CN109705021A - A kind of organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl and application thereof and luminescent device - Google Patents
A kind of organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl and application thereof and luminescent device Download PDFInfo
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- CN109705021A CN109705021A CN201910060327.0A CN201910060327A CN109705021A CN 109705021 A CN109705021 A CN 109705021A CN 201910060327 A CN201910060327 A CN 201910060327A CN 109705021 A CN109705021 A CN 109705021A
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- electroluminescent compounds
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Abstract
The present invention provides a kind of organic electroluminescent compounds of alkylnaphthalene containing cycloheptyl, 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 alkylnaphthalene containing cycloheptyl
Compound and application thereof 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 alkylnaphthalene containing cycloheptyl, to have the following structure Formulas I
Compound:
Wherein, L is selected from the aryl of singly-bound, substitution or unsubstituted C6-C30；
Ar1Aryl selected from substitution or unsubstituted C6-C30；
Ar2The heteroaryl of aryl, substitution or unsubstituted C3-C30 selected from substitution or unsubstituted C6-C30.
Preferably, the Ar1Selected from phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl,
Fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9,9- spiral shell, two fluorenyl.Ar1It can further be taken by the alkyl of C1-C12
Generation.
Preferably, the Ar2Selected from phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl,
Fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9,9- spiral shell, two fluorenyl, dibenzothiophene, dibenzofuran group, click
Oxazolyl, 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.Ar2Can further by
The alkyl of C1-C12 replaces.
Preferably, the organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl are the chemical combination of following structural 1-66
Object:
The organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl 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 alkylnaphthalene containing cycloheptyl 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 alkylnaphthalene containing cycloheptyl is luminescent layer.
The organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl 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 alkylnaphthalene containing cycloheptyl 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 alkylnaphthalene containing cycloheptyl of structure formula 1-66, or it is selected from structural formula 1-66's using two or more simultaneously
The organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl.
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.It can choose following compound, but
It is not limited to this: oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics effectively can be injected into organic layer 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 cycloheptyl alkylnaphthalene 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
The synthetic method of intermediate A
In flask, it is added bromo dibenzocycloheptane benzene naphthalene (18g, 47mmol), ortho-nitrophenyl boric acid (8.6g,
51mmol), potassium carbonate (13.6g, 100mmol), tetrahydrofuran (300mL), water (150mL), tetra-triphenylphosphine palladium (1g), in nitrogen
Heating 12 hours back, cooling under gas shielded, is extracted with dichloromethane, dry, and concentration, crude by column chromatography purifies to obtain
14g, yield 75%.
The synthetic method of intermediate B
In flask, it is added intermediate C (20g, 50mmol), the triethyl phosphite of 100mL is heated to reflux 5 hours, cold
But, extra triethyl phosphite is removed under reduced pressure, crude product obtains product 10.8g, yield 59% through column chromatographic purifying.Intermediate
The synthetic method of C
Synthetic method is as the synthesis of intermediate A, yield 61%.
The synthetic method of intermediate D
Synthetic method is as the synthesis of intermediate B, yield 49%.
Embodiment 2
The synthetic route of compound 5
The synthetic method of compound 5
In flask, it is added intermediate B (2g, 5.4mmol), bromo phenanthrene (1.7g, 5.4mmol), sodium tert-butoxide (1g,
10mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL) are heated to reflux 15 hours under nitrogen protection, cooling, are removed
Solvent is removed, crude by column chromatography purifies to obtain 2.2g, yield 69%.
The synthesis of other embodiments compound as the synthesis of 1 compound 5 of embodiment, it is raw materials used for intermediate B or
Person's intermediate D is reacted with other halides, table 1 specific as follows:
1 raw material of table and yield
Embodiment 14
The synthetic route of compound 29
The synthetic method of compound 29
In flask, intermediate C (2g, 5.4mmol), n,N-Dimethylformamide (20mL), sodium hydride are sequentially added
Chloro- 4, the 6- diphenyl triazine (1.45g, 5.4mmol) of (12mmol), 2- stirs 5 hours, adds water, filters, and again with toluene is tied again
Crystalline substance obtains product 2.6g, yield 79%.
