WO2023042878A1 - Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé - Google Patents

Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé Download PDF

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WO2023042878A1
WO2023042878A1 PCT/JP2022/034535 JP2022034535W WO2023042878A1 WO 2023042878 A1 WO2023042878 A1 WO 2023042878A1 JP 2022034535 W JP2022034535 W JP 2022034535W WO 2023042878 A1 WO2023042878 A1 WO 2023042878A1
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良 藤原
和平 金子
寛記 杉浦
健浩 山根
康智 米久田
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富士フイルム株式会社
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    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to photoelectric conversion elements, imaging elements, optical sensors, and compounds.
  • Patent Document 1 discloses a compound represented by the following formula as a material applied to a photoelectric conversion element.
  • photoelectric conversion elements are required to have small variations in dark current and excellent photoelectric conversion efficiency.
  • small variations in dark current means that a plurality of photoelectric conversion elements were produced under the same conditions (e.g., material, content, manufacturing method, etc.) and the dark current of each photoelectric conversion element was measured.
  • the ratio of the highest dark current among all photoelectric conversion elements to the lowest dark current among all photoelectric conversion elements (highest dark current among all photoelectric conversion elements/dark current among all photoelectric conversion elements (minimum value of ) is small. In other words, when the variation in dark current is small, it is possible to stably obtain photoelectric conversion elements having equivalent dark current performance.
  • An object of the present invention is to provide a photoelectric conversion element with small variations in dark current and excellent photoelectric conversion efficiency. Another object of the present invention is to provide an imaging device, an optical sensor, and a compound.
  • the present inventors have found that the above problems can be solved by using a compound having a predetermined structure for a photoelectric conversion film, and have completed the present invention.
  • the compound represented by the above formula (1) is the above formula (11) to the above formula (13), the above formula (17) to the above formula (19), the above formula (23) to the above formula (26) and the above formula (29)
  • the photoelectric conversion device according to [2] which contains a compound represented by any one of the above formulas (32).
  • the compound represented by the above formula (1) is the above formula (11), the above formula (12), the above formula (17), the above formula (18), the above formula (23), the above formula (24), the above formula (29) and the photoelectric conversion device according to [3], containing the compound represented by any one of the above formulas (30).
  • D contains at least one ring selected from the group consisting of furan rings, thiophene rings, thiazole rings and oxazole rings.
  • [8] The photoelectric conversion device according to any one of [1] to [7], wherein the compound represented by formula (1) has a molecular weight of 900 or less.
  • the present invention it is possible to provide a photoelectric conversion element with small variations in dark current and excellent photoelectric conversion efficiency. Also, imaging devices, photosensors and compounds can be provided.
  • a numerical range represented by "to” means a range including the numerical values before and after “to” as lower and upper limits.
  • the hydrogen atom may be a protium atom or a deuterium atom (eg, a double hydrogen atom, etc.).
  • the photoelectric conversion element of the present invention is a photoelectric conversion element having a conductive film, a photoelectric conversion film and a transparent conductive film in this order, wherein the photoelectric conversion film is a compound represented by formula (1) (hereinafter, " Also referred to as "specific compounds").
  • the specific compound having both the group represented by A and the group represented by D is said to have excellent properties such as crystallinity of the specific compound, so that the variation in dark current is small and the photoelectric conversion efficiency is also excellent. I'm guessing.
  • the fact that at least one of the effects of a smaller variation in dark current and a more excellent photoelectric conversion efficiency is obtained is also referred to as "the effect of the present invention is more excellent”.
  • FIG. 1 shows a schematic cross-sectional view of one embodiment of the photoelectric conversion element of the present invention.
  • a photoelectric conversion element 10a shown in FIG. 1 includes a conductive film (hereinafter also referred to as a “lower electrode”) 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and an upper electrode.
  • a transparent conductive film (hereinafter, also referred to as an “upper electrode”) 15 that functions as an electrode is laminated in this order.
  • FIG. 2 shows a configuration example of another photoelectric conversion element.
  • FIGS. 1 and 2 has a structure in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are laminated on a lower electrode 11 in this order.
  • the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be appropriately changed according to the application and characteristics.
  • the photoelectric conversion element 10a or 10b light is preferably incident on the photoelectric conversion film 12 via the upper electrode 15. As shown in FIG. Moreover, when using the photoelectric conversion element 10a or 10b, a voltage can be applied. In this case, it is preferable that the lower electrode 11 and the upper electrode 15 constitute a pair of electrodes, and a voltage of 1 ⁇ 10 ⁇ 5 to 1 ⁇ 10 7 V/cm is applied between the pair of electrodes. From the viewpoint of performance and power consumption, the applied voltage is more preferably 1 ⁇ 10 ⁇ 4 to 1 ⁇ 10 7 V/cm, further preferably 1 ⁇ 10 ⁇ 3 to 5 ⁇ 10 6 V/cm.
  • the photoelectric conversion element 10a or 10b is used as an optical sensor, or incorporated in an imaging element, a voltage can be applied by a similar method. As will be described in detail later, the photoelectric conversion element 10a or 10b can be suitably applied to image pickup device applications.
  • the form of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.
  • a photoelectric conversion element has a photoelectric conversion film.
  • a photoelectric conversion film contains a specific compound as a photoelectric conversion material.
  • a specific compound is a compound represented by Formula (1).
  • AD (1) In formula (1), A represents a group represented by formula (A-1). D represents a group represented by any one of formulas (2) to (4). In addition, two A represent the same group.
  • * represents a bonding position.
  • RB represents a hydrogen atom or an optionally substituted alkyl group.
  • C 1 represents a cyclic group containing two or more carbon atoms as ring member atoms and optionally having a substituent.
  • R Z1 represents a hydrogen atom or a substituent.
  • R Z2 and R Z3 each independently represent a cyano group, —SO 2 R Z4 , —COOR Z5 or —COR Z6 .
  • R Z4 to R Z6 each independently represent an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.
  • RB represents a hydrogen atom or an optionally substituted alkyl group.
  • the alkyl group may be linear, branched or cyclic, preferably linear.
  • the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-2.
  • Examples of the substituent that the alkyl group may have include the substituent W.
  • RB is preferably a hydrogen atom.
  • C 1 represents a cyclic group containing two or more carbon atoms as ring member atoms and optionally having a substituent.
