CN110869366A - Heterocyclic compound and organic light emitting device including the same - Google Patents
Heterocyclic compound and organic light emitting device including the same Download PDFInfo
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- CN110869366A CN110869366A CN201980003521.3A CN201980003521A CN110869366A CN 110869366 A CN110869366 A CN 110869366A CN 201980003521 A CN201980003521 A CN 201980003521A CN 110869366 A CN110869366 A CN 110869366A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 6
- 239000010410 layer Substances 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 81
- 238000002347 injection Methods 0.000 claims description 53
- 239000007924 injection Substances 0.000 claims description 53
- -1 nitro, amino Chemical group 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 50
- 239000012044 organic layer Substances 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 78
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 74
- 238000000034 method Methods 0.000 description 42
- 229940125904 compound 1 Drugs 0.000 description 40
- 230000032258 transport Effects 0.000 description 40
- 229930192474 thiophene Natural products 0.000 description 38
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 34
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 31
- 239000000463 material Substances 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 19
- 239000000758 substrate Substances 0.000 description 17
- 230000005525 hole transport Effects 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 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 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
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- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 3
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 3
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- 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
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 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
- 239000011521 glass Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-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 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-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
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- 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
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- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- 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
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical compound C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 2
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 2
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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
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- 238000011161 development Methods 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-O quinolin-8-yloxidanium Chemical compound C1=C[NH+]=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-O 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 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
- 238000007650 screen-printing Methods 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
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- 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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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
Abstract
The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0010013, 26.1.2018, the entire contents of which are incorporated herein by reference.
The present invention relates to a novel heterocyclic 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 has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, 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 electroluminescent device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel heterocyclic compound and an organic light emitting device including the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
y is S, O or CR'2，
R' is each independently substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S2-60(ii) a heteroaryl group, wherein,
R1to R7Each independently is halogen, hydroxy, cyano, nitrile, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Thioalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C1-60Alkenyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S2-60(ii) a heteroaryl group, wherein,
a. e and g are each independently 0 to 4,
b. d and f are each independently 0 to 3,
c is 0 to 5.
The present invention also provides an organic light-emitting device including a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of life span characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4.
Fig. 3 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 8, an electron transport layer 9, an electron injection and transport layer 11, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the context of the present specification,
and
refers to a bond to another substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio radicals (A), (B), (C), (D), (
Alkyl thio xy); arylthio radicals (A), (B), (C
Aryl thio xy); alkylsulfonyl (
Alkyl sulfo xy); arylsulfonyl (
Aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituents formed by connecting 2 or more substituents of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the ester group, in the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. With respect to the above aryl radicals, asThe monocyclic aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like, but is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing at least 1 of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
On the other hand, in the chemical formula 1, R' is preferably a methyl group.
In the above chemical formula 1, a, b, c, d, e and f may be 0.
In the above chemical formula 1, R1To R7At least 1 of which may be cyano.
The chemical formula 1 may be any one selected from the following compounds.
In the above 1-1 to 1-16, Y may be S, O or CR'2。
The above definition of R' is the same as that mentioned previously.
Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following compounds.
The compound represented by the above chemical formula 1 can be produced by the production method of the following reaction formula 1. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 1]
In the above reaction formula 1, the description of Y is the same as that in the above chemical formula 1.
The compound represented by the above chemical formula 1 can be produced by referring to the above reaction formula 1 and appropriately replacing the starting material corresponding to the structure of the compound to be produced.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer (a layer that simultaneously performs hole injection and transport), which includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the light emitting layer includes 2 or more hosts, and 1 of the hosts includes the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer (a layer that performs electron injection and transport simultaneously), and the electron transport layer, the electron injection layer, or the electron injection and transport layer includes the compound represented by the above chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the electron transport and injection layer includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted (inverted) type organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, electron transport layer, and electron injection layer.
Fig. 3 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 8, an electron transport layer 9, an electron injection and transport layer 11, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection and transport layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods well known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, in the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO: al or SNO2: a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject 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 LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection material is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection material: the organic light-emitting device has an ability to transport holes, has a hole injection effect from an anode, has an excellent hole injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerizedstyryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are aromatic amine derivatives and styryl amine compoundsBoron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenoperene (Periflanthene), etc., and the styrylamine compound is a compound substituted with at least one arylvinyl group on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transporting material is a layer which receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and is a material which can satisfactorily receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the usual substances having a low work function and accompanied by an aluminum or 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 for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
In the following, preferred embodiments are presented to aid in the understanding of the invention. However, the following examples are only for illustrating the present invention and the present invention is not limited thereto.
