WO2021060042A1 - 化合物、組成物、膜、構造体及び電子デバイス - Google Patents

化合物、組成物、膜、構造体及び電子デバイス Download PDF

Info

Publication number
WO2021060042A1
WO2021060042A1 PCT/JP2020/034652 JP2020034652W WO2021060042A1 WO 2021060042 A1 WO2021060042 A1 WO 2021060042A1 JP 2020034652 W JP2020034652 W JP 2020034652W WO 2021060042 A1 WO2021060042 A1 WO 2021060042A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
atom
compound
compound according
Prior art date
Application number
PCT/JP2020/034652
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
和平 金子
寛記 杉浦
伊勢　俊大
幸洋 奥野
剛史 中森
Original Assignee
富士フイルム株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to JP2021548811A priority Critical patent/JP7316365B2/ja
Publication of WO2021060042A1 publication Critical patent/WO2021060042A1/ja

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
    • H10D30/00—Field-effect transistors [FET]
    • H10D30/60—Insulated-gate field-effect transistors [IGFET]
    • H10D30/67—Thin-film transistors [TFT]

Definitions

  • the present invention relates to compounds, membranes, structures and electronic devices.
  • FETs field effect transistors
  • RFIDs radio frequency identifiers: RF tags
  • organic EL Electro Luminescence
  • Patent Document 1 discloses an organic semiconductor compound having a triptycene skeleton.
  • the present invention relates to a compound having excellent reproducibility of carrier mobility when formed into a film, a structure provided with the film, and an electronic device containing the structure, regardless of the film forming method.
  • the purpose is to provide.
  • the present inventors have found that the above-mentioned problems can be solved by using a compound having a triptycene skeleton having a specific structure. That is, the present inventors have found that the above problems can be solved by the following configuration.
  • X represents an oxygen atom or a sulfur atom.
  • R 1 represents a hydrogen atom or an aliphatic hydrocarbon group which may have a substituent.
  • Z represents an oxygen atom, a sulfur atom, a selenium atom, or -NR 2- .
  • R 2 represents a hydrogen atom or an alkyl group.
  • * represents a binding site with A, B or Q in the above general formula
  • ** represents a binding site with a benzene ring in the above general formula.
  • (11) The compound according to any one of (1) to (10) above, wherein Y is a hydrogen atom.
  • a structure comprising a substrate and the film according to (17) above, which is arranged on the surface of the substrate.
  • An electronic device comprising the structure according to (18) above.
  • a compound having excellent reproducibility of carrier mobility when formed into a film, a structure provided with the film, and an electronic device containing the structure, regardless of the film forming method. can be provided.
  • the numerical range represented by using “-” means a range including the numerical values before and after “-” as the lower limit value and the upper limit value.
  • the "aliphatic hydrocarbon group”, “alkyl group”, “alkenyl group”, and “alkenyl group” are linear, branched, and cyclic unless otherwise specified. It shall include those having any of the above structures.
  • each component may be used alone or in combination of two or more.
  • the content of the component means the total content unless otherwise specified.
  • the same symbols (alphabets) are present in the general formula, they may be the same or different unless otherwise specified.
  • the compound of the present invention is a compound represented by the general formula (1) or (2) described later. Since the compound of the present invention has such a structure, it is considered that the above-mentioned effects can be obtained. The reason is not clear, but it is presumed to be as follows. As shown in the general formulas (1) and (2) described later, the compound of the present invention has B (an aliphatic hydrocarbon group having 5 to 22 carbon atoms which may have a substituent) and a triptycene skeleton. ..
  • L represents a single bond or a divalent linking group.
  • A represents a divalent conjugate system linking group having 2 to 10 conjugate rings.
  • B or Q in the general formula via a single bond or a divalent conjugated system linking group the total is 1.
  • B represents an aliphatic hydrocarbon group having 5 to 22 carbon atoms which may have a substituent.
  • R 1 represents a hydrogen atom or an aliphatic hydrocarbon group which may have a substituent.
  • Q represents a hydrogen atom or a halogen atom.
  • n represents 0 or 1.
  • X 1 , X 2 , X 3 and X 4 independently represent groups represented by the following general formulas (AB) or (BA), respectively.
  • Y represents a hydrogen atom or a substituent.
  • the general formula (1) two n in, and, X 1 in the formula (1), X 2, each n is included in X 3 and X 4, out of the total of six n, at least one It is 1.
  • the general formula (2) two n in, and, X 1 in the general formula (2), X 2, each n is included in X 3 and X 4, out of the total of six n, at least one It is 1.
