WO2005049688A1

WO2005049688A1 - Conductive resin capable of photopatterning

Info

Publication number: WO2005049688A1
Application number: PCT/JP2004/017090
Authority: WO
Inventors: Fumiyuki Ozawa; Hiroyuki Katayama; Kensuke Akamatsu
Original assignee: Kansai Technology Licensing Organization Co., Ltd.
Priority date: 2003-11-21
Filing date: 2004-11-17
Publication date: 2005-06-02
Also published as: TW200517409A; JP5132057B2; JPWO2005049688A1; TWI374899B

Abstract

A conductive resin capable of nanometer-order pattering wherein direct patterning without the use of any resist can be performed. There is provided a material comprised of a poly(arylenevinylene) (the arylene is an arylene group or a heterocyclic compound group) of 1500 to 30000 number average molecular weight wherein the ratio of cis-poly(arylenevinylene) to trans-poly(arylenevinylene) is 65/35 or higher. The film produced from this material can be patterned by irradiating a given region with 200 to 600 nm light and leaching non-photoirradiated portions with an aromatic, halogenated or ether type organic solvent.

Description

Specification

Conductive resin capable of optical patterning

Technical field

The present invention relates to a conductive resin that can be directly putterung without using a resist.

Background art

[0002] As conductive resins, polyacetylene, polyphenylene, polyphenylenevinylene, polypyrrol and the like are well known. These are used as materials for organic EL (organic electroluminescence), organic FETs (organic field effect transistors), batteries, capacitors, etc. Depending on the application, it is necessary to pattern a film made of conductive resin. (See Patent Document 1, etc.).

[0003] For example, an EL element has a structure in which an electrode layer, a hole transport layer, an electron transport layer, and an electrode layer are sequentially laminated on a substrate of Si or the like. It is necessary to repeat the stacking and patterning of four layers in order. When performing patterning, a resist is applied on the electrode layer, etc., the resist is first patterned, and then the electrode layer, etc. is etched or physically etched using the resist as a mask. Is performed. The FET element has a structure in which, for example, a gate electrode, an insulating layer thin film, a source electrode, a channel layer, and a drain electrode are sequentially stacked, and the pattern of each layer is formed in the same manner as in the case of manufacturing an EL element. Jung is performed.

Patent Document 1: Japanese Patent Application Laid-Open No. 07-176470

Disclosure of the invention

Problems to be solved by the invention

If the patterning of the conductive film can be performed directly without using a resist, the number of steps for notching can be reduced. This makes it possible to improve product production efficiency and yield. In addition, since it is not necessary to develop the resist, the amount of the organic solvent used can be reduced, and the burden on the environment can be reduced. [0006] The problem to be solved by the present invention is to provide a conductive resin that can be directly puttered without using a resist and has a nanometer order! It is in.

Means for solving the problem

[0007] The conductive resin capable of optical pattern jungling according to the present invention, which has been made to solve the above problem, has a ratio of cis-poly (arylene bi-len) to trans-poly (arylene bi-len). It is characterized by comprising poly (arylene vinylene) having a number average molecular weight of not less than 65/35 and a number average molecular weight of 1500 to 30,000 (where arylene includes a heterocyclic compound group in addition to an arylene group).

[0008] In the present application, "conductivity" includes electric conductivity of a semiconductor level.

The inventor of the present application has reported that among poly (arylene bi-lenes) having conductivity (where arylene includes a heterocyclic compound group in addition to an arylene group), cis-poly (arylene bi-lene) is It is readily soluble in aromatic or halogen-based or ether-based organic solvents such as benzene, toluene, chloroform, methylene chloride, and tetrahydrofuran, and has a wavelength of 200-600 nm in this cis-poly (arylene vinylene). It has been found that the product obtained by irradiating the above-mentioned light hardly dissolves in the above organic solvent.

[0010] The detailed structure of this product is not clear at present. By light absorption measurement,

Trans-poly (arylene vinylene) is a force that has a characteristic spectrum observed. trans-poly (arylene vinylene) dissolves in the above organic solvents, so this product is trans-poly (arylene vinylene). It is not considered as such. It is considered that the irradiation of the cis-poly (arylene bi-lene) with the light having the above-mentioned wavelength further caused some reaction together with the isomerization reaction to trans-poly (arylene bi-lene). However, since it is clear that the light irradiation caused an isomeric reaction to the trans-isomer, the light-irradiated portion is hereinafter referred to as trans-poly (arylene bilen) or trans-isomer.

