CN107216347A - A kind of boron azepine derivatives for organic electroluminescent - Google Patents
A kind of boron azepine derivatives for organic electroluminescent Download PDFInfo
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- CN107216347A CN107216347A CN201610160951.4A CN201610160951A CN107216347A CN 107216347 A CN107216347 A CN 107216347A CN 201610160951 A CN201610160951 A CN 201610160951A CN 107216347 A CN107216347 A CN 107216347A
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- CYMHIEKFNUNIBB-UHFFFAOYSA-N N1C=CC=CC=C1.[B] Chemical class N1C=CC=CC=C1.[B] CYMHIEKFNUNIBB-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 85
- 239000000463 material Substances 0.000 claims abstract description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 238000002347 injection Methods 0.000 claims abstract description 5
- 239000007924 injection Substances 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 150000001721 carbon Chemical group 0.000 claims description 27
- 238000006467 substitution reaction Methods 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- -1 heterocycle aryl amine Chemical class 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 150000003384 small molecules Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RQQDJYROSYLPPK-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 Chemical class N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 RQQDJYROSYLPPK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal 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
- 230000000171 quenching effect Effects 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- 150000004818 1,2-dichlorobenzenes Chemical class 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GWJSQKNYHPYZRN-UHFFFAOYSA-N 2-methylpropane-2-sulfonamide Chemical compound CC(C)(C)S(N)(=O)=O GWJSQKNYHPYZRN-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- LEMABCWCFKCYQC-UHFFFAOYSA-N OBO.C1=CC=CC2=CC=CC=C21 Chemical class OBO.C1=CC=CC2=CC=CC=C21 LEMABCWCFKCYQC-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NCQDQONETMHUMY-UHFFFAOYSA-N dichloro(phenyl)borane Chemical compound ClB(Cl)C1=CC=CC=C1 NCQDQONETMHUMY-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000005059 solid analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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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
- 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
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- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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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
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—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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- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Optics & Photonics (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a kind of boron azepine derivatives for organic electroluminescent, it is characterised in that its structure is as shown in logical formula (I)：
Description
Technical field
Derive the present invention relates to a kind of boron azepine derivatives, more particularly to a kind of boron nitrogen for organic electroluminescent
Thing.
Background technology
Organic electroluminescent (OLED), is described as most potential flat board of future generation by industrial circle and academia and shows
Show technology, have the advantages that low-power consumption, wide viewing angle, respond it is fast, more frivolous and can Flexible Displays.
At present, according to the difference of luminescence mechanism, the material for OLED can be divided into fluorescent material and phosphorus
Luminescent material.According to spin quantum statistical theory, the singlet and triplet excitons formed after electronics and hole-recombination
Ratio be 1:3, therefore, the maximum internal quantum efficiency of fluorescence launched by singlet excitons attenuation is 25%.
And phosphor material can realize the phosphorescent emissions for being mixed with singlet state and triplet by intersystem crossing so that
The internal quantum efficiencies of PHOLED in theory are 100%.
In order to realize the luminescent layer in the high efficiency of phosphorescent devices, current Organic Light Emitting Diode all using main-visitor
Guest emitting material, i.e., be scattered in material of main part by body structure, is transferred energy to by main body luminescent material
Guest emitting material lights, with reduce exciton concentration it is excessive caused by be quenched and triplet state-triplet state annihilation.
Wherein, according to general requirement, the energy gap of material of main part should be more than the energy gap of guest emitter material, otherwise hold
Easily occur energy to be turned back to material of main part from guest emitter and reduce the efficiency of device, in addition, also to main body
Material has higher requirement on crystal property and glass transition temperature.
Therefore it provides a kind of be with above-mentioned performance requirement, the material of main part for being advantageously used in organic electroluminescent
Those skilled in the art in the urgent need to.
The content of the invention
Based on the requirement of above-mentioned background section, the invention provides a series of boron for organic electroluminescent
Azepine derivatives, it has good dissolubility and heat endurance；As Blue-light emitting host material, it can solve simultaneously
Small molecule guest materials is easy to crystallization and width can the shortcoming with the low Tg of material of main part；Further, the boron
Azepine derivatives are not limited to be used as material of main part, while may be used as electron injection material and electron transport material.
