CN114728947B - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- CN114728947B CN114728947B CN202080077208.7A CN202080077208A CN114728947B CN 114728947 B CN114728947 B CN 114728947B CN 202080077208 A CN202080077208 A CN 202080077208A CN 114728947 B CN114728947 B CN 114728947B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 75
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- 239000000126 substance Substances 0.000 claims description 64
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- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 230000001629 suppression Effects 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 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 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MXVLMYZRJAHEIS-UHFFFAOYSA-N 1-(2-phenylphenyl)naphthalene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 MXVLMYZRJAHEIS-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
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- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 125000005462 imide group Chemical group 0.000 description 2
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- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- 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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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 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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- 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
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 229910052790 beryllium Inorganic materials 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
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- 125000000707 boryl group Chemical group B* 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
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 229940125782 compound 2 Drugs 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 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
- 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- 150000005041 phenanthrolines Chemical class 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 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
- 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
- 150000003230 pyrimidines Chemical class 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007761 roller coating 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
- 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 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
- 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
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 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
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明提供新型化合物及利用其的有机发光器件。
The present invention provides novel compounds and organic light-emitting devices using the same.
Description
技术领域Technical Field
与相关申请的相互引用Cross-references to related applications
本申请主张基于2020年2月13日的韩国专利申请第10-2020-0017590号和2020年12月15日的韩国专利申请第10-2020-0175628号的优先权，包含该韩国专利申请的文献中公开的全部内容作为本说明书的一部分。This application claims priority based on Korean Patent Application No. 10-2020-0017590 filed on February 13, 2020 and Korean Patent Application No. 10-2020-0175628 filed on December 15, 2020, and incorporates all the contents disclosed in the documents of the Korean patent applications as a part of this specification.
本发明涉及新型化合物及包含其的有机发光器件。The present invention relates to novel compounds and organic light-emitting devices comprising the same.
背景技术Background Art
通常情况下，有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件具有宽视角、优异的对比度、快速响应时间，亮度、驱动电压和响应速度特性优异，因此正在进行大量的研究。Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.
有机发光器件通常具有包括阳极和阴极以及位于上述阳极与阴极之间的有机物层的结构。为了提高有机发光器件的效率和稳定性，上述有机物层大多情况下由分别利用不同的物质构成的多层结构形成，例如，可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言，如果在两电极之间施加电压，则空穴从阳极注入有机物层，电子从阴极注入有机物层，当所注入的空穴和电子相遇时会形成激子(exciton)，该激子重新跃迁至基态时就会发出光。An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted.
对于用于如上所述的有机发光器件的有机物，持续要求开发新的材料。For organic substances used for organic light-emitting devices as described above, development of new materials is continuously required.
现有技术文献Prior art literature
专利文献Patent Literature
(专利文献1)韩国专利公开号第10-2000-0051826号(Patent Document 1) Korean Patent Publication No. 10-2000-0051826
发明内容Summary of the invention
技术课题Technical issues
本发明涉及新型化合物及包含其的有机发光器件。The present invention relates to novel compounds and organic light-emitting devices comprising the same.
课题的解决方法Solution to the problem
本发明提供由下述化学式1表示的化合物：The present invention provides a compound represented by the following Chemical Formula 1:
[化学式1][Chemical formula 1]
在上述化学式1中，In the above chemical formula 1,
Ar为C13-60芳基，上述Ar未被取代或者被至少一个氘、C1-18烷基、或C6-18芳基取代，Ar is a C 13-60 aryl group, which is unsubstituted or substituted with at least one deuterium, C 1-18 alkyl group, or C 6-18 aryl group,
R1至R4各自独立地为氢、氘、取代或未取代的C1-60烷基、或者取代或未取代的C6-60芳基，或者相邻的两个基团彼此结合而形成取代或未取代的芳香族环结构， R1 to R4 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-60 alkyl group, or a substituted or unsubstituted C6-60 aryl group, or two adjacent groups are combined to form a substituted or unsubstituted aromatic ring structure,
R5至R8各自独立地为氢；氘；卤素；腈基；甲硅烷基；取代或未取代的C1-60烷基；取代或未取代的C6-60芳基；取代或未取代的C2-60烯基；或者取代或未取代的包含选自N、O和S中的任一个或更多个杂原子的C2-60杂芳基， R5 to R8 are each independently hydrogen; deuterium; halogen; nitrile; silyl; substituted or unsubstituted C1-60 alkyl; substituted or unsubstituted C6-60 aryl; substituted or unsubstituted C2-60 alkenyl; or substituted or unsubstituted C2-60 heteroaryl containing any one or more heteroatoms selected from N, O and S,
m为0至3的整数，m is an integer from 0 to 3,
n为0至8的整数，n is an integer from 0 to 8,
p和q各自独立地为0至4的整数。p and q are each independently an integer of 0 to 4.
另外，本发明提供一种有机发光器件，其中，包括：第一电极、与上述第一电极对置而设置的第二电极、以及设置在上述第一电极与上述第二电极之间的一层或更多层有机物层，上述有机物层中的一层或更多层包含由上述化学式1表示的化合物。In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, one or more of the organic layers containing the compound represented by the above chemical formula 1.
