CN108358895A - A kind of benzazolyl compounds and application thereof and organic electroluminescence device - Google Patents

A kind of benzazolyl compounds and application thereof and organic electroluminescence device Download PDF

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CN108358895A
CN108358895A CN201810124395.4A CN201810124395A CN108358895A CN 108358895 A CN108358895 A CN 108358895A CN 201810124395 A CN201810124395 A CN 201810124395A CN 108358895 A CN108358895 A CN 108358895A
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benzazolyl compounds
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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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Abstract

The present invention provides a kind of benzazolyl compounds, have the following structure formula：The benzazolyl compounds have preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, 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 benzazolyl compounds containing such as structural formula I in organic layer, the organic electroluminescence device made of benzazolyl compounds have the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.

Description

A kind of benzazolyl compounds 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 benzazolyl compounds and application thereof further relate to A kind of organic electroluminescence device.
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.And it is exactly in organic electroluminescence device to restrict one of key factor The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat will produce 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 organic electroluminescence of stability and high efficiency Luminescent material.
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.
In OLED material, the speed due to the speed of most electroluminescent organic material transporting holes than transmitting electronics Soon, the electrons and holes quantity for be easy to causeing luminescent layer is uneven, and the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines) Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines, Simultaneously as lower electron mobility so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, be above restricted in application.Cause This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility With great value.
Invention content
It is the compound for having the following structure Formulas I the present invention provides a kind of benzazolyl compounds：
Wherein, Ar is selected from the heteroaryl for replacing the either aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 Base, the substitution either triaromatic amine base of two aromatic aminos of unsubstituted C12-C30, substitution or unsubstituted C18-C30, substitution Either the carbazyl substitution of unsubstituted C12-C30 or the indyl of unsubstituted C8-C30；R1-R3Independently selected from C1- The aryl of the alkyl of C12, substitution or unsubstituted C6-C30.
Optionally, Ar be selected from phenyl, naphthalene, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9, 9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, the N- aryl of C6-C30, C1-C4 alkyl substitution Carbazyl, indyl, carbazole indyl, fluorenes carbazyl 9,9- be Spirofluorene-based, triaromatic amine base of C18-C60, substitution or not Substituted dibenzothiophene, substitution or unsubstituted dibenzofuran group, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, Imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzo furan It mutters base, azepine dibenzothiophene.
Further alternative, the aryl and the alkyl that heteroaryl is C1-C12 replace.
Optionally, R1-R3Independently selected from methyl, ethyl, propyl, isopropyl, tertiary butyl, normal-butyl, n-hexyl, phenyl.
Optionally, the benzazolyl compounds are the compound of following structural 1-58：
A kind of benzazolyl compounds of the present invention can pass through Buchwald-Hartwig reactions, ullmann reaction, Suzkui It is prepared.
The benzazolyl compounds of the present invention can be applied to organic electroluminescence device, organic solar batteries, organic film Transistor or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Including at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, at least one layer of benzazolyl compounds containing as described in structural formula I in the organic layer.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Further alternative, the layer where the benzazolyl compounds is luminescent layer and at least one in electron transfer layer Layer.
Benzazolyl compounds as described in structural formula I are used alone, or are used in mixed way with other compounds；Such as structural formula I institutes The benzazolyl compounds stated can be used alone one such compound, can also use two kinds or two in structural formula I simultaneously Kind or more compound；A kind of benzazolyl compounds selected from structural formula 1-58 are used alone, or are selected from simultaneously using two or more The benzazolyl compounds of structural formula 1-58.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer, Luminescent layer, electron transfer layer, electron injecting layer and cathode contain one or more kinds of structural formula I's wherein in luminescent layer Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-58 in luminescent layer.
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.In addition to the present invention is with Compounds of structural formula I, following compound can also be contained, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate 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.In addition to that can use with this hair Outside bright compound, it is also an option that following compound, but not limited to this：Oxa- oxazole, thiazole compound, triazole Compound, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic Compound, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzo miaow Azole compounds.