Embodiment 15
The synthetic route of compound 53
Synthetic method is as compound 29, yield 68%.
Embodiment 16-29
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 PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) of spin coating 45nm thickness is on ITO
It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the TAPC that 45nm 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 with the Ir of 5% weight ratio (pq)2Acac adulterates guest materials as phosphorescence.
Then, the TmPYPB of 55nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 0.6nm 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
10000cd/m2Brightness under external quantum efficiency be such as table 2.
Comparative example 1
The device of comparative example preparation is as embodiment 16-29 device preparation method, in addition to replacing chemical combination of the present invention with CBP
Object as material of main part outside.Prepared device (structural schematic diagram is shown in Fig. 1) is surveyed with Photo Research PR650 spectrometer
In 10000cd/m2Brightness under external quantum efficiency be such as table 2.
2 test result of table
The structural formula of compound described in device is as follows:
From Table 2, it can be seen that the organic electroluminescent compounds of the alkylnaphthalene of the invention containing cycloheptyl are used for organic electroluminescence
Luminescent device can reduce operating voltage, improve device efficiency, be the phosphorescent light body material with excellent performance.As described above,
The compound of the present invention has high stability, and the organic electroluminescence device of preparation has high efficiency and optical purity.
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 alkylnaphthalene containing cycloheptyl, which is characterized in that be the chemical combination for having the following structure Formulas I
Object:
Wherein, L is selected from the aryl of singly-bound, substitution or unsubstituted C6-C30；
Ar1Aryl selected from substitution or unsubstituted C6-C30；
Ar2The heteroaryl of aryl, substitution or unsubstituted C3-C30 selected from substitution or unsubstituted C6-C30.
2. the organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl as described in claim 1, which is characterized in that the Ar1It is selected from
Phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- bis-
Phenylfluorenyl, 9,9- spiral shell, two fluorenyl.
3. the organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl as described in claim 1, which is characterized in that the Ar2It is selected from
Phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- bis-
Phenylfluorenyl, 9,9- spiral shell, two fluorenyl, dibenzothiophene, dibenzofuran group, carbazyl, pyridyl group, pyrimidine radicals, pyridazinyl,
Triazine radical, imidazole radicals, oxazolyl, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine two
Benzofuranyl, azepine dibenzothiophene, imidazole radicals.
4. the organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl as described in claim 1, which is characterized in that be having structure
The compound of formula 1-66:
5. organic electroluminescent compounds the answering in organic electroluminescence device of the alkylnaphthalene described in claim 1 containing cycloheptyl
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 alkylnaphthalene containing cycloheptyl as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that alkyl containing cycloheptyl described in claim 1
Layer where the organic electroluminescent compounds of naphthalene is luminescent layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that alkyl containing cycloheptyl described in claim 1
The organic electroluminescent compounds of naphthalene 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 alkylnaphthalene containing cycloheptyl of structural formula 1-66 described in 4, or simultaneously using two or more selected from such as
The organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl of structural formula 1-66 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110746401A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN112430230A (en) * | 2019-08-26 | 2021-03-02 | 北京鼎材科技有限公司 | Organic compound and organic electroluminescent device containing the same |
| CN113004189A (en) * | 2019-12-18 | 2021-06-22 | 北京鼎材科技有限公司 | Compound and application thereof |
-
2019
- 2019-01-22 CN CN201910060327.0A patent/CN109705021A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112430230A (en) * | 2019-08-26 | 2021-03-02 | 北京鼎材科技有限公司 | Organic compound and organic electroluminescent device containing the same |
| CN112430230B (en) * | 2019-08-26 | 2024-02-09 | 北京鼎材科技有限公司 | Organic compound and organic electroluminescent device containing the same |
| CN110746401A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN113004189A (en) * | 2019-12-18 | 2021-06-22 | 北京鼎材科技有限公司 | Compound and application thereof |
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Application publication date: 20190503 |