WO2019176754A1 - 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 PDFInfo
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- WO2019176754A1 WO2019176754A1 PCT/JP2019/009234 JP2019009234W WO2019176754A1 WO 2019176754 A1 WO2019176754 A1 WO 2019176754A1 JP 2019009234 W JP2019009234 W JP 2019009234W WO 2019176754 A1 WO2019176754 A1 WO 2019176754A1
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- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical class O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
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- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- 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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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K30/81—Electrodes
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- H10K39/32—Organic image sensors
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- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a photoelectric conversion element, an imaging element, an optical sensor, and a compound.
- Patent Document 1 discloses a photoelectric conversion element having a photoelectric conversion film containing a predetermined compound.
- One aspect of the imaging element is a stacked imaging element in which a plurality of photoelectric conversion elements having different types of light to be received are stacked.
- a part of the incident light is absorbed by the photoelectric conversion element arranged on the incident side, and the transmitted light is absorbed by the photoelectric conversion element arranged further back.
- the half width of the absorption peak of each photoelectric conversion element is narrower because color separation is easier.
- 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 photoelectric conversion device according to any one of (1) to (4), wherein R a1 and R a2 each independently represent a substituent having 3 or more carbon atoms.
- R a1 and R a2 each independently represent a secondary alkyl group having 3 or more carbon atoms, an aryl group having 3 or more carbon atoms, or a heteroaryl group having 3 or more carbon atoms, 5)
- the photoelectric conversion element in any one of.
- the photoelectric conversion film further includes an n-type organic semiconductor,
- An imaging device comprising the photoelectric conversion device according to any one of (1) to (8).
- a photoelectric conversion element and another photoelectric conversion element are laminated, The imaging device according to (10), wherein at least a part of the incident light is transmitted through the photoelectric conversion element and then received by another photoelectric conversion element.
- the photoelectric conversion element is a green photoelectric conversion element, The image sensor according to (10) or (11), wherein the other photoelectric conversion elements include a blue photoelectric conversion element and a red photoelectric conversion element.
- An optical sensor comprising the photoelectric conversion element according to any one of (1) to (8).
- R a1 and R a2 each independently represent a secondary alkyl group having 3 or more carbon atoms, an aryl group having 3 or more carbon atoms, or a heteroaryl group having 3 or more carbon atoms, The compound according to any one of 18).
- the photoelectric conversion element which has a photoelectric conversion film with a narrow half width of an absorption peak can be provided.
- an image pick-up element, an optical sensor, and a compound can be provided.
- 1 is a 1 H NMR (Nuclear Magnetic Resonance) spectrum of the compound (D-1).
- 1 is a 1 H NMR spectrum of a compound (D-2).
- 1 is a 1 H NMR spectrum of compound (D-6).
- 1 is a 1 H NMR spectrum of a compound (D-7).
- 1 is a 1 H NMR spectrum of a compound (D-8).
- 1 is a 1 H NMR spectrum of a compound (D-9).
- 1 is a 1 H NMR spectrum of a compound (D-10).
- 1 is a 1 H NMR spectrum of a compound (D-11).
- a substituent or the like that does not specify substitution or non-substitution is further substituted with a substituent (for example, substituent W described later) within a range not impairing the intended effect.
- a substituent for example, substituent W described later
- the expression “alkyl group” means an alkyl group that may be substituted with a substituent (for example, substituent W described later).
- a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
- a bulky substituent is introduced into a compound represented by the formula (1) described later (hereinafter also referred to as “specific compound”) contained in the photoelectric conversion film.
- specific compound a compound represented by the formula (1) described later
- FIG. 1 the cross-sectional schematic diagram of one Embodiment of the photoelectric conversion element of this invention is shown.
- a photoelectric conversion element 10a illustrated 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 that includes a specific compound described later, and an upper electrode.
- 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 stacked on the lower electrode 11 in this order. Note that 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 use and characteristics.
- the photoelectric conversion element 10 a it is preferable that light is incident on the photoelectric conversion film 12 through the upper electrode 15. 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 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, and 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 when it is incorporated in an image sensor, a voltage can be applied by the same method. As will be described in detail later, the photoelectric conversion element 10a (or 10b) can be suitably applied to an imaging element.
- the photoelectric conversion film is a film containing a specific compound as a photoelectric conversion material. By using this compound, a photoelectric conversion element having a photoelectric conversion film having a narrow half width of the absorption peak can be obtained.
- the specific compound will be described in detail.
- the formula (1) regarding the geometric isomer that can be distinguished based on the C ⁇ C double bond composed of the carbon atom to which R 1 is bonded and the carbon atom adjacent thereto, the formula (1) Is also included. That is, both the cis isomer and the trans isomer distinguished based on the C ⁇ C double bond are included in the formula (1).
- Ar 1 represents an aryl group that may have a substituent or a heteroaryl group that may have a substituent.
- the number of carbon atoms in the aryl group is not particularly limited, but is preferably 6 to 30, more preferably 6 to 18, and still more preferably 6.
- the aryl group may be a monocyclic structure or a condensed ring structure in which two or more rings are condensed (fused ring structure).
- a phenyl group, a naphthyl group, or an anthryl group is preferable, and a phenyl group is more preferable.
- Examples of the substituent that the aryl group may have include a substituent W described later, and examples thereof include an alkyl group.
- the aryl group may have a plurality of substituents.
- the number of substituents that the aryl group has is not particularly limited, but the point becomes narrower than the half width of the absorption peak of the photoelectric conversion film (hereinafter simply referred to as “the effect of the present invention is more excellent”). 1) to 5 is preferable, and 2 to 3 is more preferable.
- the number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably 3 to 30, and more preferably 3 to 18.
- Heteroaryl groups have heteroatoms in addition to carbon and hydrogen atoms. Examples of the hetero atom include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferable.
- the number of heteroatoms contained in the heteroaryl group is not particularly limited, but is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.
- the number of ring members of the heteroaryl group is not particularly limited, but is preferably 3 to 8, more preferably 5 to 7, and still more preferably 5 to 6.
- the heteroaryl group may be a monocyclic structure or a condensed ring structure in which two or more rings are condensed. In the case of a condensed ring structure, an aromatic hydrocarbon ring having no hetero atom (for example, a benzene ring) may be included.
- heteroaryl groups include furyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pteridinyl, pyrazinyl, quinoxalinyl, pyrimidinyl, quinazolyl, pyridazinyl, cinnolinyl, Phthalazinyl group, triazinyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, indazolyl group, isoxazolyl group, benzoisoxazolyl group, isothiazolyl group, benzoisothiazolyl Group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, benzofuryl group, thienyl group, be
- Examples of the substituent that the heteroaryl group may have include the same substituents that the above-described aryl group may have.
- the number of substituents that the heteroaryl group has is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 3.
- R 1 represents a hydrogen atom or a substituent. Among these, R 1 is preferably a hydrogen atom in that the effect of the present invention is more excellent.
- the definition of the said substituent is synonymous with the substituent W mentioned later.
- Examples of the substituent include an alkyl group, an aryl group, and a heteroaryl group.
- X 1 to X 3 each independently represent CR 2 ( ⁇ CR 2 —) or a nitrogen atom ( ⁇ N—).
- R 2 represents a hydrogen atom or a substituent.
- the definition of a substituent is synonymous with the substituent W mentioned later.
- examples of the substituent include an alkyl group, an aryl group, and a heteroaryl group.
- R a1 and R a2 each independently represent a substituent having 2 or more carbon atoms.
- the number of carbon atoms contained in the substituent having 2 or more carbon atoms is preferably 3 or more in that the effect of the present invention is more excellent. That is, the substituent having 2 or more carbon atoms is preferably a substituent having 3 or more carbon atoms.
- the upper limit of the carbon number is not particularly limited, but 10 or less can be mentioned.
- Examples of the substituent having 2 or more carbon atoms include an aliphatic hydrocarbon group having 2 or more carbon atoms, which may contain a hetero atom, and an aromatic group having 2 or more carbon atoms.
- aliphatic hydrocarbon group examples include an alkyl group, an alkenyl group, and an alkynyl group. These groups may contain heteroatoms such as an oxygen atom, a nitrogen atom, and a sulfur atom.
- Aromatic groups include aryl groups and heteroaryl groups.
- the secondary alkyl group having 3 or more carbon atoms As the substituent having 2 or more carbon atoms, the secondary alkyl group having 3 or more carbon atoms, the aryl group having 3 or more carbon atoms, or the heteroaryl having 3 or more carbon atoms is preferable in that the effect of the present invention is more excellent. Groups are preferred.
- the secondary alkyl group means an alkyl group having a secondary carbon atom. Examples of the secondary alkyl group having 3 or more carbon atoms include isopropyl group, isobutyl group, pentan-2-yl group, pentan-3-yl group, and 3-methyl-2-pentyl group.
- Examples of the aryl group having 3 or more carbon atoms include the groups exemplified for the aryl group represented by Ar 1 .
- Examples of the heteroaryl group having 3 or more carbon atoms include the groups exemplified for the heteroaryl group represented by Ar 1 .
- L 1 represents a carbon atom, a silicon atom, or a germanium atom. Especially, a carbon atom is preferable at the point which the effect of this invention is more excellent.
- B 1 represents an aromatic ring which may have a substituent.
- the aromatic ring may be monocyclic or polycyclic.
- Aromatic rings include aromatic hydrocarbon rings and aromatic heterocycles. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring.
- Examples of the aromatic heterocycle include a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, and an oxazole ring. Among these, an aromatic hydrocarbon ring is preferable and a benzene ring is more preferable in that the effect of the present invention is more excellent.
- the definition of a substituent is synonymous with the substituent W mentioned later. Examples of the substituent include an alkyl group, an aryl group, and a heteroaryl group. These groups may further have a substituent.
- Y represents a group represented by the formula (1-1) or a group represented by the formula (1-2).
- a group represented by the formula (1-1) is preferable in that the effect of the present invention is more excellent.
- * In the formula (1-1) and the formula (1-2) represents a bonding position.
