CN114014883A - Organic boron compound and application thereof in organic electroluminescent device - Google Patents
Organic boron compound and application thereof in organic electroluminescent device Download PDFInfo
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- CN114014883A CN114014883A CN202111444668.1A CN202111444668A CN114014883A CN 114014883 A CN114014883 A CN 114014883A CN 202111444668 A CN202111444668 A CN 202111444668A CN 114014883 A CN114014883 A CN 114014883A
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- 150000001639 boron compounds Chemical class 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 33
- -1 nitro, cyano, methyl Chemical group 0.000 claims description 33
- 239000010410 layer Substances 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 150000001555 benzenes Chemical group 0.000 claims description 10
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000004826 dibenzofurans Chemical class 0.000 claims description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 150000002790 naphthalenes Chemical class 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000011800 void material Substances 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 7
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 abstract description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052796 boron Inorganic materials 0.000 abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 abstract description 2
- 230000005611 electricity Effects 0.000 abstract 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000005311 nuclear magnetism Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ZLPPJJZCOCPXDE-UHFFFAOYSA-N 2-chloro-10h-phenoxazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3OC2=C1 ZLPPJJZCOCPXDE-UHFFFAOYSA-N 0.000 description 2
- APYSHMNJHJRIDR-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine Chemical compound C1=CC=CN2C(Br)=CN=C21 APYSHMNJHJRIDR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring 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
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- 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
- SBPIDKODQVLBGV-UHFFFAOYSA-N 1h-imidazole;pyridine Chemical compound C1=CNC=N1.C1=CC=NC=C1 SBPIDKODQVLBGV-UHFFFAOYSA-N 0.000 description 1
- GTRVPGHUUDKYIQ-UHFFFAOYSA-N 3-bromo-7-phenylimidazo[1,2-a]pyridine Chemical compound C1=CN2C(Br)=CN=C2C=C1C1=CC=CC=C1 GTRVPGHUUDKYIQ-UHFFFAOYSA-N 0.000 description 1
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-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
- MGMOFYJWVCDHOB-UHFFFAOYSA-N N-(4-tert-butylphenyl)dibenzofuran-2-amine Chemical compound CC(C)(C)C1=CC=C(NC2=CC3=C(OC4=C3C=CC=C4)C=C2)C=C1 MGMOFYJWVCDHOB-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate 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
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- SBMXAWJSNIAHFR-UHFFFAOYSA-N n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC=3C=C4C=CC=CC4=CC=3)=CC=C21 SBMXAWJSNIAHFR-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 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
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
-
- 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
- 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
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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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- 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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- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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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
- C09K2211/1018—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
- 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
- C09K2211/1074—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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- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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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 an organic boron compound and application thereof in an organic electroluminescent device, belonging to the technical field of photoelectric materials. The compound is a main body formed by bonding imidazopyridine with group nitrogen such as arylamine, carbazole, acridine and the like, the center of the main body is modified by boron, the compound has a rigid large conjugated structure, the supply/receiving electricity of the compound is adjusted by the bipolar imidazopyridine group, and the HOMO of the compound is reduced, so that a device prepared by using the compound as a luminescent layer material shows stable and efficient deep blue light emission, and the device is remarkably improved in the aspects of driving voltage, current efficiency, light color and service life.
Description
Technical Field
The invention relates to the field of photoelectric materials, in particular to an organic boron compound and application thereof in an organic electroluminescent device.
Background
An organic electroluminescent device (OLED) includes a cathode, an anode, and an organic layer between the two electrodes, and the organic layer includes a hole transport layer, an electron transport layer, a light emitting layer, and the like. Under the drive of an external electric field, holes and electrons are firstly injected from the anode and the cathode respectively, then move oppositely in the hole transport layer and the electron transport layer, and are then compounded into exciton radiation transition in the luminescent layer to emit various colors of light.
In order to apply the OLED to full color display, it is a primary problem to implement a rgb three-color device having high efficiency. Currently, for green and red OLEDs, a light emitting material based on a phosphorescence and Thermally Activated Delayed Fluorescence (TADF) mechanism has achieved 100% internal quantum efficiency, and has achieved mass industrialization, being widely used in commercial full color display devices. However, the deep blue OLED material with high quality display has not achieved a significant breakthrough all the time, the blue material has a wide band gap, the carrier transfer and energy transfer processes in the electroluminescence process are difficult and unstable, and the mutual quenching and deactivation phenomenon among excitons under high current density is very serious, so that most deep blue devices have very serious device efficiency roll-off and low brightness, and the service life is very short.
