WO2022091799A1 - 光電変換素子、撮像素子、光センサ、化合物 - Google Patents

光電変換素子、撮像素子、光センサ、化合物 Download PDF

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WO2022091799A1
WO2022091799A1 PCT/JP2021/038036 JP2021038036W WO2022091799A1 WO 2022091799 A1 WO2022091799 A1 WO 2022091799A1 JP 2021038036 W JP2021038036 W JP 2021038036W WO 2022091799 A1 WO2022091799 A1 WO 2022091799A1
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atom
formula
photoelectric conversion
independently represent
oxygen atom
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French (fr)
Japanese (ja)
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昌樹 森田
良 藤原
寛記 杉浦
康智 米久田
飛翼 中田
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Fujifilm Corp
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Fujifilm Corp
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Priority to KR1020237013714A priority Critical patent/KR102801743B1/ko
Priority to CN202180072838.XA priority patent/CN116406366B/zh
Priority to JP2022558999A priority patent/JP7664280B2/ja
Publication of WO2022091799A1 publication Critical patent/WO2022091799A1/ja
Priority to US18/307,789 priority patent/US20240114781A1/en
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a photoelectric conversion element, an image pickup element, an optical sensor, and a compound.
  • Patent Document 1 discloses a photoelectric conversion element for an image sensor including a photoelectric conversion unit having one or more organic thin film layers containing a predetermined compound.
  • Another object of the present invention is to provide a photoelectric conversion element having excellent photoelectric conversion efficiency. Another object of the present invention is to provide an image pickup device, an optical sensor, and a compound related to the photoelectric conversion element.
  • n11 represents 1 or 2.
  • n12 and n13 independently represent 0 or 1, respectively. However, at least one of n12 and n13 represents 1.
  • Ar 11 represents a fused polycyclic aromatic ring group consisting of a combination of one or more aromatic rings selected from the group consisting of a thiophene ring, a benzene ring, a furan ring, and a selenophene ring.
  • the number of rings of the condensed polycyclic aromatic ring group is 3 to 4.
  • the condensed polycyclic aromatic ring group may have a substituent.
  • Ar 14 and Ar 15 each independently represent an aryl group which may have a substituent or a heteroaryl group which may have a substituent.
  • Ar 12 and Ar 13 independently represent any of the groups represented by the formulas (2) to (4). In equations (2) to (4), * A and * B represent the bonding position.
  • X 21 and X 22 independently represent a sulfur atom, an oxygen atom, or a selenium atom, respectively.
  • X 31 represents a sulfur atom, an oxygen atom, or a selenium atom.
  • R indicates a hydrogen atom or a substituent.
  • X 41 represents a sulfur atom, an oxygen atom, or a selenium atom.
  • R indicates a hydrogen atom or a substituent.
  • R and RA each independently represent a hydrogen atom or a substituent.
  • Z 21 to Z 23 independently represent a sulfur atom, an oxygen atom, or a selenium atom.
  • RA represents a hydrogen atom or a substituent.
  • Z 31 and Z 32 independently represent a sulfur atom, an oxygen atom, or a selenium atom, respectively.
  • RA represents a hydrogen atom or a substituent.
  • R and RA each independently represent a hydrogen atom or a substituent.
  • R and RA each independently represent a hydrogen atom or a substituent.
  • Z 61 to Z 64 independently represent a sulfur atom, an oxygen atom, or a selenium atom.
  • RA represents a hydrogen atom or a substituent.
  • Z 21 to Z 23 independently represent a sulfur atom or an oxygen atom, respectively.
  • Z 31 and Z 32 independently represent a sulfur atom or an oxygen atom, respectively.
  • Z 43 and Z 44 represents a sulfur atom or an oxygen atom
  • one of Z 51 and Z 52 represents a sulfur atom or an oxygen atom
  • One of Z 53 and Z 54 represents a sulfur atom or an oxygen atom
  • n11 represents 1 or 2.
  • n12 and n13 independently represent 0 or 1, respectively.
  • n12 and n13 represents 1.
  • Ar 11 represents a fused polycyclic aromatic ring group consisting of a combination of one or more aromatic rings selected from the group consisting of a thiophene ring, a benzene ring, a furan ring, and a selenophene ring.
  • the number of rings of the condensed polycyclic aromatic ring group is 3 to 4.
  • the condensed polycyclic aromatic ring group may have a substituent.
  • Ar 14 and Ar 15 each independently represent an aryl group which may have a substituent or a heteroaryl group which may have a substituent.
