CN105968062B - Compound and its organic electroluminescence device containing 1,2,4- triazine group - Google Patents

Compound and its organic electroluminescence device containing 1,2,4- triazine group Download PDF

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CN105968062B
CN105968062B CN201610590275.4A CN201610590275A CN105968062B CN 105968062 B CN105968062 B CN 105968062B CN 201610590275 A CN201610590275 A CN 201610590275A CN 105968062 B CN105968062 B CN 105968062B
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compound
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electroluminescence device
organic electroluminescence
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CN105968062A (en
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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

Contain 1 such as structural formula I the present invention provides a kind of, 2, the organic electroluminescent compounds of 4- triazine group, the compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer is comprising one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.

Description

Compound and its organic electroluminescence device containing 1,2,4- triazine group
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind contains the Organic Electricity of 1,2,4- triazine groups Electro luminescent compounds and its organic electroluminescence device belong to organic electroluminescence device field of display technology.
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.
Speed in OLED material, due to the speed of most electroluminescent organic material transporting holes than transmitting electronics Fastly, it be easy to cause the electrons and holes quantity of luminescent layer uneven, the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines) Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines, Simultaneously as lower electron mobility, so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, above it is restricted in application.Cause This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility With great value.
Summary of the invention
Present invention firstly provides the organic electroluminescent compounds that one kind contains 1,2,4- triazine groups, for as follows The compound of structural formula I:
Wherein, Ar1The substitution of substitution or unsubstituted aryl, C3-C30 selected from C6-C30 or it is unsubstituted containing One or more heteroatomic aryl, two aromatic aminos, triaromatic amine base, carbazyl；
A is empty or singly-bound；
L is selected from benzene, biphenyl, naphthalene.
Preferably, Ar1Selected from phenyl, naphthalene, xenyl, phenanthryl, anthryl, aryl anthryl, pyrenyl, dibenzofuran group, Dibenzothiophene, benzimidazolyl, pyridyl group, pyrimidine radicals, quinolyl, isoquinolyl, triazine radical, pyrrole radicals, furyl, thiophene Oxazolyl, quinazolyl, triazol radical, benzothiazole, diazosulfide, 1,2,4- triazolyl, triphenylamine base, aryl carbazole base, Carbazyl, hexichol amido or the above group are further replaced the alkyl of C1-C10 or alkoxy.
It is further preferred that the compound for containing 1,2,4- triazine groups of the invention is the chemical combination of following structural 1-54 Object:
Organic electroluminescent compounds containing 1,2,4- triazine group of the invention can be applied in organic electroluminescent Device, organic solar batteries, 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, wherein at least one layer compound for containing 1,2,4- triazine groups contained as described in structural formula I in the organic layer:
Wherein A, L, Ar1It is defined as described above.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking Layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer.
Preferably, wherein the layer where the compound for containing 1,2,4- triazine groups as described in structural formula I is that electronics passes Defeated layer or electron injecting layer；
Preferably, the compound that 1,2,4- triazine groups are wherein contained described in structural formula I is the chemical combination of structural formula 1-54 Object；
It, can be independent when the compound for containing 1,2,4- triazine groups as described in structural formula I is prepared for luminescent device It uses, can also be used in mixed way with other compounds；Can individually it make as described in structural formula I containing 1,2,4- triazine group It, can also be simultaneously using the two or more compounds in structural formula I with one such compound.
Organic electroluminescence device of the invention, further preferred mode are that the organic electroluminescence device includes sun Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein luminescent layer, electron transfer layer or electronics Compound containing structural formula I in implanted layer；It is further preferred that containing in luminescent layer, electron transfer layer or electron injecting layer Compound be structural formula 1-54 compound.
In organic electroluminescence device of the invention, it can also be also served as when the compound of structural formula I is as electron transfer layer Electron injecting layer.
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 hole blocking layer It is medium, 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 may include that other small molecules and macromolecule are organic Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 8'-, 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 be contained, including but not limited to Naphthalene compounds, compound of fluorene class, luxuriant and rich with fragrance class compound, bend class compound, glimmering anthracene compound, anthracene class chemical combination at pyrene compound Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent network Object (such as Ir, Pt, Os, Cu, Au), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic polymer luminescent material are closed, They can be used alone, and can also be used with a variety of mixtures.
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 the following compound of collocation, but not limited to this: oxa- oxazole, thiazole compound, three nitrogen Azole compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, contain sila at three nitrogen piperazine class compounds Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine replace Benzene-like compounds, 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, except it is of the invention there is Compounds of structural formula I in addition to, be mainly selected from the compound of alkali metal or alkali metal, or be selected from alkaline earth The compound or alkali metal complex of metal or alkaline-earth metal, can choose following compound, but not limited to this: alkali gold Category, alkaline-earth metal, rare earth metal, the oxide of alkali metal or halide, the oxide of alkaline-earth metal or halide, rare earth The organic complex of the oxide or halide of metal, alkali metal or alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, Magnesia, these compounds, which can be used alone, to be used with mixture, can also match with other electroluminescent organic materials It closes and uses.
