KR20160132344A - Novel compound and organic electroluminescent device comprising same - Google Patents
Novel compound and organic electroluminescent device comprising same Download PDFInfo
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- KR20160132344A KR20160132344A KR1020160055448A KR20160055448A KR20160132344A KR 20160132344 A KR20160132344 A KR 20160132344A KR 1020160055448 A KR1020160055448 A KR 1020160055448A KR 20160055448 A KR20160055448 A KR 20160055448A KR 20160132344 A KR20160132344 A KR 20160132344A
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- South Korea
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- substituted
- unsubstituted
- alkyl
- halogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 67
- 125000003277 amino group Chemical group 0.000 claims description 64
- 125000002560 nitrile group Chemical group 0.000 claims description 64
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 34
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 23
- 229910000077 silane Inorganic materials 0.000 claims description 23
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 239000011368 organic material Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000002825 nitriles Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 11
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 7
- 238000001953 recrystallisation Methods 0.000 abstract description 7
- 230000000903 blocking effect Effects 0.000 abstract description 5
- 230000009477 glass transition Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 89
- 239000000463 material Substances 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 20
- 239000007858 starting material Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- -1 phthalocyanine compound Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RIPZSADLUWTEFQ-UHFFFAOYSA-N 4-(4-bromophenyl)dibenzofuran Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=C1OC1=CC=CC=C21 RIPZSADLUWTEFQ-UHFFFAOYSA-N 0.000 description 4
- FIAXBPCUAUSGJH-UHFFFAOYSA-N 4-(4-bromophenyl)dibenzothiophene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=C1SC1=CC=CC=C21 FIAXBPCUAUSGJH-UHFFFAOYSA-N 0.000 description 4
- VKVHTZNHLOGHGP-UHFFFAOYSA-N 4-bromo-n-(4-bromophenyl)aniline Chemical compound C1=CC(Br)=CC=C1NC1=CC=C(Br)C=C1 VKVHTZNHLOGHGP-UHFFFAOYSA-N 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- 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 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- DFUGYZQSDFQVPU-UHFFFAOYSA-N 1-benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=COC2=C1 DFUGYZQSDFQVPU-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
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- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
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- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
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- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
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- 150000001716 carbazoles Chemical class 0.000 description 1
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- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 229910052737 gold Inorganic materials 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 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 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기발광소자에 관한 것으로, 특히 깊은 HOMO를 형성함과 동시에 전자차단이 용이한 높은 LUMO를 가지고, 우수한 hole mobility를 가져 유기발광소자의 발광보조층으로 사용시 롤오프현상이 억제되고, 저전압, 고효율, 장수명의 구현이 가능하며, 또한 높은 Tg로 인해 유기발광소자의 구동시 재결정화가 방지되어 안정성을 확보할 수 있는 신규한 화합물에 관한 것이다.The present invention relates to a novel compound and an organic light emitting diode comprising the same. More particularly, the present invention relates to a novel compound and an organic light emitting diode comprising the same, wherein the compound has a high LUMO that forms a deep HOMO and easily blocks electrons, The present invention relates to a novel compound capable of realizing low voltage, high efficiency and long life, and capable of securing stability by preventing recrystallization during driving of organic light emitting devices due to high Tg.
최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판 표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.
유기발광소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광 재료, 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자과 저분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있으며, 발광 재료는 발광 색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excitation state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism, Can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on the emission color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.
현재까지 이러한 유기발광소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다. Various compounds have been known as materials used in such organic light emitting devices. However, organic light emitting devices using known materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.
또한, 최근 유기발광소자에 있어서 정공수송층에서의 발광문제를 해결하기 위해서 정공수송층과 발광층 사이에 발광보조층을 구비하고 있다. 일반적으로 정공수송층에 사용되는 물질의 경우 낮은 HOMO 값을 가져야 하기 때문에 대부분 낮은 T1 값을 가지며, 이로 인해 발광층에서 생성된 exciton이 정공수송층으로 넘어가게 되어 결과적으로 발광층 내에서 charge balance가 불균형하여 정공수송층 계면에서 발광하는 문제가 발생한다. 또한 정공수송층 계면에서 발광을 하면서 색순도 저하 및 효율 감소 등이 나타나며, 수명이 짧아진다. 따라서 높은 T1 값을 가지며, 정공수송층 HOMO 에너지 level과 발광층의 HOMO 에너지 level 사이에 HOMO level를 갖는 발광보조층에 적합한 재료의 개발이 절실히 요청되고 있다.In recent years, in order to solve the light emission problem in the hole transporting layer in the organic light emitting element, a light emitting auxiliary layer is provided between the hole transporting layer and the light emitting layer. In general, the material used for the hole transport layer has a low HOMO value and therefore has a low T 1 value. As a result, the exciton generated in the light emitting layer is transferred to the hole transport layer. As a result, the charge balance in the light emitting layer is unbalanced, There arises a problem of light emission at the interface. In addition, light emission at the interface of the hole transport layer leads to lowering of color purity and reduction of efficiency, and the lifetime is shortened. Therefore, development of a material suitable for a light emitting auxiliary layer having a high T1 value and having a HOMO level between a HOMO energy level of the hole transporting layer and a HOMO energy level of the light emitting layer is urgently required.
상기와 같은 문제점을 해결하기 위해, 본 발명은 깊은 HOMO를 형성함과 동시에 전자차단이 용이한 높은 LUMO를 가지고, 우수한 hole mobility를 가져 유기발광소자의 발광보조층으로 사용시 롤오프현상이 억제되고, 저전압, 고효율, 장수명의 유기발광소자 구현이 가능하며, 또한 높은 Tg로 인해 유기발광소자의 구동시 재결정화가 방지되어 안정성을 확보할 수 있는 신규한 화합물을 제공하는 것을 목적으로 한다.In order to solve the above-mentioned problems, the present invention has a high LUMO that forms a deep HOMO and easily blocks electrons and has excellent hole mobility, so that roll-off phenomenon is suppressed when used as an emission- Which can realize high efficiency and long life organic light emitting devices, and can prevent recrystallization during operation of organic light emitting devices due to high Tg, thereby ensuring stability.