  • L represents a single bond or a divalent linking group.
  • the divalent linking group is not particularly limited, but for example, a linear, branched or cyclic divalent aliphatic hydrocarbon group (for example, an alkylene group such as a methylene group, an ethylene group or a propylene group, or an alkenylene group).
  • Alquinylene group divalent aromatic hydrocarbon group (eg, phenylene group), -O-, -S-, -SO 2- , -NR L- , -CO-, -NH-, -COO-, -CONR L- , -O-CO-O-, -SO 3- , -NHCOO-, -SO 2 NR L- , -NH-CO-NH- or a group combining two or more of these (for example, alkyleneoxy Groups, alkyleneoxycarbonyl groups, alkylenecarbonyloxy groups, etc.) and the like.
  • RL represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
  • the number of atoms connecting the partial structures linearly is an even number (however, the substituent is not included in the above number of atoms) for the reason that the performance reproducibility is better and the carrier mobility is higher. Is preferable.
  • the performance reproducibility is better and the carrier mobility is higher is also referred to as "the effect of the present invention is more excellent”.
  • *-(CH 2 ) 2n-1 Z-** is particularly preferable.
  • Z is an oxygen atom, a sulfur atom, a selenium atom, or, -NR 2 - represents an oxygen atom, preferably a sulfur atom, more preferably oxygen atom.
  • n represents an integer of 1 to 5, more preferably an integer of 1 to 3, and particularly preferably 1.
  • R 2 represents a hydrogen atom or an alkyl group.
  • * represents a binding site with A, B or Q in the general formula
  • ** represents a binding site with a benzene ring (benzene ring constituting triptycene) in the general formula.
  • A represents a divalent conjugate system linking group having 2 to 10 conjugate rings.
  • A is a divalent conjugated system linking group.
  • the divalent conjugated system linking group is a divalent linking group in which the conjugated system is connected from one binding site to the other binding site.
  • the conjugated ring is an aromatic ring or an antiaromatic ring.
  • the aromatic ring is a ring in which the number of electrons contained in the ⁇ -electron system is 4n + 2 (n is an integer of 0 or more), and the antiaromatic ring is a ring in which the number of electrons contained in the ⁇ -electron system is 4n (n).
  • n is a ring of 1 or more).
  • the conjugated ring is preferably an aromatic ring because the effects of the present invention are more excellent.
  • aromatic ring examples include a benzene ring, a pyrrole ring, a thiophene ring, a pyridine ring, a furan ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a selenophene ring, a thiazole ring, an oxazole ring, an imidazole ring, a pyrazole ring, and an isoxazole ring.
  • Isothiazole ring triazole ring, flazan ring, oxadithiazole ring, thiathiazole ring, dioxazole ring, dithiazole ring, azulene ring and the like.
  • a benzene ring and a thiophene ring are preferable because the effects of the present invention are more excellent.
  • antiaromatic ring examples include cyclobutadiene, cyclooctatetraene, pentalene and the like.
  • A has 2-10 conjugate rings.
  • the number of conjugate rings as a single ring is counted.
  • A has a structure in which four conjugated rings are fused (below) (here, * is a binding site), so the number of conjugated rings is four.
  • A preferably has 3 to 8 conjugate rings, more preferably 4 to 6, for the reason that the effect of the present invention is more excellent.
  • the above-mentioned A may have a ring other than the conjugated ring as long as it satisfies the requirements (divalent conjugated system linking group, number of conjugated rings, total number of rings to be fused and number of rings to be bonded).
  • the 2,7-fluorenylene group has a structure in which two benzene rings and one pentadiene ring are fused, and has a pentadiene ring which is a ring other than the conjugated ring. It corresponds to the above A in order to satisfy the group, the number of conjugated rings, the total number of rings to be fused and the number of rings to be bonded).
  • A is a divalent conjugated system linking group (a divalent conjugated group in which the conjugated system is connected from one binding site to the other binding site), and as described later, one binding site to the other. Since the shape extends to the bonding site without branching, the conjugated rings (monocyclic conjugated rings) are fused or bonded by a single bond or a divalent conjugated system linking group.
  • the divalent conjugated system linking group that connects the conjugated rings to each other is not particularly limited as long as it is a divalent linking group that connects the conjugated system from one bonding site to the other bonding site, but the effect of the present invention is more excellent. For this reason, a vinylene group, an ethynylene group, an azo group, and an imino group are preferable.