[0011] In the present invention, pattern jungling of a film is performed by utilizing the above properties of poly (arylene vinylene). That is, by irradiating a region of a film or the like made of cis-poly (arylene vinylene) with light having a wavelength of 200 to 600 nm, the light-irradiated portion is changed to trans-poly (arylene vinylene). Light emission using aromatic, halogen or ether organic solvents The non-irradiated portion is eluted in an organic solvent to form a pattern such as a circuit.

[0012] Since the cis-form poly (arylene vinylene) has a higher solubility in an aromatic, halogen-based or ether-based organic solvent than the trans-form, it can be washed by using such a solvent. Only the cis-form that is not irradiated with light is eluted, and the trans-form that is irradiated with light remains as a pattern. Since the trans body has conductivity, a pattern of a circuit or the like can be directly formed by using the conductive resin of the present invention.

[0013] Further, the trans body also has an electroluminescent property that emits light at a wavelength specific to the substance when a voltage is applied. Therefore, by forming a pattern using the conductive resin of the present invention, a light emitting layer of a light emitting device such as an FET or an EL can be formed.

[0014] If the molecular weight of the resin is too large, the resin is eluted in the above-mentioned organic solvent even in a region where light has not been irradiated (cis-poly (arylene bilene)), and the resin is not dissolved. If the molecular weight is too small, the resin will be easily eluted into the organic solvent even in the light-irradiated region (trans-poly (arylene bi-lene)), so the resin should have a number average molecular weight of 1500 to 30,000.

[0015] Further, when trans-poly (arylene vinylene) is abundant in the resin before light irradiation, the resin film is not sufficiently eluted in the organic solvent in the light non-irradiated region. Therefore, the ratio of cis-poly (arylene vinylene) to trans-poly (arylene vinylene) should be 65/35 or more.

The invention's effect

[0016] By using the conductive resin of the present invention, it is possible to perform patterning without using a resist. For this reason, it is possible to improve the production efficiency and the yield of products such as organic EL, organic FET, battery, and capacitor manufactured using the conductive resin of the present invention. In addition, since it is not necessary to develop the resist, the amount of the organic solvent used can be reduced, and the burden on the environment can be reduced.

Brief Description of Drawings

[FIG. 1] A daraf showing the time-dependent change of ultraviolet-visible absorption spectrum of ds_PPV solution due to light irradiation.

FIG. 2 is a graph showing a time-dependent change in an ultraviolet-visible absorption spectrum of a ds_PPV film due to light irradiation. [FIG. 3] 1H NMR ^ vector of PPV synthesized by the method of reaction formula (1).

[Figure 4] (a) Optical micrograph of PPV film with line pattern, (b) with dot pattern

Optical micrograph of the PPV film.

BEST MODE FOR CARRYING OUT THE INVENTION

The poly (arylene bilen) used in the present invention has the general formula (1)

[Chemical 1]

… General formula (1)

(Ar and Ar ′ are the same or different arylene groups or heterocyclic compound groups, and n is an integer of 1 or more).

The structure of Ar and Ar 'is not particularly limited as long as it is an arylene group or a heterocyclic compound group. Examples of the structure of Ar and Ar' include, for example, the formula (1), the chemical formula (17), These derivatives can be mentioned.

[Chemical 2]

Chemical formula (1) Chemical formula (2) Chemical formula (3) Chemical formula (4)

Chemical formula (8) Chemical formula (9) Chemical formula (10) Chemical formula (11) Chemical formula (12) Chemical formula (13)

Chemical formula (14) Chemical formula (15) Chemical formula (16) Chemical formula (17)

(M is one of Mn, Re, Fe, Ru, 0s, Co, Rh, Ir, Ni, Pd, Pt, Pt, Zn, Mg, and Al) Here, chemical formula (1) is combined with chemical formula (17) The positional relationship between the two vinyl groups (described in the general formula (1)) on the aromatic ring or the heterocyclic ring is not particularly limited. For example, when Ar or Ar ′ is benzene, the two butyl groups may have any of ortho, meta and para positional relationships. In addition, the derivative of the chemical formula (1) -the chemical formula (17) means an alkyl group, an aryl group, an alkoxy group, a carbonyl group, an amino group, a nitro group, etc. on these aromatic rings or complex rings instead of hydrogen atoms. Means that the substituent is bonded.

