WO2011052726A1 - Composition et élément électronique - Google Patents

Composition et élément électronique Download PDF

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WO2011052726A1
WO2011052726A1 PCT/JP2010/069296 JP2010069296W WO2011052726A1 WO 2011052726 A1 WO2011052726 A1 WO 2011052726A1 JP 2010069296 W JP2010069296 W JP 2010069296W WO 2011052726 A1 WO2011052726 A1 WO 2011052726A1
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substituted
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研 吉村
健一郎 大家
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住友化学株式会社
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    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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Definitions

  • the present invention relates to a composition using a compound having a specific structure.
  • organic thin-film electronic devices which are one aspect of electronic devices, can eliminate the high-temperature and high-vacuum processes used in the manufacturing process of silicon-based electronic devices, and can be manufactured at low cost by only the coating process. It is coming.
  • an organic thin film solar cell it is described that a composition containing a polymer compound composed of a repeating unit (A) and a repeating unit (B) and a fullerene derivative is used for an organic solar cell (Non-patent Document 1).
  • the polymer compound has a short light absorption terminal wavelength, and the range of sunlight wavelengths that can be absorbed is not sufficient. Therefore, the light absorption terminal wave of the composition containing the polymer compound has a short wavelength, and the photoelectric conversion element produced using the composition does not necessarily have sufficient conversion efficiency.
  • An object of the present invention is to provide a composition having a long light absorption terminal wavelength.
  • the present invention firstly includes a first compound having a structural unit represented by the formula (1) and a second compound comprising only a structural unit different from the structural unit represented by the formula (1)
  • a composition comprising [Wherein, Q 1 and Q 2 are the same or different and each represents -S-, -O-, -Se- or -N (R 3 )-, and R 1 , R 2 and R 3 are the same or Differently, hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group , Acid imide group, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heterocyclic
  • the present invention provides a thin film containing the composition.
  • the present invention provides an ink comprising the composition and a solvent.
  • the present invention provides an electronic device including the composition or the thin film.
  • composition of the present invention is extremely useful because it contains a compound having a light absorption terminal wavelength of a long wavelength.
  • composition of the present invention comprises a first compound having a structural unit represented by formula (1) and a second compound comprising only a structural unit different from the structural unit represented by formula (1). It is characterized by.
  • the structural unit represented by the formula (1) is a divalent group.
  • Q 1 and Q 2 are the same or different and each represents -S-, -O-, -Se- or -N (R 3 )-, and R 1 , R 2 and R 3 are the same or Differently, hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group , Acid imide group, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heterocyclic oxy group, heterocyclic thio group, arylalkenyl group, aryl An alkynyl group, a carboxyl group or a cyano group is represented. ]
  • the alkyl group may be linear or branched, and may be a cycloalkyl group.
  • the alkyl group usually has 1 to 30 carbon atoms.
  • Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl tomb, n-pentyl group, isopentyl group, 2- Methylbutyl group, 1-methylbutyl group, n-hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, 3, 7-dimethyloctyl group, nonyl group, decyl group, undecyl group, dodecy
  • Alkyl group may be linear or branched, and may be a cycloalkyloxy group.
  • the alkyloxy group may have a substituent.
  • the alkyloxy group usually has about 1 to 20 carbon atoms.
  • Specific examples of the alkyloxy group include methoxy group, ethoxy group, propyloxy group, iso-propyloxy group, butoxy group, iso-butoxy group, tert -Butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy, tri Examples thereof include a fluoromethoxy group, a pentafluoroethoxy group, a perfluorobutoxy group, a perfluorohexyl group, a perfluorooctyl group
  • the alkylthio group may be linear or branched, and may be a cycloalkylthio group.
  • the alkylthio group may have a substituent.
  • the alkylthio group usually has about 1 to 20 carbon atoms.
  • Specific examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an iso-propylthio group, a butylthio group, an iso-butylthio group, a tert-butylthio group, Examples include a pentylthio group, a hexylthio group, a cyclohexylthio group, a heptylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, a 3,7-dimethylocty
  • the aryl group usually has about 6 to 60 carbon atoms and may have a substituent.
  • Specific examples of the aryl group include a phenyl group, a C1 to C12 alkyloxyphenyl group (C1 to C12 alkyl represents an alkyl having 1 to 12 carbon atoms.
  • C1 to C12 alkyl is preferably C1 to C8 alkyl. More preferably, it is C1 to C6 alkyl, C1 to C8 alkyl represents alkyl having 1 to 8 carbon atoms, and C1 to C6 alkyl represents alkyl having 1 to 6 carbon atoms.
  • C1 to C12 alkyl, C1 to C8 alkyl and C1 to C6 alkyl include those described and exemplified for the above alkyl group, and the same applies to the following.), C1 to C12 alkylphenyl group, 1 -Naphthyl group, 2-naphthyl group, pentafluorophenyl group.
  • the aryloxy group usually has about 6 to 60 carbon atoms and may have a substituent on the aromatic ring.
  • Specific examples of the aryloxy group include a phenoxy group, a C1-C12 alkyloxyphenoxy group, a C1-C12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a pentafluorophenyloxy group.
  • the arylthio group usually has about 6 to 60 carbon atoms and may have a substituent on the aromatic ring.
  • Specific examples of the arylthio group include a phenylthio group, a C1-C12 alkyloxyphenylthio group, a C1-C12 alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a pentafluorophenylthio group.
  • the arylalkyl group usually has about 7 to 60 carbon atoms and may have a substituent.
  • Specific examples of the arylalkyl group include phenyl-C1-C12 alkyl group, C1-C12 alkyloxyphenyl-C1-C12 alkyl group, C1-C12 alkylphenyl-C1-C12 alkyl group, 1-naphthyl-C1-C12 alkyl And a 2-naphthyl-C1-C12 alkyl group.
  • the arylalkyloxy group usually has about 7 to 60 carbon atoms and may have a substituent.
  • Specific examples of the arylalkyloxy group include phenyl-C1-C12 alkyloxy group, C1-C12 alkyloxyphenyl-C1-C12 alkyloxy group, C1-C12 alkylphenyl-C1-C12 alkyloxy group, 1-naphthyl- Examples thereof include C1-C12 alkyloxy group and 2-naphthyl-C1-C12 alkyloxy group.
  • the arylalkylthio group usually has about 7 to 60 carbon atoms and may have a substituent.
  • Specific examples of the arylalkylthio group include a phenyl-C1-C12 alkylthio group, a C1-C12 alkyloxyphenyl-C1-C12 alkylthio group, a C1-C12 alkylphenyl-C1-C12 alkylthio group, and a 1-naphthyl-C1-C12 alkylthio group. And a 2-naphthyl-C1-C12 alkylthio group.