Technical scheme includes a kind of boron azepine derivatives for organic electroluminescent, it is characterised in that
Its structure is as shown in logical formula (I)：
Wherein, A is C or N；
R1、R2、R3、R4、R5、R6Separately selected from hydrogen, alkyl, the cyanogen that carbon number is 1-8
Aromatic amino that aromatic radical that base, carbon number are 5-50, carbon number are 5-50, carbon number are 10-60
Condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle aryl amine, carbon number be 10-60
Condensed hetero ring base and combinations thereof, and they can further be modified；
R7、R8、R9、R10、R11、R12、R13、R14And R15Separately it is selected from：Hydrogen, carbon atom
The aromatic amine that aromatic radical that alkyl that number is 1-8, cyano group, carbon number are 5-50, carbon number are 5-50
Base, carbon number are 10-60 condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle arylamine
Base, carbon number are 10-60 condensed hetero ring base and combinations thereof, and they can further be modified；
N, m are the Arbitrary Digit in 0,1,2,3.
In the preference of the present invention, R1With R2、R2With R3、R3With R4、R4With R5And R5With R6
Between can arbitrarily connect the aromatic radical, carbon to form that alkyl, carbon number that carbon number is 1-8 are 5-50
Condensed-nuclei aromatics base that aromatic amino that atomicity is 5-50, carbon number are 10-60, five yuan or hexa-member heterocycle
Base, five yuan or hexa-member heterocycle aryl amine, carbon number are 10-60 condensed hetero ring base and combinations thereof, and they can
To be further modified.
In the preference of the present invention, it is preferable that n is 1 or 2, m are 0,1 or 2.
In another preference of the present invention, R1、R2、R3、R4、R5、R6Separately selected from hydrogen,
Alkyl that cyano group, substituted or unsubstituted carbon number are 1-5, substituted or unsubstituted carbon number are 5-20
Aryl, substituted or unsubstituted carbon number for 10-30 condensed-nuclei aromatics base, substituted or unsubstituted five
Member or the condensed hetero ring base that hexa-member heterocycle base, substituted or unsubstituted carbon number are 10-30；It is further preferred
Ground, R1、R2、R3、R4、R5、R6Separately it is selected from hydrogen, substituted or unsubstituted phenyl, substitution
Or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl, substitution or unsubstituted
Indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl,
Substituted or unsubstituted pyrrole radicals, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and its group
Close, wherein, the substitution is preferably alkyl, phenyl, naphthyl, quinolyl, the phenanthrene for 1-8 by carbon number
Base, indenyl, fluorenyl, furyl, pyridine radicals, thienyl, pyrrole radicals, pyrimidine radicals are replaced.Most preferably,
R1、R2、R3、R4、R5、R6Separately selected from hydrogen, substituted or unsubstituted phenyl, substitution or not
Substituted naphthyl, substituted or unsubstituted pyridine radicals, the substitution be preferably by carbon number for 1-8 alkyl,
Phenyl, naphthyl, pyridine radicals are replaced.
In the preference of the present invention, R7、R8、R9、R10、R11、R12、R13、R14And R15It is only respectively
On the spot selected from hydrogen, cyano group, alkyl, the substituted or unsubstituted carbon that substituted or unsubstituted carbon number is 1-5
Condensed-nuclei aromatics base that aryl that atomicity is 5-20, substituted or unsubstituted carbon number are 10-30, take
Generation or the condensed hetero ring that unsubstituted five yuan or hexa-member heterocycle base, substituted or unsubstituted carbon number are 10-30
Base；Further preferably, R7、R8、R9、R10、R11、R12、R13、R14And R15Separately
Selected from hydrogen, cyano group, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinoline
Quinoline base, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substitution
Or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrole radicals, substitution or not
Substituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and combinations thereof, wherein, the substitution is preferably former by carbon
Subnumber is 1-8 alkyl, cyano group, phenyl, naphthyl, quinolyl, phenanthryl, indenyl, fluorenyl, furyl,
Pyridine radicals, thienyl, pyrrole radicals, pyrimidine radicals are replaced.It is further preferred that R7、R8、R9、R10、R11、
R12、R13、R14And R15Separately it is selected from：Hydrogen, cyano group, carbon number for 1-8 alkyl, substitution
Or unsubstituted phenyl, substituted or unsubstituted naphthyl, dibenzofurans, dibenzothiophenes；Wherein, it is described
Substitution is preferably to be replaced by cyano group, carbon number by 1-8 alkyl, phenyl, naphthyl, pyridine radicals.
