CN108264632A - A kind of photoelectric material of sulfur-bearing and preparation method thereof - Google Patents
A kind of photoelectric material of sulfur-bearing and preparation method thereof Download PDFInfo
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- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C08G2261/10—Definition of the polymer structure
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- C08G2261/10—Definition of the polymer structure
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/95—Use in organic luminescent diodes
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- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
Abstract
The present invention relates to technical field of photoelectric material preparation, and in particular to a kind of photoelectric material of sulfur-bearing and preparation method thereof；Contain thiphene ring in its structure of organic photoelectrical material prepared by the present invention, since thiphene ring is five-membered ring structure, meet shock youngster's rule, with moderate band gap, wider spectral response, preferable thermal stability and environmental stability, organic photoelectrical material photoelectric property is excellent, conversion ratio is efficient, low manufacture cost, better than existing common OLED device；The present invention also provides the preparation method of organic photoelectrical material, the preparation method is simple, raw material is easy to get, and disclosure satisfy that the needs of industrialization development；The organic photoelectrical material of the present invention has good application effect in OLED luminescent devices, has good industrialization prospect.
Description
Technical field
The present invention relates to technical field of photoelectric material preparation, and in particular to a kind of photoelectric material of sulfur-bearing and its preparation side
Method.
Background technology
Current world economy is mainly built upon with fossil energy, on the basis such as coal, oil and natural gas, so
And these non-renewable fossil energies are all continuous exhausted.Since the 21th century, global energy problem and with
And the environmental pollution and the problems such as climate warming that come increasingly show especially and gradually aggravate.Since solar energy is generally and wide with distribution
Wealthy, resource quantity is more, pollution-free, cleaning, safety and obtains outstanding advantages of facilitating, it is considered to be most promising renewable
One of energy, therefore research related with photoelectric material in recent years increasingly receives the concern of people.
Since inorganic photovoltaic material source is limited, expensive, preparation process is complicated, the limitation of the too high factor of cost,
More and more researchs are concentrated on organic photoelectrical material.Organic photoelectrical material is a kind of organic material with photoelectric converting function
Material, it is typically the organic molecule with big pi-conjugated key, is widely used in OLED (organic light emitting diode), OFET (fields
Effect transistor) and the photoelectric devices such as OSC (solar cell) in.It is with material source is extensive, property is various, type is numerous
It is more, be easily worked, be light-weight, is of low cost, safety and environmental protection, manufacture craft is simple, product weight is light, can large area flexible prepare
The advantage that cannot be compared Deng tradition inorganic material.It can be widely used in the multiple fields such as building, illumination and power generation simultaneously,
With important development and application prospect, thus the research institution of lot of domestic and foreign and enterprise etc. all give comparable concern and
Input.
In numerous organic photoelectrical materials, the organic photoelectrical material of sulfur atom-containing shows extraordinary charge transmission
Property is one of most worthy and the material of potential advantages.The organic photoelectrical material of sulfur atom-containing is typically all to pass through thiphene ring
Form introduce sulphur atom, thiphene ring is much like with phenyl ring, and also there are six pi-electrons, are the aromatic heterocycles of electron rich.Due to sulphur
Atom red shift, armaticity, which weakens the π superpositions between thiophene unit, increases coefficient influence, this micromolecular has higher two
Rank polarizability has many good photoelectric properties.
The photoelectric material of sulfur-bearing is often used on photoelectric device on the market now, but photoelectric property is undesirable, conversion
Rate efficiency is low, and cost of manufacture is high.
Invention content
In view of the deficiencies of the prior art, the present invention provides a kind of photoelectric materials of sulfur-bearing, have photoelectric property excellent, turn
The advantages that rate is efficient, low manufacture cost.
In order to achieve the above object, the present invention is achieved by the following technical programs：
A kind of photoelectric material of sulfur-bearing, general formula of molecular structure are following (I), and R1 is selected from isopropyl or tertiary butyl in formula,
R2 is selected from phenyl or cyclohexyl.
Preferably, the n in the general structure is the integer of 18-25.