  • Acyl groups usually have about 2 to 20 carbon atoms.
  • Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a benzoyl group, a trifluoroacetyl group, and a pentafluorobenzoyl group.
  • Acyloxy groups usually have about 2 to 20 carbon atoms.
  • Specific examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
  • the amide group usually has about 2 to 20 carbon atoms.
  • An amide group refers to a group obtained by removing a hydrogen atom bonded to a nitrogen atom from an amide.
  • Specific examples of the amide group include a formamide group, an acetamide group, a propioamide group, a butyroamide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, a diformamide group, a diacetamide group, a dipropioamide group, a dibutyroamide group, and a dibenzamide group. , Ditrifluoroacetamide group and dipentafluorobenzamide group.
  • the acid imide group refers to a group obtained by removing a hydrogen atom bonded to a nitrogen atom from an acid imide.
  • Specific examples of the acid imide group include a succinimide group and a phthalimide group.
  • the substituted amino group usually has about 1 to 40 carbon atoms.
  • substituent amino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, dipropylamino group, isopropylamino group, diisopropylamino group, butylamino group, isobutylamino group, tert-Butylamino, pentylamino, hexylamino, cyclohexylamino, heptylamino, octylamino, 2-ethylhexylamino, nonylamino, decylamino, 3,7-dimethyloctylamino, laurylamino , Cyclopentylamino group, dicyclopentylamino group, cyclohexylamino group, dicyclohexylamino group, pyrrolidyl group
  • substituted silyl group examples include trimethylsilyl group, triethylsilyl group, tri-n-propylsilyl group, tri-iso-propylsilyl group, tert-butyldimethylsilyl group, triphenylsilyl group, and tri-p-xylylsilyl group.
  • substituted silyloxy group examples include trimethylsilyloxy group, triethylsilyloxy group, tri-n-propylsilyloxy group, tri-iso-propylsilyloxy group, tert-butyldimethylsilyloxy group, triphenylsilyloxy group, Examples thereof include a tri-p-xylylsilyloxy group, a tribenzylsilyloxy group, a diphenylmethylsilyloxy group, a tert-butyldiphenylsilyloxy group, and a dimethylphenylsilyloxy group.
  • substituted silylthio group examples include trimethylsilylthio group, triethylsilylthio group, tri-n-propylsilylthio group, tri-iso-propylsilylthio group, tert-butyldimethylsilylthio group, triphenylsilylthio group, Examples thereof include a tri-p-xylylsilylthio group, a tribenzylsilylthio group, a diphenylmethylsilylthio group, a tert-butyldiphenylsilylthio group, and a dimethylphenylsilylthio group.
  • substituted silylamino group examples include trimethylsilylamino group, triethylsilylamino group, tri-n-propylsilylamino group, tri-iso-propylsilylamino group, tert-butyldimethylsilylamino group, triphenylsilylamino group, Tri-p-xylylsilylamino group, tribenzylsilylamino group, diphenylmethylsilylamino group, tert-butyldiphenylsilylamino group, dimethylphenylsilylamino group, di (trimethylsilyl) amino group, di (triethylsilyl) amino group Di (tri-n-propylsilyl) amino group, di (tri-iso-propylsilyl) amino group, di (tert-butyldimethylsilyl) amino group, di (triphenylsilyl) amino group, di (tri-p -X
  • the monovalent heterocyclic group examples include furan, thiophene, pyrrole, pyrroline, pyrrolidine, oxazole, isoxazole, thiazole, isothiazole, imidazole, imidazoline, imidazolidine, pyrazole, pyrazoline, prazolidine, furazane, triazole, thiadiazole Oxadiazole, tetrazole, pyran, pyridine, piperidine, thiopyran, pyridazine, pyrimidine, pyrazine, piperazine, morpholine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, isoindoline, chromene, Chroman, isochroman, benzopyran, quinoline, isoquinoline, quinolidine, benzimidazole, be
  • heterocyclic oxy group and the heterocyclic thio group include a group in which an oxygen atom or a sulfur atom is bonded to the monovalent heterocyclic group.
  • the heterocyclic oxy group usually has about 4 to 60 carbon atoms.
  • Specific examples of the heterocyclic oxy group include thienyloxy group, C1-C12 alkylthienyloxy group, pyrrolyloxy group, furyloxy group, pyridyloxy group, C1-C12 alkylpyridyloxy group, imidazolyloxy group, pyrazolyloxy group, triazolyl group.
  • the heterocyclic thio group usually has about 4 to 60 carbon atoms.
  • Specific examples of the heterocyclic thio group include thienyl mercapto group, C1-C12 alkyl thienyl mercapto group, pyrrolyl mercapto group, furyl mercapto group, pyridyl mercapto group, C1-C12 alkyl pyridyl mercapto group, imidazolyl mercapto group, pyrazolyl mercapto group. , Triazolyl mercapto group, oxazolyl mercapto group, thiazole mercapto group and thiadiazole mercapto group.
  • the arylalkenyl group usually has 7 to 20 carbon atoms, and specific examples of the arylalkenyl group include a styryl group.
  • the arylalkynyl group usually has 7 to 20 carbon atoms, and specific examples of the arylalkynyl group include a phenylacetylenyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • At least one of R 1 and R 2 is preferably an alkyl group.
  • Q 1 and Q 2 are preferably —S— and —O— from the viewpoint of making the light absorption edge wavelength of the composition of the present invention long wavelength absorption.
  • at least one of Q 1 and Q 2 is preferably —S—.
  • Examples of the structural unit represented by Formula (1) include structural units represented by Formula 301 to Formula 351.
  • the structural units represented by Formula 301 to Formula 351 are divalent groups.
  • R 10 represents an alkyl group, an aryl group, an arylalkyl group, or a monovalent heterocyclic group.
  • Definition of alkyl group, aryl group, arylalkyl group, monovalent heterocyclic group specific examples include definition of alkyl group, aryl group, arylalkyl group, monovalent heterocyclic group represented by R 1 described above The same as the specific example.
  • R 10 is preferably an alkyl group.
  • X 10 represents a halogen atom. Specific examples of the halogen atom are the same as the specific examples of the halogen atom represented by R 1 described above.
  • R 3 represents the same meaning as described above.
  • the structural units represented by Formula 301 to Formula 351 are preferable, the structural units represented by Formula 301 to Formula 306 are more preferable, and the structural unit is particularly preferable.
