WO2023284103A1 - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
- Publication number
- WO2023284103A1 WO2023284103A1 PCT/CN2021/117910 CN2021117910W WO2023284103A1 WO 2023284103 A1 WO2023284103 A1 WO 2023284103A1 CN 2021117910 W CN2021117910 W CN 2021117910W WO 2023284103 A1 WO2023284103 A1 WO 2023284103A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- ring
- diazapyrenyl
- thiadiazolyl
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- -1 hydrocarbon amine Chemical class 0.000 claims description 232
- 239000010410 layer Substances 0.000 claims description 227
- 239000000463 material Substances 0.000 claims description 158
- 230000005525 hole transport Effects 0.000 claims description 45
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 239000004305 biphenyl Substances 0.000 claims description 21
- 235000010290 biphenyl Nutrition 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 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 18
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 229910052711 selenium Inorganic materials 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 8
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- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 8
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- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 8
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 8
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 8
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
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- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 8
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 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 claims description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
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- DCQJQVFIEFMTTQ-UHFFFAOYSA-M magnesium;1,3-dimethylbenzene-2-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC(C)=[C-]1 DCQJQVFIEFMTTQ-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 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
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- 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
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- APOWHQZHFXGEPV-UHFFFAOYSA-M FCC(C=C1CF)=CC(CF)=C1[Mg+].[Br-] Chemical compound FCC(C=C1CF)=CC(CF)=C1[Mg+].[Br-] APOWHQZHFXGEPV-UHFFFAOYSA-M 0.000 description 1
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- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
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- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
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- 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- XGCTUKUCGUNZDN-UHFFFAOYSA-N [B].O=O Chemical compound [B].O=O XGCTUKUCGUNZDN-UHFFFAOYSA-N 0.000 description 1
- AAKRRFGGZYOTQQ-UHFFFAOYSA-N [B].[B].[N] Chemical compound [B].[B].[N] AAKRRFGGZYOTQQ-UHFFFAOYSA-N 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- YVGPBJXKKGORJD-UHFFFAOYSA-N [B].[N].[O] Chemical compound [B].[N].[O] YVGPBJXKKGORJD-UHFFFAOYSA-N 0.000 description 1
- SJEDZTLEKGOBII-UHFFFAOYSA-N [B].[O].[O] Chemical compound [B].[O].[O] SJEDZTLEKGOBII-UHFFFAOYSA-N 0.000 description 1
- OFJJGSAYWPNTEW-UHFFFAOYSA-M [Br-].C1CCOC1.[Mg+]C1=CC=CC=C1 Chemical compound [Br-].C1CCOC1.[Mg+]C1=CC=CC=C1 OFJJGSAYWPNTEW-UHFFFAOYSA-M 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000005264 aryl amine group Chemical group 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
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 description 1
- UBCJCAPLMBHKPY-UHFFFAOYSA-L magnesium;oxolane;dibromide Chemical compound [Mg+2].[Br-].[Br-].C1CCOC1 UBCJCAPLMBHKPY-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000007704 transition Effects 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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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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 invention relates to an organic compound, in particular to a compound that can be used in an organic electroluminescent device, and to an organic electroluminescent device using the organic compound.
- OLED Organic Light Emission Diodes
- OLED Organic Light Emission Diodes
- OLED Organic Light Emission Diodes
- a sandwich-like structure including positive and negative electrode film layers and an organic functional material layer sandwiched between the electrode film layers. Apply voltage to the electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of the electric field, the positive and negative charges migrate in the organic layer and recombine to emit light. Due to the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility, OLED devices have attracted much attention in the field of new display technology and new lighting technology. At present, this technology has been widely used in the display panels of new lighting fixtures, smart phones and tablet computers, and will further expand to the application field of large-size display products such as TVs. It is a new type of display with fast development and high technical requirements. technology.
