CN108640940A - A kind of stable type boracic organic electroluminescent compounds and its application - Google Patents
A kind of stable type boracic organic electroluminescent compounds and its application Download PDFInfo
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- CN108640940A CN108640940A CN201810513502.2A CN201810513502A CN108640940A CN 108640940 A CN108640940 A CN 108640940A CN 201810513502 A CN201810513502 A CN 201810513502A CN 108640940 A CN108640940 A CN 108640940A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 239000000463 material Substances 0.000 claims abstract description 77
- 238000005401 electroluminescence Methods 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims description 15
- -1 dibiphenylyl Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960005544 indolocarbazole Drugs 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005266 diarylamine group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000010410 layer Substances 0.000 description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 238000012360 testing method Methods 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
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- 239000007787 solid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- 238000001914 filtration Methods 0.000 description 10
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical class CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 7
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- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical class C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
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- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
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- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- IOSLINNLJFQMFF-XMMPIXPASA-N [(2R)-1-[[4-[[3-[(4-fluorophenyl)methylsulfanyl]phenoxy]methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound FC1=CC=C(CSC=2C=C(OCC3=CC=C(CN4[C@H](CCC4)CO)C=C3)C=CC=2)C=C1 IOSLINNLJFQMFF-XMMPIXPASA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
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- 150000004826 dibenzofurans Chemical class 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- 210000004209 hair Anatomy 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
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- 150000003512 tertiary amines Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
The invention discloses a kind of boracic high efficiency organic electroluminescence compound and its applications, shown in the structural formula such as general formula (1) of the compound.This kind of material has good fluorescence quantum efficiency and electroluminescent efficiency, easily forms armorphous film, has good thermal stability, therefore such material can be used as emitting layer material in organic electroluminescence device and use.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of synthesis of fluorescent chemicals, and as luminous
Application of the layer material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make
New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
Currently, OLED display technologies in smart mobile phone, applied by the fields such as tablet computer, further will also be to electricity
Depending on etc. large scales application field extension.But require to compare with actual products application, the luminous efficiency of OLED device uses
The performances such as service life also need to further be promoted.
OLED luminescent devices like the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together.
As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, that is, generates OLED electroluminescent.
Proposing high performance research for OLED luminescent devices includes:The driving voltage for reducing device improves shining for device
Efficiency improves the service life etc. of device.In order to realize OLED device performance continuous promotion, not only need from OLED device
The innovation of structure and manufacture craft formulates out higher performance OLED with greater need for the constantly research and innovation of oled light sulfate ferroelectric functional material
Functional material.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes, i.e. charge injection transmission from purposes
Material and luminescent material further can also inject charge into transmission material and be divided into electron injection transmission material and hole injection biography
Luminescent material can also be divided into main body luminescent material and dopant material by defeated material.In order to make high performance OLED photophores
Part, it is desirable that various organic functional materials have good photoelectric characteristic, for example, as charge transport materials, it is desirable that have good
Carrier mobility, high-vitrification conversion temperature etc., as luminescent layer material requirements material have good fluorescent quantum
Efficiency, material vapor deposition stability, HOMO/LUMO appropriate energy ranks etc..
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, is applied in industry
OLED device structure includes then a variety of film layers such as hole injection layer, hole transmission layer, luminescent layer, electron injecting layer, that is to say, that
Photoelectric functional material applied to OLED device includes at least hole-injecting material, hole mobile material, luminescent material, electronics note
Enter material etc., material type and collocation form have the characteristics that rich and multifarious.In addition, for the OLED devices of different structure
For part collocation, used photoelectric functional material has stronger selectivity, and identical material is in different structure device
Performance, it is also possible to completely totally different.
Currently, having been achieved for significant progress in terms of fluorescent material research, the demand of industrialization disclosure satisfy that;Tradition has
Machine fluorescent material can only be shone using 25% singlet exciton to be formed is electrically excited, and the internal quantum efficiency of device is relatively low (up to
25%) external quantum efficiency, is caused generally to be less than 5%;Especially in terms of blue lifetime, huge challenge is still remained.Cause
And the research and development of high efficiency, the fluorescent material of long-life is always the hot spot of industrialization.