  • the hydrogen atom of the vinylene group may be substituted.
  • the ring R having a binding site is A that is bound to the ring R via a single bond or a divalent conjugated system linking group and the number of rings fused to the ring R.
  • the total (total X) with the number of rings in the ring is 1, and for the other rings R, the number of rings fused to the ring R and the number of rings fused to the ring R via a single bond or a divalent conjugated system linking group are used.
  • the total (total Y) with the number of rings in A to be bonded is 2.
  • A has a shape that extends from one binding site to the other binding site without branching.
  • the requirement regarding the above total is also referred to as "requirement A".
  • the two benzene rings having a binding site are both fused with one pentadiene ring, and there is no other ring to be condensed or bonded, so that the total X is As for the remaining ring (pentadiene ring), the total Y is 2 because it is fused with the benzene ring at both ends and there is no other ring to be fused or bonded, which satisfies the requirement A.
  • the above-mentioned A is a condensed polycyclic conjugated heterocycle (particularly a condensed aromatic heterocycle) containing an interchalcogen atom (oxygen, sulfur, selenium, tellurium, polonium, livermorium) because the effect of the present invention is more excellent.
  • an interchalcogen atom oxygen, sulfur, selenium, tellurium, polonium, livermorium
  • the condensed polycyclic conjugated heterocycle include a benzothiophene ring and a benzothienobenzothiophene ring.
  • the above-mentioned A is preferably a charge transport group for the reason that the effect of the present invention is more excellent.
  • the above-mentioned A is preferably a group represented by the following general formula (A1), a group represented by the following general formula (A2), or a combination thereof, for the reason that the effect of the present invention is more excellent.
  • Ar 1 , Ar 2 and Ar 3 independently represent a conjugated ring (single ring).
  • p represents an integer from 0 to 8. * Represents the binding site.
  • Specific examples of the conjugated ring (monocycle) are as described above.
  • Ar represents a conjugated ring (monocyclic or condensed ring).
  • M represents a single bond or a divalent conjugated system linking group (for example, a vinylene group, an ethynylene group, an azo group, an imino group, in which the hydrogen atom of the vinylene group may be substituted).
  • q represents an integer from 0 to 8. * Represents the binding site.
  • conjugated ring (monocycle)
  • the conjugated ring is a fused ring
  • the condensed ring satisfies the above-mentioned requirement A.
  • the number of conjugate rings as a single ring included in the general formula (A2) (for fused rings, the number of conjugated rings constituting the fused rings is counted) is 10 at the maximum.
  • B is an aliphatic group having 5 to 22 carbon atoms which may have a substituent (for example, a group selected from the substituent group Z described later).
  • a substituent for example, a group selected from the substituent group Z described later.
  • the carbon atom constituting the aliphatic hydrocarbon group is replaced with an oxygen atom, a sulfur atom, a silicon atom,>
  • C X (X represents an oxygen atom or a sulfur atom), or -NR 1-. It may have been.
  • R 1 represents a hydrogen atom or an aliphatic hydrocarbon group which may have a substituent.
  • the carbon atom in the substituent is not counted in the carbon number.
  • the aliphatic hydrocarbon group before substitution may have 5 to 22 carbon atoms.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic. Specific examples of the aliphatic hydrocarbon group include a linear, branched or cyclic alkyl group, alkenyl group, alkynyl group and the like. Among them, a linear alkyl group is preferable because the effect of the present invention is more excellent.
  • the aliphatic hydrocarbon group represented by B is preferably 8 to 20 carbon atoms, more preferably 10 to 20 carbon atoms, and particularly preferably 12 to 18 carbon atoms. Further, for the reason that the effect of the present invention is more excellent, the aliphatic hydrocarbon group represented by B is an unsubstituted alkyl group, a halogenated alkyl group, an unsubstituted alkenyl group, a halogenated alkenyl group, or an unsubstituted alkenyl group.
  • alkynyl group an alkenyl halide group, an alkyl group substituted with an oxygen atom, an alkenyl group substituted with an oxygen atom, or an alkynyl group substituted with an oxygen atom. More preferably, it is an unsubstituted alkyl group, a halogenated alkyl group, an unsubstituted alkenyl group, an unsubstituted alkynyl group, or an alkyl group substituted with an oxygen atom. It is particularly preferable that the alkyl group is unsubstituted or an alkyl group substituted with an oxygen atom.
  • Q represents a hydrogen atom or a halogen atom.
  • the above Q is preferably a hydrogen atom or a fluorine atom for the reason that the effect of the present invention is more excellent.