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.
It is preferable that device experimental shows that the compound that contains 1,2,4- triazine groups of the present invention as described in structural formula I has Thermal stability, high-luminous-efficiency, high luminance purity.Device using organic electroluminescent compounds production has electroluminescent The advantage that efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is the mass spectrogram of compound 12；
Fig. 2 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 transmission layer, and 140 are represented as sending out Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as cathode；
Fig. 3 is another organic electroluminescence device structural schematic diagram of the present invention；
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transports 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 electron injecting 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.
The synthesis of intermediate
The synthesis of intermediate A
In the single-necked flask of 250ml be added 21g benzil (100mmol), 21g to Bromophenacyl phenylhydrazine (100mmol), 15g ammonium acetate (20mmol) and 200ml glacial acetic acid are heated to 120 DEG C, flow back 6 hours.It being cooled to room temperature, revolving removes solvent, With ethyl alcohol recrystallization, faint yellow solid 26.3, yield 68% are obtained after dry.
The synthesis of intermediate B
Synthetic method is as the synthesis of intermediate A, other than replacing to Bromophenacyl phenylhydrazine with a Bromophenacyl phenylhydrazine, Yield 55%.
The synthesis of intermediate C
Synthetic method is as with intermediate A, other than replacing benzil with phenanthrenequione, yield 81%.
Embodiment 1
The synthesis of compound 5
In three-necked flask, intermediate A (1.9g, 5mmol), 9- benzene -10- anthracene boric acid (1.5g, 5mmol), carbonic acid is added Potassium (1.38g, 10mmol), tetra-triphenylphosphine palladium (50mg), tetrahydrofuran (20ml) and water (10ml), are heated under nitrogen protection Reflux 10 hours, it is cooling, it is extracted with dichloromethane, organic layer is dry, and concentration, crude product obtains product through column chromatographic purifying 2.1g, yield 75%.
Embodiment 2
The synthesis of compound 12
Synthetic method is as compound 5, in addition to B- [4- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) phenyl]-boric acid Outside instead of 9- benzene -10- anthracene boric acid, yield 64%.Its nuclear-magnetism is as shown in Figure 1.
Embodiment 3
The synthesis of compound 20
Synthetic method is as compound 5, other than replacing 9- benzene -10- anthracene boric acid with 4- (9H- carbazyl)-phenyl boric acid, Yield 81%.
Embodiment 4
The synthesis of compound 25
Synthetic method is as compound 5, in addition to 2,4- diphenyl -6- ((3- pinacol borate) benzene) -1,3,5- Triazine replaces outside 9- benzene -10- anthracene boric acid, yield 66%.
Embodiment 5
The synthesis of compound 38
Synthetic method is as compound 12, other than replacing intermediate A with intermediate C, yield 72%.
Embodiment 6
The synthesis of compound 45
Synthetic method is as compound 20, other than replacing intermediate A with intermediate C, yield 77%.
Embodiment 7-10
The preparation of organic electroluminescence device
OLED is prepared using the compound in the embodiment of the present invention.
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, NPB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq for crossing 37.5nm thickness is steamed on the hole transport layer31%C545T is adulterated as luminescent layer 140.
Then, the compound 1 and Liq for 37.5nm thickness being deposited on the light-emitting layer are as electron transfer layer 150,1 He of compound The ratio of Liq is 1:1.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is shown in Fig. 2) is measured with Photo Research PR650 spectrometer in 20mA/ cm2Current density under efficiency it is as shown in table 1.
Comparative example 1
In addition to electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 7.
Prepared device (structural schematic diagram is shown in Fig. 2) with Photo Research PR650 spectrometer measure 20mA/cm2Current density under efficiency it is as shown in table 1.
Table 1
Embodiment Compound Power efficiency (lm/W) Color
7 5 6.0 Green light
8 12 6.2 Green light
9 25 6.3 Green light
10 38 6.1 Green light
Comparative example 1 Alq3 5.0 Green light
From table 1 it follows that at identical conditions, using organic electroluminescent electron transport material system of the invention The efficiency of standby organic electroluminescence device is higher than comparative example, as described above, the compound of the present invention has high stability, this The organic electroluminescence device of invention preparation has high efficiency and optical purity.
Structural formula described in device is as follows:
Embodiment 11-12
The preparation of organic electroluminescence device
OLED is prepared using the compound in the embodiment of the present invention.
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 50nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the NPB that 25nm thickness is deposited on hole injection layer is hole transmission layer 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 8nm thickness.
Then, the luminescent layer 160 for crossing 20nm thickness is steamed on electronic barrier layer, wherein shine based on the compounds of this invention Material, and with the Ir of 10% weight ratio (ppy)2Acac adulterates guest materials as phosphorescence.
Then, the TPBi 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. 3) is measured with Photo Research PR650 spectrometer in 20mA/ cm2Current density under efficiency it is as shown in table 2.
Comparative example 2
The device of comparative example preparation is as embodiment 11-12 part preparation method, in addition to replacing the compounds of this invention with CBP Outside as material of main part.
Table 2
From Table 2, it can be seen that under identical current density condition, using the Organic Electricity of the compound of the present invention preparation The efficiency of electroluminescence device is all higher than comparative example, as described above, the compound of the present invention have high stability, preparation it is organic Electroluminescent device has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that the ordinary skill of this field is without wound The property made labour, which according to the present invention can conceive, makes many modifications and variations.Therefore, all technician in the art Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Scheme, all should be within the scope of protection determined by the claims.

