CN104617224B - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
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- CN104617224B CN104617224B CN201510080324.5A CN201510080324A CN104617224B CN 104617224 B CN104617224 B CN 104617224B CN 201510080324 A CN201510080324 A CN 201510080324A CN 104617224 B CN104617224 B CN 104617224B
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- electroluminescence device
- organic electroluminescence
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 37
- 239000010410 layer Substances 0.000 claims abstract description 123
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 230000005540 biological transmission Effects 0.000 claims abstract description 23
- 239000012044 organic layer Substances 0.000 claims abstract description 22
- 238000002347 injection Methods 0.000 claims abstract description 15
- 239000007924 injection Substances 0.000 claims abstract description 15
- 230000004888 barrier function Effects 0.000 claims abstract description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 37
- -1 normal-butyl Chemical group 0.000 claims description 29
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract 1
- 239000000463 material Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
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- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
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- 239000000047 product Substances 0.000 description 8
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- 230000000903 blocking effect Effects 0.000 description 3
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- 238000004440 column chromatography Methods 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
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- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
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- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 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
- 150000003918 triazines Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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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
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/302—Details of OLEDs of OLED structures
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- Chemical & Material Sciences (AREA)
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescence device. The organic electroluminescence device comprises a positive pole, a negative pole and an organic layer, wherein the organic layer contains one or more than one of a hole injection layer, a hole transmission layer, a luminescence layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic electroluminescence device is characterized in that at least one layer in the organic layer comprises a compound based on a carbazole derivative, which has the structure formula (I) in the specification.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, more particularly to a kind of organic electroluminescence device.
Technical background
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared from, three layers of organic electroluminescence device of a classics include hole transmission layer, luminescent layer
And electron transfer layer.By anode produce hole Jing hole transmission layers combined with the electronics Jing electron transfer layers produced by negative electrode
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
The light of the various needs of section transmitting.
Organic electroluminescence device as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
The particular advantages such as display floater and environmental friendliness, can apply on flat-panel monitor and a new generation's illumination, it is also possible to as
The backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device has industrially been applied, such as
Used as screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.Run in applied voltage additionally, due to OLED
When, Joule heat can be produced so that organic material is susceptible to crystallization, have impact on life-span and the efficiency of device, therefore, it is also desirable to
The electroluminescent organic material of exploitation stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical restriction of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application is also greatly carried
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence is needed using host-guest system technology, conventional as phosphorus
The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work
For material of main part when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
Easily transmit and the characteristic of the difficult flowing of electronics in the hole of CBP so that the charge unbalance of luminescent layer, as a result reduce the effect of device
Rate.
The content of the invention
Present invention firstly provides a kind of compound based on carbazole derivates, it is the compound with following structure Formulas I：
Wherein L be sky, singly-bound, the substituted or unsubstituted alkyl of C1-C8, the substituted or unsubstituted aryl of C6-C30,
The replacement of C3-C30 or unsubstituted heteroaryl；
Wherein X1And X2Independently it is expressed as CH or N；
Wherein Ar1Substituted or unsubstituted alkyl, the replacement of C6-C60 or unsubstituted aryl selected from C1-C12,
Replacement either unsubstituted thiazolinyl, the replacement of C2-C8 or not of the replacement of C3-C60 either unsubstituted heteroaryl, C2-C8
Substituted alkynyl；
Wherein Ar2Selected from for following structural：
Wherein A, B, C, D, E and F are independently selected from O, S, NAr3Or CAr4Ar5；
Wherein, Ar3、Ar4And Ar5Separately selected from substituted or unsubstituted alkyl, the alcoxyl of C1-C8 of C1-C8