  • n represents 0 or 1. At least one of n in the general formulas (1) and (2) is preferably 1 for the reason that the effect of the present invention is more excellent.
  • the two n in the general formula (1) are preferably 1 for the reason that the effect of the present invention is more excellent.
  • the two n in the general formula (2) are preferably 1 for the reason that the effect of the present invention is more excellent.
  • X 1 , X 2 , X 3 and X 4 independently represent groups represented by the following general formulas (AB) or (BA), respectively.
  • L, A, B and Q in the general formulas (AB) and (BA) include L, A, B and in the general formulas (1) and (2). It is the same as Q.
  • m and n independently represent 0 or 1, respectively.
  • * represents a binding site.
  • m is preferably 1 for the reason that the effect of the present invention is more excellent.
  • n is preferably 1 for the reason that the effect of the present invention is more excellent.
  • the compound of the present invention is a compound represented by the general formula (1)
  • the above X 1 is a group represented by the general formula (AB) for the reason that the effect of the present invention is more excellent. Is preferable.
  • the compound of the present invention is a compound represented by the general formula (2)
  • the above X 1 is a group represented by the general formula (BA) for the reason that the effect of the present invention is more excellent. Is preferable.
  • n is the reason that the effect or the like of the present invention is more excellent, it is 1 preferable.
  • Y represents a hydrogen atom or a substituent (for example, a group selected from the substituent group Z described later).
  • the above-mentioned substituent may be a group represented by the above-mentioned general formula (AB) or (BA).
  • the Y is preferably a hydrogen atom because the effect of the present invention is more excellent.
  • the general formula (1) two n in, and, X 1 in the formula (1), X 2, each n is included in X 3 and X 4, out of the total of six n, at least one One is 1.
  • the compound of the present invention has at least one group represented by B above.
  • each n contained in X 1 , X 2 , X 3 and X 4 in the general formula (1) is a general formula X 1 , X 2 , X 3 and X 4 in the general formula (1).
  • each n contained in X 1 , X 2 , X 3 and X 4 in the general formula (2) is a general X 1 , X 2 , X 3 and X 4 in the general formula (2). It represents each n (a total of four n) in the group represented by the formula (AB) or (BA).
  • 3 to 6 n are preferably 1 for the reason that the effect of the present invention is more excellent.
  • the compound of the present invention is preferably a compound represented by the above-mentioned general formula (1) for the reason that the effects of the present invention are more excellent.
  • the compound represented by the general formula (1) described above is preferably a compound represented by the following general formula (3) because the effects of the present invention and the like are more excellent.
  • L, A, B, Q and Y in the general formula (3) are the same as those of L, A, B, Q and Y in the general formula (1) described above. ..
  • m and n independently represent 0 or 1, respectively. However, at least one of the three n in the general formula (3) is 1.
  • the m in the general formula (3) is preferably 1 for the reason that the effect of the present invention is more excellent. It is preferable that m and n in the general formula (3) are both 1 for the reason that the effect of the present invention is more excellent.
  • the compound of the present invention is preferably a compound represented by the following general formula (4) for the reason that the effects of the present invention are more excellent.
  • L, A, B, Q and Y in the general formula (4) are the same as L, A, B, Q and Y in the general formulas (1) and (2) described above. Each is the same.
  • m and n independently represent 0 or 1, respectively. However, at least one of the three n in the general formula (4) is 1.
  • the m in the general formula (4) is preferably 1 for the reason that the effect of the present invention is more excellent. It is preferable that m and n in the general formula (4) are both 1 for the reason that the effect of the present invention is more excellent.
  • the compound of the present invention is preferably a compound represented by the following general formula (5) for the reason that the effects of the present invention are more excellent.
  • L, A, B, Q, X 2 , X 3 , X 4 and Y in the general formula (5) are described in L, A, B in the general formula (1) described above. , Q, X 2 , X 3 , X 4 and Y, respectively.
  • n represents 0 or 1. However, three of n in the general formula (5) and, each n is included in the general formula (5) X 2, X 3 and X 4 in, out of the total of six n, at least one is 1 ..
  • At least one of n in the general formula (5) is preferably 1 for the reason that the effect of the present invention is more excellent.
  • the three n in the general formula (5) are preferably 1 for the reason that the effect of the present invention is more excellent.
  • the method for synthesizing the compound of the present invention is not particularly limited, and the compound can be synthesized with reference to a usual method. For example, it can be synthesized as in the examples described later.
