KR20130025268A - Novel compounds for organic electronic material and organic electroluminescence device using the same - Google Patents
Novel compounds for organic electronic material and organic electroluminescence device using the same Download PDFInfo
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- KR20130025268A KR20130025268A KR1020110088684A KR20110088684A KR20130025268A KR 20130025268 A KR20130025268 A KR 20130025268A KR 1020110088684 A KR1020110088684 A KR 1020110088684A KR 20110088684 A KR20110088684 A KR 20110088684A KR 20130025268 A KR20130025268 A KR 20130025268A
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- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- halogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 239000012776 electronic material Substances 0.000 title claims abstract description 23
- 238000005401 electroluminescence Methods 0.000 title abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 64
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 63
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- 150000002367 halogens Chemical group 0.000 claims abstract description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 26
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 9
- 125000000732 arylene group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- -1 cyano, N-carbazolyl Chemical group 0.000 claims description 146
- 239000000463 material Substances 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 239000002019 doping agent Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims 1
- 150000002602 lanthanoids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 5
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 230000005611 electricity Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- NXTRQJAJPCXJPY-UHFFFAOYSA-N 910058-11-6 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 NXTRQJAJPCXJPY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PZJHQKUZJMOBOU-UHFFFAOYSA-N C1C=C(c(cccc2)c2N2c3ccccc3)C2=CC1 Chemical compound C1C=C(c(cccc2)c2N2c3ccccc3)C2=CC1 PZJHQKUZJMOBOU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 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
- 230000000903 blocking effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- HBBKKZVRZMEYOS-UHFFFAOYSA-N 1,8-phenanthroline Chemical compound N1=CC=C2C3=NC=CC=C3C=CC2=C1 HBBKKZVRZMEYOS-UHFFFAOYSA-N 0.000 description 1
- AJCSVUVYIMRJCB-UHFFFAOYSA-N 1,9-phenanthroline Chemical compound C1=NC=C2C3=NC=CC=C3C=CC2=C1 AJCSVUVYIMRJCB-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N C1C=CC=CC1 Chemical compound C1C=CC=CC1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- NROZBXHYFBEUPJ-UHFFFAOYSA-N CC(C)(c1ccccc1-1)c(cc2)c-1c1c2c2ccccc2[n]1-c1nc(cccc2)c2c(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)n1 Chemical compound CC(C)(c1ccccc1-1)c(cc2)c-1c1c2c2ccccc2[n]1-c1nc(cccc2)c2c(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)n1 NROZBXHYFBEUPJ-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- JHEGGDPKQYYLND-UHFFFAOYSA-M N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Li+].C1=C(C=CC2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC(=CC12)C1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2)C2=CC1=CC=CC=C1C=C2 Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Li+].C1=C(C=CC2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC(=CC12)C1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2)C2=CC1=CC=CC=C1C=C2 JHEGGDPKQYYLND-UHFFFAOYSA-M 0.000 description 1
- QWKFYAGZLGBCIE-UHFFFAOYSA-N OC(C(BC=C1)=C1C1=COC=C1)=O Chemical compound OC(C(BC=C1)=C1C1=COC=C1)=O QWKFYAGZLGBCIE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- UUESRJFGZMCELZ-UHFFFAOYSA-K aluminum;2-methylquinoline-8-carboxylate;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21 UUESRJFGZMCELZ-UHFFFAOYSA-K 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
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- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
본 발명은 신규한 유기 전자재료용 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것이다.The present invention relates to a novel compound for organic electronic materials and an organic electroluminescent device comprising the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2, Ir(ppy)3 및 Firpic 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다. The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) 2 , Ir (ppy) 3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.
인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있고, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용해 고성능의 OLED을 개발한 바 있다. CBP is the most widely known host material for phosphorescent emitters to date, and high-efficiency OLEDs using hole blocking layers such as BCP and BAlq are known. I've done it.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 단점을 갖고 있다. OLED에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력효율은 전압에 반비례하고, 따라서 OLED의 소비 전력을 낮으려면 전력 효율을 높여야 한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 사용되던 BAlq 또는 CBP와 같은 종래재료의 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. 또한, OLED 소자에 사용할 경우 수명 측면에서도 결코 만족스럽지 못하였다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the OLED, power efficiency = [(π / voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). Also, when used in OLED devices, they were never satisfactory in terms of lifetime.
한편, 국제특허공보 제WO 2006/049013호에는 축합 이환기를 골격으로 하는 유기 전기 발광 소재용 화합물을 언급하고 있다. 그러나 상기 문헌에는, 질소 함유 축합 이환기 골격을 가지면서, 방향족 고리가 융합된 헤테로시클로알킬 또는 시클로알킬, 및 이 화합물과 융합된 카바졸 기를 모두 겸비한 구조를 개시하고 있지 않다.On the other hand, International Patent Publication No. WO 2006/049013 mentions a compound for an organic electroluminescent material having a condensed bicyclic group as a skeleton. However, the document does not disclose a structure having both a nitrogen-containing condensed bicyclic skeleton and having both a heterocycloalkyl or a cycloalkyl fused with an aromatic ring and a carbazole group fused with this compound.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 전자재료용 화합물을 제공하는 것이며 둘째로, 상기 유기 전자재료용 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide a compound for organic electronic material having a good skeleton having an excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems. It is to provide a high efficiency and long life organic electroluminescent element employing a compound for a material as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 전자재료용 화합물은 기존 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to a compound for an organic electronic material represented by the following formula (1) and an organic electroluminescent device comprising the same, the compound for an organic electronic material according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional material The driving life of the device is very excellent and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.