- a 1 represents a ring containing at least two carbon atoms. The two carbon atoms are the carbon atom in the carbonyl group specified in formula (1-1) and the carbon specified in formula (1-1) adjacent to the carbon atom of the carbonyl group. intended and atoms, any carbon atom is an atom that constitutes the a 1.
- the carbon atom constituting the ring may be substituted with another carbonyl carbon (> C ⁇ O) or thiocarbonyl carbon (> C ⁇ S).
- other carbonyl carbon (> C ⁇ O) is intended to mean a carbonyl carbon having a carbon atom constituting the ring other than the carbonyl carbon specified in formula (1-1). .
- the number of carbon atoms of A 1 is preferably 3 to 30, more preferably 3 to 20, and still more preferably 3 to 15.
- the said carbon number is a number containing two carbon atoms specified in a formula.
- a 1 may have a hetero atom, and examples thereof include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a nitrogen atom, a sulfur atom Or an oxygen atom is preferable and an oxygen atom is more preferable.
- the number of heteroatoms in A 1 is preferably 0 to 10, more preferably 0 to 5, and still more preferably 0 to 2.
- the number of heteroatoms is introduced into the ring by replacing the carbon atom constituting the ring represented by A 1 with a carbonyl carbon (> C ⁇ O) or a thiocarbonyl carbon (> C ⁇ S).
- the number of heteroatoms (which are intended to include the carbonyl carbon specified in formula (1-1)) and the number of heteroatoms that the substituent of A 1 has.
- a 1 may have a substituent, and the substituent may be a halogen atom (preferably a chlorine atom), an alkyl group (straight, branched, or cyclic).
- the silicon number is preferably 1 to 4, and more preferably 1).
- a 1 may or may not show aromaticity.
- a 1 may be a monocyclic structure or a condensed ring structure, but is preferably a 5-membered ring, a 6-membered ring, or a condensed ring containing at least one of a 5-membered ring and a 6-membered ring.
- the number of rings forming the condensed ring is preferably 1 to 4, and more preferably 1 to 3.
- (B) 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-one and the like.
- (D) Oxindole nucleus For example, 1-alkyl-2,3-dihydro-2-oxindole and the like.
- (E) 2,4,6-trioxohexahydropyrimidine nucleus for example, barbituric acid or 2-thiobarbituric acid, and derivatives thereof.
- the 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, 1, 1,3-diaryl compounds such as 3-diphenyl, 1,3-di (p-chlorophenyl) and 1,3-di (p-ethoxycarbonylphenyl), 1-alkyl such as 1-ethyl-3-phenyl Examples include 1-aryl isomers and 1,3-diheteroaryl isomers such as 1,3-di (2-pyridyl).
- (F) 2-thio-2,4-thiazolidinedione nucleus for example, rhodanine and derivatives thereof.
- the derivatives include 3-methylrhodanine, 3-ethylrhodanine, 3-alkylrhodanine such as 3-allylrhodanine, 3-arylrhodanine such as 3-phenylrhodanine, and 3- And 3-heteroaryl rhodanine such as (2-pyridyl) rhodanine.
- (J) 2,4-thiazolidinedione nucleus: for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, 3-phenyl-2,4-thiazolidinedione, and the like.
- (K) Thiazolin-4-one nucleus for example, 4-thiazolinone and 2-ethyl-4-thiazolinone.
- (M) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4- Imidazolidinedione and the like.
- (N) Imidazolin-5-one nucleus for example, 2-propylmercapto-2-imidazolin-5-one and the like.
- (O) 3,5-pyrazolidinedione nucleus for example, 1,2-diphenyl-3,5-pyrazolidinedione, 1,2-dimethyl-3,5-pyrazolidinedione, and the like.
- (P) Benzothiophene-3 (2H) -one nucleus for example, benzothiophene-3 (2H) -one, oxobenzothiophene-3 (2H) -one, and dioxobenzothiophene-3 (2H) -one etc.
- (R) Benzofuran-3- (2H) -one nucleus for example, benzofuran-3- (2H) -one and the like.
- R b1 and R b2 each independently represent a cyano group or —COOR d1 .
- R d1 represents an alkyl group or an aryl group.
- R a1 and R a2 may be bonded to each other to form a ring. More specifically, R a1 and R a2 may be bonded to each other via a single bond or a linking group to form a ring.
- the linking group include —O—, —S—, an alkylene group, a silylene group, an alkenylene group, a cycloalkylene group, a cycloalkenylene group, an arylene group, a divalent heterocyclic group, and an imino group.
- Examples of the ring formed by combining R a1 and R a2 with each other include an aromatic ring (aromatic hydrocarbon ring or aromatic heterocycle) and a non-aromatic ring.
- Examples of the aromatic ring include a benzene ring and a fluorene ring.
- the specific compound is preferably a compound represented by the following formula (1-3).
- R a3 and R a4 each independently represent a divalent substituent having 2 or more carbon atoms.
- the number of carbon atoms contained in the divalent substituent having 2 or more carbon atoms is preferably 3 or more in that the effect of the present invention is more excellent. That is, the divalent substituent having 2 or more carbon atoms is preferably a divalent substituent having 3 or more carbon atoms.
- the upper limit of the carbon number is not particularly limited, but 10 or less can be mentioned.
- Examples of the divalent substituent having 2 or more carbon atoms include, for example, a divalent aliphatic hydrocarbon group having 2 or more carbon atoms which may contain a hetero atom, and a divalent aromatic having 2 or more carbon atoms.
- Examples of the aliphatic hydrocarbon group include an alkylene group, an alkenylene group, and an alkynylene group. These groups may contain heteroatoms such as an oxygen atom, a nitrogen atom, and a sulfur atom.
- Examples of the aromatic group include an arylene group and a heteroarylene group. Among these, an arylene group having 3 or more carbon atoms (for example, a phenylene group) or a heteroarylene group having 3 or more carbon atoms is preferable in that the effect of the present invention is more excellent.
- L 2 represents a single bond or a linking group (a divalent linking group).
- the linking group include —O—, —S—, an alkylene group, a silylene group, an alkenylene group, a cycloalkylene group, a cycloalkenylene group, an arylene group, a divalent heterocyclic group, and an imino group.
- the specific compound does not have any of a carboxy group, a salt of a carboxy group, a phosphoric acid group, a salt of a phosphoric acid group, a sulfonic acid group, and a salt of a sulfonic acid group from the viewpoint of avoiding deterioration in deposition suitability. More specifically, the substituent in the specific compound does not include any of a carboxy group, a carboxy group salt, a phosphoric acid group, a phosphoric acid group salt, a sulfonic acid group, and a sulfonic acid group salt.
- the specific compound is preferably a compound represented by the formula (2), more preferably a compound represented by the formula (3), in terms of more excellent effects of the present invention. More preferably, it is a compound represented.
- R 3 to R 5 each independently represents a hydrogen atom or a substituent.
- the definition of a substituent is synonymous with the substituent W mentioned later.
- the compound represented by the formula (2) does not have any of a carboxy group, a carboxy group salt, a phosphoric acid group, a phosphoric acid group salt, a sulfonic acid group, and a sulfonic acid group salt.
- the compound represented by the formula (2) is preferably a compound represented by the formula (2-1).
- R 6 to R 13 each independently represents a hydrogen atom or a substituent.
- the definition of a substituent is synonymous with the substituent W mentioned later.
- R 10 and R 11 , R 11 and R 12 , R 12 and R 13 may be independently bonded to each other to form a ring.
- the kind of ring formed includes an aromatic ring (aromatic hydrocarbon ring or aromatic heterocycle) and a non-aromatic ring. Examples of the aromatic ring include a benzene ring and a fluorene ring.
- the compound represented by the formula (3) does not have any of a carboxy group, a carboxy group salt, a phosphoric acid group, a phosphoric acid group salt, a sulfonic acid group, and a sulfonic acid group salt.
- the compound represented by the formula (3) is preferably a compound represented by the formula (3-1).
- the definitions of Ar 1 , R 1 , and R 3 to R 13 are as described above.
- the definitions of R a3 , R a4 and L 2 are the same as the definitions of each group in formula (1-3).
- the compound represented by the formula (3-1) does not have any of a carboxy group, a carboxy group salt, a phosphoric acid group, a phosphoric acid group salt, a sulfonic acid group, and a sulfonic acid group salt. .
- R 1 , R 3 to R 13 , R a1 , and R a2 are as described above.
- R 14 to R 16 each independently represents a hydrogen atom or a substituent.
- the definition of a substituent is synonymous with the substituent W mentioned later.
- R c1 and R c2 each independently represent a hydrogen atom or a substituent, and at least one of R c1 and R c2 represents a substituent.
- the definition of a substituent is synonymous with the substituent W mentioned later. Examples of the substituent include an alkyl group, an aryl group, and a heteroaryl group.
- the compound represented by Formula (4) does not have any of a carboxy group, a salt of a carboxy group, a phosphoric acid group, a salt of a phosphoric acid group, a sulfonic acid group, and a salt of a sulfonic acid group.
- the compound represented by the formula (4) is preferably a compound represented by the formula (4-1).
- the definitions of Ar 1 , R 1 and R 3 to R 16 are as described above.
- the definitions of R a3 , R a4 and L 2 are the same as the definitions of each group in formula (1-3).
- the compound represented by the formula (4-1) does not have any of carboxy group, carboxy group salt, phosphoric acid group, phosphoric acid group salt, sulfonic acid group, and sulfonic acid group salt. .
- Substituent W It describes about the substituent W in this specification.
- substituent W include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group.
- cycloalkenyl groups and bicycloalkenyl groups alkynyl groups, aryl groups, heterocyclic groups (also referred to as heterocyclic groups, including heteroaryl groups), cyano groups, hydroxy groups, nitro groups, alkoxy groups Group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group (including anilino group), ammonio group, acylamino group, aminocarbonylamino Group, alkoxycarbonylamino group, ant Ruoxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl
- the specific compound is particularly useful as a material for a photoelectric conversion film used in an image sensor, a photosensor, or a photovoltaic cell. Usually, the specific compound often functions as a p-type organic semiconductor 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 material.