Preferably, a kind of photoelectric material of sulfur-bearing, preparation method include the following steps：
A, 3- butyl thiophenes and isopropyl or tertiary butyl are added in organic solvent, wherein 3- butyl thiophenes and isopropyl
Or tertiary butyl molar ratio is 1:2.3-2.8；Reaction temperature for room temperature to flow back, reaction time 11-15h, after reaction, reaction solution
It is 28 DEG C to be cooled to temperature, and distillation obtains midbody product A (formula 1), spare；
B, by thiophenecarboxaldehyde and phenyl, either cyclohexyl is added in organic solvent wherein thiophenecarboxaldehyde and phenyl or ring
Hexyl molar ratio is 1.1:2.5-2.9；Reaction temperature for room temperature to flow back, reaction time 12-13h, after reaction, reaction solution is cold
But it is 28 DEG C to temperature, distillation obtains midbody product B (formula 2), spare；
C, midbody product B (formula 2) obtained by midbody product A (formula 1) and step c obtained by step a is placed in mobile phase has
In solvent, catalyst is added；Under nitrogen protection, 18-24h is reacted at room temperature, then filters reaction mixture, is filtered
Liquid is washed, after separation, dry organic phase, after prolapse solvent, silica gel post separation, post separation mobile phase for carbon disulfide with it is organic molten
The mixed solvent of agent, volume ratio 1:1.8-2.6 obtains midbody product (formula 3)；
D, midbody product (formula 3) is dissolved in the mixed solvent with chloroform and methyl cyanide, adds oxidant, mole
Than being 1：6.5-9.6, the reaction mixture flow back in the environment of 30 DEG C, reaction time 36-44h, after reaction, reaction solution water
It washes, the organic phase of separation is dried with anhydrous sodium sulfate, after prolapse solvent, obtains organic photoelectrical material (formula 4).
Preferably, the mobile phase organic solvent for one kind in dichloromethane, chloroform, carbon tetrachloride and chlorobenzene or
Two kinds of person.
Preferably, the oxidant is one kind in ferric trichloride, ferric perchlorate and hexafluoro-antimonic acid nitre.
Preferably, reaction solution washing time is 8-12h in the step d.
Advantageous effect：
Contain thiphene ring in its structure of organic photoelectrical material prepared by the present invention, since thiphene ring is five-membered ring structure, symbol
Shock youngster's rule is closed, there is moderate band gap, wider spectral response, preferable thermal stability and environmental stability, it is organic
Photoelectric material photoelectric property is excellent, and conversion ratio is efficient, low manufacture cost, better than existing common OLED device.The present invention also carries
For the preparation method of organic photoelectrical material, the preparation method is simple, raw material is easy to get, and disclosure satisfy that the needs of industrialization development.This
The organic photoelectrical material of invention has good application effect in OLED luminescent devices, has good industrialization prospect.
Specific embodiment
Purpose, technical scheme and advantage to make the embodiment of the present invention are clearer, below in conjunction with the embodiment of the present invention,
Technical solution in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making
All other embodiments obtained under the premise of creative work, shall fall within the protection scope of the present invention.
Embodiment 1：
In order to achieve the above object, the present invention is achieved by the following technical programs：
A kind of photoelectric material of sulfur-bearing, general formula of molecular structure are following (I), and R1 is selected from isopropyl or tertiary butyl in formula,
R2 is selected from phenyl or cyclohexyl.
The integer that n in general structure is 18.
A kind of photoelectric material of sulfur-bearing, preparation method include the following steps：
A, 3- butyl thiophenes and isopropyl or tertiary butyl are added in organic solvent, wherein 3- butyl thiophenes and isopropyl
Or tertiary butyl molar ratio is 1:2.3；Reaction temperature for room temperature to flow back, reaction time 11h, after reaction, reaction solution is cooled to
Temperature is 28 DEG C, and distillation obtains midbody product A (formula 1), spare；
B, by thiophenecarboxaldehyde and phenyl, either cyclohexyl is added in organic solvent wherein thiophenecarboxaldehyde and phenyl or ring
Hexyl molar ratio is 1.1:2.5；Reaction temperature for room temperature to flow back, reaction time 12h, after reaction, reaction solution is cooled to temperature
It is 28 DEG C to spend, and distillation obtains midbody product B (formula 2), spare；
C, midbody product B (formula 2) obtained by midbody product A (formula 1) and step c obtained by step a is placed in mobile phase has
In solvent, catalyst is added；Under nitrogen protection, 18h is reacted at room temperature, then filters reaction mixture, filtrate
Washing, after separation, dry organic phase, after prolapse solvent, silica gel post separation, post separation mobile phase is carbon disulfide and organic solvent
Mixed solvent, volume ratio 1:2.2, obtain midbody product (formula 3)；
D, midbody product (formula 3) is dissolved in the mixed solvent with chloroform and methyl cyanide, adds oxidant, mole
Than being 1：6.5, which flows back in the environment of 30 DEG C, reaction time 44h, after reaction, reaction solution washing, and separation
Organic phase dried with anhydrous sodium sulfate, after prolapse solvent, obtain organic photoelectrical material (formula 4).
