WO2023093094A1 - 一种有机电致发光器件及显示装置 - Google Patents
一种有机电致发光器件及显示装置 Download PDFInfo
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- WO2023093094A1 WO2023093094A1 PCT/CN2022/107504 CN2022107504W WO2023093094A1 WO 2023093094 A1 WO2023093094 A1 WO 2023093094A1 CN 2022107504 W CN2022107504 W CN 2022107504W WO 2023093094 A1 WO2023093094 A1 WO 2023093094A1
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- Prior art keywords
- substituted
- deuterated
- biphenyl
- unsubstituted
- tritiated
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- 239000007850 fluorescent dye Substances 0.000 claims abstract description 48
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 158
- -1 spirobifluorenyl Chemical group 0.000 claims description 152
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 235000010290 biphenyl Nutrition 0.000 claims description 77
- 239000004305 biphenyl Substances 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 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 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 229910052722 tritium Inorganic materials 0.000 claims description 22
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000001769 aryl amino group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
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- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
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- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 7
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- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 238000006467 substitution reaction Methods 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
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- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
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- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 3
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- LHPZQVSSZRFSTE-UHFFFAOYSA-N N,N-diphenyladamantan-1-amine Chemical compound C(C(CC(C1)C2)C3)C1CC23N(C1=CC=CC=C1)C1=CC=CC=C1 LHPZQVSSZRFSTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 3
- JULFJTZPJNNMQK-UHFFFAOYSA-N 1,2,3,4,5-pentakis-phenylbenzene Chemical group C1=CC=CC=C1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JULFJTZPJNNMQK-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 98
- 239000000463 material Substances 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229910052774 Proactinium Inorganic materials 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- PPTSBERGOGHCHC-UHFFFAOYSA-N boron lithium Chemical compound [Li].[B] PPTSBERGOGHCHC-UHFFFAOYSA-N 0.000 description 1
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 230000009191 jumping Effects 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 239000011593 sulfur Substances 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
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Definitions
- the present application relates to an organic electroluminescence device and a display device, which belong to the technical field of organic electroluminescence.
- Organic Light Emitting Diode (Organic Light Emitting Diode, referred to as OLED) is a device that is driven by current to achieve the purpose of emitting light. Its main characteristics come from the organic light-emitting layer. When an appropriate voltage is applied, electrons and holes Excitons are combined in the organic light-emitting layer to emit light of different wavelengths according to the characteristics of the organic light-emitting layer.
- the light-emitting layer is composed of host materials and dyes, and the dyes are mostly selected from traditional fluorescent materials and traditional phosphorescent materials.
- the traditional phosphorescent material has high efficiency, it is expensive and has poor stability, while the traditional fluorescent material is cheap but extremely low in efficiency.
- Existing display devices still have problems such as low efficiency and high driving voltage.
- the present application provides an organic electroluminescent device and a display device, which have high luminous efficiency and driving voltage stability.
- the application provides an organic electroluminescent device, which comprises a light-emitting layer, and the light-emitting layer comprises a triplet-triplet annihilation host and a fluorescent dye, wherein the fluorescent dye has the following formula (1) Or the structure shown in formula (2):
- X 1 and X 2 are independently represented as O, S or N(R 1 );
- A represents one of substituted or unsubstituted C 6 -C 60 carbocyclic groups, substituted or unsubstituted C 3 -C 60 heterocyclic groups, and A is substituted
- Substitution in carbocyclyl or substituted heterocyclic group refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group, or a combination of at least two of them, the substituent is independently connected to the aromatic ring or heteroaryl
- the rings are connected to form a ring or not to form a ring;
- Z 1 -Z 10 are independently represented as N or CR, each appearance of R is the same or different, and two adjacent R can be bonded to each other to form a ring;
- R 1 is connected to the adjacent R by a single bond
- R 2 is connected to the adjacent R by a single bond
- R 1 represents substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C One of 2 ⁇ C 30 heteroaryl groups;
- R 2 represents one of substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl;
- R represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 10 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 6 -C 30 arylamino, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted One of the C 2 -C 30 heteroaryl groups;
- R 1 , R 2 , R substituted or unsubstituted in the substituent refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon , C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two, the substituent is independently connected to the aromatic ring Or the heteroaryl rings are linked to form a ring or not linked to form a ring.
- the present application also provides a display device, comprising any one of the organic electroluminescent devices described above.
- the light-emitting layer includes a triplet-triplet-annihilation material and a fluorescent dye with a structure represented by formula (1) or formula (2).
- the triplet-triplet-annihilation material with triplet annihilation effect and lower triplet energy level combined with fluorescent dyes with anti-intersystem jumping can realize the efficient use of excitons in the system and reduce the triplet excitation in the system.
- the concentration of electrons can improve the luminous efficiency and driving voltage of the device, and suppress the efficiency roll-off.
