CN111630038A - 新的化合物和包含其的有机发光器件 - Google Patents
新的化合物和包含其的有机发光器件 Download PDFInfo
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- CN111630038A CN111630038A CN201980008733.0A CN201980008733A CN111630038A CN 111630038 A CN111630038 A CN 111630038A CN 201980008733 A CN201980008733 A CN 201980008733A CN 111630038 A CN111630038 A CN 111630038A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 93
- -1 dibenzofuranyl Chemical group 0.000 claims description 55
- 239000011368 organic material Substances 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 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
- 125000000732 arylene group Chemical group 0.000 claims description 3
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- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
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- 239000010410 layer Substances 0.000 description 143
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- 230000032258 transport Effects 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
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- 230000000903 blocking effect Effects 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
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- 229940126062 Compound A Drugs 0.000 description 4
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
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- 125000004185 ester group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- 125000006024 2-pentenyl group Chemical group 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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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- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
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- 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
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 229910052710 silicon Inorganic materials 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
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- 238000004528 spin coating Methods 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition 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
- 238000007740 vapor deposition Methods 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
- 238000005406 washing Methods 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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Abstract
本发明提供了新的化合物和包含其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2018年5月3日向韩国知识产权局提交的韩国专利申请第10-2018-0051361号的申请日的权益,其全部内容通过引用并入本文。
