WO2017104946A1 - Organic compound, composition, organic optoelectronic element, and display device - Google Patents
Organic compound, composition, organic optoelectronic element, and display device Download PDFInfo
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- WO2017104946A1 WO2017104946A1 PCT/KR2016/010521 KR2016010521W WO2017104946A1 WO 2017104946 A1 WO2017104946 A1 WO 2017104946A1 KR 2016010521 W KR2016010521 W KR 2016010521W WO 2017104946 A1 WO2017104946 A1 WO 2017104946A1
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 79
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 230000005693 optoelectronics Effects 0.000 title claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 83
- 239000010410 layer Substances 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- -1 hydrogen hydrogen Chemical class 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 72
- 238000003786 synthesis reaction Methods 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 239000000543 intermediate Substances 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 238000000921 elemental analysis Methods 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 18
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 16
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- 0 Cc1c(*)nc(c2c(*)c(*)c(*)c(*)c2c2c3c(*)c(*)c(*)c2*)c3n1 Chemical compound Cc1c(*)nc(c2c(*)c(*)c(*)c(*)c2c2c3c(*)c(*)c(*)c2*)c3n1 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 230000008859 change Effects 0.000 description 10
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 7
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- 238000000151 deposition Methods 0.000 description 6
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 5
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
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- 108010072897 transcription factor Brn-2 Proteins 0.000 description 5
- 108010017443 B 43 Proteins 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000005103 alkyl silyl group Chemical group 0.000 description 4
- 238000005137 deposition process Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
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- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- CMUCQFDGOMDFFD-UHFFFAOYSA-N [O-2].[Zn+2].[Rh+3] Chemical compound [O-2].[Zn+2].[Rh+3] CMUCQFDGOMDFFD-UHFFFAOYSA-N 0.000 description 2
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
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- 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 2
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N Cc1cc(Cl)ccc1 Chemical compound Cc1cc(Cl)ccc1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- FBGNGKPKNAUYCI-UHFFFAOYSA-N Clc1cc(-c2ccccc2-c(cc2)cc3c2c2nccnc2c2c3cccc2)ccc1 Chemical compound Clc1cc(-c2ccccc2-c(cc2)cc3c2c2nccnc2c2c3cccc2)ccc1 FBGNGKPKNAUYCI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 102100021202 Desmocollin-1 Human genes 0.000 description 1
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 101000968043 Homo sapiens Desmocollin-1 Proteins 0.000 description 1
- 101000880960 Homo sapiens Desmocollin-3 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 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 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero 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
- C07D403/10—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
- C07D403/14—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 three or more hetero rings
-
- 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
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- An organic compound a composition, an organic optoelectronic device, and a display device.
- Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
- Organic optoelectronic devices can be divided into two types according to the principle of operation.
- One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electric energy.
- Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
- organic light emitting diodes have attracted much attention recently as demand for flat panel displays increases.
- An organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has an organic layer interposed between an anode and a cathode.
- the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic material included in the organic layer.
- One embodiment provides an organic compound capable of implementing high efficiency and long life organic optoelectronic devices.
- One embodiment provides an organic optoelectronic device composition comprising the organic compound. Another embodiment provides an organic optoelectronic device including the organic compound. Another embodiment provides a display device including the organic optoelectronic device.
- an organic compound represented by Chemical Formula 1 is provided.
- Z 1 to Z 13 are each independently N or CR a
- At least one of Z 1 to Z 13 is N,
- L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group
- R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, or a combination thereof,
- R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, a substituted or unsubstituted C 3 to C 12 hate Logo or a combination thereof,
- R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring
- nl and n2 are each independently an integer of 0 to 2.
- the organic compound includes a first organic compound, and at least one crab 2 organic compound having a carbazole moiety.
- an organic optoelectronic device It provides a composition for an organic optoelectronic device.
- a display device including the organic optoelectronic device is provided.
- FIG. 1 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment.
- substituted means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C10 trifluoro such as C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group, C2 to C30 heterocyclic group, C1 to C20 alkoxy group, trifluoromethyl group, etc.
- substituted herein refers to a deuterium, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C 1 to C40 silyl group, C1 to It may be substituted with a C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group or C2 to C30 heterocyclic group.
- substituted means a deuterium, a substituted or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group or C6 to C30 aryl group Can be substituted have.
- substituted halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to Two adjacent substituents of C 1 to C 10 trifluoroalkyl group or cyano group such as C 30 aryl group, C 3 to C 30 heterocyclic group, C 1 to C 20 alkoxy group, trifluoromethyl group, etc. may be fused to form a ring.
- the substituted C6 to C30 aryl group may be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
- hetero 'includes at least one heteroatom in one functional group and the remainder is carbon, said heteroatom selected from N, 0, S, P and Si. Can be.
- aryl group refers to a group having one or more carbocyclic aromatic moieties, and broadly the form in which the carbocyclic aromatic moieties are connected in a single bond and the carbocyclic aromatic moieties are directly or
- Aryl groups include monocyclic, polycyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
- heterocyclic group refers to at least one hetero atom selected from N, 0, S, P and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof or a combination thereof. Containing, and the rest is carbon.
- the heterocyclic group may include one or more heteroatoms for all or each ring.
- a substituted or unsubstituted aryl group and / or a substituted or unsubstituted heterocyclic group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted group Substituted phenanthryl groups, substitutions or
- Naphthyridinyl groups substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted
- Phenazineyl group substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted
- a dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a combination thereof, or a combination thereof may be in a fused form, but is not limited thereto.
- the substituted or unsubstituted aryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted It may be a quarterphenyl group or a substituted or unsubstituted fluorenyl group.
- a substituted or unsubstituted indenyl group a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group , Substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Done
- Dibenzofuran group may be a substituted or unsubstituted di banjo a thiophenyl group, a substituted or unsubstituted carbazole, a combination thereof or a combination thereof fused form, but is not The "May eu
- the hole characteristic refers to electrons when an electric field is applied. It refers to a property that can form holes by donating, and has conductivity characteristics along the HOMO level to facilitate injection of holes formed in the anode into the light emitting layer, movement of holes formed in the light emitting layer into the anode, and movement in the light emitting layer. Means to come.
- the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
- An organic compound according to one embodiment may be represented by Formula 1 below.
- Z 1 to Z 13 are each independently N or CR a ,
- At least one of Z 1 to Z 13 is N,
- L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group
- R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
- R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 'heterocyclic group Or a combination thereof,
- R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring
- nl and n2 are each independently an integer of 0 to 2.
- the organic compound may include a dibenzoquinoxaline moiety and a ring having at least one nitrogen, and thus may have a structure in which electrons are easily received when an electric field is applied, and thus driving voltage of the organic optoelectronic device to which the organic compound is applied. This can lower the efficiency and increase efficiency.
- the LUMO energy of the organic compound calculated by the B3LYP / 6-31G ** method using Gaussian 09 can be, for example, -1.5 eV to -2.0 eV. Within this range, for example, about 1.7 eV to -1.8 eV.
- the organic compound may implement an asymmetric structure by including a nitrogen-containing ring substituent that extends to one side about the dibenzoquinoxaline, thereby lowering the crystallinity by inhibiting the interaction of molecules.
- the organic compound has an asymmetric structure so that
- Effectively preventing stacking can increase process stability while lowering the deposition temperature.
- At least two of Z 1 to Z 13 may be N.
- at least three of Z 1 to Z 13 may be N.
- at least one of Z 1 to Z 3 may be N.
- at least one of ⁇ to Z 3 may be N, and each of Z 4 to Z 13 may independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group. , A substituted or unsubstituted C6 internal C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
- at least two of Z 1 to Z 3 may be N.
- At least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be N or CR a , wherein R a is hydrogen, hydrogen, substituted or unsubstituted. Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
- Z 1 to Z 3 may be all N, ⁇ 4 to ⁇ 13 may be each independently ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted Or an unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
- L 1 may be, for example, a single bond or have at least one kink structure.
- the fold structure refers to a structure in which two connecting portions do not form a straight structure.
- o-phenylene and meta-phenylene in which the connecting portions do not form a straight structure, are represented.
- P-phenylene having a folding structure and the connecting portions forming a straight structure does not have a bending structure.
- L 1 is, for example, a single bond, a substituted or unsubstituted phenylene group having a folding structure, a substituted or unsubstituted biphenylene group having a folding structure, a substituted or unsubstituted terphenylene group having a folding structure, a folding structure It may be a substituted or unsubstituted quarterphenylene group, a substituted or unsubstituted pentaphenylene group having a folding structure.
- L 1 may include, for example, at least one of a single bond or a substituted or unsubstituted 0-phenylene group and a substituted or unsubstituted m-phenylene group.
- L 1 may be, for example, a single bond or one selected from substituted or unsubstituted groups listed in Group 1 below.
- R 30 to R 57 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 heteroarylamine group, substituted or unsubstituted C1 to C30 alkoxy Group, halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, ferrocenyl group, or a combination thereof.
- the molecular weight of the organic compound may be, for example, about 750 or less. Within this range may be greater than or equal to about 538 and less than 750. By having a molecular weight in the above range it is possible to reduce the thermal decomposition of the organic compound by the high temperature during the deposition process and to improve the heat resistance. It may be about 538 to 749 within the range, may be about 550 to 730 within the range, may be about 600 to 700 within the range.
- the organic compound may be represented by, for example, the following Chemical Formula 2.
- ⁇ 1 to Z ⁇ R 1 to R 14 , nl and n 2 are as described above,
- R 15 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof Can,
- n3 and n4 may be each independently an integer of 0 to 2.
- At least two of Z 1 to Z 13 may be N.
- at least three of Z 1 to Z 13 may be N.
- at least one of Z 1 to Z 3 may be N.
- at least one of Z 1 to Z 3 may be N, and Z 4 to Z 13 may each independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group , A substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- at least two of Z 1 to Z 3 may be N.
- At least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1.
- R a is hydrogen, deuterium, substituted or unsubstituted C1.
- C10 alkyl group a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- Z 1 to Z 3 may be all N
- Z 4 to Z 13 may be each independently N or CR a
- R a is hydrogen, deuterium, substituted or unsubstituted C1 to It may be a C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
- the organic compound may be represented by, for example, the following Chemical Formula 3 or 4.
- X 1 to Z ⁇ R 1 to R 17 , nl to n4 are as described above.
- at least two of Z 1 to Z 13 may be N.
- At least three of, for example Z 1 to Z 13 may be a N.
- At least one of Z 1 to Z 3 may be N.
- Z 1 to Z 3, at least one of which may be N and, ⁇ 4 to ⁇ 13 each independently represent CR a may be, in which R a is an unsubstituted C1 hydrogen, heavy hydrogen, substituted or unsubstituted To C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- At least two of Z 1 to Z 3 may be N.
- at least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be N or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted. It may be a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
- Z 1 to Z 3 may be all N, ⁇ 4 to ⁇ 13 may be each independently ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
- R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
- the organic compound may be one of the compounds listed in the following Group 2, but is not limited thereto. . .
- the aforementioned organic compound can be applied to organic optoelectronic devices.
- the aforementioned organic compounds may be applied to the organic optoelectronic device alone or in combination with other organic compounds.
- the above-mentioned organic compound is used together with other organic compounds, it can be applied in the form of a composition.
- the composition may include at least one organic compound having the above-described organic compound and a carbazole moiety.
- the above-described organic compound is referred to as a 'first organic compound' and at least one organic compound having a carbazole moiety is referred to as a 'second organic compound'.
- the second organic compound may be, for example, a compound represented by Formula 5 below.
- ⁇ ⁇ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent Heterocyclic group or a combination thereof,
- Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
- R 60 to R 63 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ,
- At least one of R 60 to R 63 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group.
- the second organic compound represented by Chemical Formula 5 may be, for example represented by at least one of 5-III in Chemical Formula 5-1.
- X ', X 4 and X 5 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, substituted Or an unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
- Ar 1 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted : C2 to C30 heterocyclic group or a combination thereof,
- R 60 to R 63 and R 6S to R 79 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocycle Groups or a combination thereof.
- the second organic compound represented by Chemical Formula 5 may be, for example, a compound listed in Group 3, but is not limited thereto.
- the second organic compound may be, for example, a compound made of a combination of a moiety represented by Formula 6 and a moiety represented by Formula 7. [Formula 6] [Formula 7]
- Y 2 and Y 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
- Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
- R 64 to R 67 are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C50 aryl group, substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,
- Adjacent two * of Formula 6 combines with two * of Formula 7 to form a fused ring, and * which does not form a fused ring in Formula 6 is each independently CR b , wherein R b is hydrogen, deuterium Or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
- the second organic compound consisting of a combination of the moiety represented by Formula 6 and the moiety represented by Formula 7 may be selected from, for example, a compound listed in Group 4 below, but is not limited thereto.
- the second organic compound may include at least one compound compound consisting of a compound represented by Chemical Formula 5 and a combination of a moiety represented by Chemical Formula 6 and a moiety represented by Chemical Formula 7.
- the composition may include the first organic compound and the second organic compound in an increase ratio of about 1: 10 to 10: 1.
- the composition may be applied to an organic layer of an organic optoelectronic device, and the first organic compound and the second organic compound may serve as a host.
- the first organic compound may be a compound having a bipolar characteristic having a relatively strong electronic property
- the second organic compound is a compound having a bipolar characteristic having a relatively strong hole characteristic, and used together with the first organic compound to transfer charges. And it is possible to further improve the luminous efficiency and lifetime characteristics by increasing the stability.
- composition may further include one or more organic compounds in addition to the first organic compound and the second organic compound described above.
- the composition may further comprise a dopant.
- the dopant may be a red, green or blue dopant, for example, a phosphorescent dopant.
- the dopant is a substance that is mixed with the first host compound and the second host compound in a small amount to emit light, and is generally a metal complex that emits light by multiple excitation which excites above a triplet state. Materials such as may be used.
- the dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.
- Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh,
- the phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.
- ⁇ is a metal
- L and X are the same or different from each other and a ligand forming a complex with ⁇ .
- the ⁇ can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, wherein L and X are, for example, bidentate It may be a ligand.
- the composition may be formed into a thin film by a dry film forming method or a solution process.
- the dry film forming method may be, for example, chemical vapor deposition, sputtering, plasma plating, and ion plating, and two or more compounds may be simultaneously formed or a compound having the same deposition temperature may be mixed and formed together.
- the solution process may be, for example, inkjet printing, spin coating, slit coating, bar coating. And / or dip coating.
- the organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy, and examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photosensitive drums.
- the organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the organic compound or the composition described above.
- the organic layer may include a light emitting layer including the organic compound or the composition.
- the organic layer may include an auxiliary layer positioned between the emission layer, the anode and the emission layer, and / or between the cathode and the emission layer, and the auxiliary layer may include the organic compound or the composition.
- an organic light emitting diode 100 includes an anode 1 10 and a cathode 120 facing each other, and an organic layer 105 positioned between the anode 1 10 and the cathode 120. ).
- the anode 1 10 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
- the anode 1 10 is, for example, a metal such as nickel, platinum, vanadium, crumb, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide ( ⁇ ),
- Metal oxides such as rhodium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene Xpolyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
- IZO rhodium zinc oxide
- Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene Xpolyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
- the cathode 120 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
- the cathode 120 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
- the organic layer 105 includes an emission layer 130 comprising the above-mentioned organic compound or the above-described composition.
- the light emitting layer 130 may include the organic compound or the composition as a host, may include the above-described organic compound alone, or may include at least two kinds of the above-described organic compounds in combination or as described above.
- the composition may be contained, or may contain a mixture of the above-mentioned organic compound or another organic compound with the above-described composition.
- the light emitting layer 130 may further include a dopant.
- the dopant may be a red, green or blue dopant, for example a phosphorescent dopant.
- the dopant is as described above.
- the organic layer 105 may further include an auxiliary layer (not shown) positioned between the anode 1 10 and the light emitting layer 130 and / or between the cathode 120 and the light emitting layer 130.
- the auxiliary layer is a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole Barrier layers or combinations thereof.
- the auxiliary layer may comprise the aforementioned organic compound or composition.
- the organic light emitting diode described above may be applied to an organic light emitting diode display. [Form for implementation of invention]
- intermediate 1-10 (45 g, 9 mmol 5 mmol) was dissolved in 0.4 L of dimethylforamide (DMF), followed by bis (pinacolato) diboron (29.7 g, 117 mmol) and ( ⁇ , ⁇ '- bis (diphenylphosphine). ) ferrocene) dichloropalladium (II) (0.80 g, 0.98 mmol) and potassium acetate (28.7 g, 293 mmol) were added and refluxed at 150 ° C for 18 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-11 (32.2 g, 65%).
- intermediate 1-9 (10 g, 19.7 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), followed by 2-chloro- purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/). 4,6-diphenyl-l, 3,5-triazine (5.27 g, 19.7 mmol)
- An organic light emitting device was manufactured using Compound 1 obtained in Synthesis Example 16 as a host and Ir (PPy) 3 as a dopant.
- ⁇ was used as a positive electrode with a thickness of 1000 A.
- Aluminum (Al) was used at a thickness of 1000 A.
- the method of manufacturing the organic light emitting device the anode is cut into a glass substrate having a sheet resistance value of 15 ⁇ / ⁇ 2 to a size of 50mm x 50 mm x 0.7 mm in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was used for 30 minutes.
- the amount of the phosphorescent dopyeon agent was deposited such that the weight 7 0 /.
- the total amount of the light-emitting layer 100 parts by weight 0/0.
- Bis (2-methyl-8- qumolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 A. Subsequently, the same vacuum deposition was performed. Alq3 was deposited under the conditions to form an electron transport layer having a thickness of 200 A. As a cathode on the electron transport layer
- LiF and A1 were sequentially deposited to manufacture an organic photoelectric device.