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 benzazolyl compounds of the present invention as described in structural formula I, and there is preferable thermal stability, height to shine Efficiency, high luminance purity.Using the benzazolyl compounds make organic electroluminescence device have electroluminescent efficiency well and The advantages of 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, and 140 are represented as sky Cave transport 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 electronics note Enter layer, 190 are represented as cathode；
Fig. 2 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 transmission layer, and 140 are represented as sending out Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 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.
The synthetic route of intermediate
The synthetic method of intermediate A
In flask, the bromo- hydrazinobenzene hydrochloride salts of 4- (22.2g, 0.1mol), 3- methyl-butanone (15g, 0.1mol), vinegar is added Sour (150mL), is heated to reflux 5 hours under nitrogen protection, cooling, and filtering, filter cake ethyl alcohol recrystallization obtains product 16g, produces Rate 53%.
The synthetic method of intermediate B
In flask, intermediate A (15g, 50mmol), connection pinacol borate (15g, 60mmol), potassium acetate is added (7.3g, 75mmol), Pd (dppf) Cl2(0.5g), dioxane (200mL) are heated to reflux 12 hours under nitrogen protection, cold But, add water, extracted with dichloromethane, dry, concentration, crude by column chromatography purifies to obtain product 11.6g, yield 67%.
Embodiment 1
The synthetic route of compound 1
The synthetic method of compound 1
In flask, intermediate A (1.5g, 5mmol), 4- carbazyls phenyl boric acid (1.4g, 5mmol), potassium carbonate is added (1.3g, 10mmol), tetra-triphenylphosphine palladium (0.05g), tetrahydrofuran (20mL) and water (10mL), are heated back under nitrogen protection Stream 12 hours, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product purifies to obtain 1.7g, yield 74% through column chromatography.
The synthetic method of other embodiment is to use intermediate A or B as original as the synthetic method of compound 1 Material, table 1 specific as follows：
The raw material and yield of 1 other embodiment of table
Embodiment 12-16
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 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the TAPC that 50nm thickness is 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 shine based on the compounds of this invention Material, and the Ir (ppy) for being 3% with weight ratio3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB 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.
Comparative example 1
In addition to use CBP replace the compounds of this invention as material of main part other than, comparative example 1 and embodiment 12-16 prepare device Method it is the same.
Embodiment 12-16 and device (structural schematic diagram is shown in Fig. 1) the Photo Research prepared by comparative example 1 PR650 spectrometers measure in 5000cd/m2Brightness under current efficiency be such as table 2.
2 current efficiency test result of table
Embodiment Compound Current efficiency (cd/A) Luminescent color
12 1 52 Green light
13 2 55 Green light
14 11 56 Green light
15 16 58 Green light
16 56 52 Green light
Comparative example 1 CBP 45 Green light
The structural formula of compound described in device is as follows：
From table 2 it can be seen that the benzazolyl compounds 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.As described above, the benzazolyl compounds of the present invention have The organic electroluminescence device of high stability, preparation has high efficiency and optical purity.
Embodiment 17-22
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention
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, NPB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq of 37.5nm thickness is deposited on the hole transport layer3, 1%C545T is as luminescent layer 140 for doping.
Then, 37.5nm thickness the compounds of this invention is deposited on the light-emitting layer as electron transfer layer 150.
Finally, vapor deposition 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is shown in Fig. 2) with Photo Research PR650 spectrometers measure 20mA/cm2Current density under efficiency such as table 3.
Comparative example 2
In addition to electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 17-22.
Embodiment 17-22 and device (structural schematic diagram is shown in Fig. 2) the Photo Research prepared by comparative example 2 PR650 spectrometers measure in 20mA/cm2Current density under efficiency such as table 3.
The test result of 3 current efficiency of table
Embodiment Compound Power efficiency (lm/W) Color
17 28 6.6 Green light
18 29 6.4 Green light
19 36 6.5 Green light
20 41 6.3 Green light
21 46 6.3 Green light
22 54 6.7 Green light
Comparative example 2 Alq3 5.0 Green light
Under the same conditions, the organic electroluminescence prepared as electron transport material using the benzazolyl compounds of the present invention is sent out The current efficiency of optical device is higher than comparative example, as described above, the compound of the present invention has high stability, prepared by the present invention Organic electroluminescence device has 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 (10)