发明效果Effects of the Invention
由上述化学式1表示的化合物可以用作有机发光器件的有机物层的材料，在有机发光器件中可以实现效率的提高、低的驱动电压和/或寿命特性的提高。特别是，由上述化学式1表示的化合物可以用作空穴注入、空穴传输、空穴注入和传输、发光、电子传输、或电子注入的材料。The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, low driving voltage and/or improved 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, light emission, electron transport, or electron injection.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
图1图示了由基板1、阳极2、有机物层3和阴极4构成的有机发光器件的例子。FIG. 1 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , an organic layer 3 , and a cathode 4 .
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子抑制层7、发光层8、空穴阻挡层9、电子注入和传输层10、以及阴极4构成的有机发光器件的例子。2 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , an electron suppression layer 7 , a light-emitting layer 8 , a hole blocking layer 9 , an electron injection and transport layer 10 , and a cathode 4 .
具体实施方式DETAILED DESCRIPTION
下面，为了帮助理解本发明而更详细地进行说明。In the following, the present invention will be described in more detail to help understanding the present invention.
在本说明书中，或表示与其它取代基连接的键。In this manual, or It represents the bond to other substituents.
在本说明书中，“取代或未取代的”这一用语是指被选自氘；卤素基团；腈基；硝基；羟基；羰基；酯基；酰亚胺基；氨基；氧化膦基；烷氧基；芳氧基；烷基硫氧基；芳基硫氧基；烷基磺酰基；芳基磺酰基；甲硅烷基；硼基；烷基；环烷基；烯基；芳基；芳烷基；芳烯基；烷基芳基；烷基胺基；芳烷基胺基；杂芳基胺基；芳基胺基；芳基膦基；或者包含N、O和S原子中的1个以上的杂环基中的1个以上的取代基取代或未取代，或者被上述例示的取代基中的2个以上的取代基连接而成的取代或未取代。例如，“2个以上的取代基连接而成的取代基”可以为联苯基。即，联苯基可以为芳基，也可以被解释为2个苯基连接而成的取代基。In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthiooxy group; arylthiooxy group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; or heterocyclic group containing one or more of N, O and S atoms, or substituted or unsubstituted by two or more substituents connected among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.
在本说明书中，羰基的碳原子数没有特别限定，但优选碳原子数为1至40。具体而言，可以为如下结构的化合物，但并不限定于此。In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
在本说明书中，酯基中，酯基的氧可以被碳原子数1至25的直链、支链或环状的烷基；或者碳原子数6至25的芳基取代。具体而言，可以为下述结构式的化合物，但并不限定于此。In the present specification, in the ester group, the oxygen of the ester group may be substituted by 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 of the following structural formula, but is not limited thereto.
在本说明书中，酰亚胺基的碳原子数没有特别限定，但优选碳原子数为1至25。具体而言，可以为如下结构的化合物，但并不限定于此。In the present specification, the number of carbon atoms in 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 the present invention is not limited thereto.
在本说明书中，甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等，但并不限定于此。In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.
在本说明书中，硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等，但并不限定于此。In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but the present invention is not limited thereto.
在本说明书中，作为卤素基团的例子，有氟、氯、溴或碘。In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
在本说明书中，上述烷基可以为直链或支链，碳原子数没有特别限定，但优选为1至40。根据一实施方式，上述烷基的碳原子数为1至20。根据另一实施方式，上述烷基的碳原子数为1至10。根据另一实施方式，上述烷基的碳原子数为1至6。作为烷基的具体例，有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等，但并不限定于此。In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.
在本说明书中，上述烯基可以为直链或支链，碳原子数没有特别限定，但优选为2至40。根据一实施方式，上述烯基的碳原子数为2至20。根据另一实施方式，上述烯基的碳原子数为2至10。根据另一实施方式，上述烯基的碳原子数为2至6。作为具体例，有乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等，但并不限定于此。In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.
在本说明书中，环烷基没有特别限定，但优选为碳原子数3至60的环烷基，根据一实施方式，上述环烷基的碳原子数为3至30。根据另一实施方式，上述环烷基的碳原子数为3至20。根据另一实施方式，上述环烷基的碳原子数为3至6。具体而言，有环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等，但并不限定于此。In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the 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, etc., but are not limited thereto.
在本说明书中，芳基没有特别限定，但优选为碳原子数6至60的芳基，可以为单环芳基或多环芳基。根据一实施方式，上述芳基的碳原子数为6至30。根据一实施方式，上述芳基的碳原子数为6至20。关于上述芳基，作为单环芳基，可以为苯基、联苯基、三联苯基等，但并不限定于此。作为上述多环芳基，可以为萘基、蒽基、菲基、芘基、苝基、基、芴基等，但并不限定于此。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 carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.
在本说明书中，芴基可以被取代，2个取代基可以彼此结合而形成螺结构。在上述芴基被取代的情况下，可以成为等。但并不限定于此。In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.
在本说明书中，杂环基是包含O、N、Si和S中的1个以上作为杂元素的杂环基，碳原子数没有特别限定，但优选碳原子数为2至60。作为杂环基的例子，有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基(phenanthroline)、异唑基、噻二唑基、吩噻嗪基和二苯并呋喃基等，但不仅限于此。In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.