[화학식 1] [Formula 1]
[상기 화학식 1에서,[In Formula 1,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)시클로알킬렌이고;L 1 and L 2 are each independently a single bond, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) Cycloalkylene;
X1은 CH 또는 N이며;X 1 is CH or N;
Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며;Y 1 and Y 2 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ;
R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록실이거나, R4 및 R5은 각각 독립적으로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxyl, or each of R 4 and R 5 independently or without adjacent substituents and fused rings It may be linked to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, the alicyclic ring formed above And the carbon atoms of the monocyclic or polycyclic aromatic rings are at least one hete selected from nitrogen, oxygen and sulfur. May be substituted with a raw atom;
R6 내지 R8 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;R 6 to R 8 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c 및 e는 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 동일하거나 상이할 수 있고;a, b, c and e are each independently an integer of 1 to 4, and may be the same or different when two or more integers;
d은 1 내지 3의 정수이며, 2 이상의 정수인 경우 동일하거나 상이할 수 있고;d is an integer of 1 to 3, and may be the same or different when it is an integer of 2 or more;
상기 헤테로시클로알킬, 헤테로아릴렌 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]Wherein said heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 터페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 페난트릴은 1-페난트릴, 2-페난트릴, 3-페난트릴, 4-페난트릴, 9-페난트릴을 포함하며, 나프타세닐은 1-나프타세닐, 2-나프타세닐, 9-나프타세닐을 포함하며, 피렌일은 1-피렌일, 2-피렌일, 4-피렌일을 포함하며, 비페닐은 2-비페닐, 3-비페닐, 4-비페닐을 포함하며, 터페닐은 p-터페닐-4-일기, p-터페닐-3-일기, p-터페닐-2-일기, m-터페닐-4-일기, m-터페닐-3-일기, m-터페닐-2-일기을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연걸된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 다이벤조퓨란일, 다이벤조티오페닐, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴, 아크리디닐, 페난트롤리닐, 페나지닐, 페노싸이아지닐, 페녹사지닐 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다. 상기 피롤릴은 1-피롤릴, 2-피롤릴, 3-피롤릴을 포함하며, 피리딜은 2-피리딜, 3-피리elf, 4-피리딜을 포함하며, 인돌릴은 1-인돌릴, 2-인돌릴, 3-인돌릴, 4-인돌릴, 5-인돌릴, 6-인돌릴, 7-인돌릴을 포함하며, 이소인돌릴은 1-이소인돌릴, 2-이소인돌릴, 3-이소인돌릴, 4-이소인돌릴, 5-이소인돌릴, 6-이소인돌릴, 7-이소인돌릴을 포함하며, 퓨릴은 2-퓨릴, 3-퓨릴을 포함하며, 벤조퓨란일은 2-벤조퓨란일, 3-벤조퓨란일, 4-벤조퓨란일, 5-벤조퓨란일, 6-벤조퓨란일, 7-벤조퓨란일을 포함하며, 이소벤조퓨란일은 1-이소벤조퓨란일, 3-이소벤조퓨란일, 4-이소벤조퓨란일, 5-이소벤조퓨란일, 6-이소벤조퓨란일, 7-이소벤조퓨란일을 포함하며, 퀴놀릴은 3-퀴놀릴, 4-퀴놀릴, 5-퀴놀릴, 6-퀴놀릴, 7-퀴놀릴, 8-퀴놀릴을 포함하며, 이소퀴놀릴은 1-이소퀴놀릴, 3-이소퀴놀릴, 4-이소퀴놀릴, 5-이소퀴놀릴, 6-이소퀴놀릴, 7-이소퀴놀릴, 8-이소퀴놀릴기을 포함하며, 퀴녹살리닐은 2-퀴녹살리닐, 5-퀴녹살리닐, 6-퀴녹살리닐을 포함하며, 카바졸릴은 1-카바졸릴, 2-카바졸릴, 3-카바졸릴, 4-카바졸릴, 9-카바졸릴을 포함하며, 페난트리딘일은 1-페난트리딘일, 2-페난트리딘일, 3-페난트리딘일, 4-페난트리딘일, 6-페난트리딘일, 7-페난트리딘일, 8-페난트리딘일, 9-페난트리딘일, 10-페난트리딘일을 포함하며, 아크리디닐은 1-아크리디닐, 2-아크리디닐, 3-아크리디닐, 4-아크리디닐, 9-아크리디닐을 포함하며, 페난트롤리닐은 1,7-페난트롤린-2-일기, 1,7-페난트롤린-3-일기, 1,7-페난트롤린-4-일기, 1,7-페난트롤린-5-일기, 1,7-페난트롤린-6-일기, 1,7-페난트롤린-8-일기, 1,7-페난트롤린-9-일기, 1,7-페난트롤린-10-일기, 1,8-페난트롤린-2-일기, 1,8-페난트롤린-3-일기, 1,8-페난트롤린-4-일기, 1,8-페난트롤린-5-일기, 1,8-페난트롤린-6-일기, 1,8-페난트롤린-7-일기, 1,8-페난트롤린-9-일기, 1,8-페난트롤린-10-일기, 1,9-페난트롤린-2-일기, 1,9-페난트롤린-3-일기, 1,9-페난트롤린-4-일기, 1,9-페난트롤린-5-일기, 1,9-페난트롤린-6-일기, 1,9-페난트롤린-7-일기, 1,9-페난트롤린-8-일기, 1,9-페난트롤린-10-일기, 1,10-페난트롤린-2-일기, 1,10-페난트롤린-3-일기, 1,10-페난트롤린-4-일기, 1,10-페난트롤린-5-일기, 2,9-페난트롤린-1-일기, 2,9-페난트롤린-3-일기, 2,9-페난트롤린-4-일기, 2,9-페난트롤린-5-일기, 2,9-페난트롤린-6-일기, 2,9-페난트롤린-7-일기, 2,9-페난트롤린-8-일기, 2,9-페난트롤린-10-일기, 2,8-페난트롤린-1-일기, 2,8-페난트롤린-3-일기, 2,8-페난트롤린-4-일기, 2,8-페난트롤린-5-일기, 2,8-페난트롤린-6-일기, 2,8-페난트롤린-7-일기, 2,8-페난트롤린-9-일기, 2,8-페난트롤린-10-일기, 2,7-페난트롤린-1-일기, 2,7-페난트롤린-3-일기, 2,7-페난트롤린-4-일기, 2,7-페난트롤린-5-일기, 2,7-페난트롤린-6-일기, 2,7-페난트롤린-8-일기, 2,7-페난트롤린-9-일기, 2,7-페난트롤린-10-일기을 포함하며, 페나지닐은 1-페나지닐, 2-페나지닐을 포함하며, 페노싸이아지닐은 1-페노싸이아지닐, 2-페노싸이아지닐, 3-페노싸이아지닐, 4-페노싸이아지닐, 10-페노싸이아지닐을 포함하며, 페녹사지닐은 1-페녹사지닐, 2-페녹사지닐, 3-페녹사지닐, 4-페녹사지닐, 10-페녹사지닐을 포함하며, 옥사졸릴은 2-옥사졸릴, 4-옥사졸릴, 5-옥사졸릴을 포함하며, 옥사디아졸은 2-옥사디아졸릴, 5-옥사디아졸릴을 포함하며, 퓨라잔일은 3-퓨라잔일을 포함하며, 다이벤조퓨란일은 1-다이벤조퓨란일, 2-다이벤조퓨란일, 3-다이벤조퓨란일, 4-다이벤조퓨란일을 포함하며, 다이벤조싸이오페닐은 1-다이벤조싸이오페닐, 2-다이벤조싸이오페닐, 3-다이오벤조싸이오페닐, 4-다이오벤조싸이오페닐을 모두 포함한다.Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, But are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, phenanthryl includes 1-phenanthryl, Phenanthryl, 9-phenanthryl, 9-phenanthryl, naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, pyranyl includes 1-pyrene, Biphenyl, 3-biphenyl, 4-biphenyl, terphenyl includes p-terphenyl-4-yl group, p-terphenyl- Yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, fura Monocyclic heteroaryl such as residue, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalinyl , Polycyclic heteroaryls such as carbazolyl, phenantridinyl, benzodioxolyl, acridinyl, phenanthrolinyl, phenazinyl, phenthiazininyl, phenoxazinyl, and their corresponding N-oxides (e.g., Pyridyl N-oxide, quinolyl N-oxide), Of the like, but a quaternary salt, and the like. The pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl includes 2-pyridyl, 3-pyrielf, 4-pyridyl, and indolyl is 1-indolyl , 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, isoindoleyl includes 1-isoindoleyl, 2-isoindoleyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolinyl, 7-isoindolinyl, furyl includes 2-furyl, 3-furyl, benzofuranyl is 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, isobenzofuranyl is 1-isobenzofuranyl, 3 Isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, and quinolyl is 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, Quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, quinoxalinyl, quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, And the carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl and phenanthridinyl includes 1-phenanthridinyl, And the acridinyl includes 1-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, Acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenanthrolinyl includes 1,7-phenanthroline- A 1,7-phenanthroline-5-yl group, a 1,7-phenanthroline-6-yl group, a 1,7-phenanthroline- Yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline 3-yl group, 1,8-phen Yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline A 1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, A 1,1-phenanthroline-6-yl group, a 1,9-phenanthroline-7-yl group, a 1,9-phenanthroline- , 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1 , 2,9-phenanthroline-1-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline- A 2,9-phenanthroline-7-yl group, a 2,9-phenanthroline-8-yl group, a 2,9-phenanthroline- A thiol group such as a troline-10-yl group, a 2,8-phenanthroline-1-yl group, a 2,8-phenanthroline- Yl group, a 2,8-phenanthroline-9-yl group, a 2,8-phenanthroline-6-yl group, Yl group, a 2,7-phenanthroline-4-yl group, a 2,7-phenanthroline-1-yl group, 6-yl group, 2,7-phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline- Wherein the phenazinyl includes 1-phenazinyl, 2-phenazinyl, and the phenothiazinyl is 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4- Azoxycarbonyl, azinyl, 10-phenothiazinyl, and the phenoxazinyl includes 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, Oxazolyl includes 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, oxadiazole includes 2-oxadiazolyl, 5-oxadiazolyl, furazanyl includes 3-purazanyl , Dibenzofuranyl includes 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, and dibenzo EO phenyl includes all of 1-dibenzo thiophenyl, 2-benzo thiophenyl, 3-benzo diode thiophenyl, 4-benzo diode thiophenyl.