- MR-TADF multiple resonance-induced thermally activated delayed fluorescence
- the invention provides a kind of organic compound with the structure shown in formula (1):
- D 1 and D 2 are each independently selected from one of NR 5 , NR 6 , O or S;
- W 1 and W 2 are each independently C, CH or CR 7 ;
- Ring Ar 1 , Ring Ar 2 , Ring Ar 3 and Ring Ar 4 are each independently selected from a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring, wherein the heteroatoms in the heteroaromatic ring group are selected from One or more of Si, Ge, N, P, O, S and Se;
- Ring Ar 3 and R 6 are not connected, or are connected through a CC single bond, or are connected through O, S or Se, or are connected through CR 8 R 9 or NR 10 ;
- the ring Ar 4 and the ring R 5 are not connected, or connected through a CC single bond, or connected through O, S or Se, or connected through CR 8 R 9 or NR 10 ;
- R 6 and W 2 are not connected, or connected through CC single bond, or connected through O, S or Se, or connected through CR 8 R 9 or NR 10 ;
- R 5 and W 1 are not connected, or are connected through a CC single bond, or are connected through O, S or Se, or are connected through CR 8 R 9 or NR 10 ;
- R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkane substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C2-C30 aliphatic chain amino group, substituted or unsubstituted C4-C30 Cyclic aliphatic chain hydrocarbon amine, substituted or unsubstituted C6 ⁇ C30 arylamine, substituted or unsubstituted C3 ⁇ C30 heteroarylamine, substituted or unsubstituted C6 ⁇ C30 aryloxy, substituted or unsubstituted One of substituted C6-C60 aryl, substituted or unsubstituted C6-C60 ary
- n1, n2, n3 and n4 are each independently selected from an integer of 0-10; preferably, n1, n2, n3 and n4 are each independently selected from an integer of 1-5;
- n1 is an integer greater than 1, multiple R1s are the same or different, and multiple R1s can be connected to form a ring;
- n2 is an integer greater than 1, multiple R2s are the same or different, and multiple R2s can be connected to form a ring;
- n3 is an integer greater than 1
- multiple R3s are the same or different, and multiple R3s can be connected to form a ring
- n4 is an integer greater than 1
- multiple R4s are the same or different, and multiple R4s can be connected to form a ring
- R 5 and R 6 are each independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; preferably, the R 5 and R 6 are each independently One of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; more preferably, the R 5 and R 6 are each independently selected from substituted or unsubstituted Any one of a benzene ring, a naphthalene ring, an anthracene ring; most preferably, the R 5 and R 6 are each independently a substituted or unsubstituted benzene ring.
- R 7 is selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl , substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C2-C30 aliphatic chain amino group, substituted or unsubstituted C4-C30 cyclic aliphatic chain amino group, substituted or unsubstituted C6 ⁇ C30 arylamino, substituted or unsubstituted C3 ⁇ C30 heteroarylamino, substituted or unsubstituted C6 ⁇ C30 aryloxy, substituted or unsubstituted C6 ⁇ C60 aryl, substituted or unsubstituted C3 One of ⁇ C60 heteroaryl groups; preferably, the R 7 is selected from deuter
- R 8 , R 9 and R 10 are each independently selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aromatic Alkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C2-C30 aliphatic chain amino group, substituted or unsubstituted C4-C30 cyclic aliphatic chain amino group, substituted or unsubstituted C6 ⁇ C30 arylamino, substituted or unsubstituted C3 ⁇ C30 heteroarylamine, substituted or unsubstituted C6 ⁇ C30 aryloxy, substituted or unsubstituted C6 ⁇ C60 aryl, substituted or unsubstituted One of the C3-C60 heteroaryl groups; preferably, R 8 and R 9 are each independently selected from substituted or un
- each of the substituents is independently selected from halogen , cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy , C6-C30 aryl, substituted or unsubstituted C6-C60 arylboryl, C3-C30 heteroaryl or a combination of both.
- D 1 is NR 5
- D 2 is NR 6
- R 5 and R 6 are the same or different; preferably, R 5 and R 6 are the same.
- the general formula (1) is further preferably the following structural formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1-6) :
- the ring Ar 1 , ring Ar 2 , ring Ar 3 and ring Ar 4 are each independently selected from a C6-C60 aromatic ring or a C3-C30 heteroaromatic ring; more preferably, ring Ar 1 , ring Ar 2 , ring Ar 3 and ring Ar 4 are each independently selected from a C6-C30 aromatic ring or a C3-C20 heteroaromatic ring; more preferably, each of ring Ar 1 , ring Ar 2 , ring Ar 3 and ring Ar 4 independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene; most preferably, the ring Ar 1 , ring Ar 2 , ring Ar 3 and ring Ar 4 are each independently benzene ring.