본 발명은 또한 상기 신규한 화합물을 발광보조층에 포함하여 전자차단이 용이하며, 롤오프현상이 억제되고, 저전압, 고효율, 장수명 및 높은 Tg로 인해 구동시 재결정화가 방지되어 안정성을 확보할 수 있는 유기발광소자를 제공하는 것을 목적으로 한다.The present invention also provides an organic electroluminescent device comprising the novel compound in a light emitting auxiliary layer to facilitate electron interruption, suppress roll-off phenomenon, prevent recrystallization during operation due to low voltage, high efficiency, long life and high Tg, And to provide a light emitting element.
상기 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to accomplish the above object, the present invention provides a compound represented by the following formula 1:
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
A는 하기 화학식 2이며, A is represented by the following formula (2)
B는 하기 화학식 3이며, B is the following formula 3,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, or substituted heteroaryl C 2 -30 An unsubstituted C 6 -50 aryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroaryl group,
L1, L2는 각각 독립적으로 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,L 1 and L 2 are each independently a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted with a heteroaryl group of C 2-30 or a substituted Unsubstituted C 2 -50 heteroarylene group,
ℓ 및 m은 각각 독립적으로 0 내지 3의 정수이며,l and m are each independently an integer of 0 to 3,
[화학식 2] (2)
[화학식 3](3)
상기 화학식 2 및 3에서,In the above Formulas 2 and 3,
*는 화학식 1에서 N과 연결되는 부위이며,* Is a moiety linked to N in formula (1)
X는 O 또는 S이며,X is O or S,
Y는 O 또는 S이며,Y is O or S,
L3은 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,L 3 is a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroarylene group,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 및 R13은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a C 2 -50 heteroaryl group which is unsubstituted or substituted with a silyl group, and which is optionally substituted with one or more substituents selected from the group consisting of halogen, amino, nitrile, nitro, C 1 -20 alkyl, C 1 -20 alkoxy,
화학식 3의 R6, R7, R8, R9 중 하나가 화학식 1의 L1 또는 N과 연결되며,One of R 6 , R 7 , R 8 and R 9 of formula (3) is linked to L 1 or N of formula (1)
n은 0 내지 3의 정수이다. n is an integer of 0 to 3;
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기발광소자를 제공한다.Also, the present invention provides an organic light emitting device including the compound represented by Formula 1.
본 발명의 화합물은 깊은 HOMO를 형성함과 동시에 전자차단이 용이한 높은 LUMO를 가지고, 우수한 hole mobility를 가져 유기발광소자의 발광보조층으로 사용시 롤오프현상이 억제되고, 저전압, 고효율, 장수명의 유기발광소자 구현이 가능하며, 또한 높은 Tg로 인해 유기발광소자의 구동시 재결정화가 방지되어 안정성을 확보할 수 있다.The compound of the present invention has a high LUMO that forms a deep HOMO and can easily block electrons and has excellent hole mobility, so that the roll-off phenomenon can be suppressed when used as a light-emitting auxiliary layer of an organic light emitting device, and a low voltage, high efficiency, Device can be realized, and recrystallization during operation of the organic light emitting device can be prevented due to high Tg, thereby ensuring stability.
도 1은 본 발명의 일 실시예에 따른 OLED의 단면을 개략적으로 도시한 것이다.
도면의 부호
11 : 기판
12 : 양극
13 : 정공주입층
14 : 정공수송층
15 : 발광보조층
16 : 발광층
17 : 전자수송층
18 : 전자주입층
19: 음극1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
The sign
11: substrate
12: anode
13: Hole injection layer
14: Hole transport layer
15: Light emission auxiliary layer
16:
17: Electron transport layer
18: electron injection layer
19: cathode
본 발명의 화합물은 하기 화학식 1로 표시된다.The compounds of the present invention are represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
A는 하기 화학식 2이며, A is represented by the following formula (2)
B는 하기 화학식 3이며, B is the following formula 3,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, or substituted heteroaryl C 2 -30 An unsubstituted C 6 -50 aryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroaryl group,
L1, L2는 각각 독립적으로 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,L 1 and L 2 are each independently a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted with a heteroaryl group of C 2-30 or a substituted Unsubstituted C 2 -50 heteroarylene group,
ℓ 및 m은 각각 독립적으로 0 내지 3의 정수이며,l and m are each independently an integer of 0 to 3,
[화학식 2] (2)
[화학식 3](3)
상기 화학식 2 및 3에서,In the above Formulas 2 and 3,
*는 화학식 1에서 N과 연결되는 부위이며,* Is a moiety linked to N in formula (1)
X는 O 또는 S이며,X is O or S,
Y는 O 또는 S이며,Y is O or S,
L3은 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,L 3 is a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroarylene group,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 및 R13은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a C 2 -50 heteroaryl group which is unsubstituted or substituted with a silyl group, and which is optionally substituted with one or more substituents selected from the group consisting of halogen, amino, nitrile, nitro, C 1 -20 alkyl, C 1 -20 alkoxy,
화학식 3의 R6, R7, R8, R9 중 하나가 화학식 1의 L1 또는 N과 연결되며,One of R 6 , R 7 , R 8 and R 9 of formula (3) is linked to L 1 or N of formula (1)
n은 0 내지 3의 정수이다. n is an integer of 0 to 3;
구체적으로 상기 화학식 1로 표시되는 화합물은 하기 화학식 4로 표시되는 화합물이다.Specifically, the compound represented by the formula (1) is a compound represented by the following formula (4).
[화학식 4][Chemical Formula 4]
상기 화학식 4에서 Ar, X, Y, ℓ, m 및 n은 화학식 1에서 정의한 바와 같으며, In Formula 4, Ar, X, Y, l, m and n are as defined in Formula 1,
R14 및 R15는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이다.R 14 and R 15 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a deuterium, a heteroaryl group of a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -50 C alkoxy group, which is unsubstituted or substituted with a silane of the group.
더욱 구체적으로 상기 화학식 4로 표시되는 화합물은 하기 화학식 5 또는 6으로 표시되는 화합물이다.More specifically, the compound represented by the formula (4) is a compound represented by the following formula (5) or (6).
