CN112585125B - Compound and organic light-emitting diode comprising same - Google Patents
Compound and organic light-emitting diode comprising same Download PDFInfo
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- CN112585125B CN112585125B CN201980053292.6A CN201980053292A CN112585125B CN 112585125 B CN112585125 B CN 112585125B CN 201980053292 A CN201980053292 A CN 201980053292A CN 112585125 B CN112585125 B CN 112585125B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 103
- 239000000126 substance Substances 0.000 claims abstract description 56
- 239000010410 layer Substances 0.000 claims description 100
- -1 dimethylfluorenyl Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 239000012044 organic layer Substances 0.000 claims description 34
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 7
- 125000005580 triphenylene group Chemical group 0.000 claims description 7
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 42
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- 125000001072 heteroaryl group Chemical group 0.000 description 20
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- 125000003277 amino group Chemical group 0.000 description 7
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- 125000005264 aryl amine group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
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- 230000001629 suppression Effects 0.000 description 6
- 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 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
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- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 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 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000005649 substituted arylene group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
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- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
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- 150000003852 triazoles Chemical class 0.000 description 2
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- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 2
- 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 1
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- 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 1
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- 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 1
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 150000001638 boron Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
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- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
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- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
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Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present invention claims priority from korean patent application No. 10-2018-0146241, filed to the korean patent office on 11/23 in 2018, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
R 1 to R 8 Are each, independently of one another, hydrogen, deuterium, nitrile, halogen radicals, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
R 1 、R 2 and R is 4 Any one of which is connected with L 3 In combination with the fact that,
L 1 and L 2 Are identical or different from one another and are each independently of one another a substituted or unsubstituted arylene group,
L 3 in order to bond directly to each other,
Ar 1 and Ar is a group 2 Are identical or different from one another and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group,
m and n are the same or different from each other and each independently is an integer of 0 to 2,
when m is 2, the above L 1 The same as or different from each other,
when n is 2, the above L 2 The same as or different from each other.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 5.
Effects of the invention
The compound according to an embodiment of the present specification may be used as a material of an organic layer of an organic light emitting device, and by using the compound, an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics can be achieved in the organic light emitting device.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron suppression layer
8: light-emitting layer
9: hole blocking layer
10: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the above chemical formula 1.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or more substituents selected from deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents selected from the above exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be aryl substituted with aryl, aryl substituted with heteroaryl, heterocyclic group substituted with aryl, aryl substituted with alkyl, or the like.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, more preferably a cycloalkyl group having 3 to 20 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamine group, naphthylamino group, biphenylamino group, anthracenyl amino group, 9-methylanthracenyl amino group, diphenylamino group, xylylamino group, N-phenyltolylamino group, triphenylamino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino group, N-phenylphenanthrylamino group, N-biphenylphenanthrenylamino group, N-phenylfluorenylamino group, N-phenylterphenylamino group, N-phenanthrenylfluorenylamino group, N-biphenylfluorenylamino group and the like, but are not limited thereto.
In the present specification, the silyl group may be represented by the chemical formula-SiRaRbRc, and the above Ra, rb, and Rc may be the same as or different from each other, and each may be independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms, more specifically 10 to 20 carbon atoms. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, an "adjacent" group refers to a substituent substituted on an atom directly bonded to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamino group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group in which the above aryl group contains 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group.
In this specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, more preferably 2 to 20, and the heteroaryl group may be a single ring or a multiple ring. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3, the above L 1 、L 2 、R 1 To R 8 、Ar 1 、Ar 2 M and n are as defined in chemical formula 1 above.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted arylene groups having 6 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical to or different from each other and are each independently an unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted or unsubstituted arylene groups having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted arylene groups having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical to or different from each other and are each independently an unsubstituted arylene group having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical to or different from each other, each independentlyIs a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted arylene groups having 6 to 12 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical to or different from each other and are each independently an unsubstituted arylene group having 6 to 12 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Each of which is the same or different from the other, is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group having a valence of 2, a substituted or unsubstituted terphenyl group having a valence of 2, a substituted or unsubstituted naphthyl group having a valence of 2, a substituted or unsubstituted anthryl group having a valence of 2, a substituted or unsubstituted phenanthryl group having a valence of 2, a substituted or unsubstituted triphenylene group having a valence of 2, or a substituted or unsubstituted fluorenyl group having a valence of 2.