  • C 1 is a cyclic group containing, as ring member atoms, the carbon atom to which Z 1 in formula (A-1) is bonded and the carbon atom adjacent to the carbon atom to which R 1 B is bonded.
  • C 1 may be either a monocyclic ring or a polycyclic ring, and the polycyclic ring may be either a non-fused ring or a condensed ring.
  • C 1 can be either aromatic or non-aromatic.
  • the total carbon number of C 1 is preferably 2-30, more preferably 5-15.
  • the above total carbon number includes the carbon atom to which Z 1 in formula (A-1) is bonded, the carbon atom adjacent to the carbon atom to which R 1 is bonded, and the substituents that C 1 may have.
  • C 1 is preferably a 5-membered ring, a 6-membered ring, or a condensed ring combining them.
  • the condensed ring preferably consists of 1 to 4 monocyclic rings, more preferably 1 to 3 monocyclic rings.
  • C 1 may have a heteroatom.
  • Heteroatoms include, for example, halogen atoms, nitrogen atoms, sulfur atoms, oxygen atoms, selenium atoms, tellurium atoms, phosphorus atoms, silicon atoms and boron atoms.
  • the heteroatom that C 1 may have may be either as a ring member atom or as a non-ring member atom (for example, a substituent, etc.).
  • the heteroatom that C 1 may have is preferably a nitrogen atom, a sulfur atom or an oxygen atom, more preferably a nitrogen atom or an oxygen atom.
  • RN represents a hydrogen atom or a substituent.
  • the number of heteroatoms that C 1 may have is preferably 0 to 10, more preferably 0 to 5, even more preferably 1 to 4.
  • C 1 has a heteroatom, it preferably has a group containing a heteroatom.
  • C 1 may have a substituent.
  • substituent W preferably a halogen atom, a cyano group, a trifluoromethyl group, an alkyl group, an aryl group or a heteroaryl group, more preferably a halogen atom, a cyano group or a trifluoromethyl group.
  • C 1 preferably does not have a ring as a substituent from the viewpoint of excellent photoelectric conversion efficiency. In the above case, the crystallinity of the specific compound can be improved.
  • the ring may be either an aromatic ring or a non-aromatic ring.
  • That C 1 does not have a ring as a substituent means that it does not have a ring as a part or all of the substituents. In other words, it does not have ring-containing substituents and ring groups. Specifically, C 1 preferably does not have a group containing an aromatic ring such as a benzyl group, a phenyl group and a naphthyl group as a substituent. It is permissible for C 1 itself to be a cyclic group.
  • a ring that is usually used as an acidic nucleus in merocyanine dyes is preferred.
  • the following (a) to (s) are mentioned.
  • pyrazolinone nucleus for example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, and 1-(2-benzothiazolyl)-3-methyl-2 - pyrazolin-5-ones.
  • Isoxazolinone nucleus examples include 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one.
  • oxindole nucleus examples include 1-alkyl-2,3-dihydro-2-oxindole.
  • (e) 2,4,6-trioxohexahydropyrimidine nucleus for example, barbituric acid or 2-thiobarbituric acid and derivatives thereof.
  • Examples of the above derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl; 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl and 1,3-dibutyl; -diphenyl, 1,3-di(p-chlorophenyl), 1,3-diaryl compounds such as 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1- such as 1-ethyl-3-phenyl aryl and 1,3-diheteroaryl such as 1,3-di(2-pyridyl).
  • rhodanine 2-thio-2,4-thiazolidinedione nucleus: for example, rhodanine and its derivatives.
  • examples of the above derivatives include 3-methylrhodanine, 3-ethylrhodanine, 3-alkylrhodanine such as 3-arylrhodanine, 3-arylrhodanine such as 3-phenylrhodanine, and 3-(2 -pyridyl) rhodanine and 3-heteroaryl rhodanine.
  • 2-thio-2,4-oxazolidinedione (2-thio-2,4-(3H,5H)-oxazolidinedione nucleus: for example, 3-ethyl-2-thio-2,4-oxazolidinedione; be done.
  • Thianaphthenone nucleus examples thereof include 3(2H)-thianaphthenone-1,1-dioxide.
  • 2-thio-2,5-thiazolidinedione core Examples include 3-ethyl-2-thio-2,5-thiazolidinedione.
  • 2,4-thiazolidinedione nuclei examples include 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione and 3-phenyl-2,4-thiazolidinedione.
  • Thiazolin-4-one nucleus includes, for example, 4-thiazolinone and 2-ethyl-4-thiazolinone.
  • 2,4-imidazolidinedione (hydantoin) core examples include 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione.
  • 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidine Dione is mentioned.
  • imidazolin-5-one nucleus for example, 2-propylmercapto-2-imidazolin-5-one.
  • 3,5-pyrazolidinedione nucleus examples include 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione.
  • benzothiophen-3(2H)-one nucleus for example, benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, and dioxobenzothiophen-3(2H)-one mentioned.
  • indanone nuclei examples include 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone. be done.
  • Benzofuran-3-(2H)-one nucleus examples include benzofuran-3-(2H)-one.
  • R Z1 represents a hydrogen atom or a substituent.
  • R Z2 and R Z3 each independently represent a cyano group, —SO 2 R Z4 , —COOR Z5 or —COR Z6 .
  • R Z4 to R Z6 each independently represent an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.
  • Z 1 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.
  • Examples of the substituent represented by R Z1 include groups exemplified for the substituent W.
  • R Z2 and R Z3 are preferably cyano groups.
  • R Z4 to R Z6 are preferably alkyl groups which may have a substituent.
  • substituents that the alkyl group, aryl group and heteroaryl group represented by R Z4 to R Z6 may have include groups exemplified for the substituent W.
  • the group represented by formula (A-1) is preferably a group represented by formula (A-2).
  • R 1 B represents a hydrogen atom or an optionally substituted alkyl group.
  • R Z1 represents a hydrogen atom or a substituent.
  • R Z2 and R Z3 each independently represent a cyano group, —SO 2 R Z4 , —COOR Z5 or —COR Z6 .
  • R Z4 to R Z6 each independently represent an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.
  • R Z21 to R Z23 each independently represent a cyano group or —COOR Z25 .
  • R Z24 and R Z25 each independently represent a hydrogen atom or a substituent.
  • R Y1 to R Y6 each independently represent a hydrogen atom or a substituent.
  • L represents a single bond or -NR L -.
  • RL represents a hydrogen atom or a substituent.