  • the first compound may have a structural unit other than the structural unit represented by the formula (1).
  • the structural unit represented by Formula (1) and a structural unit different from the structural unit represented by Formula (1) are: It is preferable to form a conjugate. Conjugation in the present invention is chained in the order of unsaturated bond-single bond-unsaturated bond, two ⁇ bonds of ⁇ orbitals are adjacent to each other, and each ⁇ electron is arranged in parallel. It refers to a state in which ⁇ electrons are not localized on the bond but are spread and delocalized on the adjacent single bond.
  • the unsaturated bond refers to a double bond or a triple bond.
  • the structural unit different from the structural unit represented by the formula (1) includes a divalent group, and examples of the divalent group include an arylene group and a divalent heterocyclic group.
  • the structural unit different from the structural unit represented by the formula (1) is an arylene group or a divalent aromatic heterocyclic group.
  • the arylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and the number of carbon atoms constituting the ring is usually about 6 to 60, preferably 6 to 20.
  • aromatic hydrocarbons include those having a benzene ring, those having a condensed ring, those having two or more independent benzene rings or condensed rings directly bonded, or bonded via a group such as vinylene. It is.
  • arylene group examples include a phenylene group (for example, formulas 1 to 3 in the figure below), a naphthalenediyl group (formulas 4 to 13 in the figure below), an anthracenediyl group (formulas 14 to 19 in the figure below), and a biphenyl-diyl group (formula in the figure below). 20-25), a terphenyl-diyl group (formulas 26 to 28 in the following figure), a condensed ring compound group (formulas 29 to 38 in the following figure) and the like.
  • the fused ring compound group includes a fluorene-diyl group (formulas 36 to 38 in the following figure).
  • the divalent heterocyclic group means an atomic group remaining after removing two hydrogen atoms from a heterocyclic compound, and the number of carbon atoms constituting the ring is usually about 3 to 60.
  • the heterocyclic compound is an organic compound having a cyclic structure, and the elements constituting the ring include not only carbon atoms but also hetero atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, and arsenic in the ring. Say things.
  • divalent heterocyclic group examples include the following. Divalent heterocyclic group containing nitrogen as a hetero atom: pyridine-diyl group (formulas 39 to 44 in the following figure), diazaphenylene group (formulas 45 to 48 in the figure below), quinoline diyl group (formulas 49 to 63 in the figure below) A quinoxaline diyl group (formulas 64-68 in the following figure), an acridine diyl group (formulas 69-72 in the figure below), a bipyridyldiyl group (formulas 73-75 in the figure below), a phenanthroline diyl group (formulas 76-78 in the figure below); Groups having a fluorene structure containing silicon, nitrogen, sulfur, selenium and the like as a hetero atom (formulas 79 to 93 in the following figure); 5-membered heterocyclic groups containing silicon, nitrogen, sulfur, selenium, etc.
  • heteroatoms formulae 94-98 in the figure below
  • 5-membered condensed heterocyclic groups containing silicon, nitrogen, sulfur, selenium and the like as a hetero atom formulas 99 to 110 in the following figure
  • 5-membered heterocyclic groups containing silicon, nitrogen, sulfur, selenium, etc. as heteroatoms, which are bonded at the ⁇ -position of the heteroatoms to form dimers or oligomers (formulas 111 to 112 in the figure below);
  • R represents a hydrogen atom or a substituent.
  • a plurality of R may be the same or different, and may be bonded to each other to form a ring.
  • examples of the substituent include alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, aryl Alkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, amide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group, nitro group, And a group selected from a cyano group.
  • the hydrogen atom contained in these substituents may be substituted with a fluorine atom.
  • An alkyl group represented by R an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a substituted amino group
  • substitud silyl group, halogen atom, acyl group, acyloxy group, amide group, monovalent heterocyclic group specific examples are the alkyl group, alkyloxy group, alkylthio group, aryl group represented by R 1 described above, Aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, substituted amino group, substituted silyl group, halogen atom, acyl group, acyl
  • substituted carboxyl group those having 2 to 20 carbon atoms are usually used, and examples thereof include a group having a methyl ester structure, a group having an ethyl ester structure, and a group having a butyl ester structure.
  • a and b are the same or different and represent the number of repetitions, and are usually 1 to 5, preferably 1 to 3, and particularly preferably 1.
  • the first compound contained in the composition of the present invention may be a polymer compound.
  • the polymer compound in the present invention refers to a polymer having a weight average molecular weight (Mw) of 1000 or more, and a polymer compound having a weight average molecular weight of 3,000 to 10,000,000 is preferably used. If the weight average molecular weight is lower than 3000, defects may occur in film formation during device fabrication, and if it exceeds 10000000, solubility in a solvent and applicability during device fabrication may be degraded.
  • the weight average molecular weight is more preferably 8000 to 5000000, and particularly preferably 10,000 to 1000000.
  • the weight average molecular weight in this invention points out the weight average molecular weight of polystyrene conversion calculated using the standard sample of polystyrene using gel permeation chromatography (GPC).
  • the content of the structural unit represented by the formula (1) in the polymer compound may be at least one in the compound.
  • the polymer compound contains an average of 2 or more per polymer chain, more preferably an average of 3 or more per polymer chain.
  • the polymer compound of the present invention preferably has a solubility capable of producing a solution containing 0.01% by weight (wt)% or more of the polymer compound, and a solution containing 0.1% by weight or more is produced. It is more preferable that it has the solubility which can be made, and it is further more preferable that it has the solubility which can produce the solution containing 0.4 wt% or more.
  • composition of the present invention contains a second compound consisting only of a structural unit different from the structural unit represented by the formula (1).
  • the second compound include an electron accepting compound and an electron donating compound.
  • Electron-accepting compounds include carbon materials such as titanium oxide and carbon nanotubes, fullerenes, fullerene derivatives, metal oxides, oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinones and derivatives thereof, naphthoquinones and derivatives thereof, anthraquinones And its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, poly Fluorene and its derivatives, phenanthrene derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (basocuproin) and the like, preferably oxidation Tan, carbon nanotube, fullerene, a fullerene derivative, particularly preferably a
  • the work function of the electron-accepting compound is preferably 3.0 eV or more, and more preferably 3.2 eV or more.
  • the work function indicates the absolute value of the lowest unoccupied molecular orbital (LUMO) when the vacuum level is 0 eV.
  • Examples of the electron donating compound include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, oligothiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, and aromatic amines in side chains or main chains. And polysiloxane derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, polythienylene vinylene and derivatives thereof, and the like.