1. a kind of benzazolyl compounds, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, Ar be selected from substitution either the aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 heteroaryl, take Generation either the triaromatic amine base of two aromatic aminos of unsubstituted C12-C30, substitution or unsubstituted C18-C30, substitution or The indyl of the carbazyl of unsubstituted C12-C30, substitution or unsubstituted C8-C30；
R1-R3Independently selected from the aryl of the alkyl of C1-C12, substitution or unsubstituted C6-C30.
2. benzazolyl compounds as described in claim 1, which is characterized in that Ar be selected from phenyl, naphthalene, xenyl, three and phenyl, Anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, The N- aryl of C6-C30, the alkyl-substituted carbazyl of C1-C4, indyl, carbazole indyl, fluorenes carbazyl 9,9- be Spirofluorene-based, The triaromatic amine base of C18-C60, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted dibenzofurans Base, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, Quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene.
3. benzazolyl compounds as claimed in claim 2, which is characterized in that the aryl and the alkyl that heteroaryl is C1-C12 take Generation.
4. benzazolyl compounds as described in claim 1, which is characterized in that R1-R3Independently selected from methyl, ethyl, propyl, different Propyl, tertiary butyl, normal-butyl, n-hexyl, phenyl.
5. benzazolyl compounds as described in claim 1, which is characterized in that be the compound of following structural 1-58：
6. application of the benzazolyl compounds 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, electron transfer layer, which is characterized in that institute It states at least one layer in organic layer and contains benzazolyl compounds as described in claim 1.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that benzazolyl compounds described in claim 1 The layer at place is luminescent layer and at least one layer in electron transfer layer.
9. organic electroluminescence device as claimed in claim 7, which is characterized in that benzazolyl compounds described in claim 1 It is used alone, or is used in mixed way with other compounds.
10. organic electroluminescence device as claimed in claim 7, which is characterized in that a kind of be selected from such as right is wanted is used alone The benzazolyl compounds of the structural formula 1-58 described in 5 are sought, or are selected from structural formula as claimed in claim 5 using two or more simultaneously The benzazolyl compounds of 1-58.
CN201810124395.4A 2018-02-07 2018-02-07 A kind of benzazolyl compounds and application thereof and organic electroluminescence device Pending CN108358895A (en)

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CN111326665A (en) * 2018-12-17 2020-06-23 固安鼎材科技有限公司 New material and electroluminescent device thereof

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Publication number Priority date Publication date Assignee Title
CN101205210A (en) * 2007-12-19 2008-06-25 华东理工大学 Indole derivatives and uses thereof
CN101636468A (en) * 2007-02-06 2010-01-27 住友化学株式会社 Contain the composition of benzazolyl compounds and use said composition and the luminous element that obtains
CN104725296A (en) * 2013-12-24 2015-06-24 北京鼎材科技有限公司 Indole derivative and application thereof to organic electroluminescence

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Publication number Priority date Publication date Assignee Title
CN101636468A (en) * 2007-02-06 2010-01-27 住友化学株式会社 Contain the composition of benzazolyl compounds and use said composition and the luminous element that obtains
CN101205210A (en) * 2007-12-19 2008-06-25 华东理工大学 Indole derivatives and uses thereof
CN104725296A (en) * 2013-12-24 2015-06-24 北京鼎材科技有限公司 Indole derivative and application thereof to organic electroluminescence

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111326665A (en) * 2018-12-17 2020-06-23 固安鼎材科技有限公司 New material and electroluminescent device thereof
CN111326665B (en) * 2018-12-17 2023-08-22 固安鼎材科技有限公司 New material and electroluminescent device thereof

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