CN107266436A - A kind of organic photoelectrical material and its preparation method and application - Google Patents
A kind of organic photoelectrical material and its preparation method and application Download PDFInfo
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Abstract
The present invention provides a kind of organic photoelectrical material and its preparation method and application, is related to organic optoelectronic materials technology.By introducing rigid fluorenes class formation, the glass transition temperature of compound is increased；Imidazopyridine structure is introduced, the driving voltage of organic electroluminescence device is reduced.Used as the hole mobile material in organic electroluminescence device, show luminous efficiency height, the advantage of long lifespan.The present invention also provides a kind of preparation method of organic photoelectrical material, and the preparation method is simple, raw material is easy to get.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of organic photoelectrical material of aromatic amine and its
Preparation method and application.
Background technology
Organic electroluminescence device (OLED) is a kind of new flat panel display device, with energy-conservation, fast response time, face
Colour-stable, environmental suitability is strong, radiationless, long lifespan, light weight, thickness of thin the features such as.
The principle of organic electroluminescent can simply be divided into 3 steps to illustrate, first, in the effect of applying bias
Under, hole and electronics are overcome after the obstacle at interface, are injected by anode and negative electrode, the hole mobile material (HTL) into device
HOMO can rank and electron transport material (ETL) LUMO can rank, then electric charge transmitted under extraneous electric field driven and reach luminous
Layer, last electronics and hole are combined in luminescent layer organic substance, form exciton (exciton).Exciton is not one
Stable state, is given off energy in the form of light or heat and returns to stable ground state, therefore be an electricity for entirety afterwards
Flow the luminous phenomenon of driving.
According to the size of electroluminescent organic material molecular weight, small molecule electroluminescent organic material and high score can be divided into
Sub- electroluminescent organic material.In presently disclosed luminescent material, due to the fluorescence quantum efficiency of small molecule electroluminescent material
Height, is easily purified, luminosity and excitation also superior to high polymer material, so, small molecule electroluminescent materials application is in hair
Optical device is commercialized with starting to realize.
With developing rapidly for photoelectric communication in recent years and MultiMedia Field, organic photoelectrical material has turned into modern society to be believed
The core of breath and electronic industry.But, OLED will move towards practical, it is necessary to which solution reduces cost, improves luminous efficiency, extension hair
The problems such as light life-span.
The content of the invention
It is an object of the invention to provide a kind of organic photoelectrical material and its preparation method and application, it is organic that the present invention is provided
Compound thermal stability is high, preparation method is simple, and the organic luminescent device being made up of the compound shows luminous efficiency
Height, the advantage of long lifespan is the luminous organic material of function admirable.
Present invention firstly provides a kind of organic photoelectrical material, the concrete structure formula of the material is as shown in formula I：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6
~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~
One kind in C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1
One kind in~C10 alkyl, C6~C10 substituted or unsubstituted aryl.
It is preferred that, the R2Substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles selected from C6~C18,
Substituted or unsubstituted hexa-member heterocycle, C10~C24 substituted or unsubstituted condensed ring, C8~C26 it is substituted or unsubstituted thick
One kind in heterocycle.
It is preferred that, the R1Selected from methyl, ethyl, phenyl or xenyl；R2Selected from phenyl, naphthyl, anthryl, phenanthryl, pyrene
Base, xenyl, terphenyl, indenyl, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, imidazole radicals, thiazole
Ji, oxazolyls, fluorenylidene or the fluorenyl of spiral shell two；R3Selected from hydrogen atom, methyl, ethyl, the tert-butyl group or phenyl.
It is preferred that, any one of the organic photoelectrical material in structure shown in following TM1~TM87：
The present invention also provides a kind of preparation method of organic photoelectrical material, and syntheti c route is as follows：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6
~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~
One kind in C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1
One kind in~C10 alkyl, C6~C10 substituted or unsubstituted aryl.
The present invention also provides application of the organic photoelectrical material of aromatic amine in organic electroluminescence device.
It is preferred that, the organic electroluminescence device includes containing in anode, negative electrode and organic matter layer, the organic matter layer
Described organic photoelectrical material.
