CN110741002B - Heterocyclic compound and organic light-emitting device comprising same - Google Patents
Heterocyclic compound and organic light-emitting device comprising same Download PDFInfo
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- CN110741002B CN110741002B CN201880039613.2A CN201880039613A CN110741002B CN 110741002 B CN110741002 B CN 110741002B CN 201880039613 A CN201880039613 A CN 201880039613A CN 110741002 B CN110741002 B CN 110741002B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 7
- 239000010410 layer Substances 0.000 claims description 118
- 239000000126 substance Substances 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 dibenzofuranyl Chemical group 0.000 claims description 43
- 239000012044 organic layer Substances 0.000 claims description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 60
- 238000003786 synthesis reaction Methods 0.000 description 59
- 238000000034 method Methods 0.000 description 39
- 238000004519 manufacturing process Methods 0.000 description 36
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 230000032258 transport Effects 0.000 description 20
- 239000000463 material Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 229940125904 compound 1 Drugs 0.000 description 12
- UOQCHAHZQHMEBE-UHFFFAOYSA-N 4-(4-chlorophenyl)-6-phenyl-2-(3-phenylphenyl)pyrimidine Chemical compound Clc1ccc(cc1)-c1cc(nc(n1)-c1cccc(c1)-c1ccccc1)-c1ccccc1 UOQCHAHZQHMEBE-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
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- 229910052751 metal Inorganic materials 0.000 description 7
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- 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 7
- 238000007740 vapor deposition Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 4
- 208000027386 essential tremor 1 Diseases 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 3
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PIWNKSHCLTZKSZ-UHFFFAOYSA-N 8-bromoquinoline Chemical compound C1=CN=C2C(Br)=CC=CC2=C1 PIWNKSHCLTZKSZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 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
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 239000004332 silver Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 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
- 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
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-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
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-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
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- FEHWLBQCZZOZBU-UHFFFAOYSA-N 9,9-dimethylfluoren-2-ol Chemical compound C1=C(O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 FEHWLBQCZZOZBU-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio 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
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 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
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006757 chemical reactions by type Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
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- 208000027385 essential tremor 2 Diseases 0.000 description 2
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- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 208000031534 hereditary essential 2 tremor Diseases 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 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 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 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
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical group C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
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- 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
- 238000012423 maintenance Methods 0.000 description 1
- 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
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 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
- 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 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
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl 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
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 238000000926 separation method Methods 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 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
- 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
- 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 group [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
- 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
The application provides a novel heterocyclic compound and an organic light-emitting element using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2017-0135562 at 10 month 18 of 2017 and korean patent application No. 10-2018-0088201 at 7 month 27 of 2018, the entire contents of the disclosures of which are incorporated as part of the present specification.
The present application relates to a novel heterocyclic compound and an organic light-emitting element 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 element utilizing an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting element generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of 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 element, 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 re-transition to the ground state.
For the organic matter used for the organic light emitting element as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present application relates to a novel heterocyclic compound and an organic light-emitting element including the same.
Solution to the problem
The present application provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
Y 1 and Y 2 Each independently is hydrogen; substituted or unsubstituted C 1-40 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more of O, N, si and S 2-60 A heteroaryl group, which is a group,
ar is a substituted or unsubstituted C comprising one or more of O, N, si and S 2-60 Heteroaryl; phenyl substituted with cyano; triphenylsilane; or diphosphine oxide
Each L is independently a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or C comprising a heteroatom selected from any one or more of N, O, S and Si 2-60 A heteroarylene group,
R 1 to R 3 Each independently is halogen; a hydroxyl group; cyano group; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 A thioalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 Haloalkoxy groups; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 1-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted C comprising one or more of O, N, si and S 2-60 A heteroaryl group, which is a group,
m is a number from 0 to 4,
n is a number from 0 to 2,
o is a number from 0 to 3,
z is 1 to 4, but o+z is 4 or less.