Mobile phase organic solvent is dichloromethane.
Oxidant is ferric trichloride.
Reaction solution washing time is 8h in step d.
Embodiment 2：
A kind of photoelectric material of sulfur-bearing, general formula of molecular structure are following (I), and R1 is selected from isopropyl or tertiary butyl in formula,
R2 is selected from phenyl or cyclohexyl.
The integer that n in general structure is 21.
A kind of photoelectric material of sulfur-bearing, preparation method include the following steps：
A, 3- butyl thiophenes and isopropyl or tertiary butyl are added in organic solvent, wherein 3- butyl thiophenes and isopropyl
Or tertiary butyl molar ratio is 1:2.5；Reaction temperature for room temperature to flow back, reaction time 13h, after reaction, reaction solution is cooled to
Temperature is 28 DEG C, and distillation obtains midbody product A (formula 1), spare；
B, by thiophenecarboxaldehyde and phenyl, either cyclohexyl is added in organic solvent wherein thiophenecarboxaldehyde and phenyl or ring
Hexyl molar ratio is 1.1:2.7；Reaction temperature for room temperature to flow back, reaction time 12.5h, after reaction, reaction solution is cooled to
Temperature is 28 DEG C, and distillation obtains midbody product B (formula 2), spare；
C, midbody product B (formula 2) obtained by midbody product A (formula 1) and step c obtained by step a is placed in mobile phase has
In solvent, catalyst is added；Under nitrogen protection, 21h is reacted at room temperature, then filters reaction mixture, filtrate
Washing, after separation, dry organic phase, after prolapse solvent, silica gel post separation, post separation mobile phase is carbon disulfide and organic solvent
Mixed solvent, volume ratio 1:1.8, obtain midbody product (formula 3)；
D, midbody product (formula 3) is dissolved in the mixed solvent with chloroform and methyl cyanide, adds oxidant, mole
Than being 1：8.2, which flows back in the environment of 30 DEG C, reaction time 41h, after reaction, reaction solution washing, and separation
Organic phase dried with anhydrous sodium sulfate, after prolapse solvent, obtain organic photoelectrical material (formula 4).
Mobile phase organic solvent is chloroform and carbon tetrachloride.
Oxidant is ferric perchlorate.
Reaction solution washing time is 10h in step d.
Embodiment 3：
A kind of photoelectric material of sulfur-bearing, general formula of molecular structure are following (I), and R1 is selected from isopropyl or tertiary butyl in formula,
R2 is selected from phenyl or cyclohexyl.
The integer that n in general structure is 25.
A kind of photoelectric material of sulfur-bearing, preparation method include the following steps：
A, 3- butyl thiophenes and isopropyl or tertiary butyl are added in organic solvent, wherein 3- butyl thiophenes and isopropyl
Or tertiary butyl molar ratio is 1:2.8；Reaction temperature for room temperature to flow back, reaction time 15h, after reaction, reaction solution is cooled to
Temperature is 28 DEG C, and distillation obtains midbody product A (formula 1), spare；
B, by thiophenecarboxaldehyde and phenyl, either cyclohexyl is added in organic solvent wherein thiophenecarboxaldehyde and phenyl or ring
Hexyl molar ratio is 1.1:2.9；Reaction temperature for room temperature to flow back, reaction time 13h, after reaction, reaction solution is cooled to temperature
It is 28 DEG C to spend, and distillation obtains midbody product B (formula 2), spare；
C, midbody product B (formula 2) obtained by midbody product A (formula 1) and step c obtained by step a is placed in mobile phase has
In solvent, catalyst is added；Under nitrogen protection, it reacts for 24 hours, then filters reaction mixture at room temperature, filtrate
Washing, after separation, dry organic phase, after prolapse solvent, silica gel post separation, post separation mobile phase is carbon disulfide and organic solvent
Mixed solvent, volume ratio 1:2.6, obtain midbody product (formula 3)；
D, midbody product (formula 3) is dissolved in the mixed solvent with chloroform and methyl cyanide, adds oxidant, mole
Than being 1：9.6, which flows back in the environment of 30 DEG C, reaction time 36h, after reaction, reaction solution washing, and separation
Organic phase dried with anhydrous sodium sulfate, after prolapse solvent, obtain organic photoelectrical material (formula 4).
Mobile phase organic solvent is dichloromethane and chlorobenzene.
Oxidant is hexafluoro-antimonic acid nitre.
Reaction solution washing time is 12h in step d.