[화학식 5][Chemical Formula 5]
[화학식 6][Chemical Formula 6]
상기 화학식 5 및 6에서 X, Y, ℓ, m 및 n은 화학식 1에서 정의한 바와 같으며, Wherein X, Y, l, m and n are as defined in Chemical Formula 1,
R14, R15, R16 및 R17은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이다.R 14 , R 15 , R 16 and R 17 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a deuterium, a heteroaryl group of a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -50 C alkoxy group, which is unsubstituted or substituted with a silane of the group.
구체적으로 본 발명에 따른 화합물은 상기 ℓ+ m + n의 합이 적어도 2 이상인 것이 좋다. 이 경우 유기발광소자에 적용시 수명 및 효율이 더욱 개선될 수 있다.Specifically, the compound according to the present invention preferably has a sum of? + M + n of at least 2 or more. In this case, the life and efficiency of the organic EL device can be further improved.
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물의 구체적인 예는 다음과 같다:In the present invention, specific examples of the compound represented by the formula (1) are as follows:
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본 발명에 따른 화학식 1의 화합물은 깊은 HOMO를 형성함과 동시에 전자차단이 용이한 높은 LUMO를 가지고, 우수한 hole mobility를 가져 유기발광소자의 발광보조층으로 사용시 롤오프현상이 억제되고, 저전압, 고효율, 장수명의 유기발광소자 구현이 가능하며, 또한 높은 Tg로 인해 유기발광소자의 구동시 재결정화가 방지되어 안정성을 확보할 수 있다. 특히 화학식 5 또는 6의 경우 수명 및 효율이 더욱 개선될 수 있다.The compound of formula (I) according to the present invention has a high LUMO that forms a deep HOMO and can easily block electrons, and has excellent hole mobility, thereby suppressing roll-off phenomenon when used as an emission- It is possible to realize a long-life organic light emitting device, and because of high Tg, recrystallization during operation of the organic light emitting device can be prevented, and stability can be secured. Particularly in the case of the formula (5) or (6), the life and efficiency can be further improved.
또한 본 발명의 화합물은 하기 반응식 1을 통하여 제조될 수 있다:The compounds of the present invention may also be prepared via the following scheme 1:
[반응식 1][Reaction Scheme 1]
상기 반응식에서 A, B, Ar, X, Y, L1, L2, L3, ℓ, m, n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 및 R13은 화학식 1 내지 3에서 정의된 바와 같다.In Reaction Scheme A, B, Ar, X, Y, L 1, L 2, L 3, ℓ, m, n, R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are as defined in formulas (1) to (3).
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 유기물층에 포함하는 유기발광소자를 제공한다. 구체적으로 상기 화학식 1로 표시되는 화합물은 발광보조층으로 유기발광소자에 포함된다.Also, the present invention provides an organic light emitting device comprising a compound represented by Formula 1 in an organic material layer. Specifically, the compound represented by Formula 1 is included in the organic light emitting device as a light emission-assisting layer.
본 발명의 유기발광소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층을 포함하는 바, 상기 유기발광소자의 제조방법의 일실시예는 다음과 같다.The organic light emitting device of the present invention includes one or more organic layers including the compound represented by Formula 1, and the method of manufacturing the organic light emitting device is as follows.
상기 유기발광소자는 제1전극(anode)와 제2전극(cathode) 사이에 정공주입층(HIL), 정공수송층(HTL), 발광보조층, 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기물층을 1 개 이상 포함할 수 있다.The organic light emitting device includes a hole injection layer (HIL), a hole transport layer (HTL), a light emission assisting layer, an emission layer (EML), an electron transport layer (ETL) Layer (EIL), and the like.
먼저, 기판(11) 상부에 제1전극용 물질을 증착시켜 제1전극(12)를 형성한다. 이때, 상기 기판(11)은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 제1전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO), 그래핀 등을 사용할 수 있다. 상기 제1전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.First, a
그 다음, 상기 제1전극(12) 상부에 정공주입층(13)을 형성할 수 있고, 구체적으로 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수 있다.A
상기 정공주입층 물질은 특별히 제한되지 않으며, 구체적으로 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민), m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.The hole injection layer material is not particularly limited, and specifically, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl ) Triphenylamine), m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4' benzene), HI-406 (N 1 , N 1 '- ( biphenyl-4,4'-diyl) bis (N 1 - (naphthalen-1-yl) -N 4, N 4 - diphenyl benzene -1 , 4-diamine) can be used as a hole injection layer material.
다음으로 상기 정공주입층(13) 상부에 정공수송층(14)을 형성할 수 있다. 구체적으로 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 정공수송층(14)을 형성할 수 있다.Next, a
또한, 상기 정공수송층 물질은 정공수송층에 사용되고 있는 통상의 공지 물질 중에서 임의로 선택하여 사용할 수 있으며, 구체적으로, 공지의 상기 정공수송층 물질은 N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD), N.N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.In addition, the hole transport layer material may be selected from among conventionally known materials used in the hole transport layer. Specifically, the known hole transport layer material may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, Diamine (TPD), N, N'-di (naphthalene-1-yl) And an amine derivative having an aromatic condensed ring such as N, N'-diphenylbenzidine (? -NPD).
또한 상기 정공수송층(14) 상부에 발광보조층(15)를 형성한다. 상기 발광보조층(15)은 발광보조층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다. 상기 발광보조층 물질은 본 발명의 화학식 1로 표시되는 화합물을 사용할 수 있으며, 공지의 발광보조층 물질을 본 발명의 화학식 1로 표시되는 물질과 혼합하여 사용할 수도 있다. Further, a light-emitting
그 후, 상기 정공수송층 또는 유기층(일 예로 발광보조층) 상부에 발광층(16)을 형성할 수 있다. 구체적으로 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다. Thereafter, the
또한, 상기 발광층 재료는 공지의 형광 또는 인광의 호스트 또는 도펀트를 사용할 수 있다.The light emitting layer material may be a well-known fluorescent or phosphorescent host or dopant.