Base, C6-C30 replacement either unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or
The unsubstituted thiazolinyl of person, the replacement of C2-C8 or unsubstituted alkynyl；
Wherein preferred mode is：
L is selected from phenyl, by the alkyl-substituted phenyl of C1-C4, naphthyl, by the alkyl-substituted naphthyls of C1-C4, xenyl or quilt
The alkyl-substituted xenyls of C1-C4；
Ar1、Ar3、Ar4And Ar5Separately selected from alkyl, the alkoxyl of C1-C8, phenyl, naphthyl, the anthracene of C1-C8
Base, phenanthryl, pyrenyl, perylene bases, fluoranthene base, (9,9- dialkyl group) fluorenyl, (replacements of 9,9- bis- or unsubstituted aryl) fluorenyl, 9,
9- is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases,
Quinolyl, triaromatic amine base, carbazyl；
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene bases, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,
The replacements of 9- bis- or unsubstituted aryl) it is fluorenyl, 9,9- Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, phonetic
Piperidinyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl further can be taken by the aryl of the alkyl of C1-C4 or C6-C30
Generation；
Wherein described alkyl can be for straight chain, side chain or for cycloalkyl；
Further preferred mode is：
L is selected from phenyl, naphthyl, xenyl；
Wherein Ar1、Ar3、Ar4And Ar5Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, quilt
The substituted or unsubstituted following aryl of C1-C4 alkyl and heteroaryl：
It is further preferred that compound of the compound based on carbazole derivates of the present invention for following structural 1-30：
The compound based on carbazole derivates of the present invention can be by Suzuki coupling reactions and Buchwald-
Hartwig reactions are prepared.
The compound based on carbazole derivates of the present invention can be applied in organic electroluminescence device, organic solar electricity
Pond, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer
Comprising a layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer or
More than one layer, wherein at least one layer chemical combination based on carbazole derivates contained as described in structural formula (I) in the organic layer
Thing：
Wherein X1、X2、Ar1、Ar2And L is defined as described above.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer；
The layer that the compound based on carbazole derivates wherein as described in structure formula (I) is located is luminescent layer；
The compound based on carbazole derivates wherein described in structure formula (I) is the compound of structural formula 1-30；
When the compound based on carbazole derivates as described in structure Formulas I is prepared for luminescent device, can be used alone,
Can also be used in mixed way with other compounds；Can be used alone based on the compound of carbazole derivates as described in structure Formulas I
A kind of compound therein, it is also possible to while using two or more the compound in structure Formulas I.
The organic electroluminescence device of the present invention, further preferred mode is that the organic electroluminescence device includes sun
Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer
The compound of one or more structure formula (I)；It is further preferred that the knot containing one or more in luminescent layer
The compound of structure formula 1-30.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound with structure formula (I) is made
For material of main part, used as material of main part, its concentration is the 20-99.9% of entirely luminous layer weight to wherein structure formula (I) compound,
It is preferred that 80-99%, more preferably 90-99%.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
The organic electroluminescence device of the present invention is when using compound of the present invention with structure Formulas I, it is possible to use take
With other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, and
Obtain blue and green light, gold-tinted, ruddiness or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested has good hole
Transmission performance, effectively can be transferred to hole on luminescent layer from anode.Can include that other small molecules and macromolecule are organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano group six, the fluoro- 7,7' of 2,3,5,6- tetra-, 8,
The cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'- tetra-, PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.Except the present invention with Compounds of structural formula I as phosphorescent light body material in addition to, can also arrange in pairs or groups other phosphorescence
Material of main part, phosphorescence light emitting guest material can include at least one metal in ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium
Metal-organic complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires there is good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but
This is not limited to, oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, effectively can be injected into organic layer electronics from negative electrode
In, it is mainly selected from alkali metal or alkali-metal compound, or selected from the compound or alkali of alkaline-earth metal either alkaline-earth metal
Metal complex, can select following compound, but not limited to this, it is alkali metal, alkaline-earth metal, rare earth metal, alkali-metal
Oxide either halide, the oxide of rare earth metal or halide, the alkali metal of oxide either halide, alkaline-earth metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, it is also possible to use cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.For metal motor can make
It is prepared with vapour deposition method or sputtering method.