- the fluorescent dye of the present application can effectively inhibit the interaction between molecules of planar multiple resonance compounds, inhibit the Dexter energy transfer between host and guest materials in the light-emitting layer and the influence of intermolecular interactions, and further realize the improvement of device luminous efficiency and driving voltage. improve.
- the application provides an organic electroluminescent device, which comprises a light-emitting layer, and the light-emitting layer comprises a triplet-triplet annihilation host and a fluorescent dye, wherein the fluorescent dye has the following formula (1) Or the structure shown in formula (2):
- X 1 and X 2 are independently represented as O, S or N(R 1 );
- A represents one of substituted or unsubstituted C 6 -C 60 carbocyclic groups, substituted or unsubstituted C 3 -C 60 heterocyclic groups, and A is substituted
- Substitution in carbocyclyl or substituted heterocyclic group refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two of them are substituted, and the substituent is independently connected to the aromatic ring (that is, the aforementioned C 6 ⁇ C 60 carbocyclyl) or heteroaromatic ring (ie, the aforementioned C 3 ⁇ C 60 heterocyclic group) is connected to form a ring or not connected to form a ring;
- Z 1 -Z 10 are independently represented as N or CR, each appearance of R is the same or different, and two adjacent R can be bonded to each other to form a ring;
- R 1 is connected to the adjacent R by a single bond
- R 2 is connected to the adjacent R by a single bond
- R 1 represents substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C One of 2 ⁇ C 30 heteroaryl groups;
- R 2 represents one of substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl;
- R represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 10 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 6 -C 30 arylamino, substituted or unsubstituted C 6 -C 30 aryl, One of substituted or unsubstituted C 2 -C 30 heteroaryl groups;
- R 1 , R 2 , R substituted or unsubstituted in the substituent refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon , C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two, the substituent is independently connected to the aromatic ring Or the heteroaryl rings are linked to form a ring or not linked to form a ring.
- the expression of Ca ⁇ Cb means that the number of carbon atoms of the group is a ⁇ b, unless otherwise specified, generally speaking, the number of carbon atoms does not include the number of carbon atoms of the substituent.
- the expression of chemical elements usually includes the concept of isotopes with the same chemical properties, such as the expression "hydrogen”, also includes the concepts of "deuterium” and “tritium” with the same chemical properties, carbon ( C) includes 12 C, 13 C, etc., which will not be repeated here.
- the expression of the ring structure crossed by "—" indicates that the linking site is at any position on the ring structure that can form a bond.
- heteroaryl group in the present application refers to an aromatic ring group containing heteroatoms.
- the so-called heteroatoms usually refer to those selected from N, O, S, P, Si and Se, preferably selected from N, O, S .
- C6-C60 aryl group and C3-C60 heteroaryl group in the present application are aromatic groups satisfying the ⁇ -conjugated system, including single ring and condensed ring.
- the so-called single ring means that the molecule contains at least one phenyl group.
- the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, triple Phenyl, etc.
- fused ring means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing ring edges, such as naphthyl, anthracenyl, phenanthrenyl, etc.
- Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group.
- heteroaryl group and other groups such as aryl, heteroaryl, alkyl, etc.
- the groups are independent of each other and connected by a single bond, for example, pyridine, furan, thiophene, etc.
- fused ring heteroaryl refers to the fusion of at least one phenyl and at least one heteroaryl, or, at least Two kinds of heteroaryl groups are fused, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc. for example.
- the substituted or unsubstituted C6 ⁇ C60 aryl group is preferably a C6 ⁇ C30 aryl group, and the carbon number of the aryl group includes but not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22 , C24, C26, C28, etc., preferably phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenanthrenyl, pyrenyl, sulfenyl, perylene, fluoranthenyl, and Tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, bis Aryl in the group consisting of hydropyrenyl, tetrahydropyr
- biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, P-terphenyl-2-yl, inter-terphenyl-4-yl, inter-terphenyl-3-yl and inter-terphenyl-2-yl; said naphthyl includes 1-naphthyl or 2-naphthyl; Anthracenyl is selected from 1-Anthracenyl, 2-Anthracenyl and 9-Anthracenyl; The fluorenyl is selected from 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl and 9-fluorenyl; said pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; naphthacene is selected
- aromatic ring in the present application, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof, fluoranthene, triphenyl Phenyl, pyrenyl, perylene, A group in the group consisting of base and naphthacene.
- the biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl;
- the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl , p-terphenyl-2-yl, inter-terphenyl-4-yl, inter-terphenyl-3-yl and inter-terphenyl-2-yl;
- the naphthyl includes 1-naphthyl or 2-naphthyl;
- the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl;
- the fluorenyl is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3- In the group consisting of fluorenyl, 4-fluorenyl and 9-fluorenyl;
- the fluorenyl derivatives are selected from the group consisting of 9,
- the substituted or unsubstituted C3 ⁇ C60 heteroaryl is preferably a C3 ⁇ C30 heteroaryl.
- the carbon number of heteroaryl includes but not limited to C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. can be nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, etc.
- heterocycles in the present application include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, diphenyl Thienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivatives are preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolo Carbazole.