In addition, the present application provides an organic light emitting element, comprising: a first electrode, a second electrode provided opposite to 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 contains a compound represented by the chemical formula 1.
Effects of the application
The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting element, and in the organic light-emitting element, improvement of efficiency, lower driving voltage, and/or improvement of life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, and light emission.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element including 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 element constituted by the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the hole adjustment layer 7, the light-emitting layer 8, the electron adjustment layer 9, the electron transport layer 10, and the cathode 4.
Detailed Description
In the following, the application will be described in more detail in order to aid understanding thereof.
The present application provides a compound represented by the above chemical formula 1.
In the present description of the application,and->Refers to a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is 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 group [ ]Alkylthio) is described; arylthio (/ -> Aryl thio xy); alkylsulfonyl [ ]Alkylsulfoxy); arylsulfonyl (+)>Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or one or more substituents selected from the heterocyclic groups containing one or more of N, O and S atoms, or a substituent bonded to 2 or more of the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl 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 the number of carbon atoms is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, 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 of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is 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 boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, 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 a straight chain or branched chain, 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 above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 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 application is not limited thereto.
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. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
The present descriptionIn the book, the fluorenyl group may be substituted, and 2 substituents may be bonded to each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present application is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero atom, 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, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, 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 the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the 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, alkylaryl group, or alkylamino group is the same as the above-mentioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the examples of alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In the present specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
On the other hand, in the above chemical formula 1, Y 1 And Y 2 May each independently be methyl or phenyl.
In the above chemical formula 1, m, n, and o may be 0.
In the above chemical formula 1, z may be 1.
The above chemical formula 1 may be any one selected from compounds represented by the following chemical formulas 1-1 to 1-8.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
In the above chemical formulas 1-1 to 1-8,
each L is independently a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or C comprising a heteroatom selected from any one or more of N, O, S and Si 2-60 A heteroarylene group,
ar may be substituted or unsubstituted C comprising one or more of O, N, si and S 2-60 Heteroaryl; phenyl substituted with cyano; triphenylsilane; or a diphosphine oxide.
Preferably, ar may each independently be any one selected from the following groups.
X 1 To X 4 Each independently is N or CR', but at least one or more of them is N,
r' is hydrogen, or substituted or unsubstituted C 1-60 Is a group comprising an alkyl group,
X 5 is a compound of N, S or O and the like,
R 4 and R is 5 Each independently is halogen; a hydroxyl group; cyano group; a nitrile group; a nitro group; an amine group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 A thioalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 Haloalkoxy groups; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 1-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted C comprising one or more of O, N, si and S 2-60 Heteroaryl groups.
Preferably, L may each independently be any one selected from the following structures.
Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following structures.
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The compound represented by the above chemical formula 1 can be produced by the following production methods as shown in the following reaction formulas 1 and 2, respectively, as an example. The above-described production method may be further embodied in a production example which will be described later.
[ reaction type 1]
[ reaction type 2]
In the above equations 1 and 2, the descriptions of L and Ar are the same as defined above.
The present application also provides an organic light-emitting element comprising the compound represented by the above chemical formula 1. As one example, the present application provides an organic light emitting element, comprising: a first electrode, a second electrode provided opposite to 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 contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting element of the present application 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 element of the present application may have a structure including a hole injection layer, a hole transport layer, a hole adjustment layer, a light-emitting layer, an electron adjustment layer, an electron transport layer, an electron injection layer, or the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include an electron transport layer, an electron adjustment layer, an electron injection layer, a hole blocking layer, or a light emitting layer, and the electron transport layer, the electron adjustment layer, the electron injection layer, the hole blocking layer, or the light emitting layer may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including a compound represented by chemical formula 1.
The organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by chemical formula 1.
The electron transport layer, the electron injection layer, or the layer in which both electron transport and electron injection are performed contains the compound represented by the chemical formula 1.
