CN114133408A - Boron-based compound and application thereof in organic electroluminescent device - Google Patents
Boron-based compound and application thereof in organic electroluminescent device Download PDFInfo
- Publication number
- CN114133408A CN114133408A CN202111442502.6A CN202111442502A CN114133408A CN 114133408 A CN114133408 A CN 114133408A CN 202111442502 A CN202111442502 A CN 202111442502A CN 114133408 A CN114133408 A CN 114133408A
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- Prior art keywords
- boron
- based compound
- group
- compound
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 109
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- -1 nitro, cyano, methyl Chemical group 0.000 claims description 21
- 239000010410 layer Substances 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical group C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 4
- 238000010791 quenching Methods 0.000 abstract description 4
- 230000000171 quenching effect Effects 0.000 abstract description 4
- 230000007704 transition Effects 0.000 abstract description 4
- 230000005281 excited state Effects 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical group OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 abstract description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract 1
- 230000021615 conjugation Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 241001025261 Neoraja caerulea Species 0.000 description 2
- 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 2
- 230000000903 blocking effect Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TUGCZKRJXJFPAU-UHFFFAOYSA-N 10-(4-methylphenyl)-5H-phenazine Chemical compound CC(C=C1)=CC=C1N1C(C=CC=C2)=C2NC2=CC=CC=C12 TUGCZKRJXJFPAU-UHFFFAOYSA-N 0.000 description 1
- YUQMVYGPBWMRCM-UHFFFAOYSA-N 10-(4-phenylphenyl)-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1 YUQMVYGPBWMRCM-UHFFFAOYSA-N 0.000 description 1
- JGGSOWGJMBNDHS-UHFFFAOYSA-N 10-phenyl-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C1=CC=CC=C1 JGGSOWGJMBNDHS-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- YVJCHMOUBZDWTD-UHFFFAOYSA-N 10h-phenothiazine Chemical compound C1=CC=C2NC3=C=CC=C[C]3SC2=C1 YVJCHMOUBZDWTD-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- UOCIAGACPIFTCN-UHFFFAOYSA-N 2-chloro-10-phenylphenothiazine Chemical compound C12=CC(Cl)=CC=C2SC2=CC=CC=C2N1C1=CC=CC=C1 UOCIAGACPIFTCN-UHFFFAOYSA-N 0.000 description 1
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- BPTBBSRWJRBIRU-UHFFFAOYSA-N 9,9-dimethyl-2-phenyl-10H-acridine Chemical compound CC1(C)C2=CC(=CC=C2NC2=C1C=CC=C2)C1=CC=CC=C1 BPTBBSRWJRBIRU-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 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
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- YBGHXHSQISJNDM-UHFFFAOYSA-N n,n-diphenyl-9h-carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3NC2=CC=1)C1=CC=CC=C1 YBGHXHSQISJNDM-UHFFFAOYSA-N 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002988 phenazines Chemical group 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a boron-based compound and application thereof in an organic electroluminescent device, belonging to the technical field of photoelectric materials. According to the compound, a main body is formed by nitrogen bonding of dibenzo-six-membered heterocyclic rings and dibenzo-six-membered heterocyclic groups such as carbazole, acridine and phenazine, boron group modification is performed on the center of the main body, the main body with high rigidity and large conjugation is matched with the boron group of a weak receptor, the relaxation of excited state vibration of the compound molecule is reduced, the radiation transition rate of a carrier is improved, in addition, annihilation or quenching of intermolecular excitons is reduced by substituting the main body with substituents such as phenyl and tert-butyl, and the light-emitting efficiency and the service life of a device prepared by using the compound as a light-emitting layer guest material are remarkably improved.
Description
Technical Field
The invention relates to the field of photoelectric materials, in particular to a boron-based compound and application thereof in an organic electroluminescent device.
Background
Compared with Liquid Crystal Display (LCD), the Organic Light Emitting Diode (OLED) has the advantages of self-luminescence, wide viewing angle, high response speed, lightness, thinness, low temperature resistance, flexible display, double-transparent display and the like, has bright industrial prospect, and in the industrialization process, the performance of the light emitting material directly influences the efficiency, the service life and other performances of the device, and becomes an important factor influencing the rapid development of the OLED.