- the C3-C60 heteroaryl group in the present application may also be a group formed by connecting or/and condensing the above groups with a single bond.
- alkyl group including the concepts of straight-chain alkyl group and branched-chain alkyl group as well as cycloalkyl group.
- the number of carbons in the alkyl group includes but is not limited to C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc.
- the C1-C30 alkyl group is more preferably a C1-C20 alkyl group, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl group, 2-ethylhexyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, etc., more preferably C1-C10 alkyl group.
- cycloalkyl includes monocycloalkyl and polycycloalkyl, and the number of carbons includes but not limited to C4, C5, C6, C7, C8, C9, etc., for example: cyclopropyl, cyclobutyl base, cyclopentyl, cyclohexyl, cycloheptyl, etc.
- examples of C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy , tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., preferably Methoxy, ethoxy, n-propoxy, isopropoxy, t-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
- examples of C1-C20 silyl groups may be silyl groups substituted by groups listed in the above-mentioned C1-C20 alkyl groups, specifically, methylsilyl, dimethylsilyl Silyl group, trimethylsilyl group, ethylsilyl group, diethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, tert-butyldiphenylsilyl group, etc. group.
- the C6-C60 aryloxy group there can be mentioned groups formed by linking each of the above-mentioned substituted or unsubstituted C6-C60 aryl groups with oxygen.
- groups formed by linking each of the above-mentioned substituted or unsubstituted C6-C60 aryl groups with oxygen for specific examples, please refer to the above-mentioned examples. I won't go into details here.
- halogen examples include fluorine, chlorine, bromine, iodine and the like.
- C6 ⁇ C60 arylamino and C3 ⁇ C60 heteroarylamino it means that one H or two H in amino- NH2 is replaced by the above-mentioned C6 ⁇ C60 aryl or C3 ⁇ C60 heteroaryl The resulting group is substituted by the group.
- the light-emitting layer of the organic electroluminescent device of the present application includes a host material and a fluorescent dye, wherein the host material is a triplet-triplet annihilation material (Tripletthora-triplet annihilation, referred to as: TTA), and the fluorescent dye is formula (1) or formula ( 2) A class of planar multiple resonance compounds with anti-intersystem crossing properties. Specifically, the first excited singlet energy level of the host material is greater than that of the fluorescent dye, and the first excited triplet energy level of the host material is smaller than that of the fluorescent dye.
- TTA triplet-triplet annihilation
- the host material and the fluorescent dye have this energy level relationship, after the organic electroluminescent device is electrically excited, the first excited singlet state excitons of the host material will generate to the first excited singlet state of the lower energy level fluorescent dye. transition, and although the fluorescent dye has the first excited triplet state with a higher energy level, due to its anti-intersystem crossing property, the fluorescent dye will undergo an upconversion process, so its own first excited triplet state excitons, the second excited triplet state The first excited singlet excitons and the first excited singlet excitons from the host material fluoresce by transitioning to the ground state.
- the organic electroluminescent device of the present application can not only effectively utilize triplet excitons, but also have a low concentration of triplet excitons in the system. Therefore, the organic electroluminescent device of the present application has excellent luminous efficiency, and Efficiency roll-off and low drive voltage.
- a carbocyclic group or heterocyclic group represented by A with a large steric hindrance group covering has been introduced into the molecular structures of formula (1) and formula (2), and the large steric hindrance group will not only prevent The luminous color and half-peak width of the mother nucleus have a significant impact, and it can also effectively inhibit the interaction between the molecules of the planar multiple resonance compound, thereby effectively inhibiting the reduction of the luminous efficiency of the compound and the broadening of the spectrum at high concentrations.
- the molecular structures of formulas (1) and (2) can effectively suppress the influence of the host-guest materials in the light-emitting layer, including Dexter energy transfer and intermolecular interactions, which can greatly improve the luminous efficiency of the device and drive
- the voltage is reduced, and the width of the efficiency process window is optimized, which enhances the luminous efficiency and the stability of the driving voltage.
- the chemical synthesis of the fluorescent dyes represented by the formulas (1) and (2) is more feasible, and it is easy to modify a variety of different functions, and further structural adjustments can be made according to different application requirements.
- the fluorescent dye has the following (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (2 The structure shown in any of -1), (2-2) or (2-3):
- Z 1 -Z 10 are independently represented as CR, and the definitions of A, R, R 1 and R 2 are the same as those in formula (1) or formula (2); preferably, R 1 is the same as Adjacent Rs are connected by single bonds, and R2 is connected with adjacent Rs by single bonds.