이때, 형광 도펀트로는 이데미츠사(Idemitsu사)에서 구입 가능한 IDE102 또는 IDE105, 또는 BD142(N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도펀트 Ir(ppy)3(트리스(2-페닐피리딘) 이리듐), 청색 인광 도펀트인 F2Irpic(이리듐(Ⅲ 비스[4,6-다이플루오로페닐)-피리디나토-N,C2'] 피콜린산염), UDC사의 적색 인광 도펀트 RD61 등이 공동 진공증착(도핑)될 수 있다. 도펀트의 도핑농도는 특별히 제한되지 않는다.At this time, the fluorescent dopant to the possible purchase from Idemitsu Co. (Idemitsu Corporation) IDE102 or IDE105, or BD142 (N 6, N 12-bis (3,4-dimethylphenyl) -N 6, N 12 - D-mesityl chrysene - 6,12-diamine), phosphorescent dopants such as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopants such as F2Irpic Fluorophenyl) -pyridinate-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61, etc. may be vacuum vacuum deposited (doped). The doping concentration of the dopant is not particularly limited.
또한, 발광층(16)에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층(17)으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시키는 것이 좋다. 이때 사용할 수 있는 정공억제물질은 특별히 제한되지는 않으나, 정공억제재료로 사용되고 있는 공지의 것에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP(바쏘쿠프로인)) 등을 사용할 수 있다.When the phosphorescent dopant is used together with the phosphorescent dopant in the
상기와 같이 형성된 발광층(16) 상부에는 전자수송층(17)이 형성되는데, 이때 상기 전자수송층(17)은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 구체적으로 진공증착법에 의해 형성될 수 있다.The
상기 전자수송층 재료는 전자주입전극으로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 그 종류가 특별히 제한되지는 않으며, 예를 들어 퀴놀린 유도체, 특히 트리스(8-퀴놀리놀라토)알루미늄(Alq3), 또는 ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)을 사용할 수 있다. 또한, 전자수송층(17) 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(18)이 적층될 수 있으며, 전자주입층 물질로는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.The electron transport layer material serves to stably transport electrons injected from the electron injection electrode. The material is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), Or ET4 (6,6 '- (3,4-dimemethyl-1,1-dimethyl-1H-silanol-2,5-diyl) di-2,2'-bipyridine). In addition, and
또한 전자주입층(18) 상부에 제2전극 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 제2전극(19)을 형성한다. 여기서 제2전극 형성용 금속으로는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag), 금(Au), 은(Ag) 등이 있다. 또한, 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.The
본 발명의 유기발광소자는 제1전극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층, 전자주입층, 제2전극 구조의 유기발광소자뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention can be applied not only to organic light emitting devices having a first electrode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, And it is also possible to form one or two intermediate layers as necessary.
상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 구체적으로 5 내지 1,000 ㎚일 수 있다.As described above, the thickness of each organic material layer formed according to the present invention can be adjusted depending on the required degree, and may be specifically from 5 to 1,000 nm.
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.
본 발명의 유기발광소자는 높은 LUMO를 가지는 상기 화학식 1로 표시되는 화합물을 포함하여 전자차단이 용이하며, 롤오프현상이 억제되고, 저전압, 고효율, 장수명 및 높은 Tg로 인해 구동시 재결정화가 방지되어 안정성을 확보할 수 있다.The organic electroluminescent device of the present invention includes a compound represented by the above formula 1 having a high LUMO, and can easily block electrons, inhibit the roll-off phenomenon, prevent recrystallization during operation due to low voltage, high efficiency, long life and high Tg, .
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
중간체 Intermediate IMIM 의 합성Synthesis of
상기 식에서 L3 및 n은 화학식 1에서 정의한 바와 같다.Wherein L 3 and n are as defined in formula (1).
목적 화합물 합성을 위해 IM의 준비는 상기 단계를 거쳐 합성하였다.Preparation of IM for synthesis of the target compound was synthesized through the above steps.
IM1IM1 의 합성Synthesis of
둥근바닥플라스크에 benzofuran-3-ylboronic acid 20.0 g(출발물질1), 1-bromo-4-iodobenzene 12.6 g(출발물질2)를 1,4-dioxan 350 ml에 녹이고 K2CO3(2M) 100 ml와 Pd(PPh3)4 2.4 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 IM1 13.1 g (수율 68%)를 얻었다.20.0 g of benzofuran-3-ylboronic acid (starting material 1) and 12.6 g of 1-bromo-4-iodobenzene (starting material 2) were dissolved in 350 ml of 1,4-dioxane in a round bottom flask and K 2 CO 3 after loading the ml and Pd (PPh 3) 4 2.4 g it was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 13.1 g (yield: 68%) of intermediate IM1.
m/z: 271.98 (100.0%), 273.98 (97.3%), 272.99 (15.3%), 274.98 (14.7%), 273.99 (1.3%), 275.99 (1.3%)m / z: 271.98 (100.0%), 273.98 (97.3%), 272.99 (15.3%), 274.98 (14.7%
상기 IM1과 같은 방법으로 출발물질1 및 출발물질2를 달리하여, 하기 IM2 내지 IM6을 합성하였다. (하기 표1 참고)IM2 to IM6 were synthesized in the same manner as in IM1 except that starting material 1 and starting material 2 were different. (See Table 1 below)
, , ,, , , , ,
중간체 OP의 합성Synthesis of intermediate OP
상기 식에서, B, L1, L2, Ar, ℓ, m은 화학식 1에서 정의한 바와 같다.Wherein B, L 1 , L 2 , Ar, l, and m are as defined in Chemical Formula (1).
목적 화합물 합성을 위해 OP의 준비는 상기 단계를 거쳐 합성하였다.Preparation of OP for synthesis of target compound was synthesized by the above step.
OP1OP1 의 합성Synthesis of
둥근바닥플라스크에 2-bromodibenzo[b,d]furan 10 g(출발물질1), [1,1'-biphenyl]-4-amine 7.5 g(출발물질2), t-BuONa 5.8 g, Pd2(dba)3 1.5 g,(t-Bu)3P 1.8ml를 톨루엔 200 ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 OP1 9.5 g (수율 70%)를 얻었다.To a round bottom flask was added 2-bromodibenzo [b, d] furan 10 g ( starting material 1), [1,1'-biphenyl] -4-amine 7.5 g ( starting material 2), t-BuONa 5.8 g , Pd 2 ( dba) 3 (1.5 g) and (t-Bu) 3 P (1.8 ml) were dissolved in 200 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 9.5 g of OP1 (yield 70%).
