CN105601612B - Phosphorescence host compound containing indolyl radical and its organic electroluminescence device - Google Patents
Phosphorescence host compound containing indolyl radical and its organic electroluminescence device Download PDFInfo
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Abstract
The phosphorescence host compound containing indolyl radical that the present invention provides a kind of, the compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer includes one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of phosphorescence host chemical combination containing indolyl radical
Object and its organic electroluminescence device belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
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 generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially 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, especially 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, it will produce Joule heat so that organic material is easy to happen crystallization, affects 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 promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly 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
Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device
Rate.
Invention content
The phosphorescence host compound containing indolyl radical that present invention firstly provides a kind of, is to have the following structure Formulas I
Compound：
Wherein, L is empty or phenyl ring；
Z1-Z3Wherein at least one is N, remaining is CH；
Ar1And Ar2Separately it is selected from the aromatic rings of C6-C30.
Preferably, Ar1And Ar2Separately it is selected from phenyl, xenyl, naphthalene, anthryl, phenanthryl, pyrenyl, base, fluoranthene
Base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces either unsubstituted aryl) fluorenyl, 9,9- is Spirofluorene-based, replaces or does not take
Dibenzothiophene, substitution or the unsubstituted dibenzofuran group in generation；Aromatic ring wherein above-mentioned can be further by C1-C4's
Alkyl is replaced.
It is further preferred that the phosphorescence host compound containing indolyl radical is the chemical combination of following structural 1-38
Object：
The phosphorescence host compound containing indolyl radical of the present invention can be applied in organic electroluminescence device, You Jitai
Positive energy battery, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Including one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer or more, wherein at least one layer phosphorescence host containing indolyl radical contained as described in structural formula I in the organic layer
Close object：
Wherein L, Ar1、Ar2And Z1-Z3It 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 injecting 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.
Preferably, layer where the phosphorescence host compound containing indolyl radical as described in structural formula I is luminescent layer.
Preferably, the phosphorescence host compound containing indolyl radical as described in structural formula I is the chemical combination of structural formula 1-38
Object.
When the phosphorescence host compound containing indolyl radical as described in structural formula I is prepared for luminescent device, Ke Yidan
It solely uses, can also be used in mixed way with other compounds；The phosphorescence host compound containing indolyl radical as described in structural formula I
One such compound is can be used alone, two or more the compound in structural formula I can also be used simultaneously.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun
Pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode wherein contain in luminescent layer
The compound of one or more kinds of structural formula I；It is further preferred that containing one or more kinds of structures in luminescent layer
The compound of formula 1-38.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound conduct with structural formula I
Material of main part, wherein Compounds of structural formula I are as material of main part, and content is the 20-99.9% of entire luminous layer weight, preferably
80-99%, more preferably 90-99%.
The overall 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.May 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, six cyano, 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 be adjusted according to the needs
The range of visible light.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 include 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
In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious 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
Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, 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 the compound selected from alkaline-earth metal or alkaline-earth metal or alkali
Metal complex can select following compound, and 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, magnesia, these compounds can individually make
With 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.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows aromatic amine compounds of the present invention as described in structural formula I, has preferable thermal stability, height
Luminous efficiency, high luminance purity.It is imitated with electroluminescent using the organic electroluminescence device that the aromatic amine compounds make
The advantages of rate is good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present invention；
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transports
Layer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electron injecting layer,
190 are represented as cathode.
Specific implementation mode
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthesis of compound 2
The synthesis of intermediate 2-1
In the single-necked flask of 500mL, 5- bromo indoles (20.00g, 0.1mol), connection boric acid pinacol ester are sequentially added
(51.80g, 0.2mmol), potassium acetate (22.80g, 0.2mol), [bis- (diphenylphosphino) ferrocene of 1,1'-] palladium chloride
(1.50g), 350mL dioxane, flow back 8h under nitrogen protection.Revolving removes dioxane after cooling, with 200mL distilled water
It is extracted 3 times with dichloromethane after washing.It is recrystallized to give product 21.8g with methanol dichloromethane, yield is 90%.
The synthesis of intermediate 2-2
In the single-necked flask of 50mL, intermediate 2-1 (2.4g, 10mmol), 9- phenyl -9- (4- bromophenyls) are sequentially added
Fluorenes (4.4g, 11mmol), potassium carbonate (2.7g, 20mmol), four triphenyl phosphorus palladiums (50mg), dioxane (20.0mL) and water
(4.0mL), flow back 5h under nitrogen protection.Revolving removes dioxane after cooling, and dichloromethane is used after distilling water washing with 20mL
Alkane extracts 3 times.Crude product purifies to obtain product 3.5g through column chromatography, and yield is 80%.
The synthesis of compound 2
In three-necked flask, intermediate 2-2 (2g, 4.6mmol), dimethylformamide (30ml) is added, hydrogen is then added
Change sodium (264mg, 6.9mmol), reacts 1 hour, add chloro- 4, the 6- diphenylpyrimidins (1.5g, 5.5mmol) of 2-.Room temperature is anti-
It should stay overnight, be added to the water, filter, filter cake tetrahydrofuran and ethyl alcohol recrystallization obtain product 2.5g, yield 82%.
Embodiment 2
The synthesis of compound 3
Synthetic method is as with compound 2, in addition to replacing chloro- 4, the 6- hexichol of 2- with chloro- 4, the 6- diphenyl-s-triazine of 2-
Outside yl pyrimidines, yield 85%.