In addition, in host-guest system system, using phosphor material or thermal excitation delayed fluorescence material (TADF) as
The OLED device of object, material of main part need high triplet energy state (T1), to prevent energy from returning main body from guest materials
Material improves the quantum efficiency of device.
Hot activation delayed fluorescence (TADF) material is the third developed after organic fluorescence materials and organic phosphorescent material
For luminous organic material.Such material generally has small poor (the △ E of singlet-tripletST), triplet excitons can lead to
Cross anti-intersystem crossing be transformed into singlet exciton shine.This can make full use of the singlet exciton for being electrically excited lower formation and three lines
The internal quantum efficiency of state exciton, device can reach 100%.Meanwhile material structure is controllable, property is stablized, cheap to be not necessarily to
Precious metal, in having a extensive future for the fields OLEDs.
Therefore, for current OLED shows the actual demand of Lighting Industry, the development of fluorescent material is also far from enough,
The requirement for lagging behind panel manufacturing enterprise, the organic functions fluorescent material as material enterprise development higher performance seem particularly heavy
It wants.
Invention content
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of organic electroluminescent compounds and its answers
With.The compounds of this invention has good external quantum efficiency, stability of material as the OLED device that emitting layer material is produced
And excitation purity, it disclosure satisfy that the requirement of panel manufacturing enterprise.
Technical scheme is as follows:
The applicant provides a kind of organic electroluminescent compounds of boracic, the structure such as general formula (1) of the compound
It is shown:
In general formula (1), R1~R9Independently be expressed as hydrogen, aryl, heteroaryl, alkyl, alkoxy or aryl amine;
X1、X2、X3Independently be expressed as O, S, N-R or general formula (2);
Wherein, the R in N-R is expressed as aryl, heteroaryl or aryl amine;
A1-A2The carbon atom number that is expressed as independently is the alkyl of 1-6, substitution or unsubstituted aryl, heteroaryl.
Preferably, the compound is indicated by general formula (3):
In general formula (3), R1~R9Expression hydrogen, aryl, heteroaryl, alkyl, alkoxy or aryl amine independently, still
It cannot be all shown as hydrogen;
A1、A2Independently be expressed as carbon atom number be 1-6 alkyl, substitution or unsubstituted aryl or heteroaryl
Base.
Preferably, the R1~R9Independently be expressed as hydrogen, substitution or unsubstituted diaryl-amine group, substitution or
The unsubstituted nitrogenous multicomponent heterocycle group of person, but hydrogen cannot be all shown as;
A1、A2Independently be expressed as carbon atom number be 1-6 alkyl, substitution or unsubstituted aryl or heteroaryl
Base.
Preferably, R in the general formula (1)1~R9It is at least one to be indicated using general formula (4):
In general formula (4), R10、R11The substituted or unsubstituted phenyl of expression independently, pyridyl group, dibiphenylyl, three
Phenyl, anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenylfluorenes
In base, carbazyl, benzo carbazole base, dibenzothiophene, bifurcation piperidinyl, indolocarbazole base, phenoxazine groups, Huo Sai oxazinyls
It is a kind of;R10、R11It is identical or different.
Preferably, R in the general formula (1)1~R9It is at least one to be indicated with general formula (5) or general formula (6):
In general formula (6), X1For oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution
One kind in the tertiary amine groups of substituted alkylidene, alkyl or aryl substitution;
R14、R15Independently be expressed as hydrogen, carbon atom 1-6 alkyl, substitution or for substituted phenyl, carbazyl,
Or it is indicated by general formula (7):
In general formula (7), R16、R17The substituted or unsubstituted phenyl of expression independently, pyridyl group, dibiphenylyl, three
Phenyl, anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenylfluorenes
One in base, carbazyl, benzo carbazole base, dibenzothiophene, bifurcation piperidinyl, indolocarbazole base, phenoxazine group, Sai oxazinyls
Kind;R16、R17It is identical or different.
Preferably, A in the general formula1-A2Being expressed as independently:
Any one of.
Preferably, the compound concrete structure is:
Middle any type.
The applicant additionally provides a kind of organic electroluminescence of the organic electroluminescent compounds containing the boracic
Part, the compound are applied to organic electroluminescent LED as luminescent layer material of main part or dopant material.