  • R B and Z 1 have the same meanings as R B and Z 1 in formula (A-1), respectively, and preferred embodiments are also the same.
  • R Z21 to R Z23 each independently represent a cyano group or —COOR Z25 .
  • R Z24 and R Z25 each independently represent a hydrogen atom or a substituent.
  • R Z21 to R Z23 are preferably cyano groups.
  • substituents represented by R Z24 and R Z25 include groups exemplified for the substituent W, an alkyl group optionally having a substituent, an aryl optionally having a substituent An optionally substituted heteroaryl group is preferred, and an optionally substituted alkyl group is more preferred. Further, from the viewpoint of excellent photoelectric conversion efficiency, it is also preferable that the substituents represented by R 24 and R 225 do not have a ring as a substituent. In the above case, the crystallinity of the specific compound can be improved. The significance of having no ring as a substituent is as described above.
  • the above alkyl group may be linear, branched or cyclic.
  • the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-3.
  • the aryl group and the heteroaryl group may be either monocyclic or polycyclic.
  • the aryl group and the heteroaryl group preferably have 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms.
  • Examples of substituents that the alkyl group, the aryl group, and the heteroaryl group may have include the groups exemplified for the substituent W.
  • R Y1 to R Y6 each independently represent a hydrogen atom or a substituent.
  • the substituents represented by R Y1 to R Y6 are an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group. is preferred, and an optionally substituted alkyl group is more preferred.
  • R Y3 to R Y5 are preferably alkyl groups which may have a substituent, more preferably unsubstituted alkyl groups.
  • the substituents represented by R Y1 to R Y6 do not have a cyclic group as a substituent.
  • the crystallinity of the specific compound can be improved.
  • the significance of having no ring as a substituent is as described above.
  • the alkyl group, the aryl group, and the heteroaryl group include alkyl groups, aryl groups, and heteroaryl groups as substituents represented by R Z24 and R Z25 .
  • R Y1 and R Y2 preferably combine to form a ring, and R Y1 and R Y2 combine to form a benzene ring. is more preferable.
  • R L represents a single bond or -NR L -.
  • RL represents a hydrogen atom or a substituent.
  • the substituent represented by R L include groups exemplified for the substituent W, an optionally substituted alkyl group, an optionally substituted aryl group, or a substituted
  • An optionally substituted heteroaryl group is preferred, an optionally substituted alkyl group is more preferred, and an unsubstituted alkyl group is preferred.
  • the substituent represented by RL does not have a cyclic group as a substituent. In the above case, the crystallinity of the specific compound can be improved.
  • the significance of having no ring as a substituent is as described above.
  • the alkyl group, the aryl group, and the heteroaryl group include alkyl groups, aryl groups, and heteroaryl groups as substituents represented by R Z4 and R Z5 above.
  • a ring formed by combining -ZYL- and two carbon atoms specified in formula (1) is a five-membered ring Or a combination that forms a 6-membered ring is preferred. Further, as described above, the 5-membered ring or the 6-membered ring may be condensed with another ring (preferably a benzene ring) to form a condensed ring.
  • the group represented by formula (A-1) is more preferably a group represented by formula (C-1) or a group represented by formula (C-2).
  • * represents a bonding position.
  • RB represents a hydrogen atom or an optionally substituted alkyl group.
  • R c11 represents a hydrogen atom or a substituent.
  • R c12 and R c13 each independently represent a cyano group, —SO 2 R c14 , —COOR c15 or —COR c16 .
  • R c14 to R c16 each independently represent an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.
  • C3 represents an aromatic ring containing at least two carbon atoms and optionally having a substituent.
  • * represents a bonding position.
  • RB represents a hydrogen atom or an optionally substituted alkyl group.
  • R c21 represents a hydrogen atom or a substituent.
  • R c22 and R c23 each independently represent a cyano group, —SO 2 R c24 , —COOR c25 or —COR c26 .
  • R c24 to R c26 each independently represent an optionally substituted alkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group.
  • R c1 and R c2 each independently represent a hydrogen atom or a substituent.
  • R 1 B has the same meaning as R 1 B in formula (A-1), and preferred embodiments are also the same.
  • X c1 and X c2 each have the same meaning as Z 1 in formula (A-1), and the preferred embodiments are also the same.
  • C3 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
  • the number of carbon atoms in the aromatic ring is preferably 5-30, more preferably 5-12, even more preferably 6-8.
  • the above number of carbon atoms is a number including two carbon atoms specified in the formula.
  • the above aromatic ring may be either monocyclic or polycyclic.
  • the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, preferably an aromatic hydrocarbon ring.
  • the aromatic ring is preferably a benzene ring, a naphthalene ring, an anthracene ring or a pyrene ring, more preferably a benzene ring.
  • Examples of the substituent that the aromatic ring may have include the groups exemplified for the substituent W above.
  • D represents a group represented by any one of formulas (2) to (4).
  • D is preferably a group represented by formula (2) or a group represented by formula (3).
  • Ar 1 represents a group represented by any one of formulas (7) to (10). Two Ar 1 's represent the same group.
  • one of Ar 2 and Ar 3 represents a group represented by any one of formulas (7) to (10), and the other represents a group represented by any one of formulas (5) to (10). represents the group to be Two Ar 3 's represent the same group.
  • Ar 2 and Ar 3 may be the same or different.
  • one of Ar 4 and Ar 5 represents a group represented by any one of formulas (7) to (10), and the other represents any of formulas (5) and (6). represents the group to be Two Ar 4 's represent the same group, and two Ar 5 's represent the same group.
  • Ar 1 is preferably a group represented by formula (10).
  • One of Ar 2 and Ar 3 preferably represents a group represented by formula (10), and the other preferably represents a group represented by either formula (5) or (10). It is preferable that one of Ar 4 and Ar 5 represents a group represented by formula (10) and the other represents a group represented by formula (5).
  • the total number of monocyclic rings of one Ar 2 and two Ar 3 is often 4 to 6, preferably 4 to 5, more preferably 4. Specifically, when one Ar 2 represents a benzene ring and two Ar 3 represent a naphthalene ring (there are two monocyclic benzene rings), the total number of monocyclic rings constituting formula (3) is 5.
  • R A5 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X61 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A6 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • R A7 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X81 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A8 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X91 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A9 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X 101 and X 102 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A10 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • the R A5 may be the same or different.