In the preference of the present invention, the boron azepine derivatives preferably are selected from following structure：
It is blue that technical scheme also includes a kind of organic electroluminescent containing boron azepine derivatives described above
Light material of main part.
Technical scheme also includes a kind of organic electroluminescent electricity containing boron azepine derivatives described above
Sub- injection material.
Technical scheme also includes a kind of organic electroluminescent electricity containing boron azepine derivatives described above
Sub- transmission material.
Technical scheme also includes a kind of organic electroluminescence containing boron azepine derivatives described above
Part.
The glass transition temperature of material of main part has significant effect for the stability of device, it is however generally that, phase
The lifting of glass transition temperature can be brought to big molecular dimension, meanwhile, intermolecular three-dimensional effect also has
Certain humidification.Based on this, present inventor devises a series of boron azepine derivatives as material of main part,
Wherein, there is certain dihedral angle rather than total conjugated between two phenyl ring.The molecule of this class formation is due to benzene
Endless full conjugate between ring and phenyl ring brings 2 advantages：1) HOMO (highest occupied molecular orbital)
Energy level difference with LUMO (lowest unoccupied molecular orbital (LUMO)) is larger, is not likely to produce energy revolution；2) molecule is uncommon
Plane not allowing to be also easy to produce sedimentation and generation concentration quenching effect.In addition, by introducing there is electronics to pass
The unit of defeated performance or hole transport performance, can lift the electronics or hole transport performance of material.Thus, this
The boron azepine derivatives that invention is provided have wide energy band, high glass transition temperature, are difficult crystallization, concentration quenching effect
The advantages of answering small.
Embodiment
The invention provides a kind of boron azepine derivatives for organic electroluminescent, it is characterised in that its structure is such as
Shown in logical formula (I)：
Wherein, A is C or N；
R1、R2、R3、R4、R5、R6Separately selected from hydrogen, alkyl, the cyanogen that carbon number is 1-8
Aromatic amino that aromatic radical that base, carbon number are 5-50, carbon number are 5-50, carbon number are 10-60
Condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle aryl amine, carbon number be 10-60
Condensed hetero ring base and combinations thereof, and they can further be modified；
R7、R8、R9、R10、R11、R12、R13、R14And R15Separately it is selected from：Hydrogen, carbon atom
The aromatic amine that aromatic radical that alkyl that number is 1-8, cyano group, carbon number are 5-50, carbon number are 5-50
Base, carbon number are 10-60 condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle arylamine
Base, carbon number are 10-60 condensed hetero ring base and combinations thereof, and they can further be modified；
N, m are the Arbitrary Digit in 0,1,2,3.
In the preference of the present invention, R1With R2、R2With R3、R3With R4、R4With R5And R5With R6
Between can arbitrarily connect the aromatic radical, carbon to form that alkyl, carbon number that carbon number is 1-8 are 5-50
Condensed-nuclei aromatics base that aromatic amino that atomicity is 5-50, carbon number are 10-60, five yuan or hexa-member heterocycle
Base, five yuan or hexa-member heterocycle aryl amine, carbon number are 10-60 condensed hetero ring base and combinations thereof, and they can
To be further modified.
In the preference of the present invention, it is preferable that n is 1 or 2, m are 0,1 or 2.