- the specific compound is a compound having an ionization potential of ⁇ 5.0 to ⁇ 6.0 eV in a single film from the viewpoint of matching the stability when used as a p-type organic semiconductor and the energy level of the n-type organic semiconductor. Is preferred.
- the maximum absorption wavelength of the specific compound is not particularly limited, but is 510 to 500 in that the photoelectric conversion film in the photoelectric conversion element of the present invention is suitably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion. It is preferably in the range of 570 nm, and more preferably in the range of 520 to 560 nm.
- the absorption half width of the specific compound is not particularly limited, but is 95 nm or less in that the photoelectric conversion film in the photoelectric conversion element of the present invention is suitably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion.
- the lower limit is not particularly limited, but is often 60 nm or more.
- the maximum absorption wavelength and the absorption half width are values measured in the state of a film of a specific compound (for example, a vapor deposition film of the specific compound).
- the maximum absorption wavelength of the photoelectric conversion film is not particularly limited.
- the photoelectric conversion film in the photoelectric conversion element of the present invention is suitably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion. It is preferably in the range of 570 nm, and more preferably in the range of 520 to 560 nm.
- the photoelectric conversion film preferably contains an n-type organic semiconductor as a component other than the specific compound described above.
- 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. More specifically, an n-type organic semiconductor refers to an organic compound having a higher electron affinity when two organic compounds are used in contact with each other.
- n-type organic semiconductor examples include condensed aromatic carbocyclic compounds (for example, fullerene, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); nitrogen atoms, oxygen atoms, And a 5- to 7-membered heterocyclic compound having at least one sulfur atom (for example, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, Phenanthroline, tetrazole, pyrazole, imidazole, thiazole, etc.); polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; and nitrogen-
- dye as an n-type organic semiconductor.
- the molecular weight of the n-type organic semiconductor is preferably 200 to 1200, more preferably 200 to 900.
- the n-type organic semiconductor is colorless or absorbs close to a specific compound in that the photoelectric conversion film in the photoelectric conversion element of the present invention is suitably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion. It is desirable to have a maximum wavelength and / or an absorption waveform. As a specific numerical value, it is preferable that the absorption maximum wavelength of the n-type organic semiconductor is 400 nm or less or in the range of 500 to 600 nm.
- the photoelectric conversion film preferably has a bulk heterostructure formed in a state where the specific compound and the n-type organic semiconductor are mixed.
- 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.
- the 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 film thickness of the n-type organic semiconductor in terms of a single layer) ⁇ 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume.
- a photoelectric converting film is substantially comprised from a specific compound and an n-type organic semiconductor.
- substantially means that the total content of the specific compound and the n-type organic semiconductor is 95% by mass or more with respect to the total mass of the photoelectric conversion film.
- the photoelectric conversion film containing the specific compound is a non-light-emitting film, and has a characteristic different from that of an organic electroluminescent element (OLED: Organic Light Emitting Diode).
- OLED Organic Light Emitting Diode
- the non-light-emitting film is intended for a film having an 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 include 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 plasma polymerization.
- the CVD (Chemical Vapor Deposition) method is mentioned. Of these, vacuum deposition is preferred.
- manufacturing conditions such as a degree of vacuum and a 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, still more preferably 50 to 500 nm, and particularly preferably 50 to 300 nm.
- the electrodes 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, the upper electrode 15 is preferably transparent to the light to be detected.
- Examples of the material constituting the upper electrode 15 include tin oxide doped with antimony or fluorine (ATO: Antimony Tin Oxide, FTO: Fluorine doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO) : Conductive metal oxides such as Indium Tin Oxide (IZO); Metal thin films such as gold, silver, chromium, and nickel; These metals and conductive metal oxides And organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and the like. Among these, conductive metal oxides are preferable from the viewpoints of high conductivity and transparency.
- the sheet resistance is preferably 100 to 10,000 ⁇ / ⁇ .
- the degree of freedom in the range of film thickness that can be made thin is great.
- the thickness of the upper electrode (transparent conductive film) 15 decreases, the amount of light absorbed decreases, and the light transmittance generally increases.
- An increase in light transmittance is preferable because it increases light absorption in the photoelectric conversion film and increases the photoelectric conversion ability.
- the thickness of the upper electrode 15 is preferably 5 to 100 nm, more preferably 5 to 20 nm.
- the lower electrode 11 may have transparency, or conversely, may have no transparency and reflect light.
- the material constituting the lower electrode 11 include tin oxide doped with antimony or fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
- Conductive metal oxides such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (for example, titanium nitride (TiN)) And mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole.
- 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 deposition method, a sputtering method, and an ion plating method; and a chemical method such as a CVD method and a plasma CVD method. , Etc.
- a wet method such as a printing method and a coating method
- a physical method such as a vacuum deposition method, a sputtering method, and an ion plating method
- a chemical method such as a CVD method and a plasma CVD method.
- Etc When the material of the electrode 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 a coating of a dispersion of indium tin oxide can be given.
- the photoelectric conversion element of the present invention preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
- An example of the intermediate layer is a charge blocking film.
- the charge blocking film include an electron blocking film and a hole blocking film. Below, each film
- the electron blocking film contains an electron donating compound.
- the low molecular weight material include N, N′-bis (3-methylphenyl)-(1,1′-biphenyl) -4,4′-diamine (TPD) and 4,4 Aromatic diamine compounds such as' -bis [N- (naphthyl) -N-phenyl-amino] biphenyl ( ⁇ -NPD); porphyrin compounds such as porphyrin, tetraphenylporphyrin copper, phthalocyanine, copper phthalocyanine, and titanium phthalocyanine oxide Oxazole, oxadiazole, triazole, imidazole, imidazolone, stilbene derivative, pyrazoline derivative, tetrahydroimidazole, polyarylalkane, butadiene, 4,4 ′, 4 ′′ -tris (N- (3-methylphenyl) N -Phenylamino)
- polymer material examples include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, and derivatives thereof.
- 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 made of an inorganic material.
- an inorganic material has a dielectric constant larger than that of an organic material, when the inorganic material is used for an electron blocking film, a large voltage is applied to the photoelectric conversion film, and the photoelectric conversion efficiency is increased.
- inorganic materials that can serve as an electron blocking film include calcium oxide, chromium oxide, chromium oxide copper, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, and indium oxide. Examples include copper, silver indium oxide, and iridium oxide.
- the hole blocking film contains an electron accepting compound.
- electron-accepting compounds include oxadiazole derivatives such as 1,3-bis (4-tert-butylphenyl-1,3,4-oxadiazolyl) phenylene (OXD-7); anthraquinodimethane derivatives; diphenyl Quinone derivatives; bathocuproine, bathophenanthroline, and derivatives thereof; triazole compounds; tris (8-hydroxyquinolinato) aluminum complexes; bis (4-methyl-8-quinolinato) aluminum complexes; distyrylarylene derivatives; and silole compounds Is mentioned. Further, compounds described in paragraphs [0056] to [0057] of JP-A 2006-1000076 are listed.
- 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.
- Examples of 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: Physical Vapor Deposition) method or a chemical vapor deposition (CVD) method, and a physical vapor deposition method such as a vacuum vapor deposition method is preferred.
- Examples of 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 high-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 still more preferably 5 to 30 nm.
- the photoelectric conversion element may further have a substrate.
- substrate used is not restrict
- the position of the substrate is not particularly limited, but 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 a photoelectric conversion material may be significantly degraded due to the presence of degradation factors such as water molecules. Therefore, the entire photoelectric conversion film is formed by a ceramic such as dense metal oxide, metal nitride, or metal nitride oxide that does not allow water molecules to permeate, or a sealing layer such as diamond-like carbon (DLC).
- DLC diamond-like carbon
- the above deterioration can be prevented by covering and sealing.
- the material for the sealing layer may be selected and manufactured according to paragraphs [0210] to [0215] of JP2011-082508A.
- FIG. 3 is a schematic cross-sectional view showing a schematic configuration of an image sensor for explaining an embodiment of the present invention.
- This image pickup device is mounted on an image pickup device such as a digital camera and a digital video camera, an electronic endoscope, and an image pickup module such as a mobile phone.
- 3 includes a photoelectric conversion element 10a of the present invention, a blue photoelectric conversion element 22, and a red photoelectric conversion element 24, which are stacked along the direction in which light is incident.
- the photoelectric conversion element 10a can mainly function as a green photoelectric conversion element that can receive green light.
- the image sensor 20a is a so-called laminate type color separation image sensor.
- the photoelectric conversion element 10a, the blue photoelectric conversion element 22, and the red photoelectric conversion element 24 have different detected wavelength spectra. That is, the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 correspond to photoelectric conversion elements that receive light having a wavelength different from the light received (absorbed) by the photoelectric conversion element 10a.
- the photoelectric conversion element 10a can receive green light
- the blue photoelectric conversion element 22 can receive blue light
- the red photoelectric conversion element can receive red light.
- Green light means light in the wavelength range of 500 to 600 nm
- blue light means light in the wavelength range of 400 to 500 nm
- red light means light in the wavelength range of 600 to 700 nm.
- one pixel can be formed by three light receiving portions of green, blue, and red, and the area of the light receiving portion can be increased.
- the photoelectric conversion element 10a of the present invention since the half width of the absorption peak is narrow, absorption of blue light and red light does not substantially occur, and the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 It is difficult to affect the detectability.
- the photoelectric conversion element which has a conductive film, a blue photoelectric conversion film, and a transparent conductive film in this order is mentioned.
- the type of the blue photoelectric conversion film is not particularly limited as long as it is a photoelectric conversion film that can receive blue light, and examples thereof include an organic blue photoelectric conversion film or an inorganic blue photoelectric conversion film, and an organic blue photoelectric conversion film. (A blue photoelectric conversion film composed of an organic compound) is preferable.
- the maximum absorption wavelength of the blue photoelectric conversion film is not particularly limited, but is preferably in the range of 400 to 500 nm, and more preferably in the range of 420 to 480 nm.
- a conductive film and a transparent conductive film included in the photoelectric conversion element of the present invention can be used.