In recent years, a novel pi-conjugated organic unit material containing organic boron and nitrogen co-insertion has become a research hotspot of a blue-light OLED material system due to good photophysical and electrochemical properties. However, due to its wide band gap, the blue light material has difficulty and instability in the carrier transfer and energy transfer processes in the electroluminescence process, and in particular, at high current density, the roll off of device efficiency is very serious due to singlet-triplet annihilation (STA), triplet-triplet annihilation (TTA), triplet-polaron annihilation (TPQ), non-radiative decay caused by excited molecular vibrational relaxation, and the like. So far, no organic boron semiconductor luminescent material has the performance capable of meeting the industrial requirements in the blue light field.
Disclosure of Invention
The application aims to provide a boron-based compound and application thereof in an organic electroluminescent device so as to improve the efficiency roll-off phenomenon of the existing blue-ray device, improve the comprehensive performances of the blue-ray device such as luminous efficiency, service life and the like, and accelerate the commercial application process of boron-based.
The first aspect of the present invention provides a boron-based compound, wherein the structural general formula of the compound is shown as formula 1:
wherein, X1、X2Are each independently O, S, N (R)6) And C (R)7)(R8) Any one of the above;
a is 0 or 1, and when a is 0, X2The bridged 2 aromatic carbon sites are directly connected through a single bond;
R1-R5is one or more substituents satisfying the number of benzene ring valence bonds, each independentlySelected from hydrogen, fluoro, nitro, cyano, C1-20Alkyl of (C)1-20Alkoxy group of (C)3-20Cycloalkyl of, C3-20Heterocycloalkyl of (A), C6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R6–R8are the same or different from each other and are each independently selected from C1-12Alkyl and C6-30Any one of the aryl groups of (1).
Further, the boron-based compound is represented by formula 1-1 or formula 1-2:
wherein the symbols and indices used have the meanings given in claim 1.
Further, R7And R8The same as each other, are each methyl.
Further, R6Selected from any one of: a phenyl group substituted or unsubstituted by one substituent, a biphenyl group substituted or unsubstituted by one substituent, a terphenyl group substituted or unsubstituted by one substituent and a naphthyl group substituted or unsubstituted by one substituent, wherein the substituents are each independently any one selected from the group consisting of a fluoro group, a nitro group, a cyano group, a methyl group and a tert-butyl group.
Further, R1Is a substituent group which satisfies the number of benzene ring valence bonds, and is independently selected from any one of hydrogen, fluoro, methyl, tert-butyl and phenyl.
Further, R2–R5Is one or more substituents satisfying the number of benzene ring valence bonds, and is/are respectively and independently selected from any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, a group shown as a1, a group shown as a2, a group shown as A3 and a group shown as a 4:
wherein R is9-R13Is one or more substituents satisfying the number of benzene ring valences, selected from: any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl and phenyl.
Further, the boron-based compound represented by formula 1 is selected from any one of the following structural formulas:
in a second aspect, the present invention provides an organic electroluminescent device mainly comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising any one of the boron-based compounds described above.
Further, the organic layer between the two electrodes includes a light-emitting layer composed of a light-emitting host and a light-emitting guest, and the light-emitting guest includes any one of the above-described boron-based compounds.
The boron-based compound provided by the invention is subjected to boron-based modification on the main body which is formed by bonding the dibenzo-hexatomic heterocycle with the nitrogen of the dibenzo-hexatomic heterocycle groups such as carbazoles and phenazines to form rigid large conjugate, and because the boron-containing material is weak in charge, the compound molecules have wider band gaps, and meanwhile, the compound molecules become strong in rigidity and weaken non-radiative transition caused by excited state vibration relaxation, so that the compound shows excellent blue light emission, and the more rigid structure can also increase the carrier radiative transition rate, improve the luminous efficiency and simultaneously provide better thermodynamic stability. In addition, the main body is substituted by the substituent groups such as phenyl, arylamine, tertiary butyl and the like, and the short and small space configuration can effectively reduce the aggregation of compound molecules in a solid state, thereby effectively avoiding the annihilation or quenching of intermolecular excitons and further improving the luminous efficiency. Compared with other organic boron materials in the prior art, the organic electroluminescent material using the compound of the invention as a luminescent object material of an organic electroluminescent device has obvious improvement on starting voltage, luminous efficiency, light color and service life.
