CN105753849A - Compound containing quinoxaline and pyridine groups and organic electroluminescent device thereof - Google Patents
Compound containing quinoxaline and pyridine groups and organic electroluminescent device thereof Download PDFInfo
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Abstract
The invention provides an organic electroluminescent compound containing quinoxaline and pyridine groups. The compound has better heat stability, high luminous efficiency and high luminous purity, can be used for manufacturing an organic electroluminescent device, and is applied to the field of organic solar cells, organic thin film transistors or organic photoreceptors. The invention also provides the organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer includes more than one layer in a luminous layer, a hole injection layer, a hole transporting layer, a hole blocking layer, and electron injection layer and an electron transporting layer; at least one layer in the organic layer contains a compound as shown by a structural formula I which is as shown in the description.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of organic electroluminescent compounds containing quinoxaline and pyridine groups and organic electroluminescence device thereof, belong to organic electroluminescence device Display Technique field.
Background technology
Organic electroluminescence device (OLEDs) is deposit, by spin coating or vacuum evaporation, the device that one layer of organic material is prepared between two metal electrodes, and a classical three layers organic electroluminescence device comprises hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer through hole transmission layer and is formed exciton, then luminous.Organic electroluminescence device can regulate, as desired by the material changing luminescent layer, the light launching various needs.
Organic electroluminescence device is as a kind of novel Display Technique, have self-luminous, wide viewing angle, low energy consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, can make flexible and the particular advantages such as transparent display floater and environmental friendliness, can be applied in flat faced display 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 is industrially applied to some extent, and for example as the screen such as camera and mobile phone, but current OLED is low due to efficiency, the factors such as service life is short restrict its wider application, particularly large screen display.And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device.Additionally, due to OLED when applying voltage-operated, Joule heat can be produced so that organic material is susceptible to crystallization, have impact on the life-span of device and efficiency, therefore, it is also desirable to the electroluminescent organic material of exploitation stability and high efficiency.
In OLED material, owing to the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronics, it is easy to causing the electronics of luminescent layer and number of cavities uneven, the efficiency of such device is just relatively low.Three (oxine) aluminum (Alq3) since invention, it is extensively studied, but it is still very low as its electron mobility of electron transport material, and the intrinsic characteristic that self can degrade, with in the device of electron transfer layer, it may appear that the situation that voltage declines, simultaneously, due to relatively low electron mobility so that substantial amounts of hole enters into Alq3In layer, excessive hole is with the form emittance of non-luminescent, and when as electron transport material, due to the characteristic of its green light, is restricted in application.Therefore, development stability and there is the electron transport material of bigger electron mobility, widely using of organic electroluminescence device is had great value.
Summary of the invention
Present invention firstly provides a kind of organic electroluminescent compounds containing quinoxaline and pyridine groups, it is the compound being structured with Formulas I:
Wherein, Ar1And Ar2Separately selected from C1-C8 alkyl, C1-C8 alkoxyl, the replacing or unsubstituted aryl, the replacement of C3-C30 or unsubstituted containing one or more heteroatomic heteroaryl of C6-C30；
X is selected from O, S, Se；
L is selected from phenyl, pyridine radicals, pyrimidine radicals, naphthyl；
Py is pyridine radicals.
Preferably, Ar1And Ar2Separately selected from phenyl, xenyl, naphthyl, pyridine radicals, quinolyl, pyridinylphenyl, isoquinolyl, quinolyl phenyl；The above group can be replaced by the alkyl of C1-C10 or alkoxyl further.
Preferably, X is selected from O, S.
Preferably, L is selected from phenyl, pyridine radicals, naphthyl.
It is further preferred that the compound that organic electroluminescent compounds is following structural 1-44 containing quinoxaline and pyridine groups of the present invention:
The organic electroluminescent compounds containing quinoxaline and pyridine groups of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer comprises more than one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, has at least one layer containing, for example the organic electroluminescent compounds containing quinoxaline and pyridine groups described in structural formula I in wherein said organic layer:
Wherein Ar1、Ar2, X, L and Py defined as described above.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer.
Preferably, the organic electroluminescent compounds place layer containing quinoxaline and pyridine groups as described in structural formula I is electron transfer layer and/or electron injecting layer.
Preferably, the compound that organic electroluminescent compounds is structural formula 1-44 containing quinoxaline and pyridine groups as described in structural formula I.
When the organic electroluminescent compounds containing quinoxaline and pyridine groups as described in structural formula I is prepared for luminescent device, it is possible to be used alone, it is also possible to use with the mixing of other compound；The organic electroluminescent compounds containing quinoxaline and pyridine groups as described in structural formula I can be used alone a kind of compound therein, it is also possible to use the two or more compound in structural formula I simultaneously.