本发明涉及新的化合物和包含其的有机发光器件。
背景技术
通常,有机发光现象是指通过使用有机材料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诸如宽视角,优异的对比度,快速的响应时间,优异的亮度、驱动电压和响应速度的特性,并因此进行了许多研究。
有机发光器件通常具有包括阳极、阴极和介于阳极与阴极之间的有机材料层的结构。有机材料层通常具有包含不同材料的多层结构以增强有机发光器件的效率和稳定性,例如,有机材料层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层,电子从阴极注入有机材料层,当注入的空穴和电子彼此相遇时,形成激子,并且当激子再落至基态时发光。
持续需要开发用于在这些有机发光器件中使用的有机材料的新材料。
[现有技术文献]
[专利文献]
(专利文献0001)韩国专利特许公开第10-2000-0051826号
发明内容
技术问题
本发明的目的是提供新的化合物和包含其的有机发光器件。
技术方案
在本发明的一个方面中,提供了由以下化学式1表示的化合物:
[化学式1]
在化学式1中,
L为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60亚杂芳基,以及
Ar为经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基。
在本发明的另一个方面中,提供了有机发光器件,其包括:第一电极;设置成与第一电极相对的第二电极;和设置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层的一个或更多个层包含由化学式1表示的化合物。
有益效果
上述由化学式1表示的化合物可以用作有机发光器件的有机材料层的材料,并且可以在有机发光器件中改善效率,实现低驱动电压和/或改善寿命特性。特别地,上述由化学式1表示的化合物可以用作用于空穴注入、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。
附图说明
图1示出了包括基底1、阳极2、有机材料层3和阴极4的有机发光器件的实例。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层7、发光层8、空穴阻挡层9、电子传输层10、电子注入层11和阴极4的有机发光器件的实例。
具体实施方式
在下文中,将更详细地描述本发明以帮助理解本发明。
在本发明的一个实施方案中,提供了由化学式1表示的化合物。
如本文所用,术语“经取代或未经取代的”意指未经取代或者经选自以下的一个或更多个取代基取代: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;烷基硫基;芳基硫基;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;和包含N、O和S原子中的至少一者的杂环基,或者未经取代或者经以上例示的取代基中的两个或更多个取代基连接的取代基取代。例如,“两个或更多个取代基连接的取代基”可以为联苯基。即,联苯基可以为芳基,并且还可以被解释为两个苯基连接的取代基。
在本说明书中,羰基的碳原子数没有特别限制,但优选为1至40。具体地,羰基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,对于酯基,酯基的氧可以经具有1至25个碳原子的直链、支链或环状烷基,或者具有6至25个碳原子的芳基取代。具体地,酯基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,酰亚胺基的碳原子数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为具有以下结构式的化合物,但不限于此。
在本说明书中,甲硅烷基具体包括三甲基甲硅烷基、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,但不限于此。
在本说明书中,硼基具体包括三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基和苯基硼基,但不限于此。
在本说明书中,卤素基团的实例包括氟、氯、溴或碘。
在本说明书中,烷基可以为直链或支链,并且其碳原子数没有特别限制,但优选为1至40。根据一个实施方案,烷基的碳原子数为1至20。根据另一个实施方案,烷基的碳原子数为1至10。根据另一个实施方案,烷基的碳原子数为1至6。烷基的具体实例包括甲基、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,但不限于此。
在本说明书中,烯基可以为直链或支链,并且其碳原子数没有特别限制,但优选为2至40。根据一个实施方案,烯基的碳原子数为2至20。根据另一个实施方案,烯基的碳原子数为2至10。根据又一个实施方案,烯基的碳原子数为2至6。其具体实例包括乙烯基、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-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、基、苯乙烯基等,但不限于此。
在本说明书中,环烷基没有特别限制,但其碳原子数优选为3至60。根据一个实施方案,环烷基的碳原子数为3至30。根据另一个实施方案,环烷基的碳原子数为3至20。根据又一个实施方案,环烷基的碳原子数为3至6。其具体实例包括环丙基、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,但不限于此。