Detailed Description
It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
Synthesis example 1: synthesis of Compound (2)
Putting 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine (20mmol,8.92g), 9 h-carbazole (20mmol,3.34g), potassium carbonate (40mmol,5.76g) and 100mL of toluene in a reactor, introducing nitrogen, adding 0.38g (2mmol) of cuprous iodide and 0.72g (4mmol) of phenanthroline, and heating, refluxing and stirring for 8 h. Cooling to room temperature, filtering, distilling the liquid phase under reduced pressure, mixing with the filter cake, and refining with silica gel column chromatography to obtain 8.65g of compound represented by the following chemical formula (2a) with yield of 75%;
dissolving the compound (10mmol,5.77g) represented by the formula (2a) in 50mL of tert-butyl benzene solution in a reactor, cooling the reaction solution to-40 ℃, slowly dropwise adding 32.5mL of 2.5M N-hexane tert-butyl lithium solution under the protection of nitrogen, keeping the temperature and stirring for 0.5-2h, adding boron tribromide (15mmol,3.76g), heating the reaction solution to room temperature and stirring for 0.5-2h, cooling the reaction solution to 0 ℃, adding N, N-diisopropylethylamine (10mmol,1.29g), heating to 120 ℃ for reflux reaction, monitoring the completion of the reaction of a liquid phase, cooling to room temperature, adding acetic acid for quenching reaction, extracting the reaction solution by using a mixture of water and dichloromethane, drying an organic phase magnesium sulfate and concentrating, purifying and separating by using a mixed solvent of 1:10 dichloromethane and petroleum ether in a silica gel column to obtain 1.93g of the compound represented by the following formula (2), the yield is 33%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 584.4902.
Synthesis example 2: synthesis of Compound (4)
The procedure of example 1 was repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine in example 1 with 2- (9 h-carbazol-9-yl) -6-chloro-9, 9-dimethyl-10-phenyl-9, 10-dihydroacridine (20mmol,9.70g), thereby obtaining 8.74g of a compound represented by the following formula (4a) in a yield of 71%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 6.16g of the compound represented by (4a) above to give 2.31g of the compound represented by the following formula (4) in a yield of 37%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 623.5697.
Synthetic example 3: synthesis of Compound (17)
The procedure of example 1 was repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine in example 1 with 3-chloro-9, 9-dimethyl-10- (4' -nitro- [1,1' -biphenyl ] -4-yl) -9, 10-dihydroacridine (20mmol,8.82g), thereby obtaining 8.92g of a compound represented by the following chemical formula (17a) in a yield of 78%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.72g of the compound represented by (17a) above to give 2.03g of the compound represented by the following formula (4) in a yield of 35%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 579.4614.
Synthetic example 4: synthesis of Compound (20)
The procedure of example 1 was repeated except for replacing 10- ([1,1 '-biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine in example 1 with 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-4-phenyl-10 h-phenothiazine (20mmol,9.24g), thereby obtaining 8.65g of a compound represented by the following chemical formula (20a) in a yield of 73%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.93g of the compound represented by (20a) described in example 1 to give 1.92g of the compound represented by the following formula (20) in a yield of 32%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 600.5422.
Synthesis example 5: synthesis of Compound (26)
The same procedures as in example 1 were repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 2-chloro-10-phenyl-10 h-phenothiazine (20mmol,6.20g) and 9 h-carbazole with N, N-diphenyl-9 h-carbazol-3-amine (20mmol,6.69g) in example 1 to obtain 8.51g of a compound represented by the following formula (26a) in a yield of 70%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 6.08g of the compound represented by (26a) above to give 1.85g of the compound represented by the following formula (26) in a yield of 30%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 615.5658.
Synthetic example 6: synthesis of Compound (40)
The procedure of example 1 was repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 2-chloro-5, 10-p-tolyl-5, 10-dihydrophenazine (20mmol,7.94g) and 9 h-carbazole with 3, 6-dimethyl-9 h-carbazole (20mmol,3.91g) in example 1 to obtain 8.22g of a compound represented by the following formula (40a) in a yield of 74%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.56g of the compound represented by (40a) described in this example to give 1.92g of the compound represented by the following formula (40) in a yield of 34%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 563.5085.
Synthetic example 7: synthesis of Compound (42)
The procedure of example 1 was repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 7-tert-butyl) -10- (4- (tert-butyl) phenyl) -2-chloro-10 h-phenoxazine (20mmol,8.12g) and 9 h-carbazole with 9, 9-dimethyl-9, 10-dihydroacridine (20mmol,4.19g) in example 1 to give 8.33g of the compound represented by the following formula (42a) in a yield of 72%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.79g of the compound represented by (42a) described in this example, whereby 2.17g of the compound represented by the following formula (42) was obtained in a yield of 37%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 586.5907.