  • Substituent group Z includes halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, silyl group, alkoxy group, amino group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, Acyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, Arylsulfonyl group, silyloxy group, heterocyclic oxy group, carbamoyl group, carbamoyl group, carbamoyl group, carbamoyl group, carbamoyl
  • halogen atom contained in the substituent group Z examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom or a chlorine atom is preferable.
  • the alkyl group contained in the substituent group Z is not particularly limited, but an alkyl group having 1 (3) to 30 carbon atoms is preferable, an alkyl group having 1 (3) to 20 carbon atoms is more preferable, and an alkyl group having 4 to 20 carbon atoms is more preferable. Alkyl groups of are more preferred.
  • the numbers in parentheses represent the number of carbon atoms in the case of a cycloalkyl group.
  • alkyl group which may have a substituent contained in the substituent group Z include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, a butyl group, an amyl group, a pentyl group, and a 1-methylpentyl group.
  • the alkenyl group contained in the substituent group Z is not particularly limited, but an alkenyl group having 2 to 20 carbon atoms is preferable, an alkenyl group having 2 to 12 carbon atoms is more preferable, and an alkenyl group having 2 to 8 carbon atoms is further preferable. ..
  • Examples of the alkenyl group which may have a substituent contained in the substituent group Z include a vinyl group, an allyl group, a 2-butenyl group, a 1-pentenyl group, and a 4-pentenyl group.
  • the alkynyl group contained in the substituent group Z is not particularly limited, but an alkynyl group having 2 to 20 carbon atoms is preferable, an alkynyl group having 2 to 12 carbon atoms is more preferable, and an alkynyl group having 2 to 8 carbon atoms is further preferable. ..
  • Examples of the alkynyl group which may have a substituent contained in the substituent group Z include an ethynyl group, a propargyl group, a 1-pentynyl group, a trimethylsilylethynyl group, a triethylsilylethynyl group and a tri-i-propylsilylethynyl group. , And 2-p-propylphenylethynyl groups.
  • the aryl group contained in the substituent group Z is not particularly limited, but an aryl group having 6 to 20 carbon atoms is preferable, and an aryl group having 6 to 12 carbon atoms is more preferable.
  • Examples of the aryl group which may have a substituent contained in the substituent group Z include a phenyl group, a naphthyl group, a 2,4,6-trimethylphenyl group, a p- (t-butyl) phenyl group, and 4-.
  • Methyl-2,6-dipropylphenyl group 4-fluorophenyl group, 4-trifluoromethylphenyl group, p-pentylphenyl group, 3,4-dipentylphenyl group, p-heptoxyphenyl group, and 3, Examples include 4-dihepptoxyphenyl group.
  • the heterocyclic group contained in the substituent group Z includes, for example, three or more atoms constituting the ring, and at least one heteroatom and 1 to 30 carbon atoms as the atoms constituting the ring.
  • Examples include heterocyclic groups containing atoms.
  • the heterocyclic group includes an aromatic heterocyclic group (heteroaryl group) and an aliphatic heterocyclic group.
  • Examples of the hetero atom constituting the ring include a nitrogen atom, an oxygen atom, and a sulfur atom, and the number thereof is not particularly limited, but is, for example, one or two.
  • the number of carbon atoms constituting the ring is preferably 3 to 20, more preferably 5 to 12.
  • heterocyclic group a 5-membered ring, a 6-membered ring, or a group of these fused rings is preferable.
  • the heterocyclic group contained in the substituent group Z include a thienyl group, a thiazolyl group, an imidazolyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, a furanyl group, a selenophyl group, a piperidyl group, a morpholino group and a benzoxazolyl.
  • examples thereof include a group, a benzimidazolyl group, a benzthiazolyl group, a 2-hexylfuranyl group, and a pyranyl group.
  • the silyl group which may have a substituent contained in the substituent group Z is not particularly limited, but has a group selected from an alkyl group and an aryl group as the substituent and has 3 to 40 carbon atoms (more preferably). Is 3 to 30, more preferably 3 to 24), and a silyl group is preferable.
  • Examples of the silyl group which may have a substituent contained in the substituent group Z include a trimethylsilyl group, a triphenylsilyl group, and a dimethylphenylsilyl group.
  • the alkoxy group contained in the substituent group Z is not particularly limited, but an alkoxy group having 1 to 20 carbon atoms is preferable, an alkoxy group having 1 to 12 carbon atoms is more preferable, and an alkoxy group having 1 to 8 carbon atoms is further preferable. preferable.