  • the electron-accepting compound and the electron-donating compound are relatively determined from the energy levels of these compounds.
  • the second compound is preferably an electron accepting compound.
  • the content of the first compound in the composition of the present invention is not particularly limited and is appropriately selected depending on the purpose in the range of more than 0% by weight and less than 100% by weight, preferably 5% by weight. It is ⁇ 95 wt%, more preferably 10 wt% to 75 wt%, and particularly preferably 20 wt% to 50 wt%.
  • the ink of the present invention contains the composition and a solvent.
  • the solvent include an aromatic hydrocarbon solvent, a halogen-substituted aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, a halogen-substituted aliphatic hydrocarbon solvent, an ether solvent, and a cyclic ether solvent from the viewpoint of solubility.
  • aromatic hydrocarbon solvents and halogen-substituted aliphatic hydrocarbon solvents and more preferred are halogen-substituted aromatic hydrocarbon solvents.
  • halogen-substituted aromatic hydrocarbon solvent examples include chlorobenzene, dichlorobenzene, trichlorobenzene and the like, preferably dichlorobenzene, and particularly preferably orthodichlorobenzene.
  • the surface tension of the solvent at 25 ° C. is preferably larger than 25 mN / m, more preferably larger than 25 mN / m and smaller than 60 mN / m.
  • Specific examples include toluene (27.9 mN / m), benzonitrile (34.5 mN / m), 1,3-benzodioxole (28.8 mN / m), orthoxylene (29.8 mN / m), Metaxylene (28.5 mN / m), paraxylene (28.0 mN / m), cyclohexanone (34.6 mN / m), chlorobenzene (33.0 mN / m), orthodichlorobenzene (36.7 mN / m), metadi Chlorobenzene (35.4 mN / m), paradichlorobenzene (32.5 mN / m), cis-
  • Numerical values in parentheses represent surface tension at 25 ° C. The surface tension was measured according to “Lange's Handbook of Chemistry 13th edition”, John. A. Dean, McGaw-Hill, published in 1972, pp. The values described in 10 / 103-10 / 116 are shown.
  • an aromatic compound having a substituent is preferable, and chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, orthoxylene, Metaxylene, paraxylene and toluene are more preferred.
  • the content of the first compound in the ink is preferably 0.01 wt% to 99.9 wt%, more preferably 0.1 wt% to 50 wt%, expressed as a weight fraction in the ink.
  • the amount is preferably 0.3% to 30% by weight, particularly preferably 0.5% to 10% by weight.
  • the content of the second compound in the ink is not particularly limited, but the sum of the content of the first compound and the content of the first compound is less than 100% by weight based on the total weight of the composition ink, preferably 0.01 wt% to 99.9 wt%, more preferably 0.1 wt% to 50 wt%, still more preferably 0.3 wt% to 30 wt%, particularly preferably 0.5 wt% to 10 wt% It is.
  • the content of the electron-accepting compound and the content of the first compound in the ink of the present invention are (content of electron-accepting compound) / (first The content of the compound is preferably 0.1 to 10, and more preferably 0.2 to 5.
  • the polymer compound can be synthesized, for example, by using a compound represented by the formula (1-2) as one of raw materials.
  • W 1 and W 2 are the same or different and are a hydrogen atom, a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, an aryl alkyl sulfonate group, a boric acid ester residue, a sulfonium methyl group, a phosphonium methyl group, or a phosphonate. It represents a methyl group, a monohalogenated methyl group, a boric acid residue, a formyl group, a vinyl group or an organotin residue.
  • R 1 and R 2 represent the same meaning as described above.
  • the compound represented by the formula (1-2) can be produced by introducing a substituent into the compound represented by the formula (1-3) by a known Wittig reaction or the like. [Wherein W 1 and W 2 represent the same meaning as described above. ]
  • a known method can be used.
  • a known method can be used.
  • a known method can be used.
  • a Wittig reagent in the presence of a Wittig reagent, in a solvent such as aromatic hydrocarbons, ethers, halogenated hydrocarbons, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile.
  • the reaction can be carried out under cooling or heating.
  • the Wittig reagent can be obtained, for example, by reacting the corresponding phosphonium salt with a base such as alkyllithium such as potassium carbonate, tert-butoxypotassium, sodium hydride or n-butyllithium.
  • a polymer compound that can be used in the present invention can be produced.
  • the method for producing a polymer compound that can be used in the present invention is not particularly limited, but a method using a Suzuki coupling reaction or a Stille coupling reaction is preferable from the viewpoint of ease of synthesis of the polymer compound. .
  • E 2 represents a structural unit containing a group represented by the formula (1).
  • T 1 and T 2 are the same or different and each represents a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, or an arylalkyl sulfonate group.
  • E 1 is preferably a divalent aromatic group, and more preferably 1 to 141 described above.
  • the total number of moles of one or more compounds represented by formula (200) used in the reaction is excessive with respect to the total number of moles of one or more compounds represented by formula (100). Is preferred.
  • the total number of moles of one or more compounds represented by formula (200) used in the reaction is 1 mole, the total number of moles of one or more compounds represented by formula (100) is 0.6 to 0.00.
  • the amount is preferably 99 mol, more preferably 0.7 to 0.95 mol.
  • Examples of the halogen atom represented by T 1 and T 2 in Formula (200) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • a bromine atom and an iodine atom are preferable, and a bromine atom is more preferable.
  • Examples of the alkyl sulfonate group represented by T 1 and T 2 in Formula (200) include a methane sulfonate group, an ethane sulfonate group, and a trifluoromethane sulfonate group.
  • Examples of the aryl sulfonate group include a benzene sulfonate group and a p-toluene sulfonate group.
  • a benzyl sulfonate group is illustrated as an arylalkyl sulfonate group.
  • the method for carrying out the Suzuki coupling reaction includes a method in which a palladium catalyst is used as a catalyst in an arbitrary solvent and the reaction is carried out in the presence of a base.
  • Examples of the palladium catalyst used in the Suzuki coupling reaction include a Pd (0) catalyst, a Pd (II) catalyst, and the like.
  • palladium [tetrakis (triphenylphosphine)] palladium acetates, dichlorobis (Triphenylphosphine) palladium, palladium acetate, tris (dibenzylideneacetone) dipalladium, bis (dibenzylideneacetone) palladium, etc. are mentioned, but from the viewpoint of ease of reaction (polymerization) operation and reaction (polymerization) rate.
  • the addition amount of the palladium catalyst is not particularly limited as long as it is an effective amount as a catalyst, but is usually 0.0001 mol to 0.5 mol with respect to 1 mol of the compound represented by the formula (100). The amount is preferably 0.0003 mol to 0.1 mol.