Claims (8)

1. the organic electroluminescent compounds that one kind contains 1,2,4- triazine groups, it is characterised in that it is to have the following structure formula The compound of I:
Wherein, Ar1Selected from phenyl, naphthalene, xenyl, phenanthryl, anthryl, aryl anthryl, pyrenyl, dibenzofuran group, dibenzo thiophene Pheno base, benzimidazolyl, pyridyl group, pyrimidine radicals, quinolyl, isoquinolyl, triazine radical, pyrrole radicals, furyl, thiazolyl, quinoline Oxazoline base, triazol radical, benzothiazolyl, diazosulfide base, 1,2,4- triazolyl, aryl carbazole base, carbazyl, diphenylamines Base or the above group are further replaced the alkyl of C1-C10 or alkoxy；
A is empty or singly-bound；
L is selected from benzene, biphenyl, naphthalene；
And it excludes structural formula and isCompound.
2. the organic electroluminescent compounds according to claim 1 containing 1,2,4- triazine group, it is characterised in that its For the compound of following structural 2-54:
3. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection Layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, it is characterised in that in organic layer At least one layer includes the compound as described in claim 1 containing 1,2,4- triazine group.
4. organic electroluminescence device according to claim 3, it is characterised in that contain 1,2,4- as described in structural formula I Layer where the compound of triazine group is electron transfer layer or electron injecting layer.
5. organic electroluminescence device according to claim 3, it is characterised in that contain 1,2,4- as described in structural formula I The compound of triazine group is used alone, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 3, it is characterised in that contain 1,2,4- as described in structural formula I One such compound is used alone in the compound of triazine group, or uses two or more in structural formula I simultaneously Compound.
7. organic electroluminescence device according to claim 3, it includes anode, hole transmission layer, luminescent layer, electronics to pass Defeated layer, electron injecting layer and cathode, it is characterised in that the chemical combination containing structural formula I in electron transfer layer and/or electron injecting layer Object.
8. organic electroluminescence device according to claim 3, it includes anode, hole transmission layer, luminescent layer, electronics to pass Defeated layer, electron injecting layer and cathode, it is characterised in that the compound contained in electron transfer layer and/or electron injecting layer is structure The compound of formula 2-54.
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