It should be noted that herein, relational terms such as first and second and the like are used merely to a reality
Body or operation are distinguished with another entity or operation, are deposited without necessarily requiring or implying between these entities or operation
In any this practical relationship or sequence.Moreover, term " comprising ", "comprising" or its any other variant are intended to
Non-exclusive inclusion, so that process, method, article or equipment including a series of elements not only will including those
Element, but also including other elements that are not explicitly listed or further include as this process, method, article or equipment
Intrinsic element.In the absence of more restrictions, the element limited by sentence "including a ...", it is not excluded that
Also there are other identical elements in process, method, article or equipment including the element.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although with reference to the foregoing embodiments
The present invention is described in detail, it will be understood by those of ordinary skill in the art that：It still can be to aforementioned each implementation
Technical solution recorded in example modifies or carries out equivalent replacement to which part technical characteristic；And these modification or
It replaces, the spirit and scope for various embodiments of the present invention technical solution that it does not separate the essence of the corresponding technical solution.
Claims (6)
1. a kind of photoelectric material of sulfur-bearing, which is characterized in that its general formula of molecular structure is following (I), and R1 is selected from isopropyl in formula
Or tertiary butyl, R2 are selected from phenyl or cyclohexyl.
2. a kind of photoelectric material of sulfur-bearing according to claim 1, it is characterised in that：N in the general structure is 18-
25 integer.
3. the photoelectric material of a kind of sulfur-bearing according to claim 1, which is characterized in that preparation method includes following step
Suddenly：
A, 3- butyl thiophenes and isopropyl or tertiary butyl are added in organic solvent, wherein 3- butyl thiophenes and isopropyl or uncle
Butyl molar ratio is 1:2.3-2.8；Reaction temperature is room temperature to reflux, and reaction time 11-15h, after reaction, reaction solution cools down
It it is 28 DEG C to temperature, distillation obtains midbody product A (formula 1), spare；
B, by thiophenecarboxaldehyde and phenyl, either cyclohexyl is added in organic solvent wherein thiophenecarboxaldehyde and phenyl or cyclohexyl
Molar ratio is 1.1:2.5-2.9；Reaction temperature for room temperature to flow back, reaction time 12-13h, after reaction, reaction solution is cooled to
Temperature is 28 DEG C, and distillation obtains midbody product B (formula 2), spare；
C, that midbody product A (formula 1) and step c gained midbody product B (formula 2) obtained by step a are placed in mobile phase is organic molten
In agent, catalyst is added；Under nitrogen protection, 18-24h is reacted at room temperature, then filters reaction mixture, filtrate water
It washes, after separation, dry organic phase, after prolapse solvent, silica gel post separation, post separation mobile phase is carbon disulfide and organic solvent
Mixed solvent, volume ratio 1:1-1:3, obtain midbody product (formula 3)；
D, midbody product (formula 3) is dissolved in the mixed solvent with chloroform and methyl cyanide, adds oxidant, molar ratio is
1：6.5-9.6, the reaction mixture flow back in the environment of 30 DEG C, reaction time 36-44h, after reaction, reaction solution washing,
The organic phase of separation is dried with anhydrous sodium sulfate, after prolapse solvent, obtains organic photoelectrical material (formula 4).
4. a kind of preparation method of the photoelectric material of sulfur-bearing according to claim 1, it is characterised in that：The mobile phase has
Solvent is one or two kinds of in dichloromethane, chloroform, carbon tetrachloride and chlorobenzene.
5. a kind of preparation method of the photoelectric material of sulfur-bearing according to claim 1, it is characterised in that：The oxidant is
One kind in ferric trichloride, ferric perchlorate and hexafluoro-antimonic acid nitre.
6. a kind of preparation method of the photoelectric material of sulfur-bearing according to claim 1, it is characterised in that：In the step d
Reaction solution washing time is 8-12h.
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| CN110358058A (en) * | 2019-07-16 | 2019-10-22 | 武汉轻工大学 | A kind of organic photoelectrical material and preparation method thereof, luminescent device and display device |
| CN110642829A (en) * | 2019-10-14 | 2020-01-03 | 中材江苏太阳能新材料有限公司 | Photoelectric material containing thiophene ring and preparation method thereof |
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| CN110358058A (en) * | 2019-07-16 | 2019-10-22 | 武汉轻工大学 | A kind of organic photoelectrical material and preparation method thereof, luminescent device and display device |
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| CN110642829A (en) * | 2019-10-14 | 2020-01-03 | 中材江苏太阳能新材料有限公司 | Photoelectric material containing thiophene ring and preparation method thereof |
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