- the structure of the organic photoelectric device is nO / NPB (80 nm) / EML (Compound 1 (93 weight 0 /.) + Ir (PPy) 3 (7 weight 0 /.), 30 nm) / Balq (5 nm) / It was produced in the structure of Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).
- the organic light emitting diodes of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that CBP, Compound Host 1 obtained in Synthesis Example 23, and Compound Host 2 obtained in Synthesis Example 24 were used instead of Compound 1 obtained in Synthesis Example 16.
- the structure of NPB, BAlq, CBP and Ir (PPy) 3 used in the organic light emitting device is as follows.
- the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
- the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
- a luminance meter Minolta Cs-IOOOA
- the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
- Comparative Example 3 HOST2 4.3 Green 18.5
- Table 1 it can be seen that the organic light emitting diode according to Example 1 to 7 exhibits low driving voltage and high luminous efficiency compared to the organic light emitting diode according to Comparative Examples 1 to 3.
- the temperature was measured when the HOST of the light emitting layer was deposited during the manufacturing process of the organic light emitting device according to Example 1, which means a temperature at which a thickness of 1 A may be stacked per second (A / sec).
- the energy input difference was measured as a function of temperature while changing the temperature of the sample and reference using a DSC1 instrument from Metier Teledo.
- Samples of the compounds were collected lg and filled with nitrogen in a glass container and sealed. After the glass container was stored in an oven at 200 ° C. for 200 hours, the purity was measured in the same manner as the method for measuring the room temperature purity.
- HOST 2 obtained in Synthesis Example 24 is lower than the compound 3 and Synthesis 12 obtained in Synthesis Example 18 and the compound 12 obtained in Synthesis Example 19 it can be seen that the lower the glass transition temperature, the higher the deposition process temperature and lower the high temperature purity .
- Compound A was vacuum deposited on the ITO substrate using the prepared ⁇ transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on the injection layer. Depositing a thickness of 1020 A to form a hole transport layer.
- the oil-emitting light emitting device has a structure having five organic thin film layers, specifically as follows.
- the organic light emitting diodes of Examples 9 to 13 were obtained by the same method as Example 8, except for using the known compounds B-10, B-31, B-34, B-43, and E-1 instead of the compound C-10. Produced.
- Comparative Examples 4 to 9 Compound C-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-31 is used as the sole host, Compound B-34 is the sole host.
- the organic light emitting diodes of Comparative Examples 4 to 9 were prepared in the same manner as in Example 8, except that Compound B-43 was used as the sole host and Compound E-1 was the sole host. Evaluation II
- the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
- the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
- a luminance meter Minolta Cs-IOOOA
- the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
- Example 1 Compound 12 B-34 48.5 150 Example 12 Compound 12 B-43 51.0 140
- Comparative Example 9 E-1 1.4 30 Referring to Table 3, the organic light emitting diode according to Examples 8 to 13 is significantly improved in the luminous efficiency and reception characteristics compared to the organic light emitting diode according to Comparative Example 4 Nag ' 9 You can see that. In addition, it can be seen that the organic light emitting device according to Examples 8 to 13 further improved luminous efficiency and lifespan than the organic light emitting device according to the reference example.
- the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
Abstract
The present invention relates to an organic compound represented by chemical formula 1, a composition comprising the organic compound, an organic optoelectronic element comprising the organic compound and/or the composition, and a display device.
Description
【명세서】 【Specification】
【발명의 명칭】 [Name of invention]
유기 화합물, 조성물， 유기 광전자 소자 및 표시 장치 Organic Compounds, Compositions, Organic Optoelectronic Devices and Display Devices
【기술분야】 Technical Field
유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치에 관한 것이다. An organic compound, a composition, an organic optoelectronic device, and a display device.
【배경기술】 Background Art
유기 광전자 소자 (organic optoelectronic diode)는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이다. Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
유기 광전자 소자는 동작 원리에 따라 크게 두 가지로 나눌 수 있다. 하나는 광 에너지에 의해 형성된 엑시톤 (exciton)이 전자와 정공으로 분리되고 상기 전자와 정공이 각각 다른 전극으로 전달되면서 전기 에너지를 발생하는 광전 소자이고, 다른 하나는 전극에 전압 또는 전류를 공급하여 전기 Organic optoelectronic devices can be divided into two types according to the principle of operation. One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electric energy.
에너지로부터 광 에너지를 발생하는 발광 소자이다. It is a light emitting device that generates light energy from energy.
유기 광전자 소자의 예로는 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 (organic photo conductor drum) 등을 들 수 있다. Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
이 중, 유기 발광 소자 (organic light emitting diode, OLED)는 근래 평판 표시 장치 (flat panel display device)의 수요 증가에 따라 크게 주목받고 있다. 유기 발광 소자는 유기 발광 재료에 전류를 가하여 전기 에너지를 빛으로 전환시키는 소자로서, 통상 애노드와 캐소드 사이에 유기층이 삽입된 구조로 이루어져 있다. 유기 발광 소자의 성능은 유기층의 특성에 의해 영향을 많이 받으며, 그 중에서도 유기층에 포함된 유기 재료에 의해 영향을 많이 받는다. Among these, organic light emitting diodes (OLEDs) have attracted much attention recently as demand for flat panel displays increases. An organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has an organic layer interposed between an anode and a cathode. The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic material included in the organic layer.
특히 유기 발광 소자가 대형 평판 표시 장치에 적용되기 위해서는 정공 및 전자의 이동성을 높이는 동시에 전기화학적 안정성을 높일 수 있는 유기 재료의 개발이 필요하다. In particular, in order to apply the organic light emitting device to a large flat panel display, it is necessary to develop an organic material that can increase the mobility of holes and electrons and at the same time increase electrochemical stability.
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】 [Technical problem]
일 구현예는 고효율 및 장수명 유기 광전자 소자를 구현할 수 있는 유기 화합물을 제공한다. One embodiment provides an organic compound capable of implementing high efficiency and long life organic optoelectronic devices.
일 구현예는 상기 유기 화합물을 포함하는 유기광전자소자용 조성물을 제공한다.
다른 구현예는 상기 유기 화합물을 포함하는 유기 광전자 소자를 제공한다. 또 다른 구현예는 상기 유기 광전자 소자를 포함하는 표시 장치를 One embodiment provides an organic optoelectronic device composition comprising the organic compound. Another embodiment provides an organic optoelectronic device including the organic compound. Another embodiment provides a display device including the organic optoelectronic device.
제공한다. to provide.
【기술적 해결방법】 Technical Solution
일 구현예에 따르면, 하기 화학식 1로 표현되는 유기 화합물을 제공한다. 화학식 1 ] According to one embodiment, an organic compound represented by Chemical Formula 1 is provided. Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
Z1 내지 Z13은 각각 독립적으로 N 또는 CRa 이고 Z 1 to Z 13 are each independently N or CR a
Z1 내지 Z13중 적어도 하나는 N이고, At least one of Z 1 to Z 13 is N,
L1은 단일 결합 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고, L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R1 내지 R10은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C 1 내지 C 10 알킬기, 치환 또는 비치환된 C6 내지 C 12 아릴기 또는 이들의 조합이고,R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, or a combination thereof,
R1 1내지 R14 및 Ra는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C 1 내지 C 10 알킬기, 치환 또는 비치환된 C6 내지 C 12 아릴기 , 치환 또는 비치환된 C3 내지 C12 해테로고리기 또는 이들의 조합이고， R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, a substituted or unsubstituted C 3 to C 12 hate Logo or a combination thereof,
R1 내지 R14 및 Ra는 각각 독립적으로 존재하거나 인접한 두 개가 결합하여 고리를 형성하고, R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring,
nl 및 n2는 각각 독립적으로 0 내지 2의 정수이다. nl and n2 are each independently an integer of 0 to 2.
다른 구현예에 따르면, 상기 유기 화합물인 제 1 유기 화합물, 그리고 카바졸 모이어티를 가지는 적어도 하나의 게 2 유기 화합물을 포함하는 According to another embodiment, the organic compound includes a first organic compound, and at least one crab 2 organic compound having a carbazole moiety.
유기광전자소자용 조성물올 제공한다.
또 다른 구현예에 따르면, 서로 마주하는 애노드와 캐소드, 그리고 상기 애노드와 상기 캐소드 사이에 위치하는 적어도 1층의 유기층을 포함하고, 상기 유기층은 발광층, 그리고 상기 애노드와 상기 발광층 사이 또는 상기 캐소드와 상기 발광층 사이에 위치하는 보조층을 포함하며 , 상기 발광층 또는 보조층은 상기 유기 화합물 또는 상기 유기광전자소자용 조성물을 포함하는 유기 광전자 소자를 제공한다. It provides a composition for an organic optoelectronic device. According to another embodiment, an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer is a light emitting layer, and between the anode and the light emitting layer or the cathode and the An auxiliary layer is disposed between the light emitting layers, and the light emitting layer or the auxiliary layer provides an organic optoelectronic device including the organic compound or the composition for an organic optoelectronic device.
또 다른 구현예에 따르면， 상기 유기 광전자 소자를 포함하는 표시 장치를 제공한다. According to another embodiment, a display device including the organic optoelectronic device is provided.
【유리한 효과】 Advantageous Effects
고효율 장수명 유기 광전자 소자를 구현할 수 있다. High efficiency long life organic optoelectronic devices can be implemented.
【도면의 간단한 설명】 [Brief Description of Drawings]
도 1은 일 구현예에 따른 유기 발광 소자를 도시한 단면도이다. 1 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment.
【발명의 실시를 위한 최선의 형태】 [Best form for implementation of the invention]
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.
본 명세서에서 "치환 "이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 할로겐기, 히드록시기, 아미노기, 치환 또는 비치환된 C1 내지 C30 아민기， 니트로기, 치환 또는 비치환된 C1 내지 C40 실릴기, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C6 내지 C30 아릴기, C2 내지 C30 헤테로고리기, C1 내지 C20 알콕시기， 트리플루오로메틸기 등의 C1 내지 C 10 트리플루오로알킬기 또는 시아노기로 치환된 것을 의미한다. As used herein, unless otherwise defined, "substituted" means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C10 trifluoro such as C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group, C2 to C30 heterocyclic group, C1 to C20 alkoxy group, trifluoromethyl group, etc. Mean substituted by a roalkyl group or a cyano group.
일 예에서， 본 명세서의 "치환 "이란 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 치환 또는 비치환된 C1 내지 C30 아민기, 니트로기 , 치환 또는 비치환된 C 1 내지 C40 실릴기, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C6 내지 C30 아릴기 또는 C2 내지 C30 헤테로고리기로 치환된 것일 수 있다. In one embodiment, the term "substituted" herein refers to a deuterium, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C 1 to C40 silyl group, C1 to It may be substituted with a C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group or C2 to C30 heterocyclic group.
일 예에서, 본 명세서의 "치환 "이란 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소， 치환 또는 비치환된 C1 내지 C40 실릴기, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기 또는 C6 내지 C30 아릴기로 치환된 것일 수
있다. In one embodiment, "substituted" as used herein means a deuterium, a substituted or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group or C6 to C30 aryl group Can be substituted have.
또한 상기 치환된 할로겐기, 히드록시기, 아미노기, 치환 또는 비치환된 C1 내지 C20 아민기, 니트로기， 치환 또는 비치환된 C3 내지 C40 실릴기, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C6 내지 C30 아릴기, C3 내지 C30 헤테로고리기, C 1 내지 C20 알콕시기, 트리플루오로메틸기 등의 C 1 내지 C10 트리플루오로알킬기 또는 시아노기 중 인접한 두 개의 치환기가 융합되어 고리를 형성할 수도 있다. 예를 들어, 상기 치환된 C6 내지 C30 아릴기는 인접한 또 다른 치환된 C6 내지 C30 아릴기와 융합되어 치환 또는 비치환된 플루오렌 고리를 형성할 수 있다. In addition, the substituted halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to Two adjacent substituents of C 1 to C 10 trifluoroalkyl group or cyano group such as C 30 aryl group, C 3 to C 30 heterocyclic group, C 1 to C 20 alkoxy group, trifluoromethyl group, etc. may be fused to form a ring. For example, the substituted C6 to C30 aryl group may be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
본 명세서에서 "헤테로' '란 별도의 정의가 없는 한, 하나의 작용기 내에 적어도 하나의 헤테로 원자를 포함하고 나머지는 탄소인 것을 의미한다. 상기 헤테로 원자는 N, 0, S, P 및 Si 에서 선택될 수 있다. As used herein, unless otherwise defined, "hetero" 'includes at least one heteroatom in one functional group and the remainder is carbon, said heteroatom selected from N, 0, S, P and Si. Can be.
본 명세서에서 "아릴기 (aryl group)"는 카보사이클릭 방향족 모이어티를 하나 이상 갖는 그룹을 의미하며 넓게는 카보사이클릭 방향족 모이어티들이 단일 결합으로 연결된 형태 및 카보사이클릭 방향족 모이어티들이 직접 또는 As used herein, "aryl group" refers to a group having one or more carbocyclic aromatic moieties, and broadly the form in which the carbocyclic aromatic moieties are connected in a single bond and the carbocyclic aromatic moieties are directly or
간접적으로 융합된 비방향족 융합 고리 또한 포함한다. 아릴기는 모노시클릭， 폴리시클릭 또는 융합된 폴리시클릭 (즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다. Also included are indirectly fused non-aromatic fused rings. Aryl groups include monocyclic, polycyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
본 명세서에서 "헤테로고리기 (heterocyclic group)"는 아릴기， 사이클로알킬기， 이들의 융합고리 또는 이들의 조합과 같은 고리 화합물 내에 N, 0, S, P 및 Si에서 선택되는 헤테로 원자를 적어도 한 개를 함유하고, 나머지는 탄소인 것을 의미한다. 상기 해테로고리기가 융합고리인 경우, 상기 헤테로고리기 전체 또는 각각의 고리마다 헤테로 원자를 한 개 이상 포함할 수 있다. As used herein, a "heterocyclic group" refers to at least one hetero atom selected from N, 0, S, P and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof or a combination thereof. Containing, and the rest is carbon. When the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for all or each ring.
보다 구체적으로, 치환 또는 비치환된 아릴기 및 /또는 치환 또는 비치환된 헤테로 고리기는， 치환 또는 비치환된 페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 안트라세닐기, 치환 또는 비치환된 페난트릴기, 치환 또는 More specifically, a substituted or unsubstituted aryl group and / or a substituted or unsubstituted heterocyclic group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted group Substituted phenanthryl groups, substitutions or
비치환된 나프타세닐기 , 치환 또는 비치환된 피레닐기 , 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기， 치환 또는 비치환된 쿼터페닐기, 치환 또는 비치환된 크리세닐기, 치환 또는 비치환된 트리페닐레닐기, 치환 또는 비치환된 페릴레닐기, 치환 또는 비치환된 인데닐기, 치환 또는 비치환된
퓨라닐기, 치환 또는 비치환된 티오페닐기， 치환 또는 비치환된 피를릴기, 치환 또는 비치환된 피라졸릴기, 치환 또는 비치환된 이미다졸일기, 치환 또는 Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted quarterphenyl group, substituted or unsubstituted chrysenyl group, substituted or Unsubstituted triphenylenyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted Furanyl groups, substituted or unsubstituted thiophenyl groups, substituted or unsubstituted pyrylyl groups, substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted imidazolyl groups, substituted or
비치환된 트리아졸일기, 치환 또는 비치환된 옥사졸일기, 치환또는 비치환된 티아졸일기, 치환 또는 비치환된 옥사디아졸일기， 치환 또는 비치환된 Unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted
티아디아졸일기, 치환 또는 비치환된 피리디닐기, 치환 또는 비치환된 Thiadiazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted
피리미디닐기, 치환 또는 비치환된 피라지닐기, 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 벤조퓨라닐기, 치환 또는 비치환된 벤조티오페닐기， 치환 또는 비치환된 벤즈이미다졸일기, 치환 또는 비치환된 인돌일기, 치환 또는 비치환된 퀴놀리닐기, 치환 또는 비치환된 이소퀴놀리닐기, 치환 또는 비치환된 퀴나졸리닐기, 치환 또는 비치환된 퀴녹살리닐기, 치환 또는 비치환된 Pyrimidinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted triazinyl groups, substituted or unsubstituted benzofuranyl groups, substituted or unsubstituted benzothiophenyl groups, substituted or unsubstituted benzimidazolyl groups, Substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted
나프티리디닐기， 치환 또는 비치환된 벤즈옥사진일기, 치환 또는 비치환된 벤즈티아진일기, 치환 또는 비치환된 아크리디닐기, 치환 또는 비치환된 Naphthyridinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted
페나진일기, 치환 또는 비치환된 페노티아진일기, 치환 또는 비치환된 Phenazineyl group, substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted
페녹사진일기， 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 Phenoxazineyl, substituted or unsubstituted fluorenyl group, substituted or unsubstituted
디벤조퓨란일기, 치환 또는 비치환된 디벤조티오페닐기， 치환 또는 비치환된 카바졸기, 이들의 조합 또는 이들의 조합이 융합된 형태일 수 있으나, 이에 제한되지는 않는다. A dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a combination thereof, or a combination thereof may be in a fused form, but is not limited thereto.
본 발명의 일 예에서, 치환 또는 비치환된 아릴기는 치환 또는 비치환된 페닐기， 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 쿼터페닐기 또는 치환 또는 비치환된 플루오레닐기일 수 있다. In one embodiment of the present invention, the substituted or unsubstituted aryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted It may be a quarterphenyl group or a substituted or unsubstituted fluorenyl group.