  • X 61 is preferably an oxygen atom or a sulfur atom.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • R A6 may be the same or different.
  • R A7 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • R A7 preferably represents a hydrogen atom.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • R A7 may be the same or different.
  • X81 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A8 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X81 is preferably an oxygen atom or a sulfur atom, more preferably a sulfur atom.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • R A8 is preferably a hydrogen atom. When multiple R A8 are present, R A8 may be the same or different.
  • X91 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A9 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X 91 is preferably an oxygen atom or a sulfur atom, more preferably a sulfur atom.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • R A9 is preferably a hydrogen atom. When multiple RA9s are present, the RA9s may be the same or different.
  • X 101 and X 102 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A10 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • X 101 and X 102 are preferably an oxygen atom or a sulfur atom, more preferably a sulfur atom.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • R A10 is preferably a hydrogen atom. When multiple RA10s are present, the RA10s may be the same or different.
  • D preferably contains at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring and an oxazole ring, and contains at least one ring selected from the group consisting of a thiophene ring and a thiazole ring. is more preferred.
  • Another preferred embodiment of D preferably contains at least one ring selected from the group consisting of a thiophene ring, a furan ring and a thiazole ring, and at least one ring selected from the group consisting of a thiophene ring and a furan ring. It is more preferable to include
  • the specific compound it is preferable to include a compound represented by any one of formulas (11) to (38), and the effects of the present invention are more excellent. 17) to formula (19), formula (23) to formula (26) and formula (29) to formula (32). ), Formula (17), Formula (18), Formula (23), Formula (24), Formula (29), and Formula (30). It is particularly preferable to contain the compound represented by or the compound represented by formula (12).
  • groups represented by the same notation in formulas (11) to (38) represent the same group. Groups represented by the same notation represent the same group, for example, in X n (n represents an integer of 1 or more) in the following formula, a plurality of X n with the same n It means that they are the same group.
  • two X 111 represent the same group
  • two Y 111 represent the same group
  • two A 11 represent the same group
  • two Z 11 represent the same is meant to represent the group of
  • the multiple R An may be the same or different.
  • X 111 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A11 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 11 represents a group represented by formula (5) or a group represented by formula (6).
  • a 11 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA11 may be the same or different.
  • X121 and X122 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • RA12 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 12 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA12 may be the same or different.
  • X131 and X132 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • RA13 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 13 represents a group represented by formula (5) or a group represented by formula (6).
  • a 13 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA13 may be the same or different.
  • X141 and X142 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A14 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 14 represents a group represented by formula (5) or a group represented by formula (6).
  • a 14 represents a group represented by formula (A-1).
  • X 151 to X 153 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A15 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 15 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA15 may be the same or different.
  • X161 and X162 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A16 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 16 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA16 may be the same or different.
  • RA17 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 17 represents a group represented by formula (5) or a group represented by formula (6).
  • a 17 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA17 may be the same or different.
  • R A18 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 18 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA18 may be the same or different.
  • R A19 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 19 represents a group represented by formula (5) or a group represented by formula (6).
  • a 19 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA19 may be the same or different.
  • RA20 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 20 represents a group represented by formula (5) or a group represented by formula (6).
  • a 20 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA20 may be the same or different.
  • RA21 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 21 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA21 may be the same or different.
  • X221 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA22 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 22 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA22 may be the same or different.
  • X231 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA23 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 23 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group. However, RA23 may be the same or different.
  • X241 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A24 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 24 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA24 may be the same or different.
  • X251 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA25 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 25 represents a group represented by formula (5) or a group represented by formula (6).
  • a 25 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA25 may be the same or different.
  • X261 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A26 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 26 represents a group represented by formula (5) or a group represented by formula (6).
  • a 26 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA26 may be the same or different.
  • X271 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA27 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z27 represents a group represented by formula (5) or a group represented by formula (6).
  • a 27 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group. However, RA27 may be the same or different.
  • X281 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A28 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 28 represents a group represented by formula (5) or a group represented by formula (6).
  • a 28 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA28 may be the same or different.
  • X291 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A29 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 29 represents a group represented by formula (A-1). In addition, groups represented by the same notation represent the same group. However, RA29 may be the same or different.
  • X 301 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A30 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 30 represents a group represented by formula (A-1). In addition, groups represented by the same notation represent the same group. However, RA30 may be the same or different.
  • X 311 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA31 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 31 represents a group represented by formula (5) or a group represented by formula (6).
  • a 31 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group. However, RA31 may be the same or different.
  • X 321 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A32 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 32 represents a group represented by formula (5) or a group represented by formula (6).
  • a 32 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA32 may be the same or different.
  • X 331 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A33 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 33 represents a group represented by formula (5) or a group represented by formula (6).
  • a 33 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA33 may be the same or different.
  • X 341 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A34 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • Z 34 represents a group represented by formula (5) or a group represented by formula (6).
  • a 34 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA34 may be the same or different.
  • X 351 and X 352 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • RA35 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 35 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA35 may be the same or different.
  • X 361 and X 362 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • R A36 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 36 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA36 may be the same or different.
  • X 371 represents an oxygen atom, a sulfur atom or a selenium atom.
  • RA37 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 37 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA37 may be the same or different.
  • X 381 represents an oxygen atom, a sulfur atom or a selenium atom.
  • R A38 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
  • a 38 represents a group represented by formula (A-1).
  • groups represented by the same notation represent the same group.
  • RA38 may be the same or different.
  • X 111 in formula (11) is preferably a group represented by X 101 or X 102 in formula (10).
  • Y 111 is preferably a group represented by Y 101 or Y 102 in formula (10).
  • Z 11 is preferably a group represented by the above formula (5).
  • X 121 and X 122 in formula (12) are preferably groups represented by X 101 or X 102 in formula (10).
  • Y 121 and Y 122 are preferably groups represented by Y 101 or Y 102 in formula (10).
  • X 131 and X 132 in formula (13) are preferably groups represented by X 101 or X 102 in formula (10).
  • Y 131 and Y 132 are preferably groups represented by Y 101 or Y 102 in formula (10).
  • Z 13 is preferably a group represented by the above formula (5).
  • X 141 and X 142 in formula (14) are preferably groups represented by X 101 or X 102 in formula (10).
  • Y 141 and Y 142 are preferably Y 101 or Y 102 in formula (10).
  • Z 14 is preferably a group represented by the above formula (5).