The present invention is beneficial to be had technical effect that:
Compound of the present invention can be applied to the making of OLED luminescent devices, and can obtain good device performance,
The compound as OLED luminescent devices independent emitting layer material or luminescent layer dopant material in use, device
Luminous efficiency, power efficiency and external quantum efficiency are greatly improved;Device color color purity be improved significantly, device lifetime obtains
To promotion.Compound of the present invention has good application effect in OLED luminescent devices, before having good industrialization
Scape.
The present invention using boron atom as core, by by different aromatic structures in connection form poly-ring aromatic compounds,
There is such material higher triplet (T1) can be used as material of main part;Meanwhile such material is generally with small
Poor (the △ E of singlet-tripletST), triplet excitons can be transformed into singlet exciton by anti-intersystem crossing and be shone,
Effectively improve device efficiency.There is such material higher glass transition temperature and decomposition temperature to apply to organic light-emitting diodes
Guan Zhong can effectively improve the service life of device.
Description of the drawings
Fig. 1 is the schematic diagram of OLED device made of the compounds of this invention.
In figure:1, transparent substrate layer, 2, ito anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electricity
Sub- transport layer, 7, electron injecting layer, 8, cathode reflection electrode layer.
Specific implementation mode
In order to more be apparent from the technological means and practical purpose of the present invention, by enumerating embodiment and comparative example,
It is aided with picture simultaneously to be illustrated.
Embodiment 1 (compound 01)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate As, 0.025mol phenyl boric acids, 0.05 gram of pd is added in the four-hole bottle of 250ml
(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethyl alcohol, water is heated to reflux 20 hours, and the reaction was complete;Natural cooling, mistake
Filter, filtrate revolving, crosses silicagel column, uses toluene:Ethyl alcohol=2:1 (volume ratio) mixed solvent is beaten, and it is solid that white is obtained after recrystallization
Body, purity (HPLC) are 97.8%, yield 66.6%.
Elemental analysis structure (molecular formula C39H35B):Theoretical value C, 91.04;H,6.86;N,2.10;
Test value:C,90.92;H,6.95;N,2.13.
Embodiment 2 (compound 08)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate As, 0.025mol dibenzofurans -4- boron is added in the four-hole bottle of 250ml
Acid, 0.05 gram of pd (pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethyl alcohol, water is heated to reflux 20 hours, and the reaction was complete;
Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=2:1 (volume ratio) mixed solvent is beaten, after recrystallization
White solid is obtained, purity (HPLC) is 98.3%, yield 64.6%.
Elemental analysis structure (molecular formula C51H39BO2):Theoretical value C, 88.18;H,5.66;B,1.56;O, 4.61 test values:
C,88.25H,5.53;B,1.49;O,4.73
Embodiment 3 (compound 10)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate As, bis- (3, the 4- dimethyl benzenes of 0.025mol are added in the four-hole bottle of 250ml
Base) amine, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene, heating
Reflux 20 hours, the reaction was complete;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio)
Mixed solvent is beaten, and white solid is obtained after recrystallization, and purity (HPLC) is 97.6%, yield 64.5%.
Elemental analysis structure (molecular formula C59H61BN2):Theoretical value C, 87.60;H,7.60;N,3.46;B, 1.34 test values:
C,87.54;H,7.54;N,3.61;B,1.31
Embodiment 4 (compound 15)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate As, 0.025mol 3,6- di-t-butyl clicks is added in the four-hole bottle of 250ml
Azoles, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene, are heated to reflux
20 hours, the reaction was complete;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixes
Solvent is beaten, and white solid is obtained after recrystallization, and purity (HPLC) is 97.2%, yield 66.5%.
Elemental analysis structure (molecular formula C67H73BN2):Theoretical value C, 87.74;H,8.02;N,3.05;B, 1.18 test values:
C,87.55;H,8.05;N,3.02;B,1.38
Embodiment 5 (compound 18)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate As, 0.025mol 3,6- di-t-butyl clicks is added in the four-hole bottle of 250ml
Azoles, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene, are heated to reflux
20 hours, the reaction was complete;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixes
Solvent is beaten, and white solid is obtained after recrystallization, and purity (HPLC) is 97.2%, yield 66.5%.
