Material for photoelectric conversion element, organic thin film, photoelectric conversion element, and fused ring compound

Abstract

The present invention provides: a material for a photoelectric conversion element, the material contributing to the production of the photoelectric conversion element that has low dark current, high external quantum efficiency, and excellent responsiveness; and the like.　The present invention uses a material for a photoelectric conversion element, the material containing a fused ring compound that is represented by formula (1). In formula (1), a ring A represents a structure represented by formula (2); and R1 to R8 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR21R22, or -OR23.

Description

Photoelectric conversion element material, organic thin film, photoelectric conversion element, and fused ring compound

[0001] The present invention relates to a material for a photoelectric conversion device, an organic thin film, a photoelectric conversion device, and a fused ring compound.

[0002] Photoelectric conversion elements for image pickup devices are used in applications such as mobile phones and cameras, and their development is being actively pursued.

[0003] In recent years, market demand for photoelectric conversion elements for image sensors has been increasing, and materials that are excellent in dark current, external quantum efficiency, and response speed are being sought. Under these circumstances, the possibility of various polycyclic compounds as the mother nucleus of new materials has been continuously explored and studied. As polycyclic compounds, Patent Document 1 discloses derivatives having benzothienobenzothiophene as the mother nucleus. Furthermore, Patent Document 2 discloses various mother nuclei in addition to benzothienobenzothiophene. Patent Document 3 discloses unsubstituted dibenzo[g,p]chrysene.

[0004] International Publication No. 2015 / 163349 International Publication No. 2020 / 022421 Japanese Patent Application Laid-Open No. 2010-258438

[0005] An object of one embodiment of the present invention is to propose a material for a photoelectric conversion element and a photoelectric conversion element using a compound having a new mother nucleus, while the possibility of using various polycyclic compounds as the mother nucleus of a new material is being explored and investigated.

[0006] Another object of the present invention is to provide a photoelectric conversion element material that contributes to the fabrication of a photoelectric conversion element having low dark current, high external quantum efficiency, and excellent response, and further a compound that contributes to the fabrication of a photoelectric conversion element having low dark current, high external quantum efficiency, and excellent response. Meanwhile, Patent Document 3 describes the use of unsubstituted dibenzo[g,p]chrysene as a crystalline layer between a photoelectric conversion layer and an upper electrode. However, Patent Document 3 does not mention the molecular structural characteristics of dibenzo[g,p]chrysene or an amorphous film containing dibenzo[g,p]chrysene. In addition, the dibenzo[g,p]chrysene described in Patent Document 3 does not provide any knowledge about improving the performance of a photoelectric conversion element for an imaging device.

[0007] The present inventors have found that the above problems can be solved by using a specific fused ring compound, and have completed the present invention.

[0008] Aspects of the present disclosure relate to the following materials for photoelectric conversion devices, organic thin films, photoelectric conversion devices, and fused ring compounds.

[0009] [1] A material for a photoelectric conversion element, comprising a fused ring compound represented by the following formula (1): In formula (1), ring A represents a structure represented by the following formula (2); １ ~R ８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents; R ２１ ~R ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R １ ~R ８may be bonded to each other to form a ring; １ ~R ４ at least one of which is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ２１ R ２２ is a group having a donor substituent selected from In formula (2), X １ ~X ４ The two adjacent carbon atoms in the group represent carbon atoms shared with ring B, and the remaining C—R １５ represents; R １１ ~R １５ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２４ R ２５ , or -OR ２６ represents; R ２４ ~R ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R Ａ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; L represents an alkylene group having 1 to 18 carbon atoms, an optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms, or a single bond. [2] R １ ~R ８ The material for a photoelectric conversion element according to [1], wherein any two of the following adjacent groups are bonded to each other to form a ring represented by the following formula (3): In formula (3), R ３１ ~R３４ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents an adjacent R ３１ ~R ３４ may be bonded to each other to form a ring; the carbon atom marked with * may be bonded to R １ ~R ８ [3] The material for a photoelectric conversion element according to [1] or [2], wherein the fused ring compound represented by formula (1) is a fused ring compound represented by the following formula (1A) or (1B): [In formulas (1A) and (1B), ring A, R １ ~R ８ , and R ３１ ~R ３４ represents the rings A and R of the formulas (1) and (3). １ ~R ８ , and R ３１ ~R ３４ [4] The material for a photoelectric conversion element according to [1] or [2], wherein the fused ring compound represented by formula (1) is a fused ring compound represented by any one of the following formulas (1C) to (1E): [In formulas (1C) to (1E), R １ ~R ８ , R １１ ~R １５ , R Ａ and L is R in the formulas (1) and (2). １ ~R ８ , R １１ ~R １５ , R Ａand represents the same group as L; provided that an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and —NR ２１ R ２２ The group having a donor substituent selected from R １ ~R ４ and R ５ ~R ８ [5] R １ and R ２ , R ３ and R ４ , R ５ and R ６ , or R ７ and R ８ and (3) are bonded to each other to form a ring represented by the formula (3). [6] The material for a photoelectric conversion element according to [3], wherein ring A in the fused ring compound represented by the formula (1) represents a structure represented by the following formula (2A) or (2B): [In formulas (2A) and (2B), X １ ~X ３ represents a carbon atom shared with ring B, R １１ ~R １５ , R Ａ and L is R in the formula (2). １１ ~R １５ , R Ａ and represents the same group as L.] [7] The material for a photoelectric conversion element according to [2], [3], [5], or [6], wherein the fused ring compound represented by formula (1) is a fused ring compound represented by the following formula (1F): [In formula (1F), R ３５ ~R ３８are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents an adjacent R ３５ ~R ３８ may be bonded to each other to form a ring; R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and L is R in the formulas (1) and (3). １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and represents the same group as L.] [8] Adjacent R １ ~R ４ , and R ３１ ~R ３８ and R are not bonded to each other to form a ring. [9] The material for photoelectric conversion elements according to [7] or [8], wherein L is an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond.

[10] The material for photoelectric conversion elements according to [7] or [8], wherein R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３８ , and R Ａeach independently represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, an n-decyl group, an n-dodecyl group, an n-octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR ２１ R ２２ , and -OR ２３ is a group selected from the group consisting of: ２１ ~R ２３ are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

[11] R ３１ ~R ３８is a hydrogen atom.

[12] An organic thin film comprising the material for photoelectric conversion elements according to any one of [1] to

[11] .

[13] A photoelectric conversion element comprising the material for photoelectric conversion elements according to any one of [1] to

[11] .

[14] A photoelectric conversion element comprising the material for photoelectric conversion elements according to any one of [1] to

[11] in a photoelectric conversion layer.

[15] A photoelectric conversion element comprising the material for photoelectric conversion elements according to any one of [1] to

[11] in a hole transport layer or an electron blocking layer.

[16] The material for photoelectric conversion elements according to any one of [1] to

[11] , which is used in a photoelectric conversion element for an imaging element.

[17] A fused ring compound represented by the following formula (4): In formula (4), ring A represents a structure represented by the following formula (5); ａ１ ~R ａ８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ , or -OR ａ２３ represents; R ａ２１ ~R ａ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａ１ ~R ａ８ may be bonded to each other to form a ring; provided that R ａ１ ~R ａ４ at least one of which is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ａ２１ R ａ２２ is a group having a donor substituent selected from the group consisting of: ａ１ ~R ａ８Any two adjacent ones of the above are bonded to each other to form a ring represented by the following formula (6): In formula (5), X ａ１ ~X ａ４ The two adjacent carbon atoms in the group represent carbon atoms shared with ring B, and the remaining C—R ａ１５ represents; R ａ１１ ~R ａ１５ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２４ R ａ２５ , or -OR ａ２６ represents; R ａ２４ ~R ａ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａＡ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; L ａ represents an alkylene group having 1 to 18 carbon atoms, an optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms, or a single bond. In formula (6), R ａ３１ ~R ａ３４ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ , or -OR ａ２３represents an adjacent R ａ３１ ~R ａ３４ may be bonded to each other to form a ring; the carbon atom marked with * may be bonded to R ａ１ ~R ａ８

[18] The fused ring compound according to

[17] , wherein the fused ring compound represented by formula (4) is represented by the following formula (4A) or (4B): [In formulas (4A) and (4B), ring A, R ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４ represents the rings A and R of the formulas (4) and (6). ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４

[19] The fused ring compound according to

[17] or

[18] , wherein ring A represents a structure represented by the following formula (5A) or (5B): [In formulas (5A) and (5B), X ａ１ ~X ａ３ represents a carbon atom shared with ring B, R ａ１１ ~R ａ１５ , R ａＡ , and L ａ is R in the formula (5). ａ１１ ~R ａ１５ , R ａＡ , and L ａ

[20] The fused ring compound according to

[18] or

[19] , wherein the fused ring compound represented by formula (4A) or (4B) is represented by the following formula (4C): [In formula (4C), R a３５ ~R a３８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR a２１ R a２２ , or -ORa２３ represents an adjacent R a３５ ~R a３８ may be bonded to each other to form a ring; R a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a is R in the formulas (4) and (6). a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a

[21] In the fused ring compound represented by formula (4C), adjacent R a１ ~R a４ , and R a３１ ~R a３８

[22] The fused ring compound according to

[20] , wherein L a

[23] The fused ring compound according to

[20] or

[21] , wherein R is an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond. a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３８ , and R aＡeach independently represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, an n-decyl group, an n-dodecyl group, an n-octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR a２１ R a２２ , and -OR a２３ is a group selected from the group consisting of: a２１ ~R a２３ are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

[24] R a３１ ~R a３８

[24] The fused ring compound according to any one of

[20] to

[23] , wherein

[0010] According to one embodiment of the present invention, it is possible to provide a material for a photoelectric conversion element that contributes to the production of a photoelectric conversion element having low dark current, high external quantum efficiency, and excellent response, and further to provide a compound that contributes to the production of a photoelectric conversion element having low dark current, high external quantum efficiency, and excellent response.

[0011] 1 is a schematic cross-sectional view showing an example of a layer structure of a photoelectric conversion element for an imaging element including a material for a photoelectric conversion element for an imaging element according to one aspect of the present invention.

[0012] Hereinafter, a material for a photoelectric conversion element according to one embodiment of the present disclosure will be described in detail.

[0013] <Photoelectric Conversion Device Material> A fused ring compound represented by the following formula (1) can be suitably used as a photoelectric conversion device material. That is, a photoelectric conversion device material according to one embodiment of the present disclosure contains a fused ring compound represented by the following formula (1).