- A is represented as a substitution such as the following (3-1), (3-2), (3-3), (3-4), (3-5), (3 Any structural group shown in -6), (3-7), (3-8) or (3-9):
- the asterisk in the above structure indicates the site that can be connected, and the connection indicates that it is connected to the mother core and/or is connected with a substituent group; the expression of the ring structure crossed by "—" indicates that the connection site is on the ring structure Any position capable of forming a bond; the dotted line in the above structural formula indicates connection or non-connection;
- A is a substitution in a substituted structural group, which means that it is selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkane Substituted by one or a combination of at least two of C 3 -C 10 cycloalkyl, C 6 -C 30 arylamino, C 6 -C 30 aryl, C 2 -C 30 heteroaryl, the The substituents are independently ring-linked or not linked to the aryl or heteroaryl ring to which they are attached.
- R 3 and R 4 independently represent hydrogen, deuterium, tritium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, silicon, substituted or Unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylamino, substituted or unsubstituted C 6 -C 60 Any one of aryl, substituted or unsubstituted C 2 -C 60 heteroaryl; Z is independently represented as N or CR 5 , each appearance of R 5 is the same or different, and two adjacent R 5 can be mutually Bonded to form a ring; R 5 represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted
- R 3 and R 4 are independently represented as substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 6 - Any one of C 60 aryl, substituted or unsubstituted C 2 -C 60 heteroaryl; preferably, at least one of the above-mentioned R 3 and R 4 is selected from one of the following bulky hindrance groups : terphenyl, triphenyl, quaternyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimer Indenyl, isotriindenyl, spiroindenyl, spiroisotriindenyl, furyl, benzofuryl, isobenz
- R represents hydrogen, deuterium, tritium, fluorine atom, cyano group, methyl group, deuterated methyl group, tritiated methyl group, ethyl group, deuterated ethyl group, tritiated ethyl group, Isopropyl, deuterated isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentyl, cyclohexyl, cyclo Amyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, bisphenyl, deuterated bisphenyl, tritiated bisphenyl, deuterated terphenyl, tritiated terphenyl , terphenyl, naphthyl,
- R is represented by methyl, deuterated methyl, deuterated methyl, ethyl, deuterated ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, deuterated isopropyl, tert-butyl, Deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, Deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolinyl, furyl, thiophene Base, dibenzofuryl, dibenzo
- R2 represents phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl Base, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolinyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, methyl-substituted phenyl, micyl, ethyl Substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert Butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethy
- both Z 9 and Z 10 are CR, and the R is hydrogen, Z 1 -Z 8 are all CR, and the definition of R is the same as The definitions in formula (1) or formula (2) are the same.
- Z 2 and Z 7 are both CR, and R is tert-butyl, Z 1 , Z 3 -Z 6 , Z 8 -Z 10 are all CR, and the R is hydrogen.
- fluorescent dyes of the present application are selected from the following specific structural compounds:
- the present application does not specifically limit the TTA host material in the light-emitting layer.
- the performance of the organic electroluminescent device can be improved more significantly.
- the mass proportion of the fluorescent dye in the light-emitting layer is generally controlled to be 0.1% to 50%.
- Reasonable control of the doping amount of the dye in the light-emitting layer is conducive to further improving the luminous efficiency of the device.
- different host materials and dyes in the light-emitting layer of the organic electroluminescent device of the present application will affect the performance of the device. Therefore, generally speaking, for different host materials and dyes, when the mass proportion of the dye in the light-emitting layer is controlled at 0.5% to 20%, the excellent luminous efficiency of the device can be basically guaranteed.
- the thickness of the light-emitting layer of the organic electroluminescent device of the present application is not particularly limited, and may be consistent with the thickness of the light-emitting layer of existing devices in the field, for example, 10-60 nm.
- the organic electroluminescent device of the present application also includes an anode on one side of the light emitting layer and a cathode on the other side of the light emitting layer, that is, the light emitting layer is located between the cathode and the anode.
- the anode and the cathode can adopt materials commonly used in this field.
- the anode can use oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof;
- the cathode can use magnesium (Mg ), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and other metals or alloys and their any combination between.
- the cathode or anode can be formed by sputtering or depositing on a substrate as a corresponding material, and the substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency.
- TFTs thin film transistors
- the organic electroluminescent device of the present application also includes other auxiliary functional regions that are favorable for carrier injection and recombination.
- the hole-transport region between the anode and the light-emitting layer, and the electron-transport region between the cathode and the light-emitting layer are favorable for carrier injection and recombination.
- the hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
- the hole transport region can also be a multilayer structure including at least two layers of a hole injection layer (HIL), a hole transport layer (HTL) and an electron blocking layer (EBL).
- HIL hole injection layer
- HTL hole transport layer
- EBL electron blocking layer
- the material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodeca Alkylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA ), polyaniline/poly(4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives.
- phthalocyanine derivatives such as CuPc
- conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodeca Alkylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-sty
- the material of the hole transport auxiliary layer is an aromatic amine derivative, it may be one or more of the compounds shown in HT-1 to HT-34.
- a hole injection layer is located between the anode and the hole transport layer.
- the hole injection layer can be a single compound material, or a combination of multiple compounds.
- the hole injection layer can use one or more compounds of the above-mentioned HT-1 to HT-34, or one or more compounds in the following HI1-HI3; HT-1 to HT-34 can also be used One or more compounds of doped with one or more compounds in the following HI1-HI3.
