JP2010155791A - Condensed polycyclic aromatic compound, method for producing the same, and copolymer of condensed polycyclic aromatic compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new condensed polycyclic aromatic compound. <P>SOLUTION: The condensed polycyclic aromatic compound is represented by formula (1) (wherein, R<SP>1</SP>to R<SP>12</SP>are each independently one kind selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, oligoaryl, substituted oligoaryl, heterocycle, substituted heterocycle, alkoxy, substituted alkoxy, alkylthio, substituted alkylthio, nitro, amino, substituted amino, silyl, substituted silyl, alkylsulfonyloxy and the like; and n is an integer of 1-100). <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a novel condensed polycyclic aromatic compound, a process for producing the same, and a copolymer of the condensed polycyclic aromatic compound.

  In recent years, organic thin film transistors and organic electroluminescent devices have been actively studied because they can save power, be light, and can be thin. In particular, the development of organic compounds having charge transporting ability (having the possibility of becoming a semiconductor or a superconductor) such as holes and electrons has been actively studied regardless of whether they are high molecular compounds or low molecular compounds.

As a molecular design of such an organic compound, it is considered that one of the effective methods is to construct a molecule having a high planarity and a π-conjugated skeleton. For example, condensed polycyclic aromatic compounds such as anthracene and pentacene are known to exhibit high charge mobility due to a dense packing structure (for example, see Non-Patent Documents 1 and 2). In addition, chrysene derivatives (Non-patent Document 3) have been actively studied.
MD Watson, A. Fechtenkotter, K. Mullen, Chem. Rev. 2001, 101, 1267. JE Anthony, Chem. Rev. 2006, 106, 5028 S. Yamaguchi, TM Swager, J. Am. Chem. Soc. 2001, 123, 12087.

  When a π-conjugated compound is put into practical use as a semiconductor material, a material having high charge (carrier) mobility or a material that can be easily injected with carrier is required as its characteristics. However, the present situation is that π-conjugated compounds satisfying these requirements are extremely limited, and the development of new materials having truly excellent characteristics has been desired.

  In addition, the synthesis of condensed polycyclic compounds as shown in Non-Patent Documents 1, 2, and 3 generally requires a multi-step process. In addition, severe reaction conditions are often required, and synthesis of compounds having a functional group or a heterocyclic ring is limited. For the above-mentioned application, the development of a short process, a simple and highly versatile synthesis method has been an important issue.

  This invention is made | formed in view of the subject mentioned above, and aims at providing the copolymer of a novel condensed polycyclic aromatic compound, its manufacturing method, and a condensed polycyclic aromatic compound.

  As a result of examining the above problems, the present inventors have newly found a condensed polycyclic aromatic compound having a structure represented by the following formula (1) or the following formula (2) and a method for producing the same. As a result of analyzing the crystal structure, it was found that it has a highly planar molecular structure and a dense packing structure that is advantageous for high charge mobility, and the present invention has been completed.

  That is, the condensed polycyclic aromatic compound of the present invention is represented by the following formula (1) or the following formula (2).

(In formula (1), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group 1 is selected, and n is an integer of 1 to 100)

(In formula (2), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group 1 is selected, and n is an integer of 1 to 100)
The method for producing the condensed polycyclic aromatic compound of the present invention includes:
In the following formula (12), a compound having a thienyl or substituted thienyl group at the 2,2′-position of a diarylacetylene compound represented by the following formula (11) is irradiated with light to carry out an intramolecular double cyclization reaction. It is set as the condensed polycyclic aromatic compound represented.

The method for producing the condensed polycyclic aromatic compound of the present invention includes:
In the following formula (14), a compound having a thienyl or substituted thienyl group at the 2,2′-position of a diarylacetylene compound represented by the following formula (13) is irradiated with light to carry out an intramolecular double cyclization reaction. It is set as the condensed polycyclic aromatic compound represented.