  • a phosphorus compound such as triphenylphosphine, tri (o-tolyl) phosphine, tri (o-methoxyphenyl) phosphine is added as a ligand.
  • the addition amount of the ligand is usually 0.5 mol to 100 mol, preferably 0.9 mol to 20 mol, more preferably 1 mol to 10 mol, relative to 1 mol of the palladium catalyst. is there.
  • Examples of the base used for the Suzuki coupling reaction include inorganic bases, organic bases, inorganic salts and the like.
  • examples of the inorganic base include potassium carbonate, sodium carbonate, barium hydroxide and the like.
  • examples of the organic base include triethylamine and tributylamine.
  • examples of the inorganic salt include cesium fluoride.
  • the addition amount of the base is usually 0.5 mol to 100 mol, preferably 0.9 mol to 20 mol, more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by the formula (100). is there.
  • the Suzuki coupling reaction is usually performed in a solvent.
  • the solvent include N, N-dimethylformamide, toluene, dimethoxyethane, tetrahydrofuran and the like. From the viewpoint of solubility of the polymer compound used in the present invention, toluene and tetrahydrofuran are preferred.
  • the base may be added as an aqueous solution and reacted in a two-phase system.
  • an inorganic salt is used as the base, it is usually added as an aqueous solution and reacted from the viewpoint of solubility of the inorganic salt.
  • phase transfer catalysts such as a quaternary ammonium salt
  • the temperature at which the Suzuki coupling reaction is carried out depends on the solvent, but is usually about 50 to 160 ° C., and preferably 60 to 120 ° C. from the viewpoint of increasing the molecular weight of the polymer compound. Alternatively, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the reaction time may end when the target degree of polymerization is reached, but is usually about 0.1 to 200 hours. About 1 to 30 hours is efficient and preferable.
  • the Suzuki coupling reaction is performed in a reaction system in which the Pd (0) catalyst is not deactivated under an inert atmosphere such as argon gas or nitrogen gas.
  • an inert atmosphere such as argon gas or nitrogen gas.
  • it is performed in a system sufficiently deaerated with argon gas or nitrogen gas.
  • the compound represented by the formula (100), the compound represented by the formula (200), Dichlorobis (triphenylphosphine) palladium (II) was charged, the polymerization vessel was sufficiently replaced with nitrogen gas, degassed, and then degassed by adding a degassed solvent such as toluene by bubbling with nitrogen gas in advance.
  • a base degassed by bubbling with nitrogen gas in advance for example, an aqueous sodium carbonate solution
  • nitrogen gas in advance for example, an aqueous sodium carbonate solution
  • the manufacturing method which has a process with which the 1 or more types of compound represented by this, and the 1 or more types of compound represented by the said Formula (200) are made to react in presence of a palladium catalyst is mentioned.
  • Examples of the organic tin residue include —SnR 100 3 and the like.
  • R 100 include an alkyl group and an aryl group.
  • Alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, 1 -Methylbutyl group, n-hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, decyl group, Examples thereof include chain alkyl groups such as undecyl group, dodecyl group, tetradecyl group, hexadecyl tomb,
  • aryl group examples include a phenyl group and a naphthyl group.
  • -SnMe 3 as organotin residue, -SnEt 3, -SnBu 3, an -SnPh 3, more preferably -SnMe 3, -SnEt 3, is -SnBu 3.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • Examples of the halogen atom represented by T 1 and T 2 in Formula (200) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In view of ease of synthesis of the polymer compound, a bromine atom and an iodine atom are preferable.
  • Examples of the alkyl sulfonate group represented by T 1 and T 2 in Formula (200) include a methane sulfonate group, an ethane sulfonate group, and a trifluoromethane sulfonate group.
  • Examples of the aryl sulfonate group include a benzene sulfonate group and a p-toluene sulfonate group.
  • a benzyl sulfonate group is illustrated as an aryl sulfonate group.
  • examples of the catalyst include a method of reacting in an arbitrary solvent under a palladium catalyst.
  • examples of the palladium catalyst used in the Stille coupling reaction include Pd (0) catalyst, Pd (II) catalyst, and the like.
  • palladium [tetrakis (triphenylphosphine)] palladium acetates, dichlorobis (Triphenylphosphine) palladium, palladium acetate, tris (dibenzylideneacetone) dipalladium, bis (dibenzylideneacetone) palladium
  • palladium [Tetrakis (triphenylphosphine)] and tris (dibenzylideneacetone) dipalladium are preferred.
  • the addition amount of the palladium catalyst used for the Stille coupling reaction is not particularly limited as long as it is an effective amount as a catalyst, but is usually 0.0001 per 1 mol of the compound represented by the formula (100). Mol to 0.5 mol, preferably 0.0003 to 0.2 mol.
  • a ligand and a co-catalyst can also be used as needed.
  • the ligand include phosphorus compounds such as triphenylphosphine, tri (o-tolyl) phosphine, tri (o-methoxyphenyl) phosphine, tris (2-furyl) phosphine, triphenylarsine, and triphenoxyarsine.
  • Examples include arsenic compounds.
  • the cocatalyst include copper iodide, copper bromide, copper chloride, and copper (I) 2-thenoylate.
  • the amount of the ligand or cocatalyst added is usually 0.5 mol to 100 mol, preferably 0.9 mol to 20 mol, relative to 1 mol of the palladium catalyst. More preferably, it is 1 mol to 10 mol.
  • the Stille coupling reaction is usually performed in a solvent.
  • the solvent include N, N-dimethylformamide, N, N-dimethylacetamide, toluene, dimethoxyethane, tetrahydrofuran and the like. From the viewpoint of solubility of the polymer compound used in the present invention, toluene, tetrahydrofuran is preferred.
  • the temperature at which the Stille coupling reaction is carried out depends on the solvent, but is usually about 50 to 160 ° C., and preferably 60 to 120 ° C. from the viewpoint of increasing the molecular weight of the polymer compound. Alternatively, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the time for carrying out the reaction may be the end point when the desired degree of polymerization is reached, but is usually about 0.1 to 200 hours. About 1 to 30 hours is efficient and preferable.
  • the Stille coupling reaction is performed in a reaction system in which the Pd catalyst is not deactivated under an inert atmosphere such as argon gas or nitrogen gas.
  • an inert atmosphere such as argon gas or nitrogen gas.
