CN108699070B - Heterocyclic compound and organic electroluminescent element comprising same - Google Patents
Heterocyclic compound and organic electroluminescent element comprising same Download PDFInfo
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- CN108699070B CN108699070B CN201780011570.2A CN201780011570A CN108699070B CN 108699070 B CN108699070 B CN 108699070B CN 201780011570 A CN201780011570 A CN 201780011570A CN 108699070 B CN108699070 B CN 108699070B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 36
- 239000010410 layer Substances 0.000 claims description 123
- -1 dimethylfluorenyl group Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000012044 organic layer Substances 0.000 claims description 42
- 238000002347 injection Methods 0.000 claims description 36
- 239000007924 injection Substances 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 230000005525 hole transport Effects 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000000052 comparative effect Effects 0.000 description 37
- 230000032258 transport Effects 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 23
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- 239000000463 material Substances 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 238000010992 reflux Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 14
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- 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 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
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- 239000010406 cathode material Substances 0.000 description 5
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
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- 229940125904 compound 1 Drugs 0.000 description 4
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
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- 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
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- SZLNOBJKCVERBJ-UHFFFAOYSA-N 1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2,4,6,8(19),9,11,13,15,17-nonaene Chemical class C12=CC=CC=C2N2C3=CC=CC=C3C3=CC=CC1=C32 SZLNOBJKCVERBJ-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 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
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- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
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- 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
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- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
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- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- DRNWNTAANHEQMK-UHFFFAOYSA-N 1-bromo-3-chloro-2-fluorobenzene Chemical compound FC1=C(Cl)C=CC=C1Br DRNWNTAANHEQMK-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical group C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
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- 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 group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
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- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- FHCANGSBXYETRP-UHFFFAOYSA-N [4-[4-(9,9-dimethylfluoren-2-yl)-N-triphenylen-2-ylanilino]phenyl]boronic acid Chemical compound CC1(C2=CC=CC=C2C=2C=CC(=CC1=2)C1=CC=C(C=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1)C FHCANGSBXYETRP-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
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- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000004122 cyclic 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- QKBTTXJHJNXCOQ-UHFFFAOYSA-N dibenzofuran-4-amine Chemical compound O1C2=CC=CC=C2C2=C1C(N)=CC=C2 QKBTTXJHJNXCOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000003618 dip coating Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 150000002219 fluoranthenes Chemical class 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
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 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
- 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
- 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
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YAFZRDRWOQRUIP-UHFFFAOYSA-N n-[4-(9,9-dimethylfluoren-2-yl)phenyl]-4-phenylaniline Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1C(C=C1)=CC=C1NC(C=C1)=CC=C1C1=CC=CC=C1 YAFZRDRWOQRUIP-UHFFFAOYSA-N 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 150000004866 oxadiazoles Chemical class 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
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- 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
- 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 1
- 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 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
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 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
- 230000007017 scission Effects 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 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
- 238000001771 vacuum deposition Methods 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
- 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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- 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
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- 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
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
The present specification provides a heterocyclic compound and an organic electroluminescent element including the same.
Description
Technical Field
The present specification relates to a heterocyclic compound and an organic electroluminescent element including the same.
This specification claims priority to korean patent application No. 10-2016-.
Background
An electroluminescent element is one of self-luminous display elements, and has advantages of a wide viewing angle, excellent contrast, and a high response speed.
The organic light-emitting element has a structure in which an organic thin film is disposed between 2 electrodes. When a voltage is applied to the organic light emitting element having such a structure, electrons and holes injected from the 2 electrodes are combined in the organic thin film to be quenched in pairs and simultaneously emit light. The organic thin film may be formed of a single layer or a plurality of layers as necessary.
The material of the organic thin film may have a light-emitting function as needed. For example, as the material of the organic thin film, a compound which can constitute the light-emitting layer itself alone, or a compound which can function as a host or a dopant of the host-dopant light-emitting layer may be used. In addition, as a material of the organic thin film, a compound which can exert an action such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection can be used.
In order to improve the performance, lifetime, or efficiency of organic electroluminescent elements, development of materials for organic thin films is continuously demanded.
Disclosure of Invention
The present specification provides a heterocyclic compound and an organic electroluminescent element including the same.
The present application provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above chemical formula 1, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
l1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
r1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
a and c are integers of 0 to 3, b is an integer of 0 to 4, and substituents in parentheses when a to c are 2 or more are the same or different.
Further, the present application provides an organic electroluminescent element, comprising: the organic light-emitting device includes 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 the heterocyclic compound.