在本说明书中，芳烷基、芳烯基、烷基芳基、芳基胺基中的芳基与上述的芳基的例示相同。在本说明书中，芳烷基、烷基芳基、烷基胺基中的烷基与上述的烷基的例示相同。在本说明书中，杂芳基胺中的杂芳基可以适用上述的关于杂环基的说明。在本说明书中，芳烯基中的烯基与上述的烯基的例示相同。在本说明书中，亚芳基为2价基团，除此以外，可以适用上述的关于芳基的说明。在本说明书中，亚杂芳基为2价基团，除此以外，可以适用上述的关于杂环基的说明。在本说明书中，烃环不是1价基团，而是2个取代基结合而成，除此以外，可以适用上述的关于芳基或环烷基的说明。在本说明书中，杂环不是1价基团，而是2个取代基结合而成，除此以外，可以适用上述的关于杂环基的说明。In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the aryl group described above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in aralkenyl is the same as the examples of the alkenyl group described above. In the present specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the aryl group or cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the heterocyclic group can be applied.
优选地，由上述化学式1表示的化合物可以由下述化学式1a至1d中的任一个表示：Preferably, the compound represented by the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1a to 1d:
[化学式1a][Chemical formula 1a]
[化学式1b][Chemical formula 1b]
[化学式1c][Chemical formula 1c]
[化学式1d][Chemical formula 1d]
在上述化学式1a至1d中，In the above chemical formulas 1a to 1d,
Ar、R1至R8、m、n、p和q与上述定义相同。Ar, R1 to R8 , m, n, p and q are the same as defined above.
另外，在上述化学式1中，优选地，Ar为三联苯基、(苯基)萘基、(萘基)苯基、(萘基)联苯基、(苯基萘基)苯基、二甲基芴基、二苯基芴基、三亚苯基、菲基或(菲基)苯基，In addition, in the above chemical formula 1, preferably, Ar is terphenyl, (phenyl) naphthyl, (naphthyl) phenyl, (naphthyl) biphenyl, (phenyl naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, triphenylene, phenanthryl or (phenanthryl) phenyl,
上述Ar可以未被取代或者被至少一个氘、C1-18烷基、或C6-18芳基取代。The above Ar may be unsubstituted or substituted with at least one deuterium, C 1-18 alkyl, or C 6-18 aryl.
更优选地，Ar可以为选自下述化学式中的任一个：More preferably, Ar can be any one selected from the following chemical formulas:
在上述各化学式中，In the above chemical formulas,
R11相同或不同，各自为氢、氘、C1-18烷基、或C6-18芳基，优选地，上述R11相同或不同，各自为氢、氘、甲基或苯基，R 11 are the same or different, and each is hydrogen, deuterium, C 1-18 alkyl, or C 6-18 aryl. Preferably, the above R 11 are the same or different, and each is hydrogen, deuterium, methyl, or phenyl.
虚线表示结合位置。Dashed lines indicate binding positions.
另外，在上述化学式1中，R1至R4可以各自独立地为氢、氘或苯基。In addition, in the above Chemical Formula 1, R1 to R4 may each independently be hydrogen, deuterium or a phenyl group.
优选地，R1至R4可以均为氢或者均为氘。Preferably, R 1 to R 4 may all be hydrogen or all be deuterium.
优选地，R1至R4中的一个为苯基，其余可以为氢或氘。Preferably, one of R1 to R4 is phenyl, and the others may be hydrogen or deuterium.
优选地，R1和R2、R2和R3、以及R3和R4中的任一个彼此结合而形成取代或未取代的苯基结构，或者R1和R2、以及R3和R4两个各自彼此结合而形成取代或未取代的苯基结构，其余可以为氢。此外，在上述苯基结构被取代的情况下，可以被至少一个氢或氘取代。Preferably, any one of R1 and R2 , R2 and R3 , and R3 and R4 is combined with each other to form a substituted or unsubstituted phenyl structure, or R1 and R2 , and R3 and R4 are each combined with each other to form a substituted or unsubstituted phenyl structure, and the rest may be hydrogen. In addition, when the above phenyl structure is substituted, it may be substituted by at least one hydrogen or deuterium.
另外，在上述化学式1中，R5至R8可以各自独立地为氢或氘，优选地，R5至R8可以均为氢或者均为氘。In addition, in the above Chemical Formula 1, R5 to R8 may each independently be hydrogen or deuterium. Preferably, R5 to R8 may all be hydrogen or deuterium.
由上述化学式1表示的化合物的代表性的例子如下所示：Representative examples of the compound represented by the above Chemical Formula 1 are shown below:
另外，作为一个例子，本发明提供如下述反应式1所示的由上述化学式1表示的化合物的制造方法。In addition, as an example, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.
[反应式1][Reaction 1]
在上述反应式1中，Ar、R1至R8、m、n、p和q与上述化学式1中的定义相同，X为卤素，优选地，X为氯或溴。In the above reaction formula 1, Ar, R 1 to R 8 , m, n, p and q are the same as those defined in the above chemical formula 1, and X is a halogen, preferably, X is chlorine or bromine.
