CN108047244A - A kind of snail compound and application thereof and organic electroluminescence device - Google Patents
A kind of snail compound and application thereof and organic electroluminescence device Download PDFInfo
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Abstract
The present invention provides a kind of snail compound, with following structural formula：The snail compound has preferable thermal stability, high-luminous-efficiency, high luminance purity and low driving voltage, can be applied to organic electroluminescence device, organic solar batteries, perovskite battery, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, 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 snail compound have the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of snail compound and application thereof further relates 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.Through hole transmission layer the electronics generated by cathode is followed to be incorporated in through electron transfer layer by the hole that anode generates
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 new display technology
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 be applied on flat-panel monitor and a new generation's illumination, 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, 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 generated so that organic material easily crystallizes, and affects service life and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material can be effectively reduced positive electricity
Lotus is transferred to the ability of luminescent layer from anode, improves efficiency and the thermostabilization of device.Traditional hole-injecting material, such as Copper
Phthalocyanine (CuPc), degradation is slow, prepares energy consumption height, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.Hole mobile material original NPB etc., thermal stability is poor, also largely influences device lifetime.Thus, it needs
Develop the electroluminescent organic material of efficient stable.
The content of the invention
The present invention provides a kind of snail compounds, are the compound with following structural formula I：
Wherein, Ar1With Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
A is selected from as O, S or Se.
Optionally, Ar1With Ar2Independently selected from phenyl, naphthalene, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl,
Base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted aryl) fluorenyl, C6-C30 N- aryl,
Alkyl-substituted carbazyl, indyl, carbazole indyl, the fluorenes carbazyl 9,9- of C1-C4 be Spirofluorene-based, C18-C60 three fragrance
Amido, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted dibenzofuran group, more than aryl can be with
Further substitute for the alkyl of C1-C12.
Further alternative, snail compound is the compound of following structural 1-50：
The snail compound of the present invention can be reacted by Buchwald-Hartwig, ullmann reaction and suzkui reaction
It is prepared.
The snail compound of the present invention can be applied to organic electroluminescence device, organic solar batteries, perovskite electricity
Pond, 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
Comprising one or more layers in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, wherein
Contain the snail compound as described in structural formula I at least one layer in the organic layer.
Wherein organic layer is hole transmission layer and luminescent 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, luminescent layer, electron transfer layer, electron injecting layer and exciton
Barrier layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and exciton barrier-layer；
Optionally, the layer where the snail compound as described in structural formula I is hole transmission layer；
Optionally, the compound containing one or more kinds of structural formula 1-50 in hole transmission layer.
When snail compound as described in structural formula I is prepared for luminescent device, can be used alone, can also with it is other
Compound is used in mixed way；Snail compound as described in structural formula I can be used alone a kind of compound therein, can also be same
When use two or more the compound in structural formula I.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When the present invention is used to have the compound of structural formula I, 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 exciton barrier-layer
It is medium, 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.There is compound described in structural formula I except above-mentioned
Outside, other small molecules and macromolecular organic compound can also be included, include but not limited to carbazole compound, triaromatic amine
Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano, six miscellaneous triphen
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'-
TCNQ), 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.In addition to the compound of fluorene class that can contain the present invention, following compound can also be contained, including still unlimited
In naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, phenol piperazine class compound, anthracene class
Close object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine chemical combination
Object, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent
Complex compound (such as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic polymer luminescent material, it
Can be used alone, can also a variety of mixtures use.
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
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 compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex can select following compound, but without being limited thereto：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.It can make for metal motor
It is prepared with vapour deposition method or sputtering method.
Device experimental shows snail compound of the present invention as described in structural formula I, and there is preferable thermal stability, height to shine
Efficiency, high luminance purity, low driving voltage.The organic electroluminescence device made of the snail compound has electroluminescent
Efficiency is good and excitation purity is excellent and the advantages of long lifespan.
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 hair
Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts example below, but without being limited thereto.
Embodiment 1
The synthetic route of compound 8
The synthetic method of intermediate 8-1
In 250mL round-bottomed flasks, input A (50g, 150mmol) and B (28g, 130mmol), Anhydrous potassium carbonate (41g,
30mmol), 150mL water and 300mL tetrahydrofurans, tetra-triphenylphosphine palladium (1g) are added in, nitrogen is protected, and heating stirring reflux 6 is small
When, the reaction was complete, cooling, and dichloromethane extraction after dry, is spin-dried for, crude product purifies to obtain 19g through column chromatography, and yield is
38%.
The synthetic method of intermediate 8-2
In 100mL round-bottomed flasks, intermediate 8-1 (19g, 49mmol), polyphosphoric acids (100g), at 180 DEG C are put into
When heating stirring 3 is small, reaction terminates, cooling, water quenching is added to go out until product is precipitated completely, suction filtration obtains product 15g, yield is
86%.