본 발명의 일 예에서， 치환 또는 비치환된 인데닐기, 치환 또는 비치환된 피리디닐기, 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 피라지닐기， 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 인돌일기， 치환 또는 비치환된 퀴놀리닐기, 치환 또는 비치환된 이소퀴놀리닐기, 치환 또는 비치환된 퀴나졸리닐기, 치환 또는 비치환된 퀴녹살리닐기, 치환 또는 비치환된 In one embodiment of the present invention, a substituted or unsubstituted indenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group , Substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Done
디벤조퓨란일기, 치환 또는 비치환된 디밴조티오페닐기, 치환 또는 비치환된 카바졸기, 이들의 조합 또는 이들의 조합이 융합된 형태일 수 있으나, 이에' 제한되지는 않는다ᅳ Dibenzofuran group, may be a substituted or unsubstituted di banjo a thiophenyl group, a substituted or unsubstituted carbazole, a combination thereof or a combination thereof fused form, but is not The "May eu
본 명세서에서, 정공 특성이란, 전기장 (electric field)을 가했을 때 전자를
공여하여 정공을 형성할 수 있는 특성을 말하는 것으로 , HOMO 준위를 따라 전도 특성을 가져 양극에서 형성된 정공의 발광층으로의 주입, 발광층에서 형성된 정공의 양극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성올 의미한다. 또한 전자 특성이란, 전기장을 가했을 때 전자를 받을 수 있는 특성을 말하는 것으로, LUMO 준위를 따라 전도 특성을 가져 음극에서 형성된 전자의 발광층으로의 주입, 발광층에서 형성된 전자의 음극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. In the present specification, the hole characteristic refers to electrons when an electric field is applied. It refers to a property that can form holes by donating, and has conductivity characteristics along the HOMO level to facilitate injection of holes formed in the anode into the light emitting layer, movement of holes formed in the light emitting layer into the anode, and movement in the light emitting layer. Means to come. In addition, the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
이하 일 구현예에 따른 유기 화합물을 설명한다. Hereinafter, an organic compound according to one embodiment is described.
일 구현예에 따른 유기 화합물은 하기 화학식 1로 표현될 수 있다. An organic compound according to one embodiment may be represented by Formula 1 below.
화학식 1] [Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
Z1 내지 Z13은 각각 독립적으로 N 또는 CRa 이고, Z 1 to Z 13 are each independently N or CR a ,
Z1 내지 Z13중 적어도 하나는 N이고， At least one of Z 1 to Z 13 is N,
L1은 단일 결합 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고,L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R1 내지 R10은 각각 독립적으로 수소, 중수소， 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기 또는 이들의 조합이고,R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
R1 1 내지 R14 및 Ra는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 '해테로고리기 또는 이들의 조합이고, R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 'heterocyclic group Or a combination thereof,
R1 내지 R14 및 Ra는 각각 독립적으로 존재하거나 인접한 두 개가 결합하여 고리를 형성하고,
nl 및 n2는 각각 독립적으로 0 내지 2의 정수이다. R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring, nl and n2 are each independently an integer of 0 to 2.
상기 유기 화합물은 다이벤조퀴녹살린 (dibenzoquinoxaline) 모이어티와 적어도 하나의 질소를 가진 고리를 포함함으로써 전기장 인가시 전자를 받기 쉬운 구조가 될 수 있고, 이에 따라 상기 유기 화합물을 적용한 유기 광전자 소자의 구동 전압올 낮추고 효율을 높일 수 있다. The organic compound may include a dibenzoquinoxaline moiety and a ring having at least one nitrogen, and thus may have a structure in which electrons are easily received when an electric field is applied, and thus driving voltage of the organic optoelectronic device to which the organic compound is applied. This can lower the efficiency and increase efficiency.
Gaussian 09를 사용하여 B3LYP/6-31G** 방법으로 계산된 상기 유기 화합물의 LUMO 에너지는 예컨대 -1.5eV 내지 -2.0eV일 수 있다. 상기 범위 내에서 예컨대 약 1.7eV 내지 -1.8eV일 수 있다. The LUMO energy of the organic compound calculated by the B3LYP / 6-31G ** method using Gaussian 09 can be, for example, -1.5 eV to -2.0 eV. Within this range, for example, about 1.7 eV to -1.8 eV.
또한 상기 유기 화합물은 다이벤조퀴녹살린을 중심으로 한쪽으로 뻗은 질소 함유 고리 치환기를 포함함으로써 비대칭 구조를 구현할 수 있고 이에 따라 분자의 상호 작용을 억제하여 결정성을 낮출 수 있다. In addition, the organic compound may implement an asymmetric structure by including a nitrogen-containing ring substituent that extends to one side about the dibenzoquinoxaline, thereby lowering the crystallinity by inhibiting the interaction of molecules.
또한 상기 유기 화합물은 비대칭 구조를 가짐으로써 분자들의 In addition, the organic compound has an asymmetric structure so that
스태킹 (stacking)을 효과적으로 방지하여 공정 안정성을 높이는 동시에 증착 온도를 낮출 수 있다. Effectively preventing stacking can increase process stability while lowering the deposition temperature.
상기 화학식 1에서, 예컨대 Z1 내지 Z13중 적어도 두 개는 N일 수 있다. 상기 화학식 1에서, 예컨대 Z1 내지 Z13중 적어도 세 개는 N일 수 있다. 상기 화학식 1에서, 예컨대 Z1 내지 Z3중 적어도 하나는 N일 수 있다. 상기 화학식 1에서, 예컨대 } 내지 Z3 중 적어도 하나는 N일 수 있으며, Z4 내지 Z13 각각 독립적으로 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내자 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. 상기 화학식 1에서, 예컨대 Z1 내지 Z3중 적어도 둘은 N일 수 있다. In Formula 1, for example, at least two of Z 1 to Z 13 may be N. In Formula 1, for example, at least three of Z 1 to Z 13 may be N. In Formula 1, for example, at least one of Z 1 to Z 3 may be N. In Formula 1, for example, at least one of} to Z 3 may be N, and each of Z 4 to Z 13 may independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group. , A substituted or unsubstituted C6 internal C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof. In Formula 1, for example, at least two of Z 1 to Z 3 may be N.
상기 화학식 1에서, 예컨대 Z1 내지 Z3 중 적어도 둘은 N일 수 있으며 , Ζ4 내지 ζ13 각각 독립적으로 Ν 또는 CRa일 수 있고, 여기서 Ra는 수소, 증수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In Formula 1, for example, at least two of Z 1 to Z 3 may be N, and each of Ζ 4 to ζ 13 may independently be N or CR a , wherein R a is hydrogen, hydrogen, substituted or unsubstituted. Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
상기 화학식 1에서, 예컨대 Z1 내지 Z3는 모두 N일 수 있고 , Ζ4 내지 Ζ13은 각각 독립적으로 Ν 또는 CRa일 수 있고, 여기서 Ra는 수소, 중수소， 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환
또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In Chemical Formula 1, for example, Z 1 to Z 3 may be all N, Ζ 4 to Ζ 13 may be each independently Ν or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted Or an unsubstituted C3 to C12 heterocyclic group or a combination thereof.
상기 화학식 1에서, R1 내지 R4는 예컨대 각각 독립적으로 수소, 중수소 또는 치환 또는 비치환된 C1 내지 C10 알킬기일 수 있고, R1 내지 R4는 예컨대 각각 독립적으로 수소일 수 있다. In Formula 1, R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
상기 화학식 1에서, L1은 예컨대 단일 결합이거나 적어도 하나의 꺾임 (kink) 구조를 가질 수 있다. 여기서 꺾임 구조는 두 개의 연결 부분들이 직선 구조를 이루지 않는 구조를 말하는 것으로, 예컨대 페닐렌기의 경우 연결 부분들이 직선 구조를 이루지 않는 올쏘 페닐렌 (o-phenylene)과 메타 페닐렌 (m-phenylene)이 꺾임 구조를 가지며， 연결 부분들이 직선 구조를 이루는 파라 페닐렌 (p-phenylene)은 꺾임 구조를 가지지 않는다. In Formula 1, L 1 may be, for example, a single bond or have at least one kink structure. Here, the fold structure refers to a structure in which two connecting portions do not form a straight structure. For example, in the case of a phenylene group, o-phenylene and meta-phenylene, in which the connecting portions do not form a straight structure, are represented. P-phenylene having a folding structure and the connecting portions forming a straight structure does not have a bending structure.
상기 화학식 1에서, L1은 예컨대 단일 결합, 꺾임 구조의 치환 또는 비치환된 페닐렌기, 꺾임 구조의 치환 또는 비치환된 바이페닐렌기, 꺾임 구조의 치환 또는 비치환된 터페닐렌기, 꺾임구조의 치환 또는 비치환된 쿼터페닐렌기， 꺾임구조의 치환 또는 비치환된 펜타페닐렌기일 수 있다. In Formula 1, L 1 is, for example, a single bond, a substituted or unsubstituted phenylene group having a folding structure, a substituted or unsubstituted biphenylene group having a folding structure, a substituted or unsubstituted terphenylene group having a folding structure, a folding structure It may be a substituted or unsubstituted quarterphenylene group, a substituted or unsubstituted pentaphenylene group having a folding structure.
상기 화학식 1에서, L1은 예컨대 단일 결합이거나 치환 또는 비치환된 0- 페닐렌기 및 치환 또는 비치환된 m-페닐렌기 중 적어도 하나를 포함할 수 있다. 상기 화학식 1에서, L1은 예컨대 단일 결합이거나 하기 그룹 1에 나열된 치환 또는 비치환된 기에서 선택된 하나일 수 있다.
In Formula 1, L 1 may include, for example, at least one of a single bond or a substituted or unsubstituted 0-phenylene group and a substituted or unsubstituted m-phenylene group. In Formula 1, L 1 may be, for example, a single bond or one selected from substituted or unsubstituted groups listed in Group 1 below.
상기 그룹 1에서, In group 1 above,
R30 내지 R57은 각각 독립적으로 수소, 중수소， 치환 또는 비치환된 C1 내지 C10 알킬기， 치환 또는 비치환된 C3 내지 C30 사이클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 헤테로고리기， 치환 또는 비치환된 아민기 , 치환 또는 비치환된 C6 내지 C30 아릴아민기 , 치환 또는 비치환된 C6 내지 C30 해테로아릴아민기, 치환 또는 비치환된 C1 내지 C30 알콕시기, 할로겐, 시아노기, 히드록실기, 아미노기,니트로기， 카르복실기, 페로세닐기 또는 이들의 조합이다. R 30 to R 57 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 heteroarylamine group, substituted or unsubstituted C1 to C30 alkoxy Group, halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, ferrocenyl group, or a combination thereof.
상기 유기 화합물의 분자량은 예컨대 약 750 이하일 수 있다. 상기 범위 내에서 약 538 이상 750 미만일 수 있다. 상기 범위의 분자량을 가짐으로써 증착 공정시 높은 온도에 의해 유기 화합물이 열분해되는 것을 감소시키고 내열성을 개선할 수 있다. 상기 범위 내에서 약 538 내지 749 일 수 있고， 상기 범위 내에서 약 550 내지 730 일 수 있고, 상기 범위 내에서 약 600 내지 700일 수 있다. The molecular weight of the organic compound may be, for example, about 750 or less. Within this range may be greater than or equal to about 538 and less than 750. By having a molecular weight in the above range it is possible to reduce the thermal decomposition of the organic compound by the high temperature during the deposition process and to improve the heat resistance. It may be about 538 to 749 within the range, may be about 550 to 730 within the range, may be about 600 to 700 within the range.
상기 유기 화합물은 예컨대 하기 화학식 2로 표현될 수 있다.
The organic compound may be represented by, for example, the following Chemical Formula 2.
상기 화학식 2에서， In Chemical Formula 2,
Ζ1 내지 Z^ R1 내지 R14, nl 및 n2는 전술한 바와 같고, Ζ 1 to Z ^ R 1 to R 14 , nl and n 2 are as described above,
R15 내지 R17은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있고, R 15 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof Can,
n3 및 n4는 각각 독립적으로 0 내자 2의 정수일 수 있다. n3 and n4 may be each independently an integer of 0 to 2.
상기 화학식 2에서， 예컨대 nl+n2+n3+n4≥2 일 수 있다. In Formula 2, for example, nl + n2 + n3 + n4 ≧ 2.
상기 화학식 2에서 예컨대 Z1 내지 Z13중 적어도 두 개는 N일 수 있다. 상기 화학식 2에서 예컨대 Z1 내지 Z13중 적어도 세 개는 N일 수 있다. 상기 화학식 2에서 예컨대 Z1 내지 Z3중 적어도 하나는 N일 수 있다. 상기 화학식 2에서 예컨대 Z1 내지 Z3 중 적어도 하나는 N일 수 있으며, Z4 내지 Z13 각각 독립적으로 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. 상기 화학식 2에서, 예컨대 Z1 내지 Z3중 적어도 둘은 N일 수 있다. 상기 화학식 2에서, 예컨대 Z1 내지 Z3 중 적어도 둘은 N일 수 있으며 , Ζ4 내지 ζ13 각각 독립적으로 Ν 또는 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다.
상기 화학식 2에서, 예컨대 Z1 내지 Z3는 모두 N일 수 있고， Z4 내지 Z13은 각각 독립적으로 N 또는 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In Formula 2, for example, at least two of Z 1 to Z 13 may be N. In Formula 2, for example, at least three of Z 1 to Z 13 may be N. In Formula 2, for example, at least one of Z 1 to Z 3 may be N. In Formula 2, for example, at least one of Z 1 to Z 3 may be N, and Z 4 to Z 13 may each independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group , A substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof. In Formula 2, for example, at least two of Z 1 to Z 3 may be N. In Formula 2, for example, at least two of Z 1 to Z 3 may be N, and each of Ζ 4 to ζ 13 may independently be Ν or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1. To C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof. In Chemical Formula 2, for example, Z 1 to Z 3 may be all N, Z 4 to Z 13 may be each independently N or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1 to It may be a C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
상기 화학식 2에서, R1 내지 R4는 예컨대 각각 독립적으로 수소, 중수소 또는 치환 또는 비치환된 C1 내지 C10 알킬기일 수 있고， R1 내지 R4는 예컨대 각각 독립적으로 수소일 수 있다. In Formula 2, R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
상기 유기 화합물은 예컨대 하기 화학식 3 또는 4로 표현될 수 있다. The organic compound may be represented by, for example, the following Chemical Formula 3 or 4.
상기 화학식 3 또는 4에서 , Ζ1 내지 Z^ R1 내지 R17, nl 내지 n4는 전술한 바와 같다.
상기 화학식 3 또는 4에서 예컨대 nl+n2+n3+n4≥2 일 수 있다. 상기 화학식 3 또는 4에서 예컨대 Z1 내지 Z13중 적어도 두 개는 N일 수 있다. In Formula 3 or 4, X 1 to Z ^ R 1 to R 17 , nl to n4 are as described above. In Formula 3 or 4, for example, nl + n2 + n3 + n4 ≧ 2. In Formula 3 or 4, for example, at least two of Z 1 to Z 13 may be N.
상기 화학식 3 또는 4에서 : 예컨대 Z1 내지 Z13중 적어도 세 개는 N일 수 있다. In the formula 3 or 4: at least three of, for example Z 1 to Z 13 may be a N.
상기 화학식 3 또는 4에서 : 예컨대 Z1 내지 Z3중 적어도 하나는 N일 수 있다. In the formula 3 or 4: for example, at least one of Z 1 to Z 3 may be N.
상기 화학식 3 또는 4에서: 예컨대 Z1 내지 Z3 중 적어도 하나는 N일 수 있으며 , Ζ4 내지 Ζ13 각각 독립적으로 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In the formula 3 or 4: for example, Z 1 to Z 3, at least one of which may be N and, Ζ 4 to Ζ 13 each independently represent CR a may be, in which R a is an unsubstituted C1 hydrogen, heavy hydrogen, substituted or unsubstituted To C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
상기 화학식 3 또는 4에서, 예컨대 Z1 내지 Z3중 적어도 둘은 N일 수 있다. 상기 화학식 3 또는 4에서, 예컨대 Z1 내지 Z3 중 적어도 둘은 N일 수 있으며 , Ζ4 내지 Ζ13 각각 독립적으로 Ν 또는 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In Formula 3 or 4, for example, at least two of Z 1 to Z 3 may be N. In Formula 3 or 4, for example, at least two of Z 1 to Z 3 may be N, and each of Ζ 4 to Ζ 13 may independently be N or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted. It may be a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
상기 화학식 3 또는 4에서, 예컨대 Z1 내지 Z3는 모두 N일 수 있고 , Ζ4 내지 Ζ13은 각각 독립적으로 Ν 또는 CRa일 수 있고, 여기서 Ra는 수소, 중수소, 치환 또는 비치환된 C1 내자 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합일 수 있다. In Formula 3 or 4, for example, Z 1 to Z 3 may be all N, Ζ 4 to Ζ 13 may be each independently Ν or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
상기 화학식 3 또는 4에서， R1 내지 R4는 예컨대 각각 독립적으로 수소, 중수소 또는 치환 또는 비치환된 C1 내지 C10 알킬기일 수 있고, R1 내지 R4는 예컨대 각각 독립적으로 수소일 수 있다. In Formula 3 or 4, R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
상기 유기 화합물은 하기 그룹 2에 나열된 화합물 중 하나일 수 있으나, 이에 한정되는 것은 아니다. . .
The organic compound may be one of the compounds listed in the following Group 2, but is not limited thereto. . .