上述反应式1为胺取代反应，优选在钯催化剂和碱的存在下进行，用于胺取代反应的反应基团可以根据本领域中已知的技术进行变更。上述制造方法可以在后述的制造例中更具体化。The above reaction formula 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be changed according to the techniques known in the art. The above production method can be further specified in the production examples described below.
另外，本发明提供包含由上述化学式1表示的化合物的有机发光器件。作为一个例子，本发明提供一种有机发光器件，其中，包括：第一电极、与上述第一电极对置而设置的第二电极、以及设置在上述第一电极与上述第二电极之间的一层或更多层有机物层，上述有机物层中的一层或更多层包含由上述化学式1表示的化合物。In addition, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.
本发明的有机发光器件的有机物层可以由单层结构形成，但还可以由层叠有2层以上的有机物层的多层结构形成。例如，本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、电子抑制层、同时进行电子注入和电子传输的电子注入和传输层等作为有机物层的结构。但是，有机发光器件的结构并不限定于此，可以包括更少数量的有机物层。The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, but may also be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron suppression layer, an electron injection and transport layer that simultaneously performs electron injection and electron transport, etc. as an organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.
另外，上述有机物层可以包括发光层，上述发光层包含由上述化学式1表示的化合物。In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.
另外，上述有机物层可以包括电子传输层、电子注入层、或者电子注入和传输层，上述电子传输层、电子注入层、或者电子注入和传输层包含由上述化学式1表示的化合物。In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.
另外，上述有机物层可以包括电子抑制层，上述电子抑制层包含由上述化学式1表示的化合物。In addition, the organic layer may include an electron suppressing layer, and the electron suppressing layer may include the compound represented by Chemical Formula 1.
另外，根据本发明的有机发光器件可以是在基板上依次层叠有阳极、一层或更多层有机物层和阴极的结构(正常型(normal type))的有机发光器件。此外，根据本发明的有机发光器件可以是在基板上依次层叠有阴极、一层或更多层有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。例如，根据本发明的一个实施例的有机发光器件的结构例示于图1和图2。In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
图1图示了由基板1、阳极2、有机物层3和阴极4构成的有机发光器件的例子。在如上所述的结构中，由上述化学式1表示的化合物可以包含在上述有机物层3中。1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, an organic 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 organic layer 3.
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子抑制层7、发光层8、空穴阻挡层9、电子注入和传输层10、以及阴极4构成的有机发光器件的例子。在如上所述的结构中，由上述化学式1表示的化合物可以包含在上述空穴注入层5、空穴传输层6、电子抑制层7、发光层8、空穴阻挡层9、以及电子注入和传输层10中的一层或更多层中。2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and 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 5, hole transport layer 6, electron suppression layer 7, light-emitting layer 8, hole blocking layer 9, and electron injection and transport layer 10.
根据本发明的有机发光器件除了上述有机物层中的一层或更多层包含由上述化学式1表示的化合物以外，可以利用该技术领域中已知的材料和方法进行制造。此外，上述有机发光器件包括复数个有机物层时，上述有机物层可以由相同的物质或不同的物质形成。The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that one or more of the organic layers contain the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.
例如，根据本发明的有机发光器件可以通过在基板上依次层叠第一电极、有机物层和第二电极而制造。这时可以如下制造：利用溅射法(sputtering)或电子束蒸发法(e-beam evaporation)之类的PVD(physical Vapor Deposition：物理气相沉积)方法，在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极，然后在该阳极上形成包括空穴注入层、空穴传输层、电子抑制层、发光层、空穴阻挡层、以及电子注入和传输层的有机物层，之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外，也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking layer, and an electron injection and transport layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.
另外，由上述化学式1表示的化合物在制造有机发光器件时不仅可以利用真空蒸镀法，还可以利用溶液涂布法来形成有机物层。在这里，所谓溶液涂布法是指旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等，但并不仅限于此。In addition, the compound represented by the above chemical formula 1 can be used to form an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.
除了这些方法以外，还可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件(WO 2003/012890)。但是，制造方法并不限定于此。In addition to these methods, an organic light-emitting device can also 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 to this.
作为一个例子，上述第一电极为阳极，上述第二电极为阴极，或者上述第一电极为阴极，上述第二电极为阳极。As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
作为上述阳极物质，通常为了使空穴能够顺利地向有机物层注入，优选为功函数大的物质。作为上述阳极物质的具体例，有钒、铬、铜、锌、金等金属或它们的合金；氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物；ZnO:Al或SnO2:Sb等金属与氧化物的组合；聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等，但并不仅限于此。In order to smoothly inject holes into the organic layer, the anode material is preferably a material with a large work function. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
作为上述阴极物质，通常为了使电子容易地向有机物层注入，优选为功函数小的物质。作为上述阴极物质的具体例，有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金；LiF/Al或LiO2/Al等多层结构物质等，但并不仅限于此。The cathode material is preferably a material with a small work function in order to facilitate electron injection 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, or alloys thereof; multilayer structure materials such as LiF/Al or LiO2 /Al, but are not limited thereto.