在本说明书中,芳基没有特别限制,但优选具有6至60个碳原子,并且可以为单环芳基或多环芳基。根据一个实施方案,芳基的碳原子数为6至30。根据一个实施方案,芳基的碳原子数为6至20。作为单环芳基,芳基可以为苯基、联苯基、三联苯基等,但不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、基、基和芴基等,但不限于此。
在本说明书中,杂环基为包含O、N、Si和S中的一者或更多者作为杂原子的杂环基,并且其碳原子数没有特别限制,但优选为2至60。杂环基的实例包括噻吩基、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、异唑基、噻二唑基、吩噻嗪基、二苯并呋喃基等,但不限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基与芳基的前述实例相同。在本说明书中,芳烷基、烷基芳基和烷基胺基中的烷基与烷基的前述实例相同。在本说明书中,杂芳基胺中的杂芳基可以应用杂环基的前述描述。在本说明书中,芳烯基中的烯基与烯基的前述实例相同。在本说明书中,可以应用芳基的前述描述,不同之处在于亚芳基为二价基团。在本说明书中,可以应用杂环基的前述描述,不同之处在于亚杂芳基为二价基团。在本说明书中,可以应用芳基或环烷基的前述描述,不同之处在于烃环不是一价基团而是由两个取代基结合而形成。在本说明书中,可以应用杂环基的前述描述,不同之处在于杂环不是一价基团而是由两个取代基结合而形成。
优选地,化学式1由以下化学式1-1、化学式1-2或化学式1-3表示:
[化学式1-1]
[化学式1-2]
[化学式1-3]
优选地,Ar为选自以下的任一者:
其中,
X1至X3为N或CH,条件是X1至X3中的至少一者为N,
Ar1和Ar2各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,
X4和X5为N或CH,条件是X4和X5中的至少一者为N,
Ar3独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,
Y为N(Ar5)、O或S,
Ar4为氢、经取代或未经取代的C6-60芳基、或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,以及
Ar5为经取代或未经取代的C6-60芳基。
优选地,Ar1和Ar2各自独立地为苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、二苯并呋喃基、二苯并噻吩基或9-苯基-9H-咔唑基。
优选地,Ar3为苯基、联苯基或萘基。
优选地,Ar4为氢、苯基、联苯基或萘基。
优选地,Ar5为苯基。
由化学式1表示的化合物的代表性实例如下:
在本发明的另一个实施方案中,提供了如以下反应方案1或2所示的用于制备由化学式1表示的化合物的方法。
[反应方案1]
[反应方案2]
在反应方案1和2中,L和Ar与以上限定的那些相同,X'为卤素,优选溴或氯。反应方案1和2为Suzuki偶联反应,其优选在钯催化剂和碱的存在下进行,并且用于Suzuki偶联反应的反应性基团可以如本领域中已知的进行修饰。以上制备方法可以在稍后描述的制备例中进一步详细说明。
在本发明的又一个实施方案中,提供了包含由化学式1表示的化合物的有机发光器件。作为实例,提供了有机发光器件,其包括:第一电极;设置成与第一电极相对的第二电极;和设置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层的一个或更多个层包含由化学式1表示的化合物。
本发明的有机发光器件的有机材料层可以具有单层结构,或者其可以具有其中堆叠有两个或更多个有机材料层的多层结构。例如,本公开内容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、电子注入层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且其可以包括更少数目的有机层。
此外,有机材料层可以包括发光层,其中发光层包含由化学式1表示的化合物。特别地,根据本发明的化合物可以用作发光层中的掺杂剂。
此外,有机材料层可以包括电子传输层或电子注入层,其中电子传输层或电子注入层包含由化学式1表示的化合物。
此外,电子传输层、电子注入层或者同时进行电子传输和电子注入的层包含由化学式1表示的化合物。
此外,有机材料层包括发光层和电子传输层,其中电子传输层可以包含由化学式1表示的化合物。
此外,根据本发明的有机发光器件可以为其中阳极、一个或更多个有机材料层、和阴极依次堆叠在基底上的正常型有机发光器件。此外,根据本公开内容的有机发光器件可以为其中阴极、一个或更多个有机材料层、和阳极依次堆叠在基底上的倒置型有机发光器件。例如,图1和图2示出了根据本公开内容的实施方案的有机发光器件的结构。
图1示出了包括基底1、阳极2、有机材料层3和阴极4的有机发光器件的实例。在这样的结构中,由化学式1表示的化合物可以包含在有机材料层中。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层7、发光层8、空穴阻挡层9、电子传输层10、电子注入层11和阴极4的有机发光器件的实例。在这样的结构中,由化学式1表示的化合物可以包含在空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层和电子注入层中的一个或更多个层中。
根据本发明的有机发光器件可以通过本领域已知的材料和方法来制造,不同之处在于有机材料层的一个或更多个层包含由化学式1表示的化合物。此外,当有机发光器件包括复数个有机材料层时,有机材料层可以由相同材料或不同材料形成。