Elemental analysis structure (molecular formula C99H77BN6):Theoretical value C, 87.33;H,5.70;N,6.17;B, 0.97 test value:
C,87.25;H,5.58;N,6.14;B,1.03
Embodiment 6 (compound 31)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediate Bs, 0.025mol phenyl boric acids, 0.05 gram of pd is added in the four-hole bottle of 250ml
(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethyl alcohol, water is heated to reflux 20 hours, and the reaction was complete;Natural cooling, mistake
Filter, filtrate revolving, crosses silicagel column, uses toluene:Ethyl alcohol=2:1 (volume ratio) mixed solvent is beaten, and it is solid that white is obtained after recrystallization
Body, purity (HPLC) are 98.3%, yield 62.6%.
Elemental analysis structure (molecular formula C36H29BO):Theoretical value C, 88.53;H,5.98;O,3.28;B,2.21
Test value:C,88.42;H,6.07;O,3.33;B,2.18
Embodiment 7 (compound 36)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates C, 0.025mol4- biphenylboronic acid is added in the four-hole bottle of 250ml, 0.05 gram
pd(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethyl alcohol, water is heated to reflux 20 hours, and the reaction was complete;Natural cooling,
Filtering, filtrate revolving, crosses silicagel column, uses toluene:Ethyl alcohol=2:1 (volume ratio) mixed solvent is beaten, and white is obtained after recrystallization
Solid, purity (HPLC) are 97.5%, yield 61.8%.
Elemental analysis structure (molecular formula C42H25BO3):Theoretical value C, 85.72;H,4.28;O,8.16;B, 1.84 test values:
C,85.65;H,4.21O,8.25;B,1.89
Embodiment 8 (compound 44)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates D, 0.025mol compound 2, uncle 0.03mol is added in the four-hole bottle of 250ml
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene is heated to reflux 20 hours, reaction
Completely;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixed solvent is beaten, weight
White solid is obtained after crystallization, purity (HPLC) is 97.6%, yield 64.8%.
Elemental analysis structure (molecular formula C59H53BN2S2):Theoretical value C, 81.92;H,6.18;N,3.24;B,1.25;S,
7.41
Test value:C,81.82;H,6.24;N,3.14;B,1.29;S,7.51
Embodiment 9 (compound 49)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates C, 0.025mol4- biphenylboronic acid is added in the four-hole bottle of 250ml, 0.05 gram
pd(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethyl alcohol, water is heated to reflux 20 hours, and the reaction was complete;Natural cooling,
Filtering, filtrate revolving, crosses silicagel column, uses toluene:Ethyl alcohol=2:1 (volume ratio) mixed solvent is beaten, and white is obtained after recrystallization
Solid, purity (HPLC) are 97.5%, yield 61.8%.
Elemental analysis structure (molecular formula C42H34BN):Theoretical value C, 89.51;H,6.08;N,2.49;B,1.92
Test value:C,89.46;H,6.02;N,2.44;B,2.08
Embodiment 10 (compound 55)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates F, 0.012mol compound 2, uncle 0.03mol is added in the four-hole bottle of 250ml
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene are heated to reflux 20 hours, reaction
Completely;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixed solvent is beaten, weight
White solid is obtained after crystallization, purity (HPLC) is 98.6%, yield 61.8%.
Elemental analysis structure (molecular formula C44H37BN2O2):Theoretical value C, 83.02;H,5.86;N,4.40;B,1.70;O,
5.03
Test value:C,83.15;H,5.91;N,4.47;B,1.64;O,4.83
Embodiment 11 (compound 59)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates F, 0.012mol compound 3, uncle 0.03mol is added in the four-hole bottle of 250ml
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene are heated to reflux 20 hours, reaction
Completely;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixed solvent is beaten, weight
White solid is obtained after crystallization, purity (HPLC) is 97.8%, yield 62.1%.