- R 1 , R 2 , R 3 and R 4 are each independently selected from the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec Butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl , cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthracenyl , phenant
- the R5 and R6 are each independently selected from the following substituting groups: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenanthrenyl, pyrenyl, chrysene, perylene, Fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, diphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, diphenyl Hydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, triindenyl, isotriindenyl, spiroindenyl, spiroisotriindenyl, furyl , Benzofuryl, Isobenzofuryl, Dibenzofuryl, Thienyl,
- R is selected from the following substituting groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethane Base, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenanthryl, pyrenyl, chry
- the R 8 , R 9 and R 10 are each independently selected from the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl Base, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-Ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenylene, pyrene Base, Huo base,
- the "substituted or unsubstituted” group can be substituted with one substituent, or can be substituted with multiple substituents. When there are multiple substituents, they can be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection ranges of the substituents are all as shown above and will not be repeated one by one.
- Ca ⁇ Cb means that the group has a ⁇ b carbon atoms, and unless otherwise specified, generally speaking, the carbon number does not include the carbon number of the substituent.
- each independently means that when there are plural subjects, they may be the same or different from each other.
- halogen examples include fluorine, chlorine, bromine, iodine and the like.
- both aryl and heteroaryl include monocyclic and condensed rings.
- the monocyclic aryl group refers to a molecule containing one or at least two phenyl groups. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, for example, phenyl, Biphenyl, terphenyl, etc.; fused ring aryl refers to molecules containing at least two benzene rings, but the benzene rings are not independent of each other, but share the ring edges to fused with each other, such as naphthalene group, anthracenyl group, etc.; monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group, when the molecule contains a heteroaryl group and other groups (such as aryl group, heteroaryl group, alkyl group, etc.), the heteroaryl group The aryl group and other groups are independent of each other and
- the C6-C60 aryl preferably C6-C30 aryl, preferably the aryl is composed of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl , fluorenyl and its derivatives, fluoranthene, triphenylene, pyrenyl, perylenyl, 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 C3-C60 heteroaryl is preferably a C4-C30 heteroaryl, preferably the heteroaryl is furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isophenyl Furanyl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivatives are preferably 9-phenylcarbazole, 9-naphthyl Carbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
- the aryloxy group in the present specification includes a monovalent group composed of the above-mentioned aryl group, heteroaryl group and oxygen.
- the alkoxy group in the present specification includes a monovalent group composed of the above-mentioned chain alkyl group or cycloalkyl group and oxygen.
- the C6-C60 arylamine groups mentioned in this specification include, for example: phenylamine group, methylphenylamine group, naphthylamine group, anthracenylamine group, phenanthrenylamine group, biphenylamine group Base etc.
- the C6-C60 heteroarylamino mentioned in this specification includes, for example, pyridylamino, pyrimidinylamino, dibenzofurylamino, and the like.
- the compounds described in the general formula (1) of the present invention can preferably be compounds with the following specific structures: C1-1 to C1-135, C2-1 to C2-78, C3-1 to C3-78, C4 -1 to C4-43, C5-1 to C5-43, C6-1 to C6-43, these compounds are representative only:
- the structural characteristics of this type of compound of the present invention are: in the mother nucleus structure as general formula (1), two boron atoms are designed at the 1 and 4 positions of the central benzene ring, and simultaneously at the 2 and 5 positions of the central benzene ring The design introduces two nitrogen atoms, or introduces a combination of nitrogen atoms, oxygen atoms, and sulfur atoms.
- the resonance effect between boron atom and nitrogen atom, or boron atom and oxygen group atom, or boron atom and nitrogen atom and oxygen group atom can be used to realize the separation of HOMO and LUMO, while boron atom and nitrogen, oxygen, sulfur
- the hybrid fused ring unit of atoms has a rigid skeleton structure, which can reduce the degree of relaxation of the excited state structure, thereby achieving a narrow half-peak width.
- the general structural scheme of the compound of the present invention compared with the multiple resonance structural schemes such as nitrogen-boron-nitrogen, oxygen-boron-oxygen, nitrogen-boron-oxygen, boron-nitrogen-boron, etc.
- the structure of the compound of the present invention limits the boron Atoms resonate with nitrogen and oxygen atoms, so they do not have thermally activated delayed fluorescence properties. Therefore, when the compound of the present invention is used as a light-emitting layer material in a sensitized organic electroluminescent device, the lifetime of the excitons in the device can be effectively shortened, thereby reducing the roll-off of the device at high brightness and prolonging the life of the device .
- the preparation process of the compound of the present invention is simple and easy, and the raw materials are readily available, which is suitable for mass production and scale-up.
- the second aspect of the present invention protects the above general formula (1), general formula (1-1), (1-2), (1-3), (1-4), (1-5) and (1) at the same time -6) the application of any one of the compounds shown, the application is as a functional material in an organic electronic device, and the organic electronic device includes: an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film Transistors, organic field-effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.
