CN107935999A - A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device - Google Patents
A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device Download PDFInfo
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Abstract
The present invention provides a kind of naphtho- benzofuran compound, it is with following structural formula：The naphtho- benzofuran compound has preferable stability, it can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field, during for organic electroluminescence device, operating voltage can be reduced, device efficiency is improved, is the phosphorescent light body material with excellent performance.Present invention also offers a kind of organic electroluminescence device, 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 naphtho- benzofuran compound have higher luminous efficiency and optical purity.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of naphtho- benzofuran compound and its use
On the way, a kind of organic electroluminescence device is further related to.
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.The electronics produced by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer by the hole that anode produces
Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique
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 apply on flat-panel monitor and a new generation's illumination, can also conduct
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been 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 produced so that organic material easily crystallizes, and have impact on service life and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application also greatly carry
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, common to be 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
For material of main part when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
Easily transmitted and the characteristic of the difficult flowing of electronics in the hole of CBP so that the charge unbalance of luminescent layer, as a result reduces the effect of device
Rate.
The content of the invention
The present invention provides a kind of naphtho- benzofuran compound, it is the compound with following structural formula I：
Wherein, Ar is selected from the aryl of the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30, takes
Generation or heteroaryl, triaromatic amine base, carbazyl and the triaryl phosphinyl of unsubstituted C3-C30；
X is selected from O, S, CR1R2And NR3；
R1-R3Independently selected from C1-C12 alkyl, the substitution of C6-C30 or unsubstituted aryl.
Optionally, Ar is selected from phenyl, naphthyl, three simultaneously phenyl, the N- aryl of C6-C30, the alkyl-substituted carbazole of C1-C4
Base, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted aryl) fluorenes
Base, 9,9- are Spirofluorene-based, the triaromatic amine base of C6-C60, substitution either unsubstituted dibenzothiophene and substitution or unsubstituted
Dibenzofuran group, above group further substitutes by the aryl of the alkyl of C1-C8 or C3-C10.
Optionally, the heteroaryl is selected from pyridine radicals, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazole
Base, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophenes
Base and imidazole radicals.
Optionally, R1-R3Independently selected from methyl, ethyl, phenyl, tolyl.
Optionally, naphtho- benzofuran compound is the compound of following structural 1-48：
The naphtho- benzofuran compound of the present invention can be applied in organic electroluminescence device, also can be widely used to
Organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.
Present invention also offers 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 or electron transfer layer
Layer；
Optionally, 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.
Optionally, the organic layer where the naphtho- benzofuran compound is luminescent layer.
Optionally, the compound in the luminescent layer is at least one of structural formula 1-48 compound or is knot
The compound of structure formula 1-48 and the mixture of other compounds.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound conduct with structural formula I
As material of main part, its concentration is the 20-99.9% of whole luminous layer weight, excellent for material of main part, the wherein compound of structural formula I
Select 40-99%.
The gross 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.It can include other small molecules and macromolecule is organic
Compound, includes but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, six cyano group, 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 adjust as needed
The scope of visible ray.Except the present invention have Compounds of structural formula I as phosphorescent light body material in addition to, can also arrange in pairs or groups other phosphorescence
Material of main part, phosphorescence light emitting guest material can be included selected from least one of ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium metal
Metal-organic complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
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
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound and 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 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 and magnesia, these compounds can be independent
Using 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
Prepared with vapour deposition method or sputtering method.
Device experimental shows that the compound of naphtho- benzofuran of the present invention as described in structural formula I, has preferable thermostabilization
Property, high-luminous-efficiency, high luminance purity.It is good with electroluminescent efficiency using the organic electroluminescence device that the compound makes
Good and excitation purity is excellent and the advantages of long lifespan.
Brief 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 resistance
Barrier, 160 be luminescent layer, and 170 be electron transfer layer, and 180 be electron injecting layer, and 190 be cathode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of compound 1
In flask, bromo- 7, the 7- dimethyl -5- phenyl of 2--indenes [2,1-B] and carbazole (2.5g, 5.7mmol), naphthalene are added
And benzofuran -3- boric acid (1.5g, 5.7mmol), potassium carbonate (1.6g, 11.4mmol), tetrahydrofuran (30mL) and water
(10mL), add tetra-triphenylphosphine palladium (0.1g), under nitrogen gas shielded, be heated to reflux 6 it is small when, react, cooling, use dichloro
Methane extracts three times, and organic layer is dried with anhydrous sodium sulfate, removes solvent, and crude by column chromatography purifies to obtain 2.6g, yield
For 81%.