  • X 151 to X 153 in formula (15) are preferably groups represented by X 101 or X 102 in formula (10).
  • Y 151 to Y 153 are preferably groups represented by Y 101 or Y 102 in formula (10).
  • X 161 and X 162 in formula (16) are preferably groups represented by X 101 or X 102 in formula (10).
  • Y 161 and Y 162 are preferably groups represented by Y 101 or Y 102 in formula (10).
  • Y 163 to Y 165 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • Y 171 to Y 173 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • Z 17 is preferably a group represented by the above formula (5).
  • Y 181 to Y 186 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • Y 191 to Y 196 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • Z 19 is preferably a group represented by the above formula (5).
  • Y 201 to Y 206 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • Y 211 to Y 219 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • X 221 is preferably a group represented by X 101 or X 102 in formula (10).
  • Y 227 is preferably a group represented by Y 101 or Y 102 in formula (10).
  • Y 221 to Y 226 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • X 231 is preferably a group represented by X 81 in formula (8).
  • Y 231 to Y 234 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • X 241 is preferably a group represented by X 91 in formula (9).
  • Y 241 to Y 244 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • X 251 is preferably a group represented by X 81 in formula (8).
  • Y 251 to Y 254 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Z 25 is preferably a group represented by the above formula (5).
  • X 261 is preferably a group represented by X 91 in formula (9).
  • Y 261 to Y 264 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • Z 26 is preferably a group represented by the above formula (5).
  • X 271 is preferably a group represented by X 81 in formula (8).
  • Y 271 to Y 274 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Z 27 is preferably a group represented by the above formula (5).
  • X 281 is preferably a group represented by X 91 in formula (9).
  • Y 281 to Y 284 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • Z 28 is preferably a group represented by the above formula (5).
  • X 291 is preferably a group represented by X 91 in formula (9).
  • Y 291 to Y 294 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • X 301 is preferably a group represented by X 81 in formula (8).
  • Y 301 to Y 304 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • X 311 is preferably a group represented by X 91 in formula (9).
  • Y 311 to Y 314 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • Z 31 is preferably a group represented by the above formula (5).
  • X 321 is preferably a group represented by X 81 in formula (8).
  • Y 321 to Y 324 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Z 32 is preferably a group represented by the above formula (5).
  • X 331 is preferably a group represented by X 91 in formula (9).
  • Y 331 to Y 334 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • Z 33 is preferably a group represented by the above formula (5).
  • X 341 is preferably a group represented by X 81 in formula (8).
  • Y 341 to Y 344 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Z 34 is preferably a group represented by the above formula (5).
  • X 351 is preferably a group represented by X 81 in formula (8).
  • X 352 is preferably a group represented by X 101 or X 102 in formula (10).
  • Y 351 to Y 354 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Y 355 is preferably a group represented by Y 101 or Y 102 in formula (10).
  • X 361 is preferably a group represented by X 81 in formula (8).
  • X 362 is preferably a group represented by X 101 or X 102 in formula (10).
  • Y 361 to Y 364 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Y 365 is preferably a group represented by Y 101 or Y 102 in formula (10).
  • X 371 is preferably a group represented by X 81 in formula (8).
  • Y 371 to Y 374 are preferably groups represented by Y 81 to Y 84 in formula (8).
  • Y 375 to Y 377 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • X 381 is preferably a group represented by X 91 in formula (9).
  • Y 381 to Y 384 are preferably groups represented by Y 91 to Y 94 in formula (9).
  • Y 385 to Y 387 are preferably groups represented by Y 71 to Y 76 in formula (7).
  • substituent W examples include halogen atoms (fluorine, chlorine, bromine and iodine atoms), alkyl groups, alkenyl groups (including cycloalkenyl groups and bicycloalkenyl groups), alkynyl groups, aryl groups, and heterocyclic rings.
  • acyloxy groups include heteroaryl groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups , amino group (including anilino group), ammonio group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group , arylthio group, heterocyclicthio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbam
  • the substituent W may be further substituted with a substituent W.
  • a substituent W when the substituent W is an alkyl group, it may be an alkyl group further substituted with a halogen atom and having a halogen atom.
  • substituent W include those described in paragraph [0023] of JP-A-2007-234651, the contents of which are incorporated herein.
  • the alkyl group, the aryl group, and the heteroaryl group that the specific compound may have may be any of the alkyl group X, the aryl group X, and the heteroaryl group X, respectively.
  • alkyl group X The number of carbon atoms in the alkyl group X is preferably 1-15, more preferably 1-10, and even more preferably 1-6.
  • the alkyl group X may be linear, branched or cyclic. Examples of alkyl group X include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, n-hexyl group and cyclopentyl group.
  • the alkyl group X may be, for example, a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have a cyclic structure of these as a partial structure.
  • substituents that the alkyl group X may have include groups exemplified for the substituent W, an aryl group (preferably having 6 to 18 carbon atoms, more preferably 6 carbon atoms), a heteroaryl group (preferably has 5 to 18 carbon atoms, more preferably 5 to 6 carbon atoms) or a halogen atom (preferably a fluorine atom or a chlorine atom).
  • the aryl group X preferably has 6 to 18 carbon atoms.
  • the aryl group X may be either monocyclic or polycyclic.
  • As the aryl group X for example, a phenyl group, a naphthyl group, an anthryl group or a fluorenyl group is preferable, and a phenyl group is more preferable.
  • Examples of the substituent that the aryl group X may have include groups exemplified for the substituent W, and an optionally substituted alkyl group (preferably having 1 to 10 carbon atoms) is preferable, and methyl or i-propyl groups are more preferred.
  • the heteroatom possessed by the heteroaryl group X is preferably a sulfur atom, an oxygen atom or a nitrogen atom.
  • the heteroaryl group X may be monocyclic or polycyclic.
  • the heteroaryl group X preferably has 3 to 18 carbon atoms, more preferably 3 to 5 carbon atoms.
  • the number of heteroatoms possessed by the heteroaryl group X is preferably 1-10, more preferably 1-4, even more preferably 1-2.
  • the number of ring members of the heteroaryl group X is preferably 3-8, more preferably 5-7, even more preferably 5-6.
  • heteroaryl group X examples include furyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pteridinyl, pyrazinyl, quinoxalinyl, pyrimidinyl, quinazolyl, pyridazinyl, and cinnolinyl.