In one embodiment of the present specification, the L 1 And L 2 Each of which is the same or different from the other, is independently phenylene, biphenyl having 2 valences, terphenyl having 2 valences, naphthyl having 2 valences, anthryl having 2 valences, phenanthryl having 2 valences, triphenylene having 2 valences, or fluorenyl having 2 valences.
In one embodiment of the present specification, the L 1 And L 2 Are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthyl group of 2 valency, or a substituted or unsubstituted biphenyl group of 2 valency.
In one embodiment of the present specification, the L 1 And L 2 Are the same or different from each other and are each independently phenylene, naphthyl of 2 valency, or biphenyl of 2 valency.
In one embodiment of the present specification, the L 1 And L 2 Is phenylene.
In one embodiment of the present specification, the L 1 And L 2 Naphthyl of valence 2.
In one embodiment of the present specification, the L 1 And L 2 Biphenyl is 2-valent.
In one embodiment of the present specification, the L 1 And L 2 Different from each other, is phenylene, 2-valent naphthyl, or 2-valent biphenyl.
In one embodiment of the present specification, the L 1 Is phenylene.
In one embodiment of the present specification, the L 1 Naphthyl of valence 2.
In one embodiment of the present specification, the L 1 Biphenyl is 2-valent.
In one embodiment of the present specification, the L 2 Is phenylene.
In one embodiment of the present specification, the L 2 Naphthyl of valence 2.
In one embodiment of the present specification, the L 2 Biphenyl is 2-valent.
In one embodiment of the present specification, the L 3 Is a direct bond.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from one another and are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted by an alkyl group or a heteroaryl group having 3 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from each other and are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted by an alkyl group; or a heteroaryl group having a carbon number of 3 to 12 and containing N, O or S.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each independently phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from one another and are each independently substituted or unsubstituted aryl radicals having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from one another and are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted by an alkyl group.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from each other and are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from each other and are each independently an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each independently phenyl, biphenyl, naphthyl, phenanthryl, triphenylene or dimethylfluorenyl.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, heteroaryl groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, heteroaryl groups having 3 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from one another and are each independently substituted or unsubstituted and have 3 to 12 carbon atomsHeteroaryl groups.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, heteroaryl groups having 3 to 12 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from one another and are each independently substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, which contain N, O or S.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, heteroaryl groups having 3 to 12 carbon atoms, which contain N, O or S.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each independently pyridinyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each independently carbazolyl, dibenzofuranyl or dibenzothiophenyl.
In one embodiment of the present specification, ar is as described above 1 Aryl groups having 6 to 20 carbon atoms which are substituted or unsubstituted with an alkyl group; or a heteroaryl group having a carbon number of 3 to 12 and containing N, O or S.
In one embodiment of the present specification, ar is as described above 2 Aryl groups having 6 to 20 carbon atoms which are substituted or unsubstituted with an alkyl group; or a heteroaryl group having a carbon number of 3 to 12 and containing N, O or S.
In one embodiment of the present specification, ar is as described above 1 Is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl.
In one embodiment of the present specification, ar is as described above 2 Is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are the same as or different from each other, and each is independently any one of the substituents described below.
The above dotted line represents a line corresponding to L 1 、L 2 The combined parts of the two parts are arranged in a way that,
R 11 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R is 1 、R 2 And R is 4 Is not in accordance with the L 3 Bound substituent, R 5 To R 8 Each of which is the same or different from the other, is hydrogen, deuterium, a nitrile group, a halogen group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, R is 1 、R 2 And R is 4 Is not in accordance with the L 3 Bound substituent, R 5 To R 8 Are the same or different from each other and are each independently hydrogen; deuterium; a nitrile group; f, performing the process; br; cl; i, a step of I; a nitro group; a methyl group; an ethyl group; a propyl group; an isopropyl group; a butyl group; a tertiary butyl group; methoxy; an ethoxy group; butoxy; t-butoxy; silyl substituted with methyl, ethyl or tert-butyl; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; phenanthryl; an anthracene group; dibenzofuranyl; dibenzothienyl; carbazolyl or triazinyl.
In one embodiment of the present specification, R is 1 、R 2 And R is 4 Is not in accordance with the L 3 Bound substituent, R 5 To R 8 Are identical to or different from one another and are each independently hydrogen, deuterium, nitrile, F, br, cl, I, methyl, ethyl, tert-butyl or phenyl.
In one embodiment of the present specification, R is 1 、R 2 And R is 4 Is not in accordance with the L 3 Bound substituent, R 5 To R 8 Are identical to or different from each other and are each independently hydrogen, deuterium or nitrile groups.