[ production example ]
Production example 1: production of intermediate A1
2-chloro-4- (4-chlorophenyl) -6-phenyl-1, 3, 5-triazine (15.0g, 49.64mmol), dibenzo [ b, d ] in a 500ml round-bottomed flask under a nitrogen atmosphere]After thiophen-4-ylboronic acid (11.3g, 49.64mmol) was completely dissolved in 210ml of tetrahydrofuran, 1M potassium carbonate solution (150ml) was added, tetrakis (triphenylphosphine) palladium (1.7g, 1.49mmol) was added,the mixture was stirred with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethanol to produce the above-mentioned Compound A1(21.1g, yield: 94%) (MS [ M + H ])]+＝450)。
Production example 2: production of intermediate A2
Intermediate A1(21.1g, 46.89mmol), bis (pinacolato) diboron (13.1g, 51.58mmol), Pd (dba) in a 1L round bottom flask under nitrogen2(0.8g，1.41mmol)、PCy3(0.8g,2.81mmol) and KOAc (13.8g, 140.68mmol) were added to 300mL of bis
In an alkane, the mixture was refluxed and stirred for 2 hours. After completion of the reaction was confirmed by HPLC, the base (base) was removed by filtration, and the solution was concentrated under reduced pressure. Dissolving it in CHCl3After washing with water, the solution containing the product was concentrated under reduced pressure and recrystallized from ethanol to obtain the above-mentioned compound A2(21.1g, yield 83%) (MS [ M + H ]]+＝542)。
Production example 3: production of intermediate A3
In a 1L round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A2(21.1g, 38.97mmol) and 1-bromo-2-nitrobenzene (8.7g,42.86mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate (60ml) was added, tetrakis (triphenylphosphine) palladium (1.4g, 1.17mmol) was added, and the mixture was stirred under heating for 24 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethanol to obtain the above-mentioned Compound A3(17.4g, yield: 83%) (MS [ M + H ])]+＝537)。
Production example 4: production of intermediate A4
Triethyl phosphite (100mL, 580.3mmol) was added to compound A3(17.4g, 32.43mmol) in a 1L round bottom flask under nitrogen and stirred for 3 hours under heating. The temperature was reduced to normal temperature and filtered to give a solid which was washed with water. The obtained compound was dried to obtain Compound A4(11.3g, yield: 69%) (MS [ M + H ]]+＝505)。
[ examples ]
Example 1: production of Compound 1
In a 1L round-bottomed flask under nitrogen in compound A4(11.3g, 22.39mmol), 2-bromodibenzo [ b, d ]]After 200mL of xylene was added to thiophene (6.1g, 23.51mmol) and sodium tert-butoxide (4.3g, 44.79mmol), bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.22mmol) was added, and the mixture was stirred under heating for 1 hour. The temperature was reduced to normal temperature and filtered to give a solid which was washed with water. The obtained compound was dried to obtain Compound 1(5.7g, yield: 37%) (MS [ M + H ]]+＝687)。
Example 2: production of Compound 2
Using 4-bromodibenzo [ b, d ]]Thiophene instead of 2-bromodibenzo [ b, d ]]Except for thiophene, compound 2(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 3: production of Compound 3
Using 1-bromodibenzo [ b, d ]]Thiophene instead of 2-bromodibenzo [ b, d ]]Thiophenes, other thanIn addition, Compound 3(MS [ M + H ] was produced in the same manner as Compound 1]+＝687)。
Example 4: production of Compound 4
Using 1- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 4(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 5: production of Compound 5
Using 2-bromodibenzo [ b, d ]]Thiophene instead of 3-bromodibenzo [ b, d ]]Except for thiophene, compound 5(MS [ M + H) was produced by the same method as the method for producing compound 4]+＝687)。
Example 6: production of Compound 6
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 6(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 7: production of Compound 7
Using 3- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 7(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 8: production of Compound 8
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 8(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 9: production of Compound 9
Using 4- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 9(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 10: production of Compound 10
Using 4- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 10(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 11: production of Compound 11
Using 4- (4- (dibenzo [ b, d ]]Thiophene(s)-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromodibenzo [ b, d]Thiophene instead of Compound A4 and 2-Bromobenzo [ b, d]Except for thiophene, compound 11(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝687)。
Example 12: production of Compound 12
Using 1- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 12(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 13: production of Compound 13
Using 1- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 13(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 14: production of Compound 14
Using 2- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 14(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 15: production of Compound 15
Using 2- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 15(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 16: production of Compound 16
Using 2- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 16(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 17: production of Compound 17
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 17(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 18: preparation of Compound 18
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 18(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 19: production of Compound 19
Using 4- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 19(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 20: production of Compound 20
Using 4- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 20(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 21: production of Compound 21