- the configuration of the red photoelectric conversion element 24 is not particularly limited, and examples thereof include a photoelectric conversion element having a conductive film, a red photoelectric conversion film, and a transparent conductive film in this order.
- the type of the red photoelectric conversion film is not particularly limited as long as it is a photoelectric conversion film that can receive red light, and examples include an organic red photoelectric conversion film or an inorganic red photoelectric conversion film, and an organic red photoelectric conversion film. (Red photoelectric conversion film composed of an organic compound) is preferable.
- the maximum absorption wavelength of the red photoelectric conversion film is not particularly limited, but is preferably in the range of 600 to 700 nm, and more preferably in the range of 620 to 680 nm.
- As the conductive film and the transparent conductive film a conductive film and a transparent conductive film included in the photoelectric conversion element of the present invention can be used.
- the photoelectric conversion element of the present invention, the blue photoelectric conversion element, and the red photoelectric conversion element are arranged in this order from the light incident side.
- the arrangement is not limited to this mode, and other arrangement orders are used. May be.
- the blue photoelectric conversion element, the photoelectric conversion element of the present invention, and the red photoelectric conversion element may be arranged in this order from the light incident side.
- the photoelectric conversion element of this invention is arrange
- the imaging element has two layers (two colors) or four layers (four colors) or more. It doesn't matter.
- an embodiment in which the photoelectric conversion element 10a of the present invention is arranged on the arranged blue photoelectric conversion element 22 and red photoelectric conversion element 24 may be used as in the image pickup element 20b shown in FIG.
- a color filter that absorbs light of a predetermined wavelength may be further disposed on the light incident side as necessary.
- the form of the image sensor is not limited to the form shown in FIGS. 3 and 4 and may be other forms.
- positioned in the same in-plane position may be sufficient.
- the photoelectric conversion element include, for example, a photovoltaic cell and an optical sensor, but 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 arranged linearly or a two-dimensional sensor arranged on a plane.
- Table 1 shows the absorption maximum wavelength of the obtained absorption spectrum and the width (absorption half-value width) where the absorbance is 0.5 when the absorbance of the absorption maximum is normalized to 1.
- the “corresponding to formula (3)” column is “A” when each compound corresponds to the compound represented by formula (3), and “B” otherwise.
- the column “corresponding to formula (4)” is “A” when each compound corresponds to the compound represented by formula (4), and “B” otherwise.
- a photoelectric conversion element having the form shown in FIG. 1 was produced using the obtained compound.
- the photoelectric conversion element includes the lower electrode 11, the electron blocking film 16 ⁇ / b> A, the photoelectric conversion film 12, and the upper electrode 15.
- an amorphous ITO film is formed on a glass substrate by sputtering to form the lower electrode 11 (thickness: 30 nm), and the following compound (EB-1) is vacuum-coated on the lower electrode 11.
- An electron blocking film 16A (thickness: 30 nm) was formed by heat evaporation.
- the compound (D-1) and fullerene (C 60 ) are deposited on the electron blocking film 16A by a vacuum deposition method so that the single layer equivalent is 100 nm and 50 nm, respectively.
- Co-evaporated to form a film the photoelectric conversion film 12 having a bulk heterostructure of 150 nm was formed.
- an amorphous ITO film was formed on the photoelectric conversion film 12 by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm).
- a SiO film is formed as a sealing layer on the upper electrode 15 by a vacuum deposition method, and then an aluminum oxide (Al 2 O 3 ) layer is formed thereon by an ALCVD (Atomic Layer Chemical Vapor Deposition) method. Was made.
- ALCVD Atomic Layer Chemical Vapor Deposition
- photoelectric conversion elements were produced using the compounds (D-2) to (D-12) and (R-1). As described above, with Compound (R-2), a vapor deposition film was not obtained in the first place, and a photoelectric conversion element could not be produced.
- each obtained photoelectric conversion element was heated on a hot plate at 180 ° C. for 30 minutes.
- a voltage is applied to each photoelectric conversion element after heating so as to have an electric field strength of 2.0 ⁇ 10 5 V / cm, and light is irradiated from the upper electrode (transparent conductive film) side to photoelectric conversion efficiency at 540 nm.
- External quantum efficiency was measured.
- the external quantum efficiency was measured using an Optel constant energy quantum efficiency measuring device. Evaluation was performed based on the relative value of the photoelectric conversion efficiency after heating when the photoelectric conversion efficiency before heating was 1. Evaluation was performed with a relative value of 0.90 or more as A, 0.80 or more and less than 0.90 as B, and less than 0.80 as C. In practice, B or more is preferable, and A is more preferable.
