CN109232584A - A kind of organic electroluminescent compounds and luminescent device of the spiral shell containing benzimidazole - Google Patents
A kind of organic electroluminescent compounds and luminescent device of the spiral shell containing benzimidazole Download PDFInfo
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Abstract
The present invention provides a kind of organic electroluminescent compounds of spiral shell containing benzimidazole, have the following structure formula:The compound has 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 compound containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device that the compound makes.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescent of the spiral shell containing benzimidazole
Compound further relates to a kind of organic electroluminescence device.
Background technique
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 according to need the material by changing luminescent layer to adjust
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 and 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, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, 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 lower than 25%, and promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly mention
The high efficiency of organic electroluminescence device.Generally, electroluminescent phosphorescence needs commonly to be used as phosphorus using host-guest system technology
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
It is easily transmitted and the characteristic of electronics difficulty flowing in the hole of CBP, so that the charge unbalance of luminescent layer, as a result reduces the effect of device
Rate.
Summary of the invention
The present invention provides a kind of organic electroluminescent compounds of spiral shell containing benzimidazole, to have the following structure Formulas I
Compound:
Wherein, R1-R5、R8-R9、R13-R16Independently selected from hydrogen, deuterium, fluorine, the alkyl of C1-C12, substitution or unsubstituted
The aryl of C6-C30；R6、R7、R10、R11、R12Aryl independently selected from hydrogen, deuterium, fluorine, substitution or unsubstituted C6-C30 takes
Generation or the carbazyl of unsubstituted C12-C30, the indyl of substitution or unsubstituted C8-C30, substitution or unsubstituted
Two aromatic aminos of C12-C30, the triaromatic amine base of substitution or unsubstituted C18-C30, substitution or unsubstituted C13-
The acridinyl of C30, the phenoxazine base of substitution or unsubstituted C12-C30, substitution or unsubstituted C12-C30 phenthazine
Base, and R1-R16It is not simultaneously hydrogen.
Preferably, R1-R5、R8-R9、R13-R16Independently selected from hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, butyl, uncle
Butyl, hexyl, cyclohexyl.
Preferably, R6、R7、R10、R11、R12Independently selected from following group or following group further by the alkane of C1-C12
Base replace group: phenyl, naphthalene, xenyl, diphenyl phenyl, phenyl napthyl, three and phenyl, anthryl, phenanthryl, pyrenyl,
Base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, three fragrance
Amido, dibenzothiophene, dibenzofuran group, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyl, thiazole
Base, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophenes
Base, imidazole radicals.
Preferably, the organic electroluminescent compounds of the spiral shell containing benzimidazole are the chemical combination of following structural 1-70
Object:
The organic electroluminescent compounds of the spiral shell containing benzimidazole of the invention can be applied to organic electroluminescence device, too
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
Include 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 organic electroluminescent compounds containing the spiral shell containing benzimidazole 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.
Preferably, the layer where the organic electroluminescent compounds of the spiral shell containing benzimidazole is luminescent layer.
The organic electroluminescent compounds of the spiral shell containing benzimidazole as described in structural formula I are used alone, or with other chemical combination
Object is used in mixed way；The organic electroluminescent compounds of the spiral shell containing benzimidazole as described in structural formula I can be used alone therein
A kind of compound, can also be simultaneously using two or more the compound in structural formula I；It is used alone a kind of selected from knot
The organic electroluminescent compounds of the spiral shell containing benzimidazole of structure formula 1-70, or it is selected from structural formula 1-70's using two or more simultaneously
The organic electroluminescent compounds of the spiral shell containing benzimidazole.