  • Examples of the alkoxy group contained in the substituent group Z include a methoxy group, an ethoxy group, and a butoxy group.
  • the amino group which may have a substituent contained in the substituent group Z is not particularly limited, but has an amino group or a group selected from an alkyl group and an aryl group as a substituent and has a carbon number of carbons. Amino groups of 1 to 20 (more preferably 1 to 10, still more preferably 1 to 6) are preferred. Examples of the amino group which may have a substituent contained in the substituent group Z include an amino group, a methylamino group, a dimethylamino group, a diethylamino group, a dibenzylamino group, and an anilino group.
  • the aryloxy group contained in the substituent group Z is not particularly limited, but an aryloxy group having 6 to 20 carbon atoms is preferable, an aryloxy group having 6 to 16 carbon atoms is more preferable, and an aryloxy group having 6 to 12 carbon atoms is more preferable. Groups are even more preferred.
  • Examples of the aryloxy group contained in the substituent group Z include a phenyloxy group and 2-naphthyloxy.
  • the acyl group contained in the substituent group Z is not particularly limited, but an acyl group having 1 to 20 carbon atoms is preferable, an acyl group having 1 to 16 carbon atoms is more preferable, and an acyl group having 1 to 12 carbon atoms is further preferable. ..
  • Examples of the acyl group which may have a substituent contained in the substituent group Z include an acetyl group, a hexanoyl group, a benzoyl group, a formyl group, and a pivaloyl group.
  • the alkoxycarbonyl group contained in the substituent group Z is not particularly limited, but an alkoxycarbonyl group having 2 to 20 carbon atoms is preferable, an alkoxycarbonyl group having 2 to 16 carbon atoms is more preferable, and an alkoxycarbonyl group having 2 to 12 carbon atoms is more preferable.
  • the group is more preferable, and the methoxycarbonyl group or the ethoxycarbonyl group is particularly preferable.
  • the aryloxycarbonyl group contained in the substituent group Z is not particularly limited, but an aryloxycarbonyl group having 7 to 20 carbon atoms is preferable, an aryloxycarbonyl group having 7 to 16 carbon atoms is more preferable, and an aryloxycarbonyl group having 7 to 10 carbon atoms is more preferable.
  • the aryloxycarbonyl group of the above is more preferable, and the phenyloxycarbonyl group is particularly preferable.
  • the acyloxy group contained in the substituent group Z is not particularly limited, but an acyloxy group having 2 to 20 carbon atoms is preferable, an acyloxy group having 2 to 16 carbon atoms is more preferable, and an acyloxy group having 2 to 10 carbon atoms is further preferable. ..
  • Examples of the acyloxy group which may have a substituent contained in the substituent group Z include an acetoxy group, a benzoyloxy group, and a (meth) acryloyloxy group.
  • the acylamino group contained in the substituent group Z is not particularly limited, but an acylamino group having 2 to 20 carbon atoms is preferable, an acylamino group having 2 to 16 carbon atoms is more preferable, and an acylamino group having 2 to 10 carbon atoms is further preferable. ..
  • Examples of the acylamino group contained in the substituent group Z include an acetylamino group and a benzoylamino group.
  • the aminocarbonylamino group contained in the substituent group Z is not particularly limited, but an aminocarbonylamino group having 2 to 20 carbon atoms is preferable, an aminocarbonylamino group having 2 to 16 carbon atoms is more preferable, and an aminocarbonylamino group having 2 to 12 carbon atoms is more preferable. Aminocarbonylamino groups are more preferred, and ureido groups are particularly preferred.
  • the alkoxycarbonylamino group contained in the substituent group Z is not particularly limited, but an alkoxycarbonylamino group having 2 to 20 carbon atoms is preferable, an alkoxycarbonylamino group having 2 to 16 carbon atoms is more preferable, and an alkoxycarbonylamino group having 2 to 12 carbon atoms is more preferable.
  • the alkoxycarbonylamino group of the above is more preferable, and the methoxycarbonylamino group is particularly preferable.
  • the aryloxycarbonylamino group contained in the substituent group Z is not particularly limited, but an aryloxycarbonylamino group having 7 to 20 carbon atoms is preferable, an aryloxycarbonylamino group having 7 to 16 carbon atoms is more preferable, and an aryloxycarbonylamino group having 7 to 16 carbon atoms is more preferable. 7-12 aryloxycarbonylamino groups are more preferred, and phenyloxycarbonylamino groups are particularly preferred.
