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CN107987009A - A kind of carbazole derivates and application thereof and organic electroluminescence device - Google Patents

A kind of carbazole derivates and application thereof and organic electroluminescence device Download PDF

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CN107987009A
CN107987009A CN201711217122.6A CN201711217122A CN107987009A CN 107987009 A CN107987009 A CN 107987009A CN 201711217122 A CN201711217122 A CN 201711217122A CN 107987009 A CN107987009 A CN 107987009A
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organic
electroluminescence device
carbazole derivates
organic electroluminescence
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The present invention provides a kind of carbazole derivates, it is with following structural formula：The carbazole derivates have preferable stability, it can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field, during for organic electroluminescence device, operating voltage can be reduced, device efficiency is improved, is the material of main part with excellent performance.Present invention also offers a kind of organic electroluminescence device, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer compound contained such as structural formula I in organic layer, the organic electroluminescence device made of carbazole derivates have higher luminous efficiency and optical purity.

Description

A kind of carbazole derivates and application thereof and organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of carbazole derivates and application thereof, further relate to A kind of organic electroluminescence device.
Background technology
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, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics produced by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer by the hole that anode produces Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly, can apply on flat-panel monitor and a new generation's illumination, can also conduct The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict 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.It is voltage-operated in application additionally, due to OLED device When, Joule heat can be produced so that organic material easily crystallizes, and have impact on service life and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation 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 also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, common to be used 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 transmitted 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 reduces the effect of device Rate.
The content of the invention
The present invention provides a kind of carbazole derivates, it is the compound with following structural formula I：
Wherein, Ar1And Ar2Independently selected from the aryl substitution or unsubstituted for substituting either unsubstituted C6-C30 The heteroaryl of C3-C30；
R1-R8Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30 Aryl.
Optionally, Ar1Selected from phenyl, tolyl, xenyl, naphthyl, fluorenyl and fluoranthene base.
Optionally, Ar2Selected from phenyl, cyano-phenyl, fluorine substituted-phenyl, xenyl, diphenyl, naphthyl, three and phenyl, anthracene Base, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted aryl) fluorenyl, 9, 9- is Spirofluorene-based, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted dibenzofuran group, pyridine radicals, phonetic Piperidinyl, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoline Quinoline base, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals, above aryl and heteroaryl can also be further Substitute for the alkyl of C1-C12.
Optionally, R1-R8Selected from hydrogen or phenyl.
Optionally, carbazole derivates are the compound of following structural formula 1-54：
The carbazole derivates of the present invention can be applied in organic electroluminescence device, also can be widely used to organic sun Can battery, Organic Thin Film Transistors or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer Layer；
Optionally, 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.
It is at least one layer of in the organic layer to contain foregoing carbazole derivates.
Optionally, the organic layer where two carbazole derivates of xenyl is luminescent layer.
Optionally, the compound in the luminescent layer is at least one of structural formula 1-54 compound or is institute State the compound of structural formula 1-54 and the mixture of other compounds.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance, can effectively be transferred to hole on luminescent layer from anode.It can include other small molecules and macromolecule is organic Compound, includes but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed The scope of visible ray.Except the present invention have 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 be included selected from least one of ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium metal Metal-organic complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Following compound can be selected, but It is not limited to this：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 and benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode In, it is mainly selected from the alkali metal either compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali 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 and magnesia, these compounds can be independent Using can also mixture use, can also be used 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.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows that carbazole derivates of the present invention as described in structural formula I have preferable heat endurance, and height shines Efficiency, high luminance purity.The organic electroluminescence device made of the compound has electroluminescent efficiency good and colour purity The advantages of spending excellent and long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structure diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be resistance Barrier, 160 be luminescent layer, and 170 be electron transfer layer, and 180 be electron injecting layer, and 190 be cathode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
The synthetic route of intermediate 2
The synthetic method of intermediate 2
(1) in flask, carbazole (15g, 89.8mmol), the bromo- 3- chloroiodobenzones (29g, 92mmol) of 4-, potassium hydroxide are added (10g, 180mmol), cuprous iodide (1g), phenanthroline (1.5g), ortho-xylene (250mL), is heated to reflux under nitrogen protection 10 it is small when, cooling adds dichloromethane and water, layering, and crude product purifies to obtain 18.5g, yield 58% through column chromatography.
(2) in flask, addition intermediate 1 (17g, 48mmol), 9 phenyl-carbazole -3- boric acid (13.8g, 48mmol), Potassium carbonate (13.6g, 100mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (200mL) and water (100mL), are protected in nitrogen Be heated to reflux under shield 12 it is small when, cooling, is extracted with dichloromethane, dry, and concentration, crude product purifies to obtain 20g through column chromatography, is produced Rate is 80%.
Embodiment 1
The synthesis of compound 3
In flask, intermediate 2 (1.5g, 2.9mmol), 9- phenanthrene boric acid (0.65g, 2.9mmol), potassium carbonate are added (0.82g, 6mmol), palladium (0.1g), x-phos (0.2g), dioxane (20mL) and water (10mL), under nitrogen protection Be heated to reflux 12 it is small when, cooling, is extracted with dichloromethane, dry, and concentration, crude product purifies to obtain 1.4g, yield through column chromatography For 73%.
The synthetic method of other embodiment such as compound 3, be all by the use of intermediate 2 as raw material, it is other except It is specific such as table 1 outside boric acid used：
Table 1
Embodiment 10-18
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the TAPC for 50nm thickness being deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein, the compounds of this invention shines for main body Material, and using weight ratio as 3% Ir (ppy)3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, evaporation 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structure diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure 5000cd/m2Brightness under current efficiency be such as table 2.
Comparative example 1
Device prepared by comparative example is as embodiment 10-18 device preparation methods, except replacing chemical combination of the present invention with PH1 Thing as material of main part outside.
Table 2
Embodiment Compound Current efficiency (cd/A) Glow color
10 3 48 Green light
11 8 49 Green light
12 11 47 Green light
13 17 53 Green light
14 20 51 Green light
15 24 52 Green light
16 32 53 Green light
17 46 56 Green light
18 52 55 Green light
Comparative example 1 PH1 42 Green light
The structural formula of compound described in device is as follows：
From Table 2, it can be seen that the carbazole derivates of the present invention are used for organic electroluminescence device, work electricity can be reduced Pressure, improves device efficiency, is the phosphorescent light body material with excellent performance, and have high stability, the organic electroluminescence of preparation Luminescent device has high efficiency and optical purity.
Preferred embodiment of the invention described in detail above.It should be appreciated that those of ordinary skill in the art without Need creative work to conceive according to the present invention and make many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be in the protection domain being defined in the patent claims.