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 바람직하게는 (C1-C20)알킬이고, 더 바람직하게는 (C1-C10)알킬이며, ‘(C6-C30)아릴’기는 바람직하게는 (C6-C20)아릴이다. ‘(C2-C30)헤테로아릴’기는 바람직하게는 (C2-C20)헤테로아릴이다. ‘(C3-C30)시클로알킬’기는 바람직하게는 (C3-C20)시클로알킬이고, 더 바람직하게는 (C3-C7)시클로알킬이다. ‘(C2-C30)알케닐 또는 알키닐’기는 바람직하게는 (C2-C20)알케닐 또는 알키닐이고, 더 바람직하게는 (C2-C10)알케닐 또는 알키닐이다.Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl. The '(C2-C30) heteroaryl' group is preferably (C2-C20) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 L1, L2, R1 내지 R8 및 R11 내지 R17에 더 치환되는 치환기는 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록실로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' means a case where is further substituted with an unsubstituted substituent, the L 1 , L 2 , R 1 to R 8 and R 11 to R 17 Substituents further substituted for are deuterium, halogen, (C1-C30) alkyl, halogen-substituted (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1-C30) alkyl Substituted (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, tri (C1- C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) al Kenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl , (C1-C30) alkyl (C6-C30) ) At least one selected from the group consisting of aryl, carboxyl, nitro and hydroxyl.
구체적으로, 상기 L1 및 L2은 각각 독립적으로 단일결합, (C2-C30)헤테로아릴렌, (C6-C30)아릴렌, 또는 (C3-C30)시클로알킬렌이고; X1은 CH 또는 N이며; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며; R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, N-카바졸릴, -NR11R12 또는 -SiR13R14R15이거나, 상기 R4 및 R5은 각각 독립적으로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R6 내지 R8는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; R11 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; 상기 L1 및 L2의 아릴렌, 헤테로아릴렌 및 시클로알킬렌, R1 내지 R8 및 R11 내지 R15의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Specifically, L 1 and L 2 are each independently a single bond, (C2-C30) heteroarylene, (C6-C30) arylene, or (C3-C30) cycloalkylene; X 1 is CH or N; Y 1 and Y 2 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ; R 1 to R 5 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, N-carbazolyl, -NR 11 R 12 or -SiR 13 R 14 R 15 , wherein R 4 and R 5 are each independently linked to a (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without an adjacent substituent and a fused ring to form an alicyclic ring and May form a monocyclic or polycyclic aromatic ring, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur; R 6 to R 8 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; R 11 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; Arylene, heteroarylene and cycloalkylene of L 1 and L 2 , R 1 to R 8 And alkyl, aryl and heteroaryl of R 11 to R 15 are each deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 1 -C 30) alkyl (C6-C30) aryl, (C2-C30) heteroaryl, (C6-C30) aryl substituted (C2-C30) heteroaryl, (C3-C30) cycloalkyl and (C6-C30) ar (C1-C30) It may be further substituted with one or more substituents selected from the group consisting of alkyl.
상기 L1 및 L2은 각각 독립적으로 단일결합, 시클로프로필렌, 시클로부틸렌, 시클로펜틸렌, 시클로헥실렌, 시클로헵틸렌, 시클로옥틸렌, 페닐렌, 나프틸렌, 비페닐렌, 터페닐렌, 안트릴렌, 인데닐렌, 플루오레닐렌, 페난트릴렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 크라이세닐렌, 나프타세닐렌, 플루오란텐일, 퓨릴렌, 티오페닐렌, 피롤릴렌, 이미다졸릴렌, 피라졸릴렌, 티아졸릴렌, 티아디아졸릴렌, 이소티아졸릴렌, 이속사졸릴렌, 옥사졸릴렌, 옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 퓨라잔일렌, 피리딜렌, 피라진일렌, 피리미딘일렌, 피리다진일렌, 벤조퓨란일렌, 벤조티오펜일렌, 이소벤조퓨란일렌, 벤조이미다졸릴렌, 벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 이소인돌릴렌, 인돌릴렌, 인다졸릴렌, 벤조티아디아졸릴렌, 퀴놀릴렌, 이소퀴놀릴렌, 신놀리닐렌, 퀴나졸리닐렌, 퀴녹살리닐렌, 카바졸릴렌, 페난트리딘일렌, 벤조디옥솔릴렌, 다이벤조퓨란닐렌 및 다이벤조싸이오페닐렌으로 이루어진 군에서 선택되는 것이 바람직하며, 상기 L1 및 L2는 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.L 1 and L 2 are each independently a single bond, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, phenylene, naphthylene, biphenylene, terphenylene, Anthylene, indenylene, fluorenylene, phenanthryl, triphenylenylene, pyrenylene, peryleneylene, chrysenylene, naphthacelene, fluoranthenyl, furylene, thiophenylene, pyrroylene, already Dazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, furazanyl Benzene, pyridylene, pyrazinylene, pyrimidinylene, pyridazineylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolyl Lene, benzoxazolylene, isoindoleylene, indolylene, phosphorus Zoleylene, benzothiadiazolylene, quinolylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxoleylene, dibenzofuranylene and di It is preferably selected from the group consisting of benzothiophenylene, wherein L 1 and L 2 are each deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted with halogen, (C6-C30) Aryl, (C1-C30) alkyl (C6-C30) aryl, (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl and (C6 It may be further substituted with one or more substituents selected from the group consisting of -C30) ar (C1-C30) alkyl.