- the absorption half-value width of the photoelectric conversion film in the obtained photoelectric conversion element was evaluated according to the same procedure as described above in ⁇ Measurement of absorption waveform of vapor deposition film>, and the results are shown in Table 2.
- Table 2 the method of notation in the “corresponding to Formula (3)” column and the “corresponding to Formula (4)” column is the same as in Table 1 above.
- the photoelectric conversion element of the present invention has a narrow absorption half-value width and high heat resistance compared to the comparative example.
- the absorption half width is narrower.
- the absorption half It was confirmed that the price range was further narrowed.
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Abstract
Description
光電変換膜を使用した光電変換素子に関しては、例えば、特許文献1において、所定の化合物を含む光電変換膜を有する光電変換素子が開示されている。
本発明者らは、特許文献1に記載の光電変換素子の特性について検討したところ、光電変換素子内の光電変換膜の吸収ピークの半値幅は広く、更なる改良が必要であった。
また、本発明は、撮像素子、光センサ、および、化合物を提供することも課題とする。
光電変換膜が、後述する式(1)で表される化合物を含む、光電変換素子。
(2) 式(1)で表される化合物が、後述する式(2)で表される化合物である、(1)に記載の光電変換素子。
(3) 式(1)で表される化合物が、後述する式(3)で表される化合物である、(1)または(2)に記載の光電変換素子。
(4) 式(1)で表される化合物が、後述する式(4)で表される化合物である、(1)~(3)のいずれかに記載の光電変換素子。
(5) Ra1およびRa2は、それぞれ独立に、炭素数3以上の置換基を表す、(1)~(4)のいずれかに記載の光電変換素子。
(6) Ra1およびRa2は、それぞれ独立に、炭素数3以上の2級アルキル基、炭素数3以上のアリール基、または、炭素数3以上のヘテロアリール基を表す、(1)~(5)のいずれかに記載の光電変換素子。
(7) 光電変換膜が、さらにn型有機半導体を含み、
光電変換膜が、式(1)で表される化合物とn型有機半導体とが混合された状態で形成されるバルクへテロ構造を有する、(1)~(6)のいずれかに記載の光電変換素子。
(8) 導電性膜と透明導電性膜との間に、光電変換膜の他に1種以上の中間層を有する、(1)~(7)のいずれかに記載の光電変換素子。
(9) (1)~(8)のいずれかに記載の光電変換素子を有する、撮像素子。
(10) さらに、光電変換素子が受光する光とは異なる波長の光を受光する他の光電変換素子を有する、(9)に記載の撮像素子。
(11) 光電変換素子と、他の光電変換素子とが積層されており、
入射光の内の少なくとも一部が光電変換素子を透過した後に、他の光電変換素子で受光される、(10)に記載の撮像素子。
(12) 光電変換素子が緑色光電変換素子であり、
他の光電変換素子が、青色光電変換素子および赤色光電変換素子を含む、(10)または(11)に記載の撮像素子。
(13) (1)~(8)のいずれかに記載の光電変換素子を有する、光センサ。
(14) 式(1)で表される化合物。
(15) 式(2)で表される、(14)に記載の化合物。
(16) 式(3)で表される、(14)または(15)に記載の化合物。
(17) 式(4)で表される、(14)~(16)のいずれかに記載の化合物。
(18) Ra1およびRa2は、それぞれ独立に、炭素数3以上の置換基を表す、(14)~(17)のいずれかに記載の化合物。
(19) Ra1およびRa2は、それぞれ独立に、炭素数3以上の2級アルキル基、炭素数3以上のアリール基、または、炭素数3以上のヘテロアリール基を表す、(14)~(18)のいずれかに記載の化合物。
また、本発明によれば、撮像素子、光センサ、および、化合物を提供できる。
なお、本明細書において、置換または無置換を明記していない置換基等については、目的とする効果を損なわない範囲で、その基にさらに置換基(例えば、後述する置換基W)が置換していてもよい。例えば、「アルキル基」という表記は、置換基(例えば、後述する置換基W)が置換していてもよいアルキル基を意味する。
また、本明細書において、「~」を用いて表される数値範囲は、「~」前後に記載される数値を下限値および上限値として含む範囲を意味する。
図1に示す光電変換素子10aは、下部電極として機能する導電性膜(以下、下部電極とも記す)11と、電子ブロッキング膜16Aと、後述する特定化合物を含む光電変換膜12と、上部電極として機能する透明導電性膜(以下、上部電極とも記す)15とがこの順に積層された構成を有する。
図2に別の光電変換素子の構成例を示す。図2に示す光電変換素子10bは、下部電極11上に、電子ブロッキング膜16Aと、光電変換膜12と、正孔ブロッキング膜16Bと、上部電極15とがこの順に積層された構成を有する。なお、図1および図2中の電子ブロッキング膜16A、光電変換膜12、および、正孔ブロッキング膜16Bの積層順は、用途および特性に応じて、適宜変更してもよい。
また、光電変換素子10a(または10b)を使用する場合には、電圧を印加できる。この場合、下部電極11と上部電極15とが一対の電極をなし、この一対の電極間に、1×10-5~1×107V/cmの電圧を印加することが好ましい。性能および消費電力の点から、印加される電圧としては、1×10-4~1×107V/cmがより好ましく、1×10-3~5×106V/cmがさらに好ましい。
なお、電圧印加方法については、図1および図2において、電子ブロッキング膜16A側が陰極となり、光電変換膜12側が陽極となるように印加することが好ましい。光電変換素子10a(または10b)を光センサとして使用した場合、また、撮像素子に組み込んだ場合も、同様の方法により電圧を印加できる。
後段で、詳述するように、光電変換素子10a(または10b)は撮像素子用途に好適に適用できる。
光電変換膜は、光電変換材料として特定化合物を含む膜である。この化合物を使用することにより、吸収ピークの半値幅が狭い光電変換膜を有する光電変換素子が得られる。
以下、特定化合物について詳述する。
なお、式(1)中、R1が結合する炭素原子とそれに隣接する炭素原子とで構成されるC=C二重結合に基づいて区別され得る幾何異性体について、式(1)はそのいずれをも含む。つまり、上記C=C二重結合に基づいて区別されるシス体とトランス体とは、いずれも式(1)に含まれる。
アリール基中の炭素数は特に制限されないが、6~30が好ましく、6~18がより好ましく、6がさらに好ましい。アリール基は、単環構造であっても、2つ以上の環が縮環した縮環構造(縮合環構造)であってもよい。
アリール基としては、例えば、フェニル基、ナフチル基、または、アントリル基が好ましく、フェニル基がより好ましい。
アリール基が有し得る置換基としては後述する置換基Wが挙げられ、例えば、アルキル基が挙げられる。
アリール基は、置換基を複数種類有していてもよい。
アリール基が置換基を有する場合、アリール基が有する置換基の数は特に制限されないが、光電変換膜の吸収ピークの半値幅より狭くなる点(以後、単に「本発明の効果がより優れる点」ともいう。)で、1~5が好ましく、2~3がより好ましい。
ヘテロアリール基は、炭素原子および水素原子以外にヘテロ原子を有する。ヘテロ原子としては、例えば、硫黄原子、酸素原子、窒素原子、セレン原子、テルル原子、リン原子、ケイ素原子、および、ホウ素原子が挙げられ、硫黄原子、酸素原子、または、窒素原子が好ましい。
ヘテロアリール基が有するヘテロ原子の数は特に制限されないが、1~10が好ましく、1~4がより好ましく、1~2がさらに好ましい。
ヘテロアリール基の環員数は特に制限されないが、3~8が好ましく、5~7がより好ましく、5~6がさらに好ましい。なお、ヘテロアリール基は、単環構造であっても、2個以上の環が縮環した縮環構造であってもよい。縮環構造の場合、ヘテロ原子を有さない芳香族炭化水素環(例えば、ベンゼン環)が含まれていてもよい。
ヘテロアリール基としては、例えば、フリル基、ピリジル基、キノリル基、イソキノリル基、アクリジニル基、フェナントリジニル基、プテリジニル基、ピラジニル基、キノキサリニル基、ピリミジニル基、キナゾリル基、ピリダジニル基、シンノリニル基、フタラジニル基、トリアジニル基、オキサゾリル基、ベンゾオキサゾリル基、チアゾリル基、ベンゾチアゾリル基、イミダゾリル基、ベンゾイミダゾリル基、ピラゾリル基、インダゾリル基、イソオキサゾリル基、ベンゾイソオキサゾリル基、イソチアゾリル基、ベンゾイソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、テトラゾリル基、ベンゾフリル基、チエニル基、ベンゾチエニル基、ジベンゾフリル基、ジベンゾチエニル基、ピロリル基、インドリル基、イミダゾピリジニル基、および、カルバゾリル基が挙げられる。
中でも、フリル基、チエニル基、ピリジル基、キノリル基、イソキノリル基、または、カルバゾリル基が好ましい。
ヘテロアリール基が置換基を有する場合、ヘテロアリール基が有する置換基の数は特に制限されないが、1~5が好ましく、1~3がより好ましい。
上記置換基の定義は、後述する置換基Wと同義である。置換基としては、例えば、アルキル基、アリール基、および、ヘテロアリール基が挙げられる。
炭素数2以上の置換基に含まれる炭素数は、本発明の効果がより優れる点で、3以上が好ましい。つまり、炭素数2以上の置換基は、炭素数3以上の置換基であることが好ましい。炭素数の上限は特に制限されないが、10以下が挙げられる。
上記炭素数2以上の置換基としては、例えば、ヘテロ原子を含んでいてもよい炭素数2以上の脂肪族炭化水素基、および、炭素数2以上の芳香族基が挙げられる。
脂肪族炭化水素基としては、例えば、アルキル基、アルケニル基、および、アルキニル基が挙げられる。これらの基には、酸素原子、窒素原子、および、硫黄原子等のヘテロ原子が含まれていてもよい。
芳香族基としては、アリール基およびヘテロアリール基が挙げられる。
2級アルキル基とは、2級炭素原子を有するアルキル基を意味する。
炭素数3以上の2級アルキル基としては、例えば、イソプロピル基、イソブチル基、ペンタン-2-イル基、ペンタン-3-イル基、および、3-メチル-2-ペンチル基が挙げられる。
炭素数3以上のアリール基としては、Ar1で表されるアリール基で例示した基が挙げられる。
炭素数3以上のヘテロアリール基としては、Ar1で表されるヘテロアリール基で例示した基が挙げられる。
芳香環は、単環であっても、多環であってもよい。