上述空穴注入层是注入来自电极的空穴的层，作为空穴注入物质，优选为如下化合物：具有传输空穴的能力，具有注入来自阳极的空穴的效果，具有对于发光层或发光材料的优异的空穴注入效果，防止发光层中生成的激子向电子注入层或电子注入材料迁移，而且薄膜形成能力优异的化合物。优选空穴注入物质的HOMO(最高占有分子轨道，highestoccupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体例，有金属卟啉(porphyrin)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚噻吩系的导电性高分子等，但并不仅限于此。The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyanilines, and polythiophene conductive polymers, but are not limited thereto.
上述空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层，作为空穴传输物质，是能够接收来自阳极或空穴注入层的空穴并将其转移至发光层的物质，对空穴的迁移率大的物质是合适的。作为具体例，有芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等，但并不仅限于此。The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A material with a large hole mobility is suitable. Specific examples include arylamine organics, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.
上述电子抑制层是指如下的层：形成在上述空穴传输层上，优选与发光层相接而设置，通过调节空穴迁移率，防止电子的过度迁移而提高空穴-电子之间的结合几率，从而起到改善有机发光器件的效率的作用的层。上述电子抑制层包含电子阻挡物质，作为这样的电子阻挡物质的例子，可以使用由上述化学式1表示的化合物，或者可以使用芳基胺系的有机物等，但并不限定于此。The electron suppression layer is a layer formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the hole mobility, preventing the excessive migration of electrons, and increasing the probability of the combination between holes and electrons. The electron suppression layer includes an electron blocking substance. As an example of such an electron blocking substance, a compound represented by the above chemical formula 1 or an arylamine-based organic substance can be used, but it is not limited thereto.
上述发光物质是能够从空穴传输层和电子传输层分别接收空穴和电子并使它们结合而发出可见光区域的光的物质，优选对于荧光或磷光的量子效率高的物质。作为具体例，有8-羟基-喹啉铝配合物(Alq3)；咔唑系化合物；二聚苯乙烯基(dimerized styryl)化合物；BAlq；10-羟基苯并喹啉-金属化合物；苯并唑、苯并噻唑及苯并咪唑系化合物；聚(对亚苯基亚乙烯基)(PPV)系高分子；螺环(spiro)化合物；聚芴、红荧烯等，但并不仅限于此。The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region. It is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.
上述发光层可以包含主体材料和掺杂剂材料。主体材料有芳香族稠环衍生物或含杂环化合物等。具体而言，作为芳香族稠环衍生物，有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等，作为含杂环化合物，有咔唑衍生物、二苯并呋喃衍生物、梯型呋喃化合物、嘧啶衍生物等，但并不限定于此。The light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as the aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.
作为掺杂剂材料，有芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体而言，芳香族胺衍生物是具有取代或未取代的芳基氨基的芳香族稠环衍生物，有具有芳基氨基的芘、蒽、二茚并芘等，苯乙烯基胺化合物是在取代或未取代的芳基胺上取代有至少1个芳基乙烯基的化合物，被选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的1个或2个以上的取代基取代或未取代。具体而言，有苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等，但并不限定于此。此外，作为金属配合物，有铱配合物、铂配合物等，但并不限定于此。As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.
上述空穴阻挡层是指如下的层：形成在发光层上，优选与发光层相接而设置，通过调节电子迁移率，防止空穴的过度迁移而提高空穴-电子之间的结合几率，从而起到改善有机发光层器件的效率的作用的层。上述空穴阻挡层包含空穴阻挡物质，作为这样的空穴阻挡物质的例子，可以使用包括三嗪的吖嗪类衍生物、三唑衍生物、二唑衍生物、菲咯啉衍生物、氧化膦衍生物等导入有吸电子基团的化合物，但并不限定于此。The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting layer device by adjusting the electron mobility, preventing the excessive migration of holes and increasing the probability of the combination between holes and electrons. The hole blocking layer contains a hole blocking substance. Examples of such a hole blocking substance include azine derivatives including triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.
上述电子注入和传输层是注入来自电极的电子并将接收的电子传输至发光层的同时起到电子传输层和电子注入层的作用的层，形成在上述发光层或上述空穴阻挡层上。这样的电子注入和传输物质是能够从阴极良好地接收电子并将其转移至发光层的物质，对电子的迁移率大的物质是合适的。作为具体的电子注入和传输物质的例子，有8-羟基喹啉的Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄酮-金属配合物、三嗪衍生物等，但不仅限于此。或者也可以与芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、或含氮五元环衍生物等一同使用，但并不限定于此。The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer while playing the role of an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such electron injection and transport substances are substances that can well receive electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. Specific examples of electron injection and transport substances include Al complexes of 8-hydroxyquinoline, complexes containing Alq 3 , organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.
作为上述金属配位化合物，有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等，但并不限定于此。Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, 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, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.
根据所使用的材料，根据本发明的有机发光器件可以为顶部发光型、底部发光型或双向发光型。The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.
另外，由上述化学式1表示的化合物除了包含在有机发光器件中以外，还可以包含在有机太阳能电池或有机晶体管中。In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to being included in an organic light emitting device.