In another preference of the present invention, R1、R2、R3、R4、R5、R6Separately selected from hydrogen,
Alkyl that cyano group, substituted or unsubstituted carbon number are 1-5, substituted or unsubstituted carbon number are 5-20
Aryl, substituted or unsubstituted carbon number for 10-30 condensed-nuclei aromatics base, substituted or unsubstituted five
Member or the condensed hetero ring base that hexa-member heterocycle base, substituted or unsubstituted carbon number are 10-30；It is further preferred
Ground, R1、R2、R3、R4、R5、R6Separately it is selected from hydrogen, substituted or unsubstituted phenyl, substitution
Or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl, substitution or unsubstituted
Indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl,
Substituted or unsubstituted pyrrole radicals, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and its group
Close, wherein, the substitution is preferably alkyl, phenyl, naphthyl, quinolyl, the phenanthrene for 1-8 by carbon number
Base, indenyl, fluorenyl, furyl, pyridine radicals, thienyl, pyrrole radicals, pyrimidine radicals are replaced.Most preferably,
R1、R2、R3、R4、R5、R6Separately selected from hydrogen, substituted or unsubstituted phenyl, substitution or not
Substituted naphthyl, substituted or unsubstituted pyridine radicals, the substitution be preferably by carbon number for 1-8 alkyl,
Phenyl, naphthyl, pyridine radicals are replaced.
In the preference of the present invention, R7、R8、R9、R10、R11、R12、R13、R14And R15It is only respectively
On the spot selected from hydrogen, cyano group, alkyl, the substituted or unsubstituted carbon that substituted or unsubstituted carbon number is 1-5
Condensed-nuclei aromatics base that aryl that atomicity is 5-20, substituted or unsubstituted carbon number are 10-30, take
Generation or the condensed hetero ring that unsubstituted five yuan or hexa-member heterocycle base, substituted or unsubstituted carbon number are 10-30
Base；Further preferably, R7、R8、R9、R10、R11、R12、R13、R14And R15Separately
Selected from hydrogen, cyano group, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinoline
Quinoline base, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substitution
Or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrole radicals, substitution or not
Substituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and combinations thereof, wherein, the substitution is preferably former by carbon
Subnumber is 1-8 alkyl, cyano group, phenyl, naphthyl, quinolyl, phenanthryl, indenyl, fluorenyl, furyl,
Pyridine radicals, thienyl, pyrrole radicals, pyrimidine radicals are replaced.It is further preferred that R7、R8、R9、R10、R11、
R12、R13、R14And R15Separately it is selected from：Hydrogen, cyano group, carbon number for 1-8 alkyl, substitution
Or unsubstituted phenyl, substituted or unsubstituted naphthyl, dibenzofurans, dibenzothiophenes；Wherein, it is described
Substitution is preferably to be replaced by cyano group, carbon number by 1-8 alkyl, phenyl, naphthyl, pyridine radicals.
In the preference of the present invention, the boron azepine derivatives preferably are selected from following structure：
Present invention also offers a kind of organic electroluminescent blue light main body material containing boron azepine derivatives described above
Material.
Present invention also offers a kind of organic electroluminescent electron injection material containing boron azepine derivatives described above
Material.
Present invention also offers a kind of organic electroluminescent electric transmission material containing boron azepine derivatives described above
Material.
Present invention also offers a kind of organic electroluminescence device containing boron azepine derivatives described above.
Specific embodiment is exemplified below, to be further explained and illustrate to technical scheme.
Embodiment 1
1st, the syntheti c route of the boron azepine derivatives shown in a kind of formula (1)
2nd, the preparation process of the boron azepine derivatives shown in a kind of formula (1)
(a) Compound 1 is synthesized
SM-1 (12g, 100mmol) and t-butyl sulfonamide (14.5g, 120mmol) is molten
Solution in the state of nitrogen protection, adds anhydrous cupric sulfate (32 in dry dichloromethane (250ml)
G, 200mmol), it is stirred at room temperature 24 hours.Filter solid is crossed, filtrate is collected, is concentrated to give solid white
Color crude product, petroleum ether (100ml) and dichloromethane (5ml) are added into crude product, and to stir 2 at room temperature small
When, it is filtrated to get Compound-1 white solids 19.8g.HPLC=99.8%, Yield=88.8%.