芳香環としては、芳香族炭化水素環および芳香族複素環が挙げられる。芳香族炭化水素環としては、例えば、ベンゼン環、ナフタレン環、アントラセン環、および、フェナントレン環が挙げられる。芳香族複素環としては、例えば、ピロール環、フラン環、チオフェン環、イミダゾール環、および、オキサゾール環が挙げられる。
なかでも、本発明の効果がより優れる点で、芳香族炭化水素環が好ましく、ベンゼン環がより好ましい。
置換基の定義は、後述する置換基Wと同義である。置換基としては、例えば、アルキル基、アリール基、および、ヘテロアリール基が挙げられる。これらの基は、さらに置換基を有していてもよい。
A1は、少なくとも2つの炭素原子を含む環を表す。なお、2つの炭素原子とは、式(1-1)中に明示されるカルボニル基中の炭素原子と、上記カルボニル基の炭素原子に隣接する、式(1-1)中に明示された炭素原子とを意図し、いずれの炭素原子もA1を構成する原子である。
また、上記環は、環を構成する炭素原子が、他のカルボニル炭素(>C=O)、またはチオカルボニル炭素(>C=S)で置換されていてもよい。なお、ここでいう他のカルボニル炭素(>C=O)とは、環を構成する炭素原子が、式(1-1)中に明示されるカルボニル炭素以外に有しているカルボニル炭素を意図する。
A1は、ヘテロ原子を有していてもよく、例えば、窒素原子、硫黄原子、酸素原子、セレン原子、テルル原子、リン原子、ケイ素原子、および、ホウ素原子が挙げられ、窒素原子、硫黄原子、または、酸素原子が好ましく、酸素原子がより好ましい。
A1中のヘテロ原子の数は、0~10が好ましく、0~5がより好ましく、0~2がさらに好ましい。なお、上記ヘテロ原子の数は、A1で表される環を構成する炭素原子がカルボニル炭素(>C=O)またはチオカルボニル炭素(>C=S)で置換されることにより環に導入されているヘテロ原子(式(1-1)中に明示されているカルボニル炭素を含む意図である)の数、および、A1の置換基が有するヘテロ原子の数を含まない数である。
A1は置換基を有していてもよく、置換基としては、ハロゲン原子(好ましくは塩素原子)、アルキル基(直鎖状、分岐鎖状、および環状のいずれであってもよい。炭素数は、1~10が好ましく、1~6がより好ましい)、アリール基(炭素数は、6~18が好ましく、6がより好ましい。)、ヘテロアリール基(炭素数は、5~18が好ましく、5~6がより好ましい)、または、シリル基(直鎖状、分岐鎖状、および環状のいずれであってもよい。ケイ素数は、1~4が好ましく、1がより好ましい)が好ましい。
A1は、芳香族性を示してもよく、示さなくてもよい。
A1は、単環構造でもよく、縮環構造でもよいが、5員環、6員環、または、5員環および6員環の少なくともいずれかを含む縮合環であるのが好ましい。上記縮合環を形成する環の数は、1~4が好ましく、1~3がより好ましい。
(a)1,3-ジカルボニル核:例えば、1,3-インダンジオン核、1,3-シクロヘキサンジオン、5,5-ジメチル-1,3-シクロヘキサンジオン、および、1,3-ジオキサン-4,6-ジオン等。
(b)ピラゾリノン核:例えば、1-フェニル-2-ピラゾリン-5-オン、3-メチル-1-フェニル-2-ピラゾリン-5-オン、および、1-(2-ベンゾチアゾリル)-3-メチル-2-ピラゾリン-5-オン等。
(c)イソオキサゾリノン核:例えば、3-フェニル-2-イソオキサゾリン-5-オン、および、3-メチル-2-イソオキサゾリン-5-オン等。
(d)オキシインドール核:例えば、1-アルキル-2,3-ジヒドロ-2-オキシインドール等。
(e)2,4,6-トリオキソヘキサヒドロピリミジン核:例えば、バルビツール酸または2-チオバルビツール酸、および、その誘導体等。誘導体としては、例えば、1-メチル、1-エチル等の1-アルキル体、1,3-ジメチル、1,3-ジエチル、および、1,3-ジブチル等の1,3-ジアルキル体、1,3-ジフェニル、1,3-ジ(p-クロロフェニル)、および、1,3-ジ(p-エトキシカルボニルフェニル)等の1,3-ジアリール体、1-エチル-3-フェニル等の1-アルキル-1-アリール体、並びに、1,3-ジ(2-ピリジル)等の1,3-ジヘテロアリール体等が挙げられる。
(f)2-チオ-2,4-チアゾリジンジオン核:例えば、ローダニンおよびその誘導体等。誘導体としては、例えば、3-メチルローダニン、3-エチルローダニン、および、3-アリルローダニン等の3-アルキルローダニン、3-フェニルローダニン等の3-アリールローダニン、並びに、3-(2-ピリジル)ローダニン等の3-ヘテロアリールローダニン等が挙げられる。
(g)2-チオ-2,4-オキサゾリジンジオン核(2-チオ-2,4-(3H,5H)-オキサゾールジオン核):例えば、3-エチル-2-チオ-2,4-オキサゾリジンジオン等。
(h)チアナフテノン核:例えば、3(2H)-チアナフテノン-1,1-ジオキサイド等。
(i)2-チオ-2,5-チアゾリジンジオン核:例えば、3-エチル-2-チオ-2,5-チアゾリジンジオン等。
(j)2,4-チアゾリジンジオン核:例えば、2,4-チアゾリジンジオン、3-エチル-2,4-チアゾリジンジオン、および、3-フェニル-2,4-チアゾリジンジオン等。
(k)チアゾリン-4-オン核:例えば、4-チアゾリノン、および、2-エチル-4-チアゾリノン等。
(l)2,4-イミダゾリジンジオン(ヒダントイン)核:例えば、2,4-イミダゾリジンジオン、および、3-エチル-2,4-イミダゾリジンジオン等。
(m)2-チオ-2,4-イミダゾリジンジオン(2-チオヒダントイン)核:例えば、2-チオ-2,4-イミダゾリジンジオン、および、3-エチル-2-チオ-2,4-イミダゾリジンジオン等。
(n)イミダゾリン-5-オン核:例えば、2-プロピルメルカプト-2-イミダゾリン-5-オン等。
(o)3,5-ピラゾリジンジオン核:例えば、1,2-ジフェニル-3,5-ピラゾリジンジオン、および、1,2-ジメチル-3,5-ピラゾリジンジオン等。
(p)ベンゾチオフェン-3(2H)-オン核:例えば、ベンゾチオフェン-3(2H)-オン、オキソベンゾチオフェン-3(2H)-オン、および、ジオキソベンゾチオフェンー3(2H)-オン等。
(q)インダノン核:例えば、1-インダノン、3-フェニル-1-インダノン、3-メチル-1-インダノン、3,3-ジフェニル-1-インダノン、および、3,3-ジメチル-1-インダノン等。
(r)ベンゾフラン-3-(2H)-オン核:例えば、ベンゾフラン-3-(2H)-オン等。
(s)2,2-ジヒドロフェナレン-1,3-ジオン核等。
Rd1は、アルキル基またはアリール基を表す。
Ra1およびRa2は互いに結合して環を形成する場合、結果として、Ra1およびRa2を含み形成される構造に含まれる炭素数は4以上となる。
Ra1およびRa2が互いに結合して形成される環としては、芳香環(芳香族炭化水素環または芳香族複素環)および非芳香環が挙げられる。
芳香環としては、例えば、ベンゼン環、および、フルオレン環が挙げられる。
Ra3およびRa4は、それぞれ独立に、炭素数2以上の2価の置換基を表す。
炭素数2以上の2価の置換基に含まれる炭素数は、本発明の効果がより優れる点で、3以上が好ましい。つまり、炭素数2以上の2価の置換基は、炭素数3以上の2価の置換基であることが好ましい。炭素数の上限は特に制限されないが、10以下が挙げられる。
上記炭素数2以上の2価の置換基としては、例えば、ヘテロ原子を含んでいてもよい炭素数2以上の2価の脂肪族炭化水素基、および、炭素数2以上の2価の芳香族基が挙げられる。
脂肪族炭化水素基としては、例えば、アルキレン基、アルケニレン基、および、アルキニレン基が挙げられる。これらの基には、酸素原子、窒素原子、および、硫黄原子等のヘテロ原子が含まれていてもよい。
芳香族基としては、アリーレン基およびヘテロアリーレン基が挙げられる。
なかでも、本発明の効果がより優れる点で、炭素数3以上のアリーレン基(例えば、フェニレン基)、または、炭素数3以上のヘテロアリーレン基が好ましい。
より具体的には、特定化合物中の置換基として、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも含まれない。
R3~R5は、それぞれ独立に、水素原子または置換基を表す。置換基の定義は、後述する置換基Wと同義である。
なお、式(2)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
式(2-1)中、Ra3、Ra4、および、L2の定義は、式(1-3)中の各基の定義と同じである。
なお、式(2-1)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
R6~R13は、それぞれ独立に、水素原子または置換基を表す。置換基の定義は、後述する置換基Wと同義である。
R10とR11、R11とR12、R12とR13は、それぞれ独立に、互いに結合して環を形成してもよい。形成される環の種類は、芳香環(芳香族炭化水素環または芳香族複素環)および非芳香環が挙げられる。芳香環としては、例えば、ベンゼン環、および、フルオレン環が挙げられる。
なお、式(3)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
式(3-1)中、Ra3、Ra4、および、L2の定義は、式(1-3)中の各基の定義と同じである。
なお、式(3-1)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
R14~R16は、それぞれ独立に、水素原子または置換基を表す。置換基の定義は、後述する置換基Wと同義である。
Rc1およびRc2は、それぞれ独立に、水素原子または置換基を表し、Rc1およびRc2の少なくとも一方は置換基を表す。置換基の定義は、後述する置換基Wと同義である。置換基としては、例えば、アルキル基、アリール基、および、ヘテロアリール基が挙げられる。
なお、式(4)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
式(4-1)中、Ra3、Ra4、および、L2の定義は、式(1-3)中の各基の定義と同じである。
なお、式(4-1)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。
本明細書における置換基Wについて記載する。
置換基Wとしては、例えば、ハロゲン原子(フッ素原子、塩素原子、臭素原子、および、ヨウ素原子等)、アルキル基(シクロアルキル基、ビシクロアルキル基、および、トリシクロアルキル基を含む)、アルケニル基(シクロアルケニル基、および、ビシクロアルケニル基を含む)、アルキニル基、アリール基、複素環基(ヘテロ環基といってもよい。ヘテロアリール基を含む)、シアノ基、ヒドロキシ基、ニトロ基、アルコキシ基、アリールオキシ基、シリルオキシ基、ヘテロ環オキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、アミノ基(アニリノ基を含む)、アンモニオ基、アシルアミノ基、アミノカルボニルアミノ基、アルコキシカルボニルアミノ基、アリールオキシカルボニルアミノ基、スルファモイルアミノ基、アルキルまたはアリールスルホニルアミノ基、メルカプト基、アルキルチオ基、アリールチオ基、ヘテロ環チオ基、スルファモイル基、アルキルまたはアリールスルフィニル基、アルキルまたはアリールスルホニル基、アシル基、アリールオキシカルボニル基、アルコキシカルボニル基、カルバモイル基、アリールまたはヘテロ環アゾ基、イミド基、ホスフィノ基、ホスフィニル基、ホスフィニルオキシ基、ホスフィニルアミノ基、ホスホノ基、シリル基、ヒドラジノ基、ウレイド基、および、ボロン酸基(-B(OH)2)が挙げられる。
また、置換基Wは、さらに置換基Wで置換されていてもよい。例えば、アルキル基にハロゲン原子が置換していてもよい。
特定化合物の吸収半値幅は特に制限されないが、本発明の光電変換素子中の光電変換膜が緑色光を受光(吸収)して光電変換する有機光電変換膜として好適に用いられる点で、95nm以下が好ましく、90nm以下がより好ましく、85nm以下がさらに好ましい。下限は特に制限されないが、60nm以上の場合が多い。
