CN109651230A - A kind of organic electroluminescent compounds of the indoles containing naphtho- and application thereof and luminescent device - Google Patents

A kind of organic electroluminescent compounds of the indoles containing naphtho- and application thereof and luminescent device Download PDF

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CN109651230A
CN109651230A CN201910059460.4A CN201910059460A CN109651230A CN 109651230 A CN109651230 A CN 109651230A CN 201910059460 A CN201910059460 A CN 201910059460A CN 109651230 A CN109651230 A CN 109651230A
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organic electroluminescent
electroluminescent compounds
indoles
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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 organic electroluminescent compounds of indoles containing naphtho-, 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

A kind of organic electroluminescent compounds of the indoles containing naphtho- and application thereof and luminescent device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescent of the indoles containing naphtho- Object and application thereof is closed, a kind of organic electroluminescence device is further related to.
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 indoles containing naphtho-, are to have the following structure Formulas I Compound:
Wherein, L is selected from the aryl of singly-bound, substitution or unsubstituted C6-C30；
Ar1-Ar2Independently selected from hydrogen, deuterium, halogen, cyano, the alkyl of C1-C12, substitution or unsubstituted C6-C30 The heteroaryl of aryl, substitution or unsubstituted C3-C30；
R1-R8Independently selected from hydrogen, deuterium, halogen, cyano, C1-C12 alkyl.
Preferably, the L is selected from singly-bound or phenyl.
Preferably, the Ar1-Ar2Independently selected from phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, glimmering Anthryl, acenaphthenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9,9- spiral shell, two fluorenyl, dibenzothiophene, dibenzo Furyl, carbazyl, pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyl, thiazolyl, thiadiazolyl group, quinoline Base, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals.Ar1With Ar2Can also further it be replaced by the alkyl of C1-C12.
Preferably, the R1-R8Independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl.
Preferably, the organic electroluminescent compounds of the indoles containing naphtho- are the compound of following structural 1-56:
The organic electroluminescent compounds of the indoles containing naphtho- of the invention can be applied to organic electroluminescence device, the sun It can 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 indoles containing naphtho- 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 indoles containing naphtho- is luminescent layer.
The organic electroluminescent compounds of the indoles containing naphtho- as described in structural formula I are used alone, or with other compounds It is used in mixed way；The organic electroluminescent compounds of the indoles containing naphtho- as described in structural formula I can be used alone one such Compound, can also be simultaneously using two or more the compound in structural formula I；It is used alone a kind of selected from structural formula The organic electroluminescent compounds of the indoles containing naphtho- of 1-56, or contain naphtho- selected from structural formula 1-56 using two or more simultaneously The organic electroluminescent compounds of indoles.
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 naphtho- indoles of the present invention as described in structural formula I, has Preferable thermal stability, high-luminous-efficiency, high luminance purity.Had using the organic electroluminescence device of compound production electroluminescent The advantage that luminous 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, 2- nitro -1- naphthols (19g, 0.1mol), pyridine (10mL), methylene chloride are sequentially added (150mL) is slowly added to trifluoromethanesulfanhydride anhydride (36.6g, 0.13mol) under ice bath, reacts 12 hours at normal temperature, adds water quenching It goes out, is obtaining product 25g, yield 79% through column chromatographic purifying.
The synthetic method of intermediate B
In flask, intermediate A (20g, 78mmol), phenyl fluorenes borate (35g, 78mmol), potassium carbonate are sequentially added (20g, 150mmol), tetrahydrofuran (300mL), water (150mL), tetra-triphenylphosphine palladium (1g), are heated to reflux under nitrogen protection It is 12 hours, cooling, it is extracted with dichloromethane, dry, concentration, crude by column chromatography purifies to obtain product 26g, yield 68%.
The synthetic method of intermediate C
In flask, the triethyl phosphite of intermediate B (25g, 51mmol), 100mL is added, is heated to reflux 5 hours, it is cold But, extra triethyl phosphite is removed under reduced pressure, crude product obtains product 15g, yield 64% through column chromatographic purifying.