상기 Y1 및 Y2는 서로 독립적으로 하기 구조에서 선택된다.Y 1 and Y 2 are independently selected from the following structures.
더욱 구체적으로 상기 
본 발명에 따른 유기 전자재료용 화합물로는 대표적으로 하기의 화합물을 들 수 있다. Typical compounds for organic electronic materials according to the present invention include the following compounds.
본 발명에 따른 유기 전자재료용 화합물은 하기 반응식에 나타난 바와 같이 제조될 수 있다.The compound for an organic electronic material according to the present invention can be prepared as shown in the following scheme.
[반응식 1][Reaction Scheme 1]
[상기 반응식 1에서, L1, L2, X1, Y1, Y2, R1 내지 R5, a, b, c, d 및 e는 상기 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.][In Reaction Formula 1, L 1 , L 2 , X 1 , Y 1 , Y 2 , R 1 to R 5 , a, b, c, d and e are the same as defined in Formula 1, Hal is halogen to be.]
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖는 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 전자재료용 화합물을 하나 이상 포함한다. 또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 유기 전자재료용 화합물을 호스트 물질로 사용할 수 있다. In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound for an organic electronic material of Chemical Formula 1. In addition, the organic material layer includes a light emitting layer, in which the compound for an organic electronic material of Formula 1 may be used as a host material.
또한 본 발명에 따른 호스트와 함께 사용되는 유기 전계 발광 소자용 인광 도판트에는 대표적으로 하기 화학식 2의 화합물이 있다. In addition, a phosphorescent dopant for an organic electroluminescent device used with a host according to the present invention typically includes a compound represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
MM 1One LL 101101 LL 102102 LL 103103
상기 화학식 2에서,In Formula 2,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C2-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl or halogen;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는 
구체적으로 상기 화학식 2의 도판트 화합물로서 다음과 같은 화합물을 사용하는 것이 바람직하다. Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.
본 발명의 유기 전계 발광 소자는 화학식 1의 유기 전자재료용 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention includes a compound for an organic electronic material of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 전자재료용 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the compound for the organic electronic material of Formula 1, Group 1, Group 2, 4 cycle, 5 cycle transition metals, lanthanum series metals and organic metal of d-transition element It may further include one or more metal or complex compounds selected from the group consisting of, and further, the organic material layer may further include a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 전자재료용 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. In addition, the organic material layer may include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the compound for organic electronic materials to form an organic light emitting device that emits white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO X (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 전자재료용 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. 또한, 본 발명에 따른 유기 전자재료용 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The compound for an organic electronic material according to the present invention has an advantage of manufacturing an OLED device having excellent luminous efficiency and excellent lifespan characteristics of the device, and having excellent driving life of the device. In addition, the compound for an organic electronic material according to the present invention has high electron transfer efficiency, which prevents crystallization during device fabrication and improves current characteristics of the device due to good layer formation, thereby lowering the driving voltage of the device and improving power efficiency. There is an advantage to manufacture an OLED device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전자 재료용 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of a device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.
[제조예 1] 화합물 18의 제조Preparation Example 1 Preparation of Compound 18
화합물 compound 1-11-1 의 제조Manufacturing
2,4-디클로로퀴나졸린 (50g, 251mmol)과 디벤조[b,d]퓨란-4-일보로산 (53.2g, 251mmol)을 톨루엔 (1L)와 물 (200mL)의 혼합용액에 녹인 후 Pd(PPh3)4 (14.5g, 12.5mmol)과 Na2CO3 (80g, 755mmol)을 첨가하였다. 이 혼합물을 80℃에서 20시간 동안 교반하였다. 상기 반응 혼합물을 상온으로 냉각시키고 염화암모늄 수용액 (200mL)로 반응을 종결시킨 시킨 후 EA (1L)로 추출한 후, 수층은 다시 디클로로메탄 (1L)으로 추출하였다. 얻어진 유기층을 무수MgSO4로 건조하고, 유기용매는 감압하에서 제거하였다. 얻어진 고체는 실리카겔로 여과 후 용매는 감압하에서 제거하였다. 얻어진 고체를 EA (100mL)로 씻어주어 화합물 1-1 (50 g, 74%)을 얻었다.2,4-dichloroquinazolin (50g, 251mmol) and dibenzo [b, d] furan-4-ylborolic acid (53.2g, 251mmol) were dissolved in a mixed solution of toluene (1L) and water (200mL) and then Pd (PPh 3 ) 4 (14.5 g, 12.5 mmol) and Na 2 CO 3 (80 g, 755 mmol) were added. The mixture was stirred at 80 ° C. for 20 hours. The reaction mixture was cooled to room temperature, the reaction was terminated with aqueous ammonium chloride solution (200 mL), extracted with EA (1 L), and the aqueous layer was extracted with dichloromethane (1 L) again. The obtained organic layer was dried over anhydrous MgSO 4 , and the organic solvent was removed under reduced pressure. The obtained solid was filtered through silica gel, and the solvent was removed under reduced pressure. The obtained solid was washed with EA (100 mL) to give compound 1-1 (50 g, 74%).