- the present invention also provides an organic electroluminescent device, including a substrate, including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode,
- the organic layer comprises the above general formula (1), general formula (1-1), (1-2), (1-3), (1-4), (1-5) and (1- 6) any one of the compounds shown.
- an embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layer Including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, and the hole transport layer is formed on the hole injection layer Above, the cathode layer is formed on the electron transport layer, and the light emitting layer is between the hole transport layer and the electron transport layer; wherein, the light emitting layer contains the above formula (1 ) The compound of the general formula of the present invention shown.
- the OLED device prepared by using the compound of the invention has low start-up voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturers for high-performance materials.
- Various chemicals used in the present invention such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate and other basic chemical raw materials are purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. Ltd.
- the mass spectrometer used to determine the following compounds was a ZAB-HS mass spectrometer (manufactured by Micromass, UK).
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-11 (3.61 g, 36% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- MALDI-TOF-MS results Molecular ion peak: 668.41 Elemental analysis results: Theoretical value: C: 86.24%; H: 6.33%; B: 3.23%; N: 4.19%; Experimental value: C: 86.20%; H: 6.34 %; N: 4.22%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-16 (4.49 g, 45% yield, HPLC analysis purity 99%) was obtained as an orange solid.
- MALDI-TOF-MS results Molecular ion peak: 664.41 Elemental analysis results: Theoretical value: C: 86.77%; H: 5.76%; B: 3.25%; N: 4.22%; Experimental value: C: 86.74%; H: 5.75 %; N: 4.21%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-17 (0.89 g, 9% yield, HPLC analysis purity 99%) was obtained as an orange-red solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trifluoromethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- Petroleum ether 1:10), the target compound C1-21 (3.11 g, 21% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- MALDI-TOF-MS results Molecular ion peak: 596.22 Elemental analysis results: Theoretical value: C: 76.53%; H: 4.39%; B: 3.63%; N: 4.70%; S: 10.75%; Experimental value: C: 76.50 %; H: 4.39%; S: 10.72%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.97g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.97g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-38 (2.92 g, 28% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (11.86g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (11.86g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-42 (4.67 g, 35% yield, HPLC analysis purity 99%) was obtained as an orange-yellow solid.
- MALDI-TOF-MS results Molecular ion peak: 888.78 Elemental analysis results: Theoretical value: C: 86.48%; H: 7.94%; B: 2.43%; N: 3.15%; Experimental value: C: 86.51%; H: 7.88 %; N: 3.17%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (11.50g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (11.50g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,6-dimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours. 1:10), the target compound C1-78 (1.88 g, 15% yield, HPLC analysis purity 99%) was obtained as a reddish-brown solid.
- MALDI-TOF-MS results Molecular ion peak: 836.51 Elemental analysis results: Theoretical value: C: 89.01%; H: 5.06%; B: 2.58%; N: 3.35%; Experimental value: C: 88.96%; H: 5.02 %; N: 3.37%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (10.18g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (13.45g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (13.45g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-121 (1.79 g, 12% yield, HPLC analysis purity 99%) was obtained as a dark red solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.19g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.19g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-Diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-129 (1.93 g, 20% yield, HPLC analysis purity 99%) was obtained as an orange-red solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (7.40g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (7.40g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C1-117 (2.93 g, 33% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.06g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.06g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C2-21 (2.67 g, 28% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.93g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (7.64g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (7.64g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.30g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.30g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C4-2 (2.33 g, 30% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.34g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (8.34g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C4-20 (2.36 g, 24% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.54g, 15mmol) at 0°C in tert-butylbenzene (150mL), and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.54g, 15mmol) at
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.96g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.96g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C5-4 (2.36 g, 28% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- MALDI-TOF-MS results Molecular ion peak: 562.48 Elemental analysis results: Theoretical value: C: 81.16%; H: 6.45%; B: 3.84%; O: 2.84%; S: 5.70%; Experimental value: C: 81.15 %; H: 6.42%; S: 5.72%.
- n-butyllithium Under a nitrogen atmosphere, a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.78g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction was completed, the temperature was lowered to -30°C, boron tribromide (7.52 g, 30 mmol) was slowly added, and the temperature was raised to 60°C to continue stirring for 2 hours.
- a pentane solution (12mL, 2.50M, 30mmol) of n-butyllithium was slowly added to a solution of a Br-generation precursor (6.78g, 15mmol) in tert-butylbenzene (150mL) at 0°C, and then the temperature was raised to React at 25°C for 1 hour. After the reaction
- N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the reaction was continued at 130° C. for 12 hours.