[0014] In formula (1), ring A represents a structure represented by the following formula (2); １ ~R ８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents; R ２１ ~R ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R １ ~R ８ may be bonded to each other to form a ring; １ ~R ４at least one of which is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ２１ R ２２ is a group having a donor substituent selected from

[0015] In formula (2), X １ ~X ４ The two adjacent carbon atoms in the group represent carbon atoms shared with ring B, and the remaining C—R １５ represents; R １１ ~R １５ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２４ R ２５ , or -OR ２６ represents; R ２４ ~R ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R Ａ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; L represents an alkylene group having 1 to 18 carbon atoms, an optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms, or a single bond.

[0016] In the above formula (1), the ring A has the structure represented by the above formula (2) and also has the group having the donor substituent, so that a material for a photoelectric conversion device containing the compound represented by the above formula (1) can provide a photoelectric conversion device having low dark current, high external quantum efficiency, and excellent response. Therefore, the compound represented by the above formula (1) is suitably used as a material for a photoelectric conversion device.

[0017] Specific examples and preferred embodiments of the definitions in the above formulas (1) and (2) are as follows:

[0018] <R １ ~R ８ > R １ ~R ８ Examples of the optionally substituted alkyl group having 1 to 18 carbon atoms as represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isovaleryl group, an n-hexyl group, an i-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, a cyclohexyl group, an octyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-octadecyl group, an n-tridecyl group, an n-tetradecyl group, a 2-ethylhexyl group, a 3-ethylheptyl group, a 3-ethyldecyl group, a 2-hexyldecyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0019] R １ ~R ８ Examples of the alkenyl group having 1 to 18 carbon atoms as the alkyl group include ethenyl, propenyl, butenyl, 2-methylpropenyl, n-pentenyl, 2-methylbutenyl, n-hexenyl, 2-methylpentenyl, n-heptenyl, n-octenyl, 2-ethylhexenyl, n-nonenyl, 2-ethylheptenyl, n-decenyl, n-dodecenyl, cyclopentenyl-1-group, cyclohexenyl-1-group, and cycloheptenyl-1-group.

[0020] R １ ~R ８Examples of the cycloalkyl group having 1 to 18 carbon atoms as the aryl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecyl group, and a cyclododecyl group. The cycloalkyl group may be substituted with an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a cyclopropylmethyl group, a 2-methylpropyl group, a 2,2-dimethylpropyl group, a cyclopropyl group, a tert-butyl group, and a cyclobutyl group.

[0021] R １ ~R ８ Examples of the bicycloalkyl group having 1 to 18 carbon atoms as the aryl group include a norbornyl group, a 3-pinanyl group, a bicyclo[3.1.0]hexyl group, a bicyclo[2.2.1]heptyl group, and a bicyclo[2.2.2]oct-2-yl group.

[0022] R １ ~R ８ Examples of the tricycloalkyl group having 1 to 20 carbon atoms as the aryl group include an adamantyl group, a noradamantyl group, and a diamantyl group.

[0023] R １ ~R ８Examples of the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as the aromatic hydrocarbon group include an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted anthryl group, an optionally substituted phenanthryl group, an optionally substituted pyrenyl group, an optionally substituted chrysenyl group, an optionally substituted benzochrysenyl group, an optionally substituted dibenzochrysenyl group, an optionally substituted fluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted naphthylphenyl group, an optionally substituted phenylnaphthyl group, an optionally substituted naphthylnaphthyl group, an optionally substituted phenanthrylphenyl group, an optionally substituted diphenylfluorenyl group, and an optionally substituted dibenzo[g,p]chrysenyl group.

[0024] R １ ~R ８Examples of the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as the heteroaromatic group include an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranylphenyl group, an optionally substituted dibenzothionylphenyl group, an optionally substituted carbazolylphenyl group, an optionally substituted pyrrolyl group, an optionally substituted thienyl group, an optionally substituted furyl group, an optionally substituted imidazolyl group, an optionally substituted pyrazolyl group, an optionally substituted thiazolyl group, an optionally substituted isothiazolyl group, an optionally substituted oxazolyl group, an optionally substituted isoxazolyl group, an optionally substituted pyridyl group, an optionally substituted phenylpyridyl group, an optionally substituted pyridyl group, a phenyl group, an optionally substituted pyrimidyl group, an optionally substituted pyrazyl group, an optionally substituted 1,3,5-triazyl group, an optionally substituted 1,3,5-triazylphenyl group, an optionally substituted 1,3,5-triazylbiphenyl group, an optionally substituted 4,6-diphenyl-1,3,5-triazyl group, an optionally substituted indolyl group, an optionally substituted benzothienyl group, an optionally substituted benzofuranyl group, an optionally substituted benzimidazolyl group, an optionally substituted indazolyl group, an optionally substituted benzothiazolyl group, an optionally substituted benzoisothiazolyl group, an optionally substituted 2,1,3-benzothiadiazolyl group, an optionally substituted benzoxazolyl group, an optionally substituted benzoisoxazolyl group, an optionally substituted 2,1,Examples of the alkyl group include a 3-benzoxadiazolyl group, an optionally substituted quinolyl group, an optionally substituted isoquinolyl group, an optionally substituted quinoxalyl group, an optionally substituted quinazolyl group, an optionally substituted carbazolyl group, an optionally substituted 9-phenylcarbazolyl group, an optionally substituted 9-(4-biphenylyl)carbazolyl group, an optionally substituted dibenzothienyl group, an optionally substituted dibenzofuranyl group, an optionally substituted phenoxazinyl group, an optionally substituted phenothiazinyl group, an optionally substituted phenazine group, and an optionally substituted thianthrenyl group.

[0025] R ２１ ~R ２３ The optionally substituted alkyl group having 1 to 18 carbon atoms as R １ ~R ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0026] R ２１ ~R ２３ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R １ ~R ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0027] R ２１ ~R ２３ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R １ ~R ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0028] <R １１ ~R １５ > R １１ ~R １５ The optionally substituted alkyl group having 1 to 18 carbon atoms as R １ ~R ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0029] R １１ ~R １５ As the alkenyl group having 1 to 18 carbon atoms, the above-mentioned R １ ~R ８ Examples thereof include the same groups as the alkenyl group having 1 to 18 carbon atoms as mentioned above.

[0030] R １１ ~R １５ The cycloalkyl group having 1 to 18 carbon atoms as R １ ~R ８ Examples include the same groups as the cycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0031] R １１ ~R １５ As the bicycloalkyl group having 1 to 18 carbon atoms, the above-mentioned R １ ~R ８ Examples include the same groups as the bicycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0032] R １１ ~R １５ The tricycloalkyl group having 1 to 20 carbon atoms as R １ ~R ８ Examples include the same groups as the tricycloalkyl group having 1 to 20 carbon atoms as mentioned above.

[0033] R １１ ~R １５ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R １ ~R ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0034] R １１ ~R １５ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R １ ~R ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0035] R ２４ ~R ２６The optionally substituted alkyl group having 1 to 18 carbon atoms as R １ ~R ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0036] R ２４ ~R ２６ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R １ ~R ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0037] R ２４ ~R ２６ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R １ ~R ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0038] <R Ａ > R Ａ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R １ ~R ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0039] R Ａ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R １ ~R ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0040] <L> Examples of the alkylene group having 1 to 18 carbon atoms represented by L include a methylene group, an ethane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, and a decane-1,10-diyl group.

[0041] Examples of the optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms represented by L include a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenylnaphthalene-diyl group, a binaphthylene group, a fluorene-diyl group, a benzofluorene-diyl group, a dibenzofluorene-diyl group, a phenanthrene-diyl group, a fluoranthene-diyl group, an anthracene-diyl group, a chrysene-diyl group, a pyrene-diyl group, a triphenylene-diyl group, and a perylene-diyl group.

[0042] Examples of the optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms as L include a pyrrole-diyl group, a thiophene-diyl group, a furan-diyl group, an imidazole-diyl group, a thiazole-diyl group, an isothiazole-diyl group, an oxazole-diyl group, an isoxazole-diyl group, a pyridine-diyl group, a pyrimidine-diyl group, a pyrazine-diyl group, a triazine-idyl group, an indole-diyl group, a benzothiophene-diyl group, a benzofuran-diyl group, a benzimidazole-diyl group, a benzothiazole-diyl group, a benzisothiazole-diyl group, a 2,1,3-benzothiadiazole-diyl group, a benzoxazole-diyl group, a benzisoxazole-diyl group, a 2,1,3-benzobenzothiadiazole-diyl group, a benzoisoxazole-diyl group, a 2,1,3-benzobenzobenzodiyl group, a benzoiso ... Examples of the alkyl group include benzoxadiazole-diyl group, thienothiophene-diyl group, dithienothiophene-diyl group, benzodithiophene-diyl group, quinoline-diyl group, isoquinoline-diyl group, quinoxaline-diyl group, phenanthroline-diyl group, dibenzothiophene-diyl group, benzothienobenzothiophene-diyl group, dibenzofuran-diyl group, carbazole-diyl group, phenoxazine-diyl group, phenothiazine-diyl group, thianthrene-diyl group, phenylthiophene-diyl group, diphenylthiophene-diyl group, phenylfuran-diyl group, diphenylfuran-diyl group, bithiophene-diyl group, terthiophene-diyl group, phenylpyridine-diyl group, and bipyridine-diyl group.

[0043] In the above formula (1), R １ ~R ８It is preferable that any two adjacent groups of the above are bonded to each other to form a ring represented by the following formula (3).

[0044] In formula (3), R ３１ ~R ３４ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents an adjacent R ３１ ~R ３４ may be bonded to each other to form a ring; the carbon atom marked with * may be bonded to R １ ~R ８ represent carbon atoms in the six-membered aromatic ring in formula (1) to which any two adjacent ones of

[0045] Preferred embodiments of the definition in the above formula (3) are as follows:

[0046] <R ３１ ~R ３４ > R ３１ ~R ３４ The optionally substituted alkyl group having 1 to 18 carbon atoms as R １ ~R ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0047] R ３１ ~R ３４ As the alkenyl group having 1 to 18 carbon atoms, the above-mentioned R １ ~R ８ Examples thereof include the same groups as the alkenyl group having 1 to 18 carbon atoms as mentioned above.