  • the alkylthio group contained in the substituent group Z is not particularly limited, but an alkylthio group having 1 to 20 carbon atoms is preferable, an alkylthio group having 1 to 16 carbon atoms is more preferable, and an alkylthio group having 1 to 12 carbon atoms is further preferable. ..
  • Examples of the alkylthio group contained in the substituent group Z include a methylthio group, an ethylthio group, and an octylthio group.
  • the arylthio group contained in the substituent group Z is not particularly limited, but an arylthio group having 6 to 20 carbon atoms is preferable, an arylthio group having 6 to 16 carbon atoms is more preferable, and an arylthio group having 6 to 12 carbon atoms is further preferable. , Phenylthio groups are particularly preferred.
  • the group selected from the substituent group Z described above may further have a substituent.
  • a substituent examples include a group selected from the substituent group Z.
  • the number of substituents having a substituent (also referred to as a combined group) is not particularly limited, but for example, 1 to 6 is preferable, and 1 to 3 is more preferable.
  • the group to be combined is not particularly limited, and examples thereof include the above-mentioned groups in which each of the above-mentioned groups preferable as the group selected from the substituent group Z is substituted with another group selected from the substituent group Z. Be done.
  • halogen atom alkyl group, aryl group, heterocyclic group (heteroaryl group), alkoxy group (including hydroxyalkoxy group, halogenated alkoxy group, heteroarylalkoxy group), amino group, acyloxy group, hydroxy
  • An alkyl group having a group selected from the group consisting of a group, a sulfato group, and a phosphono group as a substituent, an aryl halide group or a (fluorinated) alkylaryl group, an alkynyl group having a silyl group as a substituent, etc. Can be mentioned.
  • an alkyl group having a halogen atom as a substituent (alkyl halide group) or an alkyl group having an aryl group as a substituent is preferable, and an alkyl group having a fluorine atom as a substituent (huh).
  • Alkyl compound group) or an alkyl group having an aryl group as a substituent is more preferable, and an alkyl group having an aryl group as a substituent is further preferable.
  • the compound of the present invention is, for example, an organic thin film that controls the amount of current or voltage, an organic photoelectric conversion element that converts light energy into electric power (for example, a solid-state imaging device for optical sensors, and a solar cell for energy conversion).
  • an organic photoelectric conversion element that converts light energy into electric power
  • OLED organic light emitting diode
  • phototransistor organic light emitting diode
  • OLET organic light emitting transistor
  • organic thermoelectric conversion element that converts heat energy into electric power
  • gas sensor for example, organic rectifying element, organic inverter, and information recording element.
  • the film of the present invention is a film (organic semiconductor film) containing the above-mentioned compound of the present invention.
  • the membrane of the present invention contains the above-mentioned compound of the present invention.
  • the film of the present invention may be a monolayer film or a laminated film.
  • the content of the compound of the present invention in the film of the present invention is not particularly limited, but is preferably 10% by mass or more, more preferably 30% by mass or more, for the reason that the effect of the present invention is more excellent. , 50% by mass or more, and particularly preferably 90% by mass or more.
  • the upper limit is not particularly limited and is 100% by mass.
  • the upper limit of the content of the compound of the present invention in the film of the present invention is 90% by mass or less because the effect of the present invention is more excellent. It is preferably present, and more preferably 80% by mass or less.
  • the film of the present invention may contain a component (arbitrary component) other than the above-mentioned compound of the present invention.
  • the film of the present invention may contain a binder polymer.
  • the film quality may be improved by containing the binder polymer.
  • the content of the compound of the present invention and the binder polymer is not particularly limited, but the compound of the present invention and the binder polymer are phase-separated from each other along the film thickness direction in terms of carrier mobility. It is preferable to have.
  • the type of the binder polymer is not particularly limited, and a known binder polymer can be used.
  • the binder polymer include polystyrene, poly ( ⁇ -methylstyrene), polycarbonate, polyarylate, polyester, polyamide, polyimide, polyurethane, polysiloxane, polysulphon, polymethylmethacrylate, polymethylacrylate, cellulose, polyethylene, and. Insulating polymers containing polypropylene and copolymers thereof are mentioned.