  • substituent that the heteroaryl group X may have include groups exemplified for the substituent W, and an alkyl group or
  • the structure of D in the specific compound is linear and the structure of A is planar in that the crystallinity of the specific compound is improved and the photoelectric conversion efficiency is more excellent.
  • the structure of D having a linear structure and the structure of A having a planar molecular shape include a specific compound that satisfies the following requirement A and requirement B.
  • Requirement A In formula (A-1), R B and R Z1 to R Z3 do not have an aromatic ring group or an alicyclic group, and C 1 does not have an aromatic ring group or an alicyclic group as a substituent. It is permissible for C1 itself to be an aromatic ring group or an alicyclic group.
  • Requirement B In formulas (2) to (4), Ar 1 to Ar 5 represent a group represented by formula (5) or a group represented by formula (10). As the specific compound, a compound represented by any one of formulas (11) to (15) is preferable. However, Z 11 , Z 13 and Z 14 each represent a group represented by formula (5), and A 11 to A 15 are limited to cases where Requirement A is satisfied.
  • Specific compounds include, for example, compounds obtained by combining D and A below. Specific examples of D are shown below. In the formula, * represents a binding position.
  • the molecular weight of the specific compound is not particularly limited, it is preferably 200 or more, more preferably 400 or more.
  • the upper limit is preferably 2000 or less, more preferably 1200 or less, and even more preferably 900 or less. If the molecular weight is 900 or less, the vapor deposition temperature does not become high, and decomposition of the compound hardly occurs. If the molecular weight is 400 or more, the glass transition point of the deposited film does not become low, and the heat resistance of the photoelectric conversion element is improved.
  • the specific compound has an absolute value of ionization potential in a single film of 5.0 to 6.4 eV in terms of stability when used as a p-type organic semiconductor and energy level matching with an n-type organic semiconductor. It is preferably from 5.5 to 6.2 eV, even more preferably from 5.7 to 6.0 eV.
  • the maximum absorption wavelength of the specific compound is preferably in the wavelength range of 400 to 700 nm, more preferably in the wavelength range of 450 to 650 nm, even more preferably in the wavelength range of 450 to 600 nm.
  • the maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) after adjusting the concentration of the absorption spectrum of the specific compound so that the absorbance is 0.5 to 1.0.
  • solvent chloroform
  • a particular compound may be purified if desired.
  • the method for purifying the specific compound is not particularly limited, sublimation purification is preferred.
  • the content of the specific compound in the photoelectric conversion film is preferably 15 to 75% by volume, and 20 to 60% by volume. % is more preferred, and 25 to 50% by volume is even more preferred.
  • the specific compound is particularly useful as a material for photoelectric conversion films used in imaging devices, optical sensors, or photoelectric cells.
  • the specific compound often functions as a dye in the photoelectric conversion film.
  • the specific compound can also be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic agent material.
  • the photoelectric conversion film preferably contains an n-type organic semiconductor in addition to the specific compound.
  • the n-type organic semiconductor is a compound different from the above specific compound.
  • An n-type organic semiconductor is an acceptor organic semiconductor material (compound), and refers to an organic compound having a property of easily accepting electrons. That is, the n-type organic semiconductor refers to an organic compound having a larger electron affinity when two organic compounds are used in contact with each other. That is, any organic compound can be used as the acceptor organic semiconductor as long as it is an organic compound having an electron-accepting property.
  • n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives and fluoranthene derivatives, etc.); 5- to 7-membered heterocyclic compounds having at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline) , quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole and thiazole
  • fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred.
  • Fullerenes include, for example, fullerene C60, fullerene C70, fullerene C76, fullerene C78, fullerene C80, fullerene C82, fullerene C84, fullerene C90, fullerene C96, fullerene C240, fullerene C540 and mixed fullerene.
  • Fullerene derivatives include, for example, compounds in which substituents are added to the above fullerenes. The above substituent is preferably an alkyl group, an aryl group or a heterocyclic group. As the fullerene derivative, compounds described in JP-A-2007-123707 are preferred.
  • organic dye may be used as the n-type organic semiconductor.
  • organic dyes include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarium dyes, croconium dyes, Azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, Examples include acridine dyes,
  • the molecular weight of the n-type organic semiconductor is preferably 200-1200, more preferably 200-900.
  • the maximum absorption wavelength of the n-type organic semiconductor is preferably in the range of 400-650 nm, more preferably in the range of 420-550 nm, and even more preferably in the range of 450-500 nm.
  • the method for measuring the maximum absorption wavelength the method for measuring the maximum absorption wavelength of the specific compound can be used.
  • the photoelectric conversion film preferably has a bulk heterostructure formed by mixing the specific compound and the n-type organic semiconductor.
  • a bulk heterostructure is a layer in which a specific compound and an n-type organic semiconductor are mixed and dispersed in a photoelectric conversion film.
  • a photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. The bulk heterostructure is described in detail in paragraphs [0013] to [0014] of JP-A-2005-303266.
  • the difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.
  • the n-type organic semiconductor may be used singly or in combination of two or more.
  • the content of the specific compound with respect to the total content of the specific compound and the n-type organic semiconductor is preferably 20 to 80% by volume, more preferably 40 to 80% by volume.
  • the content of the specific compound is preferably 15 to 75% by volume, more preferably 35 to 75% by volume.
  • the photoelectric conversion film is substantially composed of a specific compound, an n-type organic semiconductor, and, if necessary, a p-type organic semiconductor.
  • the total content of the specific compound, the n-type organic semiconductor and the p-type organic semiconductor is 95% by mass or more with respect to the total mass of the photoelectric conversion film. The upper limit is often 100% by mass or less.
  • the photoelectric conversion film preferably contains a p-type organic semiconductor in addition to the specific compound. Also, the photoelectric conversion film preferably contains a specific compound, an n-type organic semiconductor and a p-type organic semiconductor.
  • the p-type organic semiconductor is a compound different from the above specific compound.
  • a p-type organic semiconductor is a donor organic semiconductor material (compound), and refers to an organic compound having a property of easily donating electrons. In other words, the p-type organic semiconductor refers to an organic compound with a smaller ionization potential when two organic compounds are used in contact with each other.
  • Examples of p-type organic semiconductors include triarylamine compounds (eg, N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), compounds described in paragraphs [0128] to [0148] of JP-A-2011-228614, JP-A-2011-176259
  • pyrazoline compounds e.g.
  • Examples of p-type organic semiconductors include compounds having ionization potentials lower than those of n-type organic semiconductors. If this condition is satisfied, organic dyes exemplified as n-type organic semiconductors can be used. Examples of p-type organic semiconductors include the following compounds.
  • the difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.
  • a p-type organic semiconductor may be used individually by 1 type, and may be used 2 or more types.
  • a photoelectric conversion film containing a specific compound is a non-luminous film and has characteristics different from those of an organic electroluminescent device (OLED: Organic Light Emitting Diode).
  • OLED Organic Light Emitting Diode
  • a non-luminous film means a film having a luminous quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.
  • the maximum absorption wavelength of the photoelectric conversion film is preferably in the wavelength range of 500 to 600 nm, more preferably in the wavelength range of 520 to 580 nm, and even more preferably in the wavelength range of 530 to 565 nm.
  • Another preferred embodiment of the maximum absorption wavelength of the photoelectric conversion film is preferably in the wavelength range of 440 to 600 nm, more preferably in the wavelength range of 440 to 580 nm, and further preferably in the wavelength range of 440 to 565 nm. preferable.
  • the method for measuring the maximum absorption wavelength the method for measuring the maximum absorption wavelength of the specific compound can be used.
  • Examples of a method for forming the photoelectric conversion film include a dry film forming method.
  • Examples of dry film formation methods include vapor deposition (especially vacuum vapor deposition), sputtering, ion plating, MBE (Molecular Beam Epitaxy) and other physical vapor deposition methods, and plasma polymerization and other CVD (Chemical Vapor Deposition) method is mentioned, and a vacuum deposition method is preferable.
  • the manufacturing conditions such as the degree of vacuum and the vapor deposition temperature can be set according to conventional methods.
  • the thickness of the photoelectric conversion film is preferably 10-1000 nm, more preferably 50-800 nm, even more preferably 50-500 nm, and particularly preferably 50-300 nm.
  • the photoelectric conversion element preferably has electrodes.
  • the electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, the upper electrode 15 is preferably transparent to light to be detected. Materials constituting the upper electrode 15 include, for example, antimony or fluorine-doped tin oxide (ATO: Antimony Tin Oxide, FTO: Fluorine doped Tin Oxide), tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO).
  • ATO Antimony Tin Oxide
  • FTO Fluorine doped Tin Oxide
  • ITO indium tin oxide
  • Conductive metal oxides such as Indium Tin Oxide (IZO) and Indium Zinc Oxide (IZO); Metal thin films such as gold, silver, chromium and nickel; Mixtures or laminates of these metals and conductive metal oxides and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and conductive metal oxides are preferred from the viewpoint of high conductivity and transparency.
  • IZO Indium Tin Oxide
  • IZO Indium Zinc Oxide
  • Metal thin films such as gold, silver, chromium and nickel
  • Mixtures or laminates of these metals and conductive metal oxides and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and conductive metal oxides are preferred from the viewpoint of high conductivity and transparency.
  • a solid-state imaging device incorporating the photoelectric conversion device according to the present embodiment may have a sheet resistance of 100 to 10000 ⁇ / ⁇ , and the degree of freedom in the range of film thickness that can be reduced is large.
  • An increase in light transmittance is preferable because it increases the light absorption in the photoelectric conversion film and increases the photoelectric conversion performance.
  • the thickness of the upper electrode 15 is preferably 5 to 100 nm, more preferably 5 to 20 nm.
  • the lower electrode 11 may be transparent or reflect light without transparency.
  • Materials constituting the lower electrode 11 include, for example, tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • metals such as gold, silver, chromium, nickel, titanium, tungsten and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN), etc.); and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene and polypyrrole.
  • a method for forming the electrodes can be appropriately selected according to the electrode material. Specific examples include wet methods such as printing methods and coating methods; physical methods such as vacuum deposition methods, sputtering methods and ion plating methods; and chemical methods such as CVD and plasma CVD methods.
  • wet methods such as printing methods and coating methods
  • physical methods such as vacuum deposition methods, sputtering methods and ion plating methods
  • chemical methods such as CVD and plasma CVD methods.
  • the electrode material is ITO
  • methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (such as a sol-gel method), and application of an indium tin oxide dispersion can be used.
  • the photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
  • the intermediate layer include a charge blocking film. If the photoelectric conversion element has this film, the characteristics (photoelectric conversion efficiency, responsiveness, etc.) of the obtained photoelectric conversion element are more excellent.
  • Charge blocking films include, for example, electron blocking films and hole blocking films.
  • the electron blocking film is a donor organic semiconductor material (compound), and the above p-type organic semiconductor can be used.
  • Polymeric materials can also be used as the electron blocking film. Examples of polymeric materials include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene and diacetylene, and derivatives thereof.
  • the electron blocking film may be composed of a plurality of films.
  • the electron blocking film may be composed of an inorganic material.
  • an inorganic material has a higher dielectric constant than an organic material. Therefore, when an inorganic material is used for an electron blocking film, a large voltage is applied to the photoelectric conversion film, resulting in a high photoelectric conversion efficiency.
  • inorganic materials that can serve as an electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, and indium oxide. Copper, indium silver oxide and iridium oxide are mentioned.
  • the hole-blocking film is an acceptor organic semiconductor material (compound), and the above n-type organic semiconductor can be used. Note that the hole blocking film may be composed of a plurality of films.
  • Examples of methods for manufacturing the charge blocking film include a dry film formation method and a wet film formation method.
  • Dry film-forming methods include, for example, a vapor deposition method and a sputtering method.
  • the vapor deposition method may be either a physical vapor deposition (PVD) method or a chemical vapor deposition (CVD) method, preferably a physical vapor deposition method such as a vacuum vapor deposition method.
  • Examples of wet film-forming methods include inkjet methods, spray methods, nozzle printing methods, spin coating methods, dip coating methods, casting methods, die coating methods, roll coating methods, bar coating methods, and gravure coating methods. From the viewpoint of patterning, the inkjet method is preferable.
  • the film thickness of the charge blocking film is preferably 3 to 200 nm, more preferably 5 to 100 nm, and still more preferably 5 to 30 nm.
  • the photoelectric conversion element may further have a substrate.
  • Substrates include, for example, semiconductor substrates, glass substrates, and plastic substrates. Although the position of the substrate is not particularly limited, the conductive film, the photoelectric conversion film and the transparent conductive film are usually laminated in this order on the substrate.