(In the formulas (13) and (3), R ^{1 to} R ¹² are each independently a hydrogen atom, alkyl group, substituted alkyl group, aryl group, substituted aryl group, oligoaryl group, substituted oligoaryl group, complex, Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)

(In the formulas (13) and (14), R ^{1 to} R ¹² each independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)

According to the condensed polycyclic aromatic compound of the present invention, it is possible to obtain an effect of taking a dense packing structure in a solid state, which is essential for high charge mobility.
Moreover, according to the method for producing a condensed polycyclic aromatic compound of the present invention, the condensed polycyclic aromatic compound of the present invention can be obtained in a short process and in a relatively high yield.

Examples of the alkyl group usable as R ^{1 to} R ^{12 in the} present invention include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. In addition to an alkyl group that may be branched, a cyclic alkyl group such as a cyclopentyl group or a cyclohexyl group may be used. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a pyrenyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group.

  Examples of the alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, a sec-butylthio group, and a tert-butylthio group. In addition, examples of the heterocyclic group include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a benzothienyl group, and a quinolyl group. Examples of the leaving group include a sulfonyloxy group and a halogen atom. Examples of the sulfonyloxy group include a mesylate group, a tosylate group, and a triflate group. Examples of the halogen atom include a fluorine atom, a chlorine atom, A bromine atom, an iodine atom, etc. are mentioned. In addition, specific substituents having a “substituted” prefix such as substituted alkyl groups include, for example, halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group , N-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group and other alkyl groups that may be branched; cyclopentyl group, cyclohexyl group and other cyclic alkyl groups; vinyl group Alkenyl groups such as ethynyl group, propargyl group and phenylacetinyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec -Alkoxy groups such as butoxy group and tert-butoxy group; vinyl groups such as vinyloxy group and allyloxy group Alkenyloxy groups such as ethynyloxy groups and phenylacetyloxy groups; aryloxy groups such as phenoxy groups, naphthoxy groups, biphenyloxy groups, and pyrenyloxy groups; trifluoromethyl groups, trifluoromethoxy groups, pentafluoroethoxy groups, etc. Perfluoro groups and further long-chain perfluoro groups; amino groups such as dimethylamino group, diethylamino group, diphenylamino group, carbazolyl group; boryl groups such as diphenylboryl group, dimesitylboryl group, bis (perfluorophenyl) boryl group A carbonyl group such as an acetyl group or a benzoyl group; a carbonyloxy group such as an acetoxy group or a benzoyloxy group; an alkoxycarbon group such as a methoxycarbonyl group, an ethoxycarbonyl group, or a phenoxycarbonyl group; Groups: sulfinyl groups such as methylsulfinyl group and phenylsulfinyl group; silyl groups such as trimethylsilyl group, triisopropylsilyl group, dimethyl-tert-butylsilyl group, trimethoxysilyl group, triphenylsilyl group; phenyl group, 2,6- Xylyl, mesityl, duryl, biphenyl, terphenyl, naphthyl, anthryl, pyrenyl, toluyl, anisyl, fluorophenyl, diphenylaminophenyl, dimethylaminophenyl, diethylaminophenyl, phenanthrenyl Aryl groups such as thienyl group, furyl group, silacyclopentadienyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, acridinyl group, quinolyl group, quinoxaloyl group, phenane Examples thereof include heterocyclic groups such as a thrylyl group, a benzothienyl group, a benzothiazolyl group, an indolyl group, a carbazolyl group, a pyridyl group, a pyrrolyl group, a benzoxazolyl group, a pyrimidyl group, and an imidazolyl group. In addition, a nitro group, a formyl group, a nitroso group, a formyloxy group, an isocyano group, a cyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a cyano group, and the like can be given. Furthermore, these substituents may be bonded to each other at any position to form a ring.

  The condensed polycyclic aromatic compound of the present invention further includes a compound represented by the following formula (3) or (4), and the following formulas (5), (6), (7), (8). , (9) and a copolymer of a condensed polycyclic aromatic compound having a compound represented by at least one selected from the group consisting of (10) as a repeating unit.