由上述化学式1表示的化合物及包含其的有机发光器件的制造在下面的实施例中具体地进行说明。但是，下述实施例用于例示本发明，本发明的范围并不限定于此。The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.
制造例1Production Example 1
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.49g，21.22mmol)和化合物a1(10.03g，24.40mmol)完全溶解于280mL的二甲苯(Xylene)后，添加NaOtBu(2.65g，27.58mmol)，加入双(三叔丁基膦)钯(0)(Bis(tri-tert-butylphosphine)palladium(0))(0.24g，0.48mmol)后，加热搅拌3小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用260mL的乙酸乙酯重结晶，从而制造了上述结构的化合物1(8.16g，收率：53％)。Under nitrogen atmosphere, in a 500 ml round-bottom flask, compound A (7.49 g, 21.22 mmol) and compound a1 (10.03 g, 24.40 mmol) were completely dissolved in 280 ml of xylene, and then NaOtBu (2.65 g, 27.58 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.24 g, 0.48 mmol) were added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized with 260 ml of ethyl acetate to produce compound 1 (8.16 g, yield: 53%) of the above structure.
MS[M+H]+＝729MS[M+H] + ＝729
制造例2Production Example 2
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(6.85g，19.41mmol)和化合物a2(10.29g，22.32mmol)完全溶解于240mL的二甲苯后，添加NaOtBu(2.42g，25.23mmol)，加入双(三叔丁基膦)钯(0)(0.20g，0.39mmol)后，加热搅拌5小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用220mL的乙酸乙酯重结晶，从而制造了上述结构的化合物2(6.77g，收率：45％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (6.85g, 19.41mmol) and compound a2 (10.29g, 22.32mmol) were completely dissolved in 240mL of xylene, and NaOtBu (2.42g, 25.23mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.20g, 0.39mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 220mL of ethyl acetate, thereby producing compound 2 (6.77g, yield: 45%) of the above structure.
MS[M+H]+＝779MS[M+H] + ＝779
制造例3Production Example 3
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.11g，20.14mmol)和化合物a3(8.31g，22.16mmol)完全溶解于230mL的二甲苯后，添加NaOtBu(2.52g，26.18mmol)，加入双(三叔丁基膦)钯(0)(0.21g，0.40mmol)后，加热搅拌4小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用270mL的乙酸乙酯重结晶，从而制造了上述结构的化合物3(8.49g，收率：61％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.11g, 20.14mmol) and compound a3 (8.31g, 22.16mmol) were completely dissolved in 230mL of xylene, and NaOtBu (2.52g, 26.18mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.21g, 0.40mmol) was added, and heated and stirred for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 270mL of ethyl acetate, thereby producing compound 3 (8.49g, yield: 61%) of the above structure.
MS[M+H]+＝693MS[M+H] + ＝693
制造例4Production Example 4
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(6.82g，19.32mmol)和化合物a4(9.24g，21.25mmol)完全溶解于250mL的二甲苯后，添加NaOtBu(2.41g，25.12mmol)，加入双(三叔丁基膦)钯(0)(0.18g，0.36mmol)后，加热搅拌4小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用280mL的乙酸乙酯重结晶，从而制造了上述结构的化合物4(6.98g，收率：54％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (6.82g, 19.32mmol) and compound a4 (9.24g, 21.25mmol) were completely dissolved in 250mL of xylene, and NaOtBu (2.41g, 25.12mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.18g, 0.36mmol) was added, and heated and stirred for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 280mL of ethyl acetate, thereby producing compound 4 (6.98g, yield: 54%) of the above structure.
MS[M+H]+＝753MS[M+H] + ＝753
制造例5Production Example 5
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.53g，21.33mmol)和化合物a5(10.21g，23.46mmol)完全溶解于260mL的二甲苯后，添加NaOtBu(2.66g，27.73mmol)，加入双(三叔丁基膦)钯(0)(0.22g，0.43mmol)后，加热搅拌5小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用270mL的乙酸乙酯重结晶，从而制造了上述结构的化合物5(7.61g，收率：49％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.53g, 21.33mmol) and compound a5 (10.21g, 23.46mmol) were completely dissolved in 260mL of xylene, and NaOtBu (2.66g, 27.73mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.22g, 0.43mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 270mL of ethyl acetate, thereby producing compound 5 (7.61g, yield: 49%) of the above structure.
MS[M+H]+＝729MS[M+H] + ＝729
制造例6Production Example 6
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.34g，20.79mmol)和化合物a6(11.09g，22.87mmol)完全溶解于240mL的二甲苯后，添加NaOtBu(3.31g，34.45mmol)，加入双(三叔丁基膦)钯(0)(0.21g，0.42mmol)后，加热搅拌3小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用240mL的乙酸乙酯重结晶，从而制造了上述结构的化合物6(8.62g，收率：53％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.34g, 20.79mmol) and compound a6 (11.09g, 22.87mmol) were completely dissolved in 240mL of xylene, and NaOtBu (3.31g, 34.45mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.21g, 0.42mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240mL of ethyl acetate, thereby producing compound 6 (8.62g, yield: 53%) of the above structure.