TZSOlO/9lOZaM/X3d
TZSOlO / 9lOZaM / X3d
TIS0T0/9T0^HX/I3d 9^0Ϊ/-Ϊ0∑: OAV
TIS0T0 / 9T0 ^ HX / I3d 9 ^ 0Ϊ / -Ϊ0∑: OAV
상술한 유기 화합물은 단독으로 또는 다른 유기 화합물과 함께 유기 광전자 소자에 적용될 수 있다. 상술한 유기 화합물이 다른 유기 화합물과 함께 사용되는 경우, 조성물의 형태로 적용될 수 있다ᅳ The aforementioned organic compounds may be applied to the organic optoelectronic device alone or in combination with other organic compounds. When the above-mentioned organic compound is used together with other organic compounds, it can be applied in the form of a composition.
이하, 상술한 유기 화합물을 포함하는 유기 광전자 소자용 조성물의 일
예를 설명한다. Hereinafter, one of the composition for organic optoelectronic devices containing the above-described organic compound Explain the example.
상기 유기 광전자 소자용 조성물의 일 예로, 상술한 유기 화합물과 카바졸 모이어티를 가지는 적어도 하나의 유기 화합물을 포함하는 조성물일 수 있다. 이하에서 상술한 유기 화합물은 '제 1 유기 화합물 '하고 카바졸 모이어티를 가지는 적어도 하나의 유기 화합물은 '제 2 유기 화합물' 이라 한다. As an example of the composition for an organic optoelectronic device, the composition may include at least one organic compound having the above-described organic compound and a carbazole moiety. Hereinafter, the above-described organic compound is referred to as a 'first organic compound' and at least one organic compound having a carbazole moiety is referred to as a 'second organic compound'.
상기 제 2 유기 화합물은 예컨대 하기 화학식 5로 표현되는 화합물일 수 있다. The second organic compound may be, for example, a compound represented by Formula 5 below.
[화학식 5] [Formula 5]
Ar' Ar '
상기 화학식 5에서, In Chemical Formula 5,
γΐ은 단일 결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C2 내지 C20 알케닐렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기 또는 이들의 조합이고, Ar1은 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 헤테로고리기 또는 이들의 조합이고, γ ΐ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent Heterocyclic group or a combination thereof, Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
R60 내지 R63은 각각 독립적으로 수소, 중수소， 치환 또는 비치환된 C1 내지 C20 알킬기 , 치환 또는 비치환된 C6 내지 C50 아릴기 , 치환 또는 비치환된 C2 내지 C50 헤테로고리기 또는 이들의 조합이고, R 60 to R 63 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ,
R60 내지 R63 및 Ar1 중 적어도 하나는 치환 또는 비치환된 트리페닐렌기 또는 치환 또는 비치환된 카바졸릴기를 포함한다. At least one of R 60 to R 63 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group.
상기 화학식 5로 표현되는 계 2 유기 화합물은 예컨대 하기 화학식 5-1 내 5-III 중 적어도 하나로 표현될 수 있다.
[ The second organic compound represented by Chemical Formula 5 may be, for example represented by at least one of 5-III in Chemical Formula 5-1. [
상기 화학식 5-1 내지 5-ΙΠ에서, In Chemical Formulas 5-1 to 5-ΙΠ,
Υ', Υ4 및 Υ5는 각각 독립적으로 단일 결합， 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C2 내지 C20 알케닐렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기 또는 이들의 조합이고, X ', X 4 and X 5 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, substituted Or an unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
Ar1 및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 : C2 내지 C30 헤테로고리기 또는 이들의 조합이고, Ar 1 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted : C2 to C30 heterocyclic group or a combination thereof,
R60 내지 R63및 R6S 내지 R79는각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C50 아릴기, 치환 또는 비치환된 C2 내지 C50 헤테로고리기 또는 이들의 조합이다. R 60 to R 63 and R 6S to R 79 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocycle Groups or a combination thereof.
상기 화학식 5로 표현되는 게 2 유기 화합물은 예컨대 그룹 3에 나열된 화합물일 수 있으나, 이에 한정되는 것은 아니다.
The second organic compound represented by Chemical Formula 5 may be, for example, a compound listed in Group 3, but is not limited thereto.
[e 불 ΤΓ] [e fire ΤΓ]
81 81
TZS0l0/9l0ZaM/X3d
TZS0l0 / 9l0ZaM / X3d
TZSOlO/9lOZaM/X3d
TZSOlO / 9lOZaM / X3d
-a SS-9 -a SS-9
oz oz
TIS0T0/9T0^HX/I3d 9^0Ϊ/-Ϊ0∑: OAV
TIS0T0 / 9T0 ^ HX / I3d 9 ^ 0Ϊ / -Ϊ0∑: OAV
TZSOlO/9lOZaM/X3d
TZSOlO / 9lOZaM / X3d
TZSOlO/9lOZaM/X3d
TZSOlO / 9lOZaM / X3d
B-103 8-104 B-105
B-103 8-104 B-105
TIS0T0/9T0^HX/I3d 9^0Ϊ/-Ϊ0∑: OAV
TIS0T0 / 9T0 ^ HX / I3d 9 ^ 0Ϊ / -Ϊ0∑: OAV
52 52
TIS0T0/9T0^HX/I3d 9^0Ϊ/-Ϊ0∑: OAV
TIS0T0 / 9T0 ^ HX / I3d 9 ^ 0Ϊ / -Ϊ0∑: OAV
상기 제 2 유기 화합물은 예컨대 하기 화학식 6으로 표현되는 모이어티와 학식 7로 표현되는 모이어티의 조합으로 이루어진 화합물일 수 있다. [화학식 6] [화학식 7]The second organic compound may be, for example, a compound made of a combination of a moiety represented by Formula 6 and a moiety represented by Formula 7. [Formula 6] [Formula 7]
Y2 및 Y3는 각각 독립적으로 단일 결합， 치환 또는 비치환된 C1 내지 C20 알킬렌기， 치환 또는 비치환된 C2 내지 C20 알케닐렌기， 치환 또는 비치환된 C6 내지 C30 아릴렌기, 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기 또는 이들의 조합이고， Y 2 and Y 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
Ar2 및 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기， 치환 또는 비치환된 C2 내지 C30 헤테로고리기 또는 이들의 조합이고, Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
R64 내지 R67은 각각 독립적으로 수소， 증수소， 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C50 아릴기, 치환 또는 비치환된 C2 내지 C50 해테로고리기 또는 이들의 조합이고， R 64 to R 67 are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C50 aryl group, substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,
상기 화학식 6의 인접한 두 개의 *는 상기 화학식 7의 두 개의 *와 결합하여 융합고리를 형성하고 상기 화학식 6에서 융합고리를 형성하지 않은 *는 각각 독립적으로 CRb이고， 여기서 Rb는 수소, 중수소， 치환 또는 비치환된 C1 내지 C10 알킬기， 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합이다. Adjacent two * of Formula 6 combines with two * of Formula 7 to form a fused ring, and * which does not form a fused ring in Formula 6 is each independently CR b , wherein R b is hydrogen, deuterium Or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
상기 화학식 6으로 표현되는 모이어티와상기 화학식 7로 표현되는 모이어티의 조합으로 이루어진 제 2 유기 화합물은 예컨대 하기 그룹 4에 나열된 화합물에서 선택될 수 있으나, 이에 한정되는 것은 아니다. The second organic compound consisting of a combination of the moiety represented by Formula 6 and the moiety represented by Formula 7 may be selected from, for example, a compound listed in Group 4 below, but is not limited thereto.
그룹 4] Group 4]
RECTIFIED SHEET (RULE 91 ) ISA/KR
RECTIFIED SHEET (RULE 91) ISA / KR
RECTIFIED SHEET (RULE 91) ISA/'KR
RECTIFIED SHEET (RULE 91) ISA / 'KR
상기 제 2 유기 화합물은 상기 화학식 5로 표현되는 화합물 및 하기 화학식 6으로 표현되는 모이어티와 하기 화학식 7로 표현되는 모이어티의 조합으로 이루어진 화합물 증 적어도 하나를 포함할 수 있다. The second organic compound may include at least one compound compound consisting of a compound represented by Chemical Formula 5 and a combination of a moiety represented by Chemical Formula 6 and a moiety represented by Chemical Formula 7.
상기 조성물은 제 1 유기 화합물과 제 2 유기 화합물을 약 1 : 10 내지 10: 1의 증량비로 포함할 수 있다. The composition may include the first organic compound and the second organic compound in an increase ratio of about 1: 10 to 10: 1.
상기 조성물은 유기 광전자 소자의 유기층에 적용될 수 있으며, 제 1 유기 화합물과 제 2 유기 화합물은 호스트 (host)로서 역할을 할 수 있다. 이 때 제 1 유기 화합물은 전자 특성이 상대적으로 강한 바이폴라 특성을 가지는 화합물일 수 있고 제 2 유기 화합물은 정공 특성이 상대적으로 강한 바이폴라 특성을 가지는 화합물로, 제 1 유기 화합물과 함께 사용되어 전하의 이동성 및 안정성을 높임으로써 발광 효율 및 수명 특성을 더욱 개선시킬 수 있다. The composition may be applied to an organic layer of an organic optoelectronic device, and the first organic compound and the second organic compound may serve as a host. In this case, the first organic compound may be a compound having a bipolar characteristic having a relatively strong electronic property, and the second organic compound is a compound having a bipolar characteristic having a relatively strong hole characteristic, and used together with the first organic compound to transfer charges. And it is possible to further improve the luminous efficiency and lifetime characteristics by increasing the stability.
상기 조성물은 전술한 제 1 유기 화합물과 제 2 유기 화합물 외에 1종 이상의 유기 화합물을 더 포함할 수 있다. The composition may further include one or more organic compounds in addition to the first organic compound and the second organic compound described above.
상기 조성물은 도펀트를 더 포함할 수 있다. 상기 도펀트는 적색， 녹색 또는 청색의 도펀트일 수 있으며, 예컨대 인광 도펀트일 수 있다. The composition may further comprise a dopant. The dopant may be a red, green or blue dopant, for example, a phosphorescent dopant.
상기 도편트는 상기 제 1 호스트 화합물과 상기 제 2 호스트 화합물에 미량 혼합되어 발광을 일으키는 물질로, 일반적으로 삼중항 상태 이상으로 여기시키는 다중항 여기 (multiple excitation)에 의해 발광하는 금속 착체 (metal complex)와 같은 물질이 사용될 수 있다. 상기 도펀트는 예컨대 무기， 유기, 유무기 화합물일 수 있으며， 1종 또는 2종 이상 포함될 수 있다. The dopant is a substance that is mixed with the first host compound and the second host compound in a small amount to emit light, and is generally a metal complex that emits light by multiple excitation which excites above a triplet state. Materials such as may be used. The dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.
상기 인광 도편트의 예로는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh,
RECTIFIED SHEET (RULE 91 ) iSA/KR
Pd 또는 이들의 조합을 포함하는 유기 금속화합물을 들 수 있다. 상기 인광 도편트는 예컨대 하기 화학식 Z로 표현되는 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다. RECTIFIED SHEET (RULE 91) iSA / KR And organometallic compounds containing Pd or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.
[화학식 Z] [Formula Z]
L2MX L 2 MX
상기 화학식 Z에서 , Μ은 금속이고， L 및 X는 서로 같거나 다르며 Μ과 착화합물을 형성하는 리간드이다. In the above formula Z, Μ is a metal, L and X are the same or different from each other and a ligand forming a complex with Μ.
상기 Μ은 예컨대 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd또는 이들의 조합일 수 있고, 상기 L 및 X는 예컨대 바이덴테이트 리간드일 수 있다. 상기 조성물은 건식 성막법 또는 용액 공정으로 박막으로 형성될 수 있다. 상기 건식 성막법은 예컨대 화학기상증착법, 스퍼터링, 플라즈마 도금 및 이온도금 일 수 있고, 둘 이상의 화합물을 동시에 성막하거나 증착 온도가 같은 화합물을 흔합하여 같이 성막할 수 있다. 상기 용액 공정은 예컨대 잉크젯 인쇄, 스핀 코팅, 슬릿 코팅, 바 코팅 .및/또는 딥 코팅일 수 있다. The Μ can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, wherein L and X are, for example, bidentate It may be a ligand. The composition may be formed into a thin film by a dry film forming method or a solution process. The dry film forming method may be, for example, chemical vapor deposition, sputtering, plasma plating, and ion plating, and two or more compounds may be simultaneously formed or a compound having the same deposition temperature may be mixed and formed together. The solution process may be, for example, inkjet printing, spin coating, slit coating, bar coating. And / or dip coating.
이하 상술한 유기 화합물 또는 상술한 조성물을 적용한 유기 광전자 소자를 설명한다. Hereinafter, an organic optoelectronic device to which the above-described organic compound or the above-described composition is applied will be described.
상기 유기 광전자 소자는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이면 특별히 한정되지 않으며, 예컨대 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 등을 들 수 있다. The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy, and examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photosensitive drums.
상기 유기 광전자 소자는 서로 마주하는 애노드와 캐소드, 그리고 상기 애노드와 상기 캐소드 사이에 위치하는 적어도 1층의 유기층을 포함할 수 있고, 상기 유기층은 전술한 유기 화합물 또는 전술한 조성물올 포함할 수 있다. The organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the organic compound or the composition described above.
일 예로, 상기 유기층은 상기 유기 화합물 또는 상기 조성물을 포함하는 발광층을 포함할 수 있다. For example, the organic layer may include a light emitting layer including the organic compound or the composition.
일 예로, 상기 유기층은 발광층, 애노드와 발광층 사이 및 /또는 캐소드와 발광층 사이에 위치하는 보조층을 포함할 수 있고, 상기 보조층은 상기 유기 화합물 또는 상기 조성물을 포함할 수 있다. For example, the organic layer may include an auxiliary layer positioned between the emission layer, the anode and the emission layer, and / or between the cathode and the emission layer, and the auxiliary layer may include the organic compound or the composition.
여기서는 유기 광전자 소자의 일 예인 유기 발광 소자를 도면을 참고하여 설명한다. Herein, an organic light emitting diode as an example of an organic optoelectronic device will be described with reference to the drawings.
도 1은 일 구현예에 따른 유기 발광 소자를 보여주는 단면도이다.
도 1을 참고하면, 일 구현예에 따른 유기 발광 소자 (100)는 서로 마주하는 애노드 (1 10)와 캐소드 (120)， 그리고 애노드 (1 10)와 캐소드 (120) 사이에 위치하는 유기층 (105)을 포함한다. 1 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment. Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 1 10 and a cathode 120 facing each other, and an organic layer 105 positioned between the anode 1 10 and the cathode 120. ).
애노드 (1 10)는 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 예컨대 금속, 금속 산화물 및 /또는 도전성 고분자로 만들어질 수 있다. 애노드 (1 10)는 예컨대 니켈, 백금, 바나듐, 크름， 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐주석산화물 (ΠΌ), The anode 1 10 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example. The anode 1 10 is, for example, a metal such as nickel, platinum, vanadium, crumb, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (ΠΌ),
인듬아연산화물 (IZO)과 같은 금속 산화물; ZnO와 A1 또는 Sn02와 Sb와 같은 금속과 산화물의 조합; 폴리 (3-메틸티오펜), 폴리 (3,4- (에틸렌 -1 ,2- 디옥시)티오펜 Xpolyehtylenedioxythiophene: PEDOT), 폴리피롤 및 폴리아닐린과 같은 도전성 고분자 등을 들 수 있으나, 이에 한정되는 것은 아니다. Metal oxides such as rhodium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene Xpolyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
캐소드 (120)는 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며， 예컨대 금속, 금속 산화물 및 /또는 도전성 고분자로 만들어질 수 있다. 캐소드 (120)은 예컨대 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은， 주석, 납, 세슘, 바륨 등과 같은 금속 또는 이들의 합금; LiF/Al, Li02/Al, LiF/Ca, LiF/Al 및 BaF2/Ca과 같은 다층 구조 물질을 들 수 있으나, 이에 한정되는 것은 아니다. The cathode 120 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example. The cathode 120 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
유기층 (105)은 전술한 유기 화합물 또는 전술한 조성물을 포함하는 발광층 (130)을 포함한다. The organic layer 105 includes an emission layer 130 comprising the above-mentioned organic compound or the above-described composition.
발광층 (130)은 호스트 (host)로서 상기 유기 화합물 또는 상기 조성물을 포함할 수 있으며, 전술한 유기 화합물을 단독으로 포함할 수도 있고 전술한 유기 화합물 중 적어도 두 종류를 흔합하여 포함할 수도 있고 전술한 조성물올 포함할 수도 있고 전술한 유기 화합물 또는 전술한 조성물과 다른 유기 화합물올 흔합하여 포함할 수도 있다. The light emitting layer 130 may include the organic compound or the composition as a host, may include the above-described organic compound alone, or may include at least two kinds of the above-described organic compounds in combination or as described above. The composition may be contained, or may contain a mixture of the above-mentioned organic compound or another organic compound with the above-described composition.
발광층 (130)은 도편트 (dopant)를 더 포함할 수 있다. 상기 도편트는 적색， 녹색 또는 청색의 도편트일 수 있으며, 예컨대 인광 도편트일 수 있다. 도편트는 전술한 바와 같다. The light emitting layer 130 may further include a dopant. The dopant may be a red, green or blue dopant, for example a phosphorescent dopant. The dopant is as described above.
유기층 (105)은 애노드 (1 10)와 발광층 (130) 사이 및 /또는 캐소드 (120)와 발광층 (130) 사이에 위치하는 보조층 (도시하지 않음)을 더 포함할 수 있다. The organic layer 105 may further include an auxiliary layer (not shown) positioned between the anode 1 10 and the light emitting layer 130 and / or between the cathode 120 and the light emitting layer 130.
보조층은 정공 주입층, 정공 수송층, 전자 차단층, 전자 주입층, 전자 수송층, 정공
차단층 또는 이들의 조합일 수 있다. 보조층은 전술한 유기 화합물 또는 조성물을 포함할 수 있다. The auxiliary layer is a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole Barrier layers or combinations thereof. The auxiliary layer may comprise the aforementioned organic compound or composition.