The organic electroluminescence device of the present invention, it is preferred that mode be, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein compound containing structural formula I in electron transfer layer and/or electron injecting layer；It is further preferred that compound containing structural formula 1-44 in electron transfer layer and/or electron injecting layer.
In the organic electroluminescence device of the present invention, electron injecting layer when Compounds of structural formula I is as electron transfer layer, can also be also served as.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, it is preferable that 50-500nm.
The organic electroluminescence device of the present invention is when the compound using the present invention to have structural formula I, can arrange in pairs or groups and use other material, as medium on hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, and obtain blue light, green glow, gold-tinted, HONGGUANG or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, it is possible to effectively hole is transferred to luminescent layer from anode.Other little molecule and macromolecular organic compound can be included, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the assorted triphen of six cyano group six (hexanitrilehexaazatriphenylene), 2,3,5,6-tetra-fluoro-7,7', 8,8'-tetra-cyanogen dimethyl-parabenzoquinone (F4-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, it is possible to regulate the scope of visible ray as required.Can containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, Benzo[b compounds, compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex, metal Phosphorescent complex is (such as Ir, Pt, Os, Cu, Au), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can be used alone, can also use by multiple mixture.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires have good electronic transmission performance, it is possible to effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Except the present invention there is Compounds of structural formula I except, can also select or arrange in pairs or groups following compound, but is not limited to this: oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, luxuriant and rich with fragrance quinoline compounds, metallo-chelate are (such as Alq3, oxine lithium), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, except the present invention there is Compounds of structural formula I except, it is mainly selected from alkali metal or alkali-metal compound, or it is selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but it is not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide or halogenide, the oxide of alkaline-earth metal or halogenide, the oxide of rare earth metal or halogenide, the organic complex of alkali metal or alkaline-earth metal；It is preferably lithium, lithium fluoride, lithium oxide, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcium fluoride, calcium oxide, magnesium, Afluon (Asta), magnesium carbonate, magnesium oxide, these compounds can be used alone can also mixture use, it is also possible to other electroluminescent organic materials with the use of.
Each layer of organic layer in the organic electroluminescence device of the present invention, it is possible to prepared by vacuum vapour deposition, molecular beam vapour deposition method, the modes such as the dip coating of solvent, spin-coating method, stick coating method or inkjet printing that are dissolved in.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the organic electroluminescent compounds containing quinoxaline and pyridine groups described in the present invention such as structural formula I, has better heat stability, high-luminous-efficiency, high luminance purity.Electroluminescent efficiency is good and excitation is excellent and the advantage of life-span length to adopt the organic electroluminescence device that this organic electroluminescent compounds makes to have.
Accompanying drawing explanation
Fig. 1 is a kind of organic electroluminescence device structural representation of the present invention；
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Detailed description of the invention
In order to describe the present invention in more detail, especially exemplified by example below, but it is not limited to this.
Embodiment 1
The synthesis of compound 2
The synthesis of intermediate 2-1
In flask, add 4,7-dibromo diazosulfides (18.6g, 0.1mol), benzil (21g, 0.1mol) with acetic acid (200ml), it is heated to 90 degree and reacts 5 hours, cooling, filter, filter cake ethyl alcohol recrystallization, obtains product 28g, productivity 78%.
In 100mL there-necked flask, add 4,7-dibromo diazosulfides (20g, 69mmol) and ethanol (500mL), under condition of ice bath, add sodium borohydride (11.4g, 300mmol), 20h is stirred at room temperature.Being spin-dried for solvent, add 100mL water, extraction into ethyl acetate three times, anhydrous sodium sulfate dries, and concentration obtains product 17.2g, productivity 95%.
The synthesis of intermediate 2-2
In flask, adding intermediate 2-1 (17g, 64.4mmol), benzil (13.5g, 64.4mmol) and acetic acid (400ml), stirring, heating, to 90 DEG C, stirs 3h.It is cooled to room temperature, has solid to precipitate out.Filter, crude product ethyl alcohol recrystallization, obtain pale yellow powder 21g, productivity 75%.
The synthesis of intermediate 2-3
In there-necked flask; add intermediate 2-2 (5g; 11.4mmol), 4-dibenzofurans boric acid (2.4g; 11.4mmol), potassium carbonate (4.1g, 30mmol), tetra-triphenylphosphine palladium (0.3g), oxolane (60ml) and water (20ml), heat 5 hours under nitrogen protection; cooling; filtering, thick product obtains product 4.3g, productivity 73% through column chromatography purification.