m/z: 335.13 (100.0%), 336.13 (26.3%), 337.14 (3.5%)m / z: 335.13 (100.0%), 336.13 (26.3%), 337.14 (3.5%)
OP7OP7 의 합성Synthesis of
둥근바닥플라스크에 bis(4-bromophenyl)amine 10.0 g(출발물질1), dibenzo[b,d]furan-4-ylboronic acid 7.2 g(출발물질2)를 1,4-dioxan 200 ml에 녹이고 K2CO3(2M) 50ml와 Pd(PPh3)4 1.1 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체OP7 10.9 g (수율 71%)를 얻었다.To a round bottom flask was added bis (4-bromophenyl) amine 10.0 g (starting material 1), dibenzo [b, d ] furan-4-ylboronic acid 7.2 g K 2 dissolved (starting material 2) in 1,4-dioxan 200 ml 50 ml of CO 3 (2M) and 1.1 g of Pd (PPh 3 ) 4 were added, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 10.9 g (71%) of intermediate OP7.
m/z: 501.17 (100.0%), 502.18 (39.3%), 503.18 (7.9%), 504.18 (1.1%)m / z: 501.17 (100.0%), 502.18 (39.3%), 503.18 (7.9%), 504.18
상기 OP1과 같은 방법으로 출발물질1 및 출발물질2를 달리하여, 하기 OP2 내지 OP6을 합성하였고, OP7과 같은 방법으로 출발물질1 및 출발물질2를 달리하여, 하기 OP8을 합성하였다.(하기 표2 참고)The following OP2 to OP6 were synthesized in the same manner as in OP1, except that starting material 1 and starting material 2 were changed, and OP8 was synthesized in the same manner as in OP7, with starting material 1 and starting material 2 being different. 2)
, , , , ,, , , , , , , , ,
화합물1의Compound 1 합성 synthesis
둥근바닥플라스크에 IM2 3.0 g, OP1 3.2 g, t-BuONa 1.2 g, Pd2(dba)3 0.3 g,(t-Bu)3P 0.4ml를 톨루엔 60 ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 화합물1 195 g (수율 67%)를 얻었다.3.0 g of IM2, 3.2 g of OP1, 1.2 g of t-BuONa, 0.3 g of Pd 2 (dba) 3 and 0.4 ml of (t-Bu) 3 P were dissolved in toluene (60 ml) and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 195 g (yield 67%) of Compound 1.
m/z: 603.22 (100.0%), 604.22 (48.0%), 605.23 (11.3%), 606.23 (1.9%)m / z: 603.22 (100.0%), 604.22 (48.0%), 605.23 (11.3%), 606.23
화합물2의Compound 2 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP2를 사용하여 화합물 2를 합성하였다. (수율65%)Compound 2 was synthesized by using OP2 instead of OP1 in the same manner as Compound 1. [ (Yield: 65%)
m/z: 603.22 (100.0%), 604.22 (48.0%), 605.23 (11.3%), 606.23 (1.9%)m / z: 603.22 (100.0%), 604.22 (48.0%), 605.23 (11.3%), 606.23
화합물3의Compound 3 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP3을 사용하여 화합물 3을 합성하였다. (수율61%)Compound 3 was synthesized by using OP3 instead of OP1 in the same manner as in Compound 1. [ (Yield: 61%)
m/z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%), 622.21 (1.7%)m / z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%
화합물4의Compound 4 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP4를 사용하여 화합물 4를 합성하였다. (수율64%)Compound 4 was synthesized by using OP4 in place of OPl in the same manner as Compound 1. [ (Yield 64%)
m/z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%), 622.21 (1.7%)m / z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%
화합물5의Compound 5 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP5를 사용하여 화합물 5를 합성하였다. (수율68%)Compound 5 was synthesized by using OP5 in place of OPl in the same manner as in Compound 1. (Yield: 68%)
m/z: 679.25 (100.0%), 680.25 (54.4%), 681.26 (15.0%), 682.26 (2.8%)m / z: 679.25 (100.0%), 680.25 (54.4%), 681.26 (15.0%), 682.26
화합물6의Compound 6 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP6를 사용하여 화합물 6을 합성하였다. (수율65%)Compound 6 was synthesized by using OP6 instead of OP1 in the same manner as in Compound 1. [ (Yield: 65%)
m/z: 695.23 (100.0%), 696.23 (55.7%), 697.23 (15.2%), 697.22 (4.5%), 698.24 (2.7%), 698.23 (2.6%)m / z: 695.23 (100.0%), 696.23 (55.7%), 697.23 (15.2%), 697.22 (4.5%), 698.24 (2.7%), 698.23
화합물7의Compound 7 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 IM1을 사용하고 OP1 대신 OP7을 사용하여 화합물 7을 합성하였다. (수율70%)Compound 7 was synthesized by using IM1 in place of IM2 and OP7 in place of OP1 in the same manner as in Compound 1. (70% yield)
m/z: 693.23 (100.0%), 694.23 (54.6%), 695.24 (14.6%), 696.24 (2.9%)m / z: 693.23 (100.0%), 694.23 (54.6%), 695.24 (14.6%), 696.24
화합물8의Compound 8 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 IM1을 사용하고 OP1 대신 OP8을 사용하여 화합물 8을 합성하였다. (수율65%)Compound 8 was synthesized by using IM1 in place of IM2 and OP8 in place of OP1 in the same manner as in Compound 1. (Yield: 65%)
m/z: 725.18 (100.0%), 726.19 (54.5%), 727.19 (15.8%), 727.18 (9.1%), 728.18 (5.0%), 728.19 (2.9%), 726.18 (2.0%), 729.19 (1.4%)m / z: 725.18 (100.0%), 726.19 (54.5%), 727.19 (15.8%), 727.18 (9.1%), 728.18 (5.0%), 728.19 (2.9% )
화합물9의Compound 9 합성 synthesis
화합물 1과 같은 방법으로 OP1 대신 OP7을 사용하여 화합물 9를 합성하였다. (수율67%)Compound 9 was synthesized by using OP7 instead of OP1 in the same manner as in Compound 1. (Yield 67%)