Embodiment 3
The synthesis of compound 18
In three-necked flask, intermediate 2-2 (2g, 4.6mmol), 2- (3- bromophenyls) -4,6- diphenyl -1,3,5- is added
Triazine (1.8g, 4.6mmol), potassium carbonate (1.2g, 9.2mmol), cuprous iodide (0.3g), Phen (0.3g) and nitrobenzene
(30ml) is heated to reflux 12 hours, cooling, solvent is removed under reduced pressure, crude product purifies to obtain yield 2.3g, yield through column chromatography
68%.
Embodiment 4
The synthesis of compound 22
The synthesis of intermediate 22-1
Synthetic method is as with intermediate 2-2, in addition to being yield 86% outside raw material with bromo- 9, the 9- diphenylfluorenes of 2-.
The synthesis of compound 22
Synthetic method is as with compound 3, other than replacing intermediate 2-2 with intermediate 22-1, yield 75%.
Embodiment 5
The synthesis of compound 27
Synthetic method is as the synthesis of compound 18, in addition to replacing intermediate 2-2 with intermediate 22-1 and with 4- (4-
Bromophenyl) -2,6- hexichol yl pyridines replace 2- (3- bromophenyls) -4,6- diphenyl -1,3,5-triazines outside, yield 70%.
Embodiment 6
The synthesis of compound 33
The synthesis of intermediate 33-1
Synthetic method is as intermediate 2-2, outside with bromo- 9, the 9- diphenylfluorenes of 4- as raw material, yield 90%.
The synthesis of compound 33
Synthetic method is as the synthesis of compound 3, other than being raw material with intermediate 33-1, yield 80%.
Embodiment 7
The synthesis of compound 34
Synthetic method is as the synthesis of compound 3, in addition to replacing 2-4 with chloro- 4,6-, bis- (4- the biphenyl)-s-triazine of 2-,
Outside 6- diphenyl-s-triazine, yield 76%.
Embodiment 8-14
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) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 50nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the NPB that 25nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 8nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer.Wherein, it shines based on the compounds of this invention
Material, and with the Ir of 9.8% weight ratio (ppy)2Acac adulterates guest materials as phosphorescence.
Then, the TPBi of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
200mA/cm2Brightness under efficiency be such as table 1.
Comparative example
Device prepared by comparative example is as the preparation method of embodiment 8-14, in addition to replacing the compounds of this invention with CBP
Outside as material of main part.
As can be seen from the above table, it under identical current density condition, is prepared using the compound of the present invention organic
The efficiency of electroluminescent device is all higher than comparative example, as described above, there is the compound of the present invention high stability, preparation to have
Organic electroluminescence devices have high efficiency and optical purity.
The structural formula of compound described in device is as follows：
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without
It needs creative work according to the present invention can conceive and makes 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 (9)
1. a kind of phosphorescence host compound containing indolyl radical, it is characterised in that it is the compound for having the following structure Formulas I：
Wherein, L is empty or phenyl ring；
Z1-Z3Wherein at least one is N, remaining is CH；
Ar1And Ar2Separately it is selected from by the substituted or unsubstituted phenyl of the alkyl of C1-C4, xenyl, naphthalene.
2. the phosphorescence host compound according to claim 1 containing indolyl radical, it is characterised in that it is having structure
The compound of formula 1-38：
3. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection
It is one or more layers in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that have
At least one layer includes the phosphorescence host compound containing indolyl radical as described in claim 1 in machine layer.
4. organic electroluminescence device according to claim 3, it is characterised in that contain indyl as described in structural formula I
Layer where the phosphorescence host compound of group is luminescent layer.
5. organic electroluminescence device according to claim 3, it is characterised in that contain indyl as described in structural formula I
The phosphorescence host compound of group is the compound of structural formula 1-38 as described in claim 2.
6. organic electroluminescence device according to claim 3, it is characterised in that contain indyl as described in structural formula I
The phosphorescence host compound of group is used alone, or is used in mixed way with other compounds.
7. organic electroluminescence device according to claim 3, it is characterised in that contain indyl as described in structural formula I
One such compound is used alone in the phosphorescence host compound of group, or use simultaneously two kinds or two kinds in structural formula I with
On compound.
8. organic electroluminescence device according to claim 3, it is characterised in that it includes anode, hole injection layer, skies
Cave transport layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, it is characterised in that containing a kind of or a kind of in luminescent layer
The compound of the above structural formula I.
9. a kind of organic electroluminescence device, it includes anode, hole injection layer, hole transmission layer, luminescent layer, electron-transports
Layer, electron injecting layer and cathode, it is characterised in that the compound contained in luminescent layer is structural formula as described in claim 2
The compound of 1-38.
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|---|---|---|---|---|
| KR101924086B1 (en) | 2016-02-26 | 2018-11-30 | 삼성에스디아이 주식회사 | Organic compound, organic optoelectric device and display device |
| KR102054276B1 (en) | 2016-06-29 | 2019-12-10 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102027961B1 (en) | 2016-06-29 | 2019-10-02 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR102054277B1 (en) | 2016-07-29 | 2019-12-10 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic device and organic optoelectronic device and display device |
| US11158817B2 (en) * | 2017-01-05 | 2021-10-26 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| US20210066613A1 (en) * | 2018-03-28 | 2021-03-04 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| WO2021125813A1 (en) * | 2019-12-20 | 2021-06-24 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
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| KR20150106668A (en) * | 2014-03-12 | 2015-09-22 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20150110101A (en) * | 2014-03-24 | 2015-10-02 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20150111441A (en) * | 2014-03-24 | 2015-10-06 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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| KR20150106668A (en) * | 2014-03-12 | 2015-09-22 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20150110101A (en) * | 2014-03-24 | 2015-10-02 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20150111441A (en) * | 2014-03-24 | 2015-10-06 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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