상술한 유기 발광 소자는 유기 발광 표시 장치에 적용될 수 있다. 【발명의 실시를 위한 형태】 The organic light emitting diode described above may be applied to an organic light emitting diode display. [Form for implementation of invention]
이하에서는 본 발명의 구체적인 실시예들을 제시한다. 다만, 하기에 기재된 실시예들은 본 발명을 구체적으로 예시하거나 설명하기 위한 것에 블과하며, 이로서 본 발명이 제한되어서는 아니된다. The following presents specific embodiments of the present invention. However, the embodiments described below are only for illustrating or explaining the present invention in detail, and the present invention is not limited thereto.
중간체의 합성 Synthesis of Intermediates
합성예 1: 중간체 1-1의 합성 Synthesis Example 1 Synthesis of Intermediate 1-1
[반웅식 1] [Banungsik 1]
질소 환경에서 zhengzhou chemical international Co., Zhengzhou chemical international Co., Ltd. in a nitrogen environment
Ltd(http://www.chemicalintl.com/)사의 . 3-bromophenanthrene-9, 10-dione(l 00 g, 348 mmol)을 ethanol 1 L에 녹인 후, 여기에 ethylenediamine(25.1 g, 418 mmol)을 넣고 8시간 가열하여 환류 시킨 후， acetic acid를 추가로 1.5 L 넣어 9시간 가열하여 환류 시켰다ᅳ 반웅 완료 후 반웅 액을 상온으로 넁각 시켰다. 생성된 고체를 여과하여 과량의 ethan이으로 씻어 중간체 1-1(78.5 g, 73 %)을 얻었다. Ltd (http://www.chemicalintl.com/) . Dissolve 3-bromophenanthrene-9 and 10-dione (l 00 g, 348 mmol) in 1 L of ethanol, add ethylenediamine (25.1 g, 418 mmol) to it for 8 hours, reflux it, and add acetic acid. 1.5 L was added and heated to reflux for 9 hours. After completion of reaction, the reaction solution was cooled to room temperature. The resulting solid was filtered and washed with excess ethanol to give intermediate 1-1 (78.5 g, 73%).
HRMS (70 eV, EI+): m/z calcd for C16H9BrN2: 307.9949, found: 308. HRMS (70 eV, EI < + >): m / z calcd for C16H9 BrN2: 307.9949, found: 308.
Elemental Analysis: C, 62 %; H, 3 % Elemental Analysis: C, 62%; H, 3%
합성예 2: 중간체 1-2의 합성 Synthesis Example 2 Synthesis of Intermediate 1-2
[반웅식 2] [Bungungsik 2]
1^&^5( ∞ 1 03 1^) &11& ^ (2.61 2.26 1 101)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(78.1 g, 565 mmol)을 넣고 80 °C에서 8시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-2(65.5 g, 85 %)를 얻었다. 1 ^ & ^ 5 (∞ 1 03 1 ^) & 11 & ^ was stirred into a (2 0.61 2.26 1 101). Potassium carbonate saturated in water (78.1 g, 565 mmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 8 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate 1-2 (65.5 g, 85%).
HRMS (70 eV, EI+): m/z calcd for C22H13C1N2: 340.0767, found: 340. HRMS (70 eV, EI < + >): m / z calcd for C22H13C1N2: 340.0767, found: 340.
Elemental Analysis: C, 78 %; H, 4 % Elemental Analysis: C, 78%; H, 4%
합성예 3: 중간체 1-3의 합성 Synthesis Example 3 Synthesis of Intermediate 1-3
[반웅식 3] [Banungsik 3]
1 - 2 1 - 3 질소 환경에서 중간체 1-2(60 g, 176 mmol)를 dimethylforamide(DMF) 0.6 L에 녹인 후, 여기에 bis(pinacolato)diboron(53.6 g, 211 mmol)와 (1 ,1 '- bis(diphenylphosphine)ferrocene)dichloropalladium(II)( 1.44 g, 1.76 mmol) 그리고 potassium acetate(51.8 g, 528 mmol)을 넣고 150 °C에서 20시간 동안 가열하여 환류시켰다. 반웅 완료 후 반웅액에 물을 넣고 흔합물을 필터한 후, 진공오본에서 건조하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-3(51.7 g, 68 %)을 얻었다. 1-2 1-3 Dissolve intermediate 1-2 (60 g, 176 mmol) in 0.6 L of dimethylforamide (DMF) in a nitrogen environment, and add bis (pinacolato) diboron (53.6 g, 211 mmol) and (1,1 '-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (1.44 g, 1.76 mmol) and potassium acetate (51.8 g, 528 mmol) were added and heated to reflux for 20 hours at 150 ° C. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate 1-3 (51.7 g, 68%).
HRMS (70 eV, EI+): m/z calcd for C28H25BN202: 432.2009, found: 432. HRMS (70 eV, EI < + >): m / z calcd for C28H25BN202: 432.2009, found: 432.
Elemental Analysis: C, 78 %; H, 6 % Elemental Analysis: C, 78%; H, 6%
합성예 4: 중간체 1-4의 합성
[반웅식 4] Synthesis Example 4 Synthesis of Intermediate 1-4 [Banungsik 4]
1 - 4 1-4
질소 환경에서 중간체 1-3(50 g, 1 16 mmol)을 tetrahydrofuran(THF) 0.45 L에 녹인 후, 여기에 l-bromo-3-iodobenzene(39.3 g, 139 mmol)와 In nitrogen, Intermediate 1-3 (50 g, 1 16 mmol) was dissolved in 0.45 L of tetrahydrofuran (THF), followed by l-bromo-3-iodobenzene (39.3 g, 139 mmol).
tetrakis(triphenylphosphine)palladium(1.34 g, 1.16 mmol)-§- 넣고 교반시켰다. 물에 포화된 potassuim carbonate(40.1 g, 290 mmol)을 넣고 80 °C에서 5시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-4(47.1 g, 88 %)를 얻었다. tetrakis (triphenylphosphine) palladium (1.34 g, 1.16 mmol) -§- was added and stirred. Potassium carbonate saturated in water (40.1 g, 290 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 5 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-4 (47.1 g, 88%).
HRMS (70 eV, EI+): m/z calcd for C28H17BrN2: 460.0575, found: 460. HRMS (70 eV, EI < + >): m / z calcd for C 28 H 17 BrN 2: 460.0575, found: 460.
Elemental Analysis: C, 73 %; H, 4 % Elemental Analysis: C, 73%; H, 4%
합성예 5: 중간체 1-5의 합성 Synthesis Example 5 Synthesis of Intermediate 1-5
[반웅식 5] [Bungungsik 5]
HRMS (70 eV, EI+): m/z calcd for C34H29BN202: 508.2322, found: 508.
Elemental Analysis: C, 80 %; H, 6 % HRMS (70 eV, EI < + >): m / z calcd for C 34 H 29 BN202: 508.2322, found: 508. Elemental Analysis: C, 80%; H, 6%
합성예 6: 중간체 1-6의 합성 Synthesis Example 6 Synthesis of Intermediate 1-6
[반웅식 6] [Bandungsik 6]
HRMS (70 eV, EI+): m/z calcd for C22H21BN202: 356.1696, found: 356. HRMS (70 eV, EI < + >): m / z calcd for C22H21BN202: 356.1696, found: 356.
Elemental Analysis: C, 74 %; H, 6 % Elemental Analysis: C, 74%; H, 6%
합성예 7: 중간체 1-7의 합성 Synthesis Example 7 Synthesis of Intermediate 1-7
[반응식 기 Reaction group
질소 환경에서 중간체 1-6(100 g, 281 mmol)을 tetrahydrofuran(THF) 1L에 녹인 후, 여기에 l-bromo-2-iock benzene(95.3 g, 337 mmol)와 In nitrogen, Intermediate 1-6 (100 g, 281 mmol) was dissolved in 1 L of tetrahydrofuran (THF), followed by l-bromo-2-iock benzene ( 95.3 g, 337 mmol).
tetrakis(triphenylphosphine)palladium(3.25 g, 2.81 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(97.1 g, 703 mmol)을 넣고 80 °C에서 8시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반응액에 물을 넣고 dichloromethane(DCM)로 추출한
다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 아렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-7(92.0 g, 85 %)을 얻었다. tetrakis (triphenylphosphine) palladium (3.25 g, 2.81 mmol) was added and stirred. Potassium carbonate (97.1 g, 703 mmol) saturated in water was added thereto, and the mixture was heated and refluxed at 80 ° C. for 8 hours. After reaction, water was added to the reaction solution and extracted with dichloromethane (DCM). Then water was removed with anhydrous MgS04, filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-7 (92.0 g, 85%).
HRMS (70 eV, EI+): m/z calcd for C22H13BrN2: 384.0262, found: 384. HRMS (70 eV, EI < + >): m / z calcd for C 22 H 13 BrN 2: 384.0262, found: 384.
Elemental Analysis: C, 69 %; H, 3 % Elemental Analysis: C, 69%; H, 3%
합성예 8: 중간체 1-8의 합성 Synthesis Example 8 Synthesis of Intermediate 1-8
[반웅식 8]
[Banungsik 8]
1 · ' 1 - 8 1 , '1-8
질소 환경에서 중간체 1-7(90 g, 234 mmol)을 tetrahydrofuran(THF) 0.7L에 녹인 후, 여기에 3-chlorophenylboronic acid(43.8 g, 280 mmol)≤f In nitrogen, Intermediate 1-7 (90 g, 234 mmol) was dissolved in 0.7 L of tetrahydrofuran (THF), followed by 3-chlorophenylboronic acid (43.8 g, 280 mmol)
tetrakis(triphenylphosphine)palladium(2.70 g, 2.34 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(80.9 g, 585 mmol)을 넣고 80 °C에서 12시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-8(81.0 g, 83 %)을 얻었다. tetrakis (triphenylphosphine) palladium (2.70 g, 2.34 mmol) was added and stirred. Potassium carbonate saturated in water (80.9 g, 585 mmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-8 (81.0 g, 83%).
HRMS (70 eV, EI+): m/z calcd for C28H17C1N2: 416.1080, found: 416. HRMS (70 eV, EI < + >): m / z calcd for C 28 H 17 C 1 N 2: 416.1080, found: 416.
Elemental Analysis: C, 81 %; H, 4 % Elemental Analysis: C, 81%; H, 4%
합성예 9: 중간체 1-9의 합성 Synthesis Example 9 Synthesis of Intermediate 1-9
[반응식 9] Scheme 9
1 - 8 1 - 9 1-8 1-9
질소 환경에서 중간체 1-8(75 g, 180 mmol)을 dimethylfommide(DMF) 1L에 녹인 후, 여기에 1^(1 0 0)^1)01ᅳ0^54.8 216 11 01)와 (1 ,1 '-
bis(diphenylphosphine)ferrocene)dichloropalladium(II)(1.47 g, 1.80 mmol) 그리고 potassium acetate(53.0 g, 540 mmol)을 넣고 150°C에서 23시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 흔합물을 필터한 후, 진공오븐에서 건조하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-9(55.8 g, 61 %)을 얻었다. In nitrogen, Intermediate 1-8 (75 g, 180 mmol) was dissolved in 1 L of dimethylfommide (DMF), followed by 1 ^ (1 0 0) ^ 1) 01 ᅳ 0 ^ 54.8 216 11 01) and (1, 1 '- Bis (diphenylphosphine) ferrocene) dichloropalladium (II) (1.47 g, 1.80 mmol) and potassium acetate (53.0 g, 540 mmol) were added and heated to reflux for 23 hours at 150 ° C. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-9 (55.8 g, 61%).
HRMS (70 eV, EI+): m/z calcd for C34H29BN202: 508.2322, found: 508. HRMS (70 eV, EI < + >): m / z calcd for C 34 H 29 BN202: 508.2322, found: 508.
Elemental Analysis: C, 80 %; H, 6 % Elemental Analysis: C, 80%; H, 6%
합성예 10: 중간체 1-10의 합성 Synthesis Example 10 Synthesis of Intermediate 1-10
[반웅식 10] [Banungsik 10]
질소 환경에서 중간체 1-3(50 g, 116 mmol)을 tetrahydrofuran(THF) 0.45 L에 녹인 후, 여기데 l-bromo-2-iodobenzene(39.3 g, 139 mmol)와 In nitrogen, Intermediate 1-3 (50 g, 116 mmol) was dissolved in 0.45 L of tetrahydrofuran (THF), followed by l-bromo-2-iodobenzene (39.3 g, 139 mmol).
tetrakis(triphenylphosphine)palladium(1.34 g, 1.16 mmol)-i: 넣고 교반시켰다. 물에 포화된 1« 35^^ 0&1 0^( 40.1 290 1111：101)을 넣고 80°C에서 8시간 동안 가열하여 환류 시켰다. 반옹 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 I-10(48.2 g, 90 %)을 얻었다. tetrakis (triphenylphosphine) palladium (1.34 g, 1.16 mmol) -i: added and stirred. 1 «35 ^^ 0 & 1 0 ^ (40.1 290 1111 ： 101) saturated in water was added and refluxed at 80 ° C. for 8 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-10 ( 4 8.2 g, 90%).
HRMS (70 eV, EI+): m/z calcd for C28H17BrN2: 460.0575, found: 460. HRMS (70 eV, EI < + >): m / z calcd for C 28 H 17 BrN 2: 460.0575, found: 460.
Elemental Analysis: C, 73 %; H, 4 % Elemental Analysis: C, 73%; H, 4%
합성예 11: 중간체 1-11의 합성
[반웅식 Synthesis Example 11 Synthesis of Intermediate 1-11 [Bungungsik
질소 환경에서 중간체 1-10(45 g, 9그 5 mmol)를 dimethylforamide(DMF) 0.4 L에 녹인 후, 여기에 bis(pinacolato)diboron(29.7 g, 117mmol)와 (Ι,Ι'- bis(diphenylphosphine)ferrocene)dichloropalladium(II)(0.80 g, 0.98 mmol) 그리고 potassium acetate(28.7 g, 293 mmol) 넣고 150 °C에서 18시간 동안 가열하여 환류 시켰다. 반응 완료 후 반웅액에 물을 넣고 흔합물을 필터한 후, 진공오븐에서 건조하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-11(32.2 g, 65 %)를 얻었다. In a nitrogen environment, intermediate 1-10 (45 g, 9 mmol 5 mmol) was dissolved in 0.4 L of dimethylforamide (DMF), followed by bis (pinacolato) diboron (29.7 g, 117 mmol) and (Ι, Ι'- bis (diphenylphosphine). ) ferrocene) dichloropalladium (II) (0.80 g, 0.98 mmol) and potassium acetate (28.7 g, 293 mmol) were added and refluxed at 150 ° C for 18 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-11 (32.2 g, 65%).
HRMS (70 eV, EI+): m/z calcd for C34H29BN202: 508.2322, found: 508. HRMS (70 eV, EI < + >): m / z calcd for C 34 H 29 BN202: 508.2322, found: 508.
Elemental Analysis: C, 80 %; H, 6 % Elemental Analysis: C, 80%; H, 6%
합성예 12: 중간체 1-12의 합성 Synthesis Example 12 Synthesis of Intermediate 1-12
[반응식 12] Scheme 12
1 -5 1 -12 1 -5 1 -12
질소 환경에서 중간체 1-5(40 g, 78.7 mmol)를 tetrahydrofuran(THF) 0.3 L에 녹인 후, 여기에 1-1>1：01110-3-10(101 ^6^(26.7 94.41111101)와 In nitrogen, Intermediate 1-5 (40 g, 78.7 mmol) was dissolved in 0.3 L of tetrahydrofuran (THF), followed by 1-1> 1: 01110-3-10 (101 ^ 6 ^ (26.7 94.41111101)
tetrakis(tΓiphenylphosphine)palladium(0.91 g, 0.79mrrlol)을 넣고 교반시켰다. 물에 포화된 1^&5^^ 0&1¾00 ^27.2 197111«01)을 넣고 80 °C에서 8시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-12(37.6 g, 89%)를 얻었다.
HRMS (70 eV, EI+): m/z calcd for C34H21BrN2: 536.0888, found: 536. tetrakis (tΓiphenylphosphine) palladium (0.91 g, 0.79mrrlol) was added and stirred. 1 ^ & 5 ^^ 0 & 1¾00 ^ 27.2 197111 «01) saturated in water was added and refluxed at 80 ° C. for 8 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-12 (37.6 g, 89%). HRMS (70 eV, EI < + >): m / z calcd for C 34 H 21 BrN 2: 536.0888, found: 536.
Elemental Analysis: C, 76 %; H, 4 % Elemental Analysis: C, 76%; H, 4%
합성예 13: 중간체 1-13의 합성 Synthesis Example 13 Synthesis of Intermediate 1-13
[반웅식 13] [Banungsik 13]
질소 환경에서 중간체 1-12(30 g, 55.8 mmol)를 dimethylforamide(DMF) 0.2 L에 녹인 후， 여기에 bis(pinacolato)diboron(17.0 g, 67.0 mmol)와 (1,1 '- bis(diphenylphosphine)ferrocene)dichloropalladium(II)(0.46 g, 0.56 mmol) 그리고 potassium acetate(l 6.4 g, 167 mmol)을 넣고 150 °C에서 6시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 흔합물을 필터한 후, 진공오븐에서 건조하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-13(26.7 g, 82 %)을 얻었다. In nitrogen, Intermediate 1-12 (30 g, 55.8 mmol) was dissolved in 0.2 L of dimethylforamide (DMF), followed by bis (pinacolato) diboron (17.0 g, 67.0 mmol) and (1,1 '-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (0.46 g, 0.56 mmol) and potassium acetate (l 6.4 g, 167 mmol) were added and heated to reflux for 6 hours at 150 ° C. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-13 (26.7 g, 82%).