例如,根据本发明的有机发光器件可以通过在基底上依次堆叠第一电极、有机材料层和第二电极来制造。在这种情况下,有机发光器件可以通过如下来制造:使用PVD(物理气相沉积)法例如溅射法或电子束蒸镀法在基底上沉积金属、具有导电性的金属氧化物、或其合金以形成阳极,在阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后在有机材料层上沉积可以用作阴极的材料。除了这样的方法之外,有机发光器件还可以通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制造。
此外,在制造有机发光器件时,由化学式1表示的化合物可以通过溶液涂覆法以及真空沉积法形成为有机层。在本文中,溶液涂覆法意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷洒法、辊涂等,但不限于此。
除了这样的方法之外,有机发光器件还可以通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制造(国际公开WO 2003/012890)。然而,制造方法不限于此。
作为实例,第一电极为阳极,第二电极为阴极,或者替代地,第一电极为阴极,第二电极为阳极。
作为阳极材料,通常优选使用具有大功函数的材料,使得空穴可以顺利地注入有机材料层。阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(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;等等,但不限于此。
作为阴极材料,通常优选使用具有小功函数的材料,使得电子可以容易地注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al;等等,但不限于此。
空穴注入层是用于注入来自电极的空穴的层,空穴注入材料优选为这样的化合物:其具有传输空穴的能力,因此具有注入阳极中的空穴的效应和优异的对发光层或发光材料的空穴注入效应,防止发光层中产生的激子移动至空穴注入层或电子注入材料,并且具有优异的薄膜形成能力。优选地,空穴注入材料的HOMO(最高占据分子轨道)在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于的有机材料、蒽醌、基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此。
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。空穴传输材料适当地为具有大的空穴迁移率的材料,其可以接收来自阳极或空穴注入层的空穴并将空穴传输至发光层。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时存在共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光材料优选为这样的材料:其可以接收分别从空穴传输层和电子传输层传输的空穴和电子,并使空穴和电子结合以发出可见光区域内的光,并且对荧光或磷光具有良好的量子效率。发光材料的具体实例包括:8-羟基-喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、苯并噻唑和苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层可以包含主体材料和掺杂剂材料。主体材料可以为稠合芳族环衍生物、含杂环的化合物等。稠合芳族环衍生物的具体实例包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等。含杂环的化合物的实例包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,但不限于此。
掺杂剂材料的实例包括芳族胺衍生物、苯乙烯胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物为经取代或未经取代的具有芳基氨基的稠合芳族环衍生物,并且其实例包括具有芳基氨基的芘、蒽、二茚并芘等。苯乙烯胺化合物为其中经取代或未经取代的芳基胺中取代有至少一个芳基乙烯基的化合物,其中选自芳基、甲硅烷基、烷基、环烷基和芳基氨基的一个或两个或更多个取代基是经取代或未经取代的。其具体实例包括苯乙烯胺、苯乙烯二胺、苯乙烯三胺、苯乙烯四胺等,但不限于此。此外,金属配合物包括铱配合物、铂配合物等,但不限于此。
电子传输层是接收来自电子注入层的电子并将电子传输至发光层的层,并且电子传输材料适当地为这样的材料:其可以很好地接收来自阴极的电子并将电子传输至发光层,并且具有大的电子迁移率。电子传输材料的具体实例包括: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-金属配合物等,但不限于此。电子传输层可以与如根据相关技术使用的任何期望的阴极材料一起使用。特别地,阴极材料的适当实例为具有低功函数,后接铝层或银层的常见材料。其具体实例包括铯、钡、钙、镱和钐,在每种情况下后接铝层或银层。
电子注入层是注入来自电极的电子的层,并且优选为这样的化合物:其具有传输电子的能力,具有注入来自阴极的电子的效应和将电子注入发光层或发光材料的优异效应,防止由发光层产生的激子移动至空穴注入层,并且还具有优异的薄膜形成能力。电子注入层的具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物化合物,含氮5-元环衍生物等,但不限于此。
金属配合物化合物的实例包括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,但不限于此。
根据使用的材料,根据本发明的有机发光器件可以为前侧发射型、后侧发射型或双侧发射型。
此外,除了有机发光器件之外,由化学式1表示的化合物还可以包含在有机太阳能电池或有机晶体管中。
将在以下实施例中详细地描述由化学式1表示的化合物和包含其的有机发光器件的制备。然而,呈现这些实施例仅用于举例说明目的,并且不旨在限制本发明的范围。