The synthetic method of intermediate 8-3
In 100mL round-bottomed flasks, intermediate 8-3 (5.5g, 16mmol), methanesulfonic acid (1.7g, 18mmol), phenol are added in
(3g, 32mmol), 150 DEG C heat simultaneously stir, after reaction, water quenching is added to go out, and with sodium hydrate aqueous solution adjust pH to 7~
8, by washing, after dichloromethane extraction, it is spin-dried for, crude by column chromatography purifies to obtain 5g, yield 63%.
The synthetic method of compound 8
In 100mL round-bottomed flasks, input intermediate 8-3 (1.8g, 3.6mmol), 4,4- dibiphenylyl amine (1g,
3.6mmol), potassium tert-butoxide (0.7g, 6.3mmol) adds in toluene (20mL), palladium (0.1g) and Xphos (0.2g), nitrogen
Protection, when lower heating stirring reflux 6 is small, the reaction was complete, cooling, by washing, after dichloromethane extraction, is spin-dried for, and passes through column
Chromatographic separation and purification product 1.2g, yield 59%.
Embodiment 2
The synthetic route of compound 10
The synthetic method of compound 10 is as the synthetic method of compound 8, except with N- (9,9- dimethyl -9H- fluorenes
Base -2- bases) -4- xenylamines replace 4,4 ' dibiphenylyl amine outside, yield 77%.
Embodiment 3
The synthetic route of compound 11
For synthetic method as the synthetic method of compound 8, raw materials used is N- [1,1 '-biphenyl] -2- base -9,9- diformazans
Base -9H- fluorenes -2- amine is replaced outside 4,4 ' dibiphenylyl amine, yield 62%.
Embodiment 4
The synthetic route of compound 15
The synthetic method of compound 15 is as the synthetic method of compound 1, except N- (4- dibenzofurans)-aniline replaces
Outside 4,4 ' dibiphenylyl amine, yield 73%.
Embodiment 5
The synthesis of compound 35
The synthesis of intermediate 35-1
Synthetic method is raw materials used for 4- dibenzothiophenes boric acid, yield 43% such as intermediate 8-1.
The synthesis of intermediate 35-2
Synthetic method is raw materials used for intermediate 35-1, yield 79% as intermediate 8-2.
The synthesis of intermediate 35-3
Synthetic method is raw materials used for intermediate 35-2, yield 75% such as intermediate 8-3.
The synthesis of compound 35
Synthetic method as the synthetic method of compound 1, it is raw materials used for intermediate 35-3 and N- [1,1 '-biphenyl]-
2- base -9,9- dimethyl -9H- fluorenes -2- amine, yield 56%.
Embodiment 6-10
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 are cleaned, then with oxygen plasma treatment 30 seconds.
Then, on ITO spin coating 45nm thickness PEDOT:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is
It is 30 minutes dry at 130,150 DEG C of hole injection layer；
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140,
Then, the luminescent layer 150 of 30nm thickness is deposited on electronic barrier layer, wherein, it shines based on the compounds of this invention
Material, and using weight ratio as 8% Ir (ppy)3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF are electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structure diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
100mA/cm2Current density under external quantum efficiency be such as table 1.
Comparative example 1-2
Device prepared by comparative example 1-2 is prepared with embodiment 6-10 as the preparation method of device, except with NPB, HT1 generation
For the compounds of this invention as hole mobile material outside.
Table 1
| Embodiment | Compound | Current efficiency (100%) | Luminescent color |
| 6 | 8 | 9.5 | Green light |
| 7 | 10 | 10 | Green light |
| 8 | 11 | 9.8 | Green light |
| 9 | 15 | 10.3 | Green light |
| 10 | 35 | 9.4 | Green light |
| Comparative example 1 | NPB | 6.1 | Green light |
| Comparative example 2 | HT1 | 6.0 | Green light |
The structural formula of compound described in device is as follows：
As it can be seen from table 1 the snail derivative of the present invention is luminous pure with preferable thermal stability, high-luminous-efficiency, height
Degree, low driving voltage, the organic electroluminescence device made of the snail compound has electroluminescent efficiency good and color
Purity is excellent and the advantages of long lifespan.
The preferred embodiment of the present invention described in detail above.It should be appreciated that those of ordinary skill in the art without
Creative work is needed according to the present invention can to 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 snail compound, which is characterized in that be the compound with following structural formula I：
Wherein, Ar1With Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
A is selected from as O, S or Se.