The synthesis of intermediate 2-4
In there-necked flask; add bromo-iodobenzene (28g; 0.1mol), 3-pyridine boronic acid (12.3g, 0.1mol), potassium carbonate (27.2g; 200mmol), tetra-triphenylphosphine palladium (0.8g), oxolane (200ml) and water (50ml); heat 5 hours under nitrogen protection, cooling, filter; thick product obtains product 13g, productivity 56% through column chromatography purification.
The synthesis of intermediate 2-5
In flask; add intermediate 2-4 (13g; 56mmol), connection boric acid pinacol ester (21.3g; 84mmol), potassium acetate (20g, 200mmol), dioxane (300ml) and two triphenylphosphine palladium (1g), be heated to reflux 5 hours under nitrogen protection; cooling; concentration, thick product obtains product 14.6g, productivity 93% through column chromatography purification.
The synthesis of compound 2
In there-necked flask; add intermediate 2-3 (2g, 3.8mmol), intermediate 2-5 (1.1g, 3.8mmol), potassium carbonate (1.1g; 10mmol), tetra-triphenylphosphine palladium (0.1g), oxolane (50ml) and water (20ml); heating 5 hours under nitrogen protection, cooling, with dichloromethane extraction; dry; filtering, thick product obtains product 1.9g, productivity 82% through column chromatography purification.
Embodiment 2
The synthesis of compound 9
The synthesis of intermediate 9-1
In there-necked flask; add the iodo-5-bromopyridine (10g of 2-; 35.5mmol), 3-pyridine boronic acid (4.4g; 35.5mmol), potassium carbonate (13.8g, 100mmol), tetra-triphenylphosphine palladium (0.8g), oxolane (100ml) and water (50ml), heat 5 hours under nitrogen protection; cooling; filtering, thick product obtains product 6.4g, productivity 77% through column chromatography purification.
The synthesis of intermediate 9-2
In flask; add intermediate 9-1 (6g; 25.6mmol), connection boric acid pinacol ester (7.8g; 31mmol), potassium acetate (6g, 60mmol), dioxane (100ml) and two triphenylphosphine palladium (0.5g), be heated to reflux 5 hours under nitrogen protection; cooling; concentration, thick product obtains product 6.1g, productivity 84% through column chromatography purification.
The synthesis of compound 9
In there-necked flask; add intermediate 2-3 (2g, 3.8mmol), intermediate 2-5 (1.1g, 3.8mmol), potassium carbonate (1.1g; 10mmol), tetra-triphenylphosphine palladium (0.1g), oxolane (50ml) and water (20ml); heating 5 hours under nitrogen protection, cooling, with dichloromethane extraction; dry; filtering, thick product obtains product 1.7g, productivity 75% through column chromatography purification.
Embodiment 3
The synthesis of compound 14
The synthesis of intermediate 14-1
Synthetic method is the same with intermediate 2-3, except replacing 4-dibenzofurans with 4-dibenzothiophenes boric acid, and productivity 65%.
The synthesis of intermediate 14
Synthetic method is the same with compound 2, except replacing intermediate 2-3 with intermediate 14-1, and productivity 80%.
Embodiment 4
The synthesis of compound 20
Synthetic method is with compound 9, except replacing intermediate 2-3 with intermediate 14-1, and productivity 82%.
Embodiment 5
The synthesis of compound 29
The synthesis of intermediate 29-1
Synthetic method is the same with intermediate 2-3, except with except 2-dibenzofurans boric acid, and productivity 58%.
The synthesis of compound 29
The synthetic method of compound 29 is the same with compound 9, except replacing intermediate 2-3 with intermediate 29-1, and productivity 79%.
Embodiment 6
The synthesis of compound 33
Intermediate 33-1
Synthetic method is the same with intermediate 2-3, except replacing 4-dibenzofurans with 2-dibenzothiophenes, and productivity 54%.
The synthesis of compound 33
Synthetic method is with compound, except replacing intermediate 2-3 with intermediate 33-1, and productivity 85%.
Embodiment 7-12
The preparation of organic electroluminescence device
The compound using the present invention prepares OLED.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then by oxygen plasma treatment 30 seconds.
Then, it is deposited with NPB, forms the thick hole transmission layer 130 of 60nm.
Then, hole transmission layer is deposited with the thick Alq of 37.5nm31%C-545T is as luminescent layer 140 in doping.
Then, luminescent layer is deposited with the compounds of this invention thick for 37.5nm as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) with PhotoResearchPR650 spectrogrph record at 200mA/cm2Electric current density under efficiency be as shown in table 1.