m/z: 769.26 (100.0%), 770.27 (61.1%), 771.27 (18.9%), 772.27 (4.0%)m / z: 769.26 (100.0%), 770.27 (61.1%), 771.27 (18.9%), 772.27
화합물10의Compound 10 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 IM3을 사용하고 OP1 대신 OP7을 사용하여 화합물 10을 합성하였다. (수율59%)Compound 10 was synthesized using IM3 in place of IM2 and OP7 in place of OP1 in the same manner as compound 1. [ (Yield: 59%)
m/z: 769.26 (100.0%), 770.27 (61.1%), 771.27 (18.9%), 772.27 (4.0%)m / z: 769.26 (100.0%), 770.27 (61.1%), 771.27 (18.9%), 772.27
화합물11의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하여 화합물 11을 합성하였다. (수율65%)
m/z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%), 622.21 (1.7%)m / z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%
화합물12의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP2를 사용하여 화합물 12를 합성하였다. (수율62%)
m/z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%), 622.21 (1.7%)m / z: 619.20 (100.0%), 620.20 (48.8%), 621.20 (11.9%), 621.19 (4.5%), 622.20 (2.4%
화합물13의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP3을 사용하여 화합물 13을 합성하였다. (수율66%)
m/z: 635.17 (100.0%), 636.18 (47.9%), 637.18 (12.0%), 637.17 (9.2%), 638.17 (4.4%), 636.17 (2.0%), 638.18 (1.9%), 639.18 (1.0%)m / z 635.17 (100.0%) 636.18 47.9% 637.18 12.0% 637.17 9.2% 638.17 4.4% 636.17 2.03 638.18 1.9% 639.18 1.0% )
화합물14의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP4를 사용하여 화합물 14를 합성하였다. (수율64%)
m/z: 635.17 (100.0%), 636.18 (47.9%), 637.18 (12.0%), 637.17 (9.2%), 638.17 (4.4%), 636.17 (2.0%), 638.18 (1.9%), 639.18 (1.0%)m / z 635.17 (100.0%) 636.18 47.9% 637.18 12.0% 637.17 9.2% 638.17 4.4% 636.17 2.03 638.18 1.9% 639.18 1.0% )
화합물15의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP5를 사용하여 화합물 15를 합성하였다. (수율60%)
m/z: 695.23 (100.0%), 696.23 (55.7%), 697.23 (15.2%), 697.22 (4.5%), 698.24 (2.7%), 698.23 (2.6%)m / z: 695.23 (100.0%), 696.23 (55.7%), 697.23 (15.2%), 697.22 (4.5%), 698.24 (2.7%), 698.23
화합물16의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP6을 사용하여 화합물 16을 합성하였다. (수율63%)
m/z: 711.21 (100.0%), 712.21 (54.5%), 713.21 (15.4%), 713.20 (9.1%), 714.20 (5.0%), 714.22 (2.5%), 712.20 (2.0%), 715.21 (1.4%)m / z: 711.21 (100.0%), 712.21 (54.5%), 713.21 (15.4%), 713.20 (9.1%), 714.20 (5.0%), 714.22 )
화합물17의
화합물 1과 같은 방법으로 IM2 대신 IM4를 사용하고 OP1 대신 OP7을 사용하여 화합물 17을 합성하였다. (수율67%)
m/z: 709.21 (100.0%), 710.21 (55.3%), 711.21 (15.4%), 711.20 (4.5%), 712.22 (2.8%), 712.21 (2.6%)m / z: 709.21 (100.0%), 710.21 (55.3%), 711.21 (15.4%), 711.20 (4.5%), 712.22 (2.8%
화합물18의
화합물 1과 같은 방법으로 IM2 대신 IM4를 사용하고 OP1 대신 OP8을 사용하여 화합물 18을 합성하였다. (수율60%)
m/z: 741.16 (100.0%), 742.17 (54.4%), 743.16 (15.1%), 743.17 (14.5%), 744.16 (7.6%), 744.17 (2.9%), 742.16 (2.8%), 745.16 (2.2%)m / z: 741.16 (100.0%), 742.17 (54.4%), 743.16 (15.1%), 743.17 (14.5%), 744.16 (7.6%), 744.17 (2.9%), 742.16 (2.8% )
화합물19의
화합물 1과 같은 방법으로 IM2 대신 IM5를 사용하고 OP1 대신 OP7을 사용하여 화합물 19을 합성하였다. (수율65%)
m/z: 785.24 (100.0%), 786.24 (61.8%), 787.25 (18.3%), 787.23 (4.5%), 788.25 (3.8%), 788.24 (3.0%), 787.24 (1.1%)m / z: 785.24 (100.0%), 786.24 (61.8%), 787.25 (18.3%), 787.23 (4.5%), 788.25 (3.8%), 788.24
화합물20의Compound 20 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 IM6을 사용하고 OP1 대신 OP7을 사용하여 화합물 20을 합성하였다. (수율58%)Compound 20 was synthesized using IM6 in place of IM2 and OP7 in place of OP1 in the same manner as compound 1. [ (Yield: 58%)
m/z: 785.24 (100.0%), 786.24 (61.8%), 787.25 (18.3%), 787.23 (4.5%), 788.25 (3.8%), 788.24 (3.0%), 787.24 (1.1%)m / z: 785.24 (100.0%), 786.24 (61.8%), 787.25 (18.3%), 787.23 (4.5%), 788.25 (3.8%), 788.24
화합물21의Compound 21 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 4-(4-bromophenyl)dibenzo[b,d]furan(CAS No. 955959-84-9)을 사용하고 OP1 대신 OP9를 사용하여 화합물 21을 합성하였다. (수율52%)Compound 21 was synthesized by using 4- (4-bromophenyl) dibenzo [b, d] furan (CAS No. 955959-84-9) instead of IM2 and using OP9 instead of OP1. (Yield: 52%)
m/z: 643.21 (100.0%), 644.22 (50.2%), 645.22 (13.1%), 646.22 (2.3%)m / z: 643.21 (100.0%), 644.22 (50.2%), 645.22 (13.1%), 646.22
화합물22의Compound 22 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 4-(4-bromophenyl)dibenzo[b,d]thiophene(CAS No. 530402-77-8)을 사용하고 OP1 대신 OP9를 사용하여 화합물 22를 합성하였다. (수율55%)Compound 22 was synthesized by using 4- (4-bromophenyl) dibenzo [b, d] thiophene (CAS No. 530402-77-8) instead of IM2 and using OP9 instead of OP1. (Yield: 55%)
m/z: 659.19 (100.0%), 660.20 (50.2%), 661.20 (12.7%), 661.19 (5.1%), 662.20 (2.3%), 662.19 (2.3%), 660.19 (1.2%)m / z: 659.19 (100.0%), 660.20 (50.2%), 661.20 (12.7%), 661.19 (5.1%), 662.20 (2.3%), 662.19
