CN108865115A - A kind of photoelectric material preparation method of acid imide containing graphene and its derivative - Google Patents
A kind of photoelectric material preparation method of acid imide containing graphene and its derivative Download PDFInfo
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Abstract
The invention discloses the photoelectric material preparation methods of a kind of acid imide containing graphene and its derivative.Include the following steps：A. acid imide or derivatives thereof is blended with graphene, said mixture heating for dissolving is formed into solution W in high boiling solvent；B. under inert gas shielding and under heating, solution W is filtered while hot, filtrate is kept in dark place；C. it is added additive into filtrate, the holding time≤for 24 hours；D., filtrate is distilled to removal solvent under vacuum conditions, obtains mixture of the acid imide or derivatives thereof with graphene.By the way that graphene and additive are added in acid imide or derivatives thereof, after obtained intermingling material film forming, relatively before the acid imide film forming for being not added with graphene and additive after obtained electron mobility be obviously improved.
Description
Technical field
The invention belongs to optoelectronic materials technologies.More particularly, to a kind of acid imide containing graphene and its
The photoelectric material preparation method of derivative.
Background technique
In recent years, imide derivative attracts attention in the application aspect of organic photoelectric functional material, widely
Applied to fields such as organic photovoltaic cell, optical conductor, electroluminescent, self assembly and biological fluorescent labelings.This aspect be due to
Acid imide material has good light, heat and resistance to weather, corrosion resistance, chemical inertness, optical absorption characteristics and higher
Fluorescence quantum yield the features such as；It on the other hand is that there is big total phenyl ring planar structure and two imines ring structures due to it,
It is a kind of typical n-type material with high electron affinity and very strong electronic capability.Additionally can at " bay " and
Amide position is modified its dissolubility, photoelectric property.At present, the progress both at home and abroad about acid imide material is equal
It has been reported that, imide derivative has very big as a kind of performance n-type material outstanding in fields such as organic photovoltaic cells
Potentiality, with going deep into for research, the application of field of photovoltaic materials will be more and more.
Acid imide is as the major defect of n-type material, and compared with PCBM, electron mobility is lower.Such as PCBM
Electron mobility can generally reach 10-3~10-2cm2V-1s-1, and the electron mobility of acid imide or derivatives thereof is only capable of reaching
10-8~10-5cm2V-1s-1.Therefore, need to overcome acid imide and its not high defect of derivative electron mobility.
Summary of the invention
The present invention is directed to overcome above-mentioned the deficiencies in the prior art, graphene is added to shape in acid imide or derivatives thereof
At blend, electron mobility is obviously improved after this blend film forming.
Specifically, above-mentioned purpose of the present invention is achieved through the following technical solutions：
The photoelectric material preparation method of a kind of acid imide containing graphene and its derivative, includes the following steps：
A. acid imide or derivatives thereof is blended with graphene, said mixture is dissolved by heating in high boiling solvent
Form solution W；
B. under inert gas shielding and under heating, solution W is filtered while hot, filtrate is kept in dark place；
C. it is added additive into filtrate, the holding time≤for 24 hours；
D., filtrate is distilled to removal solvent under vacuum conditions, obtains mixing of the acid imide or derivatives thereof with graphene
Object；
Wherein, the molecular structural formula of acid imide and its derivative is：
Wherein, R1、R2For C1-C22 alkyl perhaps the alkoxy alkyl of C1-C22 or alkoxy be straight chain, branch
Chain or ring-type, wherein one or more carbon atoms can be by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxylics
Base, ester group, cyano, nitro replace, and hydrogen atom can be by halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl
Base, carboxyl, ester group, cyano or nitro replace；
X1-X4For hydrogen atom, halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group,
Cyano or nitro；
Wherein, the mass ratio of the acid imide and graphene is 1：(0.01-0.1)；The additive is diiodo-octane
Or chloronaphthalene；Accounting of the additive in solution W filtrate is 0.1-1wt%.
Further, the photoelectric material preparation method of a kind of acid imide containing graphene and its derivative, the height
Boiling point solvent and donor material mass ratio are 10：1~100：1.