(b) Compound-2 is synthesized
Compound-1 (11g, 50mmol) is dissolved in dichloromethane (30ml), 2N is added
HCl methanol solutions (50ml), are stirred at room temperature 1 hour, are concentrated to give Compound-2 yellow oils
5.87g, HPLC=99.5, yield=100%.
(c) Compound-3 is synthesized
Compound-2 (5.87g, 50mmol) and triethylamine (15.15g, 150mmol) is molten
Dichlorophenyl boron is slowly added dropwise at 1,2- dichloro-benzenes (150ml) in solution at 0 DEG C, then flows back 12 hours, cold
But to room temperature, a large amount of solids are separated out, and are filtered, and washing is dried to obtain white solid 8g, HPLC=96%,
Yield=80%.
(d) Compound-5 is synthesized
By Compound-4 (33.4g, 100mmol), phenyl boric acid (12.2g, 100mmol), four or three
Phenylphosphine palladium (5.78g, 5mmol) and potassium carbonate (41.4g, 300mmol) are added to toluene (500ml)
In, flow back 2 hours under nitrogen protection, be cooled to room temperature, be directly used in next step.
(e) Compound-6 is synthesized
Last reaction solution is added into naphthalene boronic acids (17.2g, 100mmol) and tetra-triphenylphosphine palladium (5.78
G, 5mmol) flow back 2 hours under nitrogen protection, room temperature is cooled to, a large amount of solids are separated out, and cross filter solid,
Wash (100ml*3), dry, toluene (100ml*3) hot wash, drying obtains white solid 25g,
HPLC=97.2%, yield=65.8%.
(f) Compound-7 is synthesized
Compound-6 (5g, 13.2mmol) is suspended in CCl4 (100ml) and is heated to reflux,
NBS (2.34g, 13.2mmol) is added portionwise, flows back 5 hours, room temperature, a large amount of solid analysis is cooled to
Go out, cross filter solid, ethanol washing (20ml*3), drying obtains white solid 3.8g, HPLC=95.1%,
Yield=63%.
(g) compound 1 is synthesized
By Compound-7 (3.8g, 8.27mmol), Compound-3 (1.9g, 9.10mmol),
Pd2(dba)3(759mg, 0.83mmol), PMe3(118mg, 1.24mmol) and K-OtBu (279
Mg, 2.49mmol) toluene (70ml) is added to, nitrogen protection flows back 3 hours, is cooled to room temperature,
A large amount of solids are separated out, and are filtered, and are washed, and are dried, toluene hot wash (50ml*3), and drying obtains light yellow solid
Body 3.4g, HPLC=99.9, yield=70.8%.H-NMR (DMSO-d6, ppm)：7.91 (d,
1H) 7.89 (d, 1H), 7.75 (d, 1H), 7.67 (d, 2H), 7.63 (d, 1H), 7.54 (d, 1H),
7.48 (d, 2H), 7.39 (m, 3H), 7.32 (m, 9H), 7.22 (m, 1H), 7.0 (s, 1H),
6.8 (d, 1H), 6.44 (m, 4H), 6.39 (s, 1H), 5.2 (s, 1H)
Embodiment 2-8
With reference to the prepare compound 2,5,8,14,19,20,25 of embodiment 1.
Application Example 1
Device S1 preparation：Transparent anode electrode ito substrate is cleaned by ultrasonic 5~10 minutes in isopropanol,
And expose 20~30 minutes under ultraviolet light, then use corona treatment 5~10 minutes, will then handle
Ito substrate afterwards is put into evaporated device；First, the NPB for one layer of 30~50nm being deposited is used as hole transport
Layer；The TBPe of evaporation compound 1 and 5~10% is remixed as luminescent layer；20~40nm is then deposited
Alq3；0.5~2nm LiF are deposited again；100~200nm metal Al is finally deposited, OLED is obtained
Device S1：ITO/NPB/ compounds 1:TBPe/Alq3/LiF/Al.