Embodiment 2
The synthetic route of compound 3
The synthetic method of compound 3
In flask, intermediate C (2g, 4.4mmol), bromo phenanthrene (1.4g, 4.4mmol), sodium tert-butoxide are sequentially added (1g, 10mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (30mL), are heated to reflux 15 hours under nitrogen protection, It is cooling, solvent is removed, crude by column chromatography purifies to obtain product 2.3g, yield 76%.
The synthesis of other embodiments compound as the synthesis of 1 compound 3 of embodiment, it is raw materials used for intermediate C with The reaction of other halides, table 1 specific as follows:
1 raw material of table and yield
Embodiment 12
The synthetic route of compound 26
In flask, intermediate C (2g, 4.4mmol), n,N-Dimethylformamide (20mL), sodium hydride are sequentially added Chloro- 4, the 6- diphenyl triazine (1.2g, 4.4mmol) of (10mmol), 2- stirs 5 hours, adds water, filters, and again with toluene is tied again Crystalline substance obtains product 2.5g, yield 83%.
Embodiment 13-23
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 130,150 degree of hole injection layer lower 30 minutes dry.
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 the Ir (pq) for being 5% with weight ratio2Acac 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
Comparative example prepares the method for device as the preparation method of embodiment 13-23, in addition to replacing the present inventionization with CBP Close object as material of main part outside.Prepared device (structural schematic diagram is shown in Fig. 1) Photo Research PR650 spectrometer Measure in 10000cd/m2Brightness under external quantum efficiency be such as table 2.
2 test result of table
Embodiment Compound External quantum efficiency Luminescent color
13 3 15 Feux rouges
14 10 16 Feux rouges
15 17 15 Feux rouges
16 19 16 Feux rouges
17 26 17 Feux rouges
18 29 18 Feux rouges
19 36 19 Feux rouges
20 37 18 Feux rouges
21 44 20 Feux rouges
22 45 18 Feux rouges
23 53 16 Feux rouges
Comparative example 1 CBP 12 Feux rouges
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 indoles of the invention containing naphtho- are sent out for organic electroluminescence Optical device can reduce operating voltage, improve device efficiency, be the phosphorescent light body material with excellent performance.As described above, this The compound of 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 indoles containing naphtho-, 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；
Ar1-Ar2Virtue independently selected from hydrogen, deuterium, halogen, cyano, the alkyl of C1-C12, substitution or unsubstituted C6-C30 The heteroaryl of base, substitution or unsubstituted C3-C30；
R1-R8Independently selected from hydrogen, deuterium, halogen, cyano, C1-C12 alkyl.
2. the organic electroluminescent compounds of the indoles containing naphtho- as described in claim 1, which is characterized in that the Ar1-Ar2Solely On the spot selected from phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, fluorenyl, 9,9- dimethyl fluorene Base, 9,9- diphenyl fluorenyl, 9,9- spiral shell, two fluorenyl, dibenzothiophene, dibenzofuran group, carbazyl, pyridyl group, pyrimidine Base, pyridazinyl, triazine radical, imidazole radicals, oxazolyl, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoline Quinoline base, azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals.
3. the organic electroluminescent compounds of the indoles containing naphtho- as described in claim 1, which is characterized in that the R1-R8It is independent Ground is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl.
4. the organic electroluminescent compounds of the indoles containing naphtho- as described in claim 1, which is characterized in that be following structural The compound of 1-56:
5. organic electroluminescent compounds the answering in organic electroluminescence device of the indoles described in claim 1 containing naphtho- 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 indoles containing naphtho- as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that indoles containing naphtho- described in claim 1 Organic electroluminescent compounds where layer be luminescent layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that indoles containing naphtho- described in claim 1 Organic electroluminescent compounds be used alone, or be 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 indoles containing naphtho- of structural formula 1-56 described in 4, or simultaneously using two or more selected from as weighed Benefit require 4 described in structural formula 1-56 the indoles containing naphtho- organic electroluminescent compounds.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201910059460.4A 2019-01-22 2019-01-22 A kind of organic electroluminescent compounds of the indoles containing naphtho- and application thereof and luminescent device Pending CN109651230A (en)

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