화합물23의Compound 23 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 4-(4-bromophenyl)dibenzo[b,d]furan(CAS No. 955959-84-9)을 사용하고 OP1 대신 OP10을 사용하여 화합물 23을 합성하였다. (수율52%)Compound 23 was synthesized by using 4- (4-bromophenyl) dibenzo [b, d] furan (CAS No. 955959-84-9) instead of IM2 and using OP10 instead of OP1. (Yield: 52%)
m/z: 675.17 (100.0%), 676.17 (51.8%), 677.18 (12.3%), 677.16 (9.0%), 678.17 (4.6%), 678.18 (2.3%), 677.17 (1.2%), 679.17 (1.2%)m / z: 675.17 (100.0%), 676.17 (51.8%), 677.18 (12.3%), 677.16 (9.0%), 678.17 (4.6%), 678.18 (2.3% )
화합물24의Compound 24 합성 synthesis
화합물 1과 같은 방법으로 IM2 대신 4-(4-bromophenyl)dibenzo[b,d]thiophene(CAS No. 530402-77-8)을 사용하고 OP1 대신 OP10을 사용하여 화합물 24를 합성하였다. (수율55%)Compound 24 was synthesized by using 4- (4-bromophenyl) dibenzo [b, d] thiophene (CAS No. 530402-77-8) instead of IM2 and using OP10 instead of OP1. (Yield: 55%)
m/z: 691.15 (100.0%), 692.15 (52.5%), 693.14 (13.6%), 693.15 (13.5%), 694.15 (7.1%), 694.16 (2.0%), 695.15 (1.7%)m / z: 691.15 (100.0%), 692.15 (52.5%), 693.14 (13.6%), 693.15 (13.5%), 694.15 (7.1%), 694.16
유기발광소자의 제조Manufacture of organic light emitting device
도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 제1전극(12)/정공주입층(13)/ 정공수송층(14)/발광보조층(15)/발광층(16)/전자수송층(17)/전자주입층(18)/제2전극(19) 순으로 적층되어 있다.An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device includes a
하기 실시예 및 비교예의 정공주입층(13), 정공수송층(14), 발광보조층(15), 발광층(16), 전자수송층(17)는 아래과 같은 물질을 사용하였다.The following materials were used for the
실시예Example 1 One
인듐틴옥사이드(ITO)가 1500 Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층으로 HI01 600 Å, 정공수송층으로 NPB 250 Å, 발광보조층으로 상기 화합물1 100 Å 을 제막하였다. 다음으로 상기 발광층으로 BH01:BD01 3%로 도핑하여 300 Å 제막하였다. 다음으로 전자수송층으로 ET01:Liq(1:1) 300 Å 제막한 후 LiF 10 Å, 알루미늄(Al) 1000 Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 유기발광소자를 제작하였다.The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form HIO1 600 Å as the hole injection layer, NPO 250 Å as the hole transport layer, and 100 Å of the compound 1 as the light emission assisting layer. Next, the light emitting layer was doped with 3% BH01: BD01 to form a 300 Å layer. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer, and LiF 10 Å and aluminum (Al) 1000 Å were film-formed. The device was encapsulated in a glove box to produce an organic light emitting device.
실시예Example 2 내지 2 to 실시예Example 24 24
실시예 1과 같은 방법으로 발광보조층을 각각 화합물 2 내지 24를 사용하여 제막한 유기발광소자를 제작하였다.An organic light emitting device was fabricated in the same manner as in Example 1, in which the light-emission-assisting layer was formed using Compound 2 to 24, respectively.
비교예Comparative Example 1 One
상기 실시예 1의 발광보조층 화합물을 사용하지 않고 NPB를 350 Å 로 제막한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.The device was fabricated in the same manner except that the NPB was formed at 350 ANGSTROM without using the luminescent auxiliary layer compound of Example 1.
비교예Comparative Example 2 2
상기 실시예 1의 발광보조층 화합물1 대신 Ref.1로 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.The device was fabricated in the same manner as in Ref.1 except that the luminescent auxiliary layer compound 1 of Example 1 was used.
비교예Comparative Example 3 내지 3 to 비교예Comparative Example 6 6
상기 실시예 1의 발광보조층 화합물1 대신 각각 Ref.2 부터 Ref.5까지 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.A device was fabricated in the same manner except that Ref.2 to Ref.5 were used instead of the luminescent auxiliary layer compound 1 of Example 1, respectively.
유기발광소자의 성능평가Evaluation of performance of organic light emitting device
키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 3에 나타내었다.A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). , The performance of the organic light emitting device of Examples and Comparative Examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 3.
(hr)LT95
(hr)
상기 표 3에 나타나는 바와 같이 본 발명의 화합물은 발광보조층으로 사용시 비교예 1 내지 6에 비하여 모든 면에서 물성이 우수함을 확인할 수 있다. 특히 비교예 2 내지 6과 비교하여 같은 벤조퓨란 및 벤조싸이오펜 모이어티를 가지고 있더라도 본 발명의 화학식 1과 같은 구조를 가지는 실시예 1 내지 24의 경우 깊은 HOMO를 형성하며, 동시에 박막 상태에서 분자배열이 우수하고 홀 모빌리티가 뛰어나 효율 및 수명 향상에 큰 영향을 주었음을 알 수 있다.As shown in Table 3, the compound of the present invention is excellent in physical properties in all respects as compared with Comparative Examples 1 to 6 when used as a luminescent auxiliary layer. In particular, in comparison with Comparative Examples 2 to 6, even though they have the same benzofuran and benzothiophene moieties, Deep HOMO is formed in Examples 1 to 24 having the structure of Formula 1 of the present invention, and at the same time, And excellent hall mobility, which is a significant influence on efficiency and lifetime improvement.