[实施例]
实施例1:化合物1的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A(7.50g,20.05mmol)和化合物a-1(7.43g,21.06mmol)完全溶解在四氢呋喃(240mL)中,向其中添加2M碳酸钾水溶液(120mL)并添加四-(三苯基膦)钯(0.70g,0.60mmol),然后将所得混合物加热并搅拌4小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用四氢呋喃(180mL)重结晶以制备化合物1(8.76g,产率:67%)。
MS:[M+H]+=648
实施例2:化合物2的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A(6.50g,17.38mmol)和化合物a-2(6.44g,18.25mmol)完全溶解在四氢呋喃(260mL)中,向其中添加2M碳酸钾水溶液(130mL)并添加四-(三苯基膦)钯(0.60g,0.52mmol),然后将所得混合物加热并搅拌3小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(270mL)重结晶以制备化合物2(7.46g,产率:66%)。
MS:[M+H]+=648
实施例3:化合物3的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A(8.50g,22.73mmol)和化合物a-3(8.42g,23.86mmol)完全溶解在四氢呋喃(240mL)中,向其中添加2M碳酸钾水溶液(120mL)并添加四-(三苯基膦)钯(0.79g,0.68mmol),然后将所得混合物加热并搅拌2小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(210mL)重结晶以制备化合物3(7.89g,产率:54%)。
MS:[M+H]+=647
实施例4:化合物4的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A(7.50g,20.05mmol)和化合物a-4(9.03g,21.06mmol)完全溶解在四氢呋喃(220mL)中,向其中添加2M碳酸钾水溶液(110mL)并添加四-(三苯基膦)钯(0.70g,0.60mmol),然后将所得混合物加热并搅拌5小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(320mL)重结晶以制备化合物4(9.11g,产率:63%)。
MS:[M+H]+=724
实施例5:化合物5的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A-1(15.58g,33.43mmol)和化合物a-5(8.50g,31.84mmol)完全溶解在四氢呋喃(240mL)中,向其中添加2M碳酸钾水溶液(120mL)并添加四-(三苯基膦)钯(1.10g,0.96mmol),然后将所得混合物加热并搅拌4小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(280mL)重结晶以制备化合物5(11.24g,产率:62%)。
MS:[M+H]+=572
实施例6:化合物6的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A-1(12.13g,26.02mmol)和化合物a-6(8.50g,24.78mmol)完全溶解在四氢呋喃(260mL)中,向其中添加2M碳酸钾水溶液(130mL)并添加四-(三苯基膦)钯(0.86g,0.74mmol),然后将所得混合物加热并搅拌5小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(270mL)重结晶以制备化合物6(10.67g,产率:66%)。
MS:[M+H]+=648
实施例7:化合物7的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物A-1(10.28g,22.06mmol)和化合物a-7(7.50g,21.01mmol)完全溶解在四氢呋喃(280mL)中,向其中添加2M碳酸钾水溶液(140mL)并添加四-(三苯基膦)钯(0.73g,0.63mmol),然后将所得混合物加热并搅拌5小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(310mL)重结晶以制备化合物7(8.84g,产率:64%)。
MS:[M+H]+=662
实施例8:化合物8的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物B(8.50g,23.81mmol)和化合物a-1(11.65g,25.01mmol)完全溶解在四氢呋喃(280mL)中,向其中添加2M碳酸钾水溶液(140mL)并添加四-(三苯基膦)钯(0.83g,0.71mmol),然后将所得混合物加热并搅拌4小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(280mL)重结晶以制备化合物8(10.22g,产率:65%)。
MS:[M+H]+=648
实施例9:化合物9的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物B-1(10.70g,22.96mmol)和化合物a-6(7.50g,21.87mmol)完全溶解在四氢呋喃(180mL)中,向其中添加2M碳酸钾水溶液(90mL)并添加四-(三苯基膦)钯(0.76g,0.66mmol),然后将所得混合物加热并搅拌4小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(280mL)重结晶以制备化合物9(8.71g,产率:60%)。