It is preferred that, the organic photoelectrical material is used for the hole transmission layer for preparing organic electroluminescence device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of organic photoelectrical material of aromatic amine, the organic photoelectrical material has knot shown in formula I
Structure, by introducing rigid fluorenes class formation, increases the glass transition temperature of compound；Imidazopyridine structure is introduced, is reduced organic
The driving voltage of electroluminescent device.Used as the hole mobile material in organic electroluminescence device, performance is set out
Light efficiency is high, the advantage of long lifespan, better than existing conventional OLED.The present invention also provides a kind of organic photoelectric of aromatic amine
The preparation method of material, the preparation method is simple, raw material is easy to get, the need for disclosure satisfy that industrialization development.The present invention's is organic
Photoelectric material has good application effect in OLED luminescent devices, with good industrialization prospect.
Embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model that the present invention is protected
Enclose.
Present invention firstly provides a kind of organic photoelectrical material, structural formula is：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6
~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~
One kind in C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1
One kind in~C10 alkyl, C6~C10 substituted or unsubstituted aryl.
Preferably R2Substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution selected from C6~C18 or
In unsubstituted hexa-member heterocycle, C10~C24 substituted or unsubstituted condensed ring, C8~C26 substituted or unsubstituted condensed hetero ring
One kind.
Further preferably R1Selected from methyl, ethyl, phenyl or xenyl；R2Selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl
Base, terphenyl, indenyl, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, imidazole radicals, thiazolyl, oxazoles
Base, fluorenylidene or the fluorenyl of spiral shell two；R3Selected from hydrogen atom, methyl, ethyl, the tert-butyl group or phenyl.
According to the present invention, described substituted aryl, the five-ring heterocycles of substitution, the hexa-member heterocycle of substitution, the condensed ring of substitution,
In substituted condensed hetero ring, substituent independence be selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Specifically, the organic photoelectrical material is preferably selected from any one in structure shown in following TM1~TM87：
The present invention also provides a kind of preparation method of organic photoelectrical material, and syntheti c route is as follows：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6
~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~
One kind in C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1
One kind in~C10 alkyl, C6~C10 substituted or unsubstituted aryl.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Under nitrogen protection, triphenylphosphine palladium is catalyst, in the case that potassium carbonate is alkali, bromo-derivative and primary amino-compound
Intermediate A is obtained via Buchwald-Hartwig coupling reactions.
According to the present invention, the compound shown in target product is prepared according to method as follows：
Under nitrogen protection, triphenylphosphine palladium is catalyst, in the case that potassium carbonate is alkali, intermediate A and imidazo pyrrole
Pyridine class compound obtains target product via Buchwald-Hartwig coupling reactions.
According to the present invention, compound and synthesis target product shown in synthetic intermediate A are to pass through under nitrogen protection
Coupling reaction is obtained, and the present invention does not have special limitation to the coupling reaction, using idol well-known to those skilled in the art
Connection reaction, the preparation method is simple, and raw material is easy to get.
The present invention also provides application of the organic photoelectrical material in organic electroluminescence device, organic light of the invention
Electric material can be applied as hole mobile material in terms of organic electroluminescence device, the organic electroluminescence device
Including anode, negative electrode and organic matter layer, organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer,
At least one layer in hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic matter layer contains above-mentioned
Described organic photoelectrical material.The organic photoelectrical material can specifically be used as the hole transport for preparing organic electroluminescence device
Layer.The device architecture of use is preferably specially：BH1 and BD1 is used as luminescent layer material, and Alq3 is used as electron-transporting material, described
Organic photoelectrical material be used as hole transmission layer material, the organic luminescent device to manufacture construction same as below：ITO/ institutes
Organic photoelectrical material/the BH1 stated:BD1/Alq3/LiF/Al.The organic electroluminescence device can be used for flat-panel monitor, shine
The application fields such as Mingguang City source, direction board, signal lamp.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this
Preparation method known to art personnel is prepared.
Embodiment A：The synthesis of intermediate A
(A1) preparation of intermediate A 1
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (37.0g, 402mmol) added to aniline (17.3g, 186mmol) and bromo- 9, the 9- dimethyl fluorenes of 2- (49.7g,
183mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed
Compound is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and
And merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, intermediate is recrystallized to give
(88%) 45.8g, yield is to A1.
Mass spectrum m/z：285.19 (calculated values：285.15).Theoretical elemental content (%) C21H19N：C,88.38；H,6.71；
N, 4.91 actual measurement constituent contents (%)：C,88.37；H,6.72；N,4.91.The above results confirm that it is target product to obtain product.
