CN109206367A - A kind of organic electroluminescence device and display - Google Patents
A kind of organic electroluminescence device and display Download PDFInfo
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- CN109206367A CN109206367A CN201811069114.6A CN201811069114A CN109206367A CN 109206367 A CN109206367 A CN 109206367A CN 201811069114 A CN201811069114 A CN 201811069114A CN 109206367 A CN109206367 A CN 109206367A
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- electroluminescence device
- organic electroluminescence
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims description 41
- 239000000758 substrate Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- -1 indazole compound Chemical class 0.000 claims description 6
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 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 1
- 230000005540 biological transmission Effects 0.000 abstract description 15
- 238000002347 injection Methods 0.000 abstract description 15
- 239000007924 injection Substances 0.000 abstract description 15
- 239000011368 organic material Substances 0.000 abstract description 15
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 62
- 238000007738 vacuum evaporation Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000027756 respiratory electron transport chain Effects 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000005611 electricity Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 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 5
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical class [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FICOFYGYCQEHLR-UHFFFAOYSA-N 2,3-diazatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene Chemical class C1=CC2=CC=CC(NN3)=C2C3=C1 FICOFYGYCQEHLR-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 238000012545 processing Methods 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
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical class COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
- H10K85/649—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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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to field of display technology, more particularly to a kind of dihydrobenzo indazole class electroluminescent organic material, organic electroluminescence device and display.Shown in compound according to the present invention such as formula (A):
Description
Technical field
The present invention relates to field of display technology, more particularly to a kind of dihydrobenzo indazole class electroluminescent organic material,
Organic electroluminescence device and display.
Background technique
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as novel
Plate display is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master
It is dynamic shine, luminescent color is continuously adjustable, at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, gives birth to
Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair
Luminescent material, electroluminescent organic material have the advantage that organic material processing performance is good, can pass through vapor deposition or the side of spin coating
Method forms a film on any substrate；The diversity of organic molecular structure allow to by Molecular Design and the method for modification come
Adjust thermal stability, mechanical performance, the luminous and electric conductivity of organic material, the space so that material is significantly improved.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials
Recombination.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued in organic semiconductor, the transmission of carrier is normal
It is described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material
The difficulty of charge injection and transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer
Number, and so that different organic layers is played the part of different device layers, such as the functional material having can promote electronics from cathode
Injection, some functional materials can promote hole to inject from anode, and some materials can promote the transmission of charge, and some materials are then
It can play the role of stopping electronics or hole transport, the hair of most important various colors certainly in organic electroluminescence device
Luminescent material will also achieve the purpose that match with adjacent functional material, therefore, the organic electroluminescence device of excellent in efficiency service life length
Usually device architecture and various organic materials optimization collocation as a result, this is just that chemists design and develop various structures
Functionalization material provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode, electron injecting layer, electronics being arranged successively from top to bottom
Transport layer (Electron transport Layer, abbreviation ETL), organic luminous layer (Emitting Layer, abbreviation EML),
Hole transmission layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic light emission
The formation probability of exciton is improved in layer as far as possible, therefore the organic luminous layer of organic electroluminescence device and electronics adjacent thereto pass
The material of defeated layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And it is in the prior art
The material of main part of material or organic luminous layer that electron transfer layer is used makes organic electroluminescence device driving electricity with higher
Pressure and lower luminous efficiency.
Summary of the invention
The present invention provides a kind of dihydrobenzo indazole class electroluminescent organic material, include the organic electroluminescence of the compound
Luminescent device and display device with the organic electroluminescence device, to solve organic electroluminescence device in the prior art
High driving voltage and the problem of low luminous efficiency.
According to an aspect of the present invention, a kind of dihydrobenzo indazole class electroluminescent organic material, the compound are provided
As shown in formula (A):
Wherein Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from the aryl that carbon atom number is 6-30；The Ar1,
Aliphatic alkyl that Ar2, Ar3, Ar4, Ar5 can be 1~20 by one or more carbon atom number, carbon atom number 1
~20 aliphatic alkoxy, the aryl that carbon atom number is 6~30, trimethyl silicon substrate replace, the substitution can be it is monosubstituted,
It is disubstituted, polysubstituted.
Further, Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from phenyl, xenyl, naphthalene, fluorenyl, anthracene
It is base, phenanthryl, indeno fluorenyl, triphenylene, fluoranthene base, benzo anthryl, benzo fluorenyl, Spirofluorene-based.