- 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL, 1.0M, 30mmol) at room temperature and react for 6 hours.
- ether 1:10), the target compound C6-2 (1.95 g, 23% yield, HPLC analysis purity 99%) was obtained as a yellow solid.
- MALDI-TOF-MS results Molecular ion peak: 565.58 Elemental analysis results: Theoretical value: C: 78.60%; H: 6.24%; B: 3.82%; S: 11.34%; Experimental value: C: 78.55%; H: 6.30 %; S: 11.38%.
- Example number Compound number ⁇ E ST (eV) Width at half maximum (nm) Example 1 Material C1-1 of the present invention 0.38 29
- Example 2 Materials C1-11 of the present invention 0.37 28
- Example 3 Material C1-16 of the present invention 0.35 25
- Example 4 Material C1-17 of the present invention 0.32 twenty three
- Example 5 Material C1-21 of the present invention 0.34 twenty four
- Example 6 Material C1-28 of the present invention 0.39
- Example 7 Material C1-38 of the present invention 0.35 31
- Example 10 Material C1-117 of the present invention 0.35 twenty four
- Example 11 Material C1-121 of the present invention 0.30 25
- Example 12 Material C1-129 of the present invention 0.32 26
- Example 13 Material C2-7 of the present invention 0.38
- Example 14 Material C2-21 of the present invention 0.36 31
- Example 15 Material C2-48 of the present invention 0.36
- Example 16 Material C
- ⁇ Est is the difference between the singlet state energy level and the triplet state energy level.
- the measured sample is prepared by dissolving the compound in toluene at a concentration of 10 -5 mol/L.
- the measured fluorescence spectrum and phosphorescence spectrum The difference between the onset values of .
- the instrument is Edinburg FLS1000 (UK); the half-peak width is the peak width at half of the peak height of the fluorescence spectrum at room temperature, that is, a straight line parallel to the bottom of the peak is made through the midpoint of the peak height, and the straight line intersects the two sides of the peak twice.
- An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes.
- the organic material can be divided into multiple regions.
- the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.
- the material of the anode can be oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof.
- the cathode material can be 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 any combination of them.
- the hole transport region is located between the anode and the light emitting layer.
- 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 may also be a multilayer structure including at least one layer 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/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4 - Styrene sulfonate) (Pani/PSS), aromatic amine derivatives, etc.
- phthalocyanine derivatives such as CuPc
- conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-
- the luminescent layer includes luminescent dyes (that is, dopant) that can emit different wavelength spectra, and can also include a sensitizer (sensitizer) and a host material (Host) at the same time.
- the light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue.
- a plurality of monochromatic light-emitting layers of different colors can be arranged planarly according to the pixel pattern, and can also be stacked together to form a colored light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other.
- the light-emitting layer can also be a single color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
- 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 may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocking layer
- the preparation method of the organic electroluminescent device of the present invention comprises the following steps:
- the evaporation rate is 0.1-0.5nm/s
- the organic light-emitting layer material includes host materials, sensitizers and dyes.
- the evaporation rate and sensitivity of the host materials are adjusted by multi-source co-evaporation.
- the evaporation rate of the chemical agent material and the evaporation rate of the dye make the dye reach the preset doping ratio;
- the electron transport material of the device is vacuum evaporated on the organic light-emitting layer to form an electron transport layer, and the evaporation rate is 0.1-0.5nm/s;
- An embodiment of the present invention also provides a display device, which includes the organic electroluminescent 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 organic electroluminescence device of the present invention will be further introduced through specific examples below.
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-1 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-11 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-16 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-17 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-21 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material of the wide bandgap organic light-emitting layer, Sensitizer is the sensitizer and the doping concentration is 20wt%, C1-28 is the dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material of the wide band gap of the organic light-emitting layer, Sensitizer is the sensitizer and the doping concentration is 20wt%, C1-38 is the dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-42 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-78 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-117 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-121 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C1-129 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C2-7 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C2-21 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C2-48 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C3-7 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C3-37 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C4-2 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C4-20 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material of the wide band gap of the organic light-emitting layer, Sensitizer is the sensitizer and the doping concentration is 20wt%, C5-2 is the dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C5-4 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide band gap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C6-2 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm. This embodiment is 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, this embodiment is 30nm; electron injection layer and cathode material selection LiF (0.5nm) and metal aluminum (150nm).