The heterocyclic compound according to one embodiment of the present application is used in an organic electroluminescent element, and can reduce the driving voltage of the organic electroluminescent element, improve the light efficiency, and improve the life characteristics of the element by utilizing the thermal stability of the compound.
Drawings
Fig. 1 shows an example of an organic electroluminescent element in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked.
Fig. 2 shows an example of an organic electroluminescent element in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked.
FIG. 3 is a LC/MS spectrum of chemical formula 1A of reaction formula 1.
FIG. 4 is an LC/MS spectrum of Compound 1 of Synthesis example 1.
FIG. 5 is an LC/MS spectrum of Compound 2 of Synthesis example 2.
FIG. 6 is an LC/MS spectrum of Compound 7 of Synthesis example 7.
Description of the symbols
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides heterocyclic compounds represented by the above chemical formula 1.
Examples of the substituent in the present specification are described below, but the present invention is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
The term "substituted or unsubstituted" in the present specification means that the substituent is substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a phosphine oxide group, a silyl group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryl group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are bonded, or does not have any substituent. 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, 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 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, isohexyl group, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, specifically, 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 is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is 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. 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl 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 adjacent substituents may be bonded to each other to form a ring.
In the present specification, the heterocyclic group includes one or more heteroatoms other than carbon atoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, Si, S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include phenylthio, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,Azolyl group,Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, hydrogenated acridinyl (for example,) Pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, quinolyl, and the like,Indolyl, carbazolyl, benzoAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, benzosilacyclopentadienyl, dibenzosilacyclopentadienyl, phenanthrolinyl (phenylanthralinyl group), isoquinocylAzolyl, thiadiazolyl, phenothiazinyl, phenoxazineOxazine groups, and their fused structures, etc., but are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure containing a sulfonyl group, and examples thereof includeAnd the like.
In the present specification, the fused structure may be a structure in which an aromatic hydrocarbon ring is fused to the substituent. For example, the fused ring of benzimidazole may be And the like, but is not limited thereto.
In the present specification, arylene means a group having two binding sites in an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and in addition to these, the description of the above-mentioned aryl groups can be applied.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring are considered to be "adjacent" groups to each other.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with an aryl group, a biphenyl group substituted or unsubstituted with an aryl group, a terphenyl group substituted or unsubstituted with an aryl group, a triphenylene group substituted or unsubstituted with an aryl group, a dimethylfluorenyl group substituted or unsubstituted with an aryl group, a dibenzofuranyl group substituted or unsubstituted with an aryl group, a dibenzothiophenyl group substituted or unsubstituted with an aryl group, or a carbazolyl group substituted or unsubstituted with an aryl group.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted by a phenyl group, a biphenyl group substituted or unsubstituted by a phenyl group, a terphenyl group substituted or unsubstituted by a phenyl group, a triphenylene group substituted or unsubstituted by a phenyl group, a dimethylfluorenyl group substituted or unsubstituted by a phenyl group, a dibenzofuranyl group substituted or unsubstituted by a phenyl group, a dibenzothiophenyl group substituted or unsubstituted by a phenyl group, or a carbazolyl group substituted or unsubstituted by a phenyl group.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted by a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a dimethylfluorenyl group substituted or unsubstituted by a phenyl group, a dibenzofuranyl group substituted or unsubstituted by a phenyl group, a dibenzothiophenyl group substituted or unsubstituted by a phenyl group, or a carbazolyl group substituted or unsubstituted by a phenyl group.
In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having a valence of 2 and having 2 to 60 carbon atoms.
In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 30 carbon atoms.
In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted 2-valent dibenzofuranyl group, a substituted or unsubstituted 2-valent dibenzothiophenyl group, or a substituted or unsubstituted 2-valent fluorenyl group.
In one embodiment of the present specification, L1 is a direct bond, a phenylene group substituted or unsubstituted with an alkyl group, a 2-valent dibenzofuranyl group substituted or unsubstituted with an alkyl group, a 2-valent dibenzothiophenyl group substituted or unsubstituted with an alkyl group, or a 2-valent fluorenyl group substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, L1 is a direct bond, a phenylene group, a 2-valent dibenzofuranyl group, a 2-valent dibenzothiophenyl group, a 2-valent fluorenyl group, or a 2-valent dimethylfluorenyl group.
In one embodiment of the present specification, L2 and L3, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group.
In one embodiment of the present specification, L2 and L3, equal to or different from each other, are each independently a direct bond or an arylene group.
In one embodiment of the present specification, L2 and L3, which are the same or different from each other, are each independently a direct bond or a phenylene group.
In one embodiment of the present specification, R1 to R3 are hydrogen.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following structural formulae.