(In formula (3), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group One of the chosen types,
n is an integer of 1 to 100)
(In Formula (4), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group One of the chosen types,
n is an integer of 1 to 100)

(In the formulas (5) to (10), Ar ^{1 to} Ar ⁶ each independently represent an arylene group, a divalent heterocyclic group, or a divalent group having a metal complex structure, and Y ^{1 to} Y ⁵ are each ^{independently, -CR 13 = CR 14 -,} - C≡C -, - N (R 15) -, - B (R 16) -, or _{^{- (SiR 17 R 18) q}} - indicates, R ¹³ and R ¹⁴ each independently represents a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group, and R ^{15 to} R ¹⁸ each independently represents a hydrogen atom. An atom, an alkyl group, an aryl group, a monovalent heterocyclic group or an arylalkyl group, and o, p and q each independently represents an integer of 1 to 12)
In the condensed polycyclic aromatic compound represented by the above formula (1) or the above formula (2) of the present invention, n may be 1, but n is 2 or more, preferably n is 10 or more. It is good. In order to produce such a polymer, it can be synthesized with reference to J. Am. Chem. Soc., 2008, vol.130, pp7670-7685. An example is shown in the following chemical formula 7. In this example, NBS is added to a THF solution of 3,9-dioctyloxydithieno [2,3-g: 2 ′, 3′-p] chrysene (see formula (15)) to obtain a dibromo compound (formula (See (16)). On the other hand, a trimethylstannyl group is introduced by dropping a hexane solution of n-BuLi into a THF solution of the compound represented by the formula (15) and then adding trimethyltin chloride (Me ₃ SnCl). The compound represented by the formula (17) is obtained. Then, the compound represented by the formula (16), the compound represented by the formula (17), and Pd (PPh ₃ ) ₂ Cl ₂ are mixed in anhydrous THF and heated to reflux, and then added to methanol for reaction. By extracting the product, a polymer (see formula (18)) can be obtained.

  (i) Among the methods for producing the compound of formula (18), by changing the raw material of the formula (15) to the compound (11), other compounds of the formula (1) can also be produced. Moreover, the compound of Formula (2) is also producible by changing the part of Formula (15) which is a raw material into the compound (13) among the manufacturing methods of the compound of (18).

  (ii) The above change (i) can be easily made.

The copolymer of the condensed polycyclic aromatic compound represented by the above formula (3) or the above formula (4) of the present invention is synthesized with reference to Synthetic Metals, 2005, vol.127, pp251-254. Can do. An example is shown in the following chemical formula 8. A compound represented by the formula (17), 2,2′-bis (pinacolatoboryl) -9,9-dioctylfluorene (compound 19), Pd (PPh ₃ ) ₄ , and an aqueous potassium carbonate solution were mixed in THF. After heating and refluxing, the reaction mixture is dissolved in a small amount of chloroform and poured into methanol, and the precipitate is purified to obtain a copolymer (see formula (20)).

Next, an example of a synthetic route for the condensed polycyclic aromatic compound represented by the above formula (12) or (14) of the present invention is shown in the following chemical formulas 5 and 6. Since R ^{1 and the} like of Chemical Formula 5 and Chemical Formula 6 are as already described, the description thereof is omitted here. The condensed polycyclic aromatic compound represented by the above formula (3) of the present invention is a molecule of a compound having a thienyl or substituted thienyl group at the 2,2 ′ position of a diarylacetylene compound represented by the following formula (11) It can be synthesized by advancing the internal double cyclization reaction.

  In addition, the condensed polycyclic aromatic compound represented by the above formula (14) of the present invention is a compound having a thienyl or substituted thienyl group at the 2,2 ′ position of the diarylacetylene compound represented by the following formula (13): Can be synthesized by advancing the intramolecular double cyclization reaction.

  The reaction conditions such as reaction solvent, reaction temperature, reaction time, and molar concentration of the reagent may be appropriately set according to the reagent used.

  The condensed polycyclic aromatic compound represented by the formula (3) corresponds to the case where n is 1 in the formula (1), and the condensed polycyclic aromatic compound represented by the formula (4) This corresponds to the case where n is 1 in 2), but the synthesis example in the case where n is 2 or more is as already described.

(In formulas (11) and (12), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)

(In the formulas (13) and (14), R ^{1 to} R ¹² each independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)
Hereinafter, the present invention will be specifically described with reference to examples.