Preferably, Ar1, Ar2Selected from phenyl, Ar1, Ar2Contraposition can by carbon atom number be 1~20 aliphatic alkyl,
Carbon atom number be 1~20 aliphatic alkoxy, trimethyl silicon substrate replace, it is described substitution can be it is monosubstituted, disubstituted, take more
Generation.
It is furthermore preferred that the compounds of this invention is selected from flowering structure:
Meanwhile the present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device contains this hair
The bright dihydrobenzo indazole class electroluminescent organic material.
Further, the hole transport layer material of organic electroluminescence device is dihydrobenzo indazole class of the present invention
Electroluminescent organic material.
In other embodiment, the hole injection layer material of organic electroluminescence device is dihydrobenzo of the present invention
Indazole class electroluminescent organic material.
Meanwhile the present invention also provides a kind of displays, contain organic electroluminescence device of the invention.
Meanwhile the present invention also provides electronic equipment, the electronic equipment display includes organic electroluminescence hair of the invention
Optical device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet computer, has electronical display function
Electronic entrance ticket, the onboard instruments etc. of energy.
Beneficial effects of the present invention are as follows:
Compound provided by the invention is used in the hole transmission layer or/and hole injection layer of organic electroluminescence device,
It improves the luminous efficiency of organic electroluminescence device, reduce the driving voltage of organic electroluminescence device.
Specific embodiment
Specific embodiment is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with
Invention is further explained and description for specific embodiment.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below
The present invention is further described.
The synthesis of 1 compound P-1 of embodiment
It is as follows to synthesize equation:
(1) synthesis of intermediate M-1
In 1000 milliliters of there-necked flask, under nitrogen protection, 500 milliliters of dry toluene, 37.6 grams are added
(0.22mol) 4- toluene bromide, 15.6 grams of (0.1mol) 1,2- dihydrobenzo [cd] indazoles, 28.8 grams of (0.3mol) sodium tert-butoxides,
1.26 grams (0.0022mol) bis- (dibenzalacetone) palladiums, 4.4 grams of (0.0022mol) 10% tri-tert-butylphosphine toluene it is molten
Liquid is down to room temperature after being heated to back flow reaction 8 hours, water, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid
After magnesium is dry, with silica gel post separation, use petroleum ether: ethyl acetate (volume ratio 5:1) is eluted as eluant, eluent, obtains formula
18.9 grams of product shown in M-1, yield 56.25%.
To obtained compound M-1, Mass Spectrometer Method, product m/e:336 are carried out.
It is as follows to obtained compound M-1 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram:
1HNMR (500MHz, CDCl3): δ 8.35 (m, 2H), δ 7.88 (m, 4H), δ 7.65 (m, 6H), δ 7.28 (d, 2H), δ
2.45 (s, 6H).
(2) synthesis of intermediate M-2
In 500 milliliters of there-necked flasks, compound shown in 3.36 grams of (0.01mol) formula M-1 of addition, 30 milliliters of methylene chloride, 0.2
Gram iron powder is cooled to 0~5 DEG C, and 3 milliliters of dichloromethane solutions of 1.76 grams of (0.011mol) bromines are added dropwise.Drop finishes slowly heating
It reacts 4 hours, cools down to 25 DEG C, washing, solution of sodium bisulfite washing, silica gel column chromatography point after organic layer magnesium sulfate is dry
From petroleum ether: ethyl acetate (volume ratio 50:1) is eluted as eluant, eluent, obtains 1.65 grams of product shown in formula M-2,
Yield is 39.76%.
To obtained compound M-2, Mass Spectrometer Method is carried out, product m/e:414,416.
It is as follows to obtained compound M-2 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram: 1HNMR
(500MHz, CDCl3): δ 8.34 (m, 1H), δ 8.07 (d, 1H), δ 7.89 (d, 4H), δ 7.61 (m, 5H), δ 7.55 (d, 1H), δ
7.28 (m, 1H), δ 2.45 (s, 6H).
(3) synthesis of intermediate M-3:
100 milliliters of dry tetrahydrofurans, 4.15 grams of (0.01mol) formula M-2 are added in 500 milliliters of there-necked flasks, nitrogen protection
Shown compound, is cooled to -78 DEG C, and the butyl lithium solution of 7.5 milliliters of (0.012mol) 1.6M is slowly added dropwise, finishes in -78 DEG C
It is kept for 1 hour, is slowly added to 1.56 grams of (0.015mol) trimethylborates, be to slowly warm up to 25 DEG C and kept for 2 hours, add ammonium chloride
Solution liquid separation, organic layer are concentrated to dryness, and obtain compound shown in formula M-3, without further purifying, directly carry out the next step.