In recent years, a novel organic unit material of pi-conjugate containing organic boron and nitrogen in a co-insertion mode has good photophysical and electrochemical properties, so that the organic unit material becomes a research hotspot of a blue-light OLED material system, imidazole has acidity and alkalinity simultaneously, is a bipolar compound, is applied to the blue-light OLED material, and has important significance for adjusting the balance of current carriers.
Disclosure of Invention
The invention aims to provide an organic boron compound and application thereof in an organic electroluminescent device, and improves the carrier transmission balance of the current deep blue light luminescent material, so that the deep blue light OLED device has excellent comprehensive properties in the aspects of luminous efficiency, stability, light color, service life and the like.
The invention provides an organic boron compound, the structural general formula of which is shown in formula (1):
wherein,
are the same or different and are each independently represented by a void or a single bond or-X0-，X0Selected from O, S, N (R)2) And C (R)3)(R4) Any one of the above;
Ar、Ar1and Ar2Are the same or different from each other, and are each independently selected from a benzene ring, a condensed aromatic ring having not more than 18 carbon atoms, a condensed aromatic heterocyclic ring having not more than 18 carbon atoms, R1Substituted benzene ring, R1A substituted fused aromatic ring having not more than 18 carbon atoms and R1Any one of condensed aromatic heterocyclic rings having not more than 18 carbon atoms in substitution;
R0selected from hydrogen, fluoro, nitro, cyano, C1-12Alkyl of (C)6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R1selected from hydrogen, fluoro, nitro, cyano, C1-12Alkyl of (C)1-12Alkoxy group of (C)3-12Cycloalkyl of, C2-20Heterocycloalkyl of (A), C6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R2-R4are 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, Ar1And Ar2The same or different from each other, each independently selected from any one of the following: unsubstituted or substituted by R1Substituted benzenes, unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1Substituted carbazoles wherein the symbols and indices used have the meanings given in claim 1. Namely, R1Is defined as in the above chemical formula 11The same is true.
Further, when Ar, Ar1And Ar2Each independently of the other being unsubstituted or substituted by R1When substituted benzene, the organoboron compound is a compound represented by the formula 1-1:
when Ar, Ar1Each independently of the other being unsubstituted or substituted by R1Substituted benzenes, and Ar2Is unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1When any one of the substituted carbazoles is used, the organoboron compound is a compound represented by the formula 1-2:
when Ar is unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1Any one of substituted carbazoles, and Ar2Is unsubstituted or substituted by R1When substituted benzene, the organoboron compound is a compound represented by formula 1 to 3 or formula 1 to 4:
when Ar, Ar2Each independently of the others being unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1Any of the substituted carbazolesIn this case, the organoboron compound is a compound represented by the formula 1 to 5 or the formula 1 to 6:
wherein Ar is1、Ar2Is defined by the formula (I) and Ar in claim 21、Ar2The definitions of (A) and (B) are the same,
R0is as defined in the above formula 10In the same way, the first and second,
R1is as defined in the above formula 11In the same way, the first and second,
R5、R6、R7is as defined in the above formula 11In the same way, the first and second,
z is selected from O, S, C (CH)3)2And N (Ph).
Further, R2Is any one of phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl and tert-butyl.
Further, R3And R4The same as each other, are each methyl.
Further, R1Selected from: hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl, tert-butyl, phenyl.
Further, R0Independently any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, phenyl unsubstituted or substituted by fluoro, nitro, cyano, methyl, tert-butyl, biphenyl, a group of formula A1, a group of formula A2 and a group of formula A3:
wherein, X1Selected from O, S, N (R)8)、C(R9)(R10)，R8-R10The phenyl groups are the same or different from each other and are independently selected from any one of methyl, phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl and tert-butyl.
Further, the organoboron compound shown in the formula 1 is selected from any one of the following structural formulas:
in a second aspect, the present invention provides an organic electroluminescent device comprising a cathode, an anode and an organic layer disposed between the cathode and the anode, the organic layer comprising an organoboron compound of any of the above.