For example, ds-poly (arylene vinylene) represented by the chemical formula (18) (number average molecular weight

Mn = 2700, (polydispersity) = (weight average molecular weight) / (number average molecular weight) = 1.79 (polystyrene standard), cis / trans ≥99 / l) 0.015mg / mL benzene solution has an ultraviolet-visible absorption spectrum As shown in Fig. 1, by irradiating with a high-pressure xenon lamp (main wavelength: 360 nm), cis-poly (arylene bi-len) isomerized over time, and In 150 seconds, the ds health has completely changed to the trans body. This measurement was performed at 23 ° C. in a nitrogen atmosphere with the distance between the sample and the light source being 20 cm and the illuminance being about 0.4 mW / cm ² . [Formula 3] Chemical formula (18)

FIG. 2 shows cis-poly (arylene vinylene) represented by the chemical formula (18) (number average molecular weight

Mn = 6900, (polydispersity) = 2.01 (based on polystyrene), shows the time-dependent UV-visible absorption spectrum of the film (100-200 nm thickness) produced by light irradiation. It is a graph. This measurement was performed at 23 ° C. in a nitrogen atmosphere with the distance between the sample and the light source being 5 cm and the illuminance being 260 mW / cm ² . Due to the high concentration of poly (arylene bi-len), the light irradiation time is longer than in the solution state, and the shape of the force sturtle whose spectrum is broad is the same as that in FIG.

This shows that cis-poly (arylene vinylene) changes to trans-poly (arylene vinylene) by light irradiation even in a solid (film) state.

[0021] In the present invention, the property that the solubility in a solvent varies depending on the poly (arylene vinylene) force steric structure is used for puttering, so that cis-poly (arylene vinylene) can be used with high stereoselectivity. It is important to be able to obtain.

[0022] Therefore, the present inventors have intensively studied a method for obtaining cis-poly (arylene bi-lene) with high and stereoselectivity.

As a result, the first aromatic compound or heterocyclic compound having two cis-promothenyl groups bonded thereto and the second aromatic compound or heterocyclic compound having one equivalent of two boronic acids bonded to the first arylene conjugate or heterocyclic compound. The arylene conjugate or heterocyclic compound is dissolved in an organic solvent, and then, with respect to the first or second arylene conjugate or the heterocyclic compound, 115 equivalents of a base and the first or second After adding 0.1 to 10 mol% of a palladium catalyst to the arylene conjugate or the heterocyclic compound, the mixture is heated and stirred at 40 to 120 ° C under light-shielding conditions. 99% or more of cis-poly (arylene vinylene) depending on the reaction used t, u high! , And stereoselectivity.

Reaction equation (1) specifically illustrates this reaction.

[Formula 4]

In this reaction, as the base, sodium hydroxide, potassium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, potassium phosphate, silver oxide, or an aqueous solution thereof can be used. . Further, as the noradium catalyst, tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium, dichloro {1,1bis (diphenylphosphine) phenacene} palladium and the like can be used.

The ¹ H NMR (300 MHz, CDCl 3) scan of the poly (arylene biene) synthesized by this reaction

Figure 3 shows the three vectors. The peak of hydrogen bonded to the carbon adjacent to the oxygen of the alkoxy group (bonded to the benzene ring) appears at 3.5 ppm for cis-poly (arylene bi-len) and 4.1 ppm for trans-poly (arylene bi-len) Power Figure 3 shows no peak at 4.1 ppm. From this, it is understood that according to the above method, cis-poly (arylene vinylene) power can be obtained with high stereoselectivity.

[0024] The inventors of the present invention have found that a reaction using the Hiyama cross-coupling type polycondensation method represented by the reaction formula (2) gives a stereoselection of cis-poly (arylene vinylene) of 66% or more. We have already reported what we can obtain by sex ("Journal of Organometallic Chemistry"), (USA), 2003, Vol. 676, pp.49-54) .

[Formula 5]

… Reaction formula (2)

[0025] In a region where the trans body is contained in a relatively large amount, the resin does not dissolve in the solvent and remains as it is even when light is not irradiated. In particular, when performing fine pattern junging on the order of several nanometers, it is easy to lead to defects such as the connection of adjacent wirings. Therefore, a reaction formula () that can obtain cis poly (arylene bilene) with high selectivity ( The resin must be synthesized by the method of 1). However, when only a relatively rough pattern is to be produced, it is also possible to use a resin obtained by the reaction formula (2) or another method.

[0026] The conductive resin of the present invention is modified by changing the substituent on the aromatic ring or the heterocyclic ring of arylene bilen so as to have properties according to the use such as organic EL, organic FET, battery, and capacitor. be able to. Also, depending on the purpose of improving the conductivity of the material, for example, halogens such as I and Br, alkali metals such as Na and Ka, sulfonic acids such as p-toluenesulfonic acid

twenty two

It is also possible to mix impurities such as dopants and other compounds into the resin.

[0027] In the above description, the poly (arylene vinylene) is preliminarily formed into a cube or the like after the poly (arylene vinylene) is formed into a film and the patterning of a circuit or the like is performed. By performing elution with a solvent on the light-irradiated and non-light-irradiated portions in the same manner as described above, it is also possible to produce a molded article such as an object.

Example

(0028) (Synthesis of cis-PPV (1))

1,4-bis (cis-2-bromoethyl) benzene (58 mg, 0.20 mmol), 1,4-dioctyloxy-2,5-benzenediboronic acid (86 mg, 0.20 mmol), tetrabutylammonium bromide

(65 mg, 0.20 mmol) in toluene solution (2.0 mL), 3M potassium phosphate aqueous solution

(0.2 mL, 0.6 mmol) and tetrakis (triphenylphosphine) palladium

(0.23 mg, 0.20 mmol) was stirred and stirred at 80 ° C. for 24 hours under light-shielded conditions. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. This resulted in cis-PPV as a dark orange solid (87 mg, 94% yield).

This solid was dissolved in CDC1 and ^ NMR was measured.

Three

It was confirmed that the ratio was 99/1 or more. GPC analysis revealed a number average molecular weight of 7,200 and a polydispersity of 2.89 (based on polystyrene). [0029] (Synthesis of cis-PPV (2))

(0.2 mL, 0.6 mmol) and tetrakis (tripheninolephosphine) palladium (2.3 mg, 2.0 mmol) were added, and the mixture was stirred at 80 ° C for 24 hours under light-shielded conditions. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, cis-PPV was obtained as a dark orange solid (97 mg, yield 99% or more).

This solid was dissolved in CDC1 and ^ NMR was measured.

Three

It was confirmed that the ratio was 99/1 or more. Further, as a result of analysis by GPC, the number average molecular weight was 3,300 and the polydispersity was 1.53 (based on polystyrene).

[0030] (Synthesis of cis-PmPV)

1,3-bis (cis-2-bromoethyl) benzene (58 mg, 0.20 mmol), 1,4-dioctyloxy-2,5-benzenediboronic acid (87 mg, 0.21 mmol), tetrabutylammonium bromide

To a toluene solution (2.0 mL) of (65 mg, 0.20 mmol) was added a 3M aqueous solution of potassium hydroxide (0.2 mL, 0.6 mmol) and tetrakis (tripheninolephosphine) palladium (2.3 mg, 2.0 mmol), and the mixture was protected from light. Under the conditions, the mixture was stirred at 80 ° C for 24 hours. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, ds-PmPV represented by the chemical formula (19) was obtained as a brown viscous solid (80 mg, yield 86%).

[Formula 6] Chemical formula (19)

This solid was dissolved in CDC1 and 1 H NMR was measured.

Three

It was confirmed that the ratio of trans-PmPV was 99/1 or more. GPC analysis revealed a number average molecular weight of 5,100 and a polydispersity of 2.13 (based on polystyrene).

[0031] (Synthesis of cis-PFVPV)

2,7-bis (cis-2-bromoethyl) -9,9-dihexylfluorene (59 mg, 0.11 mmol), 1,4-dioctyloxy-2,5-benzenediboronic acid (47 mg, 0.11 mmol), odor 3M potassium phosphate aqueous solution in toluene solution (l.OmL) of tetrabutylammonium bromide (35mg, 0.11mmol)

(0.1 mL, 0.3 mmol) and tetrakis (triphenylphosphine) palladium

(0.13 mg, 0.11 mmol) was stirred and stirred at 80 ° C. for 24 hours under light-shielded conditions. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, cis-PFVPV represented by the chemical formula (20) was obtained as a brown solid (75 mg, yield: 96%).

This solid was dissolved in CDC1 and ^ NMR was measured to find cis-PFVPV

Three

The specific power of trans-PFVPV was confirmed to be 72/28. As a result of analysis by GPC, the number average molecular weight was 3,700 and the polydispersity was 1.46 (based on polystyrene).

[Formula 7]

Chemical formula (20)

(0032) (Synthesis of cis-PFPV)

2,7-bis (cis-2-bromoethyl) fluorene (103mg, 0.273mmol), 1,4-dioxy- 2,5-benzenediboronic acid (131mg, 0.273mmol), tetrabutylammonium-bromo bromide (79 mg, 0.27 mmol) in a toluene solution (1.2 mL) was heated with a 3M aqueous solution of potassium hydroxide (0.24 mL, 0.72 mmol) and tetrakis (triphenylphosphine) palladium (3.1 mg, 2.6 μmol). The mixture was stirred at 80 ° C for 24 hours under light shielding conditions. After cooling the reaction solution to room temperature, Poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, ds-PFPV represented by the chemical formula (21) was obtained as a dark orange solid (135 mg, yield: 90%).

When this solid was dissolved in CDC1 and 1H NMR was measured, cis-PFPV and trans-PFPV

Three

It was confirmed that the specific force was S90 / 10. As a result of analysis by GPC, the number average molecular weight was 7,400 and the polydispersity was 2.42 (based on polystyrene).

[Formula 8]

Chemical formula (21)

(Synthesis of cis-MEH-PPV)

1,4-bis (cis-2-bromoethyl) benzene (79 mg, 0.27 mmol), 1- (2-ethylhexyloxy) -4-methoxy-2,5-benzenediboronic acid (87 mg, 0.27 mmol), To a toluene solution of tetrabutylammonium bromide (79 mg, 0.27 mmol) (1.2 mL) was added a 3M aqueous solution of potassium hydroxide (0.24 mL, 0.72 mmol) and palladium tetrakis (triphenylphosphine) (3.1 mg, 2.6 mg). μmol) and stirred at 80 ° C. for 24 hours under light-shielded conditions. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, cis-MEH-PPV represented by the chemical formula (22) was obtained as a dark orange solid (66 mg, yield 68%).

This solid was dissolved in CDC1 and ^ NMR was measured to find cis-MEH-PPV.

Three

It was confirmed that the ratio of trans-MEH-PPV was 99/1 or more. GPC analysis revealed a number average molecular weight of 6,400 and a polydispersity of 2.36 (based on polystyrene).

[Formula 9] Chemical formula (22)

[0034] (Synthesis of cis-[(S) -BMB] PPV)

1,4-bis (cis-2-bromoethyl) benzene (126 mg, 0.437 mmol), 1,4-bis [(S) -2-methylbutoxy] -2,5-benzenediboronic acid (149 mg, 0.437 mmol ), Tetrabutylammonium bromide (141 mg, 0.437 mmol) in toluene (4.4 mL), 3M aqueous potassium phosphate (0.44 mL, 1.3 mmol) and tetrakis (triphenylphosphine) palladium (0.51 mg, 0.44 mol) and stirred at 80 ° C for 24 hours under light-shielded conditions. After the reaction solution was cooled to room temperature, it was poured into stirred methanol (50 mL). The resulting precipitate was filtered and the precipitate was washed with methanol. As a result, ds-[(S) -BMB] PPV represented by the chemical formula (23) was obtained as an ocher solid (159 mg, 97% yield).

When this solid was dissolved in CDC1 and 1H NMR was measured, cis-[(S) -BMB] PPV and

Three

It was confirmed that the ratio of trans-[(S) -BMB] PPV was 99/1 or more. Analysis by GPC showed that the number average molecular weight was 2,900 and the polydispersity was 1.60 (based on polystyrene).

[Formula 10] Chemical formula (23)

[0035] These poly (arylene vinylenes) can emit light by applying a voltage. The emission wavelength at that time is 510 nm for PPV, 450 nm for PmPV, 499 nm for PFVPV, and 488 nm for PFPV.

[0036] (Patterning experiment) The cis-PPV obtained in the above (Synthesis of cis-PPV (2)) was used as a 15 wt% solution in a form of black mouth, dropped several drops on a quartz glass substrate (lcm X lcm X 0.5 mm), and then 800 rpm. After spin-casting at 2000 rpm for 60 seconds, a cis-PPV film having a thickness of 100 to 200 nm was obtained. The substrate thus obtained was vacuum-dried at room temperature for 30 minutes, and then a photomask was placed on the film and placed in a cell with a quartz window.

After purging the inside of the cell with nitrogen gas, ultraviolet light (main wavelength: 365 nm, illuminance: 260 mW / cm ² ) was irradiated by a high-pressure xenon lamp for 30 minutes. Thereafter, the substrate was taken out, and the film was immediately washed with a black hole form.

FIG. 4 shows an optical microscope photograph of the film obtained as described above. As can be seen from Fig. 4, when the conductive resin of the present invention is used, a line pattern with a line width of 50 m or less (Fig. 4 (a)) and a dot pattern with a diameter of 50 m or less (Fig. (b)) can be formed.

[0038] Incidentally, although this embodiment the intensity of ultraviolet light and 260 mW / cm ^2, forming a pattern which more weaklyヽultraviolet light strength degree of (for example 35 mW / cm ²⁾ even in the conductive榭脂of the present invention It is possible to do.

Claims

The scope of the claims

[1] Poly (arylene vinylene) with a ratio of cis-poly (arylene vinylene) to trans-poly (arylene vinylene) of 65/35 or more and a number average molecular weight of 1500-30000 The linear resin includes a heterocyclic compound group in addition to an arylene group.) A photo-patternable conductive resin.

[2] The arylene of poly (arylene bi-len) (where arylene includes a heterocyclic compound group in addition to the arylene group) has the chemical formula (1)-(17)

[Formula 11] Chemical formula (1) Chemical formula (2) Chemical formula (3) Chemical formula (4)

(M is any of Mn, Re, Fe, Ru, 0s, Co, Rh, Ir, Ni, Pd, Pt, Pt, Zn, Mg, Al) or a derivative of these The conductive resin capable of photo-patterning according to claim 1, characterized by:! /.

After irradiating a predetermined area of the resin film containing cis-poly (arylene vinylene) with light of 200 to 600 nm, the non-irradiated portion is irradiated with an aromatic, halogen or ether organic solvent. Patterning the membrane by eluting it with the organic solvent. A method for producing a conductive resin film having a fixed pattern.

[4] The predetermined pattern according to [3], wherein the aromatic, halogen, or ether organic solvent power is any one of benzene, toluene, chloroform, methylene chloride, and tetrahydrofuran. A method for producing a conductive resin film.

[5] The first arylene conjugate or heterocyclic compound to which two cis-promothenyl groups are bonded, and one equivalent of two boronic acids to the first arylene conjugate or heterocyclic compound are bonded. The second arylene conjugate or heterocyclic compound is dissolved in an organic solvent, and the first or second arylene conjugate or the heterocyclic compound is mixed with 115 equivalents of the base or the first or second arylene conjugate or heterocyclic compound. After adding 0.1 to 10 mol% of a palladium catalyst to the second arylene compound or heterocyclic compound, the mixture is heated and stirred at 40 to 120 ° C. under light-shielding conditions to form a first arylene compound or heterocyclic compound. A method for producing poly (arylene bilen), comprising reacting a second arylene conjugate or a heterocyclic compound.

[6] The base is characterized in that it is any one of sodium hydroxide, potassium hydroxide, barium hydroxide, potassium carbonate, sodium carbonate, potassium phosphate, silver oxide, or an aqueous solution thereof. A method for producing the poly (arylene vinylene) according to claim 5.

[7] The palladium catalyst is selected from the group consisting of tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium, and dichloro {1,1′-bis (diphenylphosphine) ferrocene} palladium. 7. The method for producing poly (arylene vinylene) according to claim 5, wherein the method is characterized in that:

[8] Poly (arylene vinylene) resin whose ratio of cis-poly (arylene vinylene) to trans-poly (arylene vinylene) is 65/35 or more, and whose number average molecular weight is 1500-30000 Wherein the arylene includes a heterocyclic compound group in addition to the arylene group.)