The organic layer may include a light-emitting layer and an electron-transporting layer, and the electron-transporting layer may include a compound represented by chemical formula 1.
The organic light-emitting element according to the present application may have a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. The organic light-emitting element according to the present application may have a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting element according to an embodiment of the present application is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting element including 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 contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting element constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole adjustment layer 7, a light-emitting layer 8, an electron adjustment layer 9, an electron transport layer 10, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, hole adjustment layer, light emitting layer, electron adjustment layer, and electron transport layer.
The organic light-emitting device may further include a hole blocking layer, an electron injection layer, or the like, and the compound represented by chemical formula 1 may be contained in the hole blocking layer or the electron injection layer.
The organic light emitting element according to the present application may be manufactured using materials and methods well known in the art, except that one or more of the organic layers contains the compound represented by chemical formula 1. In addition, when the organic light emitting element 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 element according to the present application may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: a PVD (Physical Vapor Deposition) method such as a sputtering method (sp utting) or an electron beam evaporation method (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, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting element may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, in the case of manufacturing an organic light-emitting device, the compound represented by the above chemical formula 1 may be used to form an organic layer not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
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 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); such as ZnO: al or SNO 2 : 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 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 injection substance is a layer that injects holes from the electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably 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), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene (perylene) -based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. 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 preferably has high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 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.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives and the like, but are not limited toHere.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,And diindenopyrene (Periflanthene), wherein at least one aryl vinyl group is substituted on a substituted or unsubstituted aryl amine, and the compound is substituted or unsubstituted with one 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 application is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron mediator is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and as the electron mediator, a substance that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer is suitable for a substance having high electron mobility. 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. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a 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, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has a film shapeExcellent in the formation ability. 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 organic light emitting element according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
The compound represented by the above chemical formula 1 may be contained in an organic solar cell or an organic transistor in addition to an organic light-emitting element.
In the following, preferred embodiments are presented to aid in understanding the application. However, the following examples are merely illustrative of the present application, and the present application is not limited thereto.
PREPARATION EXAMPLE 1-1
1) Synthesis of A1-1
After DMF (400 ml) was added to 9, 9-dimethyl-9H-fluoren-2-ol (150.7 g,716.7 mmol) and dissolved, NBS (177.98 g,716.7 mmol) was slowly added dropwise at 0℃and stirred at room temperature for 3 hours. After extraction with water and chloroform (chroform) at ordinary temperature, the white solid was recrystallized from hexane to prepare the above-mentioned compound A1-1 (165 g, yield: 80%).
MS[M+H] + ＝290.17
2) Synthesis of A1-2
A1-1 (20 g,69.16 mmol), bis (pinacolato) diboron (Bis (pinacolato) diboron) (19.3 g,76.0 mmol), potassium acetate (potassium acetate) (13.3 g,138.3 mmol) were charged to 200mL of 1, 4-diTo the alkane, dibenzylidene acetone palladium (795 mg,0.02 mol%) and tricyclohexylphosphine (775 mg,0.04 mol%) were added with stirring under reflux, and stirred under reflux for 12 hours. At the end of the reaction, the mixture was cooled to room temperature and filtered through celite. After the filtrate was concentrated under reduced pressure, chloroform was added to the residue and dissolved, and the organic layer was separated by washing with water and dried over anhydrous magnesium sulfate (Magnesium sulfate). This was distilled under reduced pressure, and ethyl acetate and ethanol were stirred to give A1-2 (19.76 g, yield 86%).
MS[M+H] + ＝337.24
3) Synthesis of A1-3
A1-2 (20 g,58.48 mmol) was put into 100ml of a 2M aqueous NaOH solution, the temperature was stabilized at 0℃and then hydrogen peroxide (3 eq) was slowly added dropwise. After completion of the reaction, 60ml of hydrogen chloride was added dropwise thereto for neutralization at 0℃and, after cooling to room temperature, the mixture was filtered and washed with water and hexane to give the above-mentioned compound A1-3 (10.76 g, yield: 80%).