[0048] R ３１ ~R ３４ The cycloalkyl group having 1 to 18 carbon atoms as R １ ~R８ Examples include the same groups as the cycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0049] R ３１ ~R ３４ As the bicycloalkyl group having 1 to 18 carbon atoms, the above-mentioned R １ ~R ８ Examples include the same groups as the bicycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0050] R ３１ ~R ３４ The tricycloalkyl group having 1 to 20 carbon atoms as R １ ~R ８ Examples include the same groups as the tricycloalkyl group having 1 to 20 carbon atoms as mentioned above.

[0051] R ３１ ~R ３４ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R １ ~R ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0052] R ３１ ~R ３４ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R １ ~R ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0053] The fused ring compound represented by the above formula (1) is preferably a fused ring compound represented by the following formula (1A) or (1B):

[0054] In formulas (1A) and (1B), ring A, R １ ~R ８ , and R ３１ ~R ３４ represents the rings A and R of the formulas (1) and (3). １ ~R ８ , and R ３１ ~R ３４ represents the same group as

[0055] The fused ring compound represented by the above formula (1) is preferably a fused ring compound represented by any one of the following formulae (1C) to (1E).

[0056] In formulas (1C) to (1E), R １ ~R ８ , R １１ ~R １５ , R Ａ and L is R in the formulas (1) and (2). １ ~R ８ , R １１ ~R １５ , R Ａ and represents the same group as L; provided that an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and —NR ２１ R ２２ The group having a donor substituent selected from R １ ~R ４ and R ５ ~R ８ It may be at least one of the above.

[0057] In the fused ring compounds represented by the above formulas (1C) to (1E), R １ and R ２ , R ３ and R ４ , R ５ and R ６ , or R ７ and R ８ and (3) are preferably bonded to each other to form a ring represented by the above formula (3).

[0058] In the fused ring compounds represented by the above formulas (1), (1A), and (1B), it is preferable that ring A represents a structure represented by the following formula (2A) or (2B).

[0059] In formulas (2A) and (2B), X １ ~X ３ represents a carbon atom shared with ring B, R １１ ~R １５ , RＡ and L is R in the formula (2). １１ ~R １５ , R Ａ and represents the same group as L.

[0060] The fused ring compound represented by the above formula (1) is preferably a fused ring compound represented by the following formula (1F):

[0061] In formula (1F), R ３５ ~R ３８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ , or -OR ２３ represents an adjacent R ３５ ~R ３８ may be bonded to each other to form a ring; R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and L is R in the formulas (1) and (3). １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and represents the same group as L.

[0062] In the fused ring compound represented by the above formula (1F), adjacent R １ ~R ４ , and R ３１ ~R ３８ are preferably not bonded to each other to form a ring.

[0063] In the fused ring compound represented by the above formula (1F), L is preferably an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond.

[0064] In the fused ring compound represented by the above formula (1F), R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３８ , and R Ａ each independently represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an octyl group, a decyl group, a dodecyl group, an octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR ２１ R ２２ , and -OR ２３ is a group selected from the group consisting of: ２１ ~R ２３are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

[0065] In the fused ring compound represented by the above formula (1F), R ３１ ~R ３８ is preferably a hydrogen atom.

[0066] <Physical Properties of Fused Ring Compound> Preferred physical properties of the fused ring compound represented by formula (1) are described below.

[0067] (HOMO Value) The HOMO value of the fused ring compound represented by formula (1) is not particularly limited, but from the viewpoint of compatibility with photoelectric conversion elements, it is preferably 5.0 to 6.5 eV. Note that this HOMO value is a value obtained by measuring a vapor-deposited film using an atmospheric photoelectron yield spectrometer.

[0068] (Band Gap) The band gap of the fused ring compound represented by formula (1) is not particularly limited, but from the viewpoint of compatibility with photoelectric conversion elements, it is preferably 2.5 to 4.0 eV. Note that this band gap is a value obtained from the wavelength edge of the absorption spectrum of the vapor-deposited film.

[0069] (LUMO Value) The LUMO value of the fused ring compound represented by formula (1) is not particularly limited, but from the viewpoint of compatibility with photoelectric conversion elements, it is preferably 2.0 to 3.5 eV. Note that this LUMO value is a value obtained from the above-mentioned HOMO value and band gap.

[0070] (Glass Transition Temperature) The glass transition temperature of the fused ring compound represented by formula (1) is not particularly limited, but from the viewpoint of compatibility with photoelectric conversion elements, it is preferably 130° C. or higher. Note that this glass transition temperature is a value obtained by differential scanning calorimetry.

[0071] (Molecular Weight) The molecular weight of the fused ring compound represented by formula (1) is not particularly limited, but is preferably 600 or more and less than 1,000 from the viewpoint of heat resistance stability during sublimation.

[0072] <Specific Examples of Fused Ring Compounds> Preferred examples of the fused ring compounds represented by formula (1) are shown below, but the fused ring compounds are not limited to these compounds.

[0073] <Specific Preferred Examples of Fused Ring Compounds> Preferred examples of the fused ring compound represented by formula (1) are shown below, but the fused ring compound is not limited to these compounds.

[0074] In the skeletons of (Aa) to (Ej) shown in Tables 1 to 3, a compound in which the substituent R is a group n selected from the groups shown in Tables 4 to 6 is defined as (Lm-n). Here, Lm represents any symbol of Aa to Ej, and n represents any integer from 1 to 115. For example, the compound (Ab-2) has the skeleton of (Ab), and indicates that the substituent R of the skeleton is a methyl group.

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] <Uses of Photoelectric Conversion Device Material> The above-described photoelectric conversion device material is suitably used, for example, as a material for a photoelectric conversion device for an imaging device. The material for a photoelectric conversion device for an imaging device is preferably, for example, a charge transport material for a photoelectric conversion device for an imaging device or a charge blocking material for a photoelectric conversion device for an imaging device. The charge transport material for a photoelectric conversion device for an imaging device is preferably, for example, a hole transport material for a photoelectric conversion device for an imaging device. The charge blocking material for a photoelectric conversion device for an imaging device is preferably, for example, an electron blocking material for a photoelectric conversion device for an imaging device. The above-described photoelectric conversion device material is also suitably used as a material for an organic electronic device. Examples of organic electronic devices include organic electroluminescence devices and organic photoelectric conversion devices. Examples of materials for organic electronic devices include materials for organic electroluminescence devices and materials for organic photoelectric conversion devices. The above-described material for an organic electronic device is preferably used as an organic thin film.

[0082] Preferred embodiments of the material for photoelectric conversion elements containing the above-mentioned fused ring compound include an organic thin film containing the material for photoelectric conversion elements, a photoelectric conversion element containing the material for photoelectric conversion elements, a photoelectric conversion element containing the material for photoelectric conversion elements in a photoelectric conversion layer, and a photoelectric conversion element containing the material for photoelectric conversion elements in a hole transport layer or an electron blocking layer.

[0083] Hereinafter, a photoelectric conversion element for an image sensor according to this embodiment will be described as an example.

[0084] <<Photoelectric Conversion Element for Image Sensor>> The photoelectric conversion element for image sensor of this embodiment contains the charge transport material for photoelectric conversion element for image sensor described above. The configuration of the photoelectric conversion element for image sensor is not particularly limited, but examples thereof include the following configurations (i) to (v).

[0085] (i) Lower electrode / photoelectric conversion layer / upper electrode (ii) Lower electrode / electron transport layer (hole blocking layer) / photoelectric conversion layer / upper electrode (iii) Lower electrode / photoelectric conversion layer / hole transport layer (electron blocking layer) / upper electrode (iv) Lower electrode / electron transport layer (hole blocking layer) / photoelectric conversion layer / hole transport layer (electron blocking layer) / upper electrode (v) Lower electrode / electron transport layer (hole blocking layer) / photoelectric conversion layer / hole transport layer (electron blocking layer) / buffer layer / upper electrode

[0086] The buffer layer may be replaced with a layer having a different name or function, as needed, such as a hole injection layer or a work function adjustment layer.

[0087] A preferred layer configuration of the photoelectric conversion element for an imaging device includes, for example, an upper electrode, a lower electrode, a photoelectric conversion layer, and a hole transport layer, where the photoelectric conversion layer is disposed between the upper electrode and the lower electrode, and the hole transport layer is disposed between the photoelectric conversion layer and the upper electrode. Another preferred layer configuration of the photoelectric conversion element for an imaging device includes, for example, an upper electrode, a lower electrode, a photoelectric conversion layer, a hole transport layer, and a buffer layer, where the photoelectric conversion layer is disposed between the upper electrode and the lower electrode, the hole transport layer is disposed between the photoelectric conversion layer and the upper electrode, and the buffer layer is disposed between the hole transport layer and the upper electrode and adjacent to the hole transport layer.

[0088] The photoelectric conversion element for an imaging device preferably contains the above-described material for a photoelectric conversion element for an imaging device in at least one layer selected from the group consisting of an electron transport layer (hole blocking layer), a photoelectric conversion layer, a hole transport layer (electron blocking layer), and a buffer layer. The photoelectric conversion element for an imaging device preferably contains the above-described material for a photoelectric conversion element for an imaging device in the photoelectric conversion layer and / or the hole transport layer (electron blocking layer), and more preferably contains the above-described material for a photoelectric conversion element for an imaging device in the hole transport layer (electron blocking layer). The material for a photoelectric conversion element for an imaging device may be contained in multiple layers of the photoelectric conversion element for an imaging device.

[0089] Hereinafter, the photoelectric conversion element for an image sensor according to this embodiment will be described in more detail using the configuration (v) above as an example, with reference to Fig. 1. Fig. 1 is a schematic cross-sectional view showing an example of the layered configuration of a photoelectric conversion element for an image sensor including a hole transport material for a photoelectric conversion element for an image sensor or an electron blocking material for a photoelectric conversion element for an image sensor according to this embodiment.

[0090] 1 includes, in this order, a substrate 1, a lower electrode 2, an electron transport layer (hole blocking layer) 3, a photoelectric conversion layer 4, a hole transport layer (electron blocking layer) 5, a buffer layer 6, and an upper electrode 7. Note that in the photoelectric conversion element for an image sensor of this embodiment, some of these layers may be omitted, and other layers may be added.

[0091] In the photoelectric conversion element 100 for an imaging device, light is incident from below the transparent lower electrode 2. Furthermore, a voltage is applied to the photoelectric conversion element 100 for an imaging device so that, of the charges (holes and electrons) generated in the photoelectric conversion layer 4, the electrons move to the lower electrode 2 and the holes move to the upper electrode 7. That is, in the photoelectric conversion element 100 for an imaging device, the lower electrode 2 serves as an electron collecting electrode and the upper electrode 7 serves as a hole collecting electrode.