In one embodiment of the present specification, R is 1 、R 2 And R is 4 Is not in accordance with the L 3 Bound substituent, R 5 To R 8 Is hydrogen.
In one embodiment of the present specification, R is 3 Is hydrogen.
In one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.
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In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
The organic light emitting device of the present invention includes: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers may contain the compound.
For example, the structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. The compound of the present invention is contained in an organic layer.
Fig. 2 illustrates a structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1. The compound of the present invention may be preferably contained in the hole injection layer 5, the hole transport layer 6, and the electron suppression layer 7, but is not limited thereto.
The organic light emitting device is illustrated in fig. 1 and 2, but is not limited thereto, and additional layers may be provided between the layers.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of formula 1.
In an embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the compound of chemical formula 1.
In an embodiment of the present invention, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the compound of formula 1.
In an embodiment of the present invention, the organic layer includes an electron-inhibiting layer or a hole-blocking layer, and the electron-inhibiting layer or the hole-blocking layer may include the compound of formula 1.
In an embodiment of the present invention, the organic layer includes an electron inhibiting layer, and the electron inhibiting layer may include the compound of formula 1.
For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic layer including a compound of the above chemical formula 1 are formed on the anode, and then a substance that can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), polypyrrole and polyaniline, etc., but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injecting substance is a substance that can well inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer.
The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers are formed using the above-described compounds.
The present specification also provides a method of manufacturing an organic light emitting device formed using the above compound.
Examples of the dopant material include aromatic compounds, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic compound is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well inject electrons from the cathode and transfer the electrons to the light emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, and an effect of preventing excitons generated in the light emitting layer from being orientedAnd a compound having excellent film forming ability, which migrates from the hole injection layer. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The method of manufacturing the compound of chemical formula 1 and the manufacture of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following reaction formulae, as for the kind and number of substituents, a person skilled in the art can synthesize various types of intermediates according to the appropriate selection of known starting materials. The type of reaction and the reaction conditions may utilize techniques known in the art.
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If the production formula described in the examples of the present specification and the above intermediate are appropriately combined based on common technical knowledge, all the compounds of the above chemical formula 1 described in the present specification can be produced.
Production example 1
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After complete dissolution of compound a-1 (13.92 g,28.58 mmol) and compound a1 (6.50 g,28.02 mmol) in 220mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.04 g,42.03 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.28 mmol) was added and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of ethyl acetate to give Compound 1 (10.69 g, yield: 60%).
MS[M+H] + ＝640
Production example 2
After compound B-1 (11.87 g,24.38 mmol) and compound a2 (6.50 g,23.90 mmol) were completely dissolved in 250mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.44 g,35.85 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.12 g,0.24 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of ethyl acetate to give Compound 2 (8.64 g, yield: 53%).
MS[M+H] + ＝680
Production example 3
After compound C-1 (10.79 g,22.16 mmol), and compound a3 (6.50 g,21.10 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added, and then heated and stirred for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of tetrahydrofuran to give Compound 3 (9.22 g, yield: 61%).
MS[M+H] + ＝716
Production example 4
After complete dissolution of compound a-2 (12.98 g,26.66 mmol) and compound a4 (6.50 g,25.39 mmol) in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.66 g,38.09 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.13 g,0.25 mmol) was added and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of ethyl acetate to give Compound 4 (11.07 g, yield: 61%).
MS[M+H] + ＝714
Production example 5
After compound B-2 (13.00 g,24.20 mmol) and compound a5 (6.50 g,23.05 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.32 g,34.57 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.12 g,0.23 mmol) was added, and then heated and stirred for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give Compound 5 (9.71 g, yield: 57%).
MS[M+H] + ＝740
Production example 6
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After compound C-2 (13.00 g,24.20 mmol) and compound a6 (6.50 g,23.05 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.32 g,34.57 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.12 g,0.23 mmol) was added, and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give Compound 6 (8.83 g, yield: 52%).
MS[M+H] + ＝740
PREPARATION EXAMPLE 7
After complete dissolution of compound a-3 (17.27 g,29.42 mmol), and compound a7 (6.50 g,28.02 mmol) in 220mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.04 g,42.03 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.28 mmol) was added and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 7 (11.23 g, yield: 54%).
MS[M+H] + ＝674
Production example 8
After compound B-3 (13.09 g,22.30 mmol) and compound a8 (6.50 g,21.24 mmol) were completely dissolved in 250mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.06 g,31.86 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added, and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of ethyl acetate to give Compound 8 (12.19 g, yield: 70%).