- the electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds.
- the electron transport region can also be a multilayer structure including at least two layers of electron injection layer (EIL), electron transport layer (ETL) and hole blocking layer (HBL).
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocking layer
- the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET73 listed below.
- a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer.
- the hole blocking layer can use, but is not limited to, one or more compounds of the above-mentioned ET-1 to ET-73.
- the electron injection material in the electron injection layer includes any one or a combination of at least two of the following compounds: Liq, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Ag , Yb.
- the light extraction layer (CPL layer) can be evaporated on the cathode of the device to improve the efficiency of the device and adjust the optical microcavity.
- the thickness of each of the above-mentioned layers can adopt the conventional thickness of these layers in the art.
- the present application also provides a preparation method of the organic electroluminescent device, which comprises sequentially depositing an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode on a substrate, and then encapsulating.
- a preparation method of the organic electroluminescent device which comprises sequentially depositing an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode on a substrate, and then encapsulating.
- the method of multi-source co-evaporation is used to adjust the evaporation rate of the host material and the evaporation rate of the fluorescent dye so that the fluorescent dye reaches a preset doping ratio, and the triplet-triplet annihilation material source and
- the luminescent layer is formed by co-evaporating any one of the fluorescent dye sources mentioned above.
- the deposition methods of the anode, the hole transport region, the electron transport region and the cathode are the same as
- the organic electroluminescence device of the present application has the advantages of low driving voltage and high efficiency through the combination of specific materials in the light-emitting layer and the selection of special fluorescent dyes.
- the second aspect of the present application further provides a display device, the display device comprising the organic electroluminescence device as provided above.
- the display device may be a display device such as an OLED display, and any product or component having a display function such as a TV, a digital camera, a mobile phone, a tablet computer, etc. including the display device.
- the display device has the same advantages as that of the above-mentioned organic electroluminescent device over the prior art, which will not be repeated here.
- the hydrogen and Cl atoms between/on X 1 , X 2 , X 3 and X 4 are ortho-positioned using n-butyllithium or tert-butyllithium, etc. Metalization.
- boron tribromide is added to perform lithium-boron metal exchange
- a Bronsted base such as N,N-diisopropylethylamine is added to perform a tandem bora-Fried-Clark Futz reaction (Tandem Bora-Friedel-Crafts Reaction), and the target can be obtained.
- MALDI-TOF-MS results Molecular ion peak: 1271.55 Elemental analysis results: Theoretical value: C, 86.90; H, 7.85; B, 0.85; N, 4.41(%); Experimental value: C, 86.80; H, 7.85; B , 0.85; N, 4.51 (%).
- Synthesis of compound S-13-2 This example is basically the same as the synthesis of compound S-7-2, the difference is that in this example, S-7-1 needs to be replaced by S- 13-1.
- Target compound S-13-2 (10.38g, 92% yield, HPLC analysis purity 99.37%), white solid.
- Synthesis of compound S-52-2 This example is basically the same as the synthesis of compound S-7-2, the difference is that in this example, S-7-1 needs to be replaced by S- 52-1.
- Target compound S-52-2 (10.89 g, 86% yield, HPLC analysis purity 99.53%), white solid.
- fluorescent dyes obtained in this application were also characterized by mass spectrometry (MALDI-TOF-MS molecular ion peak), as shown in Table 1 below.
- organic electroluminescent device of the present application will be further introduced through specific examples below.
- Embodiments 1-29 respectively provide an organic electroluminescence device, and its device structure includes an anode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), and an emission layer (EML) in sequence. , hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), cathode, and light extraction layer (CPL).
- HIL hole injection layer
- HTL hole transport layer
- EBL electron blocking layer
- EIL electron injection layer
- CPL light extraction layer
- the glass plate coated with the ITO/Ag/ITO conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, and baked in a clean environment until completely Water is removed, cleaned with UV light and ozone, and the surface is bombarded with a beam of low-energy cations;
- the hole transport layer HT-24 is vacuum evaporated on the hole injection layer, the evaporation rate is 0.1nm/s, and the total film thickness is 110nm;
- the electron blocking layer EB-1 is vacuum evaporated, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 5nm;
- the luminescent layer includes the host material BFH-4 and the fluorescent dye S-7.
- the dye is evaporated according to the doping ratio of 2%.
- the evaporation rate of the main body is 0.1nm/s, and the evaporation film thickness is 20nm.
- Yb with a thickness of 1nm is vacuum evaporated on the electron transport layer as the electron injection layer;
- the device is a top-emitting structure, including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer from bottom to top.
- a top-emitting structure including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer from bottom to top.
- Example 2 In the organic electroluminescent device provided in Examples 2-29, the specific preparation method is similar to that of Example 1, the difference lies in the specific selection of the host material and fluorescent dye and the mass ratio of the fluorescent dye in the light-emitting layer.
- the relevant characterization of some device fluorescent dyes in the examples is shown in Table 1 below.