Device experimental shows, compound based on carbazole derivates of the present invention as described in structure formula (I), with preferable heat
Stability, high-luminous-efficiency, high luminance purity.The organic electroluminescence made using the compound based on carbazole derivates
Part has the advantages that electroluminescent efficiency is good and excitation is excellent and life-span length.
Description of the drawings
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 18.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 19.
Fig. 3 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky
Cave transport layer, 150 are represented as luminescent layer, and 160 are represented as electron transfer layer, and 170 are represented as electron injecting layer, and 180 are represented as the moon
Pole.
Specific embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
The synthesis of the compound 18 of embodiment 1
The synthesis of intermediate 18-1
3-bromobenzaldehyde (5.5g), phenanthrenequione (6g), aniline (4.5g), ammonium acetate (8g) and acetic acid are added in there-necked flask
(100ml), it is heated to reflux 12 hours under nitrogen protection, cools down, add water, extracted with dichloromethane, anhydrous sodium sulfate drying is dense
Contracting, crude product ethanol and recrystallize with dichloromethane, obtain product 8.5g, yield 65%.1H NMR(400MHz,CDCl3):δ
8.46-8.86 (d, J=7.6Hz, 1H), 8.76-8.78 (d, J=8.4Hz, 1H), 8.70-8.72 (d, J=8.4Hz, 1H),
7.83(s,1H),7.10-7.77(m,13H).
The synthesis of intermediate 18-2
Compound 18-1 (4.49g, 10mmol), connection boric acid frequency is added to receive alcohol ester (3.0g, 12mmol) in single-necked flask,
Potassium acetate (3.0g), the triphenylphosphine palladium of dichloro two (50mg), dioxane (60mL) is heated to 100 DEG C of reaction 12h, while hot mistake
Silica gel, filter cake is washed with dichloromethane, revolves solvent evaporated, and crude product column chromatography is purified, and obtains product 3.2g, yield
64.5%.1H NMR(400MHz,CDCl3):δ 8.88-8.90 (d, J=7.6Hz, 1H), 8.77-8.79 (d, J=8.4Hz,
1H), 8.71-8.72 (d, J=8.4Hz, 1H), 8.14 (s, 1H), 7.21-7.76 (m, 13H), 1.33 (s, 12H).
The synthesis of intermediate 18-3
Bromo- 9, the 9- dimethyl fluorenes (140g, 0.5mol) of 2-, o-chloraniline (95g, 0.75mol), uncle are added toward reaction bulb
Butanol potassium (90g, 0.8mol), palladium (3.3g, 15mmol), tri-butyl phosphine tetrafluoroborate (8.7g, 30mmol) and first
Benzene (1.5L), is heated to reflux 24 hours under nitrogen protection, cools down, and washing is dried, and removes toluene, and crude product is crossed post purifying and obtained
90g products, yield 57%.
The synthesis of intermediate 18-4
In flask, intermediate 18-3 (40g, 0,125mol), sodium carbonate (40g, 0.38mol), palladium are added
(0.5g, 2.2mmol), tricyclohexyl phosphine tetrafluoroborate (1.6g, 4.4mmol) and dimethyl acetamide (0.5L), heat back
Stream 5 hours, cooling, subtracts and partial solvent is evaporated off, and cools down, and is added to the water, and is extracted with ethyl acetate, and is dried, and crosses post purifying and obtains
15g products, yield 43%.1H NMR(400MHz,CDCl3):δ8.38(s,1H),8.05-8.14(m,2H),7.82-7.84(d,
J=7.6Hz, 1H), 7.23-7.45 (m, 7H), 1.55 (s, 6H).
The synthesis of intermediate 18-5
Intermediate 18-4 (10g, 35.3mmol) is added toward reaction bulb, to bromo-iodobenzene (12g, 42mmol), potassium tert-butoxide
(7.9g, 70.6mmol), palladium (0.3g, 1.3mmol), tri-butyl phosphine tetrafluoroborate (0.8g, 2.7mmol) and toluene
(150mL), it is heated to reflux 24 hours under nitrogen protection, cools down, remove toluene, adds dichloromethane, washing to be dried, crude product
Post is crossed, 10g products, yield 57% is obtained.