The compound according to one embodiment of the present specification can be produced by a production method described later.
[ reaction formula 1]
1) Production of chemical formula 1-a
100.00g (1.0eq) of 9H-carbazole and 100.74g (1.5eq) of KOtBu were added to 1L of DMF (Dimethylformamide) and stirred with heating. 149.33g (1.2eq) of 1-bromo-3-chloro-2-fluorobenzene were added at the beginning of reflux. After 5 hours the reaction was complete, the reaction was poured into water, the crystals were allowed to fall and filtered. The filtered solid was completely dissolved in CHCl3Then, the mixture was washed with water, and the solvent was removed under reduced pressure again, followed by purification by column chromatography. 191.22g of formula 1-a were obtained (yield 90%). [ M +2H ]]=356
2) Production of chemical formula 1A
191.22g (1.0eq) of Pd (t-Bu) of the formula 1-a, 1.19g (0.005eq) of Pd (t-Bu)3P)2129.74g (2.00eq) of K2CO3Added to 1L of Dimethylacetamide (Dimethylacetamide) and stirred under reflux. After 3 hours the reaction was poured into water and the crystals were filtered off. The filtered solid was completely dissolved in ethyl acetate, washed with water, and the solution containing the product was concentrated under reduced pressure and purified by column chromatography. 107.15g of chemical formula 1A (yield 83%) were obtained. [ M ] A]=275
In addition, the present specification provides an organic electroluminescent element including the above compound.
In one embodiment, there is provided an organic electroluminescent element including: the organic light-emitting device includes 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 the heterocyclic compound.
In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
The organic layer of the organic electroluminescent element of the present application may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, as a representative example of the organic electroluminescent element of the present invention, the organic electroluminescent element 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 electroluminescent element is not limited to this, and a smaller number of organic layers may be included.
In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.
In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
In one embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.
In one embodiment of the present application, the organic electroluminescent element includes: a first electrode, a second electrode provided so as to face the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the 2 or more organic layers contains the heterocyclic compound.
In one embodiment of the present application, 2 or more types of the electron transport layer, the electron injection layer, the layer that simultaneously transports electrons and injects electrons, and the hole blocking layer may be selected as the 2 or more organic layers.
In one embodiment of the present application, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be contained in 1 layer of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.
In addition, in one embodiment of the present application, in the case where the above-mentioned heterocyclic compounds are respectively contained in the above-mentioned 2 or more electron transport layers, materials other than the above-mentioned heterocyclic compounds may be the same as or different from each other.
In one embodiment of the present invention, the organic layer further includes a hole injection layer or a hole transport layer including a compound including an aromatic amino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the heterocyclic compound.
In another embodiment, the organic electroluminescent element may be an organic electroluminescent element having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic electroluminescent element may be an inverted (inverted) type organic electroluminescent element in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
For example, fig. 1 and 2 show an example of the structure of an organic electroluminescent element according to an embodiment of the present application.
Fig. 1 illustrates an example of the structure of an organic electroluminescent element in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the heterocyclic compound may be contained in the light-emitting layer 3.
Fig. 2 illustrates a structure of an organic electroluminescent element in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. In this structure, the heterocyclic compound may be contained in 1 or more of the hole injection layer 5, the hole transport layer 6, the light-emitting layer 3, and the electron transport layer 7.
In this structure, the heterocyclic compound may be contained in 1 or more of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport layer.
In the organic electroluminescent element of the present application, 1 or more of the organic layers contain the heterocyclic compound of the present application, that is, contain the above-mentioned heterocyclic compound, and in addition, can be produced by a material and a method known in the art.
When the organic electroluminescent element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
In the organic electroluminescent element of the present application, 1 or more layers of the organic layer may contain the heterocyclic compound, i.e., the compound represented by the above chemical formula 1, and may be produced using a material and a method known in the art.
For example, the organic electroluminescent element of the present application can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: 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) 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 electroluminescent element.
In addition, the heterocyclic compound of chemical formula 1 may be used not only for forming an organic layer by a vacuum deposition method but also for forming an organic layer by a solution coating method in the production of an organic electroluminescent element. 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 this method, an organic electroluminescent element may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.
In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, 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 that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO: 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 multi-layer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the 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 an example, there is 8-hydroxy-quinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are 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, theExamples of the aromatic fused ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and examples of the heterocyclic ring-containing compounds include dibenzofuran derivatives and ladder furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a substance 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 accompanying an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium were used, and in each case, they were accompanied by an aluminum layer or a 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 (Anthraqu inodimithane), diphenoquinone, thiopyran dioxide, and,Azole,Diazoles, triazolesImidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complexes include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), 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 hole-blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the hole-injecting layer. Specifically, there areAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.