- Comparative Example 1-8 provides an organic electroluminescent device, the device structure of which is consistent with that of Example 1-29, and the parameters of the corresponding functional layer are also basically the same as those of Example 1-29, the only difference being that the host material and the dye of the light-emitting layer
- the materials used in the examples are inconsistent or the doping concentration is inconsistent.
- Example 1 BFH-4 S-7, 2% 3.98V 176
- Example 2 BFH-4 S-7, 10% 3.99V 174
- Example 3 BFH-4 S-7, 15% 4.02V 170
- Example 4 BFH-4 S-7, 20% 4.02V 169
- Example 5 BFH-4 S-7, 30% 4.05V 166
- Example 6 BFH-14 S-7, 2% 3.51V 177
- Example 7 BFH-14 S-7, 15% 3.58V 171
- Example 8 BFH-14 S-7, 20% 3.59V 170
- Example 9 BFH-14 S-7, 30% 3.77V 167
- Example 10 BFH-4 S-13, 2% 3.97V 178
- Example 11 BFH-4 S-13, 15% 4.04V 173
- Example 12 BFH-4 S-24, 2% 4.03V 169
- Example 13 BFH-4 S-24, 15% 4.07V 165
- Example 14 BFH-4 S-50, 2% 3.87V 180
- Example 15 BFH-4 S-50, 15% 3.90V 175
- Example 16 BFH-4 S-52, 2% 3.88V 183
- Example 17 BFH-4 S-52, 15% 3.92V 180
- Example 18 BFH-4 S-69, 2% 3.95V 181
- Example 19 BFH-4 S-69, 15% 3.98V 179
- Example 20 BFH-4 S-146, 2% 4.05V 166
- Example 21 BFH-4 S
- the organic electroluminescent devices of Examples 1-29 of the present application by introducing a carbocyclic group or heterocyclic group represented by A covered with a large steric hindrance group into the molecular structure , can effectively reduce the driving voltage and improve the luminous efficiency;
- the organic electroluminescent device using the fluorescent dye shown in formula (1) or formula (2) in Examples 1-29 of the present application has less dependence on the mass ratio of the fluorescent dye, and with With the change of the mass ratio of the fluorescent dye concentration, the fluctuation of the driving voltage and luminous efficiency of the device is not significant; further, it can be seen from Examples 1-5 and Examples 6-9 that when the mass ratio of the fluorescent dye is between 0.5-20%, the performance of the device is more excellent;
- Comparative Examples 1-4 when ref-1 and ref-2 molecules were used as dyes, the device driving voltage and luminous efficiency were not as good as those in the examples, and when the doping concentration of the dye was changed by changing ref1 and ref2 at the same time, the device luminous efficiency and The driving voltages all have large changes; in Comparative Examples 5-8, using other types of non-triplet-triplet quenching host ref-3 and ref-4 molecules, the device driving voltage is significantly improved compared with the examples, and the luminescence The efficiency is reduced, so this application can achieve better device performance by matching a type of triplet-triplet annihilation host, which can meet the current requirements of panel manufacturers for high-performance materials, and has a good application prospect.