(4) synthesis of intermediate M-4:
500 milliliters of there-necked flasks, nitrogen protection are added 30 milliliters of toluene, 30 milliliters of ethyl alcohol, 20 milliliters of water, walk not in addition
Through it is further proposed that formula M-3 shown in compound, add 7.08 grams of (0.03mol) Isosorbide-5-Nitrae-dibromobenzenes, 0.12 gram
(0.0001mol) tetrakis triphenylphosphine palladium, 2.76 grams of (0.02mol) potassium carbonate, is warming up to back flow reaction 8 hours, is down to room temperature,
Water is added, liquid separation, neutrality is washed with water in organic layer, with anhydrous magnesium sulfate it is dry after, with silica gel post separation, with petroleum ether: second
Acetoacetic ester (volume ratio 50:1) is eluted as eluant, eluent, and obtaining 1.66 grams of product, yield shown in formula M-4 is
33.8%.
To obtained compound M-4, Mass Spectrometer Method is carried out, product m/e:490,492.
(5) synthesis of product P-1:
In 500 milliliters of there-necked flask, under nitrogen protection, 100 milliliters of dry toluene, 4.91 grams are added
Compound shown in (0.01mol) M-4,2.03 grams of (0.012mol) diphenylamines, 1.25 grams of (0.013mol) sodium tert-butoxides, 0.126
Gram (0.00022mol) bis- (dibenzalacetone) palladiums, 0.44 gram of (0.00022mol) 10% tri-tert-butylphosphine toluene it is molten
Liquid is down to room temperature after being heated to back flow reaction 8 hours, water, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid
After magnesium is dry, with silica gel post separation, use petroleum ether: ethyl acetate (volume ratio 10:1) is eluted as eluant, eluent, is obtained
3.91 grams of product shown in formula P-1, yield 67.4%.
To obtained compound P-1, Mass Spectrometer Method, product m/e:579 are carried out.
It is as follows to obtained compound P-1 row nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram:
1HNMR (500MHz, CDCl3): δ 8.33 (m, 1H), δ 8.28 (d, 1H), δ 7.90 (m, 4H), δ 7.62 (m, 5H), δ
7.55 (m, 2H), δ 7.37 (m, 2H), δ 7.32~7.22 (m, 6H), δ 7.09 (m, 4H), δ 7.02 (m, 2H), δ 2.46 (s, 6H).
Embodiment 2
4- toluene bromide therein is only changed into the bromo-derivative of corresponding type by the synthesis of reference compound P-1 as needed,
It changes Isosorbide-5-Nitrae-dibromobenzene therein into corresponding two bromo-derivative, changes diphenylamines therein into corresponding aromatic amine, preparation is following
Compound has carried out Mass Spectrometer Method to obtained compound.
The type, the type of two bromo-derivatives, the type of aromatic amine of bromo-derivative used and gained compound in preparation process
Mass spectrometric data see the table below:
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device
Hole injection layer or/and hole transport layer material are according to the compound of the present invention.
The typical structure of organic electroluminescence device are as follows: substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light
Layer is also possible to multi-luminescent layer.
Wherein, the substrate in conventional organic electroluminescence device can be used in substrate, such as: glass or plastics.Anode can be with
Using transparent high conductivity material, such as: indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable that there is height
Thermal stability (high Tg), have a lesser potential barrier with anode, can vacuum evaporation form pin-hole free films.Commonly HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable that there is height
Thermal stability (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Commonly HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated
Material, material of main part need to have following characteristics: reversible electrochemical redox current potential, with adjacent hole transmission layer and electronics
The HOMO energy level and lumo energy that transport layer matches, the good and hole to match and electron transport ability are good high
Thermal stability and film forming, and suitable singlet or triplet state energy gap are used to control exciton in luminescent layer, there are also with phase
Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer is needed by taking dyestuff as an example
Have following characteristics: there is high fluorescence or phosphorescence quantum efficiency；The absorption spectrum of dyestuff and the emission spectrum of main body have
Overlapping, i.e. main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue to the greatest extent may be used
Can be narrow, with the excitation purity obtained；Stability is good, is able to carry out vapor deposition etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM
There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy level and LUMO (Lowest Unoccupied
Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with
Hole blocking ability；Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4-
(1 '-naphthalene) -5- benzene -1,2,4- triazole) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazole) benzene) or be derived from this three
Any two kinds of collocation of kind material.
According to another aspect of the present invention, a kind of display is provided, which includes Organic Electricity according to the present invention
Electroluminescence device.