The organic electroluminescent element according to the present specification may be of a top emission type, a bottom emission type, or a bidirectional emission type depending on the material used.
Examples
Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.
Synthesis example 1 Compound 1
10.0g (1.0eq) of the compound of formula 1A, 11.19g (1.1eq) of N- ([1,1':3',1 "-terphenyl)]-5' -yl) dibenzo [ b, d]Furan-4-amine, 698g (2.0eq) of NaOtBu, 0.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml of Xylene (Xylene) and stirred under reflux. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography gave 20.56g of Compound 1 (yield 87%). [ M + H ]]=651
Synthesis example 2 Compound 2
10.0g (1.0eq) of formula 1A, 11.19g (1.1eq) of N- (4- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) - [1,1' -biphenyl]4-amine, 6.98g (2.0eq) of NaOtBu, 0.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml of Xylene (Xylene) and stirred under reflux. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography gave 20.16g of Compound 2 (yield 82%). [ M + H ]]=677
Synthesis example 3 Compound 3
10.0g (1.0eq) of N- (4- (dibenzo [ b, d ] of formula 1A, 11.19g (1.1eq) of N- (1.1eq) were mixed]Furan-2-yl) phenyl) - [1,1':3', 1' -terphenyl]-5' -amine, 6.98g (2.0eq) of NaOtBu, 0.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml of Xylene (Xylene) and stirred under reflux. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Again under reflux, addEthyl acetate was added, the crystals were allowed to fall, cooled and filtered. Column chromatography thereof afforded 22.70g of compound 3 (yield 86%). [ M ] A]=726
Synthesis example 4 Compound 4
10.0g (1.0eq) of formula 1A, 24.28g (1.1eq) of (4- ([1,1':3', 1' -terphenyl)]-5' -yl (4- (dibenzo [ b, d ])]Furan-3-yl) phenyl) amino) phenyl) boronic acid, 15.43g (2.0eq) of K dissolved in 40ml of water3PO40.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml ofIn the alkane, reflux and stirring. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography gave 25.08g of Compound 4 (86% yield). [ M + H ]]=803
Synthesis example 5 Compound 5
10.0g (1.0eq) of chemical 1A, 8.39g (1.1eq) of (4- ([1,1' -biphenylyl) benzene]-4-yl (4- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) amino) phenyl) boronic acid, 15.43g (2.0eq) of K dissolved in 40ml of water3PO40.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml ofIn the alkane, reflux and stirring. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Washing with water, and reducing pressure to remove about 50%The solvent of (1). Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography thereof afforded 22.70g of compound 5 (yield 83%). [ M + H ]]=753
Synthesis example 6 Compound 6
10.0g (1.0eq) of (1A) of the formula, 9.89g (1.1eq) of (4- ([1,1' -biphenylyl) were added]-4-yl (4- (dibenzo [ b, d ])]Furan-4-yl) phenyl) amino) phenyl) boronic acid, 15.43g (2.0eq) of K dissolved in 40ml of water3PO40.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml ofIn the alkane, reflux and stirring. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again reduced in pressure to remove about 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography gave 22.44g of Compound 6 (85% yield). [ M + H ]]=727
Synthesis example 7 Compound 7
10.0g (1.0eq) of (1A of formula 1, 6.13g (1.1eq) of (4- ((4- (dibenzo [ b, d) are mixed together]Furan-4-yl) phenyl) (triphenylen-2-yl) amino) phenyl) boronic acid, 15.43g (2.0eq) of K dissolved in 40ml of water3PO40.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml ofIn the alkane, reflux and stirring. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3In the middle, washing with water, and feeding againThe pressure was reduced to remove about 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography thereof afforded 23.27g of compound 7 (yield 80%). [ M + H ]]=801
Synthesis example 8 Compound 8
10.0g (1.0eq) of formula 1A, 25.24g (1.1eq) of (4- ((4- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) (triphenylen-2-yl) amino) phenyl) boronic acid, 15.43g (2.0eq) of K dissolved in 40ml of water3PO40.09g (0.005eq) of Pd (t-Bu)3P)2Dissolved in 90ml ofIn the alkane, reflux and stirring. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. Then, completely dissolved in CHCl3Then, the mixture was washed with water and again subjected to reduced pressure to remove 50% of the solvent. Under reflux again, ethyl acetate was added to allow the crystals to fall, cooled and filtered. Column chromatography thereof afforded 24.33g of compound 8 (yield 81%). [ M + H ]]=827
< comparative example >
Will be provided withThe glass substrate coated with ITO (indium tin oxide) is put in distilled water dissolved with detergent and washed by ultrasonic wave. In this case, a product of fisher corporation (Fischer Co.) was used as the detergent, and distilled water obtained by filtering 2 times with a Filter (Filter) manufactured by Millipore corporation was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. In addition, oxygen plasma is used to makeAfter the substrate was cleaned for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus preparedThe hole injection layer was formed by thermally vacuum-evaporating hexaazatriphenylene (HAT-CN) of the following chemical formula. On the hole injection layer, the following compound HT as a hole transporting substance was addedThe hole transport layer was formed by vacuum evaporation. Then, on the above-mentioned hole transport layerThe following compound EB was vacuum-deposited to form an electron blocking layer. Then, on the above-mentioned electron blocking layerThe following BH and BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. The compound ET and the compound LiQ (Lithium 8-quinolinolate) were vacuum-deposited on the light-emitting layer at a weight ratio of 1:1 to form a layerThe thickness of (2) forms an electron injection and transport layer. Sequentially adding lithium fluoride (LiF) on the electron injection and transport layerThickness of aluminum andthe thickness was evaporated to form a cathode. In the above process, the evaporation speed of the organic material is maintainedLithium fluoride maintenance of cathodeDeposition rate of (3), aluminum maintenanceThe vacuum degree is maintained at 2X 10 during the vapor deposition-7~5×10-6torr, thereby an organic electroluminescent element was produced.