Claims (10)

1. a kind of carbazole derivates, it is characterised in that it is the compound with following structural formula I：
Wherein, Ar1And Ar2Independently selected from the substitution either aryl of unsubstituted C6-C30 or substitution or unsubstituted C3- The heteroaryl of C30；
R1-R8Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8 and substitution or unsubstituted C6-C30 Aryl.
2. carbazole derivates as claimed in claim 1, it is characterised in that Ar1Selected from phenyl, tolyl, xenyl, naphthyl, fluorenes Base and fluoranthene base.
3. carbazole derivates as claimed in claim 1, it is characterised in that Ar2Selected from phenyl, cyano-phenyl, fluorine substituted-phenyl, Xenyl, diphenyl, naphthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- Two substitution either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted dibenzothiophene, substitution or Unsubstituted dibenzofuran group, pyridine radicals, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazoles Base, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals And above aryl and heteroaryl can also further substitute for the alkyl of C1-C12.
4. carbazole derivates as claimed in claim 1, it is characterised in that R1-R8Selected from hydrogen or phenyl.
5. carbazole derivates as claimed in claim 1, it is characterised in that be the compound of following structural formula 1-54：
6. application of the carbazole derivates described in claim 1 in organic electroluminescence device.
7. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, it is characterised in that institute State at least one layer in organic layer and contain carbazole derivates as claimed in claim 1.
8. organic electroluminescence device as claimed in claim 6, it is characterised in that the organic layer where the carbazole derivates For luminescent layer.
9. organic electroluminescence device as claimed in claim 7, it is characterised in that the compound in the luminescent layer is right It is required that at least one of 4 described structural formula 1-54 compounds or compound and other compounds for the structural formula 1-54 Mixture.
10. organic electroluminescence device as claimed in claim 6, it is characterised in that the gross thickness of the organic layer is 1- 1000nm。
CN201711217122.6A 2017-11-28 2017-11-28 A kind of carbazole derivates and application thereof and organic electroluminescence device Pending CN107987009A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
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CN108503636A (en) * 2018-06-06 2018-09-07 长春海谱润斯科技有限公司 A kind of electron transport material and its organic luminescent device
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US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
WO2020111585A1 (en) * 2018-11-27 2020-06-04 주식회사 엘지화학 Novel compound and organic light-emitting device using same
US11985893B2 (en) 2019-11-08 2024-05-14 Samsung Display Co., Ltd. Organic electroluminescence device and aromatic compound for organic electroluminescence device
CN111187254B (en) * 2020-01-10 2023-11-07 上海百豪新材料有限公司 Carbazole-based organic electrophosphorescent material composition and application thereof
CN111205269A (en) * 2020-01-10 2020-05-29 上海百豪新材料有限公司 Preparation method and application preparation of carbazole-based organic electrophosphorescent material composition
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CN111187254A (en) * 2020-01-10 2020-05-22 上海百豪新材料有限公司 Carbazole-based organic electrophosphorescent material composition and application thereof
CN111704605B (en) * 2020-06-28 2023-09-22 宁波卢米蓝新材料有限公司 Carbazole derivative and preparation method and application thereof
CN111704605A (en) * 2020-06-28 2020-09-25 宁波卢米蓝新材料有限公司 Carbazole derivative and preparation method and application thereof
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