Further, the organic layer between the two electrodes includes a light-emitting layer containing any of the organoboron compounds described above.
The organic boron compound provided by the invention is used for forming a receptor type main body framework by linking imidazole pyridine with strong electron deficiency property and radical nitrogen with electron donating property such as arylamine, carbazole, acridine and the like, and the mobility of current carriers on the whole compound is more balanced, so that higher fluorescence quantum yield can be obtained, and the center of the main body is modified by boron to form a rigid large conjugated structure, so that the HOMO of the compound is reduced, a wider band gap is obtained, stable deep blue light emission can be realized, and better thermodynamic stability can be obtained, and the organic boron compound is further applied to an organic electroluminescent device and has remarkable advantages in the aspects of starting voltage, luminous efficiency, service life and the like of the device.
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 (7)
S1: after 3-bromoimidazo [1,2-a ] pyridine (35mmol,6.90g), 2, 3-dichloro-5-fluoro-mesitylene (30mmol,8.95g), sodium tert-butoxide (60mmol,5.76g), tris (dibenzylideneacetone) dipalladium (0.15mmol,0.14g), tris (tert-butylphosphine) tetrafluoroborate (0.15mmol,0.04g) and 100mL of toluene were charged into a reactor, they were sufficiently stirred and mixed, and then heated under nitrogen protection for reflux reaction, after completion of liquid phase monitoring reaction, they were cooled to room temperature, diphenylamine (30mmol,5.08g) was charged, and they were sufficiently stirred and mixed, and under nitrogen protection, they were further heated under reflux reaction, after completion of liquid phase monitoring reaction, they were cooled to room temperature, the reaction solution was extracted with a mixture of water and dichloromethane, dried and concentrated, and purified and separated in a silica gel column with a mixed solvent of 1:10 dichloromethane and petroleum ether, 10.18g of a compound represented by the following chemical formula (7a) was obtained in a yield of 62%;
s2: after the compound represented by the above formula (7a) (15mmol,8.21g), 10-hydro-phenoxazine (20mmol,3.66g), cesium carbonate (22.5mmol,7.33g) and 100mL of N, N-dimethylformamide were charged into a reactor, and sufficiently stirred and mixed, a reflux reaction was performed under heating under nitrogen protection, the liquid phase monitoring reaction was completed, cooling to room temperature was performed, 50mL to 100mL of water was added, filtration was performed, the filtrate was extracted with dichloromethane for 2 times, concentrated, and slurried with ethanol for 2 times together with the cake, whereby 8.52g of the compound represented by the following formula (7b) was obtained with a yield of 80%;
s3: dissolving the compound (10mmol,7.10g) represented by the formula (7b) in 50mL of tert-butyl benzene solution in a reactor, cooling the reaction solution to-40 ℃, slowly adding 32.5mL of 2.5M N-hexane tert-butyl lithium solution dropwise under the protection of nitrogen, stirring for 0.5-2h while maintaining the temperature, adding boron tribromide (15mmol,3.76g), heating the reaction solution to room temperature, 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 in a liquid phase, cooling to room temperature, quenching the reaction solution with acetic acid, extracting the reaction solution with a mixture of water and dichloromethane, drying an organic phase magnesium sulfate, concentrating, purifying and separating in a silica gel column with a mixed solvent of 1:10 dichloromethane and petroleum ether to obtain 2.39g of the compound represented by the following formula (7), the yield is 35 percent;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 683.6275; nuclear magnetism δ (ppm) is 9.02(1H), 8.79(1H), 8.45(1H), 7.78(2H), 7.70(1H), 7.62(1H), 7.47(1H), 7.35(2H), 7.22(1H), 6.89-6.95(4H)6.77(2H), 6.70(1H), 6.59(2H), 6.26(1H), 6.02(2H), 5.22(2H), 2.20 (9H).