  • the polymerization vessel is charged with a compound represented by the formula (300), a compound represented by the formula (200), A palladium catalyst is charged, and the polymerization vessel is sufficiently replaced with nitrogen gas, degassed, and then bubbled with nitrogen gas in advance to add a degassed solvent, for example, toluene, and then coordinate as necessary.
  • the mixture is heated and heated, for example, and polymerized while maintaining an inert atmosphere at the reflux temperature for 8 hours.
  • the number average molecular weight (Mn) in terms of polystyrene of the polymer compound is preferably 1 ⁇ 10 3 to 1 ⁇ 10 8 .
  • Mn number average molecular weight in terms of polystyrene
  • a tough thin film is easily obtained.
  • it is 10 8 or less the solubility is high and the production of the thin film is easy.
  • the terminal group of the polymer compound is protected with a stable group, because if the polymerization active group remains as it is, there is a possibility that the characteristics and life of the element obtained when used for the preparation of the element may be reduced. It may be.
  • Those having a conjugated bond continuous with the conjugated structure of the main chain are preferable, and for example, a structure bonded to an aryl group or a heterocyclic group via a vinylene group may be used.
  • the light absorption terminal wavelength is preferably a long wavelength.
  • the light absorption terminal wavelength can be determined by the following method.
  • a spectrophotometer for example, JASCO-V670, UV-visible near infrared spectrophotometer manufactured by JASCO Corporation
  • the measurable wavelength range is 200 to 1500 nm. Therefore, measurement is performed in this wavelength range.
  • the absorption spectrum of the substrate used for measurement is measured.
  • a quartz substrate, a glass substrate, or the like is used.
  • a thin film containing the first compound is formed on the substrate from a solution containing the first compound or a melt containing the first compound.
  • film formation from a solution drying is performed after film formation.
  • an absorption spectrum of the laminate of the thin film and the substrate is obtained.
  • the difference between the absorption spectrum of the laminate of the thin film and the substrate and the absorption spectrum of the substrate is obtained as the absorption spectrum of the thin film.
  • the vertical axis represents the absorbance of the first compound
  • the horizontal axis represents the wavelength. It is desirable to adjust the thickness of the thin film so that the absorbance at the largest absorption peak is about 0.5 to 2.
  • the absorbance of the absorption peak with the longest wavelength among the absorption peaks is defined as 100%, and the intersection of the absorption peak and a straight line parallel to the horizontal axis (wavelength axis) including the absorbance of 50% of the absorption peak.
  • the intersection point that is longer than the peak wavelength is taken as the first point.
  • the intersection point between the absorption peak and a straight line parallel to the wavelength axis containing 25% of the absorbance, which is longer than the peak wavelength of the absorption peak, is defined as a second point.
  • the intersection of the straight line connecting the first point and the second point and the reference line is defined as the light absorption terminal wavelength.
  • the reference line is the intersection of the absorption peak and the straight line parallel to the wavelength axis including the absorbance of 10% at the absorption peak of the longest wavelength, where the absorbance of the absorption peak is 100%.
  • the third point on the absorption spectrum that is 100 nm longer than the reference wavelength and the absorption spectrum that is 150 nm longer than the reference wavelength with reference to the wavelength of the intersection that is longer than the peak wavelength of the absorption peak A straight line connecting the top and the fourth point.
  • the composition of the present invention can exhibit a high electron and / or hole transport property, when an organic thin film containing the composition is used in a device, it can be absorbed by electrons or holes injected from an electrode or light absorption. The generated charge can be transported. Taking advantage of these characteristics, it can be suitably used for various devices such as a photoelectric conversion device, an organic thin film transistor, and an organic electroluminescence device. Hereinafter, these elements will be described individually.
  • the photoelectric conversion element having the composition of the present invention has one or more active layers containing the composition of the present invention between a pair of electrodes, at least one of which is transparent or translucent.
  • a preferable embodiment of the photoelectric conversion element having the composition of the present invention is formed from an organic composition of a pair of electrodes, at least one of which is transparent or translucent, and a p-type organic semiconductor and an n-type organic semiconductor. Has an active layer.
  • the composition of the present invention is preferably used as an active layer. The operation mechanism of the photoelectric conversion element of this embodiment will be described.
  • the photoelectric conversion element manufactured using the composition of the present invention is usually formed on a substrate.
  • the substrate may be any substrate that does not chemically change when the electrodes are formed and the organic layer is formed.
  • the material for the substrate include glass, plastic, polymer film, and silicon.
  • the opposite electrode that is, the electrode far from the substrate
  • the transparent or translucent electrode material examples include a conductive metal oxide film and a translucent metal thin film. Specifically, a film formed using a conductive material made of indium oxide, zinc oxide, tin oxide, and indium tin oxide (ITO), indium zinc oxide, etc., which is a composite thereof, NESA Gold, platinum, silver, copper and the like are used, and ITO, indium / zinc / oxide, and tin oxide are preferable.
  • the method for producing the electrode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like.
  • One electrode may not be transparent, and as the electrode material of the electrode, a metal, a conductive polymer, or the like can be used.
  • the electrode material include metals such as lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like.
  • one or more alloys selected from the group consisting of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, and tin.
  • Examples include alloys with metals, graphite, graphite intercalation compounds, polyaniline and derivatives thereof, and polythiophene and derivatives thereof.
  • Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
  • An additional intermediate layer other than the active layer may be used as a means for improving the photoelectric conversion efficiency.
  • the material used for the intermediate layer include alkali metals such as lithium fluoride, halides of alkaline earth metals, oxides such as titanium oxide, and PEDOT (poly-3,4-ethylenedioxythiophene).
  • the said active layer may contain the composition of this invention individually by 1 type, or may contain 2 or more types in combination. Moreover, in order to improve the hole transport property of the said active layer, compounds other than the composition of this invention can also be mixed and used as an electron-donating compound and / or an electron-accepting compound in the said active layer.
  • the thickness of the active layer is usually preferably 1 nm to 100 ⁇ m, more preferably 2 nm to 1000 nm, still more preferably 5 nm to 500 nm, more preferably 20 nm to 200 nm.
  • the method for producing the active layer may be produced by any method, and examples thereof include film formation from a solution containing a polymer compound and film formation by vacuum deposition.
  • a preferred method for producing a photoelectric conversion element is a method for producing an element having a first electrode and a second electrode, and having an active layer between the first electrode and the second electrode, A step of forming an active layer by applying the composition ink of the present invention containing the composition of the present invention and a solvent on the first electrode by a coating method, and forming a second electrode on the active layer It is the manufacturing method of the element which has a process.