[0092] [Layer Containing Charge Transport Material for Photoelectric Conversion Element for Image Sensor] The photoelectric conversion element 100 for image sensors contains a material for photoelectric conversion elements for image sensors in at least one layer selected from the group consisting of the electron transport layer (hole blocking layer) 3, the photoelectric conversion layer 4, the hole transport layer (electron blocking layer) 5, and the buffer layer 6. The photoelectric conversion element 100 for image sensors preferably contains a charge transport material for photoelectric conversion elements for image sensors or a charge blocking material for photoelectric conversion elements for image sensors in the photoelectric conversion layer 4 and / or the hole transport layer (electron blocking layer) 5, and more preferably contains a charge transport material for photoelectric conversion elements for image sensors or a charge blocking material for photoelectric conversion elements for image sensors in the hole transport layer (electron blocking layer) 5. The charge transport material for photoelectric conversion elements for image sensors or the charge blocking material for photoelectric conversion elements for image sensors may be contained in multiple layers of the photoelectric conversion element 100 for image sensors.

[0093] Hereinafter, a photoelectric conversion element 100 for an imaging device in which the hole transport layer (electron blocking layer) 5 contains a hole transport material for a photoelectric conversion element for an imaging device or an electron blocking material for a photoelectric conversion element for an imaging device will be described.

[0094] [Substrate 1] The substrate is not particularly limited, and examples thereof include a glass plate, a quartz plate, a plastic plate, etc. In a configuration in which light is incident from the substrate 1 side, it is preferable that the substrate 1 has high transmittance to the wavelength of light (for example, a transmittance of 80% or more, preferably a transmittance of 90% or more).

[0095] [Lower electrode 2] A lower electrode 2 is provided on the substrate 1. In the case of a photoelectric conversion element for an imaging device configured so that light passes through the lower electrode 2 and enters the photoelectric conversion layer, it is preferable that the lower electrode 2 has high transparency (for example, a transmittance of 80% or more, preferably a transmittance of 90% or more) with respect to the wavelength of the incident light.

[0096] There are no particular limitations on the transparent material used for the lower electrode 2. From the viewpoint of excellent light transmittance, the material constituting the lower electrode 2 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, metal sulfides such as zinc sulfide, or the like.

[0097] In the case of a photoelectric conversion element for an imaging device configured so that light enters the photoelectric conversion layer only from the upper electrode 7 side, the transmission characteristics of the lower electrode 2 are not important. Therefore, examples of materials that can be used for the lower electrode 2 in this case include gold, iridium, molybdenum, palladium, platinum, etc.

[0098] [Electron Transport Layer (Hole Blocking Layer) 3 ] The electron transport layer (hole blocking layer) 3 is provided between the lower electrode 2 and the photoelectric conversion layer 4 .

[0099] The electron transport layer (hole blocking layer) 3 has the role of transporting electrons generated in the photoelectric conversion layer 4 to the lower electrode 2 and the role of blocking holes generated in the photoelectric conversion layer 4 from moving to the lower electrode 2.

[0100] The electron transport layer (hole blocking layer) 3 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions. The electron transport layer (hole blocking layer) 3 may have, for example, a two-layer structure including a layer made of a material specialized for hole blocking properties and adjacent to the photoelectric conversion layer 4, and a layer made of a material specialized for electron transport properties and adjacent to the lower electrode 2.

[0101] The electron transport layer (hole blocking layer) 3 may be a layer containing a conventionally known electron transport material, such as bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine, N,N'-diphenyl-1,4,5,8-naphthalenetetracarboxylic acid diimide, and N,N'-di(4-pyridyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide.

[0102] [Photoelectric conversion layer 4] The photoelectric conversion layer 4 is provided between the electron transport layer (hole blocking layer) 3 and a hole transport layer (electron blocking layer) 5 described later. The photoelectric conversion layer 4 contains a material having a photoelectric conversion function.

[0103] The photoelectric conversion layer 4 may be made of either an organic or inorganic material, as long as it is capable of generating signal charges corresponding to the amount of received light. When the photoelectric conversion layer 4 is made of an organic material, it may have a single-layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions. Materials used for the photoelectric conversion layer 4 include n-type and p-type semiconductors. N-type semiconductors are organic semiconductors with acceptor properties, and compounds that readily accept electrons and have high electron transport properties are used. P-type semiconductors are organic semiconductors with donor properties, and compounds that readily donate electrons and have high hole transport properties are used. When multiple materials are used for the photoelectric conversion layer 4, combinations include, for example, n-type and p-type semiconductors, n-type and compounds with lower acceptor properties than the n-type semiconductor, and p-type and compounds with lower donor properties than the p-type semiconductor. Each material may be used alone, or two or more materials may be used. The photoelectric conversion layer 4 may also contain a dye compound that excels in absorbing specific light. The dye compound may be a compound having lower acceptor properties than the n-type semiconductor, or a compound having lower donor properties than the p-type semiconductor. To enhance photoelectric conversion efficiency, the photoelectric conversion layer 4 desirably contains a dye compound in addition to the n-type and p-type semiconductors. Examples of compounds contained in the photoelectric conversion layer 4 include coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, fullerene and its derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxadiazole, and triazole, naphthalenetetracarboxylic acid diimide, and hole transport materials. The photoelectric conversion layer 4 made of these materials may be formed, for example, by vapor deposition using a mixed powder of powders of the respective materials, or by co-evaporation of the respective materials in any ratio.

[0104] Specific examples of coumarin derivatives include coumarin 6 and coumarin 30. Specific examples of quinacridone derivatives include N,N-dimethylquinacridone. Specific examples of phthalocyanine derivatives include boron subphthalocyanine chloride, boron subnaphthalocyanine chloride (SubNC), F6-SubPC-OC6F5, and Cl6-SubPC-OC6. Specific examples of fullerenes and their derivatives include

[60] fullerene,

[70] fullerene, and [6,6]-phenyl-C61-methyl butyrate (

[60] PCBM). The hole transport material may be a known hole transport material. Examples of hole transport materials include aromatic tertiary amine compounds, naphthalene compounds, anthracene compounds, tetracene compounds, pentacene compounds, phenanthrene compounds, pyrene compounds, perylene compounds, fluorene compounds, carbazole compounds, indole compounds, pyrrole compounds, picene compounds, thiophene compounds, benzotrifuran compounds, benzotrithiophene compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzodithiophene compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds. Among these, fluorene compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, indolocarbazole compounds, and the like are preferred, and fluorene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds are more preferred.

[0105] Specific examples of hole transport materials include 9,9'-(9,9'-spirobi[9H-fluorene]-2,7'-diyl)bis[9H-carbazole], 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophene (DiPh-BTBT), benzo[1,2-b:3,4-b':5,6-b'']trifuran compounds, benzo[1,2-b:3,4-b':5,6-b'']trithiophene compounds, naphtho[1,2-b:5,6-b']dithiophene, naphtho[2,3-b]naphtho[2',3' :4,5]thieno[2,3-d]thiophene, benzo[1,2-b:4,5-b']difuran, benzo[1,2-b:4,5-b']dithiophene, benzo[1,2-b:4,5-b']bis[1]benzothiophene, naphtho[1,2-b:5,6-b']bis[1]benzothiophene, chryseno[1,2-b:8,7-b']dithiophene, [1]benzothieno[3,2-b][1]benzothiophene, compounds represented by the following formula (ic-1), and compounds represented by the following formula (ic-2) are listed.

[0106]

[0107] The material having the photoelectric conversion function described above may be contained only in the photoelectric conversion layer 4, or may also be contained in layers other than the photoelectric conversion layer 4. For example, layers adjacent to the photoelectric conversion layer 4 (electron transport layer (hole blocking layer) 3, hole transport layer (electron blocking layer) 5) may contain a material having the photoelectric conversion function.

[0108] [Hole Transport Layer (Electron Blocking Layer) 5] The hole transport layer (electron blocking layer) 5 is provided between the photoelectric conversion layer 4 and a buffer layer 6 described later.

[0109] The hole transport layer (electron blocking layer) 5 has a role of transporting holes generated in the photoelectric conversion layer 4 toward the upper electrode 7, and a role of blocking electrons generated in the photoelectric conversion layer 4 from moving toward the upper electrode 7. The hole transport layer (electron blocking layer) 5 preferably contains the above-mentioned charge transport material for a photoelectric conversion element for an imaging device or charge blocking material for a photoelectric conversion element for an imaging device.

[0110] The hole transport layer (electron blocking layer) 5 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions. The hole transport layer (electron blocking layer) 5 may have, for example, a two-layer structure including a layer made of a material specialized for electron blocking properties and adjacent to the photoelectric conversion layer 4, and a layer made of a material specialized for hole transport properties and adjacent to the buffer layer 6.

[0111] The hole transport layer (electron blocking layer) 5 may further contain a conventionally known hole transport material in addition to the above-mentioned material for a photoelectric conversion element for an imaging device. Preferred compounds and specific examples of the conventionally known hole transport material include the same compounds as those described in the section on the photoelectric conversion layer 4.

[0112] [Buffer Layer 6] A buffer layer 6 is provided between the hole transport layer (electron blocking layer) 5 and the upper electrode 7 described below. When the upper electrode 7 is formed by sputtering, the buffer layer 6 serves to reduce damage to the organic layer (e.g., the hole transport layer (electron blocking layer) 5) during sputtering. The buffer layer 6 also serves to efficiently accept holes from the hole transport layer (electron blocking layer) 5 by adjusting the work function of the buffer layer 6, and is also called a hole injection layer or a work function adjustment layer.

[0113] The material constituting the buffer layer 6 may be a known material, such as naphthalene-1,4,5,8-tetracarboxylic dianhydride (NTCDA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), or the like.

[0114] [Upper Electrode 7] The upper electrode 7 is provided on the buffer layer 6. The material of the upper electrode 7 is not particularly limited, and examples thereof include sodium, sodium-potassium alloy, magnesium, lithium, a magnesium / copper mixture, silver, a magnesium / silver mixture, aluminum, a magnesium / aluminum mixture, a magnesium / indium mixture, and aluminum / aluminum oxide (Al ２ O ３ ) mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc.