Synthesis example 2: synthesis of Compound (13)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 with 2, 3-dichloro-N-diphenylamine (30mmol,7.14g) and replacing diphenylamine with 3, 6-diphenyl-9-hydro-carbazole (30mmol,9.58g) in example 1 to give 11.09g of a compound represented by the following formula (13a) in a yield of 58%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 6.37g of the compound represented by (13a) described in this example, whereby 1.89g of the compound represented by the following chemical formula (13) was obtained in a yield of 31%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 610.5309; nuclear magnetism δ (ppm) is 9.05(1H), 8.90(1H), 8.76(1H), 8.45(1H), 8.22(1H), 8.06(1H), 7.95(1H), 7.81-7.87(4H), 7.72(2H), 7.62(3H), 7.48(2H), 7.32(2H), 7.20(2H), 7.05(1H), 6.73(1H), 6.25(1H), 6.14 (2H).
Synthetic example 3: synthesis of Compound (26)
S1: the same procedures used in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene amine in S1 with N- (2, 3-dichlorophenyl) - [1,1' -biphenyl ] -4-amine (30mmol,9.43g) and diphenylamine with 5- (p-tolyl) -5, 10-dihydrophenazine (30mmol,8.17g) in example 1 to give 12.79g of the compound represented by the following formula (26a) in a yield of 64%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 6.66g of the compound represented by (26a) in this example to give 2.11g of the compound represented by the following formula (26) in a yield of 33%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 639.5615; nuclear magnetism δ (ppm) is 9.03(1H), 8.42(1H), 8.11(1H), 7.78(2H), 7.71(1H), 7.63(1H), 7.55(2H), 7.48(2H), 7.40(1H), 7.32(2H), 7.27(1H), 7.21(2H), 7.16(1H), 6.97-7.03(5H), 6.89(1H), 6.26(1H), 6.14(2H), 2.26 (3H).
Synthetic example 4: synthesis of Compound (28)
S1: the same procedures as in example 1 were repeated except for replacing diphenylamine in S1 with 10-hydrogen-phenothiazine (30mmol,5.98g) in example 1 to give 10.39g of a compound represented by the following formula (28a) in a yield of 60%;
s2: the same procedures as in example 1 were repeated except for replacing (7a) in S2 with 8.66g of the compound represented by the above-mentioned (28a) in example 1 and replacing 10 h-phenoxazine with 9 h-carbazole (20mmol,3.34g), thereby obtaining 9.02g of the compound represented by the following formula (28b) with a yield of 83%;
s3: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 7.24g of the compound represented by (28b) described in this example, whereby 2.52g of the compound represented by the following chemical formula (28) was obtained in a yield of 36%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 697.6698; nuclear magnetism δ (ppm) is 9.10(1H), 8.47(1H), 8.18(2H), 7.95(1H), 7.83(1H), 7.75(2H), 7.64(1H), 7.50(2H), 7.21(3H), 7.12(1H), 7.00(1H), 6.87-6.94(4H), 6.80(2H), 6.31(1H), 2.20 (9H).
Synthesis example 5: synthesis of Compound (33)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with 2-chloro-9-hydro-carbazole (30mmol,6.05g) and replacing diphenylamine with 4,4' -dicyanodianiline (30mmol,6.58g), to give 8.56g of a compound represented by the following formula (33a) in a yield of 57%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 5.01g of the compound represented by (33a) described in this example, whereby 1.73g of the compound represented by the following chemical formula (33) was obtained 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 508.3561.
Synthetic example 6: synthesis of Compound (39)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with 2-chloro-10-hydro-phenothiazine (30mmol,7.01g) and replacing diphenylamine with bis (4- (tert-butyl) phenyl) amine (30mmol,8.44g), thereby obtaining 10.53g of a compound represented by the following formula (39a) in a yield of 59%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 5.95g of the compound represented by (39a) described in this example, whereby 1.87g of the compound represented by the following formula (39) was obtained 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 602.6023.
Synthetic example 7: synthesis of Compound (46)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with 2-chloro-9-hydro-carbazole (30mmol,6.05g), 3-bromoimidazo [1,2-a ] pyridine with 3-bromo-7-phenylimidazo [1,2-a ] pyridine (35mmol,9.56g) and diphenylamine with 9-hydro-carbazole (30mmol,5.02g), to give 9.60g of the compound represented by the following formula (46a) in a yield of 61%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 5.25g of the compound represented by (46a) described in this example, whereby 1.86g of the compound represented by the following formula (46) was obtained 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 532.4167.