  • ethylene-propylene rubber acrylonitrile-butadiene rubber, hydrogenated nitrile rubber, fluororubber, perfluoroepolymer, tetrafluoroethylene propylene copolymer, ethylene-propylene-diene copolymer, styrene- Butadiene rubber, polychloroprene, polyneoprene, butyl rubber, methylphenyl silicone resin, methylphenyl vinyl silicone resin, methyl vinyl silicone resin, fluorosilicone resin, acrylic rubber, ethylene acrylic rubber, chlorosulfonated polyethylene, chloropolyethylene, epichlorohydrin Rubber containing copolymer, polyisoprene-natural rubber copolymer, polyisoprene rubber, styrene-isoprene block copolymer, polyester urethane copolymer, polyether urethane copolymer, polyether ester thermoplastic elasto
  • polyvinylcarbazole and a photoconductive polymer containing polysilane examples include polyvinylcarbazole and a photoconductive polymer containing polysilane, a conductive polymer containing polythiophene, polypyrrole, polyaniline, and polyparaphenylene vinylene, and Chemistry of Materials, 2014, 26, 647.
  • the binder polymer preferably has a structure that does not contain a polar group in consideration of charge mobility.
  • the polar group means a functional group having a hetero atom other than a carbon atom and a hydrogen atom.
  • Polystyrene or poly ( ⁇ -methylstyrene) is preferable as the binder polymer because it has a structure containing no polar group.
  • semiconductor polymers are preferred.
  • the glass transition temperature of the binder polymer is not particularly limited and is appropriately set according to the application. For example, when imparting strong mechanical strength to an organic semiconductor film, it is preferable to raise the glass transition temperature. On the other hand, when imparting flexibility to the organic semiconductor film, it is preferable to lower the glass transition temperature.
  • the binder polymer may be used alone or in combination of two or more.
  • the weight average molecular weight of the binder polymer is not particularly limited, but is preferably 10 to 10 million, more preferably 30 to 5 million, and even more preferably 50 to 3 million.
  • the weight average molecular weight of the binder polymer can be determined by gel permeation chromatography (GPC).
  • the content is not particularly limited, but the lower limit is preferably 10% by mass or more, preferably 20% by mass or more, for the reason that the effect of the present invention is more excellent. It is more preferable, and the upper limit is preferably 90% by mass or less, more preferably 70% by mass or less, for the reason that the effect of the present invention is more excellent.
  • optional ingredients other than the binder polymer include additives usually used for organic semiconductor membranes, and more specifically, surfactants, antioxidants, crystallization control agents, and crystal orientation control agents. Can be mentioned. As the surfactant and the antioxidant, paragraphs 0136 and 0137 of JP2015-195362A can be incorporated, and the contents thereof are incorporated in the present specification.
  • the content thereof is preferably 10% by mass or less, more preferably 5% by mass or less, and 1% by mass because the effects of the present invention are more excellent. The following is more preferable.
  • the film thickness of the film of the present invention is not particularly limited, but 5 to 500 nm is preferable, and 5 to 200 nm is more preferable for the reason that the effect of the present invention is more excellent.
  • the application of the film of the present invention is not limited to the organic semiconductor film for organic TFTs, and can be used as the organic semiconductor film included in each of the above-mentioned organic semiconductor devices.
  • the method for producing the film of the present invention is not particularly limited, and examples thereof include a method of preparing a composition (organic semiconductor composition) containing the compound of the present invention described above and then applying the composition to a substrate or the like.
  • composition of the present invention is a composition (organic semiconductor composition) containing the above-mentioned compound of the present invention.
  • the composition of the present invention is preferably a composition (organic semiconductor composition) containing the above-mentioned compound of the present invention and at least one kind of solvent.
  • the composition of the present invention may contain components other than the above-mentioned compounds of the present invention.
  • the composition of the present invention preferably contains a solvent from the viewpoint of improving the coatability.
  • a solvent is not particularly limited as long as it dissolves or disperses the above-mentioned compound, and examples thereof include an inorganic solvent and an organic solvent, and an organic solvent is preferable.
  • the solvent may be used alone or in combination of two or more.
  • the organic solvent is not particularly limited, but hexane, octane, decane, toluene, xylene, mecitylene, ethylbenzene, amylbenzene, decalin, 1-methylnaphthalene, 1-ethylnaphthalene, 1,6-dimethylnaphthalene, and tetraline can be used.
  • Examples thereof include a phosphate ester solvent containing trimethyl, a nitrile solvent containing acetonitrile and benzonitrile, and a nitro solvent containing nitromethane and nitrobenzene.
  • a hydrocarbon solvent, a ketone solvent, a halogenated hydrocarbon solvent, a heterocyclic solvent, a halogenated heterocyclic solvent, an ester solvent, an alcohol solvent, an alkoxyalcohol solvent, an ether solvent, or a nitrile solvent is preferable, and toluene, xylