JP3131644B2 - Polymer and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polymer, an application device thereof, and a method for producing the polymer, and more particularly to a polymer having conductivity and solubility, an application device thereof, and a method for producing the polymer.

[0002]

2. Description of the Related Art In recent years, many functional organic materials have begun to be used industrially in the fields of electronics and optoelectronics. The pi-conjugated polymer material has functions such as conductivity, electricity storage, and electrochromic properties, and can be applied to devices.

[0003] However, few materials have been used industrially due to problems such as lack of variety of materials and difficulty in molding. Specifically, it is considered that the fact that there are fewer types of pi-conjugated polymers having the property of doping cations than those having the property of doping anions is a major reason for the lack of diversity. In addition, the fact that the pi-conjugated polymer is generally insoluble or infusible is considered to be the cause of inferior processability as compared with other polymer materials.

[0004]

As described above, the pi-conjugated polymer material has a function applicable to a functional device, but in reality, few are actually used industrially.

[0005] An object of the present invention is to provide a novel pi-conjugated polymer having solubility.

Another object of the present invention is to provide a novel pi-conjugated polymer which can be doped with a cation.

[0007] Another object of the present invention is to provide a functional device using such a polymer.

Another object of the present invention is to provide a method for producing such a polymer.

[0009]

According to one aspect of the present invention, a general formula

[0010]

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There is provided a polymer comprising a repeating unit represented by R = alkyl or alkoxy.

According to another aspect of the invention, the general formula

[0013]

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A compound represented by R = alkyl or alkoxy is represented by the general formula

[0015]

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2. The method according to claim 1, further comprising the step of copolymerizing with a compound represented by X = Br, Cl, I.
Are provided.

It is considered that conductivity is imparted by an alternate linear structure of a benzene ring and a pyridine ring.

It is considered that solubility is imparted by connecting an alkyl group or an alkoxy group to a position opposite to the benzene ring.

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS General formulas according to embodiments of the present invention

[0020]

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R is a polymer comprising a repeating unit represented by an alkyl group or an alkoxy group represented by the general formula:

[0022]

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R = a compound represented by an alkyl group or an alkoxy group;

[0024]

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A method for obtaining by copolymerizing a compound represented by X = Br, Cl, I will be described.

Examples of the polymerization catalyst include tetrakis (triphenylphosphine) palladium. The reaction solvent can be a mixture of an aqueous solution made basic with sodium carbonate, toluene and ethanol. It seems that copolymerization using the Grignard reaction is also good as another polymerization method.

First, a method for producing 2.5-dihexylbenzene-1.4-bisboronic acid, which is a raw material of the polymer, will be described. This method is a known method (M. Reh.
ahnet al, Synthesis Communications, 386 (1988) and M. Rehahn et al, Makromol. Chem.
1 (1990)).

First, 1,4-dihexylbenzene as a precursor is synthesized. The reaction was performed in argon gas.
First, 5.9 g of 1,4-dichlorobenzene (40 mm
ol) and [1,3-bis (diphenylphosphino) propane] dichloronickel (I
I) Ni (dppp) Cl ₂ 27 mg (0.045 mm
ol) was dissolved in 30 ml of dry ether. While cooling in an ice bath, 0.1 mol of n-hexylmagnesium bromide (50 ml of a 2M ether solution) was added with stirring. The addition was performed for 10 minutes using a syringe. After 5 minutes, the ice bath was removed, and the reaction was carried out at room temperature for 30 minutes. The reaction solution turned transparent greenish brown. Further reaction at reflux temperature for 19 hours produced a white creamy product in the flask. Next, cool the reaction solution in an ice bath,
The reaction was stopped by slowly adding 2.5 ml of pure water and 25 ml of 2N hydrochloric acid. At this time, slight boiling and heat generation were observed. The reaction solution was separated into an aqueous phase and an ether phase, and the aqueous phase was extracted twice with 10 ml of ether. The ether phase and the extract were combined, washed with 5 ml of pure water, and dried by adding 3 g of magnesium sulfate. Ether was distilled off from the reaction solution by a rotary evaporator, and the remaining light brown product was purified by distillation under reduced pressure. A transparent main component distilled at 2.7 mmHg and 165 ° C. was obtained. 8.5 g (yield 86)
%)Met.