MS:[M+H]+=650
实施例10:化合物10的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物C(9.50g,22.73mmol)和化合物a-8(9.62g,23.86mmol)完全溶解在四氢呋喃(260mL)中,向其中添加2M碳酸钾水溶液(130mL)并添加四-(三苯基膦)钯(0.79g,0.68mmol),然后将所得混合物加热并搅拌4小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(240mL)重结晶以制备化合物10(9.82g,产率:62%)。
MS:[M+H]+=698
实施例11:化合物11的制备
在氮气气氛下,在500mL圆底烧瓶中,将化合物C-1(8.51g,21.11mmol)和化合物a-9(4.63g,9.91mmol)完全溶解在四氢呋喃(260mL)中,向其中添加2M碳酸钾水溶液(130mL)并添加四-(三苯基膦)钯(0.70g,0.60mmol),然后将所得混合物加热并搅拌5小时。将温度降至常温,除去水层,将所得产物用无水硫酸镁干燥,然后在减压下浓缩,用乙酸乙酯(310mL)重结晶以制备化合物11(7.85g,产率:58%)。
MS:[M+H]+=678
[实验例]
实验例1
将其上涂覆有厚度为的ITO(氧化铟锡)作为薄膜的玻璃基底放入其中溶解有清洁剂的蒸馏水中,并进行超声波清洗。在这种情况下,使用由Fischer Co.制造的产品作为清洁剂,并使用利用由Millipore Co.制造的过滤器过滤两次的蒸馏水作为蒸馏水。在将ITO清洗30分钟之后,使用蒸馏水重复进行两次超声波清洗10分钟。在用蒸馏水清洗完成之后,将基底用异丙醇、丙酮和甲醇溶剂超声波清洗,然后干燥,然后转移至等离子体清洗器。此外,将基底使用氧等离子体清洗5分钟,然后转移至真空沉积器。
在由此准备的作为阳极电极的ITO透明电极上,将以下化合物HI1和以下化合物HI2以98:2的比率(摩尔比)热真空沉积至具有的厚度,从而形成空穴注入层。将以下化合物HT1真空沉积在空穴注入层上至的厚度以形成空穴传输层。将以下化合物EB1真空沉积在空穴传输层上至的厚度以形成电子阻挡层。然后,将以下化合物BH和以下化合物BD以25:1的重量比真空沉积在电子阻挡层上至的厚度以形成发光层。将以上实施例1中制备的化合物1真空沉积在发光层上至的厚度以形成空穴阻挡层。将以下化合物ET1和以下化合物LiQ以1:1的比率真空沉积在空穴阻挡层上至的厚度以形成电子注入和传输层。将氟化锂(LiF)和铝依次沉积在电子注入和传输层上至分别具有和的厚度,从而形成阴极。
实验例2至11
以与实施例1中相同的方式制造有机发光器件,不同之处在于使用下表1中所示的化合物代替化合物1。
比较实验例1至3
以与实施例1中相同的方式制造有机发光器件,不同之处在于使用下表1中所示的化合物代替化合物1。下表1中所示的化合物HB1、HB2和HB3如下:
通过向实验例和比较实验例中制造的有机发光器件施加电流来测量电压、效率、色坐标和寿命,结果示于下表1中。此时,T95意指亮度降低至初始亮度(1600尼特)的95%所需的时间。
[表1]
如表1所示,使用本发明的化合物作为电子阻挡层的有机发光器件在有机发光器件的效率、驱动电压和稳定性方面表现出优异的特性。特别地,与使用其中三嗪取代基连接至9,9'-螺二[氟](9,9'-spirobi[fluorine])和9,9-二苯基-9H-芴核的化合物HB2和HB3制造的比较实验例2和3的有机发光器件相比,使用本发明的化合物的实验例1至11的有机发光器件表现出低电压、高效率和长寿命特性。此外,使用具有其中基于胺的取代基取代本发明的核的结构的化合物HB-1制造的比较实验例1的有机发光器件没有表现出这些特性。
[附图标记说明]
1:基底 2:阳极
3:有机材料层 4:阴极
5:空穴注入层 6:空穴传输层
7:电子阻挡层 8:发光层
9:空穴阻挡层 10:电子传输层
11:电子注入层
Claims (10)
3.根据权利要求1所述的化合物,
其中L为单键、亚苯基或咔唑二基。
4.根据权利要求1所述的化合物,
其中Ar为选自以下的任一者:
其中,
X1至X3为N或CH,条件是X1至X3中的至少一者为N,
Ar1和Ar2各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,
X4和X5为N或CH,条件是X4和X5中的至少一者为N,
Ar3独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,
Y为N(Ar5)、O或S,
Ar4为氢、经取代或未经取代的C6-60芳基、或者经取代或未经取代的包含选自N、O和S的至少一者的C2-60杂芳基,以及
Ar5为经取代或未经取代的C6-60芳基。
5.根据权利要求4所述的化合物,
其中Ar1和Ar2各自独立地为苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、二苯并呋喃基、二苯并噻吩基或9-苯基-9H-咔唑基。
6.根据权利要求4所述的化合物,
其中Ar3为苯基、联苯基或萘基。
7.根据权利要求4所述的化合物,
其中Ar4为氢、苯基、联苯基或萘基。
8.根据权利要求4所述的化合物,
其中Ar5为苯基。
10.一种有机发光器件,包括:第一电极;设置成与所述第一电极相对的第二电极;和设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层中的一个或更多个层包含根据权利要求1至9中任一项所述的化合物。
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