For the following examples, the melting point (mp) was measured using Yanaco YanacoMP-S3. ¹ HNMR was measured using JEOL AL-400 or GSX-270. Mass spectrometry was measured using a Shimadzu GCMS QP2010. The reaction was performed using a dehydrated solvent in argon. The THF used for the reaction was a commercially available dehydrated solvent (Kanto). Thin layer chromatography (TLC) was performed using silica gel 60F ₂₅₄ (Merck). For silica gel column chromatography, PSQ100B (Fuji Silysia) was used. Recycle preparative reverse phase HPLC was performed using LC-9201 (Nippon Analytical Industries) equipped with Wakosil-II 5C18HG Prep (Wako). A high pressure UV lamp (Ushio) was used for light irradiation.

(1) Synthesis of 3,9-dimethoxydithieno [2,3-g: 2 ′, 3′-p] chrysene (Compound 21) (see Chemical Formula 10)
In a dry argon atmosphere, in a Pyrex® test tube with a screw cap, bis {5-methoxy-2- (3′-thienyl) phenyl} acetylene (Compound 22) (121 mg, 0.30 mmol) and iodine (152 mg) , 0.60 mmol) in THF (1.5 mL) was prepared, sealed, and irradiated with a high-pressure UV lamp at room temperature for 6 hours. Saturated aqueous sodium sulfite was added to the reaction mixture to decompose excess iodine, and the mixture was separated into two layers and extracted with chloroform. The obtained organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off. A mixture of compound 21 and compound 23 was taken out from the obtained crude product by silica gel column chromatography (Rf = 0.46, elution solvent: hexane / chloroform = 1/1), and this was further subjected to recycle preparative reverse phase HPLC. (Elution solvent: acetonitrile / THF = 2/1) to obtain compound 21 and compound 23 (compound 21: yield 15%; compound 23: yield 8 as a mixture of isomers 23a and 23b) .9%).

The spectral data of Compound 21 are as follows: ¹ H NMR (400 MHz, CDCl ₃ ) δ4.13 (s, 6H), 7.41 (dd, 2H, J = 2.4 Hz, 8.8 Hz), 7.68 (d, 2H, J = 5.2 Hz), 8.07 (d, 2H, J = 5.6 Hz), 8.42 (d, 2H, J = 8.8 Hz), 8.79 (d, 2H, J = 2.4 Hz); MS (EI) m / z = 400 (M ⁺ ).
The spectral data of compound 23 are as follows (mixture of two isomers 23a / 23b = 1/1): ¹ H NMR (400 MHz, CDCl ₃ ) δ 4.04 (s, 6H), 4.12 (s, 6H) , 7.374 (dd, 2H, J = 4.4 Hz, 8.8 Hz) 7.375 (d, 2H, J = 8.8 Hz), 7.58 (d, 2H, J = 5.6 Hz), 7.69 (d, 2H, J = 5.6 Hz) , 8.08 (d, 2H, J = 5.6 Hz), 8.24 (d, 2H, H = 8.8 Hz), 8.39-8.44 (m, overlapped, 6H), 8.74 (d, 2H, J = 2.4 Hz).
(2) X-ray crystal structure analysis The single crystal of compound 21 used for X-ray crystal structure analysis was obtained by a two-layer diffusion method of chloroform-hexane. Intensity data was measured using a Rigaku single crystal CCD X-ray analyzer (Saturn 70 with MicroMax-007, MoKα irradiation (λ = 0.71070 mm, graphite monochromator). -Squares on F2 (SHELXS-97), atoms other than hydrogen were anisotropically optimized and hydrogen atoms were placed using the AFIX instruction, Figure 1 shows the crystal structure of compound 21, Figure 2 1 shows the packing structure in the crystal of compound 21. In FIG. 1, C1 to C12 and C1 ^{* to} C12 ^* are carbon atoms, O1 and O1 ^* are oxygen atoms, S1 and S1 ^* are sulfur atoms, and white circles are hydrogen atoms. Represents an atom in FIG. The arrows represent the direction and type of the crystal axis.