Embodiment 2
The synthetic route of compound 7
Synthetic method is as the synthesis of compound 1, and raw materials used is 2- benzos naphtho- [2,3-d] furan boronic acid, yield
For 77%.
Embodiment 3
The synthetic route of compound 25
The synthetic method of intermediate 25-1
For synthetic method as with compound 1, raw materials used is bis- bromo nitrobenzene of 4- dibenzofurans boric acid and 2,4-, production
Rate is 52%.
The synthetic method of intermediate 25-2
In flask, intermediate 25-1 (2.7g, 7.4mmol), triphenylphosphine (4.8g, 18.4mmol), adjacent dichloro are added
Benzene (50mL), be heated to reflux under nitrogen protection 6 it is small when, cooling, removes solvent, crude by column chromatography purifies to obtain product
1.7g, yield 69%.
The synthetic method of intermediate 25-3
In flask, addition intermediate 25-2 (1.7g, 5.1mmol), iodobenzene (1.6g, 7.6mmol), potassium carbonate (1.4g,
10mmol), cuprous iodide (0.2g), Phen (0.2g), o-dichlorohenzene (20mL), it is small to be heated to reflux 10 under nitrogen protection
When, cooling removes solvent, and crude by column chromatography purifies to obtain 1.6g, yield 74%.
The synthetic method of compound 25
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 25-3 and naphtho- benzofuran -3- boron
Acid, yield 59%.
Embodiment 4
The synthetic route of compound 29
For synthetic method as with compound 1, raw materials used is intermediate 25-3 and 2- benzo naphtho- [2,3-d] furans boron
Acid, yield 66%.
Embodiment 5
The synthesis of compound 46
The synthetic method of intermediate 46-1
For synthetic method as with intermediate 25-1, raw materials used is bis- bromo nitrobenzene of 4- dibenzothiophenes and 2,5-, production
Rate is 68%.
The synthetic method of intermediate 46-2
Synthetic method is as with intermediate 25-2, and raw materials used is intermediate 46-2, yield 63%.
The synthetic method of intermediate 46-3
Synthetic method is as with intermediate 25-3, and raw materials used is intermediate 46-3, yield 67%.
The synthetic method of compound 46
For synthetic method as with compound 1, raw materials used is intermediate 46-3 and 2- benzo naphtho- [2,3-d] furans boron
Acid, yield 54%.
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) pass through successively：Deionized water, ethanol, acetone and deionized water are 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 for 50nm thickness being 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, luminescent layer includes：Weight ratio is 46%
The compounds of this invention, weight ratio be 46% PH1 and weight ratio be 8% Ir (ppy)3, wherein, the compounds of this invention conduct
Material of main part, Ir (ppy)3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, evaporation 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structure diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
5000cd/m2Brightness under external quantum efficiency be such as table 1.
Comparative example
The method that comparative example prepares device is consistent with the preparation method of embodiment 6-10, except replacing the present inventionization with PH2
Compound as material of main part outside.
Table 1
| Embodiment | Compound | Current efficiency (cd/A) | Glow color |
| 6 | 1 | 67 | Green light |
| 7 | 7 | 68 | Green light |
| 8 | 25 | 66 | Green light |
| 9 | 29 | 65 | Green light |
| 10 | 46 | 64 | Green light |
| Comparative example | PH2 | 53 | Green light |
The structural formula of compound described in device is as follows：
As it can be seen from table 1 the naphtho- benzofuran compound of the present invention is used for organic electroluminescence device, can reduce
Operating voltage, improves device efficiency, is the phosphorescent light body material with excellent performance.As described above, the compound tool of the present invention
There is high stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
Preferred embodiment of the invention described in detail above.It should be appreciated that those of ordinary skill in the art without
Need creative work to conceive according to the present invention and make 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 naphtho- benzofuran compound, it is characterised in that it is the compound with following structural formula I：
Wherein, Ar be selected from the alkyl of C1-C12, the alkoxy of C1-C8, the aryl of substitution or unsubstituted C6-C30, substitution or
Heteroaryl, triaromatic amine base, carbazyl and the triaryl phosphinyl of the unsubstituted C3-C30 of person；
X is selected from O, S, CR1R2And NR3；
R1-R3Independently selected from C1-C12 alkyl, the substitution of C6-C30 or unsubstituted aryl.
2. naphtho- benzofuran compound as claimed in claim 1, it is characterised in that Ar is selected from phenyl, naphthyl, three acenes
Base, the N- aryl of C6-C30, the alkyl-substituted carbazyl of C1-C4, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- bis-
Alkyl) fluorenyl, (9,9- bis- substitutes or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, C6-C60 triaromatic amine base, substitution
Either unsubstituted dibenzothiophene and substitution or unsubstituted dibenzofuran group, above group is further by C1-C8
Alkyl or C3-C10 aryl substitution.