The synthesis of compound 18
In single-necked flask, intermediate 18-5 (0.6g, 1.4mmol), intermediate 18-2 (0.7g, 1.4mmol), carbon are added
Sour potassium (1.38g, 10mmol), tetra-triphenylphosphine palladium (10mg), tetrahydrofuran (9mL), water (4mL) is heated to 80 DEG C of reaction 8h,
Cooling, is extracted with dichloromethane, with anhydrous sodium sulfate drying, is concentrated to give crude product, is obtained 0.31g in Jing column chromatography for separation and is produced
Product, yield 30%.1H NMR(400MHz,CDCl3):δ 8.91-8.93 (d, J=8.0Hz, 1H), 8.79-8.81 (d, J=
8.4Hz, 1H), 8.72-8.74 (d, J=8.4Hz, 1H), 8.46 (s, 1H), 8.20-8.22 (d, J=7.6Hz, 1H), 7.97
(s, 1H), 7.86-7.88 (d, J=7.2Hz, 1H), 7.23-7.79 (m, 24H), 1.54 (s, 6H). the proton magnetic of compound 18
Spectrogram is shown in Fig. 1.
The synthesis of the compound 19 of embodiment 2
The synthesis of intermediate 19-1
Intermediate 18-4 (10g, 35.3mmol), a bromo-iodobenzene (12g, 42mmol), potassium tert-butoxide are added toward reaction bulb
(7.9g, 70.6mmol), palladium (0.3g, 1.3mmol), tri-butyl phosphine tetrafluoroborate (0.8g, 2.7mmol) and toluene
(150mL), it is heated to reflux 24 hours under nitrogen protection, cools down, remove toluene, adds dichloromethane, washing to be dried, crude product
Post is crossed, 11g products, yield 71% is obtained.1H NMR(400MHz,CDCl3):δ 8.43 (s, 1H), 8.18-8.20 (d, J=
7.6Hz, 1H), 7.85-7.87 (d, J=7.6Hz, 1H), 7.83-7.88 (m, 1H), 7.64-7.66 (m, 1H), 7.28-7.59
(m,9H),1.52(s,6H).
The synthesis of compound 19
Intermediate 19-1 (2.1g, 4.8mmol), intermediate 18-2 (2.4g, 4.8mmol), carbon are added in single-necked flask
Sour potassium (3g), tetra-triphenylphosphine palladium (30mg), tetrahydrofuran (20mL), water (11mL) is heated to 80 DEG C of reaction 24h, and cooling is used
Dichloromethane is extracted, and with anhydrous sodium sulfate drying, is concentrated to give crude product, and in Jing column chromatography for separation product 1.64g, yield are obtained
47%.1H NMR(400MHz,CDCl3):δ 8.86-8.88 (d, J=7.6Hz, 1H), 8.74-8.76 (d, J=8.0Hz, 1H),
8.69-8.71 (d, J=8.4Hz, 1H), 8.51 (s, 1H), 8.26-8.28 (d, J=8.4Hz, 1H), 7.89-7.90 (d, J=
7.2Hz, 1H), 7.81-7.83 (d, J=7.6Hz, 1H), 7.01-7.76 (m, 24H). the hydrogen nuclear magnetic spectrogram of compound 19 is shown in figure
2。
Embodiment 3
The preparation of organic electroluminescence device
OLED is prepared using the compound 19 of embodiment 2
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the limited public affairs of South China glass group share
Department) Jing successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is hole injection layer 130 that the thick HAT-CN of 5nm are deposited with ITO
Then, TAPC is deposited with, forms the thick hole transmission layers 140 of 65nm.