  From this, it is clear that Compound 21 has a strong and highly planar π-conjugated skeleton. In the crystal, compound 21 has a herringbone structure in which the conjugated surfaces have a two-dimensional network between molecules, and the closest interatomic distance between the two molecules closest to each other was 3.451 angstroms. .

It should be noted that the present invention is not limited to the above-described embodiment, and it goes without saying that the present invention can be implemented in various modes as long as it belongs to the technical scope of the present invention.

  The condensed polycyclic aromatic compound of the present invention has a structure in which molecules are closely packed in a crystal. It is often reported that such a structure is an important element for expressing high charge mobility. Utilizing such structural characteristics, it can be used for an organic semiconductor material or the like by using a vapor deposition film or a coating film.

6 is an explanatory diagram of the X-ray crystallographic analysis result of Compound 21. 3 is an explanatory diagram of a packing structure obtained by X-ray crystallography of compound 21. FIG. The dashed line shows the distance between the nearest atoms between the two closest molecules.

Claims (9)

A condensed polycyclic aromatic compound represented by the following formula (1).
(In formula (1), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group One of the chosen types,
n is an integer of 1 to 100) A condensed polycyclic aromatic compound represented by the following formula (2).
(In formula (2), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a heterocyclic group, or a substituted group. Heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl group, formyl group A stannyl group, a substituted stannyl group, an imino group, a substituted imino group, a boryl group, a substituted boryl group, a phosphino group, a substituted phosphino group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, and an alkylsulfonyloxy group One of the chosen types,
n is an integer of 1 to 100)   2. The condensed polycyclic aromatic compound according to claim 1, wherein n is 1.   The condensed polycyclic aromatic compound according to claim 2, wherein n is 1. The compound represented by the following formula (3) or (4) and further selected from the group consisting of the following formulas (5), (6), (7), (8), (9) and (10) A copolymer of a condensed polycyclic aromatic compound having at least one compound represented by
(In formulas (3) and (4), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 is selected from the group consisting of: n is an integer of 1 to 100)
(In the formulas (5) to (10), Ar ^{1 to} Ar ⁶ each independently represent an arylene group, a divalent heterocyclic group, or a divalent group having a metal complex structure, and Y ^{1 to} Y ⁵ are each ^{independently, -CR 13 = CR 14 -,} - C≡C -, - N (R 15) -, - B (R 16) -, or _{^{- (SiR 17 R 18) q}} - indicates, R ¹³ and R ¹⁴ each independently represents a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group, and R ^{15 to} R ¹⁸ each independently represents a hydrogen atom. An atom, an alkyl group, an aryl group, a monovalent heterocyclic group or an arylalkyl group, and o, p and q each independently represents an integer of 1 to 12)
  The condensed polycyclic aromatic compound according to any one of claims 1 to 4, which is used as an organic semiconductor material.   The copolymer of the condensed polycyclic aromatic compound according to claim 5, which is used as an organic semiconductor material. A compound having a thienyl or substituted thienyl group at the 2,2′-position of a diarylacetylene compound represented by the following formula (11) is irradiated with light to carry out an intramolecular double cyclization reaction, whereby the following formula (12) A process for producing a condensed polycyclic aromatic compound represented by the formula:
(In formulas (11) and (12), R ^{1 to} R ¹² are each independently a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)
The compound represented by the following formula (13) having a thienyl or substituted thienyl group at the 2,2′-position of the diarylacetylene compound is irradiated with light to carry out an intramolecular double cyclization reaction, whereby the following formula (14) A process for producing a condensed polycyclic aromatic compound represented by the formula:
(In the formulas (13) and (14), R ^{1 to} R ¹² each independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a complex Ring group, substituted heterocyclic group, alkoxy group, substituted alkoxy group, alkylthio group, substituted alkylthio group, nitro group, amino group, substituted amino group, silyl group, substituted silyl group, cyano group, halogen atom, carbamoyl group, substituted carbamoyl Group, formyl group, stannyl group, substituted stannyl group, imino group, substituted imino group, boryl group, substituted boryl group, phosphino group, substituted phosphino group, silyloxy group, substituted silyloxy group, arylsulfonyloxy group, and alkylsulfonyloxy group 1 type selected from the group consisting of)