  • Ar 12 and Ar 13 independently represent any of the groups represented by the formulas (2) to (4).
  • X 21 and X 22 independently represent a sulfur atom, an oxygen atom, or a selenium atom, respectively.
  • R represents a hydrogen atom or a substituent. However, at least one of Y 21 and Y 22 represents a nitrogen atom.
  • X 31 represents a sulfur atom, an oxygen atom, or a selenium atom.
  • R indicates a hydrogen atom or a substituent.
  • X 41 represents a sulfur atom, an oxygen atom, or a selenium atom.
  • R indicates a hydrogen atom or a substituent.
  • the compound according to [14], wherein the group represented by Ar 11 in the above formula (1) is any of the groups represented by the formulas (A1) to (A6).
  • * represents a binding position.
  • Z 13 and Z 14 represents a sulfur atom, an oxygen atom, or a selenium atom
  • R and RA each independently represent a hydrogen atom or a substituent.
  • Z 21 to Z 23 independently represent a sulfur atom, an oxygen atom, or a selenium atom.
  • RA represents a hydrogen atom or a substituent.
  • Z 31 and Z 32 independently represent a sulfur atom, an oxygen atom, or a selenium atom, respectively.
  • RA represents a hydrogen atom or a substituent.
  • R and RA each independently represent a hydrogen atom or a substituent.
  • R and RA each independently represent a hydrogen atom or a substituent.
  • Z 61 to Z 64 independently represent a sulfur atom, an oxygen atom, or a selenium atom.
  • RA represents a hydrogen atom or a substituent.
  • Z 21 to Z 23 independently represent a sulfur atom or an oxygen atom, respectively.
  • Z 31 and Z 32 independently represent a sulfur atom or an oxygen atom, respectively.
  • Z 53 and Z 54 represents a sulfur atom or an oxygen atom
  • Z 61 to Z 64 each independently represent a sulfur atom or an oxygen atom, and are the compounds according to [15].
  • n11 is 1
  • Ar 11 is a group represented by the above formula (A5) in the above formula (1).
  • X 21 and X 22 independently represent a sulfur atom or an oxygen atom, respectively.
  • X 31 represents a sulfur atom or an oxygen atom.
  • the present invention it is possible to provide a photoelectric conversion element having excellent photoelectric conversion efficiency. Further, according to the present invention, it is possible to provide an image pickup device, an optical sensor, and a compound related to the photoelectric conversion element.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the numerical range represented by using “-” means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • the hydrogen atom may be a light hydrogen atom (ordinary hydrogen atom) or a heavy hydrogen atom (double hydrogen atom or the like).
  • 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, and the photoelectric conversion film is a compound represented by the formula (1) (hereinafter referred to as a compound). , Also referred to as "specific compound").
  • a compound represented by the formula (1)
  • specific compound also referred to as "specific compound”.
  • the specific compound is between the mother nucleus, which is a condensed polycyclic aromatic ring group (Ar 11 ) acting as a donor, and an aryl group or a heteroaryl group (Ar 14 and / or Ar 15 ) acting as an acceptor. It has a predetermined linking group (Ar 12 and / or Ar 13 ).
  • the linking group is a condensed polycyclic aromatic heterocyclic group having a structure in which predetermined 5-membered rings or 5-membered rings and 6-membered rings are fused, and the bonding position with respect to a donor and / or an acceptor is also predetermined. It is specified to be a position.
  • the donor is sandwiched by the acceptor, and further, by having a predetermined linking group as described above between the donor and the acceptor, the specific compound is particularly light having a wavelength of 400 to 550 nm. Has good absorbency.
  • the specific compound has the above-mentioned structure, the charge transport property in the specific compound, between the specific compounds, or between the specific compound and other components becomes good, and the photoelectric conversion efficiency of the photoelectric conversion element is improved. It is presumed that (especially the photoelectric conversion efficiency for light having a wavelength of 400 to 550 nm) is improved. Further, the photoelectric conversion element of the present invention also suppresses the electric field strength dependence of the photoelectric conversion efficiency.
  • the specific compound has the above-mentioned linking group, so that the specific compound can have a packing structure preferable for charge transport in the photoelectric conversion film and can maintain good charge transport even under a low voltage. I'm guessing.
  • the fact that the photoelectric conversion efficiency of the photoelectric conversion element is more excellent and / or that the electric field strength dependence of the photoelectric conversion efficiency is further suppressed is also referred to as "the effect of the present invention is more excellent".