MS[M+H] + ＝227.28
PREPARATION EXAMPLES 1-2
1) Synthesis of B1-1
B1-1 was synthesized by the same method as the synthesis of A1-1 except that 9, 9-diphenyl-9H-fluoren-2-ol was used instead of 9, 9-dimethyl-9H-fluoren-2-ol.
MS[M+H] + ＝414.31
2) Synthesis of B1-2
B1-2 was synthesized by the same method except that B1-1 was used instead of A1-1 in the synthesis of A1-2.
MS[M+H] + ＝460.38
3) Synthesis of B1-3
B1-3 was synthesized by the same method except that B1-2 was used instead of A1-2 in the synthesis of A1-3.
MS[M+H] + ＝351.42
Production example 2-1: synthesis of A2-1
A1-3 (20 g,88.38 mmol), 1-bromo-2, 3-difluorobenzene (17.91 g,92.80 mmol) and potassium carbonate (36.64 g,265 mmol) were added to dimethylformamide (300 ml), followed by heating and stirring for 3 hours. After completion of the reaction by cooling to room temperature, water was added, and the mixture was filtered, dissolved in chloroform and extracted, followed by column chromatography using ethyl acetate and hexane to give A2-1 (26.8 g, yield 80%).
MS[M+H] + ＝380.25
Production example 2-2: synthesis of A2-2
In the synthesis of A2-1, A2-2 was produced by the same method.
MS[M+H] + ＝380.25
Production example 2-3: synthesis of A2-3
A2-3 was produced by the same method as the synthesis of A2-1, except that 4-bromo-1, 2-difluorobenzene was used instead of 1-bromo-2, 3-difluorobenzene.
MS[M+H] + ＝380.25
Production examples 2 to 4: synthesis of A2-4
In the synthesis of A2-3, A2-4 was produced by the same method.
MS[M+H] + ＝380.25
Production examples 2 to 5: synthesis of B2-1
In the synthesis of A2-1, B2-1 was produced by the same method except that B1-3 was used instead of A1-3 and B2-1 was used instead of A2-1.
MS[M+H] + ＝504.40
Production examples 2 to 6: synthesis of B2-2
In the synthesis of B2-1, B2-2 was produced by synthesizing by the same method.
MS[M+H] + ＝504.40
Production examples 2 to 7: synthesis of B2-3
B2-3 was synthesized by the same method except that 4-bromo-1, 2-difluorobenzene was used instead of 1-bromo-2, 3-difluorobenzene in the synthesis of B2-1.
MS[M+H] + ＝504.40
Production examples 2 to 8: synthesis of B2-4
In the synthesis of B2-3, B2-4 was produced by synthesizing by the same method.
MS[M+H] + ＝504.40
Production example 3-1: synthesis of A3-1
Compound A2-1 (20 g,52.73 mmol), bis (pinacolato) diboron (Bis (pinacolato) diboron) (14.73 g,58.0 mmol), potassium acetate (potassium acetate) (10.1 g,105.4 mmol) was charged to 200mL of 1, 4-diTo the alkane, dibenzylidene acetone palladium (606 mg,0.02 mol%) and tricyclohexylphosphine (595 mg,0.04 mol%) were added with stirring under reflux, and stirred under reflux for 12 hours. At the end of the reaction, the mixture was cooled to room temperature and filtered through celite. Concentrating the filtrate under reduced pressure, and removing residueChloroform was added to the mixture and dissolved, and the organic layer was separated by washing with water and dried over anhydrous magnesium sulfate (Magnesium sulfate). This was distilled under reduced pressure, and recrystallized from ethyl acetate to yield A3-1 (19.33 g, yield 86%).
MS[M+H] + ＝427.32
Production example 3-2: synthesis of A3-2
A3-2 was synthesized by the same method except that A2-2 was used instead of A2-1 in the synthesis of A3-1.