Further, the photoelectric material preparation method of a kind of acid imide containing graphene and its derivative, wherein institute
The molecular structural formula for stating acid imide and its derivative is
Wherein, R1、R2For C1-C22 alkyl perhaps the alkoxy alkyl of C1-C22 or alkoxy be straight chain, branch
Chain or ring-type, wherein one or more carbon atoms can be by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxylics
Base, ester group, cyano, nitro replace, and hydrogen atom can be by halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl
Base, carboxyl, ester group, cyano or nitro replace；
X1-X4For halogen atom.
The advantage of the invention is that：
Graphene has good photoelectric properties and electron mobility, itself and acid imide or derivatives thereof are carried out physics
It is blended, additive is added, uniform structure can be formed.Blend solution film forming can effectively be promoted into electricity as n-type material
Transport factor.
Detailed description of the invention
Fig. 1 is blend film (imide derivative in embodiment 1：Graphene=1：0.01) Atomic Mechanics microscope
Figure.
Fig. 2 is blend film (imide derivative in embodiment 2：Graphene=1：0.05) Atomic Mechanics microscope
Figure.
Fig. 3 is blend film (imide derivative in embodiment 3：Graphene=1：0.1) Atomic Mechanics microscope figure.
Fig. 4 is blend film (imide derivative in embodiment 4：Graphene=1：0.1) Atomic Mechanics microscope figure.
Fig. 5 is the structure of imide derivative in embodiment 1 and embodiment 5.
Fig. 6 is the structure of imide derivative in embodiment 2 and embodiment 5.
Fig. 7 is the structure of imide derivative in embodiment 3 and embodiment 5.
Fig. 8 is the structure of imide derivative in embodiment 4.
Fig. 9 is the structure of imide derivative in embodiment 5.
Figure 10 is the structure of imide derivative in embodiment 5.
Figure 11 is the structure of imide derivative in embodiment 5.
Figure 12 is the structure of imide derivative in embodiment 5.
Specific embodiment
The present invention is further illustrated below in conjunction with Figure of description and specific embodiment, but embodiment is not to the present invention
It limits in any form.Unless stated otherwise, the present invention uses reagent, method and apparatus routinely try for the art
Agent, method and apparatus.
Unless stated otherwise, following embodiment agents useful for same and material are commercially available.
Embodiment 1
Imide derivative and graphene are mixed to form blend, and mass ratio is imide derivative：Graphene=
1：0.01, blends described above is dissolved in chlorobenzene and is heated to 100 DEG C, formation solution W；Under protection of argon gas, solution W is kept
Temperature is 100 DEG C, is filtered while hot with the filter that aperture is 0.45 micron, filtrate is stored in brown reagent bottle, is then added
Diiodo-octane saves 3h.Filtrate is finally distilled to removal solvent under vacuum conditions, obtains imide derivative and graphene
Mixture.
When electron mobility to be tested, first said mixture is again dissolved in 100 DEG C of chlorobenzenes, and spin coating is at blend film,
With a thickness of 40nm.The hole mobility of intermingling material is measured using the method for space charge limited current (SCLC).SCLC device
Structure is ITO/PEDOT/ blend film/MoO3/Al.According to formula：JSCLC=(9/8) εoεrμo(V2/L3), it is calculated, J is
Electric current, μoIt is the mobility under zero strength, εoIt is permittivity of vacuum, εrIt is the dielectric constant of material, L is the thickness of material, V
It is the effective voltage of polymeric layer, by the application voltage (V of deviceappl) subtract the built in field voltage (V of devicebi) and device its
Voltage drop (the V of its layer resistances)：V=Vappl-Vbi-Vs.The mobility of device can pass through J1/2The slope of curve of-V calculates
It arrives.Blend film has been done electron mobility test by us, as a comparison, also tested a series of orthogonal tests.Acquired results are such as
Under.
Wherein the structure of imide derivative is as shown in Figure 5.
Embodiment 2
Imide derivative and graphene are mixed to form blend, and mass ratio is imide derivative：Graphene=
1：0.05, blends described above is dissolved in toluene and is heated to 120 DEG C, formation solution W；Under protection of argon gas, solution W is kept
Temperature is 120 DEG C, is filtered while hot with the filter that aperture is 0.7 micron, filtrate is stored in brown reagent bottle, is then added two
Iodo-octane saves 5h.Filtrate is finally distilled to removal solvent under vacuum conditions, obtains imide derivative and graphene
Mixture.