According to another aspect of the present invention, a kind of electronic equipment is provided, the electronic equipment display includes the present invention
The organic electroluminescence device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, plate electricity
Brain, the electronic entrance ticket with electronic display function.
It can be seen that compound according to the present invention, organic electroluminescence device, display and the electricity with display device
The optional factor of sub- device is more, and claim according to the present invention can be combined into different embodiments.Implementation of the invention
Example is not intended as limitation of the present invention only as to specific descriptions of the invention.Below in conjunction with contain chemical combination of the invention
The present invention is described further as embodiment for the organic electroluminescence device of object.
Different materials specific structure used in the present invention is seen below:
Embodiment 3
Hole-injecting material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole-injecting material select HIL02.
Organic electroluminescence device structure are as follows: ITO/ hole injection layer (100nm)/NPB (40nm)/EM1 (30nm)/Alq3
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode
Hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 100nm；
Vacuum evaporation NPB is as hole transmission layer on hole injection layer, and evaporation rate 0.1nm/s, film thickness, which is deposited, is
40nm；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm；
Electron transfer layer of the vacuum evaporation Alq3 as organic electroluminescence device on organic luminous layer；Speed is deposited in it
Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 1:
Table 1
As can be seen that under identical brightness conditions, using the compound of the present invention as made from hole-injecting material
Organic electroluminescence device with using HIL02 as organic electroluminescence device made from hole-injecting material compared with, with compared with
Low driving voltage and higher current efficiency.
Embodiment 4
Hole mobile material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole mobile material select NPB.
Organic electroluminescence device structure are as follows: ITO/HIL02 (100nm)/hole transmission layer (40nm)/EM1 (30nm)/
Alq3(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode
Hole HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness；
Vacuum evaporation material of the present invention and NPB are distinguished on hole injection layer as hole transmission layer, evaporation rate is
0.1nm/s, vapor deposition film thickness are 40nm；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm；
Electron transfer layer of the vacuum evaporation Alq3 as organic electroluminescence device on organic luminous layer；Speed is deposited in it
Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 2:
Table 2
As can be seen that under identical brightness conditions, using the compound of the present invention as made from hole mobile material
Organic electroluminescence device has lower compared with use NPB is as organic electroluminescence device made from hole mobile material
Driving voltage and higher current efficiency.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to include these modifications and variations.
Claims (8)
1. a kind of organic electroluminescence device contains dihydrobenzo indazole compound shown in formula (A):
Wherein Ar1, Ar2, Ar3, Ar4, Ar5 are independently selected from the aryl that carbon atom number is 6-30；Ar1, the Ar2,
Aliphatic alkyl that Ar3, Ar4, Ar5 can be 1~20 by one or more carbon atom number, carbon atom number are 1~20
Aliphatic alkoxy, carbon atom number be 6~30 aryl, trimethyl silicon substrate replace.
2. organic electroluminescence device according to claim 1, which is characterized in that Ar1, Ar2, Ar3, Ar4, Ar5 difference are only
Vertical is selected from phenyl, xenyl, naphthalene, fluorenyl, anthryl, phenanthryl, indeno fluorenyl, triphenylene, fluoranthene base, benzo anthryl, benzene
And it is fluorenyl, Spirofluorene-based.
3. organic electroluminescence device according to claim 1, wherein Ar1, Ar2Selected from phenyl, Ar1, Ar2Contraposition can be with
By carbon atom number be 1~20 aliphatic alkyl, carbon atom number be 1~20 aliphatic alkoxy, trimethyl silicon substrate replaces.
4. organic electroluminescence device according to claim 1, wherein compound shown in formula (A) is selected from:
5. organic electroluminescence device according to claim 1, which is characterized in that the sky of the organic electroluminescence device
It is compound shown in formula (A) that layer material is injected in cave.
6. organic electroluminescence device according to claim 1, which is characterized in that the sky of the organic electroluminescence device
It is compound shown in formula (A) that layer material is transmitted in cave.
7. a kind of display, which is characterized in that including the organic electroluminescence device as described in claim 1-6 is any.
8. a kind of electronic equipment, the electronic equipment display includes the organic electroluminescent as described in claim 1-6 is any
Device；
The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet computer, has electronic display function
Electronic entrance ticket, onboard instruments.
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| CN114702432A (en) * | 2022-04-01 | 2022-07-05 | 上海钥熠电子科技有限公司 | Compound containing acenaphthene and application thereof in organic electroluminescent device |
| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114702432A (en) * | 2022-04-01 | 2022-07-05 | 上海钥熠电子科技有限公司 | Compound containing acenaphthene and application thereof in organic electroluminescent device |
| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
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