화합물 compound 1-21-2 의 제조Manufacturing
9-패닐-9H-카바졸-3-일보론산 (30g, 149mmol), 1-브로모-2-나이트로벤젠 (51g, 178.8mmol), K2CO3 (52g, 372.5mmol)과 Pd(PPh3)4 (6.8g, 5.8mmol)을 톨루엔(600mL), EtOH(150mL)와 정제수(150mL)의 혼합용매에 투입 후 하룻동안 환류 교반 하였다. 반응 종결 후 실온으로 냉각한 뒤 정치하여 수층을 제거하였다. 유기층은 농축 후 MC로 trituration 한 후 여과하여 화합물 1-2 (50g, 92 %)을 얻었다. 9-Fanyl-9H-carbazol-3-ylboronic acid (30 g, 149 mmol), 1-bromo-2-nitrobenzene (51 g, 178.8 mmol), K 2 CO 3 (52 g, 372.5 mmol) and Pd (PPh 3 ) 4 (6.8 g, 5.8 mmol) were added to a mixed solvent of toluene (600 mL), EtOH (150 mL) and purified water (150 mL), followed by stirring under reflux for one day. After completion of the reaction, the mixture was cooled to room temperature and left to stand to remove the aqueous layer. The organic layer was concentrated, triturated with MC, and filtered to obtain Compound 1-2 (50 g, 92%).
화합물 compound 1-31-3 의 제조Manufacturing
화합물 1-2 (50g, 137mmol)을 P(OEt)3 (300ml)와 1,2-디클로로벤젠(300mL)에 투입 후 150℃에서 하룻동안 교반하였다. 반응 종결 후 감압농축 후 EA로 추출한 후 유기층을 농축하였다. 실리카 컬럼 정제하여 화합물 1-3 (32g, 70%)을 얻었다. Compound 1-2 (50 g, 137 mmol) was added to P (OEt) 3 (300 ml) and 1,2-dichlorobenzene (300 mL), followed by stirring at 150 ° C. for one day. After completion of the reaction, the mixture was concentrated under reduced pressure, extracted with EA, and the organic layer was concentrated. Silica column purification gave compound 1-3 (32 g, 70%).
화합물 compound 1818 의 제조Manufacturing
화합물 1-1 (5.5g, 16.5mmol), 화합물 1-3 (5.0g, 15mmol)을 DMF (80mL)에 현탁한 뒤 60% NaH (930mg, 23.2mmol)를 상온에서 투입하고 12시간 동안 교반하였다. 정제수(1L)를 투입 후 감압여과하였다. 얻어진 고체를 MeOH/EA로 trituration하고 DMF로 trituration한 후 EA/THF로 trituration하였다. MC로 녹여 실리카 여과한 후 MeOH/ EA로 trituration하여 화합물 18 (4.6g, 48.9%)를 얻었다.Compound 1-1 (5.5 g, 16.5 mmol) and compound 1-3 (5.0 g, 15 mmol) were suspended in DMF (80 mL), and 60% NaH (930 mg, 23.2 mmol) was added at room temperature and stirred for 12 hours. . Purified water (1L) was added and filtered under reduced pressure. The obtained solid was triturated with MeOH / EA, triturated with DMF, and triturated with EA / THF. After dissolving with MC and silica filtration, trituration with MeOH / EA gave compound 18 (4.6 g, 48.9%).
MS/FAB found 627, calculated 626.70
MS / FAB found 627, calculated 626.70
[실시예1] 본 발명에 따른 유기 전자 재료용 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using a Compound for Organic Electronic Materials According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작한다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용한다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-다이일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐벤젠-1,4-다이아민) (N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4- diphenylbenzene-1,4-diamine))을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착한다. 이어서 진공 증착 장비 내의 다른 셀에 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐 (N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl)을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착한다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시킨다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명의 화합물18을 넣고, 또 다른 셀에는 D-7을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4중량%으로 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착한다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸 (2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)을 넣고, 또다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 50중량%으로 도핑함으로서 30nm의 전자 전달층을 증착한다. 이어서 전자 주입층으로서 리튬 퀴놀레이트를 1 내지 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다.An OLED device having a structure using the light emitting material of the present invention is produced. First, the transparent electrode ITO thin film (15Ω / □) obtained from OLED glass (manufactured by Samsung-Corning) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol. use. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ′ -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) (N 1 , N 1 ' -([1,1'-biphenyl] -4,4' -diyl) bis (N 1- (naphthalen-1-yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine)) and evacuated until the vacuum in the chamber reaches 10 -6 torr. A current is applied to the cell and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl (N, N'-di) was added to another cell in the vacuum deposition equipment. (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl) is added thereto, and a 20 nm-thick hole transport layer is deposited on the hole injection layer by evaporation by applying a current to the cell. After the hole injection layer and the hole transport layer are formed, a light emitting layer is deposited thereon as follows. Compound 18 of the present invention as a host in one cell in the vacuum deposition equipment, D-7 in each of the other cells, and then evaporated at a different rate of the two materials by doping at 4% by weight to 30nm thickness on the hole transport layer The light emitting layer of is deposited. Subsequently, one cell as the electron transporting layer on the light emitting layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 in one cell as the electron transporting layer on the light emitting layer -Phenyl-1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole Lithium quinolate is added to another cell, and the electron transport layer of 30 nm is deposited by doping at 50 wt% by evaporating the two materials at different rates. Subsequently, lithium quinolate was deposited to a thickness of 1 to 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device.