When electron mobility to be tested, first said mixture is again dissolved in 120 DEG C of toluene, and spin coating is at blend film,
With a thickness of 40nm.The hole mobility of intermingling material is measured using the method for space charge limited current (SCLC).SCLC device
Structure is ITO/PEDOT/ blend film/MoO3/Al.According to formula：JSCLC=(9/8) εoεrμo(V2/L3), it is calculated, J is
Electric current, μoIt is the mobility under zero strength, εoIt is permittivity of vacuum, εrIt is the dielectric constant of material, L is the thickness of material, V
It is the effective voltage of polymeric layer, by the application voltage (V of deviceappl) subtract the built in field voltage (V of devicebi) and device its
Voltage drop (the V of its layer resistances)：V=Vappl-Vbi-Vs.The mobility of device can pass through J1/2The slope of curve of-V calculates
It arrives.Blend film has been done electron mobility test by us, as a comparison, also tested a series of orthogonal tests.Acquired results are such as
Under.
Wherein the structure of imide derivative is as shown in Figure 6.
Embodiment 3
Imide derivative and graphene are mixed to form blend, and mass ratio is imide derivative：Graphene=
1：0.1, blends described above is dissolved in trimethylbenzene and is heated to 140 DEG C, formation solution W；Under protection of argon gas, solution is kept
W temperature is 140 DEG C, is filtered while hot with the filter that aperture is 1 micron, filtrate is stored in brown reagent bottle, chlorine is then added
Naphthalene saves 5h.Filtrate is finally distilled to removal solvent under vacuum conditions, obtains the mixing of imide derivative and graphene
Object.
When electron mobility to be tested, first said mixture is again dissolved in 140 DEG C of trimethylbenzenes, and spin coating is at blending
Film, with a thickness of 40nm.The hole mobility of intermingling material is measured using the method for space charge limited current (SCLC).SCLC device
Part structure is ITO/PEDOT/ blend film/MoO3/Al.According to formula：JSCLC=(9/8) εoεrμo(V2/L3), it is calculated, J
It is electric current, μoIt is the mobility under zero strength, εoIt is permittivity of vacuum, εrIt is the dielectric constant of material, L is the thickness of material,
V is the effective voltage of polymeric layer, by the application voltage (V of deviceappl) subtract the built in field voltage (V of devicebi) and device
Voltage drop (the V of other layers of resistances)：V=Vappl-Vbi-Vs.The mobility of device can pass through J1/2The slope of curve of-V calculates
It arrives.Blend film has been done electron mobility test by us, as a comparison, also tested a series of orthogonal tests.Acquired results are such as
Under.
Wherein the structure of imide derivative is as shown in Figure 7.
Embodiment 4
Imide derivative and graphene are mixed to form blend, and mass ratio is imide derivative：Graphene=
1：0.1, blends described above is dissolved in dimethylbenzene and is heated to 140 DEG C, formation solution W；Under protection of argon gas, solution is kept
W temperature is 140 DEG C, is filtered while hot with the filter that aperture is 1 micron, filtrate is stored in brown reagent bottle, chlorine is then added
Naphthalene saves 5h.Filtrate is finally distilled to removal solvent under vacuum conditions, obtains the mixing of imide derivative and graphene
Object.
When electron mobility to be tested, first said mixture is again dissolved in 140 DEG C of dimethylbenzene, and spin coating is at blending
Film, with a thickness of 40nm.The hole mobility of intermingling material is measured using the method for space charge limited current (SCLC).SCLC device
Part structure is ITO/PEDOT/ blend film/MoO3/Al.According to formula：JSCLC=(9/8) εoεrμo(V2/L3), it is calculated, J
It is electric current, μoIt is the mobility under zero strength, εoIt is permittivity of vacuum, εrIt is the dielectric constant of material, L is the thickness of material,
V is the effective voltage of polymeric layer, by the application voltage (V of deviceappl) subtract the built in field voltage (V of devicebi) and device
Voltage drop (the V of other layers of resistances)：V=Vappl-Vbi-Vs.The mobility of device can pass through J1/2The slope of curve of-V calculates
It arrives.Blend film has been done electron mobility test by us, as a comparison, also tested a series of orthogonal tests.Acquired results are such as
Under.