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material of the wide band gap of the organic light-emitting layer, Sensitizer is the sensitizer and the doping concentration is 20wt%, C1 is the dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this implementation An example is 30nm; the material of the electron transport layer is ET, and the thickness is generally 5-300nm, which is 30nm in this embodiment; LiF (0.5nm) and metal aluminum (150nm) are selected for the electron injection layer and the cathode material.
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C2 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- An example is 30nm; the material of the electron transport layer is ET, and the thickness is generally 5-300nm, which is 30nm in this embodiment; LiF (0.5nm) and metal aluminum (150nm) are selected for the electron injection layer and the cathode material.
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C3 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- An example is 30nm; the material of the electron transport layer is ET, and the thickness is generally 5-300nm, which is 30nm in this embodiment; LiF (0.5nm) and metal aluminum (150nm) are selected for the electron injection layer and the cathode material.
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material of the wide band gap of the organic light-emitting layer, Sensitizer is the sensitizer and the doping concentration is 20wt%, C4 is the dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this implementation An example is 30nm; the material of the electron transport layer is ET, and the thickness is generally 5-300nm, which is 30nm in this embodiment; LiF (0.5nm) and metal aluminum (150nm) are selected for the electron injection layer and the cathode material.
- the anode material is ITO; the material of the hole injection layer is HI, and the general total thickness is 5-30nm, which is 5nm in this embodiment; the material of the hole transport layer is HT, and the total thickness is generally 5-500nm, and this embodiment is 30nm; Host is the host material with a wide bandgap in the organic light-emitting layer, Sensitizer is a sensitizer with a doping concentration of 20wt%, C2 is a dye with a doping concentration of 3wt%, and the thickness of the organic light-emitting layer is generally 1-200nm.
- An example is 30nm; the material of the electron transport layer is ET, and the thickness is generally 5-300nm, which is 30nm in this embodiment; LiF (0.5nm) and metal aluminum (150nm) are selected for the electron injection layer and the cathode material.
- C1-C5 as comparative compounds are compounds in the prior art, and their synthesis methods can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509, etc., and will not be repeated here.
- Examples 1-22 and Comparative Examples 1 and 2 when other materials in the structure of the organic electroluminescent device are the same, the compounds involved in the present invention have very narrow electroluminescent spectra. At the same time, compared with the multiple resonance TADF dye with nitrogen-boron-nitrogen structure in the comparative example, the device prepared by the compound provided by the present invention has a lower turn-on voltage and a greatly improved roll-off. This is mainly because the structure of the compound of the present invention limits the resonance of boron atoms and nitrogen and oxygen atoms, and does not have the property of thermally activated delayed fluorescence.
- the excitons When the compound of the present invention is used as a light-emitting layer material in a sensitized organic electroluminescent device, the excitons will not stay in the triplet state, thereby reducing the roll-off of the device under high brightness and prolonging the life of the device.
- Examples 1-22 and Comparative Examples 3, 4 and 5 when other materials in the structure of the organic electroluminescent device are the same, the compounds involved in the present invention have very narrow electroluminescent spectra. At the same time, compared with the situation in which boron nitrogen or boron oxygen is in the ortho position in the comparative example, the device prepared by the compound provided by the present invention has a lower turn-on voltage, and the efficiency and roll-off are greatly improved.
- novel organic material of the present invention is an organic light-emitting functional material with good performance as a light-emitting object of an organic electroluminescent device, and is expected to be popularized for commercial application.