MS[M+H]+＝779MS[M+H] + ＝779
制造例7Production Example 7
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.55g，21.39mmol)和化合物a7(9.69g，23.53mmol)完全溶解于230mL的二甲苯后，添加NaOtBu(2.67g，27.80mmol)，加入双(三叔丁基膦)钯(0)(0.22g，0.43mmol)后，加热搅拌5小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用250mL的乙酸乙酯重结晶，从而制造了上述结构的化合物7(9.11g，收率：61％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.55g, 21.39mmol) and compound a7 (9.69g, 23.53mmol) were completely dissolved in 230mL of xylene, and NaOtBu (2.67g, 27.80mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.22g, 0.43mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 250mL of ethyl acetate, thereby producing compound 7 (9.11g, yield: 61%) of the above structure.
MS[M+H]+＝703MS[M+H] + ＝703
制造例8Production Example 8
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.78g，14.34mmol)和化合物a8(7.44g，16.49mmol)完全溶解于250mL的二甲苯后，添加NaOtBu(2.07g，21.51mmol)，加入双(三叔丁基膦)钯(0)(0.15g，0.29mmol)后，加热搅拌5小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用230mL的乙酸乙酯重结晶，从而制造了上述结构的化合物8(6.79g，收率：58％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.78g, 14.34mmol) and compound a8 (7.44g, 16.49mmol) were completely dissolved in 250mL of xylene, and NaOtBu (2.07g, 21.51mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.15g, 0.29mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 230mL of ethyl acetate, thereby producing compound 8 (6.79g, yield: 58%) of the above structure.
MS[M+H]+＝803MS[M+H] + ＝803
制造例9Production Example 9
在氮气氛下，在500ml的圆底烧瓶中，将化合物A(7.62g，21.59mmol)和化合物a9(12.11g，23.75mmol)完全溶解于230mL的二甲苯后，添加NaOtBu(2.70g，28.06mmol)，加入双(三叔丁基膦)钯(0)(0.22g，0.43mmol)后，加热搅拌4小时。将温度降低至常温，过滤而去除碱后，将二甲苯减压浓缩，用270mL的四氢呋喃重结晶，从而制造了上述结构的化合物9(10.57g，收率：61％)。Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (7.62g, 21.59mmol) and compound a9 (12.11g, 23.75mmol) were completely dissolved in 230mL of xylene, and NaOtBu (2.70g, 28.06mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.22g, 0.43mmol) was added, and heated and stirred for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 270mL of tetrahydrofuran, thereby preparing compound 9 (10.57g, yield: 61%) of the above structure.
MS[M+H]+＝818MS[M+H] + ＝818
实施例1Example 1
将ITO(氧化铟锡，indium tin oxide)以的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中，利用超声波进行洗涤。这时，洗涤剂使用菲希尔公司(Fischer Co.)制品，蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后，用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后，用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后，输送至等离子体清洗机。此外，利用氧等离子体，将上述基板清洗5分钟后，将基板输送至真空蒸镀机。ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropyl alcohol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
在这样准备的作为阳极的ITO透明电极上，将下述化合物HI1和下述化合物HI2的化合物以成为98:2(摩尔比)的比的方式，以的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上，将下述化合物HT1进行真空蒸镀而形成空穴传输层。接着，在上述空穴传输层上，以膜厚度将制造例1的化合物(1)进行真空蒸镀而形成电子抑制层。接着，在上述电子抑制层上，以膜厚度将下述化合物BH和下述化合物BD以25:1的重量比进行真空蒸镀而形成发光层。在上述发光层上，以膜厚度将下述化合物HB1进行真空蒸镀而形成空穴阻挡层。接着，在上述空穴阻挡层上，将下述化合物ET1和下述化合物LiQ以1:1的重量比进行真空蒸镀，从而以的厚度形成电子注入和传输层。在上述电子注入和传输层上，依次将氟化锂(LiF)以的厚度、将铝以的厚度进行蒸镀，从而形成阴极。On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio). The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following compound HT1 was deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The compound (1) of Preparation Example 1 was vacuum deposited to form an electron suppression layer. Next, a film having a film thickness of The following compound BH and the following compound BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer. The following compound HB1 was vacuum-deposited to form a hole blocking layer. Next, the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .
在上述过程中，有机物的蒸镀速度维持阴极的氟化锂维持的蒸镀速度，铝维持的蒸镀速度，在蒸镀时，真空度维持2×10-7～5×10-6托，从而制作了有机发光器件。In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 to 5×10 -6 torr, and the vacuum degree is maintained during evaporation, thereby producing an organic light-emitting device.
实施例2至9Examples 2 to 9
使用下述表1中记载的化合物代替制造例1的化合物1，除此以外，通过与上述实施例1相同的方法制造了有机发光器件。An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in Table 1 below were used instead of Compound 1 in Manufacturing Example 1.
比较例1至7Comparative Examples 1 to 7
使用下述表1中记载的化合物代替制造例1的化合物，除此以外，通过与上述实施例1相同的方法制造了有机发光器件。下述表1中使用的EB1、EB2、EB3、EB4、EB5、EB6和EB7如下所示。An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in Table 1 below were used instead of the compounds in Preparation Example 1. EB1, EB2, EB3, EB4, EB5, EB6, and EB7 used in Table 1 below are as follows.