[0115] [Method of Forming Each Layer] Each layer other than the lower electrode 2 and the upper electrode 7 can be formed by thinning the material of each layer (and, if necessary, materials such as binder resin, solvent, etc.) by a known method such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett) method. The thickness of each layer other than the lower electrode 2 and the upper electrode 7 is not particularly limited and can be selected appropriately depending on the situation. The thickness of each layer other than the lower electrode 2 and the upper electrode 7 is usually in the range of 5 nm to 5 μm.

[0116] The lower electrode 2 and the upper electrode 7 can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. When the lower electrode 2 and the upper electrode 7 have a pattern, the pattern can be formed, for example, through a mask of a desired shape. Alternatively, after forming a thin film by vapor deposition, sputtering, or the like, a pattern of a desired shape can be formed by photolithography.

[0117] The film thickness of the lower electrode 2 and the upper electrode 7 may be 1 μm or less, and is preferably 10 nm or more and 200 nm or less.

[0118] The materials constituting the lower electrode 2 and the upper electrode 7 may be interchanged as necessary (this is also called an inverted structure). In this structure, light passes through the upper electrode 7 and enters the photoelectric conversion layer 4, forming a photoelectric conversion element for an imaging device.

[0119] An imaging element including a photoelectric conversion element according to this embodiment can be applied to, for example, imaging elements in digital cameras, digital video cameras, etc., and imaging elements built into mobile phones, etc. Although the preferred embodiments of the present invention have been described above, the present invention is not limited to the above embodiments.

[0120] The fused ring compound according to one embodiment of the present disclosure will be described in detail below.

[0121] <Fused Ring Compound> A fused ring compound according to one embodiment of the present disclosure is represented by the following formula (4).

[0122] In formula (4), ring A represents a structure represented by the following formula (5); ａ１ ~R ａ８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ , or -OR ａ２３ represents; R ａ２１ ~R ａ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａ１ ~R ａ８ may be bonded to each other to form a ring; provided that R ａ１ ~R ａ４ at least one of which is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ａ２１ R ａ２２ is a group having a donor substituent selected from the group consisting of: ａ１ ~R ａ８ Any two adjacent ones of the above are bonded to each other to form a ring represented by the following formula (6):

[0123] In formula (5), X ａ１ ~X ａ４ The two adjacent carbon atoms in the group represent carbon atoms shared with ring B, and the remaining C—R ａ１５ represents; R ａ１１ ~R ａ１５are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２４ R ａ２５ , or -OR ａ２６ represents; R ａ２４ ~R ａ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａＡ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; L ａ represents an alkylene group having 1 to 18 carbon atoms, an optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms, or a single bond.

[0124] In formula (6), R ａ３１ ~R ａ３４ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ , or -OR ａ２３ represents an adjacent R ａ３１ ~R ａ３４ may be bonded to each other to form a ring; the carbon atom marked with * may be bonded to R ａ１ ~R ａ８ represent carbon atoms in the six-membered aromatic ring in formula (4) to which any two adjacent ones of

[0125] In the above formula (4), the compound represented by the above formula (4) has the structure represented by the above formula (5) as ring A and also has the group having the donor substituent, so that the compound represented by the above formula (4) is suitable for producing a photoelectric conversion element having a low dark current, a high external quantum efficiency, and an excellent response. Therefore, the compound represented by the above formula (4) is suitable for use as a material for a photoelectric conversion element.

[0126] Specific examples and preferred embodiments of the definitions in the above formulas (4) to (6) are as follows:

[0127] <R ａ１ ~R ａ８ > R ａ１ ~R ａ８ Examples of the optionally substituted alkyl group having 1 to 18 carbon atoms as represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isovaleryl group, an n-hexyl group, an i-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, a cyclohexyl group, an octyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-octadecyl group, an n-tridecyl group, an n-tetradecyl group, a 2-ethylhexyl group, a 3-ethylheptyl group, a 3-ethyldecyl group, a 2-hexyldecyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0128] R ａ１ ~R ａ８ Examples of the alkenyl group having 1 to 18 carbon atoms as the alkyl group include ethenyl, propenyl, butenyl, 2-methylpropenyl, n-pentenyl, 2-methylbutenyl, n-hexenyl, 2-methylpentenyl, n-heptenyl, n-octenyl, 2-ethylhexenyl, n-nonenyl, 2-ethylheptenyl, n-decenyl, n-dodecenyl, cyclopentenyl-1-group, cyclohexenyl-1-group, and cycloheptenyl-1-group.

[0129] R ａ１ ~R ａ８Examples of the cycloalkyl group having 1 to 18 carbon atoms as the aryl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecyl group, and a cyclododecyl group. The cycloalkyl group may be substituted with an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a cyclopropylmethyl group, a 2-methylpropyl group, a 2,2-dimethylpropyl group, a cyclopropyl group, a tert-butyl group, and a cyclobutyl group.

[0130] R ａ１ ~R ａ８ Examples of the bicycloalkyl group having 1 to 18 carbon atoms as the aryl group include a norbornyl group, a 3-pinanyl group, a bicyclo[3.1.0]hexyl group, a bicyclo[2.2.1]heptyl group, and a bicyclo[2.2.2]oct-2-yl group.

[0131] R １ ~R ８ Examples of the tricycloalkyl group having 1 to 20 carbon atoms as the aryl group include an adamantyl group, a noradamantyl group, and a diamantyl group.

[0132] R ａ１ ~R ａ８Examples of the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as the aromatic hydrocarbon group include an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted anthryl group, an optionally substituted phenanthryl group, an optionally substituted pyrenyl group, an optionally substituted chrysenyl group, an optionally substituted benzochrysenyl group, an optionally substituted dibenzochrysenyl group, an optionally substituted fluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted naphthylphenyl group, an optionally substituted phenylnaphthyl group, an optionally substituted naphthylnaphthyl group, an optionally substituted phenanthrylphenyl group, an optionally substituted diphenylfluorenyl group, and an optionally substituted dibenzo[g,p]chrysenyl group.

[0133] R ａ１ ~R ａ８Examples of the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as the heteroaromatic group include an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranylphenyl group, an optionally substituted dibenzothionylphenyl group, an optionally substituted carbazolylphenyl group, an optionally substituted pyrrolyl group, an optionally substituted thienyl group, an optionally substituted furyl group, an optionally substituted imidazolyl group, an optionally substituted pyrazolyl group, an optionally substituted thiazolyl group, an optionally substituted isothiazolyl group, an optionally substituted oxazolyl group, an optionally substituted isoxazolyl group, an optionally substituted pyridyl group, an optionally substituted phenylpyridyl group, an optionally substituted pyridyl group, a phenyl group, an optionally substituted pyrimidyl group, an optionally substituted pyrazyl group, an optionally substituted 1,3,5-triazyl group, an optionally substituted 1,3,5-triazylphenyl group, an optionally substituted 1,3,5-triazylbiphenyl group, an optionally substituted 4,6-diphenyl-1,3,5-triazyl group, an optionally substituted indolyl group, an optionally substituted benzothienyl group, an optionally substituted benzofuranyl group, an optionally substituted benzimidazolyl group, an optionally substituted indazolyl group, an optionally substituted benzothiazolyl group, an optionally substituted benzoisothiazolyl group, an optionally substituted 2,1,3-benzothiadiazolyl group, an optionally substituted benzoxazolyl group, an optionally substituted benzoisoxazolyl group, an optionally substituted 2,1,Examples of the alkyl group include a 3-benzoxadiazolyl group, an optionally substituted quinolyl group, an optionally substituted isoquinolyl group, an optionally substituted quinoxalyl group, an optionally substituted quinazolyl group, an optionally substituted carbazolyl group, an optionally substituted 9-phenylcarbazolyl group, an optionally substituted 9-(4-biphenylyl)carbazolyl group, an optionally substituted dibenzothienyl group, an optionally substituted dibenzofuranyl group, an optionally substituted phenoxazinyl group, an optionally substituted phenothiazinyl group, an optionally substituted phenazine group, and an optionally substituted thianthrenyl group.

[0134] R ａ２１ ~Ra ２３ The optionally substituted alkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0135] R ａ２１ ~Ra ２３ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0136] R ａ２１ ~Ra ２３ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0137] <R ａ１１ ~R ａ１５ > R ａ１１ ~R ａ１５ The optionally substituted alkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0138] R ａ１１ ~R ａ１５ As the alkenyl group having 1 to 18 carbon atoms, the above-mentioned R ａ１ ~R ａ８ Examples thereof include the same groups as the alkenyl group having 1 to 18 carbon atoms as mentioned above.

[0139] R ａ１１ ~R ａ１５ The cycloalkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the cycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0140] R ａ１１ ~R ａ１５ As the bicycloalkyl group having 1 to 18 carbon atoms, the above-mentioned R ａ１ ~R ａ８ Examples include the same groups as the bicycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0141] R ａ１１ ~R ａ１５ The tricycloalkyl group having 1 to 20 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the tricycloalkyl group having 1 to 20 carbon atoms as mentioned above.

[0142] R ａ１１ ~R ａ１５ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0143] R ａ１１ ~R ａ１５ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0144] R ａ２４ ~R ａ２６The optionally substituted alkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0145] R ａ２４ ~R ａ２６ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0146] R ａ２４ ~R ａ２６ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0147] <R Ａ > R ａＡ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0148] R ａＡ The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0149] <L ａ > L ａ Examples of the alkylene group having 1 to 18 carbon atoms as the alkylene group include a methylene group, an ethane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, and a decane-1,10-diyl group.

[0150] L ａ Examples of the optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms as the aromatic hydrocarbon group include a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenylnaphthalene-diyl group, a binaphthylene group, a fluorene-diyl group, a benzofluorene-diyl group, a dibenzofluorene-diyl group, a phenanthrene-diyl group, a fluoranthene-diyl group, an anthracene-diyl group, a chrysene-diyl group, a pyrene-diyl group, a triphenylene-diyl group, and a perylene-diyl group.