Following midbody compound is obtained in a similar fashion：
Embodiment A2:Mass spectrum m/z：409.19 (calculated values：409.18).Theoretical elemental content (%) C31H23N：C,
90.92；H,5.66；N, 3.42 actual measurement constituent contents (%)：C,90.93；H,5.65；N,3.42.The above results confirm to be produced
Thing is target product.
Embodiment A3:Mass spectrum m/z：407.15 (calculated values：407.17).Theoretical elemental content (%) C31H21N：C,
91.37；H,5.19；N, 3.44 actual measurement constituent contents (%)：C,91.38；H,5.19；N,3.43.The above results confirm to be produced
Thing is target product.
Embodiment A4:Mass spectrum m/z：285.16 (calculated values：285.15).Theoretical elemental content (%) C21H19N：C,
88.38；H,6.71；N, 4.91 actual measurement constituent contents (%)：C,88.37；H,6.72；N,4.91.The above results confirm to be produced
Thing is target product.
Embodiment A5:Mass spectrum m/z：409.15 (calculated values：409.18).Theoretical elemental content (%) C31H23N：C,
90.92；H,5.66；N, 3.42 actual measurement constituent contents (%)：C,90.91；H,5.65；N,3.44.The above results confirm to be produced
Thing is target product.
Embodiment A6:Mass spectrum m/z：407.19 (calculated values：407.18).Theoretical elemental content (%) C31H21N：C,
91.37；H,5.19；N, 3.44 actual measurement constituent contents (%)：C,91.36；H,5.19；N,3.45.The above results confirm to be produced
Thing is target product.
Embodiment A7:Mass spectrum m/z：361.15 (calculated values：361.18).Theoretical elemental content (%) C27H23N：C,
89.71；H,6.41；N, 3.87 actual measurement constituent contents (%)：C,89.72；H,6.42；N,3.86.The above results confirm to be produced
Thing is target product.
Embodiment A8:Mass spectrum m/z：485.22 (calculated values：485.21).Theoretical elemental content (%) C37H27N：C,
91.51；H,5.60；N, 2.88 actual measurement constituent contents (%)：C,91.52；H,5.61；N,2.87.The above results confirm to be produced
Thing is target product.
Embodiment A9:Mass spectrum m/z：483.21 (calculated values：483.20).Theoretical elemental content (%) C37H25N：C,
91.89；H,5.21；N, 2.90 actual measurement constituent contents (%)：C,91.88；H,5.21；N,2.91.The above results confirm to be produced
Thing is target product.
Embodiment A10:Mass spectrum m/z：361.15 (calculated values：361.18).Theoretical elemental content (%) C27H23N：C,
89.71；H,6.41；N, 3.87 actual measurement constituent contents (%)：C,89.71；H,6.42；N,3.87.The above results confirm to be produced
Thing is target product.
Embodiment A11:Mass spectrum m/z：485.20 (calculated values：485.21).Theoretical elemental content (%) C37H27N：C,
91.51；H,5.60；N, 2.88 actual measurement constituent contents (%)：C,91.52；H,5.62；N,2.86.The above results confirm to be produced
Thing is target product.
Embodiment A12:Mass spectrum m/z：483.21 (calculated values：483.20).Theoretical elemental content (%) C37H25N：C,
91.89；H,5.21；N, 2.90 actual measurement constituent contents (%)：C,91.88；H,5.21；N,2.91.The above results confirm to be produced
Thing is target product.
Embodiment A13:Mass spectrum m/z：335.15 (calculated values：335.17).Theoretical elemental content (%) C25H21N：C,
89.51；H,6.31；N, 4.18 actual measurement constituent contents (%)：C,89.51；H,6.32；N,4.17.The above results confirm to be produced
Thing is target product.
Embodiment A14:Mass spectrum m/z：459.21 (calculated values：459.20).Theoretical elemental content (%) C35H25N：C,
91.47；H,5.48；N, 3.05 actual measurement constituent contents (%)：C,91.48；H,5.49；N,3.03.The above results confirm to be produced
Thing is target product.
Embodiment A15:Mass spectrum m/z：457.15 (calculated values：457.18).Theoretical elemental content (%) C35H23N：C,
91.87；H,5.07；N, 3.06 actual measurement constituent contents (%)：C,91.86；H,5.06；N,3.07.The above results confirm to be produced
Thing is target product.