Wherein the structure of imide derivative is as shown in Figure 8.
Embodiment 5
Different imide derivatives and graphene are mixed to form blend, and mass ratio is imide derivative：Stone
Black alkene=1：0.05, blends described above is dissolved in dimethylbenzene and is heated to 140 DEG C, formation solution W；Under protection of argon gas,
Keeping solution W temperature is 140 DEG C, is filtered, filtrate is stored in brown reagent bottle, so with the filter that aperture is 1 micron while hot
After be added chloronaphthalene, save 5h.Filtrate is finally distilled to removal solvent under vacuum conditions, obtains imide derivative and graphite
The mixture of alkene.
When electron mobility to be tested, first said mixture is again dissolved in 140 DEG C of dimethylbenzene, and spin coating is at blending
Film, with a thickness of 30nm.The hole mobility of intermingling material is measured using the method for space charge limited current (SCLC).SCLC device
Part structure is ITO/PEDOT/ blend film/MoO3/Al.According to formula：JSCLC=(9/8) εoεrμo(V2/L3), it is calculated, J
It is electric current, μoIt is the mobility under zero strength, εoIt is permittivity of vacuum, εrIt is the dielectric constant of material, L is the thickness of material,
V is the effective voltage of polymeric layer, by the application voltage (V of deviceappl) subtract the built in field voltage (V of devicebi) and device
Voltage drop (the V of other layers of resistances)：V=Vappl-Vbi-Vs.The mobility of device can pass through J1/2The slope of curve of-V calculates
It arrives.Blend film has been done electron mobility test by us, as a comparison, also tested a series of orthogonal tests.Acquired results are such as
Under.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (3)
1. the photoelectric material preparation method of a kind of acid imide containing graphene and its derivative, which is characterized in that including such as
Lower step：
A. acid imide or derivatives thereof is blended with graphene, said mixture is dissolved by heating and is formed in high boiling solvent
Solution W；
B. under inert gas shielding and under heating, solution W is filtered while hot, filtrate is kept in dark place；
C. it is added additive into filtrate, the holding time≤for 24 hours；
D., filtrate is distilled to removal solvent under vacuum conditions, obtains mixture of the acid imide or derivatives thereof with graphene；
Wherein, the molecular structural formula of acid imide and its derivative is：
Wherein, R1、R2For C1-C22 alkyl perhaps the alkoxy alkyl of C1-C22 or alkoxy be straight chain, branch or
Person is cyclic annular, wherein one or more carbon atoms can be by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester
Base, cyano, nitro replace, and hydrogen atom can be by halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxylic
Base, ester group, cyano or nitro replace；
X1-X4For hydrogen atom, halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano
Or nitro；
Wherein, the mass ratio of the acid imide and graphene is 1：0.01-0.1；The additive is diiodo-octane or chloronaphthalene；
Accounting of the additive in solution W filtrate is 0.1-1wt%.
2. the photoelectric material preparation method of a kind of acid imide containing graphene and its derivative according to claim 1,
It is characterized in that, the high boiling solvent is 10 with quality of materials ratio is blended：1~100：1.
3. the photoelectric material preparation method of a kind of acid imide containing graphene and its derivative according to claim 1,
It is characterized in that, the molecular structural formula of the acid imide and its derivative is
Wherein, R1、R2For C1-C22 alkyl perhaps the alkoxy alkyl of C1-C22 or alkoxy be straight chain, branch or
Person is cyclic annular, wherein one or more carbon atoms can be by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester
Base, cyano, nitro replace, and hydrogen atom can be by halogen atom, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxylic
Base, ester group, cyano or nitro replace；
X1-X4For halogen atom.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110240892A (en) * | 2019-07-03 | 2019-09-17 | 桂林理工大学 | A kind of bionic laminar graphene/imide derivative thermally conductive film and preparation method thereof |
| CN110317582A (en) * | 2019-07-03 | 2019-10-11 | 桂林理工大学 | A kind of imide derivative functionalization graphene/carbon nanotube composite heat-conducting film and preparation method thereof |
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