Using 4- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromodibenzo [ b, d]Furan instead of compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 21(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝671)。
Example 22: preparation of Compound 22
Using 1- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Thiophene, except for the same method as the method for producing Compound 1By the method, Compound 22(MS [ M + H ] was produced]+＝697)。
Example 23: production of Compound 23
Using 1- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 23(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 24: production of Compound 24
Using 2- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 1-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 24(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 25: production of Compound 25
Using 2- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 25(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 26: preparation of Compound 26
Using 2- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromo-9, 9-bismethyl-9H-fluorene instead of Compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 26(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 27: production of Compound 27
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 27(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 28: preparation of Compound 28
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 3-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 28(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 29: production of Compound 29
Using 4- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 29(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 30: production of Compound 30
Using 4- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 4-bromo-9, 9-dimethyl-9H-fluorene instead of compound A4 and 2-bromodibenzo [ b, d]Except for thiophene, compound 30(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝697)。
Example 31: production of Compound 31
Compound 31(MS [ M + H ] was produced in the same manner as for Compound 1, except that Compound A4-1 was used in place of Compound A4]+＝712)。
Example 32: production of Compound 32
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 8-bromodibenzo [ b, d]Thiophene-2-carbonitriles instead of Compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 32(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝712)。
Example 33: production of Compound 33
Using 3- (4- (dibenzo [ b, d ]]Thien-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 6-bromodibenzo [ b, d]Thiophene-3-carbonitriles instead of Compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 33(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝712)。
Example 34: preparation of Compound 34
Compound 34(MS [ M + H ] was produced in the same manner as for the production of Compound 21, except that Compound A4-2 was used in place of Compound A4]+＝696)。
Example 35: production of Compound 35
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 7-bromodibenzo [ b, d]Furan-2-carbonitrile instead of Compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 35(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝696)。
Example 36: preparation of Compound 36
Using 3- (4- (dibenzo [ b, d ]]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 8-bromodibenzo [ b, d]Furan-2-carbonitrile instead of Compound A4 and 2-bromodibenzo [ b, d ]]Except for thiophene, compound 36(MS [ M + H) was produced by the same method as the method for producing compound 1]+＝696)。
[ Experimental example ]
Experimental example 1-1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated to a thin film thickness of (2) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (fischer Co.) and the distilled water used was distilled water filtered twice with a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the washing of distilled water is finished, adding solvents of isopropanol, acetone and methanol into the distilled waterAfter being washed by ultrasonic wave and dried, the mixture is conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HI-1 compound was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, the following HT-1 compound is added
Is formed by thermal vacuum deposition, and a hole transport layer is formed on the HT-1 deposited film by depositing a HT-2 compound
The electron blocking layer is formed by vacuum evaporation. On the HT-2 deposited film, the compound 1 produced in example 1, the YGH-1 compound and the phosphorescent dopant YGD-1 were co-deposited at a weight ratio of 44:44:12 to form a light-emitting layer
A thick light emitting layer. On the light-emitting layer, the following ET-1 compound is added
The electron transport layer was formed by vacuum evaporation, and the following ET-2 compound and Li were co-evaporated on the electron transport layer at a weight ratio of 98:2 to form an electron injection layer. On the electron injection layer, aluminum is added
The thickness is evaporated to form a cathode.
In the above processIn the process, the evaporation speed of the organic material is maintained
Aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7～5×10-8And (4) supporting.
Experimental examples 1-1 to 1-36
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compounds described in table 1 below were used instead of compound 1 of example 1.
Comparative Experimental examples 1-1 and 1-2
An organic light-emitting device was produced in the same manner as in experimental example 1-1 above, except that in experimental example 1 above, the compounds described in table 1 below were used instead of compound 1 of example 1. On the other hand, compounds of CE1 and CE2 in table 1 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting device was set at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 50mA/cm2The time (LT) required for the initial luminance to reach 95% was measured at the current density of (1)95). The results are shown in table 1 below.