  • the photoelectric conversion element may further have a sealing layer.
  • the performance of the photoelectric conversion material may be remarkably deteriorated due to the presence of deterioration factors such as water molecules. Therefore, the entire photoelectric conversion film is covered with a sealing layer such as dense ceramics such as metal oxides, metal nitrides or metal oxynitrides, or diamond-like carbon (DLC) that does not allow water molecules to permeate.
  • a sealing layer such as dense ceramics such as metal oxides, metal nitrides or metal oxynitrides, or diamond-like carbon (DLC) that does not allow water molecules to permeate.
  • the above deterioration can be prevented by sealing.
  • the sealing layer is described, for example, in paragraphs [0210] to [0215] of JP-A-2011-082508, the contents of which are incorporated herein.
  • An example of an application of a photoelectric conversion element is an imaging element.
  • An image pickup device is a device that converts optical information of an image into an electrical signal.
  • a plurality of photoelectric conversion devices are arranged in a matrix on the same plane. is converted into an electric signal, and the electric signal can be sequentially output to the outside of the image sensor for each pixel. Therefore, one pixel is composed of one or more photoelectric conversion elements and one or more transistors.
  • the photoelectric conversion element include, for example, photoelectric cells and optical sensors, and the photoelectric conversion element of the present invention is preferably used as an optical sensor.
  • the photoelectric conversion element may be used alone, or may be used as a line sensor in which the photoelectric conversion elements are linearly arranged or a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.
  • the present invention also includes inventions relating to specific compounds.
  • the photoelectric conversion element is composed of a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B and an upper electrode 15.
  • An electron blocking film 16A (thickness: 30 nm) was formed by depositing by a heating vapor deposition method.
  • the evaluation compound, the p-type organic semiconductor material, and the n-type organic semiconductor material shown in Table 1 are vapor-deposited so as to have the component ratio shown in Table 1, thereby forming the photoelectric conversion film 12 having a bulk heterostructure. formed. Furthermore, the following compound (F-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form the upper electrode 15 (transparent conductive film) (thickness: 10 nm).
  • an aluminum oxide (Al 2 O 3 ) layer is formed thereon by an ALCVD (Atomic Layer Chemical Vapor Deposition) method to obtain a photoelectric conversion element. was made.
  • Relative ratio of dark current (Highest dark current value among 10 photoelectric conversion elements)/(Lowest dark current value among 10 photoelectric conversion elements)
  • Relative ratio of photoelectric conversion efficiency (photoelectric conversion efficiency for light with a wavelength of 460 nm in each example or comparative example) / (photoelectric conversion efficiency for light with a wavelength of 460 nm in Comparative Example 1-1)
  • D The relative ratio of photoelectric conversion efficiency is 0.8 or more and less than 1.0
  • the relative ratio of photoelectric conversion efficiency is less than 0.8
  • Table 1 shows the evaluation results. In the table, each notation indicates the following.
  • the columns of “Formula (11) to Formula (38)” show the formulas to which the specific compounds correspond.
  • the column “Number of monocyclic rings of D” indicates the total number of monocyclic rings constituting D. The definition of the total number of monocyclic rings constituting D is as described above.
  • the column “Number of X groups in D” indicates the number of X groups that D has. X groups are as described above.
  • the "Number of Y groups in A” column shows the number of Y groups that A has. The Y group is as described above.
  • the number of Y groups above indicates the number of Y groups in any one of the two A's possessed by the specific compound.
  • the number of Y groups above indicates the number of Y groups in one A, not the total number of Y groups in a specific compound. Specifically, the total number of Y groups in compound (B-1) is four, and the above “number of Y groups in A" is two.
  • the structure of D is linear in the specific compound, and the structure of A indicates that the molecular shape has planarity. If B, other molecules Indicates shape.
  • the linear shape is as described above.
  • the photoelectric conversion element of the present invention can achieve the effects of the present invention. It was confirmed that the effect of the present invention is more excellent when the number of monocyclic rings of D is 4 to 5 (preferably 4) (Examples 1-1 to 1-45 and Examples 1-46 to 1- 53). Further, from the same comparison, the specific compound is any of formula (11) ⁇ formula (13), formula (17) ⁇ formula (19), formula (23) ⁇ formula (26) and formula (29) ⁇ formula (32) A compound represented by (preferably formula (11), formula (12), formula (17), formula (18), formula (23), formula (24), formula (29) and formula (30) It was confirmed that the effect of the present invention is more excellent when the compound represented by any of the above is included.

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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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Abstract

La présente invention concerne un élément de conversion photoélectrique, un élément d'imagerie, un capteur optique et un composé dans lequel des variations de courant d'obscurité sont faibles et une efficacité de conversion photoélectrique exceptionnelle est obtenue. L'élément de conversion photoélectrique selon la présente invention comprend un film électroconducteur, un film de conversion photoélectrique et un film électroconducteur transparent dans l'ordre indiqué, le film de conversion photoélectrique contenant un composé représenté par la formule (1).
PCT/JP2022/034535 2021-09-17 2022-09-15 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé WO2023042878A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014026244A1 (fr) * 2012-08-17 2014-02-20 Commonwealth Scientific And Industrial Research Organisation Dispositifs optoélectroniques photoactifs et à transistors
JP2018510845A (ja) * 2015-01-27 2018-04-19 ソニー株式会社 有機フォトダイオード中の有機光電変換層の材料としてのスクアラインおよびチオフェン系分子
CN113200958A (zh) * 2021-04-25 2021-08-03 国家纳米科学中心 一种邻苯二甲酸酯类有机光电化合物及其制备方法和应用
WO2021221108A1 (fr) * 2020-04-30 2021-11-04 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé

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Publication number Priority date Publication date Assignee Title
WO2014026244A1 (fr) * 2012-08-17 2014-02-20 Commonwealth Scientific And Industrial Research Organisation Dispositifs optoélectroniques photoactifs et à transistors
JP2018510845A (ja) * 2015-01-27 2018-04-19 ソニー株式会社 有機フォトダイオード中の有機光電変換層の材料としてのスクアラインおよびチオフェン系分子
WO2021221108A1 (fr) * 2020-04-30 2021-11-04 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé
CN113200958A (zh) * 2021-04-25 2021-08-03 国家纳米科学中心 一种邻苯二甲酸酯类有机光电化合物及其制备方法和应用

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