なお、上記極大吸収波長および吸収半値幅は、特定化合物の膜(例えば、特定化合物の蒸着膜)の状態で測定した値である。
光電変換膜は、上述した特定化合物以外の他の成分として、n型有機半導体を含むのが好ましい。
n型有機半導体は、アクセプタ性有機半導体材料(化合物)であり、電子を受容しやすい性質がある有機化合物をいう。さらに詳しくは、n型有機半導体は、2つの有機化合物を接触させて用いた場合に電子親和力の大きい方の有機化合物をいう。
n型有機半導体としては、例えば、縮合芳香族炭素環化合物(例えば、フラーレン、ナフタレン誘導体、アントラセン誘導体、フェナントレン誘導体、テトラセン誘導体、ピレン誘導体、ペリレン誘導体、および、フルオランテン誘導体);窒素原子、酸素原子、および、硫黄原子の少なくとも1つを有する5~7員環のヘテロ環化合物(例えば、ピリジン、ピラジン、ピリミジン、ピリダジン、トリアジン、キノリン、キノキサリン、キナゾリン、フタラジン、シンノリン、イソキノリン、プテリジン、アクリジン、フェナジン、フェナントロリン、テトラゾール、ピラゾール、イミダゾール、および、チアゾール等);ポリアリーレン化合物;フルオレン化合物;シクロペンタジエン化合物;シリル化合物;並びに、含窒素ヘテロ環化合物を配位子として有する金属錯体等が挙げられる。
なお、光電変換膜は、実質的に、特定化合物とn型有機半導体とから構成されるのが好ましい。実質的とは、光電変換膜全質量に対して、特定化合物およびn型有機半導体の合計含有量が95質量%以上であることを意図する。
光電変換膜は、主に、乾式成膜法により成膜できる。乾式成膜法としては、例えば、蒸着法(特に、真空蒸着法)、スパッタ法、イオンプレーティング法、および、MBE(Molecular Beam Epitaxy)法等の物理気相成長法、並びに、プラズマ重合等のCVD(Chemical Vapor Deposition)法が挙げられる。なかでも、真空蒸着法が好ましい。真空蒸着法により光電変換膜を成膜する場合、真空度および蒸着温度等の製造条件は常法に従って設定できる。
電極(上部電極(透明導電性膜)15と下部電極(導電性膜)11)は、導電性材料から構成される。導電性材料としては、金属、合金、金属酸化物、電気伝導性化合物、およびこれらの混合物等が挙げられる。
上部電極15から光が入射されるため、上部電極15は検知したい光に対し透明であるのが好ましい。上部電極15を構成する材料としては、例えば、アンチモンまたはフッ素等をドープした酸化錫(ATO:Antimony Tin Oxide、FTO:Fluorine doped Tin Oxide)、酸化錫、酸化亜鉛、酸化インジウム、酸化インジウム錫(ITO:Indium Tin Oxide)、および、酸化亜鉛インジウム(IZO:Indium zinc oxide)等の導電性金属酸化物;金、銀、クロム、および、ニッケル等の金属薄膜;これらの金属と導電性金属酸化物との混合物または積層物;ならびに、ポリアニリン、ポリチオフェン、および、ポリピロール等の有機導電性材料、等が挙げられる。なかでも、高導電性および透明性等の点から、導電性金属酸化物が好ましい。
電極の材料がITOの場合、電子ビーム法、スパッタ法、抵抗加熱蒸着法、化学反応法(ゾル-ゲル法等)、および、酸化インジウムスズの分散物の塗布等の方法が挙げられる。
本発明の光電変換素子は、導電性膜と透明導電性膜との間に、光電変換膜の他に1種以上の中間層を有しているのも好ましい。上記中間層としては、電荷ブロッキング膜が挙げられる。光電変換素子がこの膜を有することにより、得られる光電変換素子の特性(光電変換効率および応答性等)がより優れる。電荷ブロッキング膜としては、電子ブロッキング膜と正孔ブロッキング膜とが挙げられる。以下に、それぞれの膜について詳述する。
電子ブロッキング膜は、電子供与性化合物を含む。
具体的には、低分子材料としては、例えば、N,N’-ビス(3-メチルフェニル)-(1,1’-ビフェニル)-4,4’-ジアミン(TPD)、および、4,4’-ビス[N-(ナフチル)-N-フェニル-アミノ]ビフェニル(α-NPD)等の芳香族ジアミン化合物;ポルフィリン、テトラフェニルポルフィリン銅、フタロシアニン、銅フタロシアニン、および、チタニウムフタロシアニンオキサイド等のポルフィリン化合物;並びに、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、スチルベン誘導体、ピラゾリン誘導体、テトラヒドロイミダゾール、ポリアリールアルカン、ブタジエン、4,4’,4’’-トリス(N-(3-メチルフェニル)N-フェニルアミノ)トリフェニルアミン(m-MTDATA)、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体、ピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、および、シラザン誘導体等が挙げられる。
高分子材料としては、例えば、フェニレンビニレン、フルオレン、カルバゾール、インドール、ピレン、ピロール、ピコリン、チオフェン、アセチレン、および、ジアセチレン等の重合体、並びに、その誘導体が挙げられる。また、特許第5597450号の段落[0049]~[0063]に記載の化合物、特開2011-225544号公報の段落[0119]~[0158]に記載の化合物、および、特開2012-94660号公報の段落[0086]~[0090]に記載の化合物が挙げられる。
電子ブロッキング膜は、無機材料で構成されていてもよい。一般的に、無機材料は有機材料よりも誘電率が大きいため、無機材料を電子ブロッキング膜に用いた場合に、光電変換膜に電圧が多くかかるようになり、光電変換効率が高くなる。電子ブロッキング膜となりうる無機材料としては、例えば、酸化カルシウム、酸化クロム、酸化クロム銅、酸化マンガン、酸化コバルト、酸化ニッケル、酸化銅、酸化ガリウム銅、酸化ストロンチウム銅、酸化ニオブ、酸化モリブデン、酸化インジウム銅、酸化インジウム銀、および、酸化イリジウムが挙げられる。
正孔ブロッキング膜は、電子受容性化合物を含む。
電子受容性化合物としては、例えば、1,3-ビス(4-tert-ブチルフェニル-1,3,4-オキサジアゾリル)フェニレン(OXD-7)等のオキサジアゾール誘導体;アントラキノジメタン誘導体;ジフェニルキノン誘導体;バソクプロイン、バソフェナントロリン、およびこれらの誘導体;トリアゾール化合物;トリス(8-ヒドロキシキノリナート)アルミニウム錯体;ビス(4-メチル-8-キノリナート)アルミニウム錯体;ジスチリルアリーレン誘導体;並びに、シロール化合物が挙げられる。また、特開2006-100767号公報の段落[0056]~[0057]に記載の化合物が挙げられる。
光電変換素子は、さらに基板を有していてもよい。使用される基板の種類は特に制限されないが、半導体基板、ガラス基板、および、プラスチック基板が挙げられる。
なお、基板の位置は特に制限されないが、通常、基板上に導電性膜、光電変換膜、および透明導電性膜をこの順で積層する。
光電変換素子は、さらに封止層を有していてもよい。光電変換材料は水分子等の劣化因子の存在で顕著にその性能が劣化してしまうことがある。そこで、水分子を浸透させない緻密な金属酸化物、金属窒化物、もしくは、金属窒化酸化物等のセラミクス、または、ダイヤモンド状炭素(DLC:Diamond-like Carbon)等の封止層で光電変換膜全体を被覆して封止することで、上記劣化を防止できる。
なお、封止層としては、特開2011-082508号公報の段落[0210]~[0215]に記載に従って、材料の選択および製造を行ってもよい。
光電変換素子の用途として、例えば、撮像素子が挙げられる。撮像素子とは、画像の光情報を電気信号に変換する素子であり、通常、複数の光電変換素子が含まれる。
図3は、本発明の一実施形態を説明するための撮像素子の概略構成を示す断面模式図である。この撮像素子は、デジタルカメラおよびデジタルビデオカメラ等の撮像素子、電子内視鏡、ならびに、携帯電話機等の撮像モジュール等に搭載される。
図3に示す撮像素子20aは、本発明の光電変換素子10aと、青色光電変換素子22と、赤色光電変換素子24とを含み、これらは光が入射する方向に沿って積層されている。光電変換素子10aは、上述したように、主に、緑色光を受光できる緑色光電変換素子として機能できる。
撮像素子20aは、いわゆる積層体型の色分離撮像素子である。光電変換素子10a、青色光電変換素子22、および、赤色光電変換素子24は、それぞれ検出する波長スペクトルが異なる。つまり、青色光電変換素子22および赤色光電変換素子24は、光電変換素子10aが受光(吸収)する光とは異なる波長の光を受光する光電変換素子に該当する。光電変換素子10aでは緑色光を受光でき、青色光電変換素子22では青色光を受光でき、赤色光電変換素子では赤色光を受光できる。
なお、緑色光とは波長500~600nmの範囲の光を、青色光とは波長400~500nmの範囲の光を、赤色光とは波長600~700nmの範囲の光を意図する。
撮像素子20aに矢印の方向から光が入射すると、まず、光電変換素子10aにおいて緑色光が吸収されるが、青色光および赤色光に関しては光電変換素子10aを透過する。光電変換素子10aを透過した光が青色光電変換素子22に進んだ際には、青色光が吸収されるが、赤色光に関しては青色光電変換素子22を透過する。その後、青色光電変換素子22を透過した光は、赤色光電変換素子24によって吸収される。このように積層型の色分離撮像素子である撮像素子20aにおいては、緑、青、および、赤の3つの受光部で1つの画素を構成でき、受光部の面積を大きく取れる。
特に、本発明の光電変換素子10aにおいては、上述したように、吸収ピークの半値幅が狭いため、青色光および赤色光の吸収が略生じず、青色光電変換素子22および赤色光電変換素子24での検出性に影響を与えにくい。
青色光電変換膜の種類は、青色光を受光できる光電変換膜であれば特に制限されないが、有機系の青色光電変換膜または無機系の青色光電変換膜が挙げられ、有機系の青色光電変換膜(有機化合物で構成される青色光電変換膜)が好ましい。
青色光電変換膜の極大吸収波長は特に制限されないが、400~500nmの範囲にあるのが好ましく、420~480nmの範囲にあるのがより好ましい。
導電性膜および透明導電性膜としては、本発明の光電変換素子に含まれる導電性膜および透明導電性膜を用いることができる。
赤色光電変換膜の種類は、赤色光を受光できる光電変換膜であれば特に制限されないが、有機系の赤色光電変換膜または無機系の赤色光電変換膜が挙げられ、有機系の赤色光電変換膜(有機化合物で構成される赤色光電変換膜)が好ましい。
赤色光電変換膜の極大吸収波長は特に制限されないが、600~700nmの範囲にあるのが好ましく、620~680nmnmの範囲にあるのがより好ましい。
導電性膜および透明導電性膜としては、本発明の光電変換素子に含まれる導電性膜および透明導電性膜を用いることができる。
なかでも、本発明の光電変換素子が最も光の入射側に配置されることが好ましい。この場合、入射光の内の少なくとも一部が本発明の光電変換素子を透過した後に、他の光電変換素子で受光される。
たとえば、図4に示す撮像素子20bのように、配列した青色光電変換素子22と赤色光電変換素子24の上に本発明の光電変換素子10aを配置する態様であってもよい。なお、図4の態様の場合、必要に応じて、光の入射側にさらに所定の波長の光を吸収するカラーフィルタを配置してもよい。
例えば、同一面内位置に、本発明の光電変換素子、青色光電変換素子、および、赤色光電変換素子が配置された態様であってもよい。
以下、化合物(D-1)の合成例を一例として、式(1)で表される化合物の合成方法を示す。
化合物(D-1)は、以下のスキームに従って、合成した。
得られた化合物(D-1)はNMRおよびMS(Mass Spectrometry)により同定した。
1H NMRスペクトル(400MHz、CDCl3)を図5に示す。
1MS(ESI+)m/z:656.3([M+H]+)
以下に、化合物(D-1)~(D-12)、および、比較化合物(R-1)~(R-2)の構造を示す。