[ TABLE 1]
As shown in table 1, it was confirmed that the compound of the present invention exhibits superior characteristics in efficiency and life as compared with the comparative experimental examples when used as a light-emitting layer material.
Experimental example 2-1
ITO (indium tin oxide) is added
The glass substrate (corning 7059 glass) coated to a thin film thickness of (a) was put in distilled water in which a dispersant was dissolved, and washed by ultrasonic waves. The detergent used was a product of Hill corporation, and distilled water obtained by twice filtration using a filter manufactured by Millipore corporation was used as distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared, the following HI-1 compound was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, the following HT-1 compound is added
Is formed by vacuum evaporation, and a host H1 and a dopant D1 compound are mixed in a weight ratio of 97.5:2.5 on the hole transport layer
The thickness of (2) is vacuum-evaporated to form a light-emitting layer. On the light-emitting layer, the following compound ET-A and
the electron transport layer is formed by vacuum evaporation. On the electron transport layer, compound 1 produced in example 1 and LiQ (Lithium lithonium quinate, 8-hydroxyquinolinium) were vacuum-evaporated at a weight ratio of 1:1 to obtain an electron transport layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Experimental examples 2-2 to 2-36
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compounds shown in table 2 below were used instead of compound 1 of example 1.
Comparative Experimental examples 2-1 and 2-2
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compounds shown in table 2 below were used instead of compound 1 of example 1. The compounds of CE3 and CE4 of table 2 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting device was set at 10mA/cm2The drive voltage and the luminous efficiency were measured at the current density of (2),at 50mA/cm2The time (LT) required for the initial luminance to reach 95% was measured at the current density of (1)95). The results are shown in table 1 below.
[ TABLE 2 ]
As shown in table 2, it was confirmed that the compound of the present invention exhibits excellent characteristics in efficiency and life as compared with the comparative experimental examples when used as an electron transport layer material.
[ notation ] to show
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: luminescent layer
9: electron transport layer 10: electron injection layer
11: an electron injection and transport layer.
Claims (9)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
y is S, O or CR'2，
R' is each independently substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S2-60(ii) a heteroaryl group, wherein,
R1to R7Each independently is halogenElements, hydroxy, cyano, nitrile, nitro, amino, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Thioalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkoxy, substituted or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C1-60Alkenyl, substituted or unsubstituted C6-60Aryl, substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S2-60(ii) a heteroaryl group, wherein,
a. e and g are each independently 0 to 4,
b. d and f are each independently 0 to 3,
c is 0 to 5.
2. The compound of claim 1, wherein R' is methyl.
3. The compound of claim 1, wherein a, b, c, d, e, and f are 0.
4. The compound of claim 1, wherein R1To R7At least 1 of which is cyano.
5. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one selected from the group consisting of:
the description of Y is the same as defined in claim 1.
6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
7. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6.
8. The organic light emitting device according to claim 7, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, an electron injection and transport layer, or a light emitting layer.
9. The organic light-emitting device according to claim 8, wherein the light-emitting layer contains 2 or more kinds of hosts, and 1 of the hosts is the compound.
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Citations (4)
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| CN103797602A (en) * | 2011-09-12 | 2014-05-14 | 新日铁住金化学株式会社 | Organic electroluminescent element |
| US20150171336A1 (en) * | 2013-12-13 | 2015-06-18 | Samsung Display Co., Ltd. | Triazine-based compounds and organic light-emitting devices including triazine-based compounds |
| US20150171340A1 (en) * | 2013-12-17 | 2015-06-18 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| KR20180055688A (en) * | 2016-11-17 | 2018-05-25 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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|---|---|---|---|---|
| CN103797602A (en) * | 2011-09-12 | 2014-05-14 | 新日铁住金化学株式会社 | Organic electroluminescent element |
| US20150171336A1 (en) * | 2013-12-13 | 2015-06-18 | Samsung Display Co., Ltd. | Triazine-based compounds and organic light-emitting devices including triazine-based compounds |
| US20150171340A1 (en) * | 2013-12-17 | 2015-06-18 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| KR20180055688A (en) * | 2016-11-17 | 2018-05-25 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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| CN114075182A (en) * | 2021-09-23 | 2022-02-22 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, organic electroluminescent device using nitrogen-containing compound and electronic device |
| CN114075182B (en) * | 2021-09-23 | 2023-10-31 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, organic electroluminescent device using same and electronic device |
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