[0151] L ａ Examples of the optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms as the heteroaromatic group include a pyrrole-diyl group, a thiophene-diyl group, a furan-diyl group, an imidazole-diyl group, a thiazole-diyl group, an isothiazole-diyl group, an oxazole-diyl group, an isoxazole-diyl group, a pyridine-diyl group, a pyrimidine-diyl group, a pyrazine-diyl group, a triazine-idyl group, an indole-diyl group, a benzothiophene-diyl group, a benzofuran-diyl group, a benzimidazole-diyl group, a benzothiazole-diyl group, a benzisothiazole-diyl group, a 2,1,3-benzothiadiazole-diyl group, a benzoxazole-diyl group, a benzisoxazole-diyl group, a 2,1,3-benzobenzothiadiazole-diyl group, a benzoisoxazole-diyl group, a 2,1,3-benzobenzobenzoyl group, a benzoiso ... Examples of the alkyl group include benzoxadiazole-diyl group, thienothiophene-diyl group, dithienothiophene-diyl group, benzodithiophene-diyl group, quinoline-diyl group, isoquinoline-diyl group, quinoxaline-diyl group, phenanthroline-diyl group, dibenzothiophene-diyl group, benzothienobenzothiophene-diyl group, dibenzofuran-diyl group, carbazole-diyl group, phenoxazine-diyl group, phenothiazine-diyl group, thianthrene-diyl group, phenylthiophene-diyl group, diphenylthiophene-diyl group, phenylfuran-diyl group, diphenylfuran-diyl group, bithiophene-diyl group, terthiophene-diyl group, phenylpyridine-diyl group, and bipyridine-diyl group.

[0152] <R ａ３１ ~Rａ３４ > R ａ３１ ~R ａ３４ The optionally substituted alkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the optionally substituted alkyl group having 1 to 18 carbon atoms as mentioned above.

[0153] R ａ３１ ~R ａ３４ As the alkenyl group having 1 to 18 carbon atoms, the above-mentioned R ａ１ ~R ａ８ Examples thereof include the same groups as the alkenyl group having 1 to 18 carbon atoms as mentioned above.

[0154] R ａ３１ ~R ａ３４ The cycloalkyl group having 1 to 18 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the cycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0155] R ａ３１ ~R ａ３４ As the bicycloalkyl group having 1 to 18 carbon atoms, the above-mentioned R ａ１ ~R ａ８ Examples include the same groups as the bicycloalkyl group having 1 to 18 carbon atoms as mentioned above.

[0156] R ａ３１ ~R ａ３４ The tricycloalkyl group having 1 to 20 carbon atoms as R ａ１ ~R ａ８ Examples include the same groups as the tricycloalkyl group having 1 to 20 carbon atoms as mentioned above.

[0157] R ａ３１ ~R ａ３４ The optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the aromatic hydrocarbon group include the same groups as the optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms as mentioned above.

[0158] R ａ３１ ~R ａ３４The optionally substituted heteroaromatic group having 3 to 30 carbon atoms as R ａ１ ~R ａ８ Examples of the heteroaromatic group include the same groups as the optionally substituted heteroaromatic group having 3 to 30 carbon atoms as mentioned above.

[0159] The fused ring compound represented by the above formula (4) is preferably a fused ring compound represented by the following formula (4A) or (4B). In formulas (4A) and (4B), ring A, R ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４ represents the rings A and R of the formulas (4) and (6). ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４ represents the same group as

[0160] In the fused ring compounds represented by the above formulas (4), (4A), and (4B), R ａ１ and R ａ２ , R ａ３ and R ａ４ , R ａ５ and R ａ６ , or R ａ７ and R ａ８ and (6) are preferably bonded to each other to form a ring represented by the above formula (6).

[0161] In the fused ring compounds represented by the above formulas (4A) and (4B), it is preferable that ring A represents a structure represented by the following formula (5A) or (5B).

[0162] In formulas (5A) and (5B), X ａ１ ~X ａ３ represents a carbon atom shared with ring B, R ａ１１ ~R ａ１５ , R ａＡ , and L ａ is R in the formula (5). ａ１１ ~R ａ１５ , R ａＡ , and L ａ represents the same group as

[0163] The fused ring compound represented by the above formula (4A) or (4B) is preferably a fused ring compound represented by the following formula (4C).

[0164] In formula (4C), R a３５ ~R a３８ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR a２１ R a２２ , or -OR a２３ represents an adjacent R a３５ ~R a３８ may be bonded to each other to form a ring; R a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a is R in the formulas (4) and (6). a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a represents the same group as

[0165] In the fused ring compound represented by the formula (4C), adjacent R a１ ~R a４ , and R a３１ ~R a３８ are preferably not bonded to each other to form a ring.

[0166] In the fused ring compound represented by the formula (4C), L a is preferably an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond.

[0167] In the fused ring compound represented by the above formula (4C), R a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３８ , and R aＡ each independently represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an octyl group, a decyl group, a dodecyl group, an octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR a２１ R a２２ , and -OR a２３ is a group selected from the group consisting of: a２１ ~R a２３ are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

[0168] In the fused ring compound represented by the above formula (4C), R ａ３１ ~R ａ３８ is preferably a hydrogen atom.

[0169] <Physical Properties of Fused Ring Compound> The preferred HOMO value, band gap, LUMO value, glass transition temperature, and molecular weight of the fused ring compound represented by formula (4) are the same as the preferred HOMO value, band gap, LUMO value, glass transition temperature, and molecular weight of the fused ring compound represented by formula (1) in the above-mentioned <<Material for Photoelectric Conversion Device>>.

[0170] <Preferable Specific Examples of Fused Ring Compounds> Preferable specific examples of the fused ring compound represented by formula (4) are the same as the preferable specific examples of the fused ring compound represented by formula (1) in the above-mentioned <<Material for Photoelectric Conversion Device>>.

[0171] <Uses of Fused Ring Compound> Uses of the fused ring compound represented by formula (4) are the same as those described in <Uses of materials for photoelectric conversion devices> in the above <Materials for photoelectric conversion devices>.

[0172] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0173] [Synthesis Example 1: Synthesis of Compound (Bn-77)]

[0174] (Synthesis of Compound (P-1)) Compound (P-1) was synthesized by the method described in Japanese Patent No. 7127418.

[0175] (Synthesis of Compound (P-2)) Under a nitrogen stream, 1.8 g (5.0 mmol) of compound (P-1), 1.3 g (6.0 mmol) of dibenzothiophene-2-boronic acid, 22 mg (0.1 mmol) of palladium acetate, 111 mg (0.2 mmol) of 1,1'-bis(diphenylphosphino)ferrocene, 50 mL of tetrahydrofuran, and 5 mL of a 2 M aqueous potassium carbonate solution were added to a 200 mL glass vessel, and the mixture was stirred at 75°C for 12 hours. After cooling to room temperature, 50 mL of pure water was added and the mixture was stirred. The precipitated solid was collected by filtration and washed with pure water and methanol, and 2.0 g of a colorless powder of compound (P-2) was isolated (yield 85%).

[0176] (Synthesis of Compound (P-3)) ​​Under a nitrogen atmosphere, 2.0 g (4.3 mmol) of Compound (P-2), 45 mL of dichloromethane, and 5 mL of nitromethane were added to a 200 mL glass container. The solution was cooled to 0°C with stirring, and ferric chloride (FeCl ３ 5.2 g (32 mmol) of compound (P-3) was added to the reaction solution, and the mixture was stirred for 20 minutes at 0°C. Next, 100 mL of methanol was added to the reaction solution, and the mixture was stirred. The precipitated solid was collected by filtration and washed with pure water and methanol, thereby isolating 1.6 g of a pale yellow powder of compound (P-3) (yield 81%).

[0177] (Synthesis of Compound (P-4)) Under a nitrogen stream, 1.6 g (3.4 mmol) of Compound (P-3), 1.2 g (6.8 mmol) of metachloroperbenzoic acid, and 68 mL of dichloromethane were added to a 200 mL glass container and stirred at room temperature for 12 hours. Next, 50 mL of saturated aqueous sodium thiosulfate solution was added to the reaction solution, and the mixture was separated. The organic layer obtained by the separation was concentrated, and the precipitated solid was washed with methanol, thereby isolating 1.5 g of a pale yellow powder of Compound (P-4) (yield 88%).

[0178] (Synthesis of Compound (P-5)) Under a nitrogen stream, 1.5 g (3.0 mmol) of compound (P-4), 0.88 g (3.6 mmol) of N-phenyl-4-biphenylamine, 26 mg (0.06 mmol) of palladium acetate, 24 mg (0.12 mmol) of tri-tert-butylphosphine, 0.43 g (4.5 mmol) of sodium tert-butoxide, and 30 mL of ortho-xylene were added to a 100 mL glass vessel, and the mixture was stirred at 140°C for 24 hours. Next, 40 mL of methanol was added to the reaction solution, and the mixture was stirred. The precipitated solid was collected by filtration and washed with pure water and methanol, and 1.6 g of a pale yellow powder of compound (P-5) was isolated (yield 75%).

[0179] (Synthesis of Compound (Bn-77)) Under a nitrogen stream, 1.6 g (2.3 mmol) of Compound (P-5), 0.43 g (4.6 mmol) of aniline, 14 mL (6.9 mmol) of a 0.5 M toluene solution of potassium bis(trimethylsilyl)amide, and 25 mL of dioxane were added to a 200 mL glass vessel and stirred at 120°C for 12 hours. Next, 50 mL of pure water was added to the reaction solution and stirred. The precipitated solid was collected by filtration, and 0.88 g of a pale yellow powder of Compound (Bn-77) was isolated by recrystallization from toluene (yield: 52%). The resulting Compound (Bn-77) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 9.37 (s, 1H), 8.81 (d, J = 8.8Hz, 1H), 8.77 (dd, J = 8.0, 0.8Hz, 1H), 8.63 (dd, J = 8.0, 0.8Hz, 1H), 8.62 (s, 1H), 8. 58 (dd, J=8.8, 0.8Hz, 1H), 8.41 (ddd, J=8.0, 0.8, 0.8Hz, 1H), 8.28-8.24 (m, 2H), 7.71-7.26 (m, 26H), 7.13-7.07 (m, 1H)

[0180] [Synthesis Example 2: Synthesis of Compound (Cg-79)]

[0181] (Synthesis of Compound (Q-1)) Under a nitrogen stream, 7.6 g (32 mmol) of the compound 1-bromo-2-methoxynaphthalene, 10 g (35 mmol) of 9-phenylcarbazole-2-boronic acid, 144 mg (0.64 mmol) of palladium acetate, 610 mg (1.3 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos), 160 mL of 1,4-dioxane, and 24 mL of a 2 M aqueous potassium phosphate solution were placed in a 500 mL glass vessel and stirred at 100°C for 18 hours. After cooling to room temperature, the mixture was separated with toluene and the resulting organic layer was concentrated. The precipitated solid was dissolved in acetone, and then methanol was added and the mixture was stirred. The precipitated solid was collected by filtration and washed with methanol, resulting in the isolation of 12.2 g of compound (Q-1) (yield 95%).