ガラス基板の温度を25℃に制御した状態で、真空蒸着法により得られた化合物(D-1~D-12、R-1~R-2)をそれぞれ蒸着して成膜し、ガラス基板上に厚みが100nmの蒸着膜を形成した。
得られた蒸着膜の吸収形状を日立ハイテック社製、分光光度計U3310を用いて測定した。得られた吸収スペクトルの吸収極大波長、および、吸収極大の吸光度を1に規格化した場合における吸光度が0.5の幅(吸収半値幅)を表1に示す。
なお、表1中、「式(3)に該当」欄は、各化合物が式(3)で表される化合物に該当する場合は「A」、該当しない場合は「B」とする。
なお、表1中、「式(4)に該当」欄は、各化合物が式(4)で表される化合物に該当する場合は「A」、該当しない場合は「B」とする。
なお、化合物(R-2)を用いた場合には、蒸着膜を得ることができなかった。
得られた化合物を用いて図1の形態の光電変換素子を作製した。ここで、光電変換素子は、下部電極11、電子ブロッキング膜16A、光電変換膜12および上部電極15からなる。
具体的には、ガラス基板上に、アモルファス性ITOをスパッタ法により成膜して、下部電極11(厚み:30nm)を形成し、さらに下部電極11上に下記の化合物(EB-1)を真空加熱蒸着法により成膜して、電子ブロッキング膜16A(厚み:30nm)を形成した。
さらに、基板の温度を25℃に制御した状態で、電子ブロッキング膜16A上に化合物(D-1)とフラーレン(C60)とをそれぞれ単層換算で100nm、50nmとなるように真空蒸着法により共蒸着して成膜し、150nmのバルクヘテロ構造を有する光電変換膜12を形成した。
さらに、光電変換膜12上に、アモルファス性ITOをスパッタ法により成膜して、上部電極15(透明導電性膜)(厚み:10nm)を形成した。上部電極15上に、真空蒸着法により封止層としてSiO膜を形成した後、その上にALCVD(Atomic Layer Chemical Vapor Deposition)法により酸化アルミニウム(Al2O3)層を形成し、光電変換素子を作製した。
なお、上述したように、化合物(R-2)では、そもそも蒸着膜が得られず、光電変換素子を作製できなかった。
得られた各光電変換素子の駆動の確認をした。各光電変換素子に2.0×105V/cmの電界強度となるように電圧を印加した。その後、上部電極(透明導電性膜)側から光を照射して540nmでの光電変換効率(外部量子効率)を測定したところ、化合物(D-1)~(D-10)および(R-1)を用いて作製した光電変換素子はいずれも60%以上の光電変換効率を示し、光電変換素子として十分な外部量子効率を有することを確認した。外部量子効率は、オプテル製定エネルギー量子効率測定装置を用いて測定した。照射した光量は50μW/cm2であった。
得られた各光電変換素子の耐熱性評価を行った。具体的には、得られた各光電変換素子をホットプレート上で180℃で30分間加熱した。加熱後の各光電変換素子に2.0×105V/cmの電界強度となるように電圧を印加し、上部電極(透明導電性膜)側から光を照射して540nmでの光電変換効率(外部量子効率)の測定を行った。外部量子効率は、オプテル製定エネルギー量子効率測定装置を用いて測定した。加熱前の光電変換効率を1とした場合の加熱後の光電変換効率の相対値で評価を行った。相対値が0.90以上のものをA、0.80以上0.90未満のものをB、0.80未満のものをCとして評価を行った。なお、実用上、B以上が好ましく、Aがより好ましい。
なお、表2中、「式(3)に該当」欄および「式(4)に該当」欄の表記の仕方は、上述した表1と同じである。
なかでも、上記実施例に示すように、式(3)で表される化合物を用いた場合、吸収半値幅より狭くなり、さらに、式(4)で表される化合物を用いた場合、吸収半値幅がさらに狭くなることが確認された。
化合物(D-1)~(D-12)を用いて、図3に示す形態と同様の撮像素子をそれぞれ作製した。
緑色光電変換素子として機能する上記光電変換素子は、上述した方法により作製した。
なお、青色光電変換素子および赤色光電変換素子は、特開2005-303266号公報に記載の参考にして作製した。
得られた撮像素子においては、本発明の光電変換素子中の光電変換膜の吸収ピークの半値幅が狭いため、青色光電変換素子および赤色光電変換素子での受光がしやすく、色分離性能に優れていた。
11 導電性膜(下部電極)
12 光電変換膜
15 透明導電性膜(上部電極)
16A 電子ブロッキング膜
16B 正孔ブロッキング膜
20a,20b 撮像素子
22 青色光電変換素子
24 赤色光電変換素子
Claims (19)
- 導電性膜、光電変換膜、および、透明導電性膜をこの順で有する光電変換素子であって、
前記光電変換膜が、式(1)で表される化合物を含む、光電変換素子。
式(1)中、Ar1は、置換基を有してもよいアリール基、または、置換基を有してもよいヘテロアリール基を表す。R1は、水素原子または置換基を表す。X1~X3は、それぞれ独立に、CR2または窒素原子を表す。R2は、水素原子または置換基を表す。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。L1は、炭素原子、ケイ素原子、または、ゲルマニウム原子を表す。B1は、置換基を有してもよい芳香環を表す。Yは、式(1-1)で表される基、または、式(1-2)で表される基を表す。A1は、少なくとも2つの炭素原子を含む環を表す。Rb1およびRb2は、それぞれ独立に、シアノ基または-COORd1を表す。Rd1は、アルキル基またはアリール基を表す。*は、結合位置を表す。
ただし、式(1)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - 前記式(1)で表される化合物が、式(2)で表される化合物である、請求項1に記載の光電変換素子。
式(2)中、Ar1は、置換基を有してもよいアリール基、または、置換基を有してもよいヘテロアリール基を表す。R1およびR3~R5は、それぞれ独立に、水素原子または置換基を表す。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。B1は、置換基を有してもよい芳香環を表す。A1は、少なくとも2つの炭素原子を含む環を表す。
ただし、式(2)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - 前記式(1)で表される化合物が、式(3)で表される化合物である、請求項1または2に記載の光電変換素子。
式(3)中、Ar1は、置換基を有してもよいアリール基、または、置換基を有してもよいヘテロアリール基を表す。R1およびR3~R13は、それぞれ独立に、水素原子または置換基を表す。R10とR11、R11とR12、R12とR13は、それぞれ独立に、互いに結合して環を形成してもよい。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。
ただし、式(3)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - 前記式(1)で表される化合物が、式(4)で表される化合物である、請求項1~3のいずれか1項に記載の光電変換素子。
式(4)中、R1およびR3~R16は、それぞれ独立に、水素原子または置換基を表す。R10とR11、R11とR12、R12とR13は、それぞれ独立に、互いに結合して環を形成してもよい。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。Rc1およびRc2は、それぞれ独立に、水素原子または置換基を表し、Rc1およびRc2の少なくとも一方は置換基を表す。
ただし、式(4)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - Ra1およびRa2は、それぞれ独立に、炭素数3以上の置換基を表す、請求項1~4のいずれか1項に記載の光電変換素子。
- Ra1およびRa2は、それぞれ独立に、炭素数3以上の2級アルキル基、炭素数3以上のアリール基、または、炭素数3以上のヘテロアリール基を表す、請求項1~5のいずれか1項に記載の光電変換素子。
- 前記光電変換膜が、さらにn型有機半導体を含み、
前記光電変換膜が、前記式(1)で表される化合物と前記n型有機半導体とが混合された状態で形成されるバルクへテロ構造を有する、請求項1~6のいずれか1項に記載の光電変換素子。 - 前記導電性膜と前記透明導電性膜との間に、前記光電変換膜の他に1種以上の中間層を有する、請求項1~7のいずれか1項に記載の光電変換素子。
- 請求項1~8のいずれか1項に記載の光電変換素子を有する、撮像素子。
- さらに、前記光電変換素子が受光する光とは異なる波長の光を受光する他の光電変換素子を有する、請求項9に記載の撮像素子。
- 前記光電変換素子と、前記他の光電変換素子とが積層されており、
入射光の内の少なくとも一部が前記光電変換素子を透過した後に、前記他の光電変換素子で受光される、請求項10に記載の撮像素子。 - 前記光電変換素子が緑色光電変換素子であり、
前記他の光電変換素子が、青色光電変換素子および赤色光電変換素子を含む、請求項10または11に記載の撮像素子。 - 請求項1~8のいずれか1項に記載の光電変換素子を有する、光センサ。
- 式(1)で表される化合物。
式(1)中、Ar1は、置換基を有してもよいアリール基、または、置換基を有してもよいヘテロアリール基を表す。R1は、水素原子または置換基を表す。X1~X3は、それぞれ独立に、CR2または窒素原子を表す。R2は、水素原子または置換基を表す。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。L1は、炭素原子、ケイ素原子、または、ゲルマニウム原子を表す。B1は、置換基を有してもよい芳香環を表す。Yは、式(1-1)で表される基、または、式(1-2)で表される基を表す。A1は、少なくとも2つの炭素原子を含む環を表す。Rb1およびRb2は、それぞれ独立に、シアノ基または-COORd1を表す。Rd1は、アルキル基またはアリール基を表す。を表す。*は、結合位置を表す。
ただし、式(1)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - 式(3)で表される、請求項14または15に記載の化合物。
式(3)中、Ar1は、置換基を有してもよいアリール基、または、置換基を有してもよいヘテロアリール基を表す。R1およびR3~R13は、それぞれ独立に、水素原子または置換基を表す。R10とR11、R11とR12、R12とR13は、それぞれ独立に、互いに結合して環を形成してもよい。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。
ただし、式(3)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - 式(4)で表される、請求項14~16のいずれか1項に記載の化合物。
式(4)中、R1およびR3~R16は、それぞれ独立に、水素原子または置換基を表す。R10とR11、R11とR12、R12とR13は、それぞれ独立に、互いに結合して環を形成してもよい。Ra1およびRa2は、それぞれ独立に、炭素数2以上の置換基を表す。Ra1およびRa2は、互いに結合して環を形成してもよい。Rc1およびRc2は、それぞれ独立に、水素原子または置換基を表し、Rc1およびRc2の少なくとも一方は置換基を表す。
ただし、式(4)で表される化合物は、カルボキシ基、カルボキシ基の塩、リン酸基、リン酸基の塩、スルホン酸基、および、スルホン酸基の塩のいずれも有さない。 - Ra1およびRa2は、それぞれ独立に、炭素数3以上の置換基を表す、請求項14~17のいずれか1項に記載の化合物。
- Ra1およびRa2は、それぞれ独立に、炭素数3以上の2級アルキル基、炭素数3以上のアリール基、または、炭素数3以上のヘテロアリール基を表す、請求項14~18のいずれか1項に記載の化合物。
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