MS[M+H] + ＝427.32
Production example 3-3: synthesis of A3-3
A3-3 was synthesized by the same method except that A2-3 was used instead of A2-1 in the synthesis of A3-1.
MS[M+H] + ＝427.32
Production examples 3 to 4: synthesis of A3-4
A3-4 was synthesized by the same method except that A2-4 was used instead of A2-1 in the synthesis of A3-1.
MS[M+H] + ＝427.32
Production examples 3 to 5: synthesis of B3-1
In the synthesis of A3-1, B3-1 was produced by the same method except that B2-1 was used instead of A2-1.
MS[M+H] + ＝551.46
Production examples 3 to 6: synthesis of B3-2
B3-2 was synthesized by the same method except that B2-2 was used instead of B2-1 in the synthesis of B3-1.
MS[M+H] + ＝551.46
Production examples 3 to 7: synthesis of B3-3
B3-3 was synthesized by the same method except that B2-3 was used instead of B2-1 in the synthesis of B3-1.
MS[M+H] + ＝551.46
Production examples 3 to 8: synthesis of B3-4
B3-4 was synthesized by the same method except that B2-4 was used instead of B2-1 in the synthesis of B3-1.
MS[M+H] + ＝551.46
Production example 4-1: synthesis of Compound 1
After the above compound A3-1 (10.0 g,23.45 mmol) and 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine (9.92 g,23.69 mmol) were completely dissolved in tetrahydrofuran (300 ml), a 2M aqueous potassium carbonate solution (150 ml) was added, tetrakis (triphenylphosphine) palladium (552 mg,2 mol%) was added, and the mixture was heated and stirred for 10 hours. After the reaction was completed by lowering the temperature to room temperature, the aqueous potassium carbonate solution was removed to conduct layer separation. After the solvent was removed, the white solid was recrystallized from tetrahydrofuran and ethyl acetate to give the above compound 1 (12.48 g, yield 78%).
MS[M+H] + ＝683.82
Production example 4-2: synthesis of Compound 2
Compound 2 was synthesized by the same method except that A3-2 was used instead of A3-1 and 2-chloro-4- (9, 9-dimethyl-9H-2-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine in the synthesis of compound 1.
MS[M+H] + ＝648.78
Production example 4-3: synthesis of Compound 3
In the synthesis of the above-mentioned compound 1, compound 3 was synthesized by the same method except that A3-2 was used instead of A3-1 and 2-chloro-4- (4- (dibenzo [ b, d ] furan-4-yl) phenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine.
MS[M+H] + ＝698.79
Production examples 4 to 4: synthesis of Compound 4
Compound 4 was synthesized by the same method except that A3-3 was used instead of A3-1 and 2-bromo-1, 10-phenanthroline was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine in the synthesis of compound 1.
MS[M+H] + ＝479.55
Production examples 4 to 5: synthesis of Compound 5
1) Synthesis of A4-1
In the synthesis of the above-mentioned compound 1, A4-1 was synthesized by the same method except that A3-4 was used instead of A3-1 and 2-chloro-4- (4-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine.
MS[M+H] + ＝567.06
2) Synthesis of Compound 5
A4-1 (15 g,26.4 mmol) and 9H-carbazole (15 g,27.3 mmol), sodium t-butoxide (4.56 g,59.2 mol) were added to xylene, heated and stirred, refluxed, and bis [ (tri-t-butylphosphine) ] palladium (279 mg,2 mol%) was added. After completion of the reaction by lowering the temperature to room temperature, compound 5 (15.08 g, 82%) was produced by recrystallization from tetrahydrofuran and ethyl acetate.
MS[M+H] + ＝697.81
Production examples 4 to 6: synthesis of Compound 6
Compound 6 was synthesized by the same method except that B3-1 was used instead of A3-1 and 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine was replaced with 2- (3-bromophenyl) -1-1H-benzo [ d ] imidazole in the synthesis of compound 1.