Wherein, the structural formula of used compound CBP, NPB is as follows：
Application Example 2-8
The device S1 preparation with reference to described in Application Example 1, preparing for device S2-S8 is same, its
In：S2 is that material of main part prepares luminescent layer with compound 2；S3 is that material of main part preparation is luminous with compound 5
Layer；S4 is that material prepares electron transfer layer with compound 8；S5 is that material prepares electronics biography with compound 14
Defeated layer；Luminescent layer is prepared for material of main part with compound 19 in S6；S7 is material of main part with compound 20
Prepare luminescent layer；S9 is that material prepares hole transmission layer with compound 25.Device S2-S6 structure is as follows：
S2：ITO/NPB/ compounds 2:TBPe/Alq3/LiF/Al；
S3：ITO/NPB/ compounds 5:TBPe/Alq3/LiF/Al；
S4：ITO/NPB/CBP:TBPe/ compounds 8/LiF/Al；
S5：ITO/NPB/CBP:TBPe/ compounds 14/LiF/Al；
S6：ITO/NPB/CBP:TBPe/ compounds 19/LiF/Al；
S7：ITO/NPB/ compounds 20：TBPe/Alq3/LiF/Al；
S8：ITO/ compounds 25/CBP:TBPe/Alq3/LiF/Al.
Comparison study embodiment
Transparent anode electrode ito substrate is cleaned by ultrasonic 5~10 minutes in isopropanol, and exposed to ultraviolet
20~30 minutes under light, corona treatment is then used 5~10 minutes.Then by the ito substrate after processing
Evaporated device is put into, first, one layer of 30~50nm of evaporation NPB is used as hole transmission layer；Then mix
Evaporation CBP and 5~10% Ir (ppy) 3 is used as hole transmission layer；20~40nm Alq3 is then deposited
It is used as electron transfer layer；0.5~2nm LiF are deposited again；100~200nm metal Al is finally deposited, obtains
Obtain OLED D：ITO/NPB/CBP:Ir(ppy)3/Alq3/LiF/Al.
Device performance is detected
The properties of the OLED of Application Example 1-8 and Comparison study embodiment are under 1000nits
Measure, specific data referring to following table, wherein, Driver Voltage represent driving voltage, and Cd represents that electric current is imitated
Rate, CIEx, CIEy represent chromaticity coordinates.
Data explanation listed by table, compared to Comparison study embodiment, to include compound of the embodiment of the present invention
Material made from driving voltage needed for luminescent device is lower, more efficient, chromaticity coordinates is more preferable.
Unless limited otherwise, term used herein is the implication that those skilled in the art are generally understood that.
Embodiment described in the invention is not used to the protection model of the limitation present invention merely for exemplary purpose
Enclose, those skilled in the art can be made within the scope of the invention various other replacements, changes and improvements, thus,
The invention is not restricted to above-mentioned embodiment, and only it is defined by the claims.
Claims (10)
1. a kind of boron azepine derivatives for organic electroluminescent, it is characterised in that its structure is as shown in logical formula (I)：
Wherein, A is C or N；
R1、R2、R3、R4、R5、R6Separately it is selected from：Hydrogen, carbon number for 1-8 alkyl,
Aromatic amino that aromatic radical that cyano group, carbon number are 5-50, carbon number are 5-50, carbon number are
10-60 condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle aryl amine, carbon number are
10-60 condensed hetero ring base and combinations thereof, and they can further be modified；
R7、R8、R9、R10、R11、R12、R13、R14And R15Separately it is selected from：Hydrogen, carbon atom
The aromatic amine that aromatic radical that alkyl that number is 1-8, cyano group, carbon number are 5-50, carbon number are 5-50
Base, carbon number are 10-60 condensed-nuclei aromatics base, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle arylamine
Base, carbon number are 10-60 condensed hetero ring base and combinations thereof, and they can further be modified；
N, m are the Arbitrary Digit in 0,1,2,3.
2. boron azepine derivatives according to claim 1, it is characterised in that R1With R2、R2With R3、R3With
R4、R4With R5And R5With R6Between can arbitrarily connect to be formed carbon number be 1-8 alkyl, carbon atom
The condensed ring virtue that aromatic amino that aromatic radical that number is 5-50, carbon number are 5-50, carbon number are 10-60
Alkyl, five yuan or hexa-member heterocycle base, five yuan or hexa-member heterocycle aryl amine, carbon number are 10-60 condensed hetero ring
Base and combinations thereof, and they can further be modified.