MS[M+H] + ＝814
Production example 9
After compound C-3 (18.89 g,32.18 mmol), and compound a9 (6.50 g,31.55 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.55 g,47.33 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.16 g,0.32 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 9 (13.36 g, yield: 89%).
MS[M+H] + ＝714
Production example 10
After complete dissolution of compound a-4 (11.56 g,21.53 mmol) and compound a10 (6.50 g,21.10 mmol) in 250mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added and heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 10 (7.84 g, yield: 53%).
MS[M+H] + ＝766
Production example 11
After compound B-4 (11.56 g,21.53 mmol) and compound a11 (6.50 g,21.10 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added, and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of acetone to give compound 11 (12.37 g, yield: 59%).
MS[M+H] + ＝766
Production example 12
After compound C-4 (14.47 g,26.95 mmol) and compound a12 (6.50 g,26.42 mmol) were completely dissolved in 280mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.81 g,39.63 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.26 mmol) was added, and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of acetone to give compound 12 (11.37 g, yield: 61%).
MS[M+H] + ＝704
PREPARATION EXAMPLE 13
After complete dissolution of compound a-5 (14.20 g,25.31 mmol) and compound a13 (6.50 g,24.81 mmol) in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.58 g,37.89 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,37.21 mmol) was added and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of acetone to give compound 13 (9.78 g, yield: 53%).
MS[M+H] + ＝744
PREPARATION EXAMPLE 14
After compound B-5 (15.12 g,26.95 mmol) and compound a14 (6.50 g,26.42 mmol) were completely dissolved in 250mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.81 g,39.63 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.26 mmol) was added, and then heated and stirred for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of acetone to give compound 14 (8.25 g, yield: 43%).
MS[M+H] + ＝728
Production example 15
After compound C-5 (23.84 g,42.50 mmol), and compound a15 (6.50 g,41.67 mmol) were completely dissolved in 200mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (6.01 g,62.50 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.42 mmol) was added, and then heated and stirred for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give compound 15 (15.66 g, yield: 59%).
MS[M+H] + ＝638
PREPARATION EXAMPLE 16
After compound A-5 (11.00 g,19.62 mmol) and compound a16 (6.50 g,19.23 mmol) were completely dissolved in 210mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (2.77 g,28.85 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.10 g,0.19 mmol) was added, and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of acetone to give Compound 16 (8.89 g, yield: 65%).
MS[M+H] + ＝746
Production example 17
After compound B-5 (11.55 g,20.59 mmol) and compound a17 (6.50 g,20.19 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.91 g,30.28 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.10 g,0.20 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give compound 17 (10.07 g, yield: 68%).
MS[M+H] + ＝730
PREPARATION EXAMPLE 18
After compound C-5 (12.08 g,21.53 mmol) and compound a18 (6.50 g,21.10 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added, and the mixture was heated and stirred for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 18 (8.37 g, yield: 55%).
MS[M+H] + ＝716
Production example 19
After compound A-6 (11.34 g,21.53 mmol) and compound a19 (6.50 g,21.10 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.77 g,28.85 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.10 g,0.19 mmol) was added, and then heated and stirred for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of acetone to give compound 19 (9.76 g, yield: 61%).
MS[M+H] + ＝756
Production example 20
After compound B-6 (15.06 g,28.58 mmol), and compound a20 (6.50 g,28.02 mmol) were completely dissolved in 220mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.04 g,42.03 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.28 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of acetone to give compound 20 (10.07 g, yield: 68%).
MS[M+H] + ＝730
Production example 21
After compound C-6 (11.34 g,21.53 mmol) and compound a21 (6.50 g,21.10 mmol) were completely dissolved in 220mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.11 g,0.21 mmol) was added, and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 21 (8.37 g, yield: 55%).
MS[M+H] + ＝756
Example 1-1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>The compound 1 is vacuum deposited to form an electron-inhibiting layer. Next, on the above electron suppression layer, the film thickness is +.>A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. On the above-mentioned light-emitting layer, the film thickness is +.>A compound represented by the following chemical formula HB1 was vacuum-evaporated to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form ∈ ->Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +. >Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device. />
Examples 1-2 to 1-21
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1.
Comparative examples 1-1 to 1-5
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1. The compounds of EB2 to EB6 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device using the compound of the present invention as an electron suppression layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.