< Experimental examples 1-1>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 1 was used instead of compound EB in the comparative example.
< Experimental examples 1 and 2>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 2 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 3>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 3 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 4>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 4 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 5>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 5 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 6>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 6 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 7>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 7 was used instead of compound EB in the comparative example.
< Experimental examples 1 to 8>
An organic electroluminescent device was produced in the same manner as in comparative example except that compound 8 was used instead of compound EB in the comparative example.
< comparative example 1>
An organic electroluminescent element was produced in the same manner as in the comparative example except that the compound of H-1 was used instead of the compound EB in the comparative example.
< comparative example 2>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-2 was used instead of the compound EB in the comparative example.
< comparative example 3>
An organic electroluminescent device was fabricated in the same manner as in the comparative example, except that the compound of H-3 was used instead of the compound EB in the comparative example.
< comparative example 4>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-4 was used instead of the compound EB in the comparative example.
< comparative example 5>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-5 was used instead of the compound EB in the comparative example.
< comparative example 6>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-6 was used instead of the compound EB in the comparative example.
The results of measuring the voltage, current density, luminance, color coordinate, and lifetime when a current was applied to the organic electroluminescent elements fabricated in experimental examples 1-1 to 1-8 and comparative examples 1 to 6 are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (650nit) to 95%.
[ Table 1]
As shown in table 1, in the case of an organic electroluminescent element produced using the compound of the present invention as an electron blocking layer, the organic electroluminescent element exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability.
The core of the invention of the present application shows characteristics of low voltage, high efficiency and long life as compared with the organic electroluminescent element manufactured using the compounds of comparative examples 1 to 6 as an electron blocking layer. The voltage is reduced by about 5-10%, and the efficiency is increased by more than 10%. When the conventional indolo [3,2,1-jk ] carbazole compounds were connected in the direction of the amines bonded to nos. 2, 10 and 11 to the direction of the steric hindrance (No. 7) as in the compound of the present invention, and were connected in the direction of conjugate cleavage, the compounds exhibited characteristics of increased efficiency, reduced voltage and long life, and it was found that the stability of the core indolo [3,2,1-jk ] carbazole itself was also improved. In addition, since the portion of the core to which the amine is bonded is bent more, it is also excellent in thermal stability.
Claims (7)
1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, Ar1 and Ar2, which are the same as or different from each other, are each independently an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted triphenylene group, an unsubstituted dimethylfluorenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group,
l1 to L3, which are identical to or different from one another, are each independently a direct bond or a phenylene radical,
r1 to R3 are hydrogen,
a and c are 3, and b is 4.
3. an organic electroluminescent element, comprising: 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 at least one of the organic layers contains the heterocyclic compound according to claim 1 or 2.
4. The organic electroluminescent element according to claim 3, wherein the organic layer comprises a light-emitting layer containing the heterocyclic compound.
5. The organic electroluminescent element according to claim 3, wherein the organic layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the heterocyclic compound.
6. The organic electroluminescent element according to claim 3, wherein the organic layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the heterocyclic compound.
7. The organic electroluminescent element according to claim 3, wherein the organic layer comprises an electron blocking layer comprising the heterocyclic compound.
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