그 결과, 5.6 V의 전압에서 44.7 mA/cm2의 전류가 흘렀으며, 3400 cd/m2의 적색발광이 확인되었다. As a result, a current of 44.7 mA / cm 2 flowed at a voltage of 5.6 V, and red light emission of 3400 cd / m 2 was confirmed.
[비교예 1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Fabrication of OLED device using light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-다이카바졸-바이페닐 (4,4‘-N,N'-dicarbazole-biphenyl)을 이용하고, 도판트에는 화합물 D-11을 사용하여 발광층을 증착하고, 발광층과 전자 전달층 사이에 정공 저지층으로 알루미늄(III)비스(2-메틸-8-퀴놀리네이토)4-페닐페놀레이트 (aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate)을 10nm 두께로 증착한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl) is used as a light emitting material and compound D-11 is used as a dopant. A light emitting layer was deposited and aluminum (III) bis (2-methyl-8-quinolinate) 4-phenylphenolate (aluminum (III) bis (2-methyl-8) was used as a hole blocking layer between the light emitting layer and the electron transporting layer. OLED device was manufactured in the same manner as in Example 1, except that -quinolinato) 4-phenylphenolate) was deposited to a thickness of 10 nm.
그 결과, 8.2 V의 전압에서 20.0 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다. As a result, a current of 20.0 mA / cm 2 flowed at a voltage of 8.2 V, and red light emission of 1000 cd / m 2 was confirmed.
Claims (10)
[화학식 1]
[상기 화학식 1에서,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)시클로알킬렌이고;
X1은 CH 또는 N이며;
Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며;
R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록실이거나, R4 및 R5은 각각 독립적으로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
R6 내지 R8 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
a, b, c 및 e는 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 동일하거나 상이할 수 있고;
d은 1 내지 3의 정수이며, 2 이상의 정수인 경우 동일하거나 상이할 수 있고;
상기 헤테로시클로알킬, 헤테로아릴렌 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]A compound for an organic electronic material represented by the following formula (1).
[Formula 1]
[In the above formula (1)
L 1 and L 2 are each independently a single bond, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) Cycloalkylene;
X 1 is CH or N;
Y 1 and Y 2 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ;
R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxyl, or each of R 4 and R 5 independently or without adjacent substituents and fused rings It may be linked to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, the alicyclic ring formed above And the carbon atoms of the monocyclic or polycyclic aromatic rings are at least one hete selected from nitrogen, oxygen and sulfur. May be substituted with a raw atom;
R 6 to R 8 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c and e are each independently an integer of 1 to 4, and may be the same or different when two or more integers;
d is an integer of 1 to 3, and may be the same or different when it is an integer of 2 or more;
Wherein said heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
상기 L1, L2, R1 내지 R8 및 R11 내지 R17에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록실로 이루어진 군으로부터 선택되는 하나 이상인 것인 유기 전자재료용 화합물.The method of claim 1,
Substituents further substituted with L 1 , L 2 , R 1 to R 8 and R 11 to R 17 are deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted with halogen, (C6-C30 ) Aryl, (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) Cycloalkyl, 5- to 7-membered heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30 ) Alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) Arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) One or more organic electrons selected from the group consisting of arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl Compound for materials.
상기 L1 및 L2은 각각 독립적으로 단일결합, (C2-C30)헤테로아릴렌, (C6-C30)아릴렌, 또는 (C3-C30)시클로알킬렌이고; X1은 CH 또는 N이며; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며; R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, N-카바졸릴, -NR11R12 또는 -SiR13R14R15이거나, 상기 R4 및 R5은 각각 독립적으로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R6 내지 R8는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; R11 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; 상기 L1 및 L2의 아릴렌, 헤테로아릴렌 및 시클로알킬렌, R1 내지 R8 및 R11 내지 R15의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것인 유기 전자재료용 화합물.The method of claim 1,
L 1 and L 2 are each independently a single bond, (C2-C30) heteroarylene, (C6-C30) arylene, or (C3-C30) cycloalkylene; X 1 is CH or N; Y 1 and Y 2 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ; R 1 to R 5 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, N-carbazolyl, -NR 11 R 12 or -SiR 13 R 14 R 15 , wherein R 4 and R 5 are each independently linked to a (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without an adjacent substituent and a fused ring to form an alicyclic ring and May form a monocyclic or polycyclic aromatic ring, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R 6 to R 8 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; R 11 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; The arylene, heteroarylene and cycloalkylene of L 1 and L 2 , the alkyl, aryl and heteroaryl of R 1 to R 8 and R 11 to R 15 are each deuterium, halogen, (C 1 -C 30) alkyl, halogen Substituted (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkyl (C6-C30) aryl, (C2-C30) heteroaryl, (C6-C30) aryl substituted (C2- C30) Heteroaryl, (C3-C30) cycloalkyl and (C6-C30) Ar (C1-C30) Alkyl compound that can be further substituted with one or more substituents selected from the group consisting of.