HRMS (70 eV, EI+): m/z calcd for C40H33BN2O2: 584.2635, found: 584. HRMS (70 eV, EI < + >): m / z calcd for C 40 H 33 BN 2 O 2: 584.2635, found: 584.
Elemental Analysis: C, 82 %; H, 6 % Elemental Analysis: C, 82%; H, 6%
합성예 14: 중간체 1-14의 합성 Synthesis Example 14 Synthesis of Intermediate 1-14
[반웅식 14]
[Banungsik 14]
질소 환경에서 zhengzhou chemical international Co., Zhengzhou chemical international Co., Ltd. in a nitrogen environment
Ltd(http://www.chemicalintl.com/)人!"의 3,6-dibromophenanthrene-9, 10-dione( 100 g, 273 mmol)을 ethanol l L에 녹인 후, 여기에 ethylenediamine(25.1 g, 418 mmol)을 넣고 8시간 가열하여 환류 시킨 후， acetic acid를 추가로 1.5 L 넣어 9시간 가열하여 환류 시켰다. 반웅 완료 후 반응 액을 상온으로 넁각 시켰다. 생성된 고체를
여과하여 과량의 ethan이으로 씻어 중간체 1-14(78.5 g, 73 %)를 얻었다. 3,6-dibromophenanthrene-9 and 10-dione (100 g, 273 mmol) of the company (http://www.chemicalintl.com/) 人! "Are dissolved in ethanol L, followed by ethylenediamine (25.1 g, 418 mmol) was added and heated to reflux for 8 hours, and then 1.5 liters of acetic acid was added and heated to reflux for 9 hours.After completion of reaction, the reaction solution was cooled down to room temperature. Filtration was washed with excess ethanol to give intermediate 1-14 (78.5 g, 73%).
HRMS (70 eV, EI+): m/z calcd for C16H8Br2N2: 385.9054, found: 385. HRMS (70 eV, EI < + >): m / z calcd for C 16 H 8 Br 2 N 2: 385.9054, found: 385.
Elemental Analysis: C, 50 %; H, 2 % Elemental Analysis: C, 50%; H, 2%
합성예 15: 중간체 1-15의 합성 Synthesis Example 15 Synthesis of Intermediate 1-15
[반웅식 15]
[Banungsik 15]
질소 환경에서 sigma aldrich(http://www.sigmaaldrich.com/)사의 2-bromo-5- iodopyridine(100 g, 352 mmol)를 tetrahydrofuran(THF) ().8 L에 녹인 후, 여기에 pyridin- 4-ylboronic acid(52.0 g, 423 mmol)와 tetrakis(triphenylphosphine)palladium(4.07 g, 3.52 mmol)을 넣고 교반시켰다. 물에 포화된 1^&3^^ 0^1?0 16(122 880 010101)을 넣고 80 °C에서 12시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 1-15(29.8 g, 36 %)를 얻었다. In a nitrogen environment, 2-bromo-5-iodopyridine (100 g, 3 52 mmol) from sigma aldrich (http://www.sigmaaldrich.com/) was dissolved in tetrahydrofuran (THF) (8.8 L), followed by pyridin 4-ylboronic acid (52.0 g, 423 mmol) and tetrakis (triphenylphosphine) palladium (4.07 g, 3.52 mmol) were added and stirred. 1 ^ & 3 ^^ 0 ^ 1? 0 16 (122 880 010101) saturated in water was added thereto, and the mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-15 (29.8 g, 36%).
HRMS (70 eV, EI+): m/z calcd for C10H7BrN2: 233.9793, found: 234. HRMS (70 eV, EI < + >): m / z calcd for C10H7BrN2: 233.9793, found: 234.
Elemental Analysis: C, 51 %; H, 3 % 최종 화합물의 합성 Elemental Analysis: C, 51%; H, synthesis of 3% final compound
합성예 16: 화합물 1와합성 Synthesis Example 16 Synthesis with Compound 1
[반응식 16] Scheme 16
질소 환경에서 중간체 1-3(10 g, 23.1 mmol)을 tetrahydrofuran(THF) 0.1 L에 녹인 후, 여기에 Nanjing Kindchem Co., Ltd.(http://www.kindchem.net/)사에서 구입한 4-chloro-2,6-diphenylpyridine(6.15 g, 23.1 mmol)와 In a nitrogen environment, Intermediate 1-3 (10 g, 23.1 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), which was purchased from Nanjing Kindchem Co., Ltd. (http://www.kindchem.net/). 4-chloro-2,6-diphenylpyridine (6.15 g, 23.1 mmol)
tetrakis(triphenylphosphine)palladium(0.27 g, 0.23 mmol)을 넣고 교반시켰다. 물에
포화된 potassuim carbonate(7.98 g, 57.8 mmol)을 넣고 80 °C에서 10시간 동안 가열하여 환류 시켰다ᅳ 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 1(1 1.1 g, 90 %)을 얻었다. tetrakis (triphenylphosphine) palladium (0.27 g, 0.23 mmol) was added and stirred. On the water Saturated potassuim carbonate (7.98 g, 57.8 mmol) was added and heated to reflux at 80 ° C for 10 hours. And concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1 (1 1.1 g, 90%).
HRMS (70 eV, EI+): m/z calcd for C39H25N3: 535.2048, found: 535. HRMS (70 eV, EI < + >): m / z calcd for C 39 H 25 N 3: 535.2048, found: 535.
Elemental Analysis: C, 87 %; H, 5 % Elemental Analysis: C, 87%; H, 5%
합성예 17: 화합물 2의 합성 Synthesis Example 17 Synthesis of Compound 2
[반웅식 17] [Banungsik 17]
질소 환경에서 중간체 1-3(10 g, 23.1 mmol)을 tetrahydrofuran(THF) 0.1 L에 녹인 '후, 여기'에 Tokyo Chemical Industry(http://www.tcichemicals.com/)사에서 구입한 2-chloro-4,6-diphenylpyrimidine(6.16 g, 23.1 mmol)와 Intermediate 1-3 (10 g, 23.1 mmol) in a nitrogen atmosphere tetrahydrofuran (THF), and then, where 'was dissolved in 0.1 L of 2-purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/) Inc. chloro-4,6-diphenylpyrimidine (6.16 g, 23.1 mmol)
tetrakis(triphenylphosphine)palladium(0.27 g, 0.23 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(7.98 g, 5그 8 mmol)을 넣고 80 °C에서 10시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloroniethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 2(10.5 g, 85 %)를 얻었다. tetrakis (triphenylphosphine) palladium (0.27 g, 0.23 mmol) was added and stirred. Potassium carbonate saturated in water (7.98 g, 5 mmol, 8 mmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 10 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloroniethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 2 (10.5 g, 85%).
HRMS (70 eV, EI+): m/z calcd for C38H24N4: 536.2001, found: 536. HRMS (70 eV, EI < + >): m / z calcd for C38H24N4: 536.2001, found: 536.
Elemental Analysis: C, 85 %; H, 5 % Elemental Analysis: C, 85%; H, 5%
합성예 18: 화합물 3의 합성
[반응식 18] Synthesis Example 18 Synthesis of Compound 3 Scheme 18
질소 환경에서 중간체 1-3(10 g, 23.1 mmol)을 tetrahydrofuran(THF) 0.1 L에 녹인 후, '여기에 Tokyo Chemical Industry(http://www.tcichemicals.com/)사에서 구입한 2-chloro-4,6-diphenyl- 1 ,3,5-triazine(6.18 g, 23.1 mmol)와 In a nitrogen environment, Intermediate 1-3 (10 g, 23.1 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), followed by ' 2-chloro purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/). -4,6-diphenyl-l, 3,5-triazine (6.18 g, 23.1 mmol)
tetrakis(triphenylphosphme)palladium(0.27 g, 0.23 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate (그 98 g, 57.8 mmol)을 넣고 80 °C에서 10시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 3(1 1.5 g, 93 %)을 얻었다 tetrakis (triphenylphosphme) palladium (0.27 g, 0.23 mmol) was added and stirred. Potassium carbonate saturated in water (98 g, 57.8 mmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 10 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 3 (1 1.5 g, 93%).
HRMS (70 eV, EI+): m/z calcd for C37H23N5: 537.1953, found: 537. HRMS (70 eV, EI < + >): m / z calcd for C 37 H 23 N 5: 537.1953, found: 537.
Elemental Analysis: C, 83 %; H, 4 % Elemental Analysis: C, 83%; H, 4%
합성예 19: 화합물 12의 합성 Synthesis Example 19 Synthesis of Compound 12
[ [
질소 환경에서 중간체 1-5(10 g, 19.7 mmol)을 tetrahydrofuran(THF) 0.1 L에 녹인 후， 여기에 Tokyo Chemical Industry(http://www.tcichemicals.com/)사에서 구입한 2-chloro-4,6-diphenyl-l ,3,5-triazine(5.27 g, 19.7 mmol)와 In nitrogen, Intermediate 1-5 (10 g, 19.7 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), and 2-chloro- purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/). 4,6-diphenyl-l, 3,5-triazine (5.27 g, 19.7 mmol)
tetrakis(triphenylphosphine)palladium(0.23 g, 0.20 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(6.81 g, 49.3 mmol)을 넣고 80 °C에서 9시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게
얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 12(9.67 g: 80 %)를 얻었다. tetrakis (triphenylphosphine) palladium (0.23 g, 0.20 mmol) was added and stirred. Potassium carbonate saturated in water (6.81 g, 49.3 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 9 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. like this The obtained residue was separated and purified through flash column chromatography to obtain Compound 12 (9.67 g : 80%).
HRMS (70 eV, EI+): m/z calcd for C43H27N5: 613.2266, found: 613. HRMS (70 eV, EI < + >): m / z calcd for C 43 H 27 N 5: 613.2266, found: 613.
Elemental Analysis: C, 84 %; H, 4 % Elemental Analysis: C, 84%; H, 4%
합성예 20: 화합물 21의 합성 Synthesis Example 20 Synthesis of Compound 21
[반웅식 20] [Banungsik 20]
질소 환경에서 중간체 1-9(10 g, 19.7 mmol)를 tetrahydrofuran(THF) 0.1 L에 녹인 후, 여기에 Tokyo Chemical Industry(http://www.tcichemicals.com/)사에서 구입한 2-chloro-4,6-diphenyl-l ,3,5-triazine(5.27 g, 19.7 mmol)와 In nitrogen environment, intermediate 1-9 (10 g, 19.7 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), followed by 2-chloro- purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/). 4,6-diphenyl-l, 3,5-triazine (5.27 g, 19.7 mmol)
tetrakis(triphenylphosphine)palladium(0.23 g, 0·20 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(6.81 g, 49.3 mmol)을 넣고 80 °C에서 12시간 동안 가열하연 환류 시켰다. 반웅 완료 후 반응액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 21(9.31 g, 77 %)을 얻었다. tetrakis (triphenylphosphine) palladium (0. 2 3 g, 0. 2 0 mmol) was added and stirred. Potassium carbonate saturated in water (6.81 g, 49.3 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After completion of reaction, water was added to the reaction solution, followed by extraction with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Compound 21 (9.31 g, 77%).
HRMS (70 eV, EI+): m/z calcd for C43H27N5: 613.2266, found: 613. HRMS (70 eV, EI < + >): m / z calcd for C 43 H 27 N 5: 613.2266, found: 613.
Elemental Analysis: C, 84 %; H, 4 % Elemental Analysis: C, 84%; H, 4%
합성예 21: 화합물 30의 합성 Synthesis Example 21 Synthesis of Compound 30
[ [
질소 환경에서 중간체 1-1 1(10 g, 19.7 mmol)을 tetrahydrofuran(THF) 0.1 L에
녹인 후, 여기에 Tokyo Chemical Industry(http://www.tcichemicals.com/)사에서 구입한 2-chloro-4,6-diphenyl- l ,3,5-triazine(5.27 g, 19.7 mmol)와 Intermediate 1-1 1 (10 g, 19.7 mmol) was added to 0.1 L of tetrahydrofuran (THF) in a nitrogen environment. After dissolving, 2-chloro-4,6-diphenyl-l, 3,5-triazine (5.27 g, 19.7 mmol) purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/)
tetrakis(triphenylphosphine)palladium(0.23 g, 0.20 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(6.81 g, 49.3 mmol)을 넣고 80 °C에서 10시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 30(6.29 g, 52 %)을 얻었다. tetrakis (triphenylphosphine) palladium (0.23 g, 0.20 mmol) was added and stirred. Potassium carbonate saturated in water (6.81 g, 49.3 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C for 10 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 30 (6.29 g, 52%).
HRMS (70 eV, EI+): m/z calcd for C43H27N5 : 613.2266, found: 613. HRMS (70 eV, EI < + >): m / z calcd for C 43 H 27 N 5: 613.2266, found: 613.
Elemental Analysis: C, 84 %; H, 4 % Elemental Analysis: C, 84%; H, 4%
합성예 22: 화합물 39의 합성 Synthesis Example 22 Synthesis of Compound 39
[반웅식 22] [Bungungsik 22]
tetrakis(triphenylphosphine)palladium(0.20 g, 0.17 mnlol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(5.92 g, 42.8 mmol)을 넣고 80 °C에서 1 5시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 39(10.6 g, 90 %)를 얻었다. tetrakis (triphenylphosphine) palladium (0.20 g, 0.17 mnlol) was added and stirred. Potassium carbonate saturated in water (5.92 g, 42.8 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 1 5 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 39 (10.6 g, 90%).
HRMS (70 eV, EI+): m/z calcd for C49H31N5: 689.2579, found: 689. HRMS (70 eV, EI < + >): m / z calcd for C 49 H 31 N 5: 689.2579, found: 689.
Elemental Analysis: C, 85 %; H, 5 % Elemental Analysis: C, 85%; H, 5%
합성예 23: 화합물 Host 1의 합성
Synthesis Example 23 Synthesis of Compound Host 1
공개된 특허 KR2014-0135524A의 합성예 17과 동일한 방법으로 합성하였다. HRMS (70 eV, EI+): m/z calcd for C45H29N3 : 61 1.2361, found: 61 1. It synthesize | combined by the method similar to the synthesis example 17 of published patent KR2014-0135524A. HRMS (70 eV, EI +): m / z calcd for C 45 H 29 N 3: 61 1.2361, found: 61 1.
Elemental Analysis: C, 88 %; H, 5 % Elemental Analysis: C, 88%; H, 5%
합성예 24: 화합물 Host2의 합성 Synthesis Example 24 Synthesis of Compound Host2
[반웅식 23] [Banungsik 23]
질소 환경에서 중간체 1-14(10 g, 25.8 mmol)를 tetrahydrofuran(THF) 0.1 L에 녹인 후, 여기에 중간체 1-15(12.1 g, 51.5 mmol)와 In nitrogen, Intermediate 1-14 (10 g, 25.8 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), followed by Intermediate 1-15 (12.1 g, 51.5 mmol).
tetrakis(triphenylphosphine)palladium(0.60 g, 0.52 mmol)을 넣고 교반시켰다. 물에 포화된 potassuim carbonate(17.8 g, 129 Inmol)을 넣고 80 °C에서 18시간 동안 가열하여 환류 시켰다. 반웅 완료 후 반웅액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 화합물 Host 2(10.4 g, 75 %)를 얻었다. tetrakis (triphenylphosphine) palladium (0.60 g, 0.52 mmol) was added and stirred. Potassium carbonate saturated in water (17.8 g, 129 Inmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 18 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound Host 2 (10.4 g, 75%).
HRMS (70 eV, EI+): m/z calcd for C36H22N6: 538.1906, found: 538. HRMS (70 eV, EI < + >): m / z calcd for C36H22N6: 538.1906, found: 538.
Elemental Analysis: C, 80 %; H, 4 % 유기 발광 소자의 제작 I Elemental Analysis: C, 80%; H, Fabrication of 4% Organic Light-Emitting Device I
실시예 1 Example 1
합성예 16에서 얻은 화합물 1을 호스트로 사용하고, Ir(PPy)3를 도편트로 사용하여 유기발광소자를 제작하였다. An organic light emitting device was manufactured using Compound 1 obtained in Synthesis Example 16 as a host and Ir (PPy) 3 as a dopant.
양극으로는 ΠΌ를 1000 A의 두께로 사용하였고, 음극으로는
알루미늄 (Al)을 1000 A의 두께로 사용하였다. 구체적으로, 유기발광소자의 제조방법을 설명하면， 양극은 15 Ω/αη2의 면저항값을 가진 ΠΌ 유리 기판을 50mm X 50 mm X 0.7 mm의 크기로 잘라서 아세톤과 이소프로필알코올과 순수물 속에서 각 15 분 동안 초음파세정한 후， 30 분 동안 UV 오존 세정하여 사용하였다. ΠΌ was used as a positive electrode with a thickness of 1000 A. Aluminum (Al) was used at a thickness of 1000 A. Specifically, the method of manufacturing the organic light emitting device, the anode is cut into a glass substrate having a sheet resistance value of 15 Ω / αη 2 to a size of 50mm x 50 mm x 0.7 mm in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was used for 30 minutes.