Embodiment A16:Mass spectrum m/z：335.16 (calculated values：335.17).Theoretical elemental content (%) C25H21N：C,
89.51；H,6.31；N, 4.18 actual measurement constituent contents (%)：C,89.52；H,6.32；N,4.16.The above results confirm to be produced
Thing is target product.
Embodiment A17:Mass spectrum m/z：459.20 (calculated values：459.20).Theoretical elemental content (%) C35H25N：C,
91.47；H,5.48；N, 3.05 actual measurement constituent contents (%)：C,91.48；H,5.48；N,3.04.The above results confirm to be produced
Thing is target product.
Embodiment A18:Mass spectrum m/z：457.19 (calculated values：457.18).Theoretical elemental content (%) C35H23N：C,
91.87；H,5.07；N, 3.06 actual measurement constituent contents (%)：C,91.86；H,5.08；N,3.06.The above results confirm to be produced
Thing is target product.
Embodiment A19:Mass spectrum m/z：401.20 (calculated values：401.21).Theoretical elemental content (%) C30H21N：C,
89.73；H,6.78；N, 3.49 actual measurement constituent contents (%)：C,89.72；H,6.79；N,3.49.The above results confirm to be produced
Thing is target product.
Embodiment A20:Mass spectrum m/z：408.15 (calculated values：408.16).Theoretical elemental content (%) C30H20N2：C,
88.21；H,4.93；N, 6.86 actual measurement constituent contents (%)：C,88.21；H,4.92；N,6.87.The above results confirm to be produced
Thing is target product.
Embodiment A21:Mass spectrum m/z：465.24 (calculated values：465.25).Theoretical elemental content (%) C35H31N：C,
90.28；H,6.71；N, 3.01 actual measurement constituent contents (%)：C,90.27；H,6.72；N,3.01.The above results confirm to be produced
Thing is target product.
Embodiment B：The synthesis of target product
(B1) compound TM1 preparation
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (37.0g, 402mmol) is added to the bromo- imidazos of 6- [1,2-a] pyridine (39.4g, 201mmol) and intermediate A 1
The solution of (52.1g, 183mmol) in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.Should
Reactant mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and carried with toluene
Take, and merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give
(80%) 58.7g, yield is to target product TM1.
Mass spectrum m/z：401.16 (calculated values：401.19).Theoretical elemental content (%) C28H23N3：C,83.76；H,5.77；
N, 10.47 actual measurement constituent contents (%)：C,83.77；H,5.76；N,10.46.The above results confirm that it is target product to obtain product.
Following midbody compound is obtained in a similar fashion：
Embodiment B2:Mass spectrum m/z：525.21 (calculated values：525.22).Theoretical elemental content (%) C38H27N3：C,
86.83；H,5.18；N, 7.99 actual measurement constituent contents (%)：C,86.84；H,5.18；N,7.98.The above results confirm to be produced
Thing is target product.
Embodiment B3:Mass spectrum m/z：523.21 (calculated values：523.20).Theoretical elemental content (%) C38H25N3：C,
87.16；H,4.81；N, 8.02 actual measurement constituent contents (%)：C,87.15；H,4.82；N,8.02.The above results confirm to be produced
Thing is target product.
Embodiment B4:Mass spectrum m/z：401.16 (calculated values：401.19).Theoretical elemental content (%) C28H23N3：C,
83.76；H,5.77；N, 10.47 actual measurement constituent contents (%)：C,83.77；H,5.77；N,10.46.The above results confirm to obtain
Product is target product.
Embodiment B5:Mass spectrum m/z：525.20 (calculated values：525.22).Theoretical elemental content (%) C38H27N3：C,
86.83；H,5.18；N, 7.99 actual measurement constituent contents (%)：C,86.82；H,5.19；N,7.99.The above results confirm to be produced
Thing is target product.
Embodiment B6:Mass spectrum m/z：523.20 (calculated values：523.20).Theoretical elemental content (%) C38H25N3：C,
87.16；H,4.81；N, 8.02 actual measurement constituent contents (%)：C,87.15；H,4.81；N,8.04.The above results confirm to be produced
Thing is target product.