In examples 1-1 to 1-21, when a substance in which an amino-branched biphenyl (phenylene substituted with phenyl) -polycyclic heteroaryl group was sequentially bonded was used as an electron-inhibiting layer, it was found that the branched biphenyl group acted to push electrons slightly toward an amine, and thus exhibited low voltage and high efficiency, and dibenzofuran had high stability to electrons and exhibited long life.
Comparative examples 1-1 did not have a branched biphenyl group and thus did not have an effect of pushing electrons to an amine group, and comparative examples 1-2 and 1-3 were aryl amines having a branched biphenyl group attached to the dibenzofuran No. 3 position, and exhibited inferior characteristics in terms of efficiency, driving voltage and stability as compared with the compound of the present invention.
Comparative examples 1-4 show the complete breakdown of the equilibrium (balance) of the device as an arylamine with 9H-pyrido [3,4-b ] indole attached.
Comparative examples 1 to 5 used compound EB6 in which a branched biphenyl group and an amine group were bonded to the para position (No. 3, 6) of carbazole N. At this time, inferior characteristics are exhibited in terms of efficiency, driving voltage and stability as compared with the compound of the present invention.
While the preferred embodiment (electron suppression layer) of the present invention has been described above, the present invention is not limited thereto, and it is also within the scope of the present invention to be modified and implemented in various forms within the scope of the claims and the detailed description of the invention.
Claims (10)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
R 1 to R 8 Are the same or different from each other and are each independently hydrogen, or deuterium,
provided that R 1 、R 2 And R is 4 Any one of which is connected with L 3 In combination with the fact that,
L 1 and L 2 Are identical or different from one another and are each independently of one another arylene radicals having 6 to 12 carbon atoms,
L 3 in order to bond directly to each other,
Ar 1 and Ar is a group 2 Are identical to or different from one another and are each independently of one another phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl,
m and n are the same or different from each other and are each independently an integer of 0 to 2,
when m is 2, the L 1 Identical or different from each other, and
when n is 2, the L 2 The same as or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
In the chemical formula 1-1 to 1-3, said L 1 、L 2 、Ar 1 、Ar 2 M and n are as defined in the chemical formula 1,
R 1 to R 8 Each independently is hydrogen.
3. The compound of claim 1, wherein L 1 And L 2 Each independently is phenylene.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Are identical or different from one another and are each independently phenyl, biphenyl, naphthyl, phenanthryl, triphenylenyl or dimethylfluorenyl.
5. The compound of claim 1, wherein the chemical formula 1 is any one selected from the following compounds:
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6. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 5.
7. The organic light-emitting device according to claim 6, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.
8. The organic light-emitting device of claim 6, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.
9. The organic light-emitting device according to claim 6, wherein the organic layer comprises an electron-suppressing layer or a hole-blocking layer, the electron-suppressing layer or the hole-blocking layer containing the compound.
10. The organic light-emitting device of claim 6, wherein the organic layer comprises a light-emitting layer comprising the compound.
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| WO2016003225A2 (en) * | 2014-07-03 | 2016-01-07 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device comprising same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| CN108112250A (en) * | 2015-06-25 | 2018-06-01 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic device using it |
| KR20180082124A (en) * | 2017-01-10 | 2018-07-18 | 에스에프씨 주식회사 | organic light-emitting diode with High efficiency |
| WO2018157981A1 (en) * | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materials for organic electronic devices |
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| DE10135513B4 (en) | 2001-07-20 | 2005-02-24 | Novaled Gmbh | Light-emitting component with organic layers |
| KR102098093B1 (en) * | 2012-12-06 | 2020-04-08 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| JP2016100364A (en) * | 2014-11-18 | 2016-05-30 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Material for organic electroluminescent element and organic electroluminescent element using the same |
| KR20180093354A (en) * | 2017-02-13 | 2018-08-22 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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| WO2016003225A2 (en) * | 2014-07-03 | 2016-01-07 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device comprising same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| CN108112250A (en) * | 2015-06-25 | 2018-06-01 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic device using it |
| KR20180082124A (en) * | 2017-01-10 | 2018-07-18 | 에스에프씨 주식회사 | organic light-emitting diode with High efficiency |
| WO2018157981A1 (en) * | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materials for organic electronic devices |
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| CN112585125A (en) | 2021-03-30 |
| KR102331459B1 (en) | 2021-11-26 |
| KR20200061304A (en) | 2020-06-02 |
| WO2020106102A1 (en) | 2020-05-28 |
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