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Abstract
Description
实施例编号 | 化合物编号 | ΔE ST(eV) | 半峰宽(nm) |
实施例1 | 本发明材料C1-1 | 0.38 | 29 |
实施例2 | 本发明材料C1-11 | 0.37 | 28 |
实施例3 | 本发明材料C1-16 | 0.35 | 25 |
实施例4 | 本发明材料C1-17 | 0.32 | 23 |
实施例5 | 本发明材料C1-21 | 0.34 | 24 |
实施例6 | 本发明材料C1-28 | 0.39 | 32 |
实施例7 | 本发明材料C1-38 | 0.35 | 31 |
实施例8 | 本发明材料C1-42 | 0.32 | 27 |
实施例9 | 本发明材料C1-78 | 0.32 | 30 |
实施例10 | 本发明材料C1-117 | 0.35 | 24 |
实施例11 | 本发明材料C1-121 | 0.30 | 25 |
实施例12 | 本发明材料C1-129 | 0.32 | 26 |
实施例13 | 本发明材料C2-7 | 0.38 | 32 |
实施例14 | 本发明材料C2-21 | 0.36 | 31 |
实施例15 | 本发明材料C2-48 | 0.36 | 30 |
实施例16 | 本发明材料C3-7 | 0.34 | 30 |
实施例17 | 本发明材料C3-37 | 0.40 | 34 |
实施例18 | 本发明材料C4-2 | 0.35 | 26 |
实施例19 | 本发明材料C4-20 | 0.38 | 25 |
实施例20 | 本发明材料C5-2 | 0.36 | 30 |
实施例21 | 本发明材料C5-4 | 0.36 | 29 |
实施例22 | 本发明材料C6-2 | 0.35 | 32 |
Claims (10)
- 一种有机化合物,具有如式(1)所示的结构:其中:D 1与D 2各自独立地选自NR 5、NR 6、O或者S中的一种;W 1与W 2各自独立地为C、CH或者CR 7;环Ar 1、环Ar 2、环Ar 3和环Ar 4各自独立地选自C6~C60的芳环或者C3~C60的杂芳环;环Ar 3与R 6之间不相连接,或者通过C-C单键连接,或者通过O、S或Se连接,或者通过CR 8R 9或NR 10连接;环Ar 4与环R 5之间不相连接,或者通过C-C单键连接,或者通过O、S或Se连接,或者通过CR 8R 9或NR 10连接;R 6与W 2之间不相连接,或者通过C-C单键连接,或者通过O、S或Se连接,或者通过CR 8R 9或NR 10连接;R 5与W 1之间不相连接,或者通过C-C单键连接,或者通过O、S或Se连接,或者通过CR 8R 9或NR 10连接;R 1、R 2、R 3和R 4各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1~C30的链状烷基、取代或未取代的C3~C20的环烷基、取代或未取代的C7~C30的芳烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C2~C30脂肪链烃胺基、取代或未取代的C4~C30环状脂肪链烃胺基、取代或未取代的C6~C30芳基胺基、取代或未取代的C3~C30杂芳基胺基、取代或未取代的C6~C30芳氧基、取代或未取代的C6-C60的芳硼基、取代或未取代的C6~C60芳基、取代或未取代的C3~C60杂芳基中的一种;n1、n2、n3和n4各自独立地选自0-10的整数;当n1为大于1的整数时,多个R 1相同或不同,且多个R 1之间可连接成环;当n2为大于1的整数时,多个R 2相同或不同,且多个R 2之间可连接成环;当n3为大于1的整数时,多个R 3相同或不同,且多个R 3之间可连接成环;当n4为大于1的整数时,多个R 4相同或不同,且多个R 4之间可连接成环;R 5和R 6各自独立地选自取代或未取代的C6~C60芳基、取代或未取代的C3~C60杂芳基中的一种;R 7选自氘、卤素、氰基、取代或未取代的C1~C10的链状烷基、取代或未取代的C3~C10的环烷基、取代或未取代的C7~C30的芳烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C2~C30 脂肪链烃胺基、取代或未取代的C4~C30环状脂肪链烃胺基、取代或未取代的C6~C30芳基胺基、取代或未取代的C3~C30杂芳基胺基、取代或未取代的C6~C30芳氧基、取代或未取代的C6~C60芳基、取代或未取代的C3~C60杂芳基中的一种;R 8、R 9和R 10各自独立地选自取代或未取代的C1~C10的链状烷基、取代或未取代的C3~C10的环烷基、取代或未取代的C7~C30的芳烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C2~C30脂肪链烃胺基、取代或未取代的C4~C30环状脂肪链烃胺基、取代或未取代的C6~C30芳基胺基、取代或未取代的C3~C30杂芳基胺基、取代或未取代的C6~C30芳氧基、取代或未取代的C6~C60芳基、取代或未取代的C3~C60杂芳基中的一种;当上述的R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9和R 10上各自独立存在取代基时,所述取代基各自独立地选自卤素、氰基、C1~C20的链状烷基、C3~C20的环烷基、C1~C10的烷氧基、C6~C30芳基氨基、C3~C30杂芳基氨基、C6~C30芳氧基、C6~C30的芳基、取代或未取代的C6-C60的芳硼基、C3~C30的杂芳基中的一种或者两种的组合。
- 根据权利要求1所述的有机化合物,所述n1、n2、n3和n4各自独立地选自1-5的整数;所述R 5和R 6各自独立地选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的一种;优选的,所述R 5和R 6各自独立地选自取代或未取代的苯环、萘环、蒽环中的任意一种;最优选的,所述R 5和R 6各自独立地为取代或未取代的苯环;所述R 7选自氘、卤素、氰基、C1~C6的链状烷基、取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的一种;优选的,所述R 7选自氘、卤素、氰基、取代或未取代的苯环中的一种;所述R 8、R 9和R 10各自独立地选自取代或未取代的C1~C10的链状烷基、取代或未取代的C7~C30的芳烷基、取代或未取代的C6~C30芳基胺基、取代或未取代的C6~C60芳基、取代或未取代的C3~C60杂芳基中的一种。
- 根据权利要求1所述的有机化合物,式(1)中,所述D 1为NR 5,D 2为NR 6,且R 5和R 6相同或不同;优选的,R 5和R 6相同。
