축합 헤테로방향족 고리를 형성하며,R 1 to R 7 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms, or a condensed aromatic ring in combination with an adjacent group Or to form a condensed heteroaromatic ring,상기 A의 5원 고리와, B의 6원 방향족 고리와, 상기 Ar1의 아릴기, 헤테로아릴기와, 상기 L1 및 L2의 아릴렌기, 헤테로아릴렌기와, 상기 R1 내지 R7의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The 5-membered ring of A, the 6-membered aromatic ring of B, the aryl group and heteroaryl group of Ar 1, the arylene group and heteroarylene group of L 1 and L 2 , and the aryl of R 1 to R 7 The group and heteroaryl group are each independently deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ aryl of C 60 silyl group, C 2 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, and a C 6 ~ C 60 It may be substituted with one or more substituents selected from the group consisting of an arylamine group, wherein when the substituents are plural, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 5 중 어느 하나로 표시되는 것인 화합물.Compound represented by Formula 1 is represented by any one of the following formulas 2 to 5.[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
상기 화학식 2 내지 5에서,In Chemical Formulas 2 to 5,A, B, Ar1 , L2, X1 내지 X4, Y1 내지 Y8, Y11 내지 Y18은 제1항에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 1 to X 4 , Y 1 to Y 8 , and Y 11 to Y 18 are as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 8 중 어느 하나로 표시되는 것인 화합물.Compound represented by Formula 1 is represented by any one of the following formulas 6 to 8.[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
상기 화학식 6 내지 8에서,In Chemical Formulas 6 to 8,A, B, Ar1 , L2, X3, X4, Y5 내지 Y8, Y11 내지 Y18은 제1항에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 3 , X 4 , Y 5 to Y 8 , Y 11 to Y 18 are as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 9 내지 11 중 어느 하나로 표시되는 것인 화합물.Compound represented by Formula 1 is represented by any one of the following formulas 9 to 11.[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
상기 화학식 9 내지 11에서,In Chemical Formulas 9 to 11,A, B, Ar1 , L2, X1, X2, Y5 내지 Y8, Y11 내지 Y18은 제1항에서 정의한 바와 같다.A, B, Ar 1 , L 2 , X 1 , X 2 , Y 5 to Y 8 , Y 11 to Y 18 are as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 화학식 1의(*는 화학식 1의 L1과 결합하는 부위를 의미함)는 하기 A-1 내지 A-18로 표시되는 치환체 중 어느 하나로 표시되는 것인 화합물.Of Formula 1
(* Means a site that binds to L 1 of Formula 1) is a compound represented by any one of the substituents represented by A-1 to A-18.
상기 A-1 내지 A-18에서,In the above A-1 to A-18,Ar1은 제1항에서 정의한 바와 같고,Ar 1 is as defined in claim 1,R8는 서로 동일하거나 상이하며, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되며,R 8 is the same as or different from each other, and each independently selected from hydrogen, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,상기 R8의 아릴기, 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The aryl group of said R 8, heteroaryl groups each independently selected from deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of the, C 6 Aryl group of ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 ~ C 40 , aryloxy group of C 6 ~ C 60 , alkylsilyl group of C 1 ~ C 40 , C 6 An arylsilyl group of ˜C 60 , an alkyl boron group of C 2 ˜C 40, an aryl boron group of C 6 ˜C 60 , an arylphosphine group of C 6 ˜C 60 , an arylphosphine oxide group of C 6 ˜C 60 , and It may be substituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylamine group, wherein when there are a plurality of the substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 A는 N, O, S 중 하나 이상의 원자를 함유 또는 비함유하는 5원 고리이고,A is a 5-membered ring containing or not containing one or more atoms of N, O, S,이때, 상기 A의 5원 고리는 하나 이상의 C6~C60의 아릴기로 치환되는 것인 화합물.Wherein the 5-membered ring of A is substituted with at least one C 6 -C 60 aryl group.
- 제1항에 있어서,The method of claim 1,상기 화학식 1의는 하기 B-1 내지 B-12로 표시되는 치환체 중 어느 하나로 표시되는 것인 화합물.Of Formula 1
Is represented by any one of substituents represented by B-1 to B-12.
상기 B-1 내지 B-12에서,In the above B-1 to B-12,R4 내지 R6는 제1항에서 정의한 바와 같다.R 4 to R 6 are as defined in claim 1. - 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode.상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제7항 중 어느 한 항에 기재된 화합물을 포함하는 것인 유기 전계 발광 소자.At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 7.
- 제8항에 있어서,The method of claim 8,상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층 및 발광층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.The organic material layer containing the compound is an organic electroluminescent device is selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.
- 제8항에 있어서,The method of claim 8,상기 화합물을 포함하는 유기물층은 인광 발광층인 유기 전계 발광 소자.The organic material layer containing the compound is an organic electroluminescent device which is a phosphorescent light emitting layer.
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