2. snail compound as described in claim 1, which is characterized in that Ar1With Ar2Independently selected from phenyl, naphthalene, biphenyl
Base, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted
Aryl) fluorenyl, the N- aryl of C6-C30, the alkyl-substituted carbazyl of C1-C4, indyl, carbazole indyl, fluorenes carbazyl
9,9- is Spirofluorene-based, the triaromatic amine base of C18-C60, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted
Dibenzofuran group, more than aryl can also further substitute for the alkyl of C1-C12.
3. snail compound as described in claim 1, which is characterized in that be the compound of following structural 1-50：
4. application of the snail compound described in claim 1 in organic electroluminescence device.
5. 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, exciton barrier-layer, electron transfer layer, which is characterized in that in the organic layer extremely
Few one layer contains snail compound as described in claim 1.
6. organic electroluminescence device as claimed in claim 5, which is characterized in that the snail compound as described in structural formula I
The organic layer at place is hole transmission layer.
7. organic electroluminescence device as claimed in claim 5, which is characterized in that the snail compound as described in structural formula I
A kind of compound therein is used alone or simultaneously using two or more the compound in structural formula I.
8. organic electroluminescence device as claimed in claim 5, which is characterized in that contain such as right in the hole transmission layer
It is required that the compound of one or more kinds of structural formula 1-50 described in 4.
9. organic electroluminescence device as claimed in claim 5, which is characterized in that the overall thickness of the organic layer is 1-
1000nm。
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| CN201711319364.6A CN108047244A (en) | 2017-12-12 | 2017-12-12 | A kind of snail compound and application thereof and organic electroluminescence device |
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| CN201711319364.6A CN108047244A (en) | 2017-12-12 | 2017-12-12 | A kind of snail compound and application thereof and organic electroluminescence device |
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| CN201711319364.6A Pending CN108047244A (en) | 2017-12-12 | 2017-12-12 | A kind of snail compound and application thereof and organic electroluminescence device |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108346753A (en) * | 2018-02-07 | 2018-07-31 | 上海道亦化工科技有限公司 | A kind of indeno carbazole compound and application thereof and organic electroluminescence device |
| CN110845503A (en) * | 2019-11-25 | 2020-02-28 | 南京林业大学 | Preparation and application of arylamine substituted benzodiindole organic hole transport material |
| KR102100581B1 (en) * | 2019-01-30 | 2020-04-14 | 두산솔루스 주식회사 | Organic light-emitting compound and organic electroluminescent device using the same |
| WO2020105920A1 (en) * | 2018-11-19 | 2020-05-28 | 주식회사 엘지화학 | Novel compound and organic light emitting diode using same |
| CN111205262A (en) * | 2020-01-21 | 2020-05-29 | 吉林省元合电子材料有限公司 | Amine derivative containing spirofluorene group and application thereof in organic electroluminescent device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170141321A1 (en) * | 2015-11-12 | 2017-05-18 | Sfc Co., Ltd. | Organic light-emitting diode with high efficiency |
| CN106977479A (en) * | 2015-11-13 | 2017-07-25 | Sfc株式会社 | Novel amine compound and the organic illuminating element including this |
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- 2017-12-12 CN CN201711319364.6A patent/CN108047244A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170141321A1 (en) * | 2015-11-12 | 2017-05-18 | Sfc Co., Ltd. | Organic light-emitting diode with high efficiency |
| CN106977479A (en) * | 2015-11-13 | 2017-07-25 | Sfc株式会社 | Novel amine compound and the organic illuminating element including this |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108346753A (en) * | 2018-02-07 | 2018-07-31 | 上海道亦化工科技有限公司 | A kind of indeno carbazole compound and application thereof and organic electroluminescence device |
| WO2020105920A1 (en) * | 2018-11-19 | 2020-05-28 | 주식회사 엘지화학 | Novel compound and organic light emitting diode using same |
| KR102100581B1 (en) * | 2019-01-30 | 2020-04-14 | 두산솔루스 주식회사 | Organic light-emitting compound and organic electroluminescent device using the same |
| CN110845503A (en) * | 2019-11-25 | 2020-02-28 | 南京林业大学 | Preparation and application of arylamine substituted benzodiindole organic hole transport material |
| CN110845503B (en) * | 2019-11-25 | 2022-04-22 | 南京林业大学 | Preparation and application of arylamine substituted benzodiindole organic hole transport material |
| CN111205262A (en) * | 2020-01-21 | 2020-05-29 | 吉林省元合电子材料有限公司 | Amine derivative containing spirofluorene group and application thereof in organic electroluminescent device |
| CN111205262B (en) * | 2020-01-21 | 2023-04-25 | 吉林省元合电子材料有限公司 | Amine derivative containing spirofluorene group and application thereof in organic electroluminescent device |
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