MS[M+H] + ＝693.82
Production examples 4 to 7: synthesis of Compound 7
Compound 7 was synthesized by the same method except that B3-1 was used instead of A3-1 and 2- ([ 1,1 '-biphenyl ] -4-yl) -4-chloro-6-phenylpyrimidine was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine in the synthesis of compound 1.
MS[M+H] + ＝730.87
Production examples 4 to 8: synthesis of Compound 8
1) Synthesis of B4-1
In the synthesis of the above-mentioned compound 1, B4-1 was synthesized by the same method except that B3-2 was used instead of A3-1 and 2-chloro-4- (3-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine.
MS[M+H] + ＝767.30
2) Synthesis of Compound 8
Compound 8 was synthesized by the same method except that B4-1 was used instead of A3-1 and (3-cyanophenyl) boric acid was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine in the synthesis of compound 1.
MS[M+H] + ＝833.96
Production examples 4 to 9: synthesis of Compound 9
Compound 9 was synthesized by the same method except that B3-3 was used instead of A3-1 and 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine was used instead of 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝732.86
Production examples 4 to 10: synthesis of Compound 10
Compound 10 was synthesized by the same method except that B3-4 was used instead of A3-1 and 8-bromoquinoline was used instead of 2- ([ 1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine in the synthesis of compound 1.
MS[M+H] + ＝552.65
Production examples 4 to 11: synthesis of Compound 11
Compound 11 was synthesized by the same method except that 3- (3-chlorophenyl) -6- (naphthalen-1-yl) pyrimidine was used instead of 8-bromoquinoline in the synthesis of compound 10.
MS[M+H] + ＝705.83
Production examples 4 to 12: synthesis of Compound 12
Compound 12 was synthesized by the same method as the synthesis of compound 10 above, except that 2- (4-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine was used instead of 8-bromoquinoline.
MS[M+H] + ＝732.86
Example 1
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was distilled water filtered twice using a Filter (Filter) manufactured by millbore co., ltd. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, HAT (hexanitrile hexaazabenzophenanthrene, hexan itrile hexaazatriphenylene) was applied toAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer HT1 +_ as hole transporting substance>After vacuum deposition to form a hole transport layer, HT2 is then deposited on the hole transport layer to a film thickness +.>Vacuum deposition is performed to form a hole adjusting layer. On the hole-regulating layer, a host H1 and a dopant D1 compound (25:1) are added +.>And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Next, on the light-emitting layer, an ETM1 compound is added at +.>After forming an electronic control layer by vacuum vapor deposition, compound 1 and LiQ (1:1) synthesized in production example 4-1 were added +.>Is carried out according to the thickness of (2)Vacuum vapor deposition is sequentially performed to form an electron transport layer. On the electron transport layer, lithium fluoride (LiF) is added in sequence +.>Mg and Ag (10:1) are added +.>Is vapor-deposited at the thickness of (2) and then vapor-deposited->Aluminum is formed in a thickness to form a cathode, thereby manufacturing an organic light emitting element.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance>Vapor deposition rate per sec, aluminum is maintained at 3 to +.>Vapor deposition rate per sec.
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Examples 2 to 16
An organic light-emitting device was manufactured by the same method as in example 1 above except that the compound 1 and LIQ (1:1) were used as the electron transport layer at a specific ratio in place of the compound and LIQ described in table 1 below.
Example 17
An organic light-emitting element was manufactured in the same manner as in example 1 above except that compound 1 was used in place of ETM1 as the electron-regulating layer and ETM2 was used in place of compound 1 as the electron-transporting layer.
Examples 18 to 23
In example 17 above, an organic light-emitting device was manufactured by the same method except that the compound described in table 2 below was used as the electron-regulating layer instead of the compound 1, and ETM2 and LIQ were used in the electron-transporting layer at a specific ratio described in table 2 below.