Embodiment B7:Mass spectrum m/z：553.26 (calculated values：553.25).Theoretical elemental content (%) C40H31N3：C,
86.77；H,5.64；N, 7.59 actual measurement constituent contents (%)：C,86.78；H,5.64；N,7.58.The above results confirm to be produced
Thing is target product.
Embodiment B8:Mass spectrum m/z：677.27 (calculated values：677.28).Theoretical elemental content (%) C50H35N3：C,
88.60；H,5.20；N, 6.20 actual measurement constituent contents (%)：C,88.60；H,5.20；N,6.20.The above results confirm to be produced
Thing is target product.
Embodiment B9:Mass spectrum m/z：675.25 (calculated values：675.27).Theoretical elemental content (%) C50H33N3：C,
88.86；H,4.92；N, 6.22 actual measurement constituent contents (%)：C,88.85；H,4.92；N,6.23.The above results confirm to be produced
Thing is target product.
Embodiment B10:Mass spectrum m/z:554.27 (calculated values：554.25).Theoretical elemental content (%) C39H30N4：C,
84.45；H,5.45；N, 10.10 actual measurement constituent contents (%)：C,84.44；H,5.45；N,10.11.The above results confirm to obtain
Product is target product.
Embodiment B11:Mass spectrum m/z：678.29 (calculated values：678.28).Theoretical elemental content (%) C49H34N4：C,
86.70；H,5.05；N, 8.25 actual measurement constituent contents (%)：C,86.72；H,5.04；N,8.24.The above results confirm to be produced
Thing is target product.
Embodiment B12:Mass spectrum m/z：676.25 (calculated values：676.26).Theoretical elemental content (%) C49H32N4：C,
86.96；H,4.77；N, 8.28 actual measurement constituent contents (%)：C,86.97；H,4.76；N,8.27.The above results confirm to be produced
Thing is target product.
Embodiment B13:Mass spectrum m/z：451.21 (calculated values：451.20).Theoretical elemental content (%) C32H25N3：C,
85.11；H,5.58；N, 9.31 actual measurement constituent contents (%)：C,85.11；H,5.57；N,9.32.The above results confirm to be produced
Thing is target product.
Embodiment B14:Mass spectrum m/z：575.23 (calculated values：575.24).Theoretical elemental content (%) C42H29N3：C,
87.62；H,5.08；N, 7.30 actual measurement constituent contents (%)：C,87.62；H,5.07；N,7.31.The above results confirm to be produced
Thing is target product.
Embodiment B15:Mass spectrum m/z：649.26 (calculated values：649.25).Theoretical elemental content (%) C48H31N3：C,
88.72；H,4.81；N, 6.47 actual measurement constituent contents (%)：C,88.71；H,4.81；N,6.48.The above results confirm to be produced
Thing is target product.
Embodiment B16:Mass spectrum m/z：527.26 (calculated values：527.24).Theoretical elemental content (%) C38H29N3：C,
86.50；H,5.54；N, 7.96 actual measurement constituent contents (%)：C,86.51；H,5.54；N,7.95.The above results confirm to be produced
Thing is target product.
Embodiment B17:Mass spectrum m/z：652.24 (calculated values：652.26).Theoretical elemental content (%) C47H32N4：C,
86.48；H,4.94；N, 8.58 actual measurement constituent contents (%)：C,86.49；H,4.93；N,8.58.The above results confirm to be produced
Thing is target product.
Embodiment B18:Mass spectrum m/z：457.19 (calculated values：457.18).Theoretical elemental content (%) C43H29N3：C,
87.88；H,4.97；N, 7.15 actual measurement constituent contents (%)：C,87.89；H,4.96；N,7.15.The above results confirm to be produced
Thing is target product.
Embodiment B19:Mass spectrum m/z：517.26 (calculated values：517.25).Theoretical elemental content (%) C37H31N3：C,
85.85；H,6.04；N, 8.12 actual measurement constituent contents (%)：C,85.86；H,6.2；N,8.12.The above results confirm to obtain product
For target product.
Embodiment B20:Mass spectrum m/z：524.22 (calculated values：524.20).Theoretical elemental content (%) C37H24N4：C,
84.71；H,4.61；N, 10.68 actual measurement constituent contents (%)：C,84.71；H,4.62；N,10.67.The above results confirm to obtain
Product is target product.