상기 기판 상부에 진공도 650> 10-7Pa, 증착속도 0.1 내지 0.3 nm/s의 조건으로 N4,N4'-di(naphthalen- l -yl)-N4,N4'-diphenylbiphenyl-4,4'-diami^ (NPB) (80 nm)를 증착하여 800 A의 정공수송층을 형성하였다. 이어서, 동일한 진공 증착조건에서 합성예 16에서 얻은 화합물 1을 이용하여 막 두께 300 A의 발광층올 형성하였고, 이 때, 인광 도펀트인 Ir(PPy)3을 동시에 증착하였다. 이 때, 인광 도편트의 증착속도를 조절하여, 발광층의 전체량을 100 중량0 /0로 하였을 때, 인광 도편트의 배합량이 7 중량0 /。가 되도록 증착하였다. N4, N4'-di (naphthalen-l-yl) -N4, N4'-diphenylbiphenyl-4,4'-diami ^ on the substrate at a vacuum degree of 650> 10-7Pa and a deposition rate of 0.1 to 0.3 nm / s. (NPB) (80 nm) was deposited to form a hole transport layer of 800 A. Subsequently, a light emitting layer having a thickness of 300 A was formed using Compound 1 obtained in Synthesis Example 16 under the same vacuum deposition conditions. At this time, Ir (PPy) 3, which is a phosphorescent dopant, was simultaneously deposited. At this time, by adjusting the deposition rate of the phosphorescent dopyeon agent, the amount of the phosphorescent dopyeon agent was deposited such that the weight 7 0 /. When the total amount of the light-emitting layer to 100 parts by weight 0/0.
상기 발광층 상부에 동일한 진공 증착조건을 이용하여 Bis(2-methyl-8- qumolinolate)-4-(phenylphenolato)aluminium (BAlq)를 증착하여 막 두께 50 A의 정공저지층올 형성하였다ᅳ 이어서, 동일한 진공 증착조건에서 Alq3를 증착하여, 막 두께 200 A의 전자수송층을 형성하였다. 상기 전자수송층 상부에 음극으로서 Bis (2-methyl-8- qumolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 A. Subsequently, the same vacuum deposition was performed. Alq3 was deposited under the conditions to form an electron transport layer having a thickness of 200 A. As a cathode on the electron transport layer
LiF와 A1을 순차적으로 증착하여 유기광전소자를 제작하였다. LiF and A1 were sequentially deposited to manufacture an organic photoelectric device.
상기 유기광전소자의 구조는 nO/ NPB (80 nm)/ EML (화합물 1 (93 중량0 /。) + Ir(PPy)3(7 중량0 /。), 30 nm)/ Balq (5 nm)/ Alq3 (20 nm)/ LiF (1 nm) / Al (100 nm) 의 구조로 제작하였다. The structure of the organic photoelectric device is nO / NPB (80 nm) / EML (Compound 1 (93 weight 0 /.) + Ir (PPy) 3 (7 weight 0 /.), 30 nm) / Balq (5 nm) / It was produced in the structure of Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).
실시예 2 내지 7 Examples 2-7
합성예 16에서 얻은 화합물 1 대신 합성예 17에서 얻은 화합물 2, 합성예 18에서 얻은 화합물 3， 합성예 19에서 얻은 화합물 12, 합성예 20에서 얻은 화합물 21 , 합성예 21에서 얻은 화합물 30 및 합성예 22에서 얻은 화합물 39를 각각 사용한 것을 제외하고 실시예 1과 동일한 방법으로 실시예 2 내지 7의 유기발광소자를 제조하였다. Instead of compound 1 obtained in synthesis example 16, compound 2 obtained in synthesis example 17, compound 3 obtained in synthesis example 18, compound 12 obtained in synthesis example 19, compound 21 obtained in synthesis example 20, compound 30 obtained in synthesis example 21, and synthesis example The organic light emitting diodes of Examples 2 to 7 were prepared by the same method as Example 1, except that Compound 39 obtained in 22 was used.
비교예 1 내지 3 Comparative Examples 1 to 3
합성예 16에서 얻은 화합물 1 대신 CBP, 합성예 23에서 얻은 화합물 Host l 및 합성예 24에서 얻은 화합물 Host 2를 각각 사용한 것을 제외하고 실시예 1과 동일한 방법으로 비교예 1 내지 3의 유기발광소자를 제조하였다.
상기 유기발광소자 제작에 사용된 NPB, BAlq, CBP 및 Ir(PPy)3의 구조는 하기와 같다. The organic light emitting diodes of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that CBP, Compound Host 1 obtained in Synthesis Example 23, and Compound Host 2 obtained in Synthesis Example 24 were used instead of Compound 1 obtained in Synthesis Example 16. Prepared. The structure of NPB, BAlq, CBP and Ir (PPy) 3 used in the organic light emitting device is as follows.
(NPB] (NPB]
[CBP] tlr(PPy) [CBP] tlr (PPy)
실시예 1 내지 7과 비교예 1 내지 3에 따른 유기발광소자의 전압에 따른 전류밀도 변화, 휘도 변화 및 발광효율을 측정하였다ᅳ Current density change, luminance change, and luminous efficiency of the organic light emitting diode according to Examples 1 to 7 and Comparative Examples 1 to 3 were measured.
구체적인 측정방법은 하기와 같고, 그 결과는 표 1과 같다. Specific measurement methods are as follows, and the results are shown in Table 1.
(1) 전압변화에 따른 전류밀도의 변화 측정 (1) Measurement of change of current density according to voltage change
제조된 유기발광소자에 대해, 전압을 0V 부터 10V까지 상승시키면서 전류- 전압계 (Keithley 2400)를 이용하여 단위소자에 흐르는 전류값을 측정하고， 측정된 전류값을 면적으로 나누어 결과를 얻었다. For the organic light emitting device manufactured, the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
(2) 전압변화에 따른 휘도변화 측정 (2) Measurement of luminance change according to voltage change
제조된 유기발광소자에 대해, 전압을 0V 부터 10V까지 상승시키면서 휘도계 (Minolta Cs-IOOOA)를 이용하여 그 때의 휘도를 측정하여 결과를 얻었다. For the manufactured organic light emitting device, the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
(3) 발광효율 측정 (3) Measurement of luminous efficiency
상기 (1) 및 (2)로부터 측정된 휘도와 전류밀도 및 전압을 이용하여 동일 전류밀도 (10 mA/cm2)의 전류 효율 (cd/A) 을 계산하였다. The current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
[표 1] TABLE 1
o. 화합물 구동전압 (V) 색 (EL color) 효율 (cd/A)
실시예 1 1 3.5 Green 88.9 o. Compound drive voltage (V) Color (EL color) Efficiency (cd / A) Example 1 1 3.5 Green 88.9
실시예 2 2 3.3 Green 90.4 Example 2 2 3.3 Green 90.4
실시예 3 3 3.2 Green 98.8 Example 3 3 3.2 Green 98.8
실시예 4 12 3.8 Green 85.2 Example 4 12 3.8 Green 85.2
실시예 5 21 3.6 Green 83.5 Example 5 21 3.6 Green 83.5
실시예 6 30 3.6 Green 88.0 Example 6 30 3.6 Green 88.0
실시예 7 39 4.0 Green 85.0 Example 7 39 4.0 Green 85.0
비교예 1 CBP 4.8 Green 31.4 Comparative Example 1 CBP 4.8 Green 31.4
비교예 2 HOST1 4.2 Green 74.3 Comparative Example 2 HOST1 4.2 Green 74.3
비교예 3 HOST2 4.3 Green 18.5 표 1을 참고하면, 실시예 1 내자 7에 따른 유기발광소자는 비교예 1 내지 3에 따른 유기발광소자와 비교하여 낮은 구동 전압 및 높은 발광 효율을 나타내는 것을 확인할 수 있다 · —— Comparative Example 3 HOST2 4.3 Green 18.5 Referring to Table 1, it can be seen that the organic light emitting diode according to Example 1 to 7 exhibits low driving voltage and high luminous efficiency compared to the organic light emitting diode according to Comparative Examples 1 to 3. · ——
합성예 18에서 얻은 화합물 3, 합성예 19에서 얻은 화합물 12 및 합성예 24에서 얻은 Host 2의 증착공정온도, 유리전이온도 (Tg) 및 고온순도를 각각 측정하였다. Deposition process temperature, glass transition temperature (Tg) and high temperature purity of Compound 3 obtained in Synthesis Example 18, Compound 12 obtained in Synthesis Example 19, and Host 2 obtained in Synthesis Example 24 were measured, respectively.
구체적인 측정방법은 하기와 같고， 그 결과는 표 2와 같다. Specific measurement methods are as follows, and the results are shown in Table 2.
(1) 증착공정 온도 (1) deposition process temperature
실시예 1에 따른 유기발광소자의 제작 공정 중 발광층의 HOST를 증착할 때 온도를 측정한 것으로 1초 (sec)당 1 A의 두께가 적층될 수 있는 온도를 의미한다 (A/sec) The temperature was measured when the HOST of the light emitting layer was deposited during the manufacturing process of the organic light emitting device according to Example 1, which means a temperature at which a thickness of 1 A may be stacked per second (A / sec).
(2) 유리전이온도 (Tg) (2) Glass transition temperature (Tg)
Metier teledo 사의 DSC1 장비를 이용하여 sample과 reference의 온도를 변화시키면서 energy 입력차를 온도의 함수로서 측정하였다. The energy input difference was measured as a function of temperature while changing the temperature of the sample and reference using a DSC1 instrument from Metier Teledo.
(3) 상온순도 (3) Room temperature purity
Waters사의 HPLC (모델명: Alliance e2695 - 4gradient pump) 및 waters사의 PDA (모델명: 2994)를 이용하여 측정하였다. 컬럼관은 Symmetry C18 (3.9 x 150 mm:
5 )을 이용하였다. Measurement was performed using Waters HPLC (Model: Alliance e2695-4gradient pump) and Waters PDA (Model: 2994). Column tube is Symmetry C18 (3.9 x 150 mm : 5) was used.
(4) 고온순도 (4) high temperature purity
화합물의 샘플올 l g 채취하여 유리용기에 질소로 충진 후 밀폐하였다. 상기 유리용기를 200 시간 200 °C 오븐에 보관 후 상기 상온순도를 측정하는 방법과 동일한 방법으로 순도를 측정하였다. Samples of the compounds were collected lg and filled with nitrogen in a glass container and sealed. After the glass container was stored in an oven at 200 ° C. for 200 hours, the purity was measured in the same manner as the method for measuring the room temperature purity.
[표 2] TABLE 2
따라서, 합성예 24에서 얻은 HOST 2를 유기발광소자에 적용한 비교예 3의 경우， 낮은 유리전이온도로 인해 소자를 제작하는 봉지공정 (약 60~90 °C에서 이루어짐)에서 박막에 문제가 소자결과에 악 영향을 준 것으로 예상되며, 유리발광소자의 제작 공정에서 열에 의해 깨져 소자효율에 영향을 미쳤을 것으로 예상된다. Therefore, in the case of Comparative Example 3 in which HOST 2 obtained in Synthesis Example 24 was applied to an organic light emitting device, a problem with the thin film was caused in the encapsulation process (which is performed at about 60 to 90 ° C) due to the low glass transition temperature. It is expected to adversely affect the efficiency of the glass light emitting device, which is likely to be broken by heat and affect device efficiency.
이에 반해, 합성예 18에서 얻은 화합물 3 및 합성예 19에서 얻은 화합물 12는 합성예 24에서 얻은 HOST 2와 비교하여 높은 분자량을 가짐에도 불구하고 낮은 유리전이은도를 가지면서 적절한 증착온도로 조절되어 고온에서도 높은 순도를 유지할 수 있음을 확인할 수 있다. 유기 발광 소자의 제작 II On the contrary, Compound 3 obtained in Synthesis Example 18 and Compound 12 obtained in Synthesis Example 19, although having a higher molecular weight than HOST 2 obtained in Synthesis Example 24, have a low glass transition degree and are controlled at an appropriate deposition temperature at a high temperature. It can be seen that even at high purity. Fabrication of Organic Light-Emitting Device II
실시예 8 Example 8
ΠΌ (Indium tin oxide)가 1500A의 두께로 박막 코팅된 유리 기판을 증류수
초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 10분간 세정 한 후 진공 증착기로 기판을 이송하였다. 이렇게 준비된 ΠΌ 투명 전극을 양극으로 사용하여 ITO 기판 상부에 화합물 A를 진공 증착하여 700 A두께의 정공 주입층을 형성하고 상기 주입층 상부에 화합물 B를 50 A의 두께로 증착한 후, 화합물 C를 1020 A의 두께로 증착하여 정공수송층을 형성하였다. 정공수송층 상부에 상기에서 합성예 19에서 얻은 화합물 12와 공지의 화합물 C-10을 동시쎄 호스트로 사용하고 도판트로 트리스 (2-페닐피리딘)이리듐 (III) [Ir(ppy)3]를 lOwt0/。로 도핑하여 진공 증착으로 400 A 두께의 발광층을 형성하였다. 여기서 화합물 12와 화합물 B-1은 1 : 1 비율로 사용되었다. 이어서 상기 발광층 상부에 화합물 D와 Liq를 동시에 1 : 1 비율로 진공 증착하여 300 A 두께의 전자수송층을 형성하고 상기 전자수송층 상부에 Liq l 5 A과 A1 1200A을 순차적으로 진공 증착 하여 음극을 형성함으로써 유기발광소자를 제작하였다. ΠΌ (Indium tin oxide) distilled water to a glass substrate coated with a thin film of 1500A Washed by ultrasonic. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Compound A was vacuum deposited on the ITO substrate using the prepared Π transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on the injection layer. Depositing a thickness of 1020 A to form a hole transport layer. Using compound 12 and C-10 of the known compounds obtained in Example 19 in the in the hole transport layer by co-theta host and a dopant tris (2-phenylpyridine) iridium lOwt (III) [Ir (ppy) 3] 0 Doped with /. And vacuum evaporation to form a light emitting layer of 400 A thickness. Compound 12 and Compound B-1 were used in a 1: 1 ratio. Subsequently, the compound D and Liq are simultaneously deposited in a 1: 1 ratio on the emission layer to form an electron transport layer having a thickness of 300 A, and Liq l 5 A and A1 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode. An organic light emitting device was manufactured.
상기 유가발광소자는 5층의 유기 박막층을 가지는 구조로 되어 있으며, 구체적으로 다음과 같다. The oil-emitting light emitting device has a structure having five organic thin film layers, specifically as follows.
ΠΌ/화합물 A(700A)/화합물 B(50A)/화합물 C(1020A)/EML [화합물 12:화합물 C-10:Ir(ppy)3 = X:X: 10%](400A)/화합물 D:Liq(300A)/Liq(15 A)/A1(1200 A)의 구조로 제작하였다. (X= 중량비) ΠΌ / Compound A (700A) / Compound B (50A) / Compound C (1020A) / EML [Compound 12: Compound C-10: Ir (ppy) 3 = X: X: 10%] ( 4 00A) / Compound D : it was prepared by the structure of Liq (3 00A) / Liq ( 15 a) / A1 (1200 a). (X = weight ratio)
화합물 A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'- diamine Compound A: N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'-diamine
화합물 B: 1 ,4,5,8,9, 1 1 -hexaazatriphenylene-hexacarbonitrile (HAT-CN), 화합물 C:N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phen^ 9H-fluoren-2-amine Compound B: 1,4,5,8,9, 1 1 -hexaazatriphenylene-hexacarbonitrile (HAT-CN), Compound C: N- (biphenyl-4-yl) -9,9-dimethyl-N- (4- ( 9-phenyl-9H-carbazol-3-yl) phen ^ 9H-fluoren-2-amine
화합물 D: 8-(4-(4,6-di(naphthalen-2-yl)-l ,3,5-triazin-2-yl)phenyl)quinoline 실시예 9 내지 13 Compound D: 8- (4- (4,6-di (naphthalen-2-yl) -l, 3,5-triazin-2-yl) phenyl) quinoline Examples 9-13
화합물 C-10 대신 공지 화합물 B-10, 화합물 B-31 , B-34, B-43 및 E-1을 각각 사용한 것을 제외하고 실시예 8과 동일한 방법으로 실시예 9 내지 13의 유기발광소자를 제작하였다. The organic light emitting diodes of Examples 9 to 13 were obtained by the same method as Example 8, except for using the known compounds B-10, B-31, B-34, B-43, and E-1 instead of the compound C-10. Produced.
비교예 4 내지 9
화합물 12와 화합물 C-10의 2종 호스트 대신 화합물 C-10을 단독 호스트를 사용, 화합물 B-10을 단독 호스트를 사용, 화합물 B-31을 단독 호스트를 사용， 화합물 B-34를 단독 호스트를 사용, 화합물 B-43을 단독 호스트를 사용 및 화합물 E-1을 단독 호스트로 사용한 것을 제외하고 실시예 8과 동일한 방법으로 비교예 4 내지 9의 유기발광소자를 제작하였다. 평가 II Comparative Examples 4 to 9 Compound C-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-31 is used as the sole host, Compound B-34 is the sole host. The organic light emitting diodes of Comparative Examples 4 to 9 were prepared in the same manner as in Example 8, except that Compound B-43 was used as the sole host and Compound E-1 was the sole host. Evaluation II
실시예 8 내지 13과 비교예 4 내지 9에 따른 유기발광소자의 발광효율 및 수명특성을 평가하였다. The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 8 to 13 and Comparative Examples 4 to 9 were evaluated.
구체적인 측정방법은 하기와 같고, 그 결과는 표 3과 같다. Specific measurement methods are as follows, and the results are shown in Table 3.