[0182] (Synthesis of Compound (Q-2)) Under a nitrogen stream, 12 g (30 mmol) of Compound (Q-1), 30 mL of chloroform, and 39 mL of a 1 M solution of boron tribromide in dichloromethane were added to a 100 mL glass container, and the mixture was stirred at room temperature for 16 hours. After adding pure water, the reaction solution was separated with toluene, and the resulting organic layer was concentrated. The precipitated solid was dissolved in acetone, and then methanol was added and the mixture was stirred. The precipitated solid was collected by filtration and washed with methanol, thereby isolating 7.7 g of Compound (Q-2) (yield 67%).

[0183] (Synthesis of Compound (Q-3)) Under a nitrogen stream, 5.6 mL of triethylamine was added dropwise to 7.7 g (20 mmol) of compound (Q-2) and 100 mL of chloroform in a 300 mL glass container at 0°C, and the mixture was stirred at 0°C for 1 hour. Next, 4.9 mL of trifluoromethanesulfonic anhydride was added dropwise to this solution at 0°C, and the mixture was stirred at room temperature for 24 hours. After adding an aqueous sodium hydrogen carbonate solution, the reaction solution was separated with toluene, and the obtained organic layer was concentrated. The precipitated solid was dissolved in toluene, and then methanol was added and the mixture was stirred. The precipitated solid was collected by filtration and washed with methanol, and 8.6 g of compound (Q-3) was isolated (yield 82%).

[0184] (Synthesis of Compound (Q-4)) In a 200 mL glass container, 6.2 g (12 mmol) of Compound (Q-3), 3.7 g (14 mmol) of 4-chloro-[2-(pyrrolidin-1-yldiazenyl)phenyl]boronic acid, and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane (PdCl ２ (dppf) CH ２ Cl ２ 0.20 g (0.24 mmol) of methyl 2-hydroxybenzoate, 4.5 mL of 4M aqueous sodium hydroxide, and 60 mL of 1,4-dioxane were added and stirred at 100°C for 12 hours. After cooling to room temperature, the mixture was separated with toluene and the resulting organic layer was concentrated. The precipitated solid was dissolved in acetone, and then methanol was added and the mixture was stirred. The precipitated solid was collected by filtration and washed with methanol, isolating 2.9 g of compound (Q-4) (yield 46%).

[0185] (Synthesis of Compound (Q-5)) Under a nitrogen stream, 2.9 g (5.0 mmol) of compound (Q-3) and 50 mL of chlorobenzene were added to a 200 mL glass container, and the solution was cooled to 0°C with stirring. 1.9 g (6.5 mmol) of iron tribromide was added, and the mixture was stirred at room temperature for 1 hour. Pure water was added to the reaction solution, and the precipitated solid was filtered off. After separation with chloroform, the resulting organic layer was concentrated. The resulting solid was dissolved in toluene and passed through alumina. The resulting organic solvent was concentrated, and 1.3 g of compound (Q-5) was isolated (yield 54%).

[0186] (Synthesis of Compound (Cg-79)) Under a nitrogen stream, 1.3 g (2.8 mmol) of compound (Q-5), 1.2 g (3.6 mmol) of N,N-bisbiphenylylamine, 12 mg (0.06 mmol) of palladium acetate, 23 mg (0.11 mmol) of tri-tert-butylphosphine, 0.40 g (4.2 mmol) of sodium tert-butoxide, and 28 mL of ortho-xylene were added to a 100 mL glass vessel, and the mixture was stirred at 140°C for 12 hours. After cooling to room temperature, hexane was added to the reaction solution, and the precipitated solid was filtered. The obtained solid was washed with a 1:1 mixed solution of ethyl acetate and hexane, and the solid was filtered, thereby isolating 1.3 g of a yellow powder of compound (Cg-79) (yield 60%). The obtained compound (Cg-79) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 9.03 (d, J = 8.4 Hz, 1H), 8.81 (d, J = 8.0 Hz, 1H), 8.56 (d, J = 8.8, 1H), 8.43 (d, J = 7.6 Hz, 1H), 8. 36 (d, = 9.6Hz, 1H), 8.26 (d, J = 8.8Hz, 1H), 8.24 (d, J = 1.6Hz, 1H), 8.11 (d, J = 8.0Hz, 1H), 8.04 (d, J = 8.8 Hz, 1H), 7.76 (t, J = 8.4Hz, 1H), 7.72-7.67 (m, 10H), 7.53, (t, J = 9.2Hz, 1H), 7.48 (t, J = 7.6Hz, 5H), 7.4 3-7.40 (m, 3H), 7.36 (t, J = 7.2Hz, 2H), 7.32-7.25 (m, 2H), 7.10 (d, J = 8.4Hz, 4H), 6.82 (d, J = 9.6Hz, 1H)

[0187] Comparative Example 1 Compound (X1) represented by the following formula was used as Comparative Example 1. Compound (X1) was synthesized according to the method disclosed in JP-A-2019-034939.

[0188] Comparative Example 2 In Comparative Example 2, a compound (Y1) represented by the following formula was used.

[0189] [Synthesis Example 3: Synthesis of Comparative Compound (Y1)] ​​

[0190] (Synthesis of Compound (y-1)) Compound (y-1) was synthesized according to the method described in JP-A-2016-147846.

[0191] (Synthesis of Compound (y-2)) Under a nitrogen stream, 1.4 g (2.9 mmol) of compound (y-1) and 90 mL of chloroform were added to a 200 mL glass container, and the solution was cooled to 0°C with stirring. 4.7 g (29 mmol) of iron trichloride and 20 mL of nitromethane were added, and the mixture was stirred for 90 minutes. After adding purified water to the reaction solution, the reaction solution was separated with chloroform, and the resulting organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:9), yielding 0.87 g of compound (y-2) (yield 63%).

[0192] (Synthesis of Compound (Y1)) Under a nitrogen stream, 0.87 g (1.8 mmol) of compound (y-2), 0.38 g (2.2 mmol) of diphenylylamine, 21 mg (0.09 mmol) of palladium acetate, 150 mg (0.18 mmol) of tri-tert-butylphosphine, 0.27 g (2.8 mmol) of sodium tert-butoxide, and 10 mL of ortho-xylene were added to a 100 mL glass vessel, and the mixture was stirred at 140°C for 4 hours. After adding an aqueous ammonium chloride solution to the reaction solution, the reaction solution was separated with toluene, and the resulting organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:9), and 0.79 g of a yellow powder of compound (Y1) was isolated (yield: 76%). The resulting compound (Y1) was identified as follows: １ H-NMR was used. １ H-NMR (DMSO-d6) δ (ppm): 8.85-8.68 (m, 5H), 8.34 (s, 1H), 7.78-7.73 (m, 4H), 7.71 (t, J = 8.0Hz, 1H), 7. 68-7.56 (m, 4H), 7.42 (d, J = 9.2Hz, 1H), 7.32 (t, J = 7.2Hz, 4H), 7.26 (d, J = 9.2Hz, 1H), 7.10-6.97 (m, 7H)

[0193] (Glass Transition Temperature) Measurement was performed using a DSC7020 manufactured by Hitachi High-Tech Science Corp. The results are shown in Table 1.

[0194] (HOMO Value) As the HOMO value of the compound obtained in the synthesis example, the HOMO value of a vapor-deposited film of the compound (100 nm thick film formed on a quartz substrate at a rate of 0.10 nm / sec) was measured using an atmospheric photoelectron spectrometer (AC-3) manufactured by Riken Keiki Co., Ltd. The results are shown in Table 7.

[0195]

[0196] <Element Example 1 (see FIG. 1 )> As shown in FIG. 1 , an image pickup element 100 was fabricated as a photoelectric conversion element having a layered structure including a substrate 1, a first electrode 2, a hole-blocking layer 3, a photoelectric conversion layer 4, an electron-blocking layer 5, a hole-transporting layer 6, and a second electrode 7, and the dark current, external quantum efficiency, and responsiveness of the image pickup element were evaluated.

[0197] (Preparation of Substrate 1 and First Electrode 2) A glass substrate with an indium-tin oxide (ITO) transparent electrode, on which a 2 mm wide ITO film (thickness: 110 nm) was patterned in stripes, was prepared as a substrate having a first electrode on its surface. Next, this substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet cleaning.

[0198] (Preparation for Vacuum Deposition) Each layer was vacuum-deposited on the cleaned and surface-treated substrate by a vacuum deposition method, and each layer was laminated.

[0199] First, the glass substrate was placed in a vacuum deposition chamber. －５ The pressure was reduced to Pa. Then, each layer was formed in the following order according to the film formation conditions.

[0200] (Preparation of Hole Blocking Layer 3) Sublimation-purified 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine was deposited at a rate of 0.03 nm / sec to form a film of 10 nm, thereby preparing a hole blocking layer 3.

[0201] (Preparation of Photoelectric Conversion Layer (Light Receiving Layer) 4) A 120 nm thick film was formed by mixing N,N-dimethylquinacridone and C60 in a ratio of 4:1 (mass ratio) to prepare photoelectric conversion layer 4. The film formation rate was 0.15 nm / sec.

[0202] (Preparation of Electron Blocking Layer 5) Compound (Bn-77) was deposited at a rate of 0.10 nm / sec to a thickness of 10 nm to prepare an electron blocking layer 5.

[0203] (Preparation of Hole Transport Layer 6) A compound 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN) was deposited at a rate of 0.10 nm / sec to form a film of 10 nm, thereby preparing a hole transport layer 6.

[0204] (Fabrication of Second Electrode 7) Finally, a metal mask was placed perpendicular to the ITO stripes on the substrate, and the second electrode 7, which is an upper electrode, was formed. Specifically, a silver film was formed to a thickness of 80 nm at a rate of 0.1 nm / sec to fabricate the second electrode 7.

[0205] As a result, the area of ​​4 mm as shown in FIG. ２ The thickness of each film was measured using a stylus film thickness meter (DEKTAK, manufactured by Bruker).

[0206] The device was then sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less by sealing the glass sealing cap and the film-formed substrate (device) with bisphenol F epoxy resin (manufactured by Nagase ChemteX Corporation).

[0207] The image sensor fabricated as described above was evaluated for the current in a dark place (dark current), external quantum efficiency, and response time (responsivity) when a voltage of 2.6 V was applied. The dark current was measured using a Keithley Source Measure Unit 2636B. The external quantum efficiency was measured using a solar cell spectral response measurement device (Soma Optical Co., Ltd.). The wavelength of the irradiated light was 560 nm, and the intensity was 50 μW / cm. ２ The response time was measured by irradiating a light pulse and measuring the time it took for the current value to return to the value before irradiation.

[0208] The dark current, external quantum efficiency, and response time are relative values, with the result of Comparative Example 1 being set as the reference value (1.00). A lower dark current value indicates better performance, a higher external quantum efficiency value indicates better performance, and a lower response time value indicates better performance. The measurement results are shown in Table 2.

[0209] <Element Example 2, Element Comparative Examples 1 and 2> Imaging photoelectric conversion elements of Element Example 2, Element Comparative Example 1, and Element Comparative Example 2 were prepared and evaluated in the same manner as Element Example 1, except that compound (Cg-79), comparative compound (X1), and comparative compound (Y1), respectively, were used instead of compound (Bn-77) in the preparation of electron-blocking layer 5 of Element Example 1. The obtained measurement results are shown in Table 8.

[0210]

[0211] As shown in Table 8, the elements of the examples using the specific materials for photoelectric conversion elements for image sensors had suppressed dark current, high external quantum efficiency, and excellent responsiveness compared to the elements of the comparative examples.

[0212] REFERENCE SIGNS LIST 1 Substrate 2 First electrode 3 Hole blocking layer 4 Photoelectric conversion layer (light receiving layer) 5 Electron blocking layer 6 Hole transport layer 7 Second electrode 100 Imaging element (photoelectric conversion element)

Claims

1. A material for a photoelectric conversion element, comprising a fused ring compound represented by the following formula (1): In formula (1), ring A represents a structure represented by the following formula (2); １ ~R ８ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ or -OR ２３ R ２１ ~R ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R １ ~R ８ may be bonded to each other to form a ring; １ ~R ４ at least one of the groups is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ２１ R ２２ A group having a donor substituent selected from the group consisting of In formula (2), X １ ~X ４ Among them, two adjacent ones represent carbon atoms shared with ring B, and the remaining ones are C-R １５ R １１ ~R １５ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２４ R ２５ or -OR ２６ R ２４ ~R ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R Ａ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; L represents an alkylene group having 1 to 18 carbon atoms, an optionally substituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted divalent heteroaromatic group having 3 to 30 carbon atoms, or a single bond.

2. R １ ~R ８ The material for a photoelectric conversion element according to claim 1 , wherein any two of the following adjacent groups are bonded to each other to form a ring represented by the following formula (3): In formula (3), R ３１ ~R ３４ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ or -OR ２３ represents an adjacent R ３１ ~R ３４ may be bonded to each other to form a ring; the carbon atom of * is R １ ~R ８ represent carbon atoms in the six-membered aromatic ring in formula (1) to which any two adjacent ones of 3. The material for photoelectric conversion elements according to claim 1 or 2, wherein the fused ring compound represented by formula (1) is a fused ring compound represented by the following formula (1A) or (1B): [In formula (1A) and (1B), ring A, R １ ~R ８ , and R ３１ ~R ３４ represents ring A, R in formula (1) and (3). １ ~R ８ , and R ３１ ~R ３４ represents the same group as 4. The material for a photoelectric conversion element according to claim 1, wherein the fused ring compound represented by formula (1) is a fused ring compound represented by any one of the following formulas (1C) to (1E): [In formulas (1C) to (1E), R １ ~R ８ , R １１ ~R １５ , R Ａ and L is R in the formulas (1) and (2). １ ~R ８ , R １１ ~R １５ , R Ａ and L represents the same group as L; provided that an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ２１ R ２２ The group having a donor substituent selected from R １ ~R ４ and R ５ ~R ８ It may be at least one of the following.

5. R １ and R ２ , R ３ and R ４ , R ５ and R ６ , or R ７ and R ８ The material for a photoelectric conversion element according to claim 2 or 4, wherein any one of the above is bonded to each other to form a ring represented by the formula (3).

6. The material for a photoelectric conversion element according to claim 3, wherein ring A in the fused ring compound represented by formula (1) has a structure represented by the following formula (2A) or (2B): [In formulas (2A) and (2B), X １ ~X ３ represents a carbon atom shared with ring B; R １１ ~R １５ , R Ａ and L is R in the formula (2). １１ ~R １５ , R Ａ and represents the same group as L.

7. The material for photoelectric conversion elements according to claim 2 or 6, wherein the fused ring compound represented by formula (1) is a fused ring compound represented by formula (1F): [In formula (1F), R ３５ ~R ３８ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ２１ R ２２ or -OR ２３ represents an adjacent R ３５ ~R ３８ may be bonded to each other to form a ring; R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and L is R in the formulas (1) and (3). １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３４ , R Ａ and represents the same group as L.

8. Adjacent R １ ~R ４ , and R ３１ ~R ３８ The material for a photoelectric conversion element according to claim 7 , wherein are not bonded to each other to form a ring.

9. The material for a photoelectric conversion element according to claim 8, wherein L is an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond.

10. R １ ~R ４ , R １１ ~R １５ , R ３１ ~R ３８ , and R Ａ each independently represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, an n-decyl group, an n-dodecyl group, an n-octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR ２１ R ２２ and -OR ２３ R is a group selected from the group consisting of ２１ ~R ２３ are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

11. R ３１ ~R ３８ The material for a photoelectric conversion element according to claim 10 , wherein is a hydrogen atom.

12. An organic thin film comprising the material for a photoelectric conversion device according to any one of claims 1 to 11.

13. A photoelectric conversion element comprising the material for photoelectric conversion elements according to any one of claims 1 to 11.

14. A photoelectric conversion element comprising the material for photoelectric conversion elements according to any one of claims 1 to 11 in a photoelectric conversion layer.

15. A photoelectric conversion device comprising the material for photoelectric conversion devices according to any one of claims 1 to 11 in a hole transport layer or an electron blocking layer.

16. The material for photoelectric conversion elements according to any one of claims 1 to 11, which is used in photoelectric conversion elements for image sensors.

17. A fused ring compound represented by the following formula (4): In formula (4), ring A represents a structure represented by the following formula (5); ａ１ ~R ａ８ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ or -OR ａ２３ R ａ２１ ~R ａ２３ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａ１ ~R ａ８ may be bonded to each other to form a ring; provided that R ａ１ ~R ａ４ at least one of the groups is an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, and -NR ａ２１ R ａ２２ R is a group having a donor substituent selected from ａ１ ~R ａ８ Any two adjacent ones of the above are bonded to each other to form a ring represented by the following formula (6): In formula (5), X ａ１ ~X ａ４ Among them, two adjacent ones represent carbon atoms shared with ring B, and the remaining ones are C-R ａ１５ R ａ１１ ~R ａ１５ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２４ R ａ２５ or -OR ａ２６ R ａ２４ ~R ａ２６ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; R ａＡ represents an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms or an optionally substituted heteroaromatic group having 3 to 30 carbon atoms; ａ represents an alkylene group having 1 to 18 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may be substituted, a divalent heteroaromatic group having 3 to 30 carbon atoms which may be substituted, or a single bond. In formula (6), R ａ３１ ~R ａ３４ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR ａ２１ R ａ２２ or -OR ａ２３ represents an adjacent R ａ３１ ~R ａ３４ may be bonded to each other to form a ring; the carbon atom of * is R ａ１ ~R ａ８ represent carbon atoms in the 6-membered aromatic ring in formula (4) to which any two adjacent ones of 18. The fused ring compound according to claim 17, wherein the fused ring compound represented by formula (4) is represented by the following formula (4A) or (4B): [In formula (4A) and (4B), ring A, R ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４ represents ring A, R in formula (4) and (6). ａ１ ~R ａ８ , and R ａ３１ ~R ａ３４ represents the same group as 19. The fused ring compound according to claim 18, wherein ring A represents a structure represented by the following formula (5A) or (5B): [In formulas (5A) and (5B), X ａ１ ~X ａ３ represents a carbon atom shared with ring B; R ａ１１ ~R ａ１５ , R ａＡ , and L ａ is R in the formula (5). ａ１１ ~R ａ１５ , R ａＡ , and L ａ represents the same group as 20. The fused ring compound according to claim 19, wherein the fused ring compound represented by formula (4A) or (4B) is represented by the following formula (4C): [In formula (4C), R a３５ ~R a３８ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 18 carbon atoms, an alkenyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, a bicycloalkyl group having 1 to 18 carbon atoms, a tricycloalkyl group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an optionally substituted heteroaromatic group having 3 to 30 carbon atoms, -NR a２１ R a２２ or -OR a２３ represents an adjacent R a３５ ~R a３８ may be bonded to each other to form a ring; R a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a is R in the formulas (4) and (6). a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３４ , R aＡ , and L a represents the same group as 21. The fused ring compound represented by formula (4C) has adjacent R a１ ~R a４ , and R a３１ ~R a３８ The fused ring compound of claim 20 , wherein:

22. L a The fused ring compound according to claim 21 , wherein is an optionally substituted phenylene group, an optionally substituted biphenylene group, an optionally substituted terphenylene group, an optionally substituted naphthylene group, or a single bond.

23. R a１ ~R a４ , R a１１ ~R a１５ , R a３１ ~R a３８ , and R aＡ each independently represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, an n-decyl group, an n-dodecyl group, an n-octadecyl group, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, an optionally substituted dibenzothienyl group, -NR a２１ R a２２ and -OR a２３ R is a group selected from the group consisting of a２１ ~R a２３ are each independently a group selected from the group consisting of a hydrogen atom, an adamantyl group, a diamantyl group, an optionally substituted phenyl group, an optionally substituted biphenylyl group, an optionally substituted terphenylyl group, an optionally substituted naphthyl group, an optionally substituted fluorenyl group, an optionally substituted spirobifluorenyl group, an optionally substituted benzofluorenyl group, an optionally substituted phenanthryl group, an optionally substituted fluoranthenyl group, an optionally substituted triphenylenyl group, an optionally substituted anthryl group, an optionally substituted pyrenyl group, an optionally substituted carbazolyl group, an optionally substituted dibenzofuranyl group, and an optionally substituted dibenzothienyl group.

24. R a３１ ~R a３８ The fused ring compound according to claim 23, wherein is a hydrogen atom.

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