3. boron azepine derivatives according to claim 1, it is characterised in that n be 1 or 2, m be 0,1 or
2。
4. boron azepine derivatives according to claim 1, it is characterised in that R1、R2、R3、R4、R5、
R6Separately selected from hydrogen, cyano group, substituted or unsubstituted carbon number for 1-5 alkyl, substitution or not
The condensed ring virtue that aryl that substituted carbon number is 5-20, substituted or unsubstituted carbon number are 10-30
Alkyl, substituted or unsubstituted five yuan or hexa-member heterocycle base, substituted or unsubstituted carbon number are 10-30
Condensed hetero ring base.
5. boron azepine derivatives according to claim 1, it is characterised in that R1、R2、R3、R4、R5、
R6Separately it is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substitution or does not take
The quinolyl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl,
Substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrole radicals, substitution
Or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and combinations thereof, wherein, the substitution is former by carbon
Subnumber is 1-8 alkyl, phenyl, naphthyl, quinolyl, phenanthryl, indenyl, fluorenyl, furyl, pyridine radicals,
Thienyl, pyrrole radicals, pyrimidine radicals are replaced.
6. the boron azepine derivatives according to claim 4 or 5, it is characterised in that R7、R8、R9、R10、
R11、R12、R13、R14And R15Separately it is selected from hydrogen, cyano group, substituted or unsubstituted carbon number
The aryl for being 5-20 for 1-5 alkyl, substituted or unsubstituted carbon number, substituted or unsubstituted carbon
Atomicity is 10-30 condensed-nuclei aromatics base, substituted or unsubstituted five yuan or hexa-member heterocycle base, substitution or do not taken
The carbon number in generation is 10-30 condensed hetero ring base.
7. the boron azepine derivatives according to claim 4 or 5, it is characterised in that R7、R8、R9、R10、
R11、R12、R13、R14And R15Separately selected from hydrogen, cyano group, substituted or unsubstituted phenyl, take
Generation or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl, substitution or do not take
The indenyl in generation, substituted or unsubstituted fluorenyl, substituted or unsubstituted furyl, substituted or unsubstituted thiophene
Base, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and
It is combined, wherein, the substitution is alkyl, cyano group, phenyl, naphthyl, the quinoline for 1-8 by carbon number
Base, phenanthryl, indenyl, fluorenyl, furyl, pyridine radicals, thienyl, pyrrole radicals, pyrimidine radicals are replaced.
8. boron azepine derivatives according to claim 1, it is characterised in that the boron azepine derivatives are selected from as follows
Structure：
9. a kind of organic electroluminescent blue light of the boron azepine derivatives containing as described in any one in claim 1-8
Material of main part, electron injection material or electron transport material.
10. a kind of organic electroluminescence of the boron azepine derivatives containing as described in any one in claim 1-8
Part.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109232623A (en) * | 2018-09-30 | 2019-01-18 | 天津理工大学 | A kind of synthetic method of boron aza-phenanthrenes and its derivative |
| CN110256498A (en) * | 2018-03-12 | 2019-09-20 | 上海和辉光电有限公司 | Luminescent layer guest materials, the luminescent layer comprising it and OLED display panel and electronic equipment |
| WO2020218514A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescent element and electronic device |
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2016
- 2016-03-21 CN CN201610160951.4A patent/CN107216347A/en active Pending
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256498A (en) * | 2018-03-12 | 2019-09-20 | 上海和辉光电有限公司 | Luminescent layer guest materials, the luminescent layer comprising it and OLED display panel and electronic equipment |
| CN109232623A (en) * | 2018-09-30 | 2019-01-18 | 天津理工大学 | A kind of synthetic method of boron aza-phenanthrenes and its derivative |
| CN109232623B (en) * | 2018-09-30 | 2021-04-20 | 天津理工大学 | Synthetic method of borazaphenanthrene and derivatives thereof |
| WO2020218514A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescent element and electronic device |
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