Elemental analysis structure (molecular formula C60H39BN4O2):Theoretical value C, 83.91;H,4.58;N,6.52;B,1.26;O,
3.73
Test value:C,83.78;H,4.63;N,6.47;B,1.21;O,3.91
Embodiment 12 (compound 69)
The specific synthetic route of the compound is now provided:
Under nitrogen protection, 0.01mol intermediates G, 0.025mol phenoxazine, uncle 0.03mol is added in the four-hole bottle of 250ml
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 200ml toluene are heated to reflux 20 hours, reaction
Completely;Natural cooling, filtering, filtrate revolving cross silicagel column, use toluene:Ethyl alcohol=3:1 (volume ratio) mixed solvent is beaten, weight
White solid is obtained after crystallization, purity (HPLC) is 98.3%, yield 64.7%.
Elemental analysis structure (molecular formula C48H28BN3O4):Theoretical value C, 79.90;H,3.91;N,5.82;B,1.50;O,
8.87
Test value:C,79.75;H,3.93;N,5.79;B,1.46;O,9.07
The compounds of this invention can be used as luminous layer main body or dopant material to use, to the compounds of this invention 10, chemical combination
Object 15, current material mCP carry out hot property, the measurement of luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability respectively,
Testing result is as shown in table 1.
Table 1
Note:Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min;λPLIt is sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan
SR-3 spectroradiometers measure;Φ f are that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics
Fiber spectrometer, the test solid fluorescence amount of C-701 integrating spheres and marine optics LLS-LED the light sources composition of Lan Fei companies of the U.S.
Sub- efficiency test system, reference literature Adv.Mater.1997,9,
The method of 230-232 is measured);Cyclic voltammetric stability is to observe the oxidation of material also by cyclic voltammetry
Former characteristic is identified;Test condition:It is 2 that test sample, which is dissolved in volume ratio,:1 dichloromethane and acetonitrile mixed solvent is dense
1mg/mL is spent, electrolyte is the tetrabutyl ammonium tetrafluoroborate of 0.1M or the organic solution of hexafluorophosphate.Reference electrode
It is Ag/Ag+ electrodes, is titanium plate to electrode, working electrode is ITO electrode, and cycle-index is 20 times.
By upper table data it is found that the compounds of this invention has higher thermal stability, suitable luminescent spectrum, higher Φ
F so that get a promotion as the OLED device efficiency of dopant material and service life using the compounds of this invention.
Below by way of comparative example 1,2 and embodiment 13~24 material that the present invention will be described in detail synthesizes in OLED device
Application effect.For the embodiment 13~24 compared with comparative example 1,2, the manufacture craft of the device is identical, and is adopted
It is also consistent with the film thickness of identical baseplate material and electrode material, electrode material, except that being made in device
Some materials have carried out some adjustment, and comparative example 1,2 has used part OLED material of the present invention.
Comparative example 1
Transparent glass substrate 1 uses transparent material.Ito anode layer 2 (film thickness 150nm) is washed, i.e., successively into
Ultraviolet-ozone washing is carried out after row neutralizing treatment, pure water, drying again to remove the organic residue on the transparent surfaces ITO.
On the ito anode layer 2 after having carried out above-mentioned washing, using vacuum deposition apparatus, HAT-CN, film thickness is deposited
For 10nm, this layer of organic material is used as hole injection layer 3.And then TCTA (4,4', 4 "-three (clicks of 60nm thickness are deposited
Azoles -9- bases) triphenylamine) it is used as hole transmission layer 4.
After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent devices is made, structure includes OLED hairs
5 used material mCP of photosphere【Two -9H- carbazoles of 9,9'- (1,3- phenyl)】As material of main part, GD-19 as dopant material,
Doping ratio is 5% weight ratio, and luminescent layer film thickness is 25nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are Alq3(8-hydroxyquinoline aluminium).The material
The vacuum evaporation film thickness of material is 30nm, this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that film thickness is 80nm is made, this layer is cathode
Reflection electrode layer 8 uses.Layers of material structure is as follows:
Comparative example 2
Comparative example 2 and comparative example 1 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes into Ir
(ppy)3.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 13
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes into chemical combination
Object 01.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 14
The present embodiment is with comparative example 1 with place:MCP in the luminescent layer 5 of OLED luminescent devices changes into compound
08.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 15
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes compound
15.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 16
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes into chemical combination
Object 31.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 17
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes into chemical combination
Object 36.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 18
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes into chemical combination
Object 49.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Embodiment 19
The present embodiment and comparative example 1 the difference is that:MCP in the luminescent layer 5 of OLED luminescent devices changes into chemical combination
Object 55.Made OLED light emitting device structures are as shown in table 2, and test result is as shown in table 3.