Comparative example
Except electron transfer layer Alq3Replace outside the compounds of this invention, other the same with embodiment 7.
Prepared device (structural representation is shown in Fig. 1) with PhotoResearchPR650 spectrogrph record at 20mA/cm2Electric current density under efficiency as shown in table 1.
Table 1
At identical conditions, the efficiency of organic electroluminescence device prepared by the organic electroluminescent compounds of the application present invention is all higher than comparative example, as it has been described above, the compound of the present invention has high stability, organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
The preferred embodiment of the present invention described in detail above.Should be appreciated that those of ordinary skill in the art just can make many modifications and variations according to the design of the present invention without creative work.Therefore, all technical staff in the art, all should in the protection domain being defined in the patent claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment.
Claims (10)
1. the organic electroluminescent compounds containing quinoxaline and pyridine groups, it is characterised in that it is the compound being structured with Formulas I:
Wherein, Ar1And Ar2Separately selected from C1-C8 alkyl, C1-C8 alkoxyl, the replacing or unsubstituted aryl, the replacement of C3-C30 or unsubstituted containing one or more heteroatomic heteroaryl of C6-C30；
X is selected from O, S, Se；
L is selected from phenyl, pyridine radicals, pyrimidine radicals, naphthyl；
Py is pyridine radicals.
2. the organic electroluminescent compounds containing quinoxaline and pyridine groups according to claim 1, it is characterised in that Ar1And Ar2Separately selected from phenyl, xenyl, naphthyl, pyridine radicals, quinolyl, pyridinylphenyl, isoquinolyl, quinolyl phenyl；Or above-mentioned group is replaced by the alkyl of C1-C10 or alkoxyl further.
3. the organic electroluminescent compounds containing quinoxaline and pyridine groups according to claim 1, it is characterised in that X is selected from O, S.
4. the organic electroluminescent compounds containing quinoxaline and pyridine groups according to claim 1, it is characterised in that L is selected from phenyl, pyridine radicals, naphthyl.
5. the organic electroluminescent compounds containing quinoxaline and pyridine groups according to claim 1, it is characterised in that it is the compound of following structural 1-44:
6. an organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer comprises more than one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that have at least one layer in described organic layer containing the organic electroluminescent compounds containing quinoxaline and pyridine groups as claimed in claim 1.
7. organic electroluminescence device according to claim 6, it is characterised in that the organic electroluminescent compounds place layer containing quinoxaline and pyridine groups as described in structural formula I is electron transfer layer and/or electron injecting layer.
8. organic electroluminescence device according to claim 6, it is characterised in that the compound that organic electroluminescent compounds is structural formula 1-44 containing quinoxaline and pyridine groups as described in structural formula I.
9. organic electroluminescence device according to claim 6, it is characterised in that the organic electroluminescent compounds containing quinoxaline and pyridine groups as described in structural formula I is used alone, or and other compound mixing use.
10. organic electroluminescence device according to claim 6, it is characterized in that it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that electron transfer layer and/or in electron injecting layer containing the compound of structural formula I.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106711351A (en) * | 2017-01-25 | 2017-05-24 | 上海道亦化工科技有限公司 | Compound containing quinoxaline and biphenyl groups and organic electroluminescence device thereof |
| WO2020022732A1 (en) * | 2018-07-25 | 2020-01-30 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| WO2020022769A1 (en) * | 2018-07-25 | 2020-01-30 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
| CN112400010A (en) * | 2018-07-25 | 2021-02-23 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN112424964A (en) * | 2018-07-25 | 2021-02-26 | 罗门哈斯电子材料韩国有限公司 | Multiple host materials and organic electroluminescent device comprising the same |
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| CN106711351A (en) * | 2017-01-25 | 2017-05-24 | 上海道亦化工科技有限公司 | Compound containing quinoxaline and biphenyl groups and organic electroluminescence device thereof |
| CN106711351B (en) * | 2017-01-25 | 2019-01-15 | 上海道亦化工科技有限公司 | Compound and its organic electroluminescence device containing quinoxaline and biphenyl group |
| WO2020022732A1 (en) * | 2018-07-25 | 2020-01-30 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| WO2020022769A1 (en) * | 2018-07-25 | 2020-01-30 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
| CN112400010A (en) * | 2018-07-25 | 2021-02-23 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN112424964A (en) * | 2018-07-25 | 2021-02-26 | 罗门哈斯电子材料韩国有限公司 | Multiple host materials and organic electroluminescent device comprising the same |
| JP2021532586A (en) * | 2018-07-25 | 2021-11-25 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Multiple host materials and organic electroluminescent devices containing them |
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