3. naphtho- benzofuran compound as claimed in claim 1, it is characterised in that the heteroaryl is selected from pyridine radicals, phonetic
Piperidinyl, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoline
Quinoline base, azepine dibenzofuran group, azepine dibenzothiophene and imidazole radicals.
4. naphtho- benzofuran compound as claimed in claim 1, it is characterised in that R1-R3Independently selected from methyl, ethyl,
Phenyl and tolyl.
5. naphtho- benzofuran compound as claimed in claim 1, it is characterised in that be the chemical combination of following structural 1-48
Thing：
6. application of the naphtho- benzofuran compound in organic electroluminescence device described in claim 1.
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 or electron transfer layer, it is characterised in that institute
State at least one layer in organic layer and contain naphtho- benzofuran compound as claimed in claim 1.
8. organic electroluminescence device as claimed in claim 7, it is characterised in that where the naphtho- benzofuran compound
Organic layer be luminescent layer.
9. organic electroluminescence device as claimed in claim 7, it is characterised in that the compound in the luminescent layer is right
It is required that at least one of 5 described structural formula 1-48 compounds or compound and other compounds for the structural formula 1-48
Mixture.
10. organic electroluminescence device as claimed in claim 7, it is characterised in that the gross thickness of the organic layer is 1-
1000nm。
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711214553.7A CN107935999A (en) | 2017-11-28 | 2017-11-28 | A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device |
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| CN201711214553.7A CN107935999A (en) | 2017-11-28 | 2017-11-28 | A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device |
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| CN201711214553.7A Pending CN107935999A (en) | 2017-11-28 | 2017-11-28 | A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109053698A (en) * | 2018-09-19 | 2018-12-21 | 上海道亦化工科技有限公司 | A kind of aromatic amine compound and luminescent device containing dibenzofurans |
| CN111116658A (en) * | 2018-10-30 | 2020-05-08 | 上海和辉光电有限公司 | Organic light-emitting material and OLED device comprising same |
| CN111269243A (en) * | 2018-12-05 | 2020-06-12 | 北京鼎材科技有限公司 | Organic electroluminescent compound and application thereof |
| KR20210088501A (en) * | 2018-12-17 | 2021-07-14 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN115385922A (en) * | 2021-05-25 | 2022-11-25 | 江苏三月科技股份有限公司 | Azadibenzofurans-modified triazine compound and organic electroluminescent device |
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| CN106543152A (en) * | 2016-10-25 | 2017-03-29 | 上海道亦化工科技有限公司 | Phosphorescence host compound and its organic luminescent device based on naphtho- benzofuran |
| CN106632360A (en) * | 2016-09-27 | 2017-05-10 | 上海道亦化工科技有限公司 | Compound based on benzofuroindole and organic electroluminescent device thereof |
| CN106883204A (en) * | 2017-03-30 | 2017-06-23 | 上海道亦化工科技有限公司 | Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans |
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| CN106632360A (en) * | 2016-09-27 | 2017-05-10 | 上海道亦化工科技有限公司 | Compound based on benzofuroindole and organic electroluminescent device thereof |
| CN106543152A (en) * | 2016-10-25 | 2017-03-29 | 上海道亦化工科技有限公司 | Phosphorescence host compound and its organic luminescent device based on naphtho- benzofuran |
| CN106883204A (en) * | 2017-03-30 | 2017-06-23 | 上海道亦化工科技有限公司 | Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109053698A (en) * | 2018-09-19 | 2018-12-21 | 上海道亦化工科技有限公司 | A kind of aromatic amine compound and luminescent device containing dibenzofurans |
| CN111116658A (en) * | 2018-10-30 | 2020-05-08 | 上海和辉光电有限公司 | Organic light-emitting material and OLED device comprising same |
| CN111269243A (en) * | 2018-12-05 | 2020-06-12 | 北京鼎材科技有限公司 | Organic electroluminescent compound and application thereof |
| KR20210088501A (en) * | 2018-12-17 | 2021-07-14 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR102373110B1 (en) | 2018-12-17 | 2022-03-11 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN115385922A (en) * | 2021-05-25 | 2022-11-25 | 江苏三月科技股份有限公司 | Azadibenzofurans-modified triazine compound and organic electroluminescent device |
| CN115385922B (en) * | 2021-05-25 | 2024-04-23 | 江苏三月科技股份有限公司 | Azadibenzofuran modified triazine compound and organic electroluminescent device |
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