  • slit coating method, knife coating method, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip Coating methods such as coating methods, spray coating methods, screen printing methods, gravure printing methods, flexographic printing methods, offset printing methods, inkjet coating methods, dispenser printing methods, nozzle coating methods, capillary coating methods, etc.
  • a method, a capillary coating method, a gravure coating method, a micro gravure coating method, a bar coating method, a knife coating method, a nozzle coating method, an ink jet coating method, and a spin coating method are preferable.
  • the composition of the present invention can also be used for organic thin film transistors.
  • the organic thin film transistor has a configuration including a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between these electrodes, and a gate electrode for controlling the amount of current passing through the current path.
  • the organic semiconductor layer is constituted by the organic thin film described above. Examples of such an organic thin film transistor, field effect, electrostatic induction type, and the like.
  • a field effect organic thin film transistor includes a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, a gate electrode for controlling the amount of current passing through the current path, and an organic semiconductor layer and a gate electrode It is preferable to provide an insulating layer disposed between the two.
  • the source electrode and the drain electrode are preferably provided in contact with the organic semiconductor layer (active layer), and the gate electrode is preferably provided with an insulating layer in contact with the organic semiconductor layer interposed therebetween.
  • the organic semiconductor layer is constituted by an organic thin film containing the composition of the present invention.
  • the electrostatic induction type organic thin film transistor has a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, and a gate electrode for controlling the amount of current passing through the current path. It is preferable to be provided in the organic semiconductor layer.
  • the source electrode and the drain electrode are preferably provided in contact with the organic semiconductor layer.
  • the structure of the gate electrode may be a structure in which a current path flowing from the source electrode to the drain electrode is formed and the amount of current flowing through the current path can be controlled by a voltage applied to the gate electrode. An electrode is mentioned.
  • the organic semiconductor layer is constituted by an organic thin film containing the composition of the present invention.
  • the photoelectric conversion element using the composition of the present invention can be operated as an organic thin film solar cell by generating photovoltaic power between the electrodes by irradiating light such as sunlight from a transparent or translucent electrode. it can. It can also be used as an organic thin film solar cell module by integrating a plurality of organic thin film solar cells.
  • the organic light sensor can be operated. It can also be used as an organic image sensor by integrating a plurality of organic photosensors.
  • the above-mentioned organic thin film transistor can be used as a pixel driving element used for controlling the uniformity of screen brightness and the screen rewriting speed of an electrophoretic display, a liquid crystal display, an organic electroluminescence display, and the like.
  • the organic thin film solar cell can basically have the same module structure as a conventional solar cell module.
  • the solar cell module generally has a structure in which cells are formed on a support substrate such as metal or ceramic, and the cell is covered with a filling resin or protective glass, and light is taken in from the opposite side of the support substrate. It is also possible to use a transparent material such as tempered glass for the support substrate, configure a cell thereon, and take in light from the transparent support substrate side.
  • a module structure called a super straight type, a substrate type, and a potting type, a substrate integrated module structure used in an amorphous silicon solar cell, and the like are known.
  • the organic thin-film solar cell produced using the polymer of the present invention can also be appropriately selected from these module structures depending on the purpose of use, the place of use and the environment.
  • a typical super straight type or substrate type module cells are arranged at regular intervals between support substrates that are transparent on one or both sides and subjected to antireflection treatment, and adjacent cells are connected by metal leads or flexible wiring.
  • the current collector electrode is connected to the outer edge portion, and the generated power is taken out to the outside.
  • plastic materials such as ethylene vinyl acetate (EVA) may be used between the substrate and the cell in the form of a film or a filling resin depending on the purpose in order to protect the cell and improve the current collection efficiency.
  • EVA ethylene vinyl acetate
  • the surface protection layer is made of a transparent plastic film, or the protective function is achieved by curing the filling resin. It is possible to eliminate the supporting substrate on one side.
  • the periphery of the support substrate is fixed in a sandwich shape with a metal frame in order to ensure internal sealing and module rigidity, and the support substrate and the frame are hermetically sealed with a sealing material.
  • a flexible material is used for the cell itself, the support substrate, the filling material, and the sealing material, a solar cell can be formed on the curved surface.
  • a solar cell using a flexible support such as a polymer film
  • cells are sequentially formed while feeding out a roll-shaped support, cut to a desired size, and then the periphery is sealed with a flexible and moisture-proof material.
  • the battery body can be produced.
  • a module structure called “SCAF” described in Solar Energy Materials and Solar Cells, 48, p383-391 may be used.
  • a solar cell using a flexible support can be used by being bonded and fixed to a curved glass or the like.
  • the composition of the present invention can also be used for an organic electroluminescence device (organic EL device).
  • the organic EL element has a light-emitting layer between a pair of electrodes at least one of which is transparent or translucent.
  • the organic EL element may include a hole transport layer and an electron transport layer in addition to the light emitting layer.
  • the composition of the present invention is contained in any one of the light emitting layer, the hole transport layer, and the electron transport layer.
  • the light emitting layer may contain a charge transport material (which means a generic term for an electron transport material and a hole transport material).
  • an organic EL element an element having an anode, a light emitting layer, and a cathode, and an anode, a light emitting layer, and an electron having an electron transport layer containing an electron transport material adjacent to the light emitting layer between the cathode and the light emitting layer.
  • an element having an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode an element having an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.
  • NMR measurement The NMR measurement was performed by dissolving the compound in deuterated chloroform and using an NMR apparatus (Varian, INOVA300).
  • the number average molecular weight and the weight average molecular weight in terms of polystyrene were determined by gel permeation chromatography (GPC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp).
  • GPC gel permeation chromatography
  • the polymer compound to be measured was dissolved in tetrahydrofuran to a concentration of about 0.5% by weight, and 30 ⁇ L was injected into GPC. Tetrahydrofuran was used as the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
  • TSKgel SuperHM-H manufactured by Tosoh
  • TSKgel SuperH2000 manufactured by Tosoh
  • a differential refractive index detector manufactured by Shimadzu Corporation, trade name: RID-10A was used as the detector.
  • reaction solution was cooled to ⁇ 25 ° C., and a solution in which 60 g (236 mmol) of iodine was dissolved in 1000 mL of diethyl ether was added dropwise over 30 minutes. After dropping, the mixture was stirred at room temperature (25 ° C.) for 2 hours, and 50 mL of 1N aqueous sodium thiosulfate solution was added to stop the reaction. After extracting the reaction product with diethyl ether, the reaction product was dried with magnesium sulfate, filtered, and the filtrate was concentrated to obtain 35 g of a crude product. The crude product was purified by recrystallization using chloroform to obtain 28 g of Compound 1.