Synthesis example 8: synthesis of Compound (46)
The same procedures as in example 1 were repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 2-chloro-8- (naphthalen-2-yl) -10 phenyl-10 h-phenothiazine (20mmol,8.72g) and 9 h-carbazole with 10 h-phenothiazine (20mmol,3.99g) in example 1 to obtain 8.14g of a compound represented by the following formula (46a) in a yield of 68%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.99g of the compound represented by (46a) above to give 2.00g of the compound represented by the following formula (46) in a yield of 33%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 606.5713.
Synthetic example 9: synthesis of Compound (53)
The procedure of example 1 was repeated except for replacing 10- ([1,1 '-biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 2-chloro-10-phenyl-10 h-phenoxazine (20mmol,5.88g) and 9 h-carbazole with 5- ([1,1' -biphenyl ] -4-yl) -5, 10-dihydrophenazine (20mmol,6.69g) in example 1 to obtain 8.88g of a compound represented by the following formula (53a) in a yield of 75%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.92g of the compound represented by (53a) above, thereby obtaining 1.86g of the compound represented by the following formula (53) in a yield of 31%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 599.5036.
Synthetic example 10: synthesis of Compound (68)
The procedure of example 1 was repeated except for replacing 10- ([1,1' -biphenyl ] -4-yl) -2-chloro-7-phenyl-10-hydro-phenoxazine with 6-chloro-9, 9-dimethyl-2, 10-diphenyl-9, 10-dihydroacridine (20mmol,7.92g) and 9-hydro-carbazole with 9, 9-dimethyl-2-phenyl-9, 10-dihydroacridine (20mmol,5.71g) in example 1 to give 9.29g of a compound represented by the following formula (68a) in a yield of 72%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 6.45g of the compound represented by (68a) above, thereby obtaining 2.22g of the compound represented by the following formula (68) in a yield of 34%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 652.6440.
Synthetic example 11: synthesis of Compound (74)
The procedure of example 1 was repeated except for replacing 10- ([1,1 '-biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine with 10- ([1,1' -biphenyl ] -4-yl) -3-chloro-9, 9-dimethyl l-9, 10-dihydroacridine (20mmol,7.92g) and 9 h-carbazole with 10-phenyl-5, 10-dihydrophenazine (20mmol,5.17g) in example 1 to give 9.50g of a compound represented by the following chemical formula (74a) in a yield of 77%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 6.17g of the compound represented by (74a) described in this example, whereby 2.25g of the compound represented by the following formula (74) was obtained in a yield of 36%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 625.5887.
Synthetic example 12: synthesis of Compound (76)
The synthesis procedure was the same as in example 1 except for replacing 10- ([1,1 '-biphenyl ] -4-yl) -2-chloro-7-phenyl-10 h-phenoxazine in example 1 with 4,4' - (2-chlorophenoxazine-5, 10-diyl) dicyanobenzene (20mmol,8.38g), and replacing 9 h-carbazole with 10 h-phenoxazine (20mmol,3.66g), whereby 8.37g of the compound represented by the following chemical formula (76a) was obtained in a yield of 74%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (2a) in example 1 with 5.66g of the compound represented by (76a) above to give 1.72g of the compound represented by the following formula (76) in a yield of 30%;
the compound obtained was analyzed and found to have the following results: the mass spectrometer MALDI-TOF-MS (m/z) was 573.4259.
Device example 1
And (3) sequentially ultrasonically cleaning the glass substrate with the 50nm ITO transparent film for 10min by using acetone, isopropanol and deionized water, drying for 2h in vacuum at 105 ℃, then washing for 15min by using UV ozone, and conveying the ITO glass substrate to a vacuum evaporation machine.
Vacuum evaporating molybdenum trioxide (MoO) on the surface of the ITO film3) To form a 10nm thick hole injection layer;
next, on the above hole injection layer, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) was vacuum-evaporated to form a 60nm thick hole transport layer;
next, 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA) was vacuum-evaporated on the above hole transport layer to form an electron blocking layer of 10nm,
next, on the above electron blocking layer, 9, 10-bis (2-naphthyl) Anthracene (ADN) (95 wt% as a light emitting host material) and the compound 2 (5 wt% as a light emitting guest material) prepared in the above synthesis example 1 were co-vacuum evaporated to form a light emitting layer with a thickness of 30 nm;
next, on the above light emitting layer, 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi) was vacuum-evaporated to form an electron transporting layer having a thickness of 30 nm;
next, on the above electron transport layer, lithium fluoride (LiF) was vacuum evaporated to form an electron injection layer with a thickness of 1 nm;
finally, on the electron injection layer, magnesium-silver alloy (Mg/Ag) was vacuum-evaporated to form a cathode of 100 nm.
Device example 2 to device example 12
An organic electroluminescent device was prepared in the same manner as in device example 1, except that the compounds synthesized in synthesis examples 2 to 12 above were respectively used instead of compound 2 prepared in synthesis example 1 above.
Comparative device example 13 to comparative device example 15
An organic electroluminescent device was produced in the same manner as in device example 1, except that the following compounds a-1, a-2 and a-3 were used instead of the compound 2 produced in synthesis example 1, respectively.
The organic electroluminescent devices prepared in the device examples and the device comparative examples were subjected to performance tests, and the results are shown in table 1:
TABLE 1
As can be seen from the data in table 1 above, in the compound formed by nitrogen bonding of the dibenzo-six-membered heterocycle and carbazole or acridine, phenazine and other dibenzo-six-membered heterocycle groups to form a host and performing boron group modification on the center of the host, through the coordination of the rigid large conjugated host and the boron group of the weak acceptor, the relaxation of excited state vibration of the compound molecule is reduced, the carrier radiation transition rate is increased, and in addition, the substitution of the host by substituents such as phenyl, tert-butyl and the like reduces annihilation or quenching of excitons between molecules, so that the roll-off phenomenon of the efficiency of a blue light device prepared by using the compound of the present invention as a light-emitting guest material is improved, and compared with a device prepared by using the existing public compound, the blue light-emitting device shows excellent light-emitting efficiency and service life.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (9)
1. A boron-based compound is characterized in that the structural general formula of the compound is shown as formula 1:
wherein, X1、X2Are each independently O, S, N (R)6) And C (R)7)(R8) Any one of the above;
a is 0 or 1, and when a is 0, X2The bridged 2 aromatic carbon sites are connected through single bonds;
R1-R5is one or more substituents satisfying the number of benzene ring valence bonds, and is respectively and independently selected from hydrogen, fluoro, nitro, cyano and C1-20Alkyl of (C)1-20Alkoxy group of (C)3-20Cycloalkyl of, C3-20Heterocycloalkyl of (A), C6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R6–R8are the same or different from each other and are each independently selected from C1-12Alkyl and C6-30Any one of the aryl groups of (1).
2. The boron-based compound according to claim 1, wherein the boron-based compound is represented by formula 1-1 or formula 1-2:
wherein the symbols and indices used have the meanings given in claim 1.
3. The boron-based compound of claim 2, wherein R is7And R8The same as each other, are each methyl.
4. The boron-based compound of claim 2, wherein R is6Selected from any one of: a phenyl group substituted or unsubstituted by one substituent, a biphenyl group substituted or unsubstituted by one substituent, a terphenyl group substituted or unsubstituted by one substituent and a naphthyl group substituted or unsubstituted by one substituent, wherein the substituents are each independently selected from any one of a fluoro group, a nitro group, a cyano group, a methyl group and a tert-butyl group.
5. The boron-based compound of claim 2, wherein R is1Is a substituent group satisfying the number of benzene ring valence bonds, and is independently selected from any one of hydrogen, fluoro, methyl, tert-butyl and phenyl.
6. The boron-based compound of claim 2, wherein R is2–R5Is one or more substituents satisfying the number of benzene ring valence bonds, and is/are respectively and independently selected from any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, a group shown as a1, a group shown as a2, a group shown as A3 and a group shown as a 4:
wherein R is9-R13Is one satisfying the number of benzene ring valence bondsAnd one or more substituents selected from any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl and phenyl.
7. The boron-based compound of claim 2, wherein the boron-based compound is selected from any one of the following structural formulas:
8. an organic electroluminescent device comprising a cathode, an anode and an organic layer disposed between the cathode and the anode, characterized in that the organic layer comprises the boron-based compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a light-emitting layer composed of a light-emitting host and a light-emitting guest comprising the boron-based compound according to any one of claims 1 to 7.
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