(1) 전압변화에 따른 전류밀도의 변화 측정 (1) Measurement of change of current density according to voltage change
제조된 유기발광소자에 대해, 전압올 0V 부터 10V까지 상승시키면서 전류- 전압계 (Keithley 2400)를 이용하여 단위소자에 흐르는 전류값을 측정하고， 측정된 전류값을 면적으로 나누어 결과를 얻었다. With respect to the manufactured organic light emitting device, the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
(2) 전압변화에 따른 휘도변화 측정 (2) Measurement of luminance change according to voltage change
제조된 유기발광소자에 대해, 전압을 0V 부터 10V까지 상승시키면서 휘도계 (Minolta Cs-IOOOA)를 이용하여 그 때의 휘도를 측정하여 결과를 얻었다. For the manufactured organic light emitting device, the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
(3) 발광효율 측정 (3) Measurement of luminous efficiency
상기 (1) 및 (2)로부터 측정된 휘도와 전류밀도 및 전압을 이용하여 동일 전류밀도 (10 mA/cm2)의 전류 효율 (cd/A) 을 계산하였다. The current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
(4) 수명 측정 (4) life measurement
휘도 (cd/m2)를 6000 cd/m2로 유지하고 전류 효율 (cd/A)이 97%로 감소하는 시간을 측정하여 결과를 얻었다. The results were obtained by measuring the time at which the luminance (cd / m 2 ) was maintained at 6000 cd / m 2 and the current efficiency (cd / A) decreased to 97%.
[표 3] TABLE 3
거 U호스트 제 2호스트 발광효율 (cd/A) 수명 T97(h) 실시예 8 화합물 12 C-10 49.5 150 Near U-host Second-host Luminous Efficiency (cd / A) Lifespan T97 (h) Example 8 Compound 12 C-10 49.5 150
실시예 9 화합물 12 B-10 50.0 125 Example 9 Compound 12 B-10 50.0 125
실시예 10 화합물 12 B-31 48.1 126 Example 10 Compound 12 B-31 48.1 126
실시예 1 1 화합물 12 B-34 48.5 150
실시예 12 화합물 12 B-43 51.0 140 Example 1 1 Compound 12 B-34 48.5 150 Example 12 Compound 12 B-43 51.0 140
실시예 13 화합물 12 E-1 51.0 1 10 Example 13 Compound 12 E-1 51.0 1 10
기준예 화합물 12 48.5 100 Reference Example Compound 12 48.5 100
비교예 4 C-10 16.5 10 Comparative Example 4 C-10 16.5 10
비교예 5 B-10 37.5 10 Comparative Example 5 B-10 37.5 10
비교예 6 B-31 2.5 0 Comparative Example 6 B-31 2.5 0
비교예 7 B-34 18.3 0 Comparative Example 7 B-34 18.3 0
비교예 8 B-43 2.8 10 Comparative Example 8 B-43 2.8 10
비교예 9 E-1 1.4 30 표 3을 참고하면, 실시예 8 내지 13에 따른 유기발광소자는 비교예 4 내只' 9에 따른 유기발광소자와 비교하여 발광효율 및 수^특성이 현저하게 개선된 것을 확인할 수 있다. 또한 실시예 8 내지 13에 따른 유기발광소자는 기준예에 따른 유기발광소자보다 발광효율 및 수명이 더욱 개선되었음을 알 수 있다. 본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다. Comparative Example 9 E-1 1.4 30 Referring to Table 3, the organic light emitting diode according to Examples 8 to 13 is significantly improved in the luminous efficiency and reception characteristics compared to the organic light emitting diode according to Comparative Example 4 Nag ' 9 You can see that. In addition, it can be seen that the organic light emitting device according to Examples 8 to 13 further improved luminous efficiency and lifespan than the organic light emitting device according to the reference example. The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
【부호의 설명] [Description of code]
100: 유기 발광 소자 100: organic light emitting device
105: 유기층 105: organic layer
1 10: 애노드 1 10: anode
120: 캐소드 120: cathode
130: 발광층
130: light emitting layer
Claims
【청구항 1】 【Claim 1】
하기 화학식 1로 표현되는 유기 화합물: 화학식 1] Organic compound represented by the following Chemical Formula 1: Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
Z1 내지 Z13은 각각 독립적으로 N 또는 CR3 이고, Z 1 to Z 13 are each independently N or CR 3 ,
Z1 내지 Z13중 적어도 하나는 N이고, ： At least one of Z 1 to Z 13 is N, :
L1은 단일 결합 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고, L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R1 내지 R10은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기， 치환 또는 비치환된 C6 내지 C12 아릴기 또는 이들의 조합이고,R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
R" 내지 R14 및 Ra는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 해테로고리기 또는 이들의 조합이고, R" to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or these It is a combination of
R1 내지 R14 및 Ra는 각각 독립적으로 존재하거나 인접한 두 개가 결합하여 고리를 형성하고, R 1 to R 14 and R a each exist independently or two adjacent ones combine to form a ring,
nl 및 n2는 각각 독립적으로 0 내지 2의 정수이다. nl and n2 are each independently integers from 0 to 2.
【청구항 2】 【Claim 2】
거 U항에서, In Port U,
L1은 치환 또는 비치환된 0-페닐렌기 및 치환 또는 비치환된 m-페닐렌기 중 적어도 하나를 포함하는 것인 유기 화합물.
L 1 is an organic compound comprising at least one of a substituted or unsubstituted 0-phenylene group and a substituted or unsubstituted m-phenylene group.
【청구항 3 ] [Claim 3]
게 1항에서， In paragraph 1,
L1은 단일 결합이거나 하기 그룹 1에 나열된 치환 또는 비치환된 기에서 선택된 하나인 유기 화합물: An organic compound where L 1 is a single bond or one selected from the substituted or unsubstituted groups listed in Group 1 below:
상기 그룹 1에서, In group 1 above,
R30 내지 R57은 각각 독립.적으로 수소, 중수소， 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C3 내지 C30 사이클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 헤테로고리기， 치환 또는 비치환된 아민기, 치환 또는 비치환된 C6 내지 C30 아릴아민기, 치환 또는 비치환된 C6 내지 C30 헤테로아릴아민기, 치환 또는 비치환된 C1 내지 C30 알콕시기, 할로겐, 시아노기, 히드록실기, 아미노기, 니트로기, 카르복실기, 페로세닐기 또는 이들의 조합이다. R 30 to R 57 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted Ringed C2 to C30 heterocyclic group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 heteroarylamine group, substituted or unsubstituted C1 to C30 It is an alkoxy group, halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, ferrocenyl group, or a combination thereof.
【청구항 4】 【Claim 4】
제 1항에서, In paragraph 1:
R1 내지 R4는 각각 독립적으로 수소, 중수소 또는 치환 또는 비치환된 C 1 내지 C 10 알킬기인 유기 화합물. R 1 to R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted C 1 to C 10 alkyl group.
【청구항 5】
제 1항에서, 【Claim 5】 In paragraph 1:
Z1 내지 Z13중 적어도 세 개는 N인 유기 화합물. An organic compound in which at least three of Z 1 to Z 13 are N.
【청구항 6】 【Claim 6】
게 1항에서, In paragraph 1,
Z1 내지 Z3는 모두 N이고, Z 1 to Z 3 are all N,
Z4 내지 Z13은 각각 독립적으로 N 또는 CRa이고, 여기서 Ra는 수소, 중수소 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합인 유기 화합물. Z 4 to Z 13 are each independently N or CR a , where R a is hydrogen, a deuterium substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C3 to C12 aryl group. An organic compound containing a C12 heterocyclic group or a combination thereof.
【청구항 7】 【Claim 7】
제 1항에서, In paragraph 1:
하기 화학식 3 또는 4로 표현되는 유기 화합물: Organic compounds represented by the following formula 3 or 4:
[화학식 3] [Formula 3]
상기 화학식 3 또는 4에서， In Formula 3 or 4,
Z1 내지 Z13은 각각 독립적으로 N 또는 CRa 이고， Z 1 to Z 13 are each independently N or CR a ,
Z1 내지 Z13중 적어도 하나는 N이고, At least one of Z 1 to Z 13 is N,
R1 내지 R10은 각각 독립적으로 수소., 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기 또는 이들의 조합이고, R 1 to R 10 are each independently hydrogen . , deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
R1 1 내지 R14 및 Ra는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기 또는 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합이고, R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C3 to C12 heterocyclic group, or It is a combination of these,
R1 내지 R" 및 Ra는 각각 독립적으로 존재하거나 인접한 두 개가 결합하여 고리를 형성하고, R 1 to R "and R a each exist independently or two adjacent ones combine to form a ring,
nl 및 n4는 각각 독립적으로 0 내지 2의 정수이고, nl and n4 are each independently integers from 0 to 2,
nl+n2+n3+n4>2 이다. nl+n2+n3+n4>2.
【청구항 8】 【Claim 8】
제 1항에서, In paragraph 1:
하기 그룹 2에 나열된 유기 화합물.
Organic compounds listed in Group 2 below.
TZSOlO/9lOZaM/X3d 8S
TZSOlO/9lOZaM/X3d 8S
[청구항 9】 [Claim 9]
게 1항에 따른 제 1 유기 화합물, 그리고 A first organic compound according to paragraph 1, and
카바졸 모이어티를 가지는 적어도 하나의 제 2 유기 화합물 At least one second organic compound having a carbazole moiety
을 포함하는 유기광전자소자용 조성물. A composition for an organic optoelectronic device containing a.
【청구항 10】 【Claim 10】
제 9항에서, In paragraph 9:
상기 제 2 유기 화합물은 The second organic compound is
하기 화학식 5로 표현되는 화합물, 및 하기 화학식 6으로 표현되는 모이어티와 하기 화학식 7로 표현되는 모이어티의 조합으로 이루어진 화합물 중 적어도 하나를 포함하는 유기광전자소자용 조성물:
[화학식 5] A composition for an organic optoelectronic device comprising at least one of a compound represented by the following Chemical Formula 5, and a compound consisting of a combination of a moiety represented by the following Chemical Formula 6 and a moiety represented by the following Chemical Formula 7: [Formula 5]
Y1은 단일 결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기， 치환 또는 비치환된 C2 내지 C20 알케닐렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기， 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기 또는 이들의 조합이고, Y 1 is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 divalent A heterocyclic group or a combination thereof,
Ar1은 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 헤테로고리기 또는 이들의 조합이고, Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R60 내지 R63은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C50 아릴기, 치환 또는 비치환된 C2 내지 C50 헤테로고리기 또는 이들의 조합이고, R 60 to R 63 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. ,
R60 내지 R63 및 Ar1 중 적어도 하나는 치환 또는 비치환된 트리페닐렌기 또는 치환 또는 비치환된 카바졸릴기를 포함하고， At least one of R 60 to R 63 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group,
[화학식 6] [화학식 7] [Formula 6] [Formula 7]
상기 화학식 6 또는 7에서, In Formula 6 or 7 above,
Y2 및 Y3는 각각 독립적으로 단일 결합， 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C2 내지 C20 알케닐렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기 또는 이들의 조합이고, Y 2 and Y 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted It is a C2 to C30 divalent heterocyclic group or a combination thereof,
Ar2 및 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 헤테로고리기 또는 이들의 조합이고,
R64 내지 R67은 각각 독립적으로 수소, 중수소， 치환 또는 비치환된 C1 내지 C20 알킬기， 치환 또는 비치환된 C6 내지 C50 아릴기, 치환 또는 비치환된 C2 내지 C50 헤테로고리기 또는 이들의 조합이고, Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R 64 to R 67 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. ,
상기 화학식 6의 인접한 두 개의 *는 상기 화학식 7의 두 개의 *와 결합하여 융합고리를 형성하고 상기 화학식 6에서 융합고리를 형성하지 않은 *는 각각 독립적으로 CRb이고, 여기서 Rb는 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기， 치환 또는 비치환된 C6 내지 C12 아릴기， 치환 또는 비치환된 C3 내지 C12 헤테로고리기 또는 이들의 조합이다. The two adjacent * of Formula 6 combine with the two * of Formula 7 to form a fused ring, and the * that does not form a fused ring in Formula 6 are each independently CR b , where R b is hydrogen, deuterium , a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
【청구항 1 1】 【Claim 1 1】
제 10항에서， In paragraph 10,
상기 화학식 5로 표현되는 제 2 유기 화합물은하기 화학식 5-1 내지 5-ΙΠ 중 적어도 하나로 표현되는 유기광전자소자용 조성물: The second organic compound represented by Formula 5 is a composition for an organic optoelectronic device represented by at least one of the following Formulas 5-1 to 5-ΙΠ:
5_1] [화학식 5-Π] 5_1] [Formula 5-Π]
상기 화학식 5-1 내지 5-ΙΠ에서, In the above formulas 5-1 to 5-ΙΠ,
Y1, Y4 및 Y5는 각각 독립적으로 단일 결합, 치환 또는 비치환된 C1 내지 Y 1 , Y 4 and Y 5 are each independently a single bond, substituted or unsubstituted C1 to
C20 알킬렌기, 치환 또는 비치환된 C2 내지 C20 알케닐렌기, 치환 또는 비치환된C20 alkylene group, substituted or unsubstituted C2 to C20 alkenylene group, substituted or unsubstituted
C6 내지 C30 아릴렌기 , 치환 또는 비치환된 C2 내지 C30 2가의 헤테로고리기
또는 이들의 조합이고, C6 to C30 arylene group, substituted or unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
Ατ'및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기， 치환 또는 비치환된 C2 내지 C30 해테로고리기 또는 이들의 조합이고， Ατ' and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R60 내지 Rw및 R6S 내지 R79는각각 독립적으로 수소, 증수소, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C50 아릴기， 치환 또는 비치환된 C2 내지 C50 헤테로고리기 또는 이들의 조합이다. R 60 to R w and R 6S to R 79 are each independently hydrogen, hydrogen hydrogen, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C50 aryl group, substituted or unsubstituted C2 to C50 hetero It is a cyclic group or a combination thereof.
【청구항 12】 【Claim 12】
제 10항에서， In paragraph 10,
상기 화학식 6으로 표현되는 모이어티와 상기 화학식 7로 표현되는 모이어티의 조합으로 이루어진 제 2 유기 화합물은 하기 그룹 4에 나열된 화합물에서 선택되는 유기광전자소자용 조성물: The second organic compound consisting of a combination of the moiety represented by Formula 6 and the moiety represented by Formula 7 is a composition for an organic optoelectronic device selected from the compounds listed in Group 4 below:
그룹 4] Group 4]
RECTIFIED SHEET (RULE 91 ) !SA/KR
RECTIFIED SHEET (RULE 91 ) !SA/KR
RECTIFIED SHEET (RULE 91) ISA/KR
RECTIFIED SHEET (RULE 91) ISA/KR
【청구항 13 ] [Claim 13]
서로 마주하는 애노드와 캐소드, 그리고 Anode and cathode facing each other,
상기 애노드와 상기 캐소드 사이에 위치하는 적어도 1층의 유기층 을 포함하고, Comprising at least one organic layer located between the anode and the cathode,
상기 유기층은 The organic layer is
발광층, 그리고 luminescent layer, and
상기 애노드와 상기 발광층 사이 또는 상기 캐소드와 상기 발광층 사이에 위치하는 보조층을 포함하며 , It includes an auxiliary layer located between the anode and the light-emitting layer or between the cathode and the light-emitting layer,
상기 발광층 또는 보조층은 제 1항에 따른 유기 화합물 또는 제 9항에 따른 유기광전자소자용 조성물을 포함하는 유기 광전자 소자ᅳ The light-emitting layer or auxiliary layer is an organic optoelectronic device containing the organic compound according to claim 1 or the composition for organic optoelectronic devices according to claim 9.
【청구항 14】 【Claim 14】
제 13항에 따른 유기 광전자 소자를 포함하는 표시 장치.
A display device comprising the organic optoelectronic device according to claim 13.
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| WO2022124367A1 (en) * | 2020-12-11 | 2022-06-16 | 日鉄ケミカル＆マテリアル株式会社 | Material for organic electroluminescent element and organic electroluminescent element |
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| KR102162404B1 (en) * | 2017-12-27 | 2020-10-06 | 삼성에스디아이 주식회사 | Compound for organic optoelectric device, composition for organic optoelectric device, organic optoelectric device and display device |
| KR20200125080A (en) * | 2019-04-26 | 2020-11-04 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| JP2024504058A (en) * | 2021-04-30 | 2024-01-30 | エルジー・ケム・リミテッド | organic light emitting device |
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| KR20110042004A (en) * | 2009-10-16 | 2011-04-22 | 에스에프씨 주식회사 | Fused aromatic compounds and organic light-emitting diode including the same |
| WO2011081431A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic light emitting compound, and organic electroluminescent device using same |
| KR20150090836A (en) * | 2014-01-29 | 2015-08-06 | 제일모직주식회사 | Composition for electron transport buffer layer and organic optoelectric device including the electron transport buffer layer and display device |
-
2015
- 2015-12-18 KR KR1020150181934A patent/KR20170073245A/en not_active Application Discontinuation
-
2016
- 2016-09-21 WO PCT/KR2016/010521 patent/WO2017104946A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008056746A1 (en) * | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
| WO2008119666A1 (en) * | 2007-03-29 | 2008-10-09 | Basf Se | Heterocyclic bridged biphenyls |
| KR20110042004A (en) * | 2009-10-16 | 2011-04-22 | 에스에프씨 주식회사 | Fused aromatic compounds and organic light-emitting diode including the same |
| WO2011081431A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic light emitting compound, and organic electroluminescent device using same |
| KR20150090836A (en) * | 2014-01-29 | 2015-08-06 | 제일모직주식회사 | Composition for electron transport buffer layer and organic optoelectric device including the electron transport buffer layer and display device |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190001116A (en) * | 2017-06-26 | 2019-01-04 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device and composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102146790B1 (en) * | 2017-06-26 | 2020-08-21 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device and composition for organic optoelectronic device and organic optoelectronic device and display device |
| US11588116B2 (en) | 2020-03-11 | 2023-02-21 | Lg Chem, Ltd. | Organic light emitting device |
| WO2022124367A1 (en) * | 2020-12-11 | 2022-06-16 | 日鉄ケミカル＆マテリアル株式会社 | Material for organic electroluminescent element and organic electroluminescent element |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20170073245A (en) | 2017-06-28 |
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