Embodiment B21:Mass spectrum m/z：581.29 (calculated values：581.28).Theoretical elemental content (%) C42H35N3：C,
86.71；H,6.06；N, 7.22 actual measurement constituent contents (%)：C,86.72；H,6.05；N,7.23.The above results confirm to be produced
Thing is target product.
Contrast Application Example：
By Corning (healthy and free from worry) 15 Ω of society/cm2 (1000) ito substrate successively in acetone, isopropanol is washed in pure water respectively
Net 15 minutes, and expose 30 minutes under ultraviolet light, then handled 10 minutes with plasma.Then by the ito substrate after processing
It is put into evaporated device.One layer of 30nm NPB is deposited first as hole transmission layer, followed by the evaporation of luminescent layer, mixing evaporation
BH1 and 5% BD1, is then deposited 30nm Alq3 as electron transfer layer, 0.5nm LiF is then deposited again, then evaporation
60nm metal Al.
Application Example
By Corning (healthy and free from worry) 15 Ω of society/cm2 (1000) ito substrate successively in acetone, isopropanol is washed in pure water respectively
Net 15 minutes, and expose 30 minutes under ultraviolet light, then handled 10 minutes with plasma.Then by the ito substrate after processing
It is put into evaporated device.The one layer of 30nm compound TM of embodiment B synthesis is deposited first as hole transmission layer, followed by it is luminous
The evaporation of layer, mixing evaporation BH1 and 5% BD1, is then deposited 30nm Alq3 as electron transfer layer, is then deposited again
0.5nm LiF, then evaporation 60nm metal Al.
The electron luminescence characteristic of the organic luminescent device of above method manufacture is represented in the following table：
Result above shows that the organic photoelectrical material of aromatic amine of the invention is applied in organic electroluminescence device,
Especially as hole mobile material, luminous efficiency height, the advantage of long lifespan are shown, is organic light emission material of good performance
Material.
Obviously, the explanation of above example is only intended to the method and its core concept for helping to understand the present invention.It should refer to
Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (8)
1. a kind of organic photoelectrical material, it is characterised in that the concrete structure formula of the material is as shown in formula I：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6~C50
Substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C30
One kind in substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1~C10
Alkyl, one kind in C6~C10 substituted or unsubstituted aryl.
2. a kind of organic photoelectrical material according to claim 1, it is characterised in that R2Substitution selected from C6~C18 does not take
The aryl in generation, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C24 substitution or unsubstituted
Condensed ring, one kind in C8~C26 substituted or unsubstituted condensed hetero ring.
3. a kind of organic photoelectrical material according to claim 1, it is characterised in that R1Selected from methyl, ethyl, phenyl or connection
Phenyl；R2Selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, indenyl, pyrrole radicals, pyridine radicals, thiophene
Base, furyl, indyl, quinolyl, imidazole radicals, thiazolyl, oxazolyls, fluorenylidene or the fluorenyl of spiral shell two；R3Selected from hydrogen atom, first
Base, ethyl, the tert-butyl group or phenyl.
4. a kind of organic photoelectrical material according to claim 1, it is characterised in that the organic photoelectrical material is selected from as follows
Any one in structure shown in TM1~TM87：
5. the preparation method of the organic photoelectrical material described in claim any one of 1-4, it is characterised in that closed by following route
Into obtaining the organic photoelectrical material：
Wherein, R1One kind in the substituted or unsubstituted aryl of alkyl, C6~C10 selected from C1~C10；R2Selected from C6~C50
Substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C30
One kind in substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring；R3Selected from hydrogen atom, C1~C10
Alkyl, one kind in C6~C10 substituted or unsubstituted aryl.
6. first electrode, second electrode and the one or more organic matter layer organic electroluminescences being placed between two electrode
Part, at least one described organic matter layer includes the organic photoelectrical material described in the Claims 1 to 4.
7. application of the organic photoelectrical material according to claim 6 in organic electroluminescence device, it is characterised in that institute
Organic electroluminescence device is stated including anode, negative electrode and organic matter layer, it is any containing Claims 1 to 4 in the organic matter layer
Organic photoelectrical material described in.
8. application of the organic photoelectrical material according to claim 7 in organic electroluminescence device, it is characterised in that institute
Stating organic layer includes containing the organic photoelectrical material described in any one of Claims 1 to 4 in hole transmission layer, hole transmission layer.
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