  • FIG. 1 shows a schematic cross-sectional view of an embodiment of the photoelectric conversion element of the present invention.
  • the photoelectric conversion element 10a shown in FIG. 1 includes a conductive film (hereinafter, also referred to as a lower electrode) 11 that functions as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound described later, and an upper electrode. It has a structure in which a functioning transparent conductive film (hereinafter, also referred to as an upper electrode) 15 is laminated in this order.
  • FIG. 2 shows a configuration example of another photoelectric conversion element.
  • FIGS. 1 and 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are laminated in this order on a lower electrode 11.
  • 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 depending on the application and characteristics.
  • the photoelectric conversion element 10a it is preferable that light is incident on the photoelectric conversion film 12 via the upper electrode 15. Further, when the photoelectric conversion element 10a (or 10b) is used, a voltage can be applied. In this case, it is preferable that the lower electrode 11 and the upper electrode 15 form 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 voltage application method it is preferable to apply the voltage so that the electron blocking film 16A side becomes the cathode and the photoelectric conversion film 12 side becomes the anode in FIGS. 1 and 2.
  • a voltage can be applied by the same method.
  • the photoelectric conversion element 10a (or 10b) can be suitably applied to an image sensor application.
  • the photoelectric conversion film is a film containing a specific compound.
  • the specific compound will be described in detail.
  • n11 represents 1 or 2.
  • Ar 11 is a condensed polycyclic aromatic ring group composed of four rings (for example, Ar 11 is represented by the formulas (A3) to (A6) described later.
  • n11 is preferably 1.
  • n12 and n13 independently represent 0 or 1, respectively. However, at least one of n12 and n13 represents 1. It is preferable that both n12 and n13 are 1.
  • Ar 11 is a fused polycycle consisting of a combination of one or more (for example, 1 to 4) aromatic rings selected from the group consisting of a thiophene ring, a benzene ring, a furan ring, and a selenophene ring. Represents an aromatic ring group.
  • Ar 11 is a condensed polycyclic aromatic ring group composed of a combination of one or more (for example, 1 to 3) aromatic rings selected from the group consisting of a thiophene ring, a benzene ring, and a furan ring. preferable.
  • the number of rings of the condensed polycyclic aromatic ring group is 3 to 4.
  • the condensed polycyclic aromatic ring group preferably contains at least one (for example, 1 to 4, preferably 2) thiophene ring or furan ring, and more preferably contains a thiophene ring.
  • the condensed polycyclic aromatic ring group may or may not have a substituent.
  • a halogen atom fluorine atom or the like
  • the number of substituents of the condensed polycyclic aromatic ring group is, for example, 1 to 6. When n 11 represents 2, it is also preferable that the two Ar 11s are the same.
  • Ar 11 in the formula (1) is preferably any of the groups represented by the following formulas (A1) to (A6), and is preferably any of the formulas (A3) to (A6). It is more preferably any of the represented groups, and even more preferably the group represented by the formula (A5). Above all, in the formula (1), it is particularly preferable that n11 is 1 and Ar 11 is a group represented by the formula (A5). Further, it is also preferable that (Ar 11 ) n11 in the formula (1) is a group in which the groups represented by the same formulas in the formulas (A1) to (A6) are connected to each other, for example, two formulas. It is also preferable that the groups represented by (A1) are linked to each other.
  • one of Z 11 and Z 12 represents a sulfur atom (-S-), an oxygen atom (-O-), or a selenium atom (-Se-), and the other of Z 11 and Z 12 .
  • Represents -CR .
  • R and RA each independently represent a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituents that can be represented by R and RA are preferably a halogen atom (fluorine atom or the like) or an alkyl group that may further have a halogen atom (for example, 1 to 2 carbon atoms), and a halogen atom (fluorine atom or the like). Is more preferable.
  • Z 21 to Z 23 independently represent a sulfur atom, an oxygen atom, or a selenium atom, and preferably represent a sulfur atom or an oxygen atom.
  • RA represents a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituent that can be represented by RA is preferably a halogen atom (fluorine atom or the like).
  • Z 31 and Z 32 independently represent a sulfur atom, an oxygen atom, or a selenium atom, and preferably represent a sulfur atom or an oxygen atom.
  • RA represents a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituent that can be represented by RA is preferably a halogen atom (fluorine atom or the like).
  • R and RA each independently represent a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituent that can be represented by R and RA is preferably a halogen atom (fluorine atom or the like).
  • R and RA each independently represent a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituent that can be represented by R and RA is preferably a halogen atom (fluorine atom or the like).
  • Z 61 to Z 64 independently represent a sulfur atom, an oxygen atom, or a selenium atom, and preferably represent a sulfur atom or an oxygen atom.
  • RA represents a hydrogen atom or a substituent.
  • the substituent that can be represented by RA is preferably a halogen atom (fluorine atom or the like).
  • Ar 14 and Ar 15 each independently represent an aryl group which may have a substituent or a heteroaryl group which may have a substituent.
  • the aryl group may be monocyclic or polycyclic, and the number of ring-membered atoms is preferably 6 to 15.
  • the aryl group is preferably a phenyl group, a naphthyl group, or an anthrasenyl group, and more preferably a phenyl group.
  • the heteroaryl group may be monocyclic or polycyclic, and the number of ring-membered atoms is preferably 5 to 15.
  • the number of heteroatoms contained in the aryl group is preferably 1 to 5, more preferably 1.
  • hetero atom examples include a nitrogen atom, an oxygen atom, a sulfur atom, and a selenium atom.
  • the heteroaryl group is a pyridinyl group, a pyrazil group, a pyrimidyl group, a pyridadyl group, a triazil group, a quinolyl group, a quinoxalyl group, a quinazolyl group, a phthalazyl group, a synnolyl group, an isoquinolyl group, a pteridyl group, an acrizyl group, a phenadyl group and a phenanthrolyl group.
  • Tetrazolyl group, pyrazolyl group, imidazolyl group, or thiazolyl group is preferable.
  • an alkyl group which may further have a substituent or a halogen atom (fluorine atom or the like) is preferable.
  • the alkyl group may be linear or branched, and the number of carbon atoms is preferably 1 to 3. Examples of the substituent that the alkyl group may further have include a halogen atom (fluorine atom and the like).
  • the alkyl group is preferably an alkyl halide group (fluoroalkyl group or the like), and more preferably a perhalogenated alkyl group (perfluoroalkyl group or the like).
  • Ar 14 and Ar 15 are preferably aryl groups having an alkyl halide group or a halogen atom as substituents, or heteroaryl groups which may have a substituent, respectively.
  • Ar 14 and Ar 15 may be the same or different from each other, and are preferably the same.
  • Ar 12 and Ar 13 independently represent any of the groups represented by the formulas (2) to (4).
  • Ar 12 and Ar 13 may be the same or different from each other, and are preferably the same.
  • * A and * B represent the bonding position.
  • * A and * B may mean that * A is the bond position on the (Ar 11 ) n11 side, or * B is the bond position on the (Ar 11 ) n11 side. May be. Above all, in the formula (3), it is preferable that * A is the coupling position on the (Ar 11 ) n11 side.
  • X 21 and X 22 independently represent a sulfur atom, an oxygen atom, or a selenium atom, and a sulfur atom or an oxygen atom is preferable.
  • R represents a hydrogen atom or a substituent.
  • the substituent that can be represented by R is preferably a halogen atom (fluorine atom or the like).
  • at least one of Y 21 and Y 22 represents a nitrogen atom.
  • only Y 21 may be a nitrogen atom
  • only Y 22 may be a nitrogen atom, or both may be nitrogen atoms.
  • X 31 represents an oxygen atom, a sulfur atom, or a selenium atom, and a sulfur atom or an oxygen atom is preferable.
  • R indicates a hydrogen atom or a substituent.
  • a nitrogen atom or ⁇ CH is preferable independently of each other.
  • the substituent that can be represented by R is preferably a halogen atom (fluorine atom or the like).
  • 0 to 4 may be nitrogen atoms, 0 or 1 is preferably a nitrogen atom, and 1 is more preferably a nitrogen atom.
  • X 41 represents an oxygen atom, a sulfur atom, or a selenium atom, and a sulfur atom or an oxygen atom is preferable.
  • R indicates a hydrogen atom or a substituent.
  • a nitrogen atom or ⁇ CH is preferable independently of each other.
  • the substituent that can be represented by R is preferably a halogen atom (fluorine atom or the like).
  • 0 to 3 may be nitrogen atoms, and 1 or 2 are preferably nitrogen atoms.
  • Ar 12 and Ar 13 independently represent any of the groups represented by the formulas (5) to (13), and the formula (5), the formula (6), and the formula (8) to the formula (8) to the formula (8) to the formula (8). It is more preferable to represent any of the groups represented by (13).
  • Ar 11 is a group represented by the formula (A5)
  • Ar 12 and Ar 13 are independently represented by the formulas (5), the formula (6), and the formulas (8) to (13). It is preferably one of the groups to be used.
  • the groups represented by the formulas (5) to (6) are suitable forms of the groups represented by the formula (2), and the groups represented by the formulas (7) to (11) are represented by the formula (3). ), And the groups represented by the formulas (12) to (13) are the preferred forms of the groups represented by the formula (4).
  • * A and * B represent the bonding position.
  • * A and * B may mean that * A is the bond position on the (Ar 11 ) n11 side, or * B is the bond position on the (Ar 11 ) n11 side. May be.
  • * A is the bonding position on the (Ar 11 ) n11 side.
  • RA represents a hydrogen atom or a substituent, and a hydrogen atom is preferable.
  • the substituent that can be represented by RA is preferably a halogen atom (fluorine atom or the like).
  • the following table shows examples of combinations of forms in which each group of Ar 14 to Ar 15 , n12, and n13 or each numerical value can be taken in each of the above structural formulas.
  • * indicates the bond position
  • Ph indicates a phenyl group.
  • the bond position (*) on the left side of the group shown in the "Ar 12 " column is the bond position on the Ar 14 side
  • the bond position (*) on the right side is the center side ((Ar 11 ) in the equation (1). )
  • the bond position (*) on the right side of the group shown in the "Ar 13 " column is the bond position on the Ar 15 side, and the bond position (*) on the left side corresponds to the center side ((Ar 11 ) n11 in the equation (1)).
  • the bond position on the side of the base is the bond position on the Ar 15 side, and the bond position (*) on the left side corresponds to the center side ((Ar 11 ) n11 in the equation (1)).
  • the molecular weight of the specific compound is not particularly limited, preferably 550 to 1200, and more preferably 600 to 900. When the molecular weight is 1200 or less, the vapor deposition temperature does not rise and the decomposition of the compound is unlikely to occur. When the molecular weight is 550 or more, the glass transition point of the vapor-film deposition film is not lowered, and the heat resistance of the photoelectric conversion element is improved.
  • the specific compound is particularly useful as a material for a photoelectric conversion film used in an image sensor, an optical sensor, or a photovoltaic cell.
  • 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 fluorescence diagnostic agent material.
  • the specific compound is preferably a compound having an ionization potential of -5.0 to -6.0 eV in a single membrane in terms of matching the energy level with the n-type semiconductor material described later.
  • the maximum absorption wavelength of the specific compound is not particularly limited, and is preferably in the wavelength range of, for example, 350 to 550 nm, and more preferably in the wavelength range of 400 to 550 nm.
  • the maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) by adjusting the absorption spectrum of the specific compound to a concentration such that the absorbance becomes 0.5 to 1.
  • solvent chloroform
  • the specific compound is not soluble in chloroform, the value measured using the specific compound in a film state after vapor deposition of the specific compound is used as the maximum absorption wavelength of the specific compound.
  • the maximum absorption wavelength of the photoelectric conversion film is not particularly limited, and is preferably in the wavelength range of, for example, 300 to 700 nm, and more preferably in the wavelength range of 400 to 700 nm.
  • the specific compound may be used alone or in combination of two or more.
  • the photoelectric conversion film contains a dye as a component other than the above-mentioned specific compound.
  • the dye is preferably an organic dye.
  • the above-mentioned pigments include, for example, cyanine pigments, styryl pigments, hemicyanine pigments, merocyanine pigments (including zero methine merocyanin (simple merocyanin)), rodacyanine pigments, allopolar pigments, oxonols pigments, hemioxonor pigments, squalium pigments, croconium pigments, and azamethines.
  • the content of the dye with respect to the total content of the specific compound and the dye in the photoelectric conversion film (film thickness in terms of single layer of dye / (film thickness in terms of single layer of specific compound + single dye)
  • the film thickness) ⁇ 100)) in terms of layers is preferably 15 to 75% by volume, more preferably 20 to 60% by volume, and even more preferably 25 to 50% by volume.
  • the dye may be used alone or in combination of two or more.
  • the photoelectric conversion film further contains an n-type semiconductor material as a component other than the above-mentioned specific compound and dye.
  • the n-type semiconductor material is an acceptor-type organic semiconductor material (compound), and refers to an organic compound having a property of easily accepting electrons. More specifically, the n-type semiconductor material is preferably an organic compound having a higher electron affinity than the specific compound when used in contact with the above-mentioned specific compound.
  • the n-type semiconductor material is preferably an organic compound having a higher electron affinity than the dye when used in contact with the above-mentioned dye.
  • the electron affinity of the n-type semiconductor material is preferably 3.0 to 5.0 eV.
  • the n-type semiconductor material is, for example, fullerene selected from the group consisting of fullerene and its derivatives, condensed aromatic carbocyclic compounds (for example, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and , Fluolanthene derivative); 5- to 7-membered heterocyclic compound having at least one nitrogen atom, oxygen atom, and sulfur atom (eg, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxalin, quinazoline, phthalazine).
  • fullerene selected from the group consisting of fullerene and its derivatives, condensed aromatic carbocyclic compounds (for example, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene
  • Examples thereof include styrylallylene derivatives; metal complexes having a nitrogen-containing heterocyclic compound as a ligand; silol compounds; and the compounds described in paragraphs [0056] to [0057] of JP-A-2006-100677.
  • the n-type semiconductor material preferably contains fullerenes selected from the group consisting of fullerenes and derivatives thereof.
  • fullerenes selected from the group consisting of fullerenes and derivatives thereof.
  • the fullerene include 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.
  • the fullerene derivative include compounds in which a substituent is added to the above fullerene.
  • the substituent is preferably an alkyl group, an aryl group, or a heterocyclic group.
  • the fullerene derivative the compound described in JP-A-2007-123707 is preferable.
  • the thickness / thickness of a specific compound in terms of a single layer + film thickness of a dye in terms of a single layer + film thickness of an n-type semiconductor material in terms of a single layer) ⁇ 100)
  • the n-type semiconductor material may be used alone or in combination of two or more.
  • the total thickness of the semiconductor materials) ⁇ 100) is preferably 50 to 100% by volume, more preferably 80 to 100% by volume.
  • the fullerenes may be used alone or in combination of two or more.
  • the molecular weight of the n-type semiconductor material is preferably 200 to 1200, more preferably 200 to 1000.
  • the photoelectric conversion film is substantially composed of only a specific compound, a dye, and an n-type semiconductor material.
  • the fact that the photoelectric conversion film is substantially composed of only the specific compound, the dye, and the n-type semiconductor material means that the total content of the specific compound, the dye, and the n-type semiconductor material is 95 with respect to the total mass of the photoelectric conversion film. It means that it is ⁇ 100% by mass.
  • the photoelectric conversion film is preferably a mixed layer formed in a state where the specific compound and the dye are mixed.
  • the photoelectric conversion film is preferably a mixed layer formed by mixing a specific compound and the n-type semiconductor material.
  • the photoelectric conversion film contains a dye and an n-type semiconductor material
  • the photoelectric conversion film is preferably a mixed layer formed by mixing a specific compound, a dye, and an n-type semiconductor material.
  • a mixed layer is a layer in which two or more kinds of materials are mixed in a single layer.
  • the photoelectric conversion film containing a specific compound is a non-luminescent film, and has characteristics different from those of an organic light emitting device (OLED: Organic Light Emitting Diode).
  • the non-luminescent film is intended to be a film having a emission quantum efficiency of 1% or less, and the emission quantum efficiency is preferably 0.5% or less, more preferably 0.1% or less.
  • the photoelectric conversion film can be formed mainly by a dry film forming method.
  • the dry film forming method includes, for example, a vapor deposition method (particularly, a vacuum vapor deposition method), a sputtering method, an ion plating method, a physical vapor deposition method such as an MBE (Molecular Beam Epitaxy) method, and a CVD method such as plasma polymerization. (Chemical Vapor Deposition) method can be mentioned. Of these, the vacuum vapor deposition method is preferable.
  • the manufacturing conditions such as the degree of vacuum and the vapor deposition temperature can be set according to a conventional method.
  • the thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, further preferably 50 to 500 nm, and particularly preferably 50 to 400 nm.
  • the electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material.
  • the conductive material include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected.
  • the material constituting the upper electrode 15 is, for example, antimony or fluorine-doped tin oxide (ATO: Antimony Tin Oxide, FTO: Fluorine topped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Conductive metal oxides such as Indium Tin Oxide) and indium tin oxide (IZO); metal thin films such as gold, silver, chromium, and nickel; these metals and conductive metal oxides. Examples thereof include mixtures or laminates; organic conductive materials such as polyaniline, polythiophene and polypyrrole; and carbon materials such as graphene and carbon nanotubes. Of these, conductive metal oxides are preferable from the viewpoint of high conductivity and transparency.
  • the sheet resistance may be, for example, 100 to 10000 ⁇ / ⁇ .
  • the degree of freedom in the range of film thickness that can be thinned is large.
  • Increasing the light transmittance is preferable because it increases the light absorption in the photoelectric conversion film and increases the photoelectric conversion ability.
  • the film 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 may reflect light without being transparent, depending on the intended use.
  • the material constituting the lower electrode 11 is, for example, antimony or fluorine-doped tin oxide (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium tin oxide (IZO).
  • Conductive metal oxides such as gold, silver, chromium, nickel, titanium, tungsten, and metals such as aluminum, oxides of these metals or conductive compounds such as nitrides (as an example, titanium nitride (TiN)). ); Mixtures or laminates of these metals and conductive metal oxides; Organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as graphene and carbon nanotubes. Be done.
  • the method for forming the electrode is not particularly limited and can be appropriately selected depending on the electrode material. Specifically, a wet method such as a printing method and a coating method; a physical method such as a vacuum vapor deposition method, a sputtering method, and an ion plating method; and a chemical method such as CVD and plasma CVD method. , Etc. can be mentioned.
  • a wet method such as a printing method and a coating method
  • a physical method such as a vacuum vapor deposition method, a sputtering method, and an ion plating method
  • a chemical method such as CVD and plasma CVD method.
  • Etc. can be mentioned.
  • 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 (sol-gel method, etc.), and application of a dispersion of indium tin oxide can be mentioned.
  • the photoelectric conversion element of the present invention 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.
  • the charge blocking film include an electron blocking film and a hole blocking film.
  • the electron blocking film is a donor organic semiconductor material (compound), and for example, the following p-type organic semiconductor can be used.
  • One type of p-type organic semiconductor may be used alone, or two or more types may be used.
  • the p-type organic semiconductor is, for example, a triarylamine compound (for example, N, N'-bis (3-methylphenyl)-(1,1'-biphenyl) -4,4'-diamine (TPD), 4,4.
  • TPD triarylamine
  • '-Bis [N- (naphthyl) -N-phenyl-amino] biphenyl ( ⁇ -NPD) the compound described in paragraphs [0128] to [0148] of JP2011-228614A, JP-A-2011-176259.
  • cyanine compounds oxonol compounds, polyamine compounds, indol compounds, pyrrol compounds, pyrazole compounds, polyarylene compounds, condensed aromatic carbocyclic compounds (for example, Naphthalene derivative, anthracene derivative, phenanthrene derivative, tetracene derivative, pentacene derivative, pyrene derivative, perylene derivative, and fluorantene derivative), porphyrin compound, phthalocyanine compound, triazole compound, oxadiazole compound, imidazole compound, polyarylalkane compound, pyrazolone Examples thereof include compounds, amino-substituted calcon compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having a nitrogen-containing heterocyclic compound as a ligand.
  • the p-type organic semiconductor include compounds having a smaller ionization potential than the
  • a polymer material can also be used as the electron blocking film.
  • the polymer material include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrrole, 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 made of an inorganic material.
  • Inorganic materials that can be electron blocking films include, for example, calcium oxide, chromium oxide, copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium oxide copper, niobium oxide, molybdenum oxide, and indium copper oxide. , Indium silver oxide, and iridium oxide.
  • the hole blocking film is an acceptor-type organic semiconductor material (compound), and the above-mentioned n-type semiconductor material or the like can be used.
  • the method for producing the charge blocking film is not particularly limited, and examples thereof include a dry film forming method and a wet film forming method.
  • the dry film forming method include 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, and a physical vapor deposition method such as a vacuum vapor deposition method is preferable.
  • the wet film forming method include an inkjet method, a spray method, a nozzle printing method, a spin coating method, a dip coating method, a casting method, a die coating method, a roll coating method, a bar coating method, and a gravure coating method. From the viewpoint of precision patterning, the inkjet method is preferable.
  • the thickness of the charge blocking film is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm, respectively.
  • the photoelectric conversion element may further have a substrate.
  • the type of substrate used is not particularly limited, and examples thereof include a semiconductor substrate, a glass substrate, and a plastic substrate.
  • the position of the substrate is not particularly limited, and usually, a conductive film, a photoelectric conversion film, and a transparent conductive film are laminated on the substrate in this order.
  • the photoelectric conversion element may further have a sealing layer.
  • the performance of the photoelectric conversion material may be significantly deteriorated due to the presence of deterioration factors such as water molecules. Therefore, the entire photoelectric conversion film is provided with a dense metal oxide, metal nitride, ceramics such as metal nitride oxide, or a sealing layer such as diamond-like carbon (DLC: Diamond-like Carbon) that does not allow water molecules to permeate.
  • DLC Diamond-like Carbon
  • the photoelectric conversion element is an element that converts the optical information of an image into an electric signal. Normally, a plurality of photoelectric conversion elements are arranged in a matrix on the same plane, and each photoelectric conversion element (pixel) has an optical signal. 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, each pixel is composed of one or more photoelectric conversion elements and one or more transistors.
  • the image pickup element is mounted on a digital camera, an image pickup element such as a digital video camera, an electronic endoscope, and an image pickup module such as a mobile phone.
  • the photoelectric conversion element of the present invention is also preferably used for an optical sensor having the photoelectric conversion element of the present invention.
  • the optical sensor may be used by the photoelectric conversion element alone, or may be used as a line sensor in which the photoelectric conversion elements are arranged in a straight line, or a two-dimensional sensor in which the photoelectric conversion elements are arranged in a plane.
  • the present invention also relates to compounds.
  • the compound of the present invention is the same as the above-mentioned specific compound (compound represented by the formula (1)), and the preferred conditions are also the same.
  • LDI-MS soft laser desorption / ionization mass spectrometry
  • N-type semiconductor material Fullerene C60 was used as an n-type semiconductor material used for evaluation in the production of a photoelectric conversion element described later.
  • the photoelectric conversion element includes a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15.
  • amorphous ITO is formed on a glass substrate by a sputtering method to form a lower electrode 11 (thickness: 30 nm), and the following compound (C-1) is further vacuumed on the lower electrode 11.
  • a film was formed by a heat vapor deposition method to form an electron blocking film 16A (thickness: 30 nm).
  • the evaluation compound shown in Table 1 the n-type semiconductor material, and the dye were co-deposited on the electron blocking film 16A to form a photoelectric conversion film 12 as a mixed layer.
  • the ratio of the vapor deposition rates of the evaluation compound, the n-type semiconductor material, and the dye the film thickness of these components in the photoelectric conversion film in terms of a single layer is the ratio shown in the "component ratio" column of Table 1. Adjusted to. Further, the following compound (C-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm).
  • Amorphous ITO was formed on the hole blocking film 16B by a sputtering method to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm).
  • an aluminum oxide (Al 2 O 3 ) layer is formed on the SiO film by an ALCVD (Atomic Layer Chemical Vapor Deposition) method.
  • ALCVD Atomic Layer Chemical Vapor Deposition
  • the dark current of each of the obtained photoelectric conversion elements was measured by the following method. A voltage was applied to the lower electrode and the upper electrode of each photoelectric conversion element so as to have an electric field strength of 2.5 ⁇ 105 V / cm, and the current value (dark current) in a dark place was measured. As a result, it was confirmed that the dark current was 50 nA / cm 2 or less in any of the photoelectric conversion elements, and the dark current was sufficiently low.
  • Relative ratio (Integral value of photoelectric conversion efficiency in light having a wavelength of 400 to 550 nm of the photoelectric conversion element to be evaluated) / (Integral value of photoelectric conversion efficiency in light having a wavelength of 400 to 550 nm of the photoelectric conversion element of Example 1-1)
  • C Relative ratio of integrated values of photoelectric conversion efficiency is 1. .0 or more and less than 1.2
  • Relative ratio of integrated values of photoelectric conversion efficiency is less than 0.8
  • the photoelectric conversion efficiency ratio was calculated from the following formula using the integrated value of the photoelectric conversion efficiency in light with a wavelength of 400 to 550 nm measured at each electric field strength, and the electric field strength dependence of the photoelectric conversion efficiency was evaluated by the following criteria. .. The closer the photoelectric conversion efficiency ratio is to 1, the smaller the electric field strength dependence of the photoelectric conversion efficiency is, which is preferable.
  • Photoelectric conversion efficiency ratio (Integration of photoelectric conversion efficiency in light with a wavelength of 400 to 550 nm under the condition that a voltage is applied to the photoelectric conversion element to be evaluated so as to have an electric field strength of 1.5 ⁇ 105 V / cm.
  • Photoelectric conversion efficiency ratio is 0.9 or more and 1.0 or less
  • Photoelectric conversion efficiency ratio is 0.8 or more and less than 0.9
  • Photoelectric conversion efficiency ratio is 0.7 or more and less than 0.8
  • Photoelectric conversion efficiency Ratio less than 0.7

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