Synthesis example 8: synthesis of Compound (49)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with 2-chloro-9-hydro-carbazole (30mmol,6.05g), diphenylamine with 9, 9-dimethyl-9, 10-dihydroacridine (30mmol,6.28g), to give 9.57g of a compound represented by the following formula (49a) in a yield of 65%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 4.91g of the compound represented by (49a) described in this example, whereby 1.84g of the compound represented by the following formula (49) 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 498.3928.
Synthetic example 9: synthesis of Compound (52)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene amine in S1 with 2-chloro-10 h-phenoxazine (30mmol,6.53g) and replacing diphenylamine with 10 h-phenoxazine (30mmol,5.50g) in example 1 to give 9.08g of a compound represented by the following formula (52a) in a yield of 63%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 4.81g of the compound represented by (52a) described in this example, whereby 1.66g of the compound represented by the following formula (52) was obtained 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 488.3175.
Synthetic example 10: synthesis of Compound (58)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene amine in S1 with 2-chloro-5-phenyl-5, 10-dihydrophenazine (30mmol,8.78g) and replacing diphenylamine with 3, 6-difluoro-9-hydro-carbazole (30mmol,6.10g) in example 1 to obtain 10.36g of a compound represented by the following formula (58a) in a yield of 60%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 5.76g of the compound represented by (58a) described in this example, whereby 1.87g of the compound represented by the following formula (58) was obtained 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 583.4043.
Synthetic example 11: synthesis of Compound (65)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with (2, 3-dichloro-5-fluorophenyl) naphthalen-2-amine (30mmol,9.18g) and replacing diphenylamine with 9-hydro-carbazole (30mmol,5.02g), to obtain 9.13g of a compound represented by the following formula (65a) in a yield of 55%;
s2: the same procedure as in example 1 was repeated except for replacing (7a) in S2 with 8.30g of the compound represented by the above-mentioned (65a) in example 1 and replacing 10-hydro-phenoxazine with diphenylamine (20mmol,3.38g), thereby obtaining g of the compound represented by the following formula (65b) in a yield of 81%;
s3: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 7.02g of the compound represented by (65b) described in this example to give 2.50g of the compound represented by the following formula (65) in a yield of 37%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 675.6066; nuclear magnetic δ (ppm) is 9.04(1H), 8.67(1H), 8.47(1H), 8.18(1H), 7.98(2H), 7.87(1H), 7.70(1H), 7.60(1H), 7.47-7.54(6H), 7.41(1H), 7.38(1H), 7.33(1H), 7.20(1H), 7.11(5H), 7.01(1H), 6.94(2H), 6.25(1H), 5.22 (2H).
Synthetic example 12: synthesis of Compound (70)
S1: the procedure of example 1 was repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with N- (2, 3-dichloro-5-nitrophenyl) -9, 9-dimethyl-9-hydro-fluoren-2-amine (30mmol,11.98g) and replacing diphenylamine with 10-hydro-phenothiazine (30mmol,5.98g), to give 11.80g, in 58% yield, of the compound represented by the following formula (70 a);
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 6.78g of the compound represented by (70a) described in this example, whereby 2.28g of the compound represented by the following formula (70) was obtained in a yield of 35%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 651.5478; nuclear magnetism δ (ppm) is 9.02(1H), 8.43(1H), 8.19(1H), 8.04(2H), 7.98(1H), 7.87(2H), 7.75(1H), 7.63(1H), 7.51(1H), 7.44(1H), 7.38(1H), 7.12-7.21(3H), 7.02(2H), 6.91(1H), 6.25(1H), 1.79 (6H).
Synthetic example 13: synthesis of Compound (73)
S1: the procedure of example 1 was repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene in S1 in example 1 with N- (2, 3-dichlorophenyl) -2,4, 6-trimethylamine (30mmol,8.41g) and diphenylamine with N- (4- (tert-butyl) phenyl) dibenzofuran-2-amine (30mmol,9.46g), to give 10.74g of a compound represented by the following formula (73a) in a yield of 53%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 6.75g of the compound represented by (73a) described in this example, whereby 2.47g of the compound represented by the following formula (73) was obtained in a yield of 38%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 648.6126; nuclear magnetism δ (ppm) is 9.06(1H), 8.45(1H), 8.33(1H), 8.05(1H), 7.74(1H), 7.61(1H), 7.63(1H), 7.43-7.51(3H), 7.36(1H), 7.25(1H), 7.13(2H), 6.95(2H), 6.23(1H), 6.14(2H), 2.20(9H), 1.35 (9H).
Synthesis example 14: synthesis of Compound (80)
S1: the same procedures as in example 1 were repeated except for replacing 2, 3-chloro-5-fluoro-mesitylene amine in S1 in example 1 with 2-chloro-10 h-phenoxazine (30mmol,6.53g) and replacing diphenylamine with N- (2, 5-dimethyl- [1,1' -biphenyl ] -4-yl) naphthalen-2-amine (30mmol,9.70g), to obtain 10.61g of a compound represented by the following formula (80a) in a yield of 57%;
s2: the same procedures used in example 1 were repeated except for replacing the compound represented by (7b) in S3 in example 1 with 6.21g of the compound represented by (80a) described in this example, whereby 2.08g of the compound represented by the following formula (80) was obtained in a yield of 33%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 628.5389; nuclear magnetism δ (ppm) is 9.02(1H), 8.48(1H), 7.84(1H), 7.79(1H), 7.70(1H), 7.64(1H), 7.54(2H), 7.38-7.47(4H), 7.30(2H), 7.21(3H), 7.15(1H), 7.06(1H), 6.98(1H), 6.85(1H), 6.77(1H), 6.26(1H), 2.47(3H), 2.19 (3H).
Synthetic example 15: synthesis of Compound (81)
The same procedures as in example 1 were repeated except for replacing 2, 3-dichloro-5- (10 h-phenoxazin-10-yl) -N-diphenylamine in example 1 with N- (2, 3-dichlorophenyl) naphthalene-2-amine (30mmol,8.65g) and replacing diphenylamine with 2, 2-dinaphthylamine (30mmol,8.08g), thereby obtaining 11.28g of a compound represented by the following formula (81a) in a yield of 59%;
the same procedures used in example 1 were repeated except for replacing the compound represented by (7a) in example 1 with 6.37g of the compound represented by (81a) above, thereby obtaining 2.32g of the compound represented by the following formula (81) with a yield of 38%;
the compound obtained was analyzed and found to have the following results: mass spectrometer MALDI-TOF-MS (m/z) 610.5306; nuclear magnetism δ (ppm) is 9.03(1H), 8.44(1H), 7.75-7.87(6H), 7.61(1H), 7.54(2H), 7.49(3H), 7.43(3H), 7.38(2H), 7.31(1H), 7.26(1H), 7.06(1H), 7.01(2H), 6.25(1H), 6.14 (2H).
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 4,4' -tris [ 2-naphthyl (phenyl) amino ] triphenylamine (2T-NATA) on the surface of the side on which the ITO film is formed to form a hole injection layer with a thickness of 80 nm;
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 30nm thick hole transport layer;
next, on the above hole transport layer, compound 7 prepared in the above synthesis example 1 was vacuum-evaporated to form a light emitting layer having a thickness of 30 nm;
next, on the above light-emitting layer, bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BAlq) was vacuum-evaporated to form a hole-blocking layer with a thickness of 10 nm;
next, 8-hydroxyquinoline aluminum (Alq) was vacuum-evaporated on the hole-blocking layer3) To form an electron transport layer with a thickness of 20 nm;
finally, on the above electron transport layer, aluminum (Al) was vacuum-evaporated to form a cathode of 100 nm.
Device example 2 to device example 15
An organic electroluminescent device was prepared in the same manner as in device example 1, except that the compound synthesized in synthesis example 2 to synthesis example 15 described above was used instead of the compound 7 prepared in synthesis example 1 described above, respectively.
The organic electroluminescent devices prepared in the above device 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, the compound provided by the present invention, in which the imidazopyridine is linked with groups such as arylamine, carbazole, acridine, etc. through a ring nitrogen bond to form the host and boron is used to modify the center of the host, has a rigid conjugated structure, and the bipolar imidazopyridine group can adjust the power supply and the power reception of the compound, and simultaneously reduce the HOMO of the compound, so that the compound material can realize stable and efficient deep blue light emission.