Then, steam on hole transmission layer and cross the thick luminescent layers 150 of 10nm, wherein, compound 19 is the luminous material of main body
Material, and using Ir (ppy) 2acac of 7% weight ratio as phosphorescence doping guest materials.
Then, the thick TmPyPB of 50nm are deposited with luminescent layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) is measured in 100mA/ with Photo Research PR650 spectrometers
cm2Driving current under power efficiency be 21lm/W, be green spectral.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the limited public affairs of South China glass group share
Department) Jing successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is hole injection layer 130 that the thick HAT-CN of 5nm are deposited with ITO
Then, TAPC is deposited with, forms the thick hole transmission layers 140 of 65nm.
Then, steam on hole transmission layer and cross 10nm thickness luminescent layers 150, wherein, compound CBP is main body luminescent material,
And with the Ir (ppy) of 7% weight ratio2Acac is used as phosphorescence doping guest materials.
Then, the thick TmPyPB of 50nm are deposited with luminescent layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) is measured in 100mA/ with Photo Research PR650 spectrometers
cm2Driving current under power efficiency be 16lm/W, be green spectral.
Under identical drive-current condition, using the present invention carbazole derivates phosphorescent light body material prepare it is organic
The power efficiency of electroluminescent device is higher than comparative example, as described above, the compound of the present invention has high stability, preparation
Organic electroluminescence device has high efficiency and optical purity.
The structural formula of compound described in device is as follows：
。
Claims (8)
1. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer includes hole injection layer, hole
It is one or more layers in transport layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterised in that organic
At least one of which includes the compound based on carbazole derivates of following structure formula (I) in layer：
Wherein L is selected from xenyl or by the alkyl-substituted xenyls of C1-C4；
Wherein X1And X2Independently it is expressed as CH or N；
Wherein Ar1Selected from by the substituted or unsubstituted following aryl of C1-C4 alkyl：
Wherein Ar2Selected from following structural：
Wherein A, B, C, D, E and F are independently selected from O, S, NAr3Or CAr4Ar5；
Wherein, Ar3Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, replaced or not by C1-C4 alkyl
The following aryl for replacing：
Ar4And Ar5Separately it is selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl.
2. organic electroluminescence device according to claim 1, it is characterised in that wherein
L is selected from xenyl.
3. organic electroluminescence device according to claim 1, the wherein chemical combination based on carbazole derivates of structure formula (I)
Thing is the compound of following structural：
4. organic electroluminescence device according to claim 1, it is characterised in that as described in structure formula (I) based on carbazole
The layer that the compound of derivative is located is luminescent layer.
5. organic electroluminescence device according to claim 1, it is characterised in that as described in structure formula (I) based on carbazole
The compound of derivative is used alone, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 1, it is characterised in that as described in structure formula (I) based on carbazole
The compound of derivative is used alone a kind of compound therein, or while using two or more in structure formula (I)
Compound.
7. organic electroluminescence device according to claim 1, it includes anode, hole transmission layer, luminescent layer, electronics and passes
Defeated layer, electron injecting layer and negative electrode, it is characterised in that the chemical combination based on carbazole derivates containing structure formula (I) in luminescent layer
Thing.
8. organic electroluminescence device according to claim 7, it is characterised in that the compound in luminescent layer is structural formula
5th, 6,8,13,14,16,18,19,26,28,30 compound.
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| CN108623480A (en) * | 2017-03-17 | 2018-10-09 | 吉林奥来德光电材料股份有限公司 | New organic luminescent compounds and use its organic electroluminescence device |
| CN107840841A (en) * | 2017-11-02 | 2018-03-27 | 上海道亦化工科技有限公司 | A kind of carbazole pyridine derivate and application thereof and organic electroluminescence device |
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| CN102190627A (en) * | 2010-12-10 | 2011-09-21 | 吉林大学 | 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials |
| CN103772361A (en) * | 2012-10-24 | 2014-05-07 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device |
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| CN103772361A (en) * | 2012-10-24 | 2014-05-07 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device |
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