Next, 1,4-dibromo-2,5-dihexylbenzene is synthesized using the obtained 1,4-dihexylbenzene. 8.4 g of 1,4-dihexylbenzene
(34 mmol) and 45 mg (340 mmol) of iodine
l) was placed in a flask, and the system was completely shielded from light while cooling and stirring in an ice bath to obtain 3.6 ml of bromine (11.2 g;
mol) was added. Bromine was added using a dropping funnel and added for 15 minutes.
Went over a minute. Hydrogen bromide gas was violently generated at the same time as the addition, and this was collected by a water trap. Gas generation is about 2
It is hardly seen in time. The reaction was continued for 24 hours at room temperature to obtain a solid reaction product. 20%
The reaction was stopped by adding 21 ml of an aqueous potassium hydroxide solution and heating to 60 ° C. The reaction solution is divided into an aqueous phase and an organic phase heavier than the aqueous phase. The organic phase was crystallized on ice and the aqueous phase was removed by decantation. 80 m of product obtained
Recrystallization once with 1 l of ethanol and twice with 40 ml of ethanol gave white crystals. Here, a yield of 5.4 g (yield 3
9%). The melting point is 40.0-41.0 ° C. Further extraction and purification were repeated using the recrystallization filtrate, and 3.3 g was obtained.
Was obtained as white crystals.

Next, the obtained 1,4-dibromo-2,5
-Dihexylbenzene is used as the starting material for the polymer 2,
5-Dihexylbenzene-1,4-bisboronic acid is synthesized. The reaction was performed under an argon gas atmosphere. 10.3 g (25.6 mmol) of 1,4-dibromo-2,5-dihexylbenzene was placed in a 300 ml flask, and dissolved by adding 80 ml of dry hexane. The solution was heated to reflux temperature and 42.4 ml (67.
8 mmol) in 1.6 M n-butyllithium-hexane solution was added in 15 minutes using a syringe. The reaction solution gradually formed a yellow-white precipitate. Reflux for 24 hours,
After returning to room temperature, the mixture was cooled to -70 ° C in a dry ice-ethanol bath, and 23.8 ml (215 mmol) was obtained.
Of trimethyl borate was added. After the addition, the temperature was raised to 20 ° C., and the mixture was stirred for 10 hours. As the temperature of the reaction increases,
The color changed from pale yellow to pale white. Next, 90 ml of 2N hydrochloric acid was added to the obtained reaction solution, and the mixture was stirred for 24 hours.
The generated white precipitate was separated by filtration and washed with 180 ml of hot water. The precipitate was once dried under vacuum, dissolved in 112 ml of acetone, and precipitated again by adding 11.2 ml of 2N hydrochloric acid. The precipitate was collected by filtration and dried in vacuo at 90 ° C. by aspirator suction to obtain a white product. Yield 1.8
The amount was 1 g (yield 21%).

The identification of the raw material obtained by the synthesis will be described. The melting point is between 167 and 172 ° C.
172 ° C.

FIG. 1 shows an IR spectrum of the obtained synthesis raw material. Large broad O- around 3300cm ^-1
An absorption peak attributed to H stretching was observed, and 1402 cm
^{At −1} , an absorption based on B-φ was observed, and at 1366 cm ⁻¹ , a large absorption peak attributed to BO stretching vibration was observed. These absorptions are considered to be absorptions derived from the boronic acid group. Absorption of aliphatic C—H stretching vibration is observed at 2956, 2923, and 2851 cm ⁻¹ . This can be determined as absorption derived from the n-hexyl group of the product. 112
The absorption peaks at 6, 1033 and 834 cm ^-1 are those of aromatic ring C-
It is attributed to H bending vibration and is determined to be absorption due to the benzene ring skeleton. From the results of the IR spectrum, the molecular structure of 2,5-dihexylbenzene-1,4-bisboronic acid is supported. From the melting point and IR spectrum, the product was identified as 2,5-dihexylbenzene-1,4-bisboronic acid.

Next, a method for producing poly (2,5-dihexyl-1,4-phenylene-alt-2,5-pyridinediyl) (poly-dhpp), which is a polymer, will be described. 0.237 g (1 mmol) of 2,5-dibromopyridine and 34.6 mg (0.03 mmol) of tetrakis (triphenylphosphine) palladium (0) were dissolved in toluene in a 50 ml flask. After adding 1,2 ml of 2M sodium carbonate to make a basic solution, 0.367 g dissolved in 2.5 ml of ethanol.
(1.1 mmol) of 2,5-dihexylbenzene-
1,4-bisboronic acid was added at room temperature. The solution turned from a pale yellow to an orange suspension. Immediately, the mixture was heated to 80 to 85 ° C. using an oil bath and reacted under reflux. Shortly after the reflux started, the reaction solution became clear. After reacting for 16 hours, the temperature was returned to room temperature, and the solvent of the reaction solution was distilled off with a rotary evaporator. The remaining product was successively washed twice with 20 ml of acetone and 30 ml of 1N hydrochloric acid, and dried under vacuum at 90 ° C. for 2 hours to obtain a pale yellow product. The yield was 0.301 g (94% yield).

The identification of the obtained product will be described.
FIG. 2 shows the IR spectrum of the product. 2956, 29
24,2856Cm ^-1 to the absorption attributed to the aliphatic C-H stretching vibration, the absorption attributed to the pyridine ring skeleton vibration of 1468cm ^-1, 1070,1020,902,848cm
^{At -1} , an absorption peak attributed to the aromatic ring CH bending vibration is observed. These are consistent with the characteristics of the molecular structure of poly-dhpp. Further, 1070 cm ^-1 in the raw material of 2,5-dibromopyridine was seen 482cm ^-1 C-Br
And the other material, 2,5
B-φ, B- at 1402, 1336 cm ^-1 found in dihexylbenzene-1,4-bisboronic acid
The absorption peak attributed to O, and the absorption attributed to the OH stretching vibration observed near 3300 cm ^-1 was not observed in the product. This supports the formation of a polymer by the elimination of the bromine and boronic acid groups of the raw material.

FIG. 3 shows the ¹ H-NMR spectrum of the product. The analysis results are summarized as follows,
Each hydrogen of -dhpp was assigned to each peak in the spectrum. CDCl ₃ δ = 8.76 (1H, aromatic-H) δ = 7.81 (1H, aromatic-H) δ = 7.55 (1H, aromatic-H) δ = 7.44 (1H, aromatic-H) δ = 7.28 (1H, aromatic-H) δ = 2.76 (4H, α-CH ₂ ) δ = 1.56 (4H, β-CH ₂ ) δ = 1.24 (12H, γ, δ, ε-CH ₂ ) δ = 0.85 (6H, CH ₃ ) From the above analysis results, the product was identified as Poly-dhpp. Further, the following analysis was performed.

The molecular weight was determined by gel permeation chromatography (GPC). The column used was a gel filtration column. The mobile phase used was tetrahydrofuran, the column temperature was 40 ° C., and the flow rate was 1 ml / min. I went in. Polystyrene was used as a standard sample.

FIG. 4 shows the obtained chromatogram. As a result of analysis, the weight average molecular weight of poly-dhpp was about 1
1000, the average degree of polymerization n per repeating unit is 3
It was 4.

FIG. 5 shows an ultraviolet-visible (UV-VIS) spectrum in chloroform. The absorption peak was confirmed at 300 nm in the ultraviolet region. The molar extinction coefficient at 300 nm was 15 mM ^-1 · cm ^-1 . Since there is no absorption in the visible light region, it indicates that the material is a transparent material.

The polymer was soluble in organic solvents such as chloroform, dichloromethane and tetrahydrofuran.
The solvent with the highest solubility is chloroform, 40 mg
/ Ml or more. The solubility was improved by heating.

FIG. 6 shows cyclic voltammetry (C
The result of the electrochemical redox measurement according to V) is shown. Platinum was used for the working electrode and the counter electrode, silver wire was used for the reference electrode, acetonitrile was used for the solvent, and tetra-n-butylammonium tetrafluoroborate was used for the supporting electrolyte. The scanning speed was 100 mV / sec. In the figure, the vertical axis shows current, and the horizontal axis shows potential (vs. Ag wire). When the potential was scanned in the negative direction, a peak due to the reduction current was observed at about -2.2 V, and when the scanning direction was reversed, a current peak in the opposite direction was observed. An electrochromic phenomenon was confirmed in which the color of the polymer changed from colorless and transparent to green at the same time as the reduction current, and again changed to colorless at the same time when the scanning direction was reversed. Therefore, it can be determined that this current peak is due to doping of the supporting electrolyte ion (tetra-n-butylammonium ion) with respect to poly-dhpp.
Is a polymer having n-type properties.

This polymer is soluble in various organic solvents. Chloroform, tetrahydrofuran, dichloromethane and benzene are good solvents. Partially soluble in toluene and n-hexane. It is possible to dissolve at least 40 mg / ml in chloroform, which is the most soluble solvent. The solubility can be further improved by dissolving while heating.

The polymer is doped with cations.
can do. Electrochemical or chemical method
Doping can be performed by using such a method. As an ion
Li +, Na⁺, K⁺, Rb⁺, Cs⁺Such as alkali
Metal ion, H_FourN⁺, Me _FourN⁺, Et_FourN⁺, (N
-Bu)_FourN⁺Quaternary alkyl ammonium ions such as
And the like. In addition, halogen such as iodine
The gas can be doped as an anion.

In the case of electrochemical doping, the polymer supported on the electrode surface is immersed in an electrolytic solution, and ions are doped by applying a voltage between the polymer and another counter electrode or by flowing a current. By appropriately controlling the applied voltage or current, ions can be reversibly attached and detached.

In this case, the cations are supplied from a supporting electrolyte dissolved in the electrolyte. Examples of the electrode supporting the polymer include platinum, gold, carbon, and indium-tin oxide. Alkyl ammonium tetrafluoroborate such as tetra-n-butylammonium tetrafluoroborate; alkali metal salts of tetrafluoroborate such as lithium tetrafluoroborate; alkylammonium perchlorates such as tetraethylammonium perchlorate; and perchloric acid as a supporting electrolyte Alkali metal salts of perchloric acid such as lithium; alkyl ammonium salts of tetrafluorophosphate such as tetra-n-butylammonium tetrafluorophosphate; alkali metal salts of tetrafluorophosphate such as sodium tetrafluorophosphate; tetra-p-toluenesulfonic acid Examples thereof include p-toluenesulfonic acid alkyl ammonium salts such as methyl ammonium and sodium trifluoroacetate. Examples of the solvent include acetonitrile, propylene carbonate, nitromethane, sulfolane, N-methylpyrrolidone, dimethylformamide, dimethylsulfoxide and the like.

When the polymer is doped with a cation,
A color change from colorless to green occurs. In addition, it returns to colorless by undoping. When such an electrochromic phenomenon is used, it can be used as a display material. Similarly, a full-color display can be performed by combining with another material exhibiting a red or blue electrochromic reaction.

By taking advantage of the characteristic that ion doping can be performed reversibly, it can be used as a charge / discharge material.

In the above examples, the degree of polymerization of the polymer was 34 and the weight average molecular weight was about 11,000, but the weight average molecular weight was 3,000 to 100,000, preferably 50
It is preferable to set it to 00 to 50,000.

Although a structure in which an alkyl group is bonded to a benzene ring is used, similar results will be obtained by using a structure in which an alkoxy group is bonded.

Although the case where the alkyl group has 6 carbon atoms has been described, an alkyl group or an alkoxy group having 1 to 30, preferably 4 to 18 carbon atoms could be used.

For these polymers, chloroform, tetrahydrofuran, dichloromethane and benzene will be good solvents. It will be partially soluble in toluene and n-hexane. Heating will improve solubility.

Also, these polymers could be doped with cations. The ion could be doped by using an electrochemical method or a chemical method. As ions, Li ⁺ , N
alkali metal ions such as a ⁺ , K ⁺ , Rb ⁺ , and Cs ^{+
_{H 4 N +, Me 4 N}} +, Et 4 N +, (n-Bu) 4 N
Cations such as quaternary alkylammonium ions such as ⁺
Also, an anion of a halogen gas such as iodine could be used.

In the case of electrochemical doping, a polymer is supported on the surface of an electrode, immersed in an electrolytic solution, and a voltage is applied or a current is applied between the electrode and a counter electrode. By properly controlling the applied voltage or current, ions could be reversibly attached and detached. Cations can be supplied from a supporting electrolyte dissolved in the electrolyte. Examples of the electrode supporting the polymer include platinum, gold, carbon, and indium-tin oxide. As a supporting electrolyte, an alkylammonium tetrafluoroborate salt such as tetra-n-butylammonium tetrafluoroborate; an alkali metal salt of tetrafluoroborate such as lithium tetrafluoroborate;
Alkylammonium perchlorates such as tetraethylammonium perchlorate; alkali metal perchlorates such as lithium perchlorate; alkylammonium tetrafluorophosphates such as tetra-n-butylammonium tetrafluorophosphate; sodium tetrafluorophosphate and the like Examples thereof include alkali metal salts of tetrafluorophosphate, alkyl ammonium salts of p-toluenesulfonic acid such as tetramethylammonium p-toluenesulfonate, and alkali metal salts of trifluoroacetic acid such as sodium trifluoroacetate.

Examples of the solvent include acetonitrile, propylene carbonate, nitromethane, sulfolane, N-methylpyrrolidone, dimethylformamide, dimethylsulfoxide and the like.

When the polymer is doped with a cation,
A color change will occur. When such an electrochromic phenomenon is used, it can be used as a display material. If the property that ions can be reversibly doped is used, it can be used as a charge / discharge material.

FIG. 7 shows an electrochromic display device. As shown in FIG. 7A, the electrochromic display device has a matrix display section 10 and is configured to be capable of displaying pixels. The matrix display unit 10 is connected to a power supply 14 via a control circuit 12.

FIG. 7B schematically shows the structure of one pixel of the matrix display unit 10. An electrochromic material layer 22 made of poly-dhpp is applied on the surface of the electrode 21 which is both a supporting electrode and a background. The surface of the electrochromic material layer is covered with the electrolyte 23. On the opposite side of the electrolyte 23, a transparent electrode 24 is arranged. Note that a spacer 26 is arranged so as to surround a region for one pixel.

In the pixel for green display, poly-dhpp is used as the electrochromic material layer. For pixels of other colors, an electrochromic material suitable for the color is used.

As shown in FIG. 6, poly-dhpp has a property of coloring when a negative voltage is applied.
Common red and blue electrochromic materials are:
It has the property of coloring when a positive voltage is applied. When these positive and negative electrochromic materials are used simultaneously, it is necessary to reverse the polarity of the power supply voltage.

FIG. 7C shows an equivalent circuit configuration including a power supply voltage polarity inversion switch SW. The voltage of the power supply 14 has a desired polarity selected by the polarity inversion switch SW, and is supplied between the support electrode 21 and the transparent electrode 24. A desired display is performed by applying signals of appropriate polarity and voltage to each pixel of the matrix display unit 10.

Various known signal driving methods, display screen sizes, and the like can be adopted. The polymer according to the above-described embodiment has a property of allowing reversible ion doping, and can be used as a charge / discharge material.

FIG. 8 schematically shows the structure of a battery utilizing the properties as a charge / discharge material. The battery 30 has a configuration housed in an insulating case 40, and the negative electrode 31 and the positive electrode 39 are exposed on opposing surfaces of the case 40. Negative electrode 3
1 is electrically and mechanically connected to the negative electrode current collector 32. A negative electrode material 33 made of poly-dhpp is applied to the surface of the negative electrode current collector 32.

The positive electrode 39 is electrically and mechanically connected to the positive electrode current collector 38. On the surface of the positive electrode current collector 38,
A positive electrode material 37 selected from known materials is applied. A separator 3 is provided between the negative electrode material 33 and the positive electrode material 37.
5 are arranged. The separator 35 is formed of a porous resin film or the like, and has a function of shutting off the current when the battery runs away, by closing the porous hole by increasing the temperature. Negative electrode material 3
3. An intermediate space between the positive electrode materials 37 is filled with the electrolytes 34 and 36. The ions are reversibly moved between the negative electrode material 33 and the positive electrode material 37 to charge and discharge the battery.

The present invention has been described in connection with the preferred embodiments.
The present invention is not limited to these. For example,
It will be apparent to those skilled in the art that various modifications, improvements, combinations, and the like can be made.

[0064]

As described above, according to the present invention,
New polymers are provided. A polymer soluble in an organic solvent and capable of reversibly doping cations can be obtained.

[Brief description of the drawings]

FIG. 1 is a graph showing an IR spectrum of a polymer raw material manufactured by a manufacturing method according to an example of the present invention.