Table 2
Table 3
Embodiment 20
The present embodiment and comparative example 2 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes chemical combination
Object 10.Made OLED light emitting device structures are as shown in table 4, and test result is as shown in table 5.
Embodiment 21
The present embodiment and comparative example 2 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes chemical combination
Object 18.Made OLED light emitting device structures are as shown in table 4, and test result is as shown in table 5.
Embodiment 22
The present embodiment and comparative example 2 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes chemical combination
Object 44.Made OLED light emitting device structures are as shown in table 4, and test result is as shown in table 5.
Embodiment 23
The present embodiment and comparative example 2 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes chemical combination
Object 59.Made OLED light emitting device structures are as shown in table 4, and test result is as shown in table 5.
Embodiment 24
The present embodiment and comparative example 2 the difference is that:GD-19 in the luminescent layer 5 of OLED luminescent devices changes chemical combination
Object 69.Made OLED light emitting device structures are as shown in table 4, and test result is as shown in table 5.
Table 4
Table 5
Compound of the present invention is as material of main part or dopant material application it can be seen from the result of table 3 and table 5
It is made in OLED luminescent devices, and good device performance can be obtained.Luminous efficiency, the external quantum efficiency of device obtain
Very big improvement;Device lifetime is promoted clearly simultaneously.Compound of the present invention has good in OLED luminescent devices
Application effect, and there is good industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.
Claims (7)
1. a kind of organic electroluminescent compounds of boracic, it is characterised in that shown in the structure of the compound such as general formula (1):
In general formula (1), R1~R9Independently be expressed as hydrogen, aryl, heteroaryl, alkyl, alkoxy or aryl amine;
X1、X2、X3Independently be expressed as O, S or general formula (2);
A1-A2The carbon atom number that is expressed as independently is the alkyl of 1-6, substitution or unsubstituted aryl, heteroaryl.
2. compound according to claim 1, it is characterised in that the R1~R9Independently be expressed as hydrogen, substitution or
The unsubstituted diaryl-amine group of person, substitution or unsubstituted nitrogenous multicomponent heterocycle group.
3. compound according to claim 1, it is characterised in that R in the general formula (1)1~R9It is at least one to use general formula
(4) it indicates:
In general formula (4), R10、R11The substituted or unsubstituted phenyl of expression independently, pyridyl group, dibiphenylyl, terphenyl,
Anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, click
One kind in oxazolyl, benzo carbazole base, dibenzothiophene, bifurcation piperidinyl, indolocarbazole base, phenoxazine groups, Huo Sai oxazinyls;
R10、R11It is identical or different.
4. compound according to claim 1, it is characterised in that R in the general formula (1)1~R9It is at least one to use general formula (5)
Or general formula (6) indicates:
In general formula (6), X1For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of linear or branched alkyl group substitution, aryl substitution
Alkylidene, alkyl or aryl substitution tertiary amine groups in one kind;
R14、R15Independently be expressed as hydrogen, carbon atom 1-6 alkyl, substitution or for substituted phenyl, carbazyl or
It is indicated by general formula (7):
In general formula (7), R16、R17The substituted or unsubstituted phenyl of expression independently, pyridyl group, dibiphenylyl, terphenyl,
Anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, click
One kind in oxazolyl, benzo carbazole base, dibenzothiophene, bifurcation piperidinyl, indolocarbazole base, phenoxazine group, Sai oxazinyls;
R16、R17It is identical or different.
5. compound according to claim 1, it is characterised in that A in the general formula1-A2Being expressed as independently:
Any one of.
6. compound according to claim 1, it is characterised in that the compound concrete structure is:
Middle any type.
7. a kind of organic electroluminescence device of the organic electroluminescent compounds containing the boracic, it is characterised in that describedization
It closes object and is applied to organic electroluminescent LED as luminescent layer material of main part or dopant material.
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CN108586507B (en) | 2020-11-17 |
CN108586507A (en) | 2018-09-28 |
CN106467553B (en) | 2019-08-23 |
CN108610357A (en) | 2018-10-02 |
CN108530475A (en) | 2018-09-14 |
CN108409769A (en) | 2018-08-17 |
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