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Abstract
Description
主体材料 | 染料及质量占比 | 1000cd/m 2下电压V | BI值(CE/CIEy)@1000cd/m 2 | |
实施例1 | BFH-4 | S-7,2% | 3.98V | 176 |
实施例2 | BFH-4 | S-7,10% | 3.99V | 174 |
实施例3 | BFH-4 | S-7,15% | 4.02V | 170 |
实施例4 | BFH-4 | S-7,20% | 4.02V | 169 |
实施例5 | BFH-4 | S-7,30% | 4.05V | 166 |
实施例6 | BFH-14 | S-7,2% | 3.51V | 177 |
实施例7 | BFH-14 | S-7,15% | 3.58V | 171 |
实施例8 | BFH-14 | S-7,20% | 3.59V | 170 |
实施例9 | BFH-14 | S-7,30% | 3.77V | 167 |
实施例10 | BFH-4 | S-13,2% | 3.97V | 178 |
实施例11 | BFH-4 | S-13,15% | 4.04V | 173 |
实施例12 | BFH-4 | S-24,2% | 4.03V | 169 |
实施例13 | BFH-4 | S-24,15% | 4.07V | 165 |
实施例14 | BFH-4 | S-50,2% | 3.87V | 180 |
实施例15 | BFH-4 | S-50,15% | 3.90V | 175 |
实施例16 | BFH-4 | S-52,2% | 3.88V | 183 |
实施例17 | BFH-4 | S-52,15% | 3.92V | 180 |
实施例18 | BFH-4 | S-69,2% | 3.95V | 181 |
实施例19 | BFH-4 | S-69,15% | 3.98V | 179 |
实施例20 | BFH-4 | S-146,2% | 4.05V | 166 |
实施例21 | BFH-4 | S-146,15% | 4.09V | 162 |
实施例22 | BFH-4 | S-244,2% | 4.06V | 171 |
实施例23 | BFH-4 | S-244,15% | 4.11V | 164 |
实施例24 | BFH-4 | S-252,2% | 4.11V | 170 |
实施例25 | BFH-4 | S-252,15% | 4.13V | 163 |
实施例26 | BFH-21 | S-49,2% | 3.61V | 172 |
实施例27 | BFH-21 | S-58,2% | 3.58V | 176 |
实施例28 | BFH-18 | S-96,2% | 3.99V | 173 |
实施例29 | BFH-18 | S-108,2% | 3.96V | 178 |
对比例1 | BFH-4 | Ref-1 2% | 4.26V | 152 |
对比例2 | BFH-4 | Ref-1 15% | 4.39V | 121 |
对比例3 | BFH-4 | Ref-2 2% | 4.33V | 135 |
对比例4 | BFH-4 | Ref-2 15% | 4.44V | 87 |
对比例5 | Ref-3 | S-7,2% | 4.62V | 103 |
对比例6 | Ref-3 | S-7,15% | 4.67V | 92 |
对比例7 | Ref-4 | S-7,2% | 4.55V | 95 |
对比例8 | Ref-4 | S-7,15% | 4.59V | 83 |
Claims (15)
- 一种有机电致发光器件,包括发光层,所述发光层包括三重态-三重态湮灭型主体和荧光染料,其中所述荧光染料具有如下式(1)或式(2)所示的结构:式(1)中,X 1、X 2分别独立地表示为O、S或N(R 1);式(2)中,X 3、X 4分别独立地表示为B(R 2)或C(=O);式(1)或式(2)中,A表示为取代或未取代的C 6~C 60碳环基、取代或未取代的C 3~C 60杂环基中的一种,A为取代的碳环基或为取代的杂环基中的取代,是指被选自氘、氚、氰基、卤素、C 1~C 10烷基、C 3~C 10环烷基、硅基、C 6~C 30芳胺基、C 6~C 30芳基、C 2~C 30杂芳基中的一种或者至少两种的组合所取代,该取代基独立地与相连接的芳环或杂芳环连接成环或不连接成环;式(1)或式(2)中,Z 1-Z 10分别独立地表示为N或CR,R每次出现相同或不同,相邻的两个R可相互键结成环;R 1与相邻的R之间通过单键连接,R 2与相邻的R之间通过单键连接;R 1表示为取代或未取代的C 1~C 10烷基、取代或未取代的C 3-C 10环烷基、取代或未取代的C 6~C 30芳基、取代或未取代的C 2~C 30杂芳基中的一种;R 2表示为取代或未取代的C 6~C 30芳基、取代或未取代的C 2~C 30杂芳基中的一种;R表示为氢、氘、氚、氰基、卤素、取代或未取代的C 1~C 10烷基、取代或未取代的C 3~C 10环烷基、取代或未取代的C 1~C 10烷氧基、取代或未取代的C 6~C 30芳氧基、取代或未取代的C 6~C 30芳胺基、取代或未取代的C 6~C 30芳基、取代或未取代的C 2~C 30杂芳基中的一种;上述R 1、R 2、R中取代或未取代中的取代,是指被选自氘、氚、氰基、卤素、C 1~C 10烷基、C 3~C 10环烷基、硅基、C 6~C 30芳胺基、C 6~C 30芳基、C 2~C 30杂芳基中的一种或者至少两种的组合所取代,该取代基独立地与相连接的芳环或杂芳环连接成环或不连接成环。
- 根据权利要求2所述的有机电致发光器件,其中,R 1与相邻的R之间通过单键连接,R 2与相邻的R之间通过单键连接。
- 根据权利要求1-3任一项所述的有机电致发光器件,其中,所述A表示为取代的如下述(3-1)、(3-2)、(3-3)、(3-4)、(3-5)、(3-6)、(3-7)、(3-8)或(3-9)中任一所示的结构基团:以上结构中的星号表示可连接的位点,所述连接表示与母核连接和/或连接有取代基团;“—”划过的环结构的表达方式,表示连接位点于该环结构上任意能够成键的位置;以上结构式中的虚线表示为连接或者不连接;所述A为取代的结构基团中的取代,是指被选自氘、氚、氰基、卤素、C 1~C 10烷基、C 3~C 10环烷基、C 6~C 30芳胺基、C 6~C 30芳基、C 2~C 30杂芳基中的一种或者至少两种的组合所取代,该取代基独立地与相连接的芳环或杂芳环连接成环或不连接成环。