상기
remind
하기 화합물로부터 선택되는 유기 전자재료용 화합물.
A compound for organic electronic materials selected from the following compounds.
상기 유기 전계 발광 소자가 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 이 유기물층이 상기 유기 전자재료용 화합물 중 하나 이상과 하기 화학식 2로 표시되는 인광 도판트 중 하나 이상을 포함하는 것인 유기 전계 발광 소자:
[화학식 2]
M 1 L 101 L 102 L 103
상기 화학식 2에서,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C2-C30)헤테로아릴 또는 할로겐이고;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는
The organic electroluminescent device comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one of the compounds for organic electronic materials and at least one phosphorescent dopant represented by Formula 2 below. Organic electroluminescent element:
(2)
M 1 L 101 L 102 L 103
In Formula 2,
Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl or halogen;
R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is
상기 인광 도판트는 하기 화합물로부터 선택되는 것인 유기 전계 발광 소자.
The phosphorescent dopant is selected from the following compounds.
상기 유기물층이 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물(A); 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 금속을 포함하는 착체화합물(B); 또는 이들의 혼합물을 포함하는 것인 유기 전계 발광 소자.8. The method of claim 7,
At least one amine compound (A) wherein the organic material layer is selected from the group consisting of an arylamine compound or a styrylarylamine compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
상기 유기물층이 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것인 유기 전계 발광 소자.8. The method of claim 7,
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.
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| TW101131739A TW201323575A (en) | 2011-09-01 | 2012-08-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| PCT/KR2012/007008 WO2013032284A1 (en) | 2011-09-01 | 2012-08-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN201280049555.4A CN103857680A (en) | 2011-09-01 | 2012-08-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2014528289A JP2014531747A (en) | 2011-09-01 | 2012-08-31 | NOVEL ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015053524A1 (en) * | 2013-10-10 | 2015-04-16 | 주식회사 두산 | Organic compound and organic electroluminescent device including same |
| WO2019203550A1 (en) * | 2018-04-17 | 2019-10-24 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device comprising same |
| US10593890B2 (en) | 2015-04-06 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN114933591A (en) * | 2018-04-27 | 2022-08-23 | 北京鼎材科技有限公司 | Pyridine derivatives and use thereof |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
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| WO2016112762A1 (en) * | 2015-01-13 | 2016-07-21 | 广州华睿光电材料有限公司 | Compound, mixture comprising the same, composition and organic electronic device |
| TWI734694B (en) | 2015-07-29 | 2021-08-01 | 德商麥克專利有限公司 | Compounds having fluorene structures |
| JP6747642B2 (en) * | 2017-03-27 | 2020-08-26 | エルジー・ケム・リミテッド | Benzocarbazole compound and organic light emitting device containing the same |
| KR102514842B1 (en) * | 2017-03-28 | 2023-03-29 | 도레이 카부시키가이샤 | Compounds, electronic devices containing them, organic thin-film light-emitting devices, display devices, and lighting devices |
| KR20200011873A (en) * | 2018-07-25 | 2020-02-04 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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| JP2006131519A (en) * | 2004-11-04 | 2006-05-25 | Idemitsu Kosan Co Ltd | Condensed ring-containing compound and organic electroluminescent element using the same |
| US8062769B2 (en) * | 2006-11-09 | 2011-11-22 | Nippon Steel Chemical Co., Ltd. | Indolocarbazole compound for use in organic electroluminescent device and organic electroluminescent device |
| KR20120038060A (en) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| KR101531904B1 (en) * | 2010-10-13 | 2015-06-29 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| KR20120052879A (en) * | 2010-11-16 | 2012-05-24 | 롬엔드하스전자재료코리아유한회사 | Novel compound for organic electronic material and organic electroluminescent device using the same |
| KR20120132962A (en) * | 2011-05-30 | 2012-12-10 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| KR20120136618A (en) * | 2011-06-09 | 2012-12-20 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015053524A1 (en) * | 2013-10-10 | 2015-04-16 | 주식회사 두산 | Organic compound and organic electroluminescent device including same |
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| WO2019203550A1 (en) * | 2018-04-17 | 2019-10-24 | 엘티소재주식회사 | Heterocyclic compound and organic light-emitting device comprising same |
| KR20190120985A (en) * | 2018-04-17 | 2019-10-25 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN114933591A (en) * | 2018-04-27 | 2022-08-23 | 北京鼎材科技有限公司 | Pyridine derivatives and use thereof |
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| JP2014531747A (en) | 2014-11-27 |
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