Claims (8)
[화학식 1]
상기 화학식 1에서,
A는 하기 화학식 2이며,
B는 하기 화학식 3이며,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,
L1, L2는 각각 독립적으로 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,
ℓ 및 m은 각각 독립적으로 0 내지 3의 정수이며,
[화학식 2]
[화학식 3]
상기 화학식 2 및 3에서,
*는 화학식 1에서 N과 연결되는 부위이며,
X는 O 또는 S이며,
Y는 O 또는 S이며,
L3은 직접결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴렌기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기, C6 -30의 아릴기, C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴렌기이며,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 및 R13은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,
화학식 3의 R6, R7, R8, R9 중 하나가 화학식 1의 L1 또는 N과 연결되며,
n은 0 내지 3의 정수이다. A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
A is represented by the following formula (2)
B is the following formula 3,
Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, or substituted heteroaryl C 2 -30 An unsubstituted C 6 -50 aryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroaryl group,
L 1 and L 2 are each independently a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted with a heteroaryl group of C 2-30 or a substituted Unsubstituted C 2 -50 heteroarylene group,
l and m are each independently an integer of 0 to 3,
(2)
(3)
In the above Formulas 2 and 3,
* Is a moiety linked to N in formula (1)
X is O or S,
Y is O or S,
L 3 is a direct bond; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group, a silane group of the alkyl group of C 1 -20, C 1 -20, aryl group of C 6 -30, substituted heteroaryl, or optionally substituted C 2 -30 An unsubstituted C 6 -50 arylene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of C 1 -20, C 1 -20, a silane group, an aryl group of C 6 -30, substituted heteroaryl or substituted C 2 -30 Unsubstituted C 2 -50 heteroarylene group,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a C 2 -50 heteroaryl group which is unsubstituted or substituted with a silyl group, and which is optionally substituted with one or more substituents selected from the group consisting of halogen, amino, nitrile, nitro, C 1 -20 alkyl, C 1 -20 alkoxy,
One of R 6 , R 7 , R 8 and R 9 of formula (3) is linked to L 1 or N of formula (1)
n is an integer of 0 to 3;
상기 화학식 1은 하기 화학식 4로 표시되는 화합물:
[화학식 4]
상기 화학식 4에서 Ar, X, Y, ℓ, m 및 n은 화학식 1에서 정의한 바와 같으며,
R14 및 R15는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이다.The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 4:
[Chemical Formula 4]
In Formula 4, Ar, X, Y, l, m and n are as defined in Formula 1,
R 14 and R 15 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a heteroaryl group in the alkyl group, C 1 -20 C 2-50 alkoxy group, a substituted or unsubstituted silane group of C 1 -20.
상기 화학식 4는 하기 화학식 5 또는 6으로 표시되는 화합물:
[화학식 5]
[화학식 6]
상기 화학식 5 및 6에서 X, Y, ℓ, m 및 n은 화학식 1에서 정의한 바와 같으며,
R14, R15, R16 및 R17은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -20의 알킬기, C1 -20의 알콕시기, 실란기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이다.3. The method of claim 2,
Wherein the formula 4 is a compound represented by the following formula 5 or 6:
[Chemical Formula 5]
[Chemical Formula 6]
Wherein X, Y, l, m and n are as defined in Chemical Formula 1,
R 14 , R 15 , R 16 and R 17 are each independently hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, a substituted or unsubstituted silane group of the alkenyl group; Deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 2 -30 C alkoxy group, which is unsubstituted or substituted with a silane of the alkynyl group; An alkoxy group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -20 alkyl, C 1 -20 -30 1 C alkoxy group, a substituted or unsubstituted group of the silane; A C 6 -C 30 aryloxy group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; A C 6 -50 aryl group which is unsubstituted or substituted with a silyl group, a halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a heteroaryl group in the alkyl group, C 1 -20 C 2-50 alkoxy group, a substituted or unsubstituted silane group of C 1 -20.
상기 ℓ+ m + n의 합이 적어도 2 이상인 화합물.The method of claim 3,
Wherein the sum of l + m + n is at least 2.
상기 화학식 1은 하기 화학식들 중 어느 하나로 표시되는 화합물:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , ,, , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , ,, , , , ,, , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , ,, , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , The method according to claim 1,
Wherein the formula 1 is represented by any one of the following formulas:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
상기 유기물층이 발광보조층인 유기발광소자.The method according to claim 6,
Wherein the organic material layer is a light emission-assisting layer.
상기 발광보조층은 정공수송층과 발광층 사이에 존재하며, 발광층과 접해 있는 유기발광소자.The method according to claim 6,
Wherein the light emitting auxiliary layer is present between the hole transporting layer and the light emitting layer and is in contact with the light emitting layer.
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KR20170031614A (en) * | 2015-09-10 | 2017-03-21 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent device comprising same |
KR20170094665A (en) * | 2016-02-11 | 2017-08-21 | 주식회사 엘지화학 | Compound and organic electroluminescent device using the sane |
WO2018139767A1 (en) * | 2017-01-26 | 2018-08-02 | 주식회사 엘지화학 | Novel amine-based compound and organic light emitting device using same |
US11261176B2 (en) | 2017-01-26 | 2022-03-01 | Lg Chem, Ltd. | Amine-based compound and organic light emitting device using the same |
US11805697B2 (en) | 2018-01-26 | 2023-10-31 | Samsung Display Co., Ltd. | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
US11871656B2 (en) | 2018-01-26 | 2024-01-09 | Samsung Display Co., Ltd. | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
WO2020166874A1 (en) * | 2019-02-15 | 2020-08-20 | 주식회사 엘지화학 | Novel compound and organic light-emitting diode using same |
KR20200099844A (en) * | 2019-02-15 | 2020-08-25 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
KR20230025838A (en) * | 2019-02-15 | 2023-02-23 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
US11849632B2 (en) | 2019-03-20 | 2023-12-19 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting device including the same |
KR20230008688A (en) * | 2019-10-31 | 2023-01-16 | 주식회사 동진쎄미켐 | New organic compound for capping layer and Organic light emitting diode comprising to the same |
CN112961131A (en) * | 2021-02-04 | 2021-06-15 | 吉林奥来德光电材料股份有限公司 | Organic compound, preparation method and application thereof |
Also Published As
Publication number | Publication date |
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TW201708209A (en) | 2017-03-01 |
KR102559622B1 (en) | 2023-08-03 |
CN107667099A (en) | 2018-02-06 |
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