- 根据权利要求1-4任一项所述的有机电致发光器件,其中,所述A为如下结构式中的任一种所示:其中,R 3和R 4分别独立地表示为氢、氘、氚、取代或未取代的C 1~C 30烷基、取代或未取代的C 3~C 30环烷基、硅基、取代或未取代的C 1~C 30烷氧基、取代或未取代的C 6~C 60芳氧基、取代或未取代的C 6~C 60芳胺基、取代或未取代的C 6~C 60芳基、取代或未取代的C 2~C 60杂芳基中的任意一种;Z独立地表示为N或CR 5,R 5每次出现相同或不同,相邻的两个R 5可相互键结成环;R 5表示为氢、氘、氚、氰基、卤素、取代或未取代的C 1~C 10烷基、取代或未取代的C 3~C 10环烷基、取代或未取代的C 1~C 10烷氧基、取代或未取代的C 6~C 30芳氧基、取代或未取代的C 6~C 30芳胺基、取代或未取代的C 6~C 30芳基、取代或未取代的C 2~C 30杂芳基中的一种;上述R 3、R 4、R 5中取代或未取代中的取代,是指被选自氘、氚、氰基、卤素、C 1~C 10烷基、C 3~C 10环烷基、硅基、C 6~C 30芳胺基、C 6~C 30芳基、C 2~C 30杂芳基中的一种或者至少两种的组合所取代,该取代基独立地与相连接的芳环或杂芳环连接成环或不连接成环。
- 根据权利要求5所述的有机电致发光器件,其中,所述R 3和R 4分别独立地表示为取代或未取代的C 1~C 30烷基、取代或未取代的C 3-C 30环烷基、取代或未取代的C 6~C 60芳基、取代或未取代的C 2~C 60杂芳基中的任意一种。
- 根据权利要求6所述的有机电致发光器件,其中,所述R 3和R 4中至少有一个选自下述大位阻基团中的一种:三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、二氢芘基、四氢芘基、顺式或反式茚并芴基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、异吲哚基、咔唑基、茚并咔唑基、异喹啉基、吖啶基、菲啶基、苯并-5,6-喹啉基、苯并-6,7-喹啉基、苯并-7,8-喹啉基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、嗯唑基、苯并嗯唑基、萘并嗯唑基、蒽并嗯唑基、菲并嗯唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、苯并哒嗪基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂茈基、吩嗪基、吩噻嗪基、氮杂咔唑基、苯并咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-嗯二唑基、1,2,5_嗯二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、苯并噻二唑基、9,9-二甲基吖啶基、二苯基胺基、金刚烷、氟代苯基、甲基苯基、三甲基苯基、氰基苯基、硅基,或者R 3和R 4中至少有一个选自上述大位阻基团中的两种或两种以上基团的组合。
- 根据权利要求1-7任一项所述的有机电致发光器件,其中,所述R表示为氢、氘、氚、氟原子、氰基、甲基、氘代甲基、氚代甲基、乙基、氘代乙基、氚代乙基、异丙基、氘代异丙基、氚代异丙基、叔丁基、氘代叔丁基、氚代叔丁基、氘代环戊基、氚代环戊基、环己烷基、环戊基、金刚烷基、苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、氘代三联苯基、氚代三联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、喹啉基、呋喃基、噻吩基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、氚代甲基取代的苯基、氚代乙基取代的苯基、氚代异丙基取代的苯基、氚代叔丁基取代的苯基、氚代甲基取代的二联苯基、氚代乙基取代的二联苯基、氚代异丙基取代的二联苯基、氚代叔丁基取代的二联苯基、二苯基胺基、二二联苯基胺基、三苯基氨基中的一种;所述R 1表示为甲基、氘代甲基、氚代甲基、乙基、氘代乙基、氚代乙基、异丙基、氘代异丙基、氚代异丙基、叔丁基、氘代叔丁基、氚代叔丁基、氘代环戊基、氚代环戊基、环戊基、金刚烷基、苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、氘代三联苯基、氚代三联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、喹啉基、呋喃基、噻吩基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、氚代甲基取代的苯基、氚代乙基取代的苯基、氚代异丙基取代的苯基、氚代叔丁基取代的苯基、氚代甲基取代的二联苯基、氚代乙基取代的二联苯基、氚代异丙基取代的二联苯基、氚代叔丁基取代的二联苯基中的一种;所述R 2表示为苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、氘代三联苯基、氚代三联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、甲基取代的苯基、米基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、氚代甲基取代的苯基、氚代乙基取代的苯基、氚代异丙基取代的苯基、氚代叔丁基取代的苯基、氚代甲基 取代的二联苯基、氚代乙基取代的二联苯基、氚代异丙基取代的二联苯基、氚代叔丁基取代的二联苯基中的一种。
- 根据权利要求8所述的有机电致发光器件,其中,式(1)或式(2)中,所述Z 9和Z 10均为CH。
- 根据权利要求8所述的有机电致发光器件,其中,式(1)或式(2)中,所述Z 2和Z 7均为CC(CH 3) 3,Z 1、Z 3-Z 6、Z 8-Z 10均为CH。
- 根据权利要求1-12任一项所述的有机电致发光器件,其中,所述荧光染料占发光层的质量比例为0.1%-50%。
- 根据权利要求13所述的有机电致发光器件,其中,所述荧光染料占发光层的质量比例为0.5%-20%。
- 一种显示装置,包括权利要求1-14任一所述的有机电致发光器件。
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