The overall thickness of organic electroluminescence device organic layer of the 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 organic electroluminescence device of the 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.In addition to can be used with the compound of the present invention
It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine
Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano six
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'-
TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Except it is of the invention there is Compounds of structural formula I in addition to, 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
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.Except of the invention has structural formula I
Outside compound, it is also an option that following compound, but not limited to this: oxa- oxazole, thiazole compound, triazole chemical combination
Object, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic chemical combination
Object, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazole
Compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention
In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex can choose following compound, but not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or 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 that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the 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 the organic electroluminescent compounds of containing benzimidazole spiral shell of the present invention as described in structural formula I, tool
There are preferable thermal stability, high-luminous-efficiency, high luminance purity.Organic electroluminescence device using compound production has electricity
The advantage that photoluminescence efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the 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.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of intermediate B
The synthetic method of intermediate A
In flask, the bromo- 2- fluorobenzaldehyde (20g, 0.1mol) of 4-, benzimidazole (12g, 0.1mol), water are sequentially added
It closing ferric trichloride (10mmol), potassium phosphate (0.2mol) and DMF (200mL) react 20 hours at 120 DEG C, and it is cooling, add water,
It is extracted with dichloromethane, dry, concentration, product obtains product 21.7g, yield 73% through column chromatographic purifying out.
The synthetic method of intermediate B
It in flask, sequentially adds intermediate A (20g, 57mmol), anhydrous tetrahydro furan (250mL), under room temperature, slowly
Be added 2- xenyl magnesium bromide grignard reagent (75mmol), be heated to reflux 2 hours, it is cooling, be slowly added to dilute hydrochloric acid adjust pH to
7, it is extracted with dichloromethane, is concentrated, acetic acid (200mL) and concentrated hydrochloric acid (10mL) is added, is heated to reflux 5 hours, it is cooling, it removes molten
Agent, is added ethyl alcohol, and filtering is dried to obtain product 18g, yield 73%.
Embodiment 2
The synthetic route of intermediate D
The synthetic method of intermediate C
Its synthetic method replaces the bromo- 2- fluorobenzaldehyde of 4- such as intermediate A, with the bromo- 2- fluorobenzaldehyde of raw material 5-, produces
Rate 69%.
The synthetic method of intermediate D
For its synthetic method as the synthesis of intermediate B, raw materials used is intermediate C, yield 65%.
Embodiment 3
The synthetic route of compound 1
The synthetic method of compound 1
It in flask, sequentially adds intermediate B (2.5g, 5.8mmol), carbazole (1g, 5.8mmol), sodium tert-butoxide
It is small to be heated to reflux 15 under nitrogen protection for (2.1g, 22mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL)
When, it is cooling, solvent is removed, crude by column chromatography purifies to obtain 1.62g, yield 54%.
As the synthesis of compound 1, raw materials used is raw material table 1 specific as follows for the synthesis of other embodiments compound:
1 raw material of table and yield
Embodiment 8
The synthesis of compound 43
It in flask, sequentially adds intermediate B (3g, 6.9mmol), 9- phenyl carbazole -3- boric acid (2g, 11mmol), carbon
Sour potassium (1.9g, 14mmol), tetrahydrofuran (30mL), water (15mL), tetra-triphenylphosphine palladium (0.1g) heat under nitrogen protection
It is 12 hours back, cooling, it is extracted with dichloromethane, dry, concentration, crude by column chromatography purifies to obtain 3.2g, yield 79%.
As the synthesis of compound 43, raw materials used is raw material table 2 specific as follows for the synthesis of other embodiments compound:
2 raw material of table and yield
Embodiment 13-22
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share
Department) successively pass through: 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 is 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 spectrometer measure
5000cd/m2Brightness under current efficiency be such as table 3.
Comparative example 1
Device prepared by comparative example 1 is as embodiment 13-22 device preparation method, in addition to replacing the present inventionization with CBP
Close object as material of main part outside.
3 experimental result of table
From table 3 it can be seen that organic electroluminescence compound of the invention is used for organic electroluminescence device, work can be reduced
Voltage improves device efficiency, is the phosphorescent light body material with excellent performance.As described above, the compound of the present invention has height
Stability, the organic electroluminescence device of preparation 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 within the scope of protection determined by the claims.