Examples 24 to 32
In example 1, experiments were performed in the same manner as the electron mediator except that the compounds shown in table 3 below were used as electron mediator instead of ETM1 and the compounds shown in table 3 below were used in a specific ratio instead of compound 1 and LIQ (1:1) as electron mediator.
Comparative examples 1 to 11
In example 1, experiments were performed in the same manner as the electron mediator except that the compounds shown in table 3 below were used as electron mediator instead of ETM1 and the compounds shown in table 3 below were used in a specific ratio instead of compound 1 and LIQ (1:1) as electron mediator.
The organic light-emitting elements manufactured in examples 1 to 32 and comparative examples 1 to 11 described above were subjected to current (20 mA/cm 2 ) The voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in tables 1 to 3 below, respectively.
TABLE 1
TABLE 2
TABLE 3
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From the above tables 1 to 3, it was confirmed that examples 1 to 32 exhibited excellent characteristics of low voltage, significant efficiency and life compared with comparative examples 1 to 11.
[ symbolic description ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: hole adjusting layer 8: light-emitting layer
9: electronic regulating layer 10: an electron transport layer.
Claims (4)
1. A compound represented by any one of the following chemical formulas 1-1 to 1-8: chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
Chemical formulas 1-5
Chemical formulas 1-6
Chemical formulas 1-7
Chemical formulas 1-8
In the chemical formulas 1-1 to 1-8,
ar is a pyridazinyl group which is unsubstituted or substituted by phenyl, biphenyl or naphthyl; quinolinyl unsubstituted or substituted by phenyl, biphenyl or naphthyl; quinazolinyl unsubstituted or substituted by phenyl, biphenyl or naphthyl; quinoxalinyl, unsubstituted or substituted by phenyl, biphenyl or naphthyl; benzimidazolyl unsubstituted or substituted with phenyl, biphenyl or naphthyl; phenanthroline groups unsubstituted or substituted by phenyl, biphenyl or naphthyl; unsubstituted pyridyl; or the following structure:
X 1 to X 3 Each independently is N or CR', but at least one of them is N,
r' is hydrogen, and the hydrogen is hydrogen,
R 4 and R is 5 Each independently is phenyl unsubstituted or substituted with pyridinyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; biphenyl group which is unsubstituted or substituted by nitrile group;naphthyl which is unsubstituted or substituted by phenyl; fluorenyl unsubstituted or substituted with methyl; unsubstituted phenanthryl; unsubstituted pyridyl; unsubstituted dibenzofuranyl; unsubstituted dibenzothienyl; or an unsubstituted carbazolyl group, and a polymer having a substituent,
l is a direct bond; phenylene or biphenylene.
2. A compound selected from any one of the following:
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3. an organic light emitting element, comprising: a first electrode, a second electrode provided opposite to 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 contains the compound according to claim 1 or 2.
4. The organic light-emitting element according to claim 3, wherein the organic layer containing the compound is an electron-transporting layer, an electron-adjusting layer, an electron-injecting layer, a hole-blocking layer, or a light-emitting layer.
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| KR10-2018-0088201 | 2018-07-27 | ||
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| CN105121594A (en) * | 2012-09-28 | 2015-12-02 | 第一毛织株式会社 | Compound for organic optoelectronic device, organic light-emitting device containing same, and display device including said organic light-emitting device |
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| CN105121594A (en) * | 2012-09-28 | 2015-12-02 | 第一毛织株式会社 | Compound for organic optoelectronic device, organic light-emitting device containing same, and display device including said organic light-emitting device |
| CN106458961A (en) * | 2014-04-09 | 2017-02-22 | 株式会社斗山 | Organic compound and organic electroluminescent element comprising same |
| KR20160010706A (en) * | 2014-07-17 | 2016-01-28 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light-emitting device including the same |
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