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 (10)
1. An organic boron compound is characterized in that the structural general formula of the compound is shown as formula 1:
wherein,
are the same or different and are each independently represented by a void or a single bond or-X0-, said X0Selected from O, S, N (R)2) And C (R)3)(R4) Any one of the above;
Ar、Ar1and Ar2Equal to or different from each other, each independently selected from: a benzene ring, a condensed aromatic ring having not more than 18 carbon atoms, a condensed aromatic heterocyclic ring having not more than 18 carbon atoms, R1Substituted benzene ring, R1A substituted fused aromatic ring having not more than 18 carbon atoms and R1Any one of condensed aromatic heterocyclic rings having not more than 18 carbon atoms in substitution;
R0selected from hydrogen, fluoro, nitro, cyano, C1-12Alkyl of (C)6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R1selected from hydrogen, fluoro, nitro, cyano, C1-12Alkyl of (C)1-12Alkoxy group of (C)3-12Cycloalkyl of, C2-20Heterocycloalkyl of (A), C6-30Aryl of (C)3-30Heteroaryl and C6-30Any one of the arylamine groups of (a);
R2-R4are 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 organoboron compound of claim 1, where Ar, Ar are Ar1And Ar2The same or different from each other, each independently selected from any one of the following: unsubstituted or substituted by R1Substituted benzenes, unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1Substituted carbazoles wherein the symbols and indices used have the meanings given in claim 1.
3. The organoboron compound of claim 2, characterized in that,
when Ar, Ar1、Ar2Each independently of the other being unsubstituted or substituted by R1When substituted benzene, the organoboron compound is a compound represented by the formula 1-1:
when Ar, Ar1Each independently of the other being unsubstituted or substituted by R1Substituted benzenes, and Ar2Is unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1When any one of the substituted carbazoles is used, the organoboron compound is a compound represented by the formula 1-2:
when Ar is unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1Any one of substituted carbazoles, and Ar2Is unsubstituted or substituted by R1When substituted benzene, the organoboron compound is a compound represented by formula 1 to 3 or formula 1 to 4:
when Ar, Ar2Each independently of the others being unsubstituted or substituted by R1Substituted naphthalenes, unsubstituted or substituted by R1Substituted dibenzofurans, unsubstituted or substituted by R1Substituted dibenzothiophenes, unsubstituted or substituted by R1Substituted 9, 9-dimethylfluorenes, unsubstituted or substituted by R1When any one of the substituted carbazoles is selected, the organoboron compound is a compound represented by formula 1-5 or formula 1-6:
wherein Ar is1、Ar2Is defined by the formula (I) and Ar in claim 21、Ar2The definitions of (A) and (B) are the same,
R1is as defined in the above formula 11In the same way, the first and second,
R5、R6、R7is as defined in the above formula 11In the same way, the first and second,
z is selected from O, S, C (CH)3)2And N (Ph).
4. The organoboron compound of claim 1, where R is2Is any one of phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl and tert-butyl.
5. The organoboron compound of claim 1, where R is3And R4The same as each other, are each methyl.
6. The organoboron compound of claim 1, where R is1Is selected from any one of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl, tert-butyl and phenyl.
7. The organoboron compound of claim 1, where R is0Independently is any of hydrogen, fluoro, nitro, cyano, methyl, tert-butyl, phenyl, biphenyl, a group of formula A1, a group of formula A2 and a group of formula A3 which are unsubstituted or substituted by fluoro, nitro, cyano, methyl, tert-butylThe method comprises the following steps:
wherein, X1Selected from O, S, N (R)8)、C(R9)(R10)，R8-R10The phenyl groups are the same or different from each other and are independently selected from any one of methyl, phenyl which is unsubstituted or substituted by fluoro, nitro, cyano, methyl and tert-butyl.
8. The organoboron compound of claim 1, where the organoboron compound is selected from any of the following structural formulas:
9. an organic electroluminescent device comprising a cathode, an anode and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the organoboron compound of any of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer comprising the organoboron compound according to any one of claims 1 to 8.
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| CN112778343A (en) * | 2020-12-31 | 2021-05-11 | 武汉尚赛光电科技有限公司 | Boron-based organic electroluminescent material and preparation method and application thereof |
| WO2021187939A1 (en) * | 2020-03-19 | 2021-09-23 | 에스에프씨 주식회사 | Novel boron compound and organic light-emitting element comprising same |
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