Claims (10)
1. a kind of organic electroluminescent compounds of spiral shell containing benzimidazole, which is characterized in that be the chemical combination for having the following structure Formulas I
Object:
Wherein, R1-R5、R8-R9、R13-R16Independently selected from hydrogen, deuterium, fluorine, the alkyl of C1-C12, substitution or unsubstituted C6-
The aryl of C30；R6、R7、R10、R11、R12Aryl, substitution independently selected from hydrogen, deuterium, fluorine, substitution or unsubstituted C6-C30
The either carbazyl of unsubstituted C12-C30, the indyl of substitution or unsubstituted C8-C30, substitution or unsubstituted
Two aromatic aminos of C12-C30, the triaromatic amine base of substitution or unsubstituted C18-C30, substitution or unsubstituted C13-
The acridinyl of C30, the phenoxazine base of substitution or unsubstituted C12-C30, substitution or unsubstituted C12-C30 phenthazine
Base, and R1-R16It is not simultaneously hydrogen.
2. the organic electroluminescent compounds of the spiral shell containing benzimidazole as described in claim 1, which is characterized in that R1-R5、R8-R9、
R13-R16Independently selected from hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, cyclohexyl.
3. the organic electroluminescent compounds of the spiral shell containing benzimidazole as described in claim 1, which is characterized in that R6、R7、R10、
R11、R12Independently selected from following group or following group further by the alkyl-substituted group of C1-C12: phenyl, naphthalene,
Xenyl, diphenyl, phenyl napthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl,
(9,9- bis- replace or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, triaromatic amine base, dibenzothiophene, dibenzo furan
It mutters base, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyl, thiazolyl, thiadiazolyl group, quinolyl, isoquinolin
Base, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals, carbazyl.
4. the organic electroluminescent compounds of the spiral shell containing benzimidazole as described in claim 1, which is characterized in that be having structure
The compound of formula 1-70:
5. organic electroluminescent compounds the answering in organic electroluminescence device of the spiral shell described in claim 1 containing benzimidazole
With.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
Implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, which is characterized in that institute
State at least one layer of organic electroluminescent compounds containing the spiral shell containing benzimidazole as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to contain benzimidazole
Layer where the organic electroluminescent compounds of spiral shell is luminescent layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to contain benzimidazole
The organic electroluminescent compounds of spiral shell are used alone, or are used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim
The organic electroluminescent compounds of the spiral shell containing benzimidazole of structural formula 1-70 described in 4, or simultaneously using two or more selected from such as
The organic electroluminescent compounds of the spiral shell containing benzimidazole of structural formula 1-70 as claimed in claim 4.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1-
1000nm。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110746442A (en) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | Imidazole spiro-containing compound and application thereof |
| KR20200102786A (en) * | 2019-02-22 | 2020-09-01 | 덕산네오룩스 주식회사 | Compound for organic electric element and organic electric device comprising the same |
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| WO2014058232A3 (en) * | 2012-10-10 | 2015-04-30 | 대주전자재료 주식회사 | Spiro-type organic material, and organic electroluminescent device using same |
| CN105481811A (en) * | 2015-12-18 | 2016-04-13 | 上海道亦化工科技有限公司 | Compound with screw structure and organic electroluminescent device thereof |
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| CN103304557A (en) * | 2012-03-15 | 2013-09-18 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing spirofluorene, preparation method thereof and organic light-emitting device |
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| WO2014058232A3 (en) * | 2012-10-10 | 2015-04-30 | 대주전자재료 주식회사 | Spiro-type organic material, and organic electroluminescent device using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110746442A (en) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | Imidazole spiro-containing compound and application thereof |
| KR20200102786A (en) * | 2019-02-22 | 2020-09-01 | 덕산네오룩스 주식회사 | Compound for organic electric element and organic electric device comprising the same |
| KR102611191B1 (en) | 2019-02-22 | 2023-12-08 | 덕산네오룩스 주식회사 | Compound for organic electric element and organic electric device comprising the same |
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