  • the organic layer as a chloroform solution was dried over magnesium sulfate, the organic layer was filtered, and the filtrate was concentrated to obtain a crude product.
  • the composition was purified with a silica gel column (developing solution: chloroform) to obtain 3.26 g of compound 3.
  • the organic layer was washed twice with 20 ml of water, twice with 20 mL of an acetic acid aqueous solution (3 wt%) and further twice with 20 mL of water, and poured into methanol to precipitate a polymer.
  • the polymer was filtered and dried, and the resulting polymer was dissolved again in 5 mL of toluene and passed through an alumina / silica gel column.
  • the obtained solution was poured into methanol to precipitate a polymer, and the polymer was filtered and then dried to obtain 102 mg of a purified polymer.
  • this polymer is referred to as polymer A.
  • C60PCBM phenyl C61-butyric acid methyl ester
  • weight ratio of polymer A / C60PCBM 1/3
  • the ink 1 was applied onto a substrate by spin coating to produce an organic film containing the polymer B (film thickness of about 100 nm).
  • the thus prepared organic film had a light absorption terminal wavelength of 865 nm.
  • lithium fluoride was vapor-deposited with a thickness of 2 nm on the organic film by a vacuum vapor deposition machine, and then Al was vapor-deposited with a thickness of 100 nm.
  • the shape of the obtained organic thin film solar cell was a regular square of 2 mm ⁇ 2 mm.
  • the obtained organic thin film solar cell is irradiated with a certain amount of light using a solar simulator (trade name OTENTO-SUNII: AM1.5G filter, irradiance 100 mW / cm 2 , manufactured by Spectrometer Co., Ltd.), and the generated current and voltage are measured.
  • Example 1 Production, evaluation of ink and organic thin film solar cell
  • a composition, an ink, and an organic thin film solar cell were manufactured in the same manner except that the polymer B was used instead of the polymer A.
  • the light absorption terminal wavelength is 545 nm
  • Jsc (short circuit current density) 0.07 mA / cm 2
  • Voc (open-circuit voltage) 0.80 V
  • ff (fill factor (curve factor)) 0.43
  • photoelectric conversion efficiency ( ⁇ ) was 0.03%.
  • silica gel of the silica gel column silica gel previously immersed in hexane containing 5 wt% triethylamine for 5 minutes and then rinsed with hexane was used. After purification, 1.14 g (1.20 mmol) of Compound 8 was obtained.
  • the precipitated polymer was collected by filtration, and the obtained polymer was put into a cylindrical filter paper and extracted with methanol, acetone and hexane for 5 hours each using a Soxhlet extractor.
  • the polymer remaining in the cylindrical filter paper was dissolved in 100 mL of o-dichlorobenzene, 2 g of sodium diethyldithiocarbamate and 50 mL of water were added, and the mixture was stirred under reflux for 8 hours.
  • the organic layer is washed twice with 50 ml of water, then twice with 50 mL of a 3 wt% aqueous acetic acid solution, then twice with 50 mL of water, and then 50 mL of 5% aqueous potassium fluoride solution. And then washed twice with 50 mL of water, and the resulting solution was poured into methanol to precipitate a polymer. The polymer was filtered and dried, and the obtained polymer was redissolved in 50 mL of o-dichlorobenzene and passed through an alumina / silica gel column.
  • Example 2 (Production, evaluation of ink and organic thin film solar cell)
  • a composition, an ink, and an organic thin film solar cell were produced in the same manner except that the polymer C was used instead of the polymer A.
  • the light absorption terminal wavelength is 865 nm
  • Jsc (short circuit current density) 3.52 mA / cm 2
  • Voc (open end voltage) 0.59 V
  • ff (fill factor (curve factor)) 0.48
  • photoelectric conversion efficiency ( ⁇ ) was 1.00%.

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Abstract

La présente invention concerne une composition ayant une longue longueur d'onde de fin d'absorption de lumière. Plus spécifiquement, l'invention concerne une composition contenant un premier composé ayant une unité structurelle représentée par la formule (1) et un second composé comprenant uniquement une unité structurelle différente de l'unité structurelle représentée par la formule (1). Dans la formule (1), Q1 et Q2 représentent chacun indépendamment l'un de l'autre -S-, -O-, -Se-, ou -N(R3)-; et R1, R2 et R3 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe alkyloxy, un groupe alkylthio, un groupe aryle, un groupe aryloxy, un groupe arylthio, un groupe arylalkyle, un groupe arylalkyloxy, un groupe arylalkylthio, un groupe acyle, un groupe acyloxy, un groupe amide, un groupe imide acide, un groupe amino, un groupe amino substitué, un groupe silyle substitué, un groupe silyoxy substitué, un groupe silylthio substitué, un groupe silylamino substitué, un groupe hétérocyclique monovalent, un groupe hétérocyclia heterocyclique oxy, un groupe hétérocyclique thio, un groupe arylalcènyle, un groupe arylalcynyle, un groupe carboxyle, ou un groupe cyano.
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EP2772494B1 (fr) 2011-10-24 2016-09-21 Adeka Corporation Composé bibenzo[b]furane, matériau de conversion photoélectrique, et élément de conversion photoélectrique
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WO2016063771A1 (fr) 2014-10-21 2016-04-28 株式会社Adeka Dérivé de picène, matériau de conversion photoélectrique et élément de conversion photoélectrique

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US5274058A (en) * 1991-09-12 1993-12-28 Board Of Regents, The University Of Texas System Low bandgap polymers rf fused bithiophenes
JPH06179802A (ja) * 1992-12-14 1994-06-28 Katsumi Yoshino 光導電性組成物
JPH08222281A (ja) * 1995-02-14 1996-08-30 Mitsubishi Chem Corp フラーレン類を含有する光化学電池、光電変換素子並びに光化学電池用電極の製造方法

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US5274058A (en) * 1991-09-12 1993-12-28 Board Of Regents, The University Of Texas System Low bandgap polymers rf fused bithiophenes
JPH06179802A (ja) * 1992-12-14 1994-06-28 Katsumi Yoshino 光導電性組成物
JPH08222281A (ja) * 1995-02-14 1996-08-30 Mitsubishi Chem Corp フラーレン類を含有する光化学電池、光電変換素子並びに光化学電池用電極の製造方法

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CHEM. MATER., vol. 16, 2004, pages 3667 - 76 *
MACROMOLECULES, vol. 39, 2006, pages 8870 - 2 *
MACROMOLECULES, vol. 41, 2008, pages 6664 - 71 *

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