FIG. 2 is a graph showing an IR spectrum of a polymer obtained by a production method according to an example of the present invention.

FIG. 3 shows ¹ H- of a polymer obtained according to an example of the present invention.
It is a graph which shows an NMR spectrum.

FIG. 4 is a graph showing a gel permeation chromatogram of a polymer obtained by a production method according to an example of the present invention.

FIG. 5 is a graph showing an ultraviolet-visible absorption spectrum of a polymer obtained by a production method according to an example of the present invention.

FIG. 6 is a graph showing cyclic voltammetry characteristics of a polymer obtained by a production method according to an example of the present invention.

FIG. 7 is a schematic view, a partially cutaway perspective view, and a sectional view showing an electrochromic display device according to an embodiment of the present invention.

FIG. 8 is a cross-sectional view schematically illustrating a configuration of a battery according to an embodiment of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 10 Matrix display part 21 Supporting electrode and background body 22 Electrochromic material 23 Electrolyte 24 Transparent electrode 31 Negative electrode 32, 38 Current collector 33 Negative electrode material 35 Separator 39 Positive electrode 34, 36 Electrolyte

────────────────────────────────────────────────── ─── Continued on the front page Examiner Satoshi Morikawa (56) References JP-A-7-138349 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 61/12 CA (STN ) REGISTRY (STN)

Claims (16)

(57) [Claims] 1. A compound of the general formula R = polymer comprising a repeating unit represented by an alkyl group or an alkoxy group. 2. The polymer has a weight average molecular weight of 3,000.
The polymer of claim 1 which is in the range of ~ 100,000. 3. The polymer according to claim 1, wherein said R has 1 to 30 carbon atoms. 4. The polymer according to claim 1, wherein said R has 4 to 18 carbon atoms. 5. A compound obtained by doping the polymer according to claim 1 with ions. 6. A compound obtained by doping the polymer according to claim 1 with a cation. 7. The compound according to claim 6, wherein said cation is an alkali metal ion or a quaternary alkyl ammonium ion. 8. A compound of the general formula R = a polymer comprising a repeating unit represented by an alkyl group or an alkoxy group, wherein the color of the organic display material changes when reversibly doped with ions. 9. A compound of the general formula R = a polymer comprising a repeating unit represented by an alkyl group or an alkoxy group, wherein the charge / discharge material changes reversibly the electrochemical state by doping with a cation. 10. A negative electrode current collector, coated on the negative electrode current collector, having the general formula: A negative electrode material containing a polymer comprising a repeating unit represented by R = alkyl group or alkoxy group, a positive electrode current collector, a positive electrode material applied on the positive electrode current collector, the negative electrode material and the positive electrode material, A battery comprising: a separator disposed therebetween; and an electrolyte disposed to fill a space between the negative electrode material and the positive electrode material. 11. The battery according to claim 10, wherein said polymer is poly (2,5-dihexyl-1,4-phenylene-alt-2,5-pyridinediyl) (poly-dhpp). 12. The electrolyte according to claim 1, wherein the electrolyte is an alkylammonium tetrafluoroborate, an alkali metal tetrafluoroborate, an alkylammonium perchlorate, an alkali metal perchlorate, an alkylammonium tetrafluorophosphate, a tetrafluorophosphate. 2. The composition according to claim 1, comprising at least one of an alkali metal salt, an alkylammonium p-toluenesulfonate, and an alkali metal trifluoroacetate.
The battery according to 0 or 11. 13. A support electrode, and is coated on the support electrode, and has a general formula: R = an electrochromic layer containing a polymer comprising a repeating unit represented by an alkyl group or an alkoxy group; a counter electrode disposed on the electrochromic layer; and a space between the electrochromic layer and the counter electrode. An electrochromic display device comprising: 14. The electrochromic display device according to claim 13, wherein said polymer is poly (2,5-dihexyl-1,4-phenylene-alt-2,5-pyridinediyl) (poly-dhpp). 15. The electrochromic display device according to claim 13, wherein at least one of said support electrode and said counter electrode is a transparent electrode. 16. A compound represented by the general formula: A compound represented by R = alkyl or alkoxy is converted to a compound represented by the general formula: 2. The method according to claim 1, further comprising a step of copolymerizing with a compound represented by X = Br, Cl, I.
The method for producing a polymer according to the above.