实验例1Experimental Example 1
对上述实施例和比较例中制造的有机发光器件施加电流时，测定了电压、效率、色坐标和寿命，将其结果示于下述表1。T95是指亮度从初始亮度(1600尼特)减少至95％所需的时间。When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[表1][Table 1]
如上述表1所示，使用本发明的化合物作为电子抑制层的实施例1至9的有机发光器件在效率、驱动电压和稳定性方面显示出优异的特性。具体而言，实施例1至9的有机发光器件通过将在联苯基的邻位连接有被二苯并噻吩直接取代的胺物质用作电子抑制层，从而显示出低电压、高效率和长寿命的特性。As shown in Table 1, the organic light-emitting devices of Examples 1 to 9 using the compounds of the present invention as electron suppression layers exhibit excellent characteristics in terms of efficiency, driving voltage and stability. Specifically, the organic light-emitting devices of Examples 1 to 9 exhibit low voltage, high efficiency and long life by using an amine substance directly substituted with dibenzothiophene connected to the ortho position of a biphenyl group as an electron suppression layer.
相反，使用了在联苯基的对位连接有胺系取代基的化合物EB1和EB3的比较例1和3的有机发光器件，在电压升高、效率降低、特别是稳定性方面与实施例相比，显示出劣化的特性。此外，将包含2个在联苯基的邻位连接咔唑基的官能团的化合物EB2用作电子抑制层的比较例2；将咔唑基对于联苯基的结合位置为间位的化合物EB4用作电子抑制层的比较例4；以及将二苯并呋喃基不与氨基直接结合，而是通过亚苯基等连接基团进行结合的化合物用作电子抑制层的比较例5；以及将在化学式1中的Ar位置上包含联苯基而没有满足碳原子数条件的化合物EB6和EB7用作电子抑制层的比较例6和7的有机发光器件与实施例相比，同样在效率、驱动电压和稳定性方面显示出劣化的特性。On the contrary, the organic light-emitting devices of Comparative Examples 1 and 3 using compounds EB1 and EB3 having an amine substituent attached to the para position of the biphenyl group showed degraded characteristics in terms of voltage increase, efficiency decrease, and especially stability compared with the examples. In addition, the organic light-emitting devices of Comparative Examples 2 using compound EB2 containing two functional groups of carbazole groups attached to the ortho position of the biphenyl group as the electron suppression layer; Comparative Example 4 using compound EB4 in which the carbazole group is attached to the biphenyl group at the meta position as the electron suppression layer; and Comparative Example 5 using a compound in which the dibenzofuran group is not directly attached to the amino group but is attached via a connecting group such as a phenylene group as the electron suppression layer; and Comparative Examples 6 and 7 using compounds EB6 and EB7 containing a biphenyl group at the Ar position in Chemical Formula 1 but not satisfying the carbon atom number condition as the electron suppression layer also showed degraded characteristics in terms of efficiency, driving voltage, and stability compared with the examples.
通过上述内容对本发明的优选实施例(电子抑制层)进行了说明，但本发明并不限定于此，在本发明要求保护的范围和发明的详细说明的范围内可以变形为各种形态而实施，这也属于本发明的范畴。The preferred embodiment (electron suppression layer) of the present invention is described above, but the present invention is not limited thereto and can be implemented in various forms within the scope of protection claimed by the present invention and the scope of the detailed description of the invention, which also belongs to the scope of the present invention.
[符号说明][Explanation of symbols]
1：基板 2：阳极1: Substrate 2: Anode
3：有机物层 4：阴极3: Organic layer 4: Cathode
5：空穴注入层 6：空穴传输层5: Hole injection layer 6: Hole transport layer
7：电子抑制层 8：发光层7: Electron suppression layer 8: Light-emitting layer
9：空穴阻挡层 10：电子注入和传输层。9: Hole blocking layer 10: Electron injection and transport layer.
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| KR102292572B1 (en) * | 2014-11-07 | 2021-08-24 | 덕산네오룩스 주식회사 | Display device using a composition for organic electronic element, and an organic electronic element thereof |
| KR102107875B1 (en) * | 2016-06-02 | 2020-05-07 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| KR102021584B1 (en) * | 2017-02-24 | 2019-09-16 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| JP2020093979A (en) * | 2017-03-08 | 2020-06-18 | 出光興産株式会社 | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
| KR102705700B1 (en) * | 2018-11-30 | 2024-09-10 | 이데미쓰 고산 가부시키가이샤 | Compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices |
-
2020
- 2020-12-16 WO PCT/KR2020/018434 patent/WO2021162227A1/en active Application Filing
- 2020-12-16 CN CN202080077208.7A patent/CN114728947B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016072690A1 (en) * | 2014-11-04 | 2016-05-12 | 덕산네오룩스 주식회사 | Organic electronic device and display device using composition for organic electronic device |
| CN109096268A (en) * | 2018-09-11 | 2018-12-28 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescent compounds and its organic electroluminescence device |
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| WO2021162227A1 (en) | 2021-08-19 |
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