- 根据权利要求1-5中任一所述的有机化合物,所述环Ar 1、环Ar 2、环Ar 3和环Ar 4各自独立地选自C6~C60的芳环或者C3~C30的杂芳环;优选的,环Ar 1、环Ar 2、环Ar 3和环Ar 4各自独立地选自C6~C30的芳环或者C3~C20的杂芳环;更优选的,环Ar 1、环Ar 2、环Ar 3和环Ar 4各自独立地选自苯环、萘环、蒽环、芴环、呋喃或噻吩中的任意一种;最优选的,所述环Ar 1、环Ar 2、环Ar 3和环Ar 4各自独立地为苯环。
- 根据权利要求1-5中任一所述的有机化合物,所述R 1、R 2、R 3和R 4各自独立地选自下述取代基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊 基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、氰基、卤素、苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、窟基、茈基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、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、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、异吲哚基、咔唑基、茚并咔唑基、吡啶基、喹啉基、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、吡唑基、吲唑基、咪唑基、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、嘧啶基、苯并嘧啶基、喹喔啉基、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、吡嗪基、吩嗪基、吩噻嗪基、萘啶基、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、二苯基硼基、二米基硼基、二五氟苯基硼基、二(2,4,6-三异丙基苯基)硼基中的一种,或选自以上两种基团的组合;所述的R 5和R 6各自独立地选自下述取代基团:苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、窟基、茈基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、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、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、异吲哚基、咔唑基、茚并咔唑基、吡啶基、喹啉基、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、吡唑基、吲唑基、咪唑基、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、嘧啶基、苯并嘧啶基、喹喔啉基、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、吡嗪基、吩嗪基、吩噻嗪基、萘啶基、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、苯并噻二唑基中的一种,或选自以上两种基团的组合;所述的R 7选自下述取代基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、氰基、卤素、苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、窟基、茈基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、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、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩 基、吡咯基、异吲哚基、咔唑基、茚并咔唑基、吡啶基、喹啉基、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、吡唑基、吲唑基、咪唑基、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、嘧啶基、苯并嘧啶基、喹喔啉基、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、吡嗪基、吩嗪基、吩噻嗪基、萘啶基、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、苯并噻二唑基中的一种,或选自以上两种基团的组合;所述的R 8、R 9和R 10各自独立地选自下述取代基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、窟基、茈基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、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、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、异吲哚基、咔唑基、茚并咔唑基、吡啶基、喹啉基、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、吡唑基、吲唑基、咪唑基、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、嘧啶基、苯并嘧啶基、喹喔啉基、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、吡嗪基、吩嗪基、吩噻嗪基、萘啶基、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、苯并噻二唑基中的一种,或选自以上两种基团的组合。
- 根据权利要求1-8中任一项所述的化合物的应用,所述应用为在有机电子器件中作为功能材料,所述有机电子器件包括有机电致发光器件、光学传感器、太阳能电池、照明元件、有机薄膜晶体管、有机场效应晶体管、有机薄膜太阳能电池、信息标签、电子人工皮肤片材、片材型扫描器或电子纸;进一步,所述化合物的应用为在有机电致发光器件中用作发光层材料,具体作为发光层中的发光材料。
- 一种有机电致发光器件,包括第一电极、第二电极和插入在所述第一电极和第二电极之间的一个或多个发光功能层,其中所述发光功能层中含有权利要求1-8中任一所述的化合物;进一步,所述的发光功能层包括空穴传输区、发光层、电子传输区,所述的空穴传输区形成在所述的阳极层上,所述的阴极层形成在所述的电子传输区上,所述的空穴传输区与所述的电子传输区之间为发光层;其中,所述发光层中含有权利要求1-8中任一所述的化合物。。
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