KR101776193B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR101776193B1 KR101776193B1 KR1020140188900A KR20140188900A KR101776193B1 KR 101776193 B1 KR101776193 B1 KR 101776193B1 KR 1020140188900 A KR1020140188900 A KR 1020140188900A KR 20140188900 A KR20140188900 A KR 20140188900A KR 101776193 B1 KR101776193 B1 KR 101776193B1
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 257
- 239000012044 organic layer Substances 0.000 claims abstract description 42
- 239000010410 layer Substances 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 description 117
- 238000003786 synthesis reaction Methods 0.000 description 114
- 238000002360 preparation method Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 24
- 125000001072 heteroaryl group Chemical group 0.000 description 24
- -1 metal complex compound Chemical class 0.000 description 23
- 125000004429 atom Chemical group 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 125000005264 aryl amine group Chemical group 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011368 organic material Substances 0.000 description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 9
- 125000005103 alkyl silyl group Chemical group 0.000 description 9
- 125000005104 aryl silyl group Chemical group 0.000 description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 0 *[n](c(cccc1)c1c1ccc2)c1c2-c1ccccc1 Chemical compound *[n](c(cccc1)c1c1ccc2)c1c2-c1ccccc1 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 6
- MMTJRYAVTQORAA-UHFFFAOYSA-N 6-chloro-1,3-diphenyl-9H-carbazole Chemical compound ClC=1C=C2C=3C=C(C=C(C3NC2=CC1)C1=CC=CC=C1)C1=CC=CC=C1 MMTJRYAVTQORAA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 229910052805 deuterium Inorganic materials 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- OTLJSDATRAVVAV-UHFFFAOYSA-N 4-chloro-2-iodo-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1I OTLJSDATRAVVAV-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- IBJIKRRZQJQUOD-UHFFFAOYSA-N 1,9-diphenylcarbazol-3-ol Chemical compound C1(=CC=CC=C1)C1=CC(=CC=2C3=CC=CC=C3N(C1=2)C1=CC=CC=C1)O IBJIKRRZQJQUOD-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- OCQFNQDUZYHBEQ-UHFFFAOYSA-N 6-chloro-1,4-diphenyl-9H-carbazole Chemical compound ClC=1C=C2C=3C(=CC=C(C=3NC2=CC=1)C1=CC=CC=C1)C1=CC=CC=C1 OCQFNQDUZYHBEQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 2
- NJNCTRAJEDSNPN-UHFFFAOYSA-N 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole Chemical compound C1(=CC=CC=C1)C1CCC(C=2C3=CC=CC=C3NC1=2)C1=CC=CC=C1 NJNCTRAJEDSNPN-UHFFFAOYSA-N 0.000 description 2
- ZHXYPKWBJAVWQD-UHFFFAOYSA-N 1,4-diphenyl-9h-carbazole Chemical compound C1=CC=CC=C1C(C=1NC2=CC=CC=C2C=11)=CC=C1C1=CC=CC=C1 ZHXYPKWBJAVWQD-UHFFFAOYSA-N 0.000 description 2
- KDCSNHMPUYHLHD-UHFFFAOYSA-N 1-chloro-3-methoxy-9-phenylcarbazole Chemical compound ClC1=CC(=CC=2C3=CC=CC=C3N(C1=2)C1=CC=CC=C1)OC KDCSNHMPUYHLHD-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- BDYZSJRWACUCOA-UHFFFAOYSA-N 3-methoxy-1,9-diphenylcarbazole Chemical compound COC=1C=C(C=2N(C3=CC=CC=C3C=2C=1)C1=CC=CC=C1)C1=CC=CC=C1 BDYZSJRWACUCOA-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- HFTOEQRHDMJDCO-UHFFFAOYSA-N Clc(cc1)cc(c2c3c(-c4ccccc4)ccc2-c2ccccc2)c1[n]3-c1ccccc1 Chemical compound Clc(cc1)cc(c2c3c(-c4ccccc4)ccc2-c2ccccc2)c1[n]3-c1ccccc1 HFTOEQRHDMJDCO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 150000001412 amines Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- CBLKFNHDNANUNU-UHFFFAOYSA-N n-(4-bromophenyl)-9,9-dimethyl-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(Br)C=C1 CBLKFNHDNANUNU-UHFFFAOYSA-N 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- 125000006751 (C6-C60) aryloxy group Chemical group 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
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-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
- ROXLTPRFYRUWBO-UHFFFAOYSA-N 1-(4-bromophenyl)-9,9-dimethylfluoren-2-amine Chemical compound BrC1=CC=C(C=C1)C1=C(C=CC=2C3=CC=CC=C3C(C1=2)(C)C)N ROXLTPRFYRUWBO-UHFFFAOYSA-N 0.000 description 1
- GJDSGEWWFYYOFU-UHFFFAOYSA-N 1-[1-(9h-carbazol-1-yl)-4-phenylcyclohexa-2,4-dien-1-yl]-9h-carbazole Chemical group C1=CC(C=2C3=C(C4=CC=CC=C4N3)C=CC=2)(C=2C3=C(C4=CC=CC=C4N3)C=CC=2)CC=C1C1=CC=CC=C1 GJDSGEWWFYYOFU-UHFFFAOYSA-N 0.000 description 1
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- DBDCPKPHHCECLZ-UHFFFAOYSA-N 1-chloro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Cl)=CC=C2 DBDCPKPHHCECLZ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- AOUCAPVHEWYHDZ-UHFFFAOYSA-N 9,9-dimethyl-1-(4-phenylphenyl)fluoren-2-amine Chemical compound C1(=CC=C(C=C1)C1=C(C=CC=2C3=CC=CC=C3C(C12)(C)C)N)C1=CC=CC=C1 AOUCAPVHEWYHDZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
본 발명은 내열성, 정공 수송능, 발광능 등이 우수한 신규 화합물을 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating a novel compound having excellent heat resistance, hole transporting ability, and light emitting performance into one or more organic layers.
Description
본 발명은 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device including the same.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이, 음극에서는 전자가 각각 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥 상태로 떨어질 때 빛이 나게 된다. 유기물층으로 사용되는 물질은 그 기능에 따라 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해서도 관심이 집중되고 있다. The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The dopant material can 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. The development of phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로사용되는 물질로는, NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히, 발광 물질 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 있고, 이들은 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq 3 and the like are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.
그러나 종래 발광 물질들은 발광 특성 측면에서 양호하나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질을 포함하는 유기 전계 발광 소자의 개발이 요구되고 있다. However, conventional luminescent materials are good in terms of luminescence characteristics, but have poor thermal stability due to low glass transition temperature, and thus are not satisfactory in terms of lifetime in organic EL devices. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.
한편, 유기 전계 발광 소자의 실용화 및 특성 향상을 위해서, 상기와 같은 다층 구조를 갖는 유기물층으로 소자를 구성할 뿐만 아니라 소자의 재료, 특히 정공 수송 물질은 열적 및 전기적으로 안정적인 특성을 가지고 있어야 한다. 왜냐하면, 소자에 전압을 인가하였을 때, 소자에서 발생되는 열로 인하여 열안정성이 낮은 분자는 결정 안정성이 낮아 재배열 현상이 일어나게 되고, 결국 국부적으로 결정화가 발생되어 불균질 부분이 존재함으로써, 전기장이 이 부분에 집중하게 되어 소자의 열화 및 파괴를 가져오기 때문이다. In addition, in order to realize practical use and improve the characteristics of the organic electroluminescent device, not only the device should be composed of the organic material layer having the multilayer structure, but also the material of the device, especially the hole transporting material, should have stable thermal and electrical characteristics. This is because, when a voltage is applied to a device, molecules having low thermal stability due to heat generated in the device have a low crystal stability and are rearranged. As a result, a localized crystallization occurs and an inhomogeneous portion exists. Thereby causing deterioration and destruction of the device.
따라서, 상기한 점을 고려하여 종래에 사용된 정공 수송 물질로는 m-MTDATA [4, 4',4"-트리스(N-3-메틸페닐-N-페닐아미노)-트리페닐아민, 2-TNATA [4, 4',4?-트리스(N-(나프틸렌-2-일)-N-페닐아미노)-트리페닐아민], TPD [N, N'-디페닐-N, N'-디(3-메틸페닐)-4, 4'-디아미노비페닐] 및 NPB [N, N'-디(나프탈렌-1-일)-N, N'-디페닐벤지딘] 등이 있다.Therefore, in consideration of the above-mentioned points, conventionally used hole transport materials include m-MTDATA [4,4 ', 4 "-tris (N-3- methylphenyl- Triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4,4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].
그러나, m-MTDATA 및 2-TNATA는 유리전이온도(Tg)가 각각 78 ℃ 및 108 ℃로 낮을 뿐만 아니라, 대량화하는 과정에서 많은 문제점이 발생하기 때문에 풀 칼라를 구현하는데 문제가 있었다. 한편, TPD 및 NPB도 유리전이온도(Tg)가 각각 60 ℃ 및 96 ℃로 낮기 때문에, 상기와 같은 이유로 소자의 수명을 단축시킨다는 치명적인 단점이 있었다. 따라서, 열안정성을 높일 수 있고, 우수한 정공 수송 능력을 가져 유기 전계 발광 소자의 발광효율 및 전력효율을 높일 수 있는 유기 전계 발광 소자의 개발이 요구되고 있다.However, since m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 ° C and 108 ° C, respectively, they cause problems in mass-production. On the other hand, since TPD and NPB have low glass transition temperatures (Tg) of 60 占 폚 and 96 占 폚, respectively, there is a fatal disadvantage that the lifetime of the device is shortened. Therefore, development of an organic electroluminescent device capable of increasing thermal stability and having an excellent hole transporting capability and capable of increasing the luminous efficiency and power efficiency of the organic electroluminescent device is desired.
본 발명은 전자 저지능, 정공 수송능 등이 모두 우수하여 발광층 재료, 발광 보조층 재료, 정공 수송층 재료로 사용될 수 있는 화합물을 제공하는 것을 목적으로 한다. An object of the present invention is to provide a compound which is excellent in both electron-blocking ability and hole-transporting ability and can be used as a light-emitting layer material, a light-emitting auxiliary layer material, and a hole transport layer material.
또한, 본 발명은 전술한 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 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 above-described novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by the following formula (1): < EMI ID =
(상기 화학식 1에서,(In the formula 1,
a는 0 내지 5의 정수이고; a is an integer from 0 to 5;
b는 0 내지 3의 정수이며; b is an integer from 0 to 3;
c는 0 내지 4의 정수이고;c is an integer from 0 to 4;
R1 내지 R4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 중수소, 할로겐, 시아노기, 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, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 치환기와 결합하여 축합 방향족환 또는 축합 헤테로방향족환을 형성할 수 있으며;R 1 to R 4 are the same or different and are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms , A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group , C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C of 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine An oxy group and an arylamine group of C 6 to C 60 , or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;
다만, R1 내지 R4 중 적어도 하나는 하기 화학식 2로 표시되는 치환체이고; Provided that at least one of R 1 to R 4 is a substituent represented by the following formula (2);
상기 화학식 2에서,In Formula 2,
*는 화학식 1의 R1 내지 R4 중 적어도 하나에 결합이 이루어지는 부위이고;* Is a moiety in which at least one of R 1 to R 4 in formula (1) is bonded;
L1은 단일 결합이거나, 또는 C6~C60의 아릴렌기 및 핵원자수 5 내지 60의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 is a single bond or a heteroarylene group having 5 to 60 ring atoms and an arylene group having 6 to 60 carbon atoms;
Ar1 및 Ar2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 및 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 Ar1 및 Ar2가 서로 결합하여 환을 형성할 수 있으며,Ar 1 and Ar 2 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms and a C 6 to C 60 And Ar 1 and Ar 2 may be bonded to each other to form a ring,
Ar1 내지 Ar2의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기, R1 내지 R4의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴아민기, 및 L1의 아릴렌기, 헤테로아릴렌기는 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, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 1종 이상으로 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 또는 상이함).Alkyl group of Ar 1 to Ar 2, an aryl group, a heteroaryl group and an arylamine group, R 1 to the alkyl group of R 4, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heteroarylene group of L 1 may be deuterium, halogen, cyano, C 1 - a C 40 alkyl group, C 3 ~ C 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 of the cycloalkyl of the alkyl group, the number of nuclear atoms of 3 to 40 heteroaryl group, C 1 ~ C 40 C 6 -C 60 aryloxy groups, C 1 -C 40 alkylsilyl groups, C 6 -C 60 arylsilyl groups, C 1 -C 40 alkylboron groups, C 6 -C 60 the arylboronic group, C 6 ~ C 60 aryl phosphine value as pingi, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ at least one selected from the group consisting of aryl amine group of C 60 Substituted or unsubstituted, and, if the beach, where the substituent of the plurality, all of which are the same or different from each other).
또, 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 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers is a compound And an organic electroluminescent device.
일례에 따르면, 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층은 정공 수송층, 발광보조층 및 발광층으로 이루어진 군에서 선택된다. According to an example, the one or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a hole transport layer, a light emitting auxiliary layer, and a light emitting layer.
본 발명의 유기 전계 발광 소자는 내열성, 발광능, 정공 수송능 등이 우수한 화합물을 적어도 1층 이상의 유기물층에 포함하기 때문에, 발광 성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 나아가 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.Since the organic electroluminescent device of the present invention includes at least one organic compound layer having excellent heat resistance, light emitting ability and hole transporting ability in at least one organic layer, aspects such as light emitting performance, driving voltage, lifetime and efficiency can be greatly improved, And can be effectively applied to a full color display panel and the like.
이하, 본 발명에 대해 설명한다.Hereinafter, the present invention will be described.
본 발명에 따른 화합물은 카바졸의 1번 위치에 페닐기가 도입된 페닐카바졸 모이어티의 기본 골격에, 상기 페닐기 부분, 카바졸의 양(兩) 벤젠 부분 중 하나 및 카바졸의 질소 부분 중 어느 하나에 아릴아민기-함유 치환체가 도입되어 있는 구조로서, 상기 화학식 1로 표시되는 것을 특징으로 한다. 여기서, 카바졸의 위치 번호는 하기와 같이 나타낼 수 있다.The compound according to the present invention is characterized in that the phenyl skeleton of the phenylcarbazole moiety to which the phenyl group is introduced at the 1-position of the carbazole is bonded to the basic skeleton of the phenyl group moiety, either of the two benzene moieties of the carbazole and the nitrogen moiety of the carbazole And a structure in which an arylamine group-containing substituent is introduced into one molecule, which is characterized by being represented by the above formula (1). Here, the position number of the carbazole can be represented as follows.
본 발명에 따른 화합물은 카바졸의 1번 위치에 페닐기가 도입됨으로써, 화합물 분자가 뒤틀리고, 이로 인해 파이파이-스태킹(π-π-stacking)으로 인한 발광 특성 저하 문제가 발생되지 않는다. 따라서, 본 발명의 화합물은 여기 이합체(엑사이머, excimer)의 형성이 방지됨으로써, OLED의 발광 효율을 향상시킬 수 있다. 또한, 본 발명의 화합물은 카바졸의 1번 위치에 페닐기가 도입됨으로써, 페닐기가 도입되지 않은 카바졸 화합물에 비해 증착 온도가 낮기 때문에, 분자의 열안정성이 강화될 수 있다.In the compound according to the present invention, the compound molecule is distorted by introducing the phenyl group into the 1-position of the carbazole, so that there is no problem of lowering the luminescence property due to pi-pi-stacking. Therefore, the compound of the present invention can prevent the formation of an exciton excimer (excimer), thereby improving the luminous efficiency of the OLED. In addition, since the compound of the present invention has a lower deposition temperature than that of a carbazole compound into which a phenyl group is not introduced by introducing a phenyl group into the 1-position of the carbazole, the thermal stability of the molecule can be enhanced.
또, 발광층은 일반적으로 색순도와 발광효율을 증가시키기 위해 호스트 및 도펀트를 포함한다. 이때, 호스트 물질은 호스트의 삼중항 에너지 갭이 도펀트보다 높아야 한다. 특히, 도펀트가 효과적인 인광 발광을 제공하기 위해서는 호스트의 가장 낮은 여기 상태가 도펀트의 가장 낮은 방출 상태보다 에너지가 더 높아야한다. 그런데, 본 발명의 화합물에서 페닐카바졸 모이어티는 넓은 일중항 에너지 준위와 높은 삼중항 에너지 준위를 갖는다. 따라서, 본 발명의 화합물이 발광층의 호스트로 적용될 경우, 도펀트보다 높은 에너지 준위를 나타낼 수 있기 때문에, OLED의 발광 성능이 향상될 수 있다. In addition, the light emitting layer generally includes a host and a dopant to increase color purity and luminous efficiency. At this time, the host material should have a higher triplet energy gap than the dopant in the host. In particular, in order for the dopant to provide effective phosphorescence, the lowest excitation state of the host should be higher energy than the lowest emission state of the dopant. However, in the compounds of the present invention, the phenylcarbazole moiety has a broad singlet energy level and a high triplet energy level. Therefore, when the compound of the present invention is applied as a host of the light emitting layer, the light emitting performance of the OLED can be improved because it can exhibit a higher energy level than the dopant.
또한, 본 발명의 화합물은 전술한 바와 같이 높은 삼중항 에너지 갭을 갖기 때문에, 발광층에서 생성된 엑시톤(exciton)이 인접하는 정공수송층으로 확산(이동)되는 것을 방지할 수 있다. 따라서, 본 발명의 화합물을 이용하여 정공 수송층과 발광층 사이에 유기물층(이하, "발광 보조층"이라 함)을 형성할 경우, 상기 화합물에 의해 엑시톤의 확산이 방지되기 때문에, 상기 발광 보조층을 포함하지 않은 종래 유기 전계 발광 소자와 달리, 실질적으로 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있다.In addition, since the compound of the present invention has a high triplet energy gap as described above, the excitons generated in the light emitting layer can be prevented from diffusing (moving) into the adjacent hole transporting layer. Therefore, when the organic compound layer (hereinafter referred to as "light-emission-assisting layer") is formed between the hole transporting layer and the light-emitting layer using the compound of the present invention, the diffusion of the excitons is prevented by the compound, Unlike a conventional organic electroluminescent device, the number of the excitons contributing to light emission in the light emitting layer substantially increases, and the light emitting efficiency of the device can be improved.
아울러, 아릴아민기 및 카바졸기는 모두 전자 공여성이 큰 전자 주는 기(electron donating group, EDG)로서, 열적으로 안정하면서도 정공 이동도가 우수한 특성이 있다. 따라서, 아릴아민기-함유 치환체 및 카바졸 모이어티를 포함하고 있는 본 발명의 화합물은 열적 안정성이 우수하고, 정공 이동도도 높기 때문에, OLED의 정공 수송성 재료로 사용할 경우, 소자의 성능이 향상될 수 있다. In addition, both the arylamine group and the carbazole group are electron donating groups (EDGs), which are thermally stable and have excellent hole mobility. Therefore, the compound of the present invention containing an arylamine group-containing substituent and a carbazole moiety has excellent thermal stability and high hole mobility, so that when the compound is used as a hole transporting material of an OLED, .
게다가, 본 발명의 화학식 1로 표시되는 화합물은 상기 기본 골격에 다양한 치환체가 도입됨으로써, 화합물의 분자량이 유의적으로 증대되고, 따라서 유리전이온도가 향상됨에 따라 종래의 CBP(4,4-dicarbazolybiphenyl)보다 높은 열적 안정성을 나타낸다. 또한, 본 발명의 화합물은 유기물층의 결정화 억제에도 효과가 있다.In addition, since the compound represented by the formula (1) of the present invention introduces various substituents into the basic skeleton, the molecular weight of the compound is significantly increased, and thus the glass transition temperature is improved. Therefore, the conventional CBP (4,4-dicarbazolylbiphenyl) And exhibits higher thermal stability. Further, the compound of the present invention is also effective in inhibiting crystallization of the organic material layer.
이와 같이, 본 발명의 화합물을 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료, 정공 수송층 재료, 발광 보조층 재료로 적용할 경우, 유기 전계 발광 소자의 성능 및 수명 특성이 크게 향상될 수 있다. 이러한 유기 전계 발광 소자는 결과적으로 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.
Thus, when the compound of the present invention is applied to an organic material layer of an organic electroluminescent device, preferably a light emitting layer material, a hole transporting layer material, or a light emitting auxiliary layer material, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved . Such an organic electroluminescent device can consequently maximize the performance of a full-color organic luminescent panel.
본 발명에 따른 화학식 1에 있어서, a가 0인 경우, 수소가 치환기 R1으로 치환되지 않는 것을 의미하고, 상기 a가 1 내지 5의 정수인 경우, R1은 상기 화학식 1에서 정의한 바와 같다. 또, b가 0인 경우, 수소가 치환기 R2로 치환되지 않는 것을 의미하고, 상기 b가 1 내지 3의 정수인 경우, R2는 상기 화학식 1에서 정의한 바와 같다. 또한, c가 0인 경우, 수소가 치환기 R3로 치환되지 않는 것을 의미하고, 상기 c가 1 내지 4의 정수인 경우, R3는 상기 화학식 1에서 정의한 바와 같다. 이때, R1이 복수인 경우, 이들은 서로 동일하거나 상이하며, R2가 복수인 경우, 이들은 서로 동일하거나 상이하고, R3가 복수인 경우, 이들은 서로 동일하거나 상이하다.In the formula (1) according to the present invention, when a is 0, hydrogen is not substituted by substituent R 1 , and when a is an integer of 1 to 5, R 1 is as defined in the above formula (1). When b is 0, it means that hydrogen is not substituted with substituent R 2 , and when b is an integer of 1 to 3, R 2 is the same as defined in Formula 1. When c is 0, hydrogen means not substituted by substituent R 3 , and when c is an integer of 1 to 4, R 3 is the same as defined in formula (1). At this time, if R 1 is a plurality, these are the same or different, and, if R 2 is plural, if they are the same or different and, R 3 are each other plurality, which are the same or different from each other.
상기 R1 내지 R4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C20의 알킬기, C3~C20의 시클로알킬기, 핵원자수 3 내지 20의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C1~C20의 알킬옥시기, C6~C40의 아릴옥시기, C1~C20의 알킬실릴기, C6~C40의 아릴실릴기, C1~C20의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다. 또는, 바람직하게 R1-R2, R2-R3, R3-R4, 및/또는 R4-R1이 서로 결합하여 축합 방향족환 또는 N, P 및 S 중 선택된 헤테로원자를 함유하는 축합 헤테로방향족환을 형성할 수 있다.Wherein R 1 to R 4 are the same or different and are each independently selected from the group consisting of deuterium, halogen, cyano, C 1 to C 20 alkyl, C 3 to C 20 cycloalkyl, An alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 1 to C 20 alkyloxy group, a C 6 to C 40 aryloxy group, a C 1 to C 20 alkylsilyl group, C 6 ~ C 40 aryl silyl group, C 1 ~ C 20 group of an alkyl boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine it is selected from the group consisting pin oxide groups and C 6 ~ C 40 aryl amines are preferred. Or preferably R 1 -R 2 , R 2 -R 3 , R 3 -R 4 and / or R 4 -R 1 are bonded to each other to form a condensed aromatic ring or a heterocyclic ring containing a heteroatom selected from N, P and S To form a condensed heteroaromatic ring.
더 바람직하게, R1 내지 R4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C40의 아릴아민기로 이루어진 군에서 선택될 수 있다.More preferably, R 1 to R 4 are the same or different and each independently selected from the group consisting of C 6 to C 40 aryl groups, heteroaryl groups having 5 to 40 nuclear atoms, and C 6 to C 40 arylamine groups Can be selected from the group.
다만, 상기 R1 내지 R4 중 적어도 하나는 상기 화학식 2로 표시되는 치환체이다.Provided that at least one of R 1 to R 4 is a substituent represented by the general formula (2).
상기 화학식 2에서, L1은 단일결합이거나, 또는 C6~C20의 아릴렌기, 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되는 것이 바람직하다.In Formula 2, L 1 is preferably a single bond or a group selected from the group consisting of an arylene group having 6 to 20 carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms.
상기 화학식 1에서, Ar1 및 Ar2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C20의 알킬기, C6~C40의 아릴기, 및 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C40의 아릴아민기로 이루어진 군에서 선택되거나, 또는 Ar1과 Ar2가 서로 결합하여 축합환을 형성하는 것이 바람직하다.Wherein Ar 1 and Ar 2 are the same or different and each independently represents a C 1 to C 20 alkyl group, a C 6 to C 40 aryl group, and a heteroaryl group having 5 to 40 nuclear atoms and / A C 6 to C 40 arylamine group, or Ar 1 and Ar 2 are bonded to each other to form a condensed ring.
상기 Ar1 내지 Ar2의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기; R1 내지 R4의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴아민기와; L1의 알릴렌기 및 헤테로아릴렌기는 중수소, 할로겐, 시아노, C1~C40의 알킬기(바람직하게, C1~C20의 알킬기), C3~C40의 시클로알킬기(바람직하게, C3~C20의 시클로알킬기), 핵원자수 3 내지 40의 헤테로시클로알킬기(바람직하게, 핵원자수 3 내지 20의 헤테로시클로알킬기), C6~C60의 아릴기(바람직하게, C6~C40의 아릴기), 핵원자수 5 내지 60의 헤테로아릴기(바람직하게, 핵원자수 5 내지 40의 헤테로아릴기), C1~C40의 알킬옥시기(바람직하게, C1~C20의 알킬옥시기), C6~C60의 아릴옥시기(바람직하게, C6~C40의 아릴옥시기), C1~C40의 알킬실릴기(바람직하게, C1~C20의 알킬실릴기), C6~C60의 아릴실릴기(바람직하게, C6~C40의 아릴실릴기), C1~C40의 알킬보론기(바람직하게, C1~C20의 알킬보론기), C6~C60의 아릴보론기(바람직하게, C6~C40의 아릴보론기), C6~C60의 아릴포스핀기(바람직하게, C6~C40의 아릴포스핀기), C6~C60의 아릴포스핀옥사이드기(바람직하게, C6~C40의 아릴포스핀옥사이드기) 및 C6~C60의 아릴아민기(바람직하게, C6~C40의 아릴아민기)로 구성된 군으로부터 선택되는 1종 이상으로 치환기(바람직하게 1~3개의 치환기)로 치환되거나 비치환된다. 이때, 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 또는 상이하다.An alkyl group, an aryl group, a heteroaryl group and an arylamine group of Ar 1 to Ar 2 ; R 1 to the alkyl group of R 4, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, An arylphosphine oxide group, an arylamine group; The allylene group and heteroarylene group of L 1 may be substituted by deuterium, halogen, cyano, a C 1 to C 40 alkyl group (preferably a C 1 to C 20 alkyl group), a C 3 to C 40 cycloalkyl group 3 or a cycloalkyl group of C 20), the number of nuclear atoms of 3 to 40 heterocycloalkyl group (preferably of, can be from 3 to 20 heterocycloalkyl group), C 6 ~ C 60 aryl group (preferably a nuclear atom, C 6 ~ aryl), heteroaryl of nuclear atoms of 5 to 60 of the C 40 aryl group (preferably, a group of nuclear atoms of 5 to 40 heteroaryl group), C 1 ~ C 40 alkyloxy the time (preferably of, C 1 ~ C alkyloxy group of 20), C 6 ~ C 60 aryloxy the time (preferably of, C 6 ~ aryloxy C 40), C the 1 ~ C 40 alkyl silyl group (preferably a, C of 1 ~ C 20 Alkylsilyl group), an arylsilyl group of C 6 to C 60 (preferably an arylsilyl group of C 6 to C 40 ), a C 1 to C 40 alkylboron group (preferably a C 1 to C 20 alkylboron group), C 6 ~ C 60 aryl boron group (preferably of, C 6 ~ C 40 The arylboronic group), C 6 ~ C 60 aryl phosphine group (preferably, C 6 ~ C 40 aryl phosphine group), C 6 ~ C 60 aryl phosphine oxide groups (preferably, C 6 ~ C 40 of (Preferably 1 to 3 substituents) selected from the group consisting of an arylamine group (preferably an arylphosphine oxide group) and an arylamine group of C 6 to C 60 (preferably, an arylamine group of C 6 to C 40 ) ≪ / RTI > At this time, when a plurality of substituents are present, they are the same or different.
상기 화학식 2로 표시되는 치환체의 예로는 하기 화학식 3으로 표시되는 치환체 등이 있는데, 이에 한정되지 않는다.Examples of the substituent represented by the formula (2) include, but are not limited to, a substituent represented by the following formula (3).
상기 화학식 3에서,In Formula 3,
L1, Ar1 및 Ar2는 각각 상기 화학식 2에서 정의한 바와 같으며,L 1 , Ar 1 and Ar 2 are as defined in the above formula (2)
Z2는 단일결합이거나, 또는 O, S, 및 N(R5)로 이루어진 군에서 선택되고,Z 2 is a single bond or is selected from the group consisting of O, S, and N (R 5 )
R5는 수소, 중수소(D), C1~C40의 알킬기(바람직하게, C1~C20의 알킬기), C6~C60의 아릴기(바람직하게, C6~C30의 아릴기), 핵원자수 5 내지 60의 헤테로아릴기(바람직하게, 핵원자수 5 내지 30의 헤테로아릴기) 및 C6~C60의 아릴아민기(바람직하게, C6~C30의 아릴아민기)로 이루어진 군에서 선택되거나, 또는 인접하는 치환기와 결합하여 축합 방향족환 또는 축합 헤테로방향족환을 형성할 수 있으며;R 5 is preferably selected from the group consisting of hydrogen, deuterium (D), a C 1 to C 40 alkyl group (preferably a C 1 to C 20 alkyl group), a C 6 to C 60 aryl group (preferably a C 6 to C 30 aryl group , A heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms) and an arylamine group having 6 to 60 carbon atoms (preferably a C 6 to C 30 arylamine group ), Or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;
이때 상기 R5의 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기(바람직하게 C1~C20의 알킬기), C3~C40의 시클로알킬기(바람직하게, C3~C20의 시클로알킬기), 핵원자수 3 내지 40의 헤테로시클로알킬기(바람직하게, 핵원자수 3 내지 20의 헤테로시클로알킬기), C6~C60의 아릴기(바람직하게, C6~C30의 아릴기), 핵원자수 5 내지 60의 헤테로아릴기(바람직하게, 핵원자수 5 내지 30의 헤테로아릴기), C1~C40의 알킬옥시기(바람직하게, C1~C20의 알킬옥시기), C6~C60의 아릴옥시기(바람직하게, C6~C30의 아릴옥시기), C1~C40의 알킬실릴기(바람직하게, C1~C20의 알킬실릴기), C6~C60의 아릴실릴기(바람직하게, C6~C30의 아릴실릴기), C1~C40의 알킬보론기(바람직하게, C1~C20의 알킬보론기), C6~C60의 아릴보론기(바람직하게, C6~C30의 아릴보론기), C6~C60의 아릴포스핀기(바람직하게, C6~C30의 아릴포스핀기), C6~C60의 아릴포스핀옥사이드기(바람직하게, C6~C30의 아릴포스핀옥사이드기) 및 C6~C60의 아릴아민기(바람직하게, C6~C30의 아릴아민기)로 구성된 군으로부터 선택되는 1종 이상의 치환기로 치환되거나 비치환되고, 다만 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 또는 상이하다.The aryl, heteroaryl and arylamine groups of R 5 are each independently selected from the group consisting of deuterium, halogen, cyano, C 1 -C 40 alkyl (preferably C 1 -C 20 alkyl), C 3 -C 40 A cycloalkyl group (preferably a C 3 to C 20 cycloalkyl group), a heterocycloalkyl group having 3 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 20 nuclear atoms), a C 6 to C 60 aryl group (Preferably a C 6 to C 30 aryl group), a heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms), a C 1 to C 40 alkyloxy group Preferably a C 1 to C 20 alkyloxy group), a C 6 to C 60 aryloxy group (preferably a C 6 to C 30 aryloxy group), a C 1 to C 40 alkylsilyl group , An alkylsilyl group of C 1 to C 20 ), an arylsilyl group of C 6 to C 60 (preferably a C 6 to C 30 arylsilyl group), a C 1 to C 40 alkylboron group (preferably C 1 - alkyl group of boron C 20), C 6 ~ C 60 Arylboronic group (preferably, C group 6 to arylboronic of C 30), C 6 to C 60 aryl phosphine group of the (preferably, C 6 to C 30 aryl phosphine group), C of 6 to C 60 aryl phosphine (Preferably a C 6 to C 30 arylphosphine oxide group) and a C 6 to C 60 arylamine group (preferably a C 6 to C 30 arylamine group). And when the substituent is plural, they are the same as or different from each other.
전술한 화학식 1의 화합물은 하기 화학식 4 내지 7 중 어느 하나로 표시될 수 있다.The compound of formula (1) may be represented by any one of the following formulas (4) to (7).
상기 화학식 4 내지 7에서,In the above formulas 4 to 7,
R1 내지 R4, L1, Ar1 및 Ar2, a, b, 및 c는 각각 상기 화학식 1에서 정의된 바와 같고,R 1 to R 4 , L 1 , Ar 1, and Ar 2 , a, b, and c are each as defined in Formula 1,
a'는 0 ~ 4의 정수이고, b'는 0 ~ 2의 정수이며, c'는 0 ~ 3의 정수이다.a 'is an integer of 0 to 4, b' is an integer of 0 to 2, and c 'is an integer of 0 to 3.
상기 화학식 1로 표시되는 화합물의 예로는 하기 화학식 8 내지 11로 표시되는 화합물 등이 있는데, 이에 한정되지 않는다.Examples of the compound represented by the formula (1) include compounds represented by the following formulas (8) to (11), but are not limited thereto.
상기 화학식 8 내지 11에서,In the general formulas (8) to (11)
R1 내지 R4, L1, Ar1 및 Ar2, a, b, 및 c는 각각 상기 화학식 1에서 정의된 바와 같고,R 1 to R 4 , L 1 , Ar 1, and Ar 2 , a, b, and c are each as defined in Formula 1,
a'는 0 ~ 4의 정수이고, b'는 0 ~ 2의 정수이며, b"는 0 ~ 1의 정수이고, c'는 0 ~ 3의 정수이다.a 'is an integer of 0 to 4, b' is an integer of 0 to 2, b '' is an integer of 0 to 1, and c 'is an integer of 0 to 3.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화합물들로 구체화될 수 있는데, 이에 한정되는 것은 아니다. The compounds represented by formula (1) according to the present invention may be represented by the following compounds, but are not limited thereto.
본 발명에서 사용되는 "비치환된 알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 이의 비제한적인 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있다.As used herein, "unsubstituted alkyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 사용되는 "비치환된 시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이의 비제한적인 예로는 시클로프로필, 시클로펜틸, 시클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine)등이 있다.As used herein, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 사용되는 "비치환된 헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이의 비제한적인 예로는 모르폴린, 피페라진 등이 있다.As used herein, "unsubstituted heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon , Preferably one to three carbons, is substituted with a heteroatom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.
본 발명에서 사용되는 "비치환된 아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이때, 2 이상의 고리는 서로 단순 부착되거나 축합된 형태로 부착될 수 있다. 이의 비제한적인 예로는 페닐, 비페닐, 터페닐(terphenyl), 나프틸, 페난트릴, 안트릴 등이 있다.As used herein, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 사용되는 "비치환된 헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기로서, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 질소(N), 산소(O), 황(S) 또는 셀레늄(Se)과 같은 헤테로원자로 치환된다. 이때, 헤테로아릴은 2 이상의 고리가 서로 단순 부착되거나 축합된 형태로 부착될 수 있고, 나아가 아릴기와의 축합된 형태도 포함할 수 있다. 이러한 헤테로아릴의 비제한적인 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있다.The "unsubstituted heteroaryl" used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, , One to three carbons are substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.
본 발명에서 사용되는 "비치환된 알킬옥시"는 RO-로 표시되는 1가의 작용기를 의미하며, 상기 R은 탄소수 1 내지 40개의 알킬로서, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 비제한적인 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있다.As used herein, "unsubstituted alkyloxy" means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic ) Structure. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 사용되는 "비치환된 아릴옥시"는 R'O-로 표시되는 1가의 작용기를 의미하며, 상기 R'는 탄소수 6 내지 60의 아릴이다. 이러한 아릴옥시의 비제한적인 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다.As used herein, "unsubstituted aryloxy" means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 사용되는 "비치환된 알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, "비치환된 아릴실릴"은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미하고, "비치환된 아릴아민" 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.As used herein, the term "unsubstituted alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, Unsubstituted arylamine "refers to an amine substituted with aryl of 6 to 60 carbon atoms.
본 발명에서 "비치환된 알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "비치환된 아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미하고, "비치환된 아릴포스핀기"는 탄소수 1 내지 60의 아릴로 치환된 포스핀기를 의미하고, 비치환된 아릴포스핀옥사이드기는 탄소수 1 내지 60의 아릴로 치환된 포스핀옥사이드기를 의미한다.In the present invention, the term "unsubstituted alkylboron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylboron group" means a boron group substituted with aryl having 6 to 60 carbon atoms, Unsubstituted arylphosphine group "means a phosphine group substituted with aryl having 1 to 60 carbon atoms, and the unsubstituted aryl phosphine oxide group means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.
본 발명에서 사용되는 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.As used herein, "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem . Rev., 60:313 (1960); J. Chem . SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.
The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem . Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
한편, 본 발명은 전술한 화학식 1로 표시되는 화합물(바람직하게, 상기 화학식 4 내지 7 중 어느 하나로 표시되는 화합물)을 포함하는 유기 전계 발광 소자를 제공한다.On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the above-mentioned formula (1) (preferably a compound represented by any one of the above-mentioned formulas (4) to (7)).
구체적으로, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2종 이상 혼합되어 사용될 수 있다.Specifically, the present invention includes a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound represented by Formula 1. At this time, the compounds may be used alone or in combination of two or more.
본 발명의 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층을 포함하며, 이 중에서 적어도 하나의 유기물층은 상기 화합물을 포함하고, 바람직하게는 발광층 또는 정공 수송층이 상기 화합물을 포함할 수 있다. 특히, 상기 화학식 1로 표시되는 화합물이 발광층 물질로 유기 전계 발광 소자에 포함될 경우, 유기 전계 발광 소자의 발광효율, 휘도, 전력효율, 열적 안정성 및 소자 수명이 향상될 수 있다.According to an embodiment of the present invention, the at least one organic material layer includes a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer, and at least one organic material layer contains the compound, The hole transporting layer may contain the above compound. In particular, when the compound represented by Formula 1 is included in the organic electroluminescent device as a light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.
예를 들어, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료일 수 있으며, 바람직하게는 발광층의 인광 호스트일 수 있다.For example, the compound represented by Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and may preferably be a phosphorescent host of the light emitting layer.
본 발명의 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층을 포함하는데, 이때 적어도 하나의 유기물층, 바람직하게는 발광 보조층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 특히, 상기 화합물이 유기 전계 발광 소자의 발광 보조층 물질로 사용될 경우, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.According to another embodiment of the present invention, the at least one organic material layer includes a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer, wherein at least one organic material layer, May include a compound represented by the above formula (1). Particularly, when the compound is used as a light-emitting auxiliary layer material of an organic electroluminescent device, the efficiency (luminous efficiency and power efficiency), lifetime, brightness and driving voltage of the organic electroluminescent device can be improved.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판 위에, 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer .
일례에 따르면, 상기 유기 전계 발광 소자는 기판 위에, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 선택적으로, 상기 정공 수송층과 발광층 사이에는 발광 보조층이 삽입될 수 있다. 또, 상기 전자 수송층 위에는 전자 주입층이 위치할 수도 있다.According to an example, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked on a substrate. Alternatively, a light-emitting auxiliary layer may be interposed between the hole transport layer and the light emitting layer. The electron injection layer may be located on the electron transport layer.
본 발명의 유기 전계 발광 소자는 상기 1층 이상의 유기물층 중에서 적어도 하나(예컨대, 발광층 또는 발광 보조층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다.The organic electroluminescent device of the present invention may be formed by using a material known in the art (for example, a light emitting layer or a light emitting auxiliary layer) such that at least one of the one or more organic layers And forming an organic layer and an electrode using a method.
상기 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 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 발명에서 사용 가능한 기판의 예로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 있는데, 이에 한정되지 않는다.Examples of substrates usable in the present invention include silicon wafers, quartz or glass plates, metal plates, plastic films and sheets, but are not limited thereto.
또, 양극 물질의 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에 한정되는 것은 아니다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.
또, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에 한정되는 것은 아니다.Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층으로 사용되는 물질은 당업계에 알려진 통상의 물질이라면 특별히 한정되지 않는다.
The material used for the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.
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 for illustrative purposes only and are not intended to limit the scope of the present invention.
[[ 준비예Preparation Example 1] One] Core1Core1 의 합성Synthesis of
<단계 1> 5-<Step 1> 5- chlorochloro -2-nitro-5'-phenyl-1,1':3',1''--2-nitro-5'-phenyl-1,1 ': 3', 1 "- terphenyl테 페렌 의 합성Synthesis of
질소 기류 하에서 4-chloro-2-iodo-1-nitrobenzene 30g (105.84 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 34.8g (127 mmol), K2CO3 43.88g (317.52 mmol) 및 1,4-Dioxane/H2O 400ml/100 ml를 넣고 교반하였다. 40 ℃에서 Pd(PPh3)4 3.7 g (3.175 mmol)을 넣고, 110 ℃에서 12시간 동안 환류 교반하였다. 반응 종결 후, 디클로로메탄으로 유기층을 추출하고, 상기 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl (32 g, 수율: 78%)을 얻었다. 4-chloro-2-iodo- 1-nitrobenzene 30g (105.84 mmol), under nitrogen gas stream, [1,1 ': 3', 1 '' - terphenyl] -5'-ylboronic acid 34.8g (127 mmol), K 2 43.88 g (317.52 mmol) of CO 3 and 400 ml / 100 ml of 1,4-dioxane / H 2 O were added and stirred. At 40 ℃ placed Pd (PPh 3) 4 3.7 g (3.175 mmol), it was stirred under reflux at 110 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl (32 g, yield 78% .
1H-NMR: δ7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08(m, 3H), 8.25 (s, 1H), 8.44(d, 1H) 1 H-NMR:? 7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08
<단계 2> 6-<Step 2> 6- chlorochloro -1,3--1,3- diphenyl피덴 -9H--9H- carbazolecarbazole 의 합성Synthesis of
질소 기류 하에서 <단계 1>에서 합성된 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 30 g (82.93 mmol), triphenylphosphine 43.5 g (165.86 mmol), 및 1,2-dichlorobenzene 300 ml를 넣은 후 180 ℃에서 12시간 동안 환류교반하였다. 반응 종료 후, 디스틸레이션을 통해 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 유기층을 추출하였다. 추출된 유기층은 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 6-chloro-1,3-diphenyl-9H-carbazole (20 g, 수율: 67%)을 얻었다. 30 g (82.93 mmol) of 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl synthesized in Step 1 under nitrogen flow, 43.5 g (165.86 mmol) of triphenylphosphine, , And 300 ml of 1,2-dichlorobenzene were added thereto, followed by reflux stirring at 180 ° C for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed by distillation, and an organic layer was extracted with dichloromethane. The extracted organic layer was dried with MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 6-chloro-1,3-diphenyl-9H-carbazole (20 g, yield: 67%) was obtained by column chromatography.
1H-NMR: δ 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03 (s, 1H), 12.25(s, 1H) 1 H-NMR:? 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03
<단계 3> <Step 3> Core1 의Of Core1 합성 synthesis
질소 기류 하에서 상기 <단계 2>에서 합성된 6-chloro-1,3-diphenyl-9H-carbazole 20 g (56.52 mmol), Iodobenzene 13.8 g (67.82 mmol), Cu powder 0.06 g (5.652 mmol), K2CO3 15.6 g (113 mmol) 및 nitrobenzene(200 ml)를 혼합하고 190 ℃에서 12시간 동안 환류교반하였다. The <Step 2> The 6-chloro-1,3-diphenyl- 9H-carbazole 20 g (56.52 mmol) synthesized in a nitrogen stream, Iodobenzene 13.8 g (67.82 mmol) , Cu powder 0.06 g (5.652 mmol), K 2 15.6 g (113 mmol) of CO 3 and nitrobenzene (200 ml) were mixed and refluxed at 190 ° C for 12 hours.
반응이 종결된 후, nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음, MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 Core1 (18 g, 수율: 74 %)을 얻었다.After the reaction was terminated, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain a compound Core1 (18 g, yield: 74%).
1H-NMR: δ 7.02 (d, 1H), 7.25 (m, 4H), 7.58 (m, 7H), 7.88 (m, 3H) 8.08(s, 1H)
1 H-NMR: δ 7.02 ( d, 1H), 7.25 (m, 4H), 7.58 (m, 7H), 7.88 (m, 3H) 8.08 (s, 1H)
[[ 준비예Preparation Example 2] 2] Core2Core2 의 합성Synthesis of
<단계 1> 5-<Step 1> 5- chlorochloro -2-nitro-5'-phenyl-1,1':2',1''--2-nitro-5'-phenyl-1,1 ': 2', 1 "- terphenyl테 페렌 의 합성Synthesis of
준비예 1의 <단계 1>에서 사용된 [1,1':3',1''-terphenyl]-5'-ylboronic acid 대신 [1,1':4',1''-terphenyl]-2'-ylboronic acid 34.8 g (127 mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일한 과정을 수행하여 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl (31 g, 수율: 75 %)을 얻었다.[1,1 ': 4', 1 "-terphenyl] -2 (2'-tert-butylphenyl) -5'-ylboronic acid was used in place of [ 2-nitro-5'-phenyl-1,1 ': 2 (1) was obtained by following the procedure of <Step 1> of Preparation Example 1, except that 34.8 g ', 1' '- terphenyl (31 g, yield: 75%).
1H-NMR: δ7.36 (m, 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52(m,2H) 1 H-NMR: δ7.36 (m , 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52 (m, 2H)
<단계 2> 6-<Step 2> 6- chlorochloro -1,4--1,4- diphenyl피덴 -9H--9H- carbazolecarbazole 의 합성Synthesis of
준비예 1의 <단계 2>에서 사용된 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 대신 상기 <단계 1>에서 합성된 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl 30 g (82.93 mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 2>와 동일한 과정을 수행하여 6-chloro-1,4-diphenyl-9H-carbazole (19 g, 수율: 64 %)을 얻었다. Chloro- 2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl used in Step 2 of Preparation Example 1 was used instead of 5-chloro- Step 2 of Preparation Example 1 was repeated, except that 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 2', 1 " -chloro-1,4-diphenyl-9H-carbazole (19 g, yield 64%).
1H-NMR: δ 7.12 (m, 5H), 7.48 (m, 6H), 7.82 (m, 2H), 8.23 (m, 2H), 12.18(s, 1H) 1 H-NMR: δ 7.12 ( m, 5H), 7.48 (m, 6H), 7.82 (m, 2H), 8.23 (m, 2H), 12.18 (s, 1H)
<단계 3> <Step 3> Core2 의Core2 합성 synthesis
준비예 1의 <단계 3>에서 사용된 6-chloro-1,3-diphenyl-9H-carbazole 대신 6-chloro-1,4-diphenyl-9H-carbazole 20 g (56.52 mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 3>과 동일한 과정을 수행하여 화합물 Core2 (18 g, 수율: 74 %)를 얻었다.Except that 20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole was used instead of the 6-chloro-1,3-diphenyl-9H-carbazole used in Step 3 of Preparation Example 1 , And Step 3 of Preparation Example 1 were carried out to obtain a compound Core2 (18 g, yield: 74%).
1H-NMR: δ 7.02 (d, 1H), 7.28 (m, 4H), 7.52 (m, 11H), 7.85 (m, 2H) 8.41(d, 1H), 8.52(d, 1H)
1 H-NMR: δ 7.02 ( d, 1H), 7.28 (m, 4H), 7.52 (m, 11H), 7.85 (m, 2H) 8.41 (d, 1H), 8.52 (d, 1H)
[[ 준비예Preparation Example 3] 3] Core3 의Core3 합성 synthesis
질소 기류 하에서 준비예 1의 <단계 2>에서 얻은 6-chloro-1,3-diphenyl-9H-carbazole 20 g (56.52 mmol), phenylboronic acid 8.27g (67.82 mmol), Cs2CO3 55.2 g (169.56 mmol), X-Phos 2.7g (5.65 mmol) 및 1,4-Dioxane/H2O (400ml/100 ml)를 넣고 교반하였다. 40 ℃에서 Pd(oAc)2 0.38 g (1.695 mmol)를 넣고, 110 ℃에서 12시간 동안 환류 교반하였다. 반응 종결 후, 디클로로메탄으로 유기층을 추출하고, 상기 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 화합물 Core 3 (16g, 수율: 71 %)을 얻었다. 20 g (56.52 mmol) of 6-chloro-1,3-diphenyl-9H-carbazole, 8.27 g (67.82 mmol) of phenylboronic acid and 55.2 g (169.56 mmol) of Cs 2 CO 3 obtained in Step 2 of Preparation Example 1 2.7 g (5.65 mmol) of X-Phos and 1,4-dioxane / H 2 O (400 ml / 100 ml) were added and stirred. 0.38 g (1.695 mmol) of Pd (oAc) 2 was added thereto at 40 ° C, and the mixture was refluxed and stirred at 110 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then subjected to column chromatography to obtain a compound Core 3 (16 g, yield: 71%).
1H-NMR: δ 7.18 (m, 4H), 7.50 (m, 7H), 7.82 (m, 6H), 7.92(s, 1H), 8.08 (m, 2H), 12.25(s, 1H)
1 H-NMR: δ 7.18 ( m, 4H), 7.50 (m, 7H), 7.82 (m, 6H), 7.92 (s, 1H), 8.08 (m, 2H), 12.25 (s, 1H)
[[ 준비예Preparation Example 4] 4] Core4 의Core4 합성 synthesis
준비예 3에서 사용된 6-chloro-1,3-diphenyl-9H-carbazole 대신 준비예 2의 <단계 2>에서 얻은 6-chloro-1,4-diphenyl-9H-carbazole 20g (56.52 mmol)을 사용한 것을 제외하고는, 준비예 3과 동일한 과정을 수행하여 Core4 (15 g, 수율: 67 %)를 얻었다.20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole obtained in Step 2 of Preparation Example 2 was used instead of 6-chloro-1,3-diphenyl-9H- , Core 4 (15 g, yield: 67%) was obtained in the same manner as in Preparation Example 3.
1H-NMR: δ 7.15 (m, 4H), 7.47 (m, 7H), 7.81 (m, 5H), 7.92(s,1H), 8.03 (d, 1H), 8.26 (m, 2H), 12.18(s, 1H)
1 H-NMR: δ 7.15 ( m, 4H), 7.47 (m, 7H), 7.81 (m, 5H), 7.92 (s, 1H), 8.03 (d, 1H), 8.26 (m, 2H), 12.18 ( s, 1 H)
[[ 준비예Preparation Example 5] 5] Core5 의Core5 합성 synthesis
<단계 1> 4-<Step 1> 4- chlorochloro -2-nitro-5'-phenyl-1,1':3',1''--2-nitro-5'-phenyl-1,1 ': 3', 1 "- terphenyl테 페렌 의 합성Synthesis of
질소 기류 하에서 4-chloro-2-iodo-1-nitrobenzene 30g (105.83 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 34.8g (127 mmol), K2CO3 43.88g (317.52 mmol)과 1,4-Dioxane/H2O (400ml/100 ml)를 넣고 교반하였다. 40 ℃에서 Pd(PPh3)4 3.7 g (3.175 mmol)을 넣고, 110 ℃에서 12시간 동안 환류 교반하였다. 반응 종결 후, 디클로로메탄으로 유기층을 추출하고, 상기 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl (32g, 수율:78%)을 얻었다. 4-chloro-2-iodo- 1-nitrobenzene 30g (105.83 mmol), under nitrogen gas stream, [1,1 ': 3', 1 '' - terphenyl] -5'-ylboronic acid 34.8g (127 mmol), K 2 43.88 g (317.52 mmol) of CO 3 and 1,4-dioxane / H 2 O (400 ml / 100 ml) were added and stirred. At 40 ℃ placed Pd (PPh 3) 4 3.7 g (3.175 mmol), it was stirred under reflux at 110 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 4-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl (32g, yield: 78%) was obtained by column chromatography .
1H-NMR : δ 7.51 (m, 6H), 7.82 (m, 4H), 8.05 (m, 5H), 8.52 (s, 1H) 1 H-NMR:? 7.51 (m, 6H), 7.82 (m, 4H), 8.05
<단계 2> 7-<Step 2> 7- chlorochloro -1,3--1,3- diphenyl피덴 -9H--9H- carbazolecarbazole 의 합성Synthesis of
준비예 1의 <단계 2>에서 사용된 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 대신 상기 <단계 1>에서 합성된 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 30 g (82.93 mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 2>와 동일한 과정을 수행하여 7-chloro-1,3-diphenyl-9H-carbazole (20 g, 수율: 67 %)을 얻었다. Chloro- 2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl used in Step 2 of Preparation Example 1 was used instead of 5-chloro-2- Step 2 of Preparation Example 1 was repeated except that 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 3', 1 " -chloro-1,3-diphenyl-9H-carbazole (20 g, yield 67%).
1H-NMR : δ 6.98 (d, 1H), 7.18 (m, 4H), 7.45 (m, 5H), 7.78 (m, 3H), 8.05(m, 2H), 12.20(s, 1H) 1 H-NMR: δ 6.98 ( d, 1H), 7.18 (m, 4H), 7.45 (m, 5H), 7.78 (m, 3H), 8.05 (m, 2H), 12.20 (s, 1H)
<단계 3> <Step 3> Core5 의Core5 합성 synthesis
준비예 3에서 사용된 6-chloro-1,3-diphenyl-9H-carbazole 대신 7-chloro-1,3-diphenyl-9H-carbazole 20g (56.52 mmol)을 사용한 것을 제외하고는, 준비예 3과 동일한 과정을 수행하여 화합물 Core5 (16 g, 수율: 71%)를 얻었다.Except that 20 g (56.52 mmol) of 7-chloro-1,3-diphenyl-9H-carbazole was used in place of 6-chloro-1,3-diphenyl-9H-carbazole used in Preparation Example 3 (16 g, yield: 71%) was obtained.
1H-NMR: δ 7.2 (m, 4H), 7.48 (m, 7H), 7.78 (m, 6H), 7.92(d, 1H), 8.05 (s, 1H), 8.30(d, 1H), 12.22(s, 1H)
1 H-NMR: δ 7.2 ( m, 4H), 7.48 (m, 7H), 7.78 (m, 6H), 7.92 (d, 1H), 8.05 (s, 1H), 8.30 (d, 1H), 12.22 ( s, 1 H)
[[ 준비예Preparation Example 6] 6] Core6 의Core6 합성 synthesis
<단계 1> 1-<Step 1> 1- chlorochloro -3--3- methoxy메틸oxy -9-phenyl-9H--9-phenyl-9H- carbazole 의carbazole 합성 synthesis
준비예 1의 <단계 3>에서 사용된 6-chloro-1,3-diphenyl-9H-carbazole 대신 1-chloro-3-methoxy-9H-carbazole 20 g (86.33 mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 3>과 동일한 과정을 수행하여 1-chloro-3-methoxy-9-phenyl-9H-carbazole (20 g, 수율: 75%)를 얻었다.Except that 20 g (86.33 mmol) of 1-chloro-3-methoxy-9H-carbazole was used in place of the 6-chloro-1,3-diphenyl-9H-carbazole used in Step 3 of Preparation Example 1 1-chloro-3-methoxy-9-phenyl-9H-carbazole (20 g, yield: 75%) was obtained in the same manner as in <Step 3> of Example 1.
1H-NMR : δ 3.88 (s, 3H), 6.75 (s, 1H), 7.22 (t, 1H), 7.45 (t, 1H) 7.68(m, 6H), 8.02(d, 1H), 8.58(d, 1H) 1 H-NMR: δ 3.88 ( s, 3H), 6.75 (s, 1H), 7.22 (t, 1H), 7.45 (t, 1H) 7.68 (m, 6H), 8.02 (d, 1H), 8.58 (d , 1H)
<단계 2> 3-≪ Step 2 > 3- methoxy메틸oxy -1,9--1,9- diphenyl피덴 -9H--9H- carbazolecarbazole 의 합성Synthesis of
준비예 1의 <단계 1>에서 사용된 4-chloro-2-iodo-1-nitrobenzene 대신 1-chloro-3-methoxy-9-phenyl-9H-carbazole 20 g (64.98 mmol)을 사용하고, [1,1':3',1''-terphenyl]-5'-ylboronic acid 대신 Phenyl boronic acid 9.5 g (77.97mmol)을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일한 과정을 수행하여 3-methoxy-1,9-diphenyl-9H-carbazole (16 g, 수율:70%)을 얻었다. 20 g (64.98 mmol) of 1-chloro-3-methoxy-9-phenyl-9H-carbazole was used in place of 4-chloro-2-iodo-1-nitrobenzene used in <Step 1> , Step 1 of Preparation Example 1 was repeated except that 9.5 g (77.97 mmol) of phenyl boronic acid was used instead of 1 ': 3', 1 "-terphenyl] -5'-ylboronic acid 3-methoxy-1,9-diphenyl-9H-carbazole (16 g, yield: 70%).
1H-NMR : δ 3.82 (s, 3H), 7.16 (m, 5H), 7.62 (m, 8H), 7.85 (s, 1H), 7.92(d, 1H), 8.57(d, 1H) 1 H-NMR: δ 3.82 ( s, 3H), 7.16 (m, 5H), 7.62 (m, 8H), 7.85 (s, 1H), 7.92 (d, 1H), 8.57 (d, 1H)
<단계 3> 1,9-≪ Step 3 > diphenyl피덴 -9H--9H- carbazolcarbazole -3--3- ol 의ol 합성 synthesis
질소 기류 하에서 상기 <단계 2>에서 얻은 3-methoxy-1,9-diphenyl-9H-carbazole 16g, (45.78 mmol)을 400 mL의 48% aqueous hydrobromic acid 에 넣고, 120 ℃에서 5시간 동안 교반하였다. 반응액을 40 ℃로 식힌 후, 1L의 물을 넣고 sodium bicarbonate로 중화시켰다. 이후, 생성된 고체를 필터링하고, 건조한 후 컬럼크로마토그래피로 정제하여 1,9-diphenyl-9H-carbazol-3-ol (6 g, 수율: 40%)을 얻었다.16 g (45.78 mmol) of 3-methoxy-1,9-diphenyl-9H-carbazole obtained in the above Step 2 was added to 400 mL of 48% aqueous hydrobromic acid under a nitrogen stream and the mixture was stirred at 120 ° C for 5 hours. The reaction mixture was cooled to 40 ° C, and 1 L of water was added thereto, followed by neutralization with sodium bicarbonate. Thereafter, the resulting solid was filtered, dried and then purified by column chromatography to obtain 1,9-diphenyl-9H-carbazol-3-ol (6 g, yield: 40%).
1H-NMR : δ 7.18 (m, 5H), 7.51 (m, 9H), 8.02 (d, 1H), 8.68 (d, 1H) 9.45(s, 1H) 1 H-NMR:? 7.18 (m, 5H), 7.51 (m, 9H), 8.02 (d,
<단계 4> Core 6의 합성<Step 4> Synthesis of Core 6
질소 기류 하에서 상기 <단계 3>에서 얻은 1,9-diphenyl-9H-carbazol-3-ol 6g, (17.88 mmol), Trifluoromethanesulfonic anhydride 2.5g (8.94 mmol), 및 Pyridine 10g (17.88 mmol)을 100 mL의 Dichloro methan 에 넣고 0 ℃ 에서 1시간 동안 교반하였다. 반응 종결 후, 디클로로메탄으로 유기층을 추출한 다음, 상기 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 후, 컬럼 크로마토그래피를 이용하여 목적 화합물인 Core 6 (5.8 g, 수율: 69%)을 얻었다.6 g (17.88 mmol) of 1,9-diphenyl-9H-carbazol-3-ol, 2.5 g (8.94 mmol) of trifluoromethanesulfonic anhydride and 10 g (17.88 mmol) of pyridine obtained in the above Step 3 were dissolved in a 100 mL Dichloromethane and stirred at 0 ° C for 1 hour. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then Core 6 (5.8 g, yield: 69%) was obtained by column chromatography.
1H-NMR : δ 7.15 (m, 5H), 7.48 (m, 9H), 7.94 (m, 2H), 8.15 (m, 3H) 8.62(d, 1H)
1 H-NMR: δ 7.15 ( m, 5H), 7.48 (m, 9H), 7.94 (m, 2H), 8.15 (m, 3H) 8.62 (d, 1H)
[[ 합성예Synthetic example 1] 화합물 1] Compound InvInv 1의 합성 Synthesis of 1
질소 기류 하에서 준비예 1에서 합성된 화합물 Core1 3.0 g (6.97 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine 2.77 g (7.66 mmol), Pd(OAc)2 0.047 g (0.209mmol), NaO(t-bu) 1.34 g (13.94 mmol), P(t-bu)3 0.14 g (0.697 mmol) 및 Toluene (80 ml)을 혼합한 다음, 110 ℃에서 12시간 동안 교반하였다.Under nitrogen atmosphere, 3.0 g (6.97 mmol) of the compound Core1 synthesized in Preparation Example 1 and 2.77 g of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- (7.66 mmol), Pd (OAc ) 2 0.047 g (0.209mmol), NaO (t-bu) 1.34 g (13.94 mmol), P (t-bu) 3 0.14 g (0.697 mmol) and Toluene (80 ml) to After mixing, the mixture was stirred at 110 DEG C for 12 hours.
반응이 종결된 후, 에틸아세테이트로 유기층을 추출한 다음, 상기 유기층에서 MgSO4로 수분을 제거하고, 컬럼크로마토그래피로 정제하여 목적화합물인 Inv 1 (2.8 g, 수율: 53%)을 얻었다. After the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried over MgSO 4 and purified by column chromatography to obtain the desired compound Inv1 (2.8 g, yield: 53%).
GC-Mass (이론치: 754.98 g/mol, 측정치: 754 g/mol)
GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)
[[ 합성예Synthetic example 2] 화합물 2] Compound InvInv 13의 합성 Synthesis of 13
합서예 1에서 사용된 N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine 대신 di([1,1'-biphenyl]-4-yl)amine (2.4 g, 7.66 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 13 (2.6 g, 수율: 52%)을 얻었다([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N - yl) amine (2.4 g, 7.66 mmol) was used as a starting material, the target compound Inv 13 (2.6 g, yield: 52%) was obtained
GC-Mass (이론치: 714.91 g/mol, 측정치: 714 g/mol)
GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)
[[ 합성예Synthetic example 3] 화합물 3] Compound InvInv 37의 합성 Synthesis of 37
질소 기류 하에서 준비예 1의 화합물 Core1 3 g (6.97 mmol), (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 3.38g (7.66 mmol), K2CO3 2.89g (20.91 mmol) 및 1,4-Dioxane/H2O 100ml/250 ml를 넣고 교반하였다. 40 ℃에서 Pd(PPh3)4 0.24g (0.209mmol)을 넣고, 110 ℃에서 12시간 동안 환류 교반하였다. 반응 종결 후, 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 Inv37 (3.5g, 수율: 60%)을 얻었다. (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl (4-methylphenyl) 3.38 g (7.66 mmol) of boronic acid, 2.89 g (20.91 mmol) of K 2 CO 3 and 100 ml / 250 ml of 1,4-dioxane / H 2 O were added and stirred. 0.24 g (0.209 mmol) of Pd (PPh 3 ) 4 was added at 40 ° C, and the mixture was refluxed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and the desired compound Inv37 (3.5 g, yield: 60%) was obtained by column chromatography.
GC-Mass (이론치: 831.08 g/mol, 측정치: 831 g/mol)
GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)
[[ 합성예Synthetic example 4] 화합물 4] Compound InvInv 49의 합성 Synthesis of 49
합성예 3에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid 3.38 g (7.66 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 49 (3.6 g, 수율: 65 %)를 얻었다.Instead of (4- (di ((1,1'-biphenyl) -4-yl (9,9-dimethyl-9H- The same procedure as in Synthesis Example 3 was carried out except that 3.38 g (7.66 mmol) of [1,1'-biphenyl] -4-yl) amino) , Yield: 65%).
GC-Mass (이론치: 791.01 g/mol, 측정치: 791 g/mol)
GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)
[[ 합성예Synthetic example 5] 화합물 5] Compound InvInv 70의 합성 Synthesis of 70
합성예 3에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 4.0g (7.66 mmol) 을 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 70 (3.8 g, 수율: 63%)을 얻었다.Instead of (4- (bis (4-methylpiperazin-1-yl) amino) phenyl) boronic acid used in Synthesis Example 3 instead of 4- The same procedure as in Synthesis Example 3 was carried out except that 4.0 g (7.66 mmol) of 9,9-dimethyl-9H-fluoren-2-yl) amino) g, yield: 63%).
GC-Mass (이론치: 871.14 g/mol, 측정치: 871 g/mol)
GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)
[[ 합성예Synthetic example 6] 화합물 6] compound InvInv 87의 합성 Synthesis of 87
합성예 3에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (4-(diphenylamino)phenyl)boronic acid 2.21 g(7.66 mmol)를 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 87 (2.8 g, 수율: 62 %)을 얻었다.(4- (diphenylamino) phenyl) boronic acid instead of (4 - ([1,1'-biphenyl] -4-yl phenyl) boronic acid (2.21 g, 7.66 mmol) was used in place of the compound obtained in Synthesis Example 3 to obtain Inv 87 (2.8 g, yield 62%) as a target compound.
GC-Mass (이론치: 638.8 g/mol, 측정치: 638 g/mol)
GC-Mass (theory: 638.8 g / mol, measured: 638 g / mol)
[[ 합성예Synthetic example 7] 화합물 7] Compound InvInv 89의 합성 Synthesis of 89
합성예 3에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (4'-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1'-biphenyl]-4-yl)boronic acid 4.27 g (7.66 mmol)을 사용한 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 89 (4.0 g, 수율: 63 %)를 얻었다.(4 '- ([(1, 1'-biphenyl) -4-yl (9,9- (9,9-dimethyl-9H-fluoren-2-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid, 4.27 g (7.66 mmol) (Inv 89) (4.0 g, yield: 63%) was obtained by carrying out the same procedure as in Synthesis Example 3, except that
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 8] 화합물 8] compound InvInv 91 의91 of 합성 synthesis
합성예 3에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (3'-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1'-biphenyl]-4-yl)boronic acid 4.27 g (7.66 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 91 (4.2 g, 수율: 66%)을 얻었다.(3 '- ([(1, 1'-biphenyl) -4-yl (9,9- (9,9-dimethyl-9H-fluoren-2-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid, 4.27 g (7.66 mmol) , The procedure of Synthesis Example 3 was repeated to obtain the target compound Inv91 (4.2 g, yield: 66%).
GC-Mass (이론치: 907.17 g/mo, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 9] 화합물 9] compound InvInv 93의 합성 Synthesis of 93
합성예 1에서 사용된 화합물 Core1 대신 준비예 2에서 합성된 화합물 Core2 3.0 g (6.97 mmol)를 사용하는 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 93 (2.9g, 수율: 55%)을 얻었다.The same procedure as in Synthesis Example 1 was carried out, except that 3.0 g (6.97 mmol) of the compound Core2 synthesized in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 1, to obtain the desired compound Inv 93 (2.9 g, yield : 55%).
GC-Mass (이론치: 822.87 g/mol, 측정치: 822 g/mol)
GC-Mass (theory: 822.87 g / mol, measured: 822 g / mol)
[[ 합성예Synthetic example 10] 화합물 10] compound InvInv 105의 합성 Synthesis of 105
합성예 2 사용된 화합물 Core1 대신 준비예 2에서 합성된 화합물 Core2 3.0 g (6.97 mmol)를 사용하는 것을 제외하고는, 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Inv 105(2.7 g, 수율: 54%)를 얻었다.Synthesis Example 2 The same procedure as in Synthesis Example 2 was carried out except that 3.0 g (6.97 mmol) of the compound Core2 synthesized in Preparation Example 2 was used in place of the used compound Core1 to obtain the desired compound Inv 105 (2.7 g, yield: 54%).
GC-Mass (이론치: 714.91 g/mol, 측정치: 714 g/mol)
GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)
[[ 합성예Synthetic example 11] 화합물 11] compound InvInv 129의 합성 Synthesis of 129
합성예 3에서 사용된 화합물 Core1 대신 준비예 2의 화합물 Core2 3.0 g (6.97 mmol)를 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 129 (3.3 g, 수율: 60%)를 얻었다.The procedure of Synthesis Example 3 was repeated except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 3 to obtain the desired compound Inv 129 (3.3 g, yield: 60 %).
GC-Mass (이론치: 831.09 g/mol, 측정치: 831 g/mol)
GC-Mass (calculated: 831.09 g / mol, measured: 831 g / mol)
[[ 합성예Synthetic example 12] 화합물 12] compound InvInv 141의 합성 Synthesis of 141
합성예 4에서 사용된 화합물 Core1 대신 준비예 2의 화합물 Core2 3.0 g (6.97 mmol)를 사용하는 것을 제외하고는, 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Inv 141 (2.9 g, 수율: 55%)을 얻었다.In the same manner as in Synthesis Example 4 except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 4, Inv 141 (2.9 g, yield: 55 %).
GC-Mass (이론치: 791.01 g/mol, 측정치: 791 g/mol)
GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)
[[ 합성예Synthetic example 13] 화합물 13] Compound InvInv 183의 합성 Synthesis of 183
합성예 8에서 사용된 화합물 Core1 대신 준비예 2의 화합물 Core2 3.0 g (6.97 mmol)를 사용하는 것을 제외하고는, 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 183 (3.9 g, 수율: 61%)을 얻었다.The procedure of Synthetic Example 8 was repeated, except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 8, to obtain the desired compound Inv 183 (3.9 g, yield: 61 %).
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 14] 화합물 14] Compound InvInv 221의 합성 Synthesis of 221
질소 기류 하에서 준비예 3에서 얻은 Core3 3.0 g (7.58 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 4.7g (9.10 mmol), Cu powder 0.048 g (0.758 mmol), K2CO3 2.09 g (15.16 mmol) 및 nitrobenzene(80 ml)를 혼합하고, 190 ℃에서 12시간 동안 환류교반하였다. (3.0 g, 7.58 mmol) and N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluorene -2-amine, 0.048 g (0.758 mmol) of Cu powder, K 2 CO 3 2.09 g (15.16 mmol) and nitrobenzene (80 ml) were mixed and refluxed at 190 캜 for 12 hours.
반응이 종결된 후, nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음, MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 Inv 221(3.8 g, 수율 60%)을 얻었다.After the reaction was terminated, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO 4 . After removal of the organic layer solvent, the residue was purified by column chromatography to give the desired compound, Inv 221 (3.8 g, yield 60%).
GC-Mass (이론치: 831.08 g/mol, 측정치: 831 g/mol)
GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)
[[ 합성예Synthetic example 15] 화합물 15] Compound InvInv 227의 합성 Synthesis of 227
N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-diphenyl-9H-fluoren-2-amine (5.83 g,9.1 mmol)을 사용하는 것을 제외하고는 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 227 (4.4 g, 수율 61%)을 얻었다.N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- -4-yl) -N- (4-bromophenyl) -9,9-diphenyl-9H-fluoren-2-amine (5.83 g, 9.1 mmol) The target compound Inv 227 (4.4 g, yield 61%) was obtained.
GC-Mass (이론치: 955.22 g/mol, 측정치: 955 g/mol)
GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)
[[ 합성예Synthetic example 16] 화합물 16] compound InvInv 233의 합성 Synthesis of 233
합성예 14에서 사용된 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine 4.33 g (9.1 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 233 (4.0 g, 수율 66%)을 얻었다.Instead of N - ([1, 1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- fluoren- , 4'-biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine The same procedure was followed to obtain the desired compound Inv 233 (4.0 g, yield 66%).
GC-Mass (이론치: 791.01 g/mol, 측정치: 791 g/mol)
GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)
[[ 합성예Synthetic example 17] 화합물 17] Compound InvInv 254의 합성 Synthesis of 254
합성예 14에서 사용된 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 대신 N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine 5.0 g (9.1 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 254 (4.1 g, 수율 62%)을 얻었다.(4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine instead of the N - ([1,1'- biphenyl] -4-yl) -N- except that 5.0 g (9.1 mmol) of bromophenyl-N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-9H- 14, the target compound Inv 254 (4.1 g, yield 62%) was obtained.
GC-Mass (이론치: 871.14 g/mol, 측정치: 871 g/mol)
GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)
[[ 합성예Synthetic example 18] 화합물 18] compound InvInv 273의 합성 Synthesis of 273
합성예 14에서 사용된 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine 5.39 g (9.1 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 273 (4.5 g, 수율 65%)을 얻었다.Instead of N - ([1, 1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- fluoren- -4'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- 9.1 mmol), the target compound Inv 273 (4.5 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 14.
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 19] 화합물 19] Compound InvInv 313의 합성 Synthesis of 313
합성예 14에서 사용된 Core3 대신 준비예 4에서 얻은 Core4 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 313 (4.3 g, 수율 68%)을 얻었다.Inv 313 (4.3 g, yield 68%) was obtained in the same manner as in Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 14. ≪ / RTI >
GC-Mass (이론치: 831.08 g/mol, 측정치: 831 g/mol)
GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)
[[ 합성예Synthetic example 20] 화합물 20] compound InvInv 319의 합성 Synthesis of 319
합성예 15에서 사용된 Core3 대신 준비예 4에서 얻은 Core4 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 15와 동일한 과정을 수행하여 목적 화합물인 Inv319 (4.8 g, 수율 66%)를 얻었다.Inv 319 (4.8 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 15 .
GC-Mass (이론치: 955.22 g/mol, 측정치: 955 g/mol)
GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)
[[ 합성예Synthetic example 21] 21] InvInv 325의 합성 Synthesis of 325
합성예 16에서 사용된 Core 3 대신 준비예 4에서 얻은 Core4 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 325 (3.9 g, 수율 65%)를 얻었다.Inv 325 (3.9 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 16. ).
GC-Mass (이론치: 791.01 g/mol, 측정치: 791 g/mol)
GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)
[[ 합성예Synthetic example 22] 화합물 22] compound InvInv 346의 합성 346
합성예 17에서 사용된 Core3 대신 준비예 4에서 얻은 Core4 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 17과 동일한 과정을 수행하여 목적 화합물인 Inv 346 (4.2 g, 수율 63%)을 얻었다.Inv 346 (4.2 g, yield 63%) was obtained in the same manner as in Preparation Example 17, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used in place of Core 3 used in Preparation Example 17. ≪ / RTI >
GC-Mass (이론치: 871.14 g/mol, 측정치: 871 g/mol)
GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)
[[ 합성예Synthetic example 23] 화합물 23] Compound InvInv 365의 합성 Synthesis of 365
합성예 18에서 사용된 Core3 대신 준비예 4에서 얻은 Core4 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 18과 동일한 과정을 수행하여 목적 화합물인 Inv 365 (4.4 g, 수율 64%)를 얻었다.Inv 365 (4.4 g, yield 64%) was obtained in the same manner as in Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 18. .
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 24] 화합물 24] Compound InvInv 405의 합성 Synthesis of 405
합성예 14에서 사용된 Core3 대신 준비예 5에서 얻은 Core5 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 405 (4.1 g, 수율 65%)를 얻었다.Inv 405 (4.1 g, yield 65%) was obtained in the same manner as in Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 14. .
GC-Mass (이론치: 831.08 g/mol, 측정치: 831 g/mol)
GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)
[[ 합성예Synthetic example 25] 화합물 25] Compound InvInv 411의 합성 Synthesis of 411
합성예 15에서 사용된 Core3 대신 준비예 5에서 얻은 Core5 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 15와 동일한 과정을 수행하여 목적 화합물인 Inv 411 (4.5 g, 수율 62%)를 얻었다.Inv 411 (4.5 g, yield 62%) was obtained in the same manner as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 15. .
GC-Mass (이론치: 955.22 g/mol, 측정치: 955 g/mol)
GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)
[[ 합성예Synthetic example 26] 화합물 26] compound InvInv 417의 합성 Synthesis of 417
합성예 16에서 사용된 Core3 대신 준비예 5에서 얻은 Core5 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 417 (3.9 g, 수율 65%)을 얻었다.Inv 417 (3.9 g, yield 65%) was obtained in the same manner as in Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 16. ≪ / RTI >
GC-Mass (이론치: 791.01 g/mol, 측정치: 791 g/mol)
GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)
[[ 합성예Synthetic example 27] 화합물 27] Compound InvInv 457의 합성 Synthesis of 457
합성예 18에서 사용된 Core3 대신 준비예 5에서 얻은 Core5 3.0 g (7.58 mmol)을 사용하는 것을 제외하고는, 합성예 18과 동일한 과정을 수행하여 목적 화합물인 Inv 457 (4.3 g, 수율 63%)을 얻었다.Inv 457 (4.3 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 18, ≪ / RTI >
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 28] 화합물 28] Compound InvInv 459의 합성 Synthesis of 459
합성예 14에서 사용된 Core3 대신 준비예 5에서 얻은 Core5 3.0 g (7.58 mmol)을 사용하고, N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine 5.38 g (9.1 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 459 (4.2 g, 수율 61%)를 얻었다.Except that Core5 3.0 g (7.58 mmol) obtained in Preparation Example 5 was used in place of Core 3 used in Synthesis Example 14 and N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9 4-yl) -N- (4'-bromo- [1,1'-biphenyl] -3-yl ) The title compound, Inv 459 (4.2 g, yield 61%) was obtained by following the same procedure as in Synthesis Example 14, except for using 5.38 g (9.1 mmol) of 9,9-dimethyl-9H- ).
GC-Mass (이론치: 907.17 g/mol, 측정치: 907 g/mol)
GC-Mass (907.17 g / mol, measured: 907 g / mol)
[[ 합성예Synthetic example 29] 화합물 29] Compound InvInv 588 의588 합성 synthesis
합성예 3에서 사용된 Core1 대신 준비예 6의 <단계 4>에서 합성한Core 6 3g, (6.41mmol)을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 588 (3.3 g, 수율 68%)을 얻었다The procedure of Synthesis Example 3 was repeated except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core 1 used in Synthesis Example 3 to obtain the target compound Inv 588 (3.3 g, yield 68%) was obtained
GC-Mass (이론치: 754.98 g/mol, 측정치: 754 g/mol)
GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)
[[ 합성예Synthetic example 30] 화합물 30] Compound InvInv 600 의600 합성 synthesis
합성예 4에서 사용된 Core1 대신 준비예 6의 <단계 4>에서 합성한Core 6 3g, (6.41mmol)을 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Inv 600 (3.1 g, 수율 68%)을 얻었다The same procedure as in Synthesis Example 4 was carried out except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core 1 used in Synthesis Example 4 to obtain the target compound Inv 600 (3.1 g, yield 68%) was obtained
GC-Mass (이론치: 714.91 g/mol, 측정치: 714 g/mol)
GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)
[[ 합성예Synthetic example 31] 화합물 31] Compound InvInv 638의 합성 Synthesis of 638
합성예 6에서 사용된 Core1 대신 준비예 6의 <단계 4>에서 합성한Core 6 3g, (6.41mmol)을 사용하는 것을 제외하고는, 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Inv 638 (2.5 g, 수율 70%)을 얻었다Except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core1 used in Synthesis Example 6, the target compound Inv 638 ( 2.5 g, yield 70%) was obtained
GC-Mass (이론치: 562.72 g/mol, 측정치: 562 g/mol)
GC-Mass (calculated: 562.72 g / mol, measured: 562 g / mol)
[[ 합성예Synthetic example 32] 화합물 32] compound InvInv 680 의680 합성 synthesis
합성예 3에서 사용된 Core1 대신 1-chloro-3,9-diphenyl-9H-carbazole 3.0 g (8.47 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 680 (4.0 g, 수율 62%)을 얻었다The procedure of Synthesis Example 3 was repeated except that 3.0 g (8.47 mmol) of 1-chloro-3,9-diphenyl-9H-carbazole was used in place of Core 1 used in Synthesis Example 3 to obtain the target compound Inv 680 4.0 g, yield: 62%) was obtained
GC-Mass (이론치: 754.98 g/mol, 측정치: 754 g/mol)
GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)
[[ 합성예Synthetic example 33] 화합물 33] Compound InvInv 692의 합성 Synthesis of 692
합성예 32에서 사용된 (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid 4.54g (10.16 mmol) 을 사용하는 것을 제외하고는, 합성예 32와 동일한 과정을 수행하여 목적 화합물인 Inv 692 (3.8 g, 수율 63%)를 얻었다.Instead of (4- (di ((1,1'-biphenyl) -4-yl (9,9-dimethyl-9H-fluoren- The same procedure as in Synthesis Example 32 was carried out, except that 4.54 g (10.16 mmol) of [1,1'-biphenyl] -4-yl) amino) , Yield: 63%).
GC-Mass (이론치: 714.91 g/mol, 측정치: 714 g/mol)
GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)
[[ 합성예Synthetic example 34] 화합물 C- 34] Compound C- 1 의1 of 합성 synthesis
<단계 1> 1-phenyl-9H-<Step 1> Synthesis of 1-phenyl-9H- carbazolecarbazole 의 합성Synthesis of
합성예 3에서 사용된 Core1 대신 1-chloro-9H-carbazole 10g (49.59 mmol)을 사용하고, (4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 대신 Phenyl boronic acid 7.25g (59.5 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일한 과정을 수행하여 1-phenyl-9H-carbazole (8.5 g, 수율: 70%)을 얻었다. 10 g (49.59 mmol) of 1-chloro-9H-carbazole was used in place of Core1 used in Synthesis Example 3, and (4 - ([1,1'-biphenyl] -4-yl Phenyl-9H-carbazole (8.5 g, yield: 97%) was obtained in the same manner as in Synthesis Example 3, except that 7.25 g (59.5 mmol) of phenyl boronic acid was used in place of 2- : 70%).
1H-NMR: δ 7.22 (m, 3H), 7.52 (m, 2H), 7.67 (d, 1H), 8.12(d, 1H), 8.22 (d, 1H), 8.35(d, 1H), 12.15(s, 1H) 1 H-NMR: δ 7.22 ( m, 3H), 7.52 (m, 2H), 7.67 (d, 1H), 8.12 (d, 1H), 8.22 (d, 1H), 8.35 (d, 1H), 12.15 ( s, 1 H)
<단계 2> 화합물 C-1의 합성<Step 2> Synthesis of Compound C-1
합성예 14에서 사용된 Core3 대신 상기 <단계 1>에서 합성된 1-phenyl-9H-carbazole 8.5g(34.93 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적화합물인 C-1(16 g, 수율: 67%)을 얻었다. The procedure of Synthesis Example 14 was repeated except that 8.5 g (34.93 mmol) of 1-phenyl-9H-carbazole synthesized in the above Step 1 was used instead of Core 3 used in Synthesis Example 14 to obtain the target compound C -1 (16 g, yield: 67%).
GC-Mass (이론치: 678.88 g/mol, 측정치: 678 g/mol)
GC-Mass (theory: 678.88 g / mol, measured: 678 g / mol)
[[ 합성예Synthetic example 35] 화합물 C- 35] Compound C- 2 의2 of 합성 synthesis
<단계 1> 1,4-<Step 1> 1,4- diphenyl피덴 -2,3,4,9--2,3,4,9- tetrahydrotetrahydro -1H--1H- carbazolecarbazole 의 합성Synthesis of
질소 기류 하에서 2,5-diphenylcyclohexan-1-one 50g (199.72 mmol), Phenylhydrazine hydrochloride 29g (199.72 mmol) 및 Acetic acid 500ml를 넣고, 120 ℃에서 12시간 동안 환류 교반하였다. 반응 종결 후, Acetic acid를 제거한 후, Sodium bicarbonate 및 디클로로메탄으로 유기층을 추출하고, 상기 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 후 컬럼 크로마토그래피를 이용하여 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole (43 g, 수율: 66%)을 얻었다. 50 g (199.72 mmol) of 2,5-diphenylcyclohexan-1-one, 29 g (199.72 mmol) of phenylhydrazine hydrochloride and 500 ml of acetic acid were placed under a nitrogen stream and refluxed at 120 ° C for 12 hours. After completion of the reaction, acetic acid was removed, and the organic layer was extracted with sodium bicarbonate and dichloromethane. The organic layer was dried with MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole (43 g, yield 66%) was obtained by column chromatography.
1H-NMR : δ 1.96 (m, 2H), 4.02 (m, 2H), 6.83 (m, 2H), 7.29(m, 4H), 7.75 (d, 1H), 8.05(d, 1H), 12.12 (s, 1H) 1 H-NMR: δ 1.96 ( m, 2H), 4.02 (m, 2H), 6.83 (m, 2H), 7.29 (m, 4H), 7.75 (d, 1H), 8.05 (d, 1H), 12.12 ( s, 1 H)
<단계 2> 1,4-≪ Step 2 > diphenyl피덴 -9H--9H- carbazolecarbazole 의 합성Synthesis of
질소 기류 하에서 상기 <단계 1>에서 얻은 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole 43 g (133.12 mmol) 및 Benzene 300ml를 넣은 후, 30분간 다섯 차례에 걸쳐 DDQ 60 g (264.24 mmol)을 나누어 넣고, 1시간 동안 교반하였다. 반응 종료 후, Silicagel 및 Celite에 필터링한 후 Benzene을 제거하고, 디클로로메탄으로 유기층을 추출하였다. 추출된 유기층은 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 1,4-diphenyl-9H-carbazole (29 g, 수율:70%)을 얻었다. 43 g (133.12 mmol) of 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole obtained in the above Step 1 and 300 ml of benzene were placed in a nitrogen gas stream, g (264.24 mmol), and the mixture was stirred for 1 hour. After completion of the reaction, the mixture was filtered through Silicagel and Celite, benzene was removed, and organic layer was extracted with dichloromethane. The extracted organic layer was dried with MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 1,4-diphenyl-9H-carbazole (29 g, yield: 70%) was obtained by column chromatography.
1H-NMR : δ 7.22 (m, 5H), 7.42 (m, 4H), 7.68 (d, 1H), 7.82 (m, 2H), 8.19 (m, 3H), 12.18(s, 1H) 1 H-NMR:? 7.22 (m, 5H), 7.42 (m, 4H), 7.68 (d,
<단계 3> 화합물 C-2의 합성<Step 3> Synthesis of Compound C-2
합성예 14에서 사용된 Core3 대신 상기 <단계 2>에서 1,4-diphenyl-9H-carbazole 10g(31.3 mmol)을 사용하는 것을 제외하고는, 합성예 14와 동일한 과정을 수행하여 목적화합물인 C-2 (15.8 g, 수율: 67%)를 얻었다.The procedure of Synthesis Example 14 was repeated except that 10 g (31.3 mmol) of 1,4-diphenyl-9H-carbazole was used in Step 2 instead of Core 3 used in Synthesis Example 14, 2 (15.8 g, yield 67%).
GC-Mass (이론치: 754.98 g/mol, 측정치: 754 g/mol)
GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)
[[ 실시예Example 1] - 유기 EL 소자의 제조 1] - Manufacture of organic EL 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 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum deposition machine.
상기와 같이 준비된 ITO 투명 전극 위에 m-MTDATA (60nm) / 합성예 1에서 합성된 화합물 Inv 1 (80 nm) / [DS-H522 + 5% DS-501] (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1nm) / Al (200 nm)의 순서로 유기 EL 소자를 제조하였다. (60 nm) / compound Inv 1 (80 nm) / [DS-H522 + 5% DS-501] (30 nm) / BCP (10 nm) synthesized in Synthesis Example 1 on m-MTDATA / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).
상기에서 사용된 DS-H522 및 DS-501은 ㈜두산 전자 BG의 제품이며, m-MTDATA, 및 BCP의 구조는 각각 하기와 같다.DS-H522 and DS-501 used in the above are products of Doosan Electronics BG Co., Ltd. The structures of m-MTDATA and BCP are as follows.
[[ 실시예Example 2 ~ 35] - 유기 EL 소자의 제조 2 ~ 35] - Manufacture of organic EL device
실시예 1에서 정공 수송층의 형성시 정공 수송층 물질로 사용된 화합물 Inv 1 대신 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 유기 EL 소자를 제조하였다.
An organic EL device was manufactured in the same manner as in Example 1 except that the compound described in Table 1 was used instead of the compound Inv 1 used as a hole transporting layer material in the formation of the hole transport layer in Example 1.
[[ 비교예Comparative Example 1] - 유기 EL 소자의 제작 1] - Fabrication of organic EL device
실시예 1에서 정공 수송층의 형성시 정공 수송층 물질로 사용된 화합물 Inv 1 대신 NPB를 정공수송층 물질로 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 EL 소자를 제조하였다. 이때 사용된 NPB의 구조는 하기와 같다.An organic EL device was prepared in the same manner as in Example 1, except that NPB was used as the hole transport layer material instead of the compound Inv 1 used as the hole transport layer material in forming the hole transport layer in Example 1. The structure of the NPB used here is as follows.
[[ 평가예Evaluation example 1] One]
실시예 1 내지 35, 및 비교예 1에서 각각 제조된 유기 EL 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율를 측정하였고, 그 결과를 하기 표 1에 나타내었다.The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 1 to 35 and Comparative Example 1, respectively, and the results are shown in Table 1 below.
상기 표1에 나타낸 바와 같이, 본 발명에 따른 화합물(Inv 1 ~ Inv 417, C-1~C-2)을 정공수송층으로 사용한 유기 EL 소자(실시예 1 내지 35의 유기 EL 소자)는, 종래 NPB를 사용한 유기 EL 소자(비교예1의 유기 EL 소자)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다. As shown in Table 1 above, the organic EL devices (organic EL devices of Examples 1 to 35) using the compounds (Inv 1 to Inv 417, C-1 to C-2) It was found that the current efficiency and the driving voltage were superior to those of the organic EL device using NPB (organic EL device of Comparative Example 1).
또한, 카바졸의 1, 3, 6번 위치에 각각 페닐기가 도입된 화합물 Inv 221을 정공수송층으로 사용한 실시예 14의 유기 EL 소자는 카바졸의 1번 위치에 페닐기가 도입된 화합물 C-1이나 카바졸 1, 4번 위치에 각각 페닐기가 도입된 화합물 C-2를 정공수송층으로 사용한 실시예 34~35의 유기 EL 소자에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.
Further, the organic EL device of Example 14, in which the compound Inv 221 in which the phenyl group was introduced at positions 1, 3 and 6 of the carbazole, was used as the hole transport layer, was obtained by using Compound C-1 in which phenyl group was introduced at position 1 of carbazole It was found that the organic EL device of the present invention exhibited better current efficiency and driving voltage than the organic EL devices of Examples 34 to 35, in which the compound C-2 in which the phenyl group was introduced at positions 1 and 4 of carbazole was used as the hole transport layer.
[[ 실시예Example 36] - 녹색 유기 36] - green organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
합성예 1에서 합성된 Inv 1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was prepared as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm) / TCTA (80 nm) / Inv 1 (40 nm) / CBP + 10 % Ir(ppy)3 (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순서로 적층하여 유기 전계 발광 소자를 제조하였다.(60 nm) / TCTA (80 nm) / Inv 1 (40 nm) / CBP + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) on the ITO transparent electrode prepared above, Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.
이때 사용된 m-MTDATA, TCTA, Ir(ppy)3, 및 BCP의 구조는 각각 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP used herein are as follows.
[[ 실시예Example 37 ~ 63] - 녹색 유기 37 ~ 63] - Green organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
실시예 36에서 발광 보조층의 형성시 발광 보조층 물질로 사용된 화합물 Inv 1 대신 하기 표 2에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 36과 동일하게 수행하여 녹색 유기 EL 소자를 제조하였다.
A green organic EL device was produced in the same manner as in Example 36 except that the compound shown in the following Table 2 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in the luminescent auxiliary layer in Example 36 Respectively.
[[ 비교예Comparative Example 2] - 녹색 유기 2] - green organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
실시예 36에서 사용된 화합물 Inv 1을 사용하지 않은 것을 제외하고는, 실시예 36과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.
A green organic electroluminescent device was fabricated in the same manner as in Example 36 except that the compound Inv 1 used in Example 36 was not used.
[[ 평가예Evaluation example 2] 2]
실시예 36 내지 63, 및 비교예 2에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 2에 나타내었다.The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 36 to 63 and Comparative Example 2, respectively, and the results are shown in Table 2 below .
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 보조층 재료로 사용한 녹색 유기 전계 발광 소자(실시예 36~63의 녹색 유기 전계 발광 소자)는, 발광 보조층 재료 없이 종래 CBP만을 발광층 재료로 사용한 녹색 유기 전계 발광 소자(비교예 2의 유기 전계 발광 소자)에 비해 구동전압은 유사하나 발광 효율이 개선되는 것을 알 수 있었다.
As shown in Table 2 above, the green organic electroluminescent devices (the green organic electroluminescent devices of Examples 36 to 63) using the compound represented by Formula 1 according to the present invention as the light-emitting auxiliary layer material, It was found that the driving voltage was similar to that of the green organic electroluminescent device (organic electroluminescent device of Comparative Example 2) using only CBP as the light emitting layer material, but the luminous efficiency was improved.
[[ 실시예Example 64] - 적색 유기 64] - Red organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
합성예 1에서 합성한 화합물 Inv 1을 통적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.Compound Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a method known in common, and then a red organic electroluminescent device was fabricated according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm) / TCTA (80 nm) / 화합물 Inv 1 (40 nm) / CBP + 10 % (piq)2Ir(acac) (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순서로 적층하여 적색 유기 전계 발광 소자를 제조하였다.(60 nm) / TCTA (80 nm) / Compound Inv 1 (40 nm) / CBP + 10% (piq) 2 Ir (acac) (30 nm) / BCP 10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare a red organic electroluminescent device.
이때 사용된 m-MTDATA, TCTA, (piq)2Ir(acac) 및 BCP의 구조는 각각 하기와 같다.The structures of m-MTDATA, TCTA, (piq) 2 Ir (acac) and BCP used herein are as follows.
[[ 실시예Example 65 ~ 91] - 적색 유기 65 ~ 91] - Red organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
실시예 64에서 발광 보조층의 형성시 발광 보조층 물질로 사용된 화합물 Inv 1 대신 하기 표 3에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 64와 동일하게 수행하여 적색 유기 EL 소자를 제조하였다.
A red organic EL device was manufactured in the same manner as in Example 64 except that the compound described in the following Table 3 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in forming the luminescent auxiliary layer in Example 64 Respectively.
[[ 비교예Comparative Example 3] - 적색 유기 3] - Red organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
실시예 64에서 Inv-1을 사용하지 않은 것을 제외하고는, 실시예 64와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.
A red organic electroluminescent device was manufactured in the same manner as in Example 64 except that Inv-1 was not used in Example 64. [
[[ 평가예Evaluation example 3] 3]
실시예 64 내지 91, 및 비교예 3에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 2에 나타내었다.The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 64 to 91 and Comparative Example 3, respectively, and the results are shown in Table 2 below .
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 보조층 재료로 사용한 적색 유기 전계 발광 소자(실시예 64~91의 적색 유기 전계 발광 소자)는, 발광 보조층 없이 종래 CBP만을 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예 3의 유기 전계 발광 소자)에 비해 구동전압은 유사하나 발광 효율이 개선되는 것을 알 수 있었다.
As shown in the above Table 3, the red organic electroluminescent devices (red organic electroluminescent devices of Examples 64 to 91) using the compound represented by Formula 1 according to the present invention as the light emitting auxiliary layer material, Compared with the red organic electroluminescent device (organic electroluminescent device of Comparative Example 3) using only CBP as the material of the light emitting layer, the driving voltage was similar but the luminous efficiency was improved.
[[ 실시예Example 92] - 청색 유기 92] - blue organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
합성예 1에서 합성한 화합물 Inv 1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was fabricated according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (두산社) (80 nm) / NPB (15 nm) / 화합물 Inv 1 (15nm) / ADN + 5 % DS-405 (두산社) (30nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순서로 적층하여 청색 유기 전계 발광 소자를 제조하였다.(15 nm) / ADN + 5% DS-405 (Doosan) (30 nm) / BCP (compound semiconductor)) on the ITO transparent electrode prepared as above. (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare a blue organic electroluminescent device.
이때 사용된 NPB, ADN 및 BCP의 구조는 각각 하기와 같다. The structures of NPB, ADN and BCP used at this time are as follows.
[[ 실시예Example 93 ~119] - 청색 유기 93 ~ 119] - Blue organic 전계Field 발광 소자의 제조 Manufacturing of light emitting device
실시예 92에서 발광 보조층의 형성시 발광 보조층 물질로 사용된 화합물 Inv 1 대신 하기 표 4에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 92와 동일하게 수행하여 청색 유기 EL 소자를 제조하였다.
A blue organic EL device was manufactured in the same manner as in Example 92 except that the compound shown in the following Table 4 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in the formation of the luminescent auxiliary layer in Example 92 Respectively.
[[ 비교예Comparative Example 4] - 청색 유기 4] - blue organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
실시예 92에서 사용된 화합물 Inv-1을 사용하지 않은 것을 제외하고는, 실시예 92와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.
A blue organic electroluminescent device was fabricated in the same manner as in Example 92 except that the compound Inv-1 used in Example 92 was not used.
[[ 평가예Evaluation example 4] 4]
실시예 92~119 및 비교예 4 에서 각각 제작된 청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하였고, 그 결과를 하기 표 4에 나타내었다.The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the blue organic electroluminescent devices manufactured in Examples 92 to 119 and Comparative Example 4, respectively, and the results are shown in Table 4 below.
상기 표 4에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 보조층 재료로 사용한 청색 유기 전계 발광 소자(실시예 92~119의 청색 유기 전계 발광 소자)는, 발광 보조층 없이 종래 ADN의 발광층만 포함하는 청색 유기 전계 발광 소자(비교예 4의 유기 전계 발광 소자)에 비해 구동전압은 유사하나 발광 효율이 개선되는 것을 알 수 있었다.As shown in Table 4, the blue organic electroluminescent devices (blue organic electroluminescent devices of Examples 92 to 119) using the compound represented by Formula 1 according to the present invention as the luminescent auxiliary layer material, It was found that the driving voltage was similar to that of the blue organic electroluminescent element including only the light emitting layer of ADN (organic electroluminescent element of Comparative Example 4), but the luminous efficiency was improved.
Claims (9)
[화학식 4]
(상기 화학식 4에서,
a는 0 내지 5의 정수이고;
b는 0 내지 3의 정수이며;
c는 0 내지 4의 정수이고;
R1 내지 R3은 서로 동일하거나 또는 상이하며, 각각 독립적으로 할로겐 및 C6~C60의 아릴기로 이루어진 군에서 선택되며;
L1은 단일 결합이거나, 페닐렌기 또는 바이페닐렌기이고;
Ar1 및 Ar2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C6~C60의 아릴기로 이루어진 군에서 선택되며,
Ar1 내지 Ar2의 아릴기, R1 내지 R3의 아릴기 및 L1의 페닐렌기, 바이페닐렌기는 C6~C60의 아릴기로 구성된 군으로부터 선택되는 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 또는 상이함).A compound represented by the following general formula (4):
[Chemical Formula 4]
(In the formula 4,
a is an integer from 0 to 5;
b is an integer from 0 to 3;
c is an integer from 0 to 4;
R 1 to R 3 are the same or different and are each independently selected from the group consisting of halogen and C 6 to C 60 aryl groups;
L 1 is a single bond or a phenylene group or a biphenylene group;
Ar 1 and Ar 2 are the same or different and are each independently selected from the group consisting of C 6 to C 60 aryl groups,
The aryl group of Ar 1 to Ar 2, the aryl group of R 1 to R 3 , the phenylene group of L 1 , and the biphenylene group may be substituted with one or more substituents selected from the group consisting of C 6 to C 60 aryl groups, When the substituent is plural, they are the same or different from each other).
상기 화학식 8로 표시되는 화합물:
[화학식 8]
(상기 화학식 8에서,
R1 내지 R3, L1, Ar1 및 Ar2, a 및 c는 각각 제1항에서 정의된 바와 같고,
b'는 0 ~ 2의 정수임).The method according to claim 1,
The compound represented by the above general formula (8)
[Chemical Formula 8]
(In the formula (8)
R 1 to R 3 , L 1 , Ar 1 and Ar 2 , a and c are each as defined in claim 1,
b 'is an integer of 0 to 2).
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 또는 제2항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 and 2.
상기 화합물은 발광층의 호스트로 사용되는 것이 특징인 유기 전계 발광 소자.The method according to claim 6,
Wherein the compound is used as a host of the light emitting layer.
상기 화합물은 정공수송층 재료로 사용되는 것이 특징인 유기 전계 발광 소자.The method according to claim 6,
Wherein the compound is used as a hole transporting layer material.
상기 화합물은 발광보조층 재료로 사용되는 것이 특징인 유기 전계 발광 소자.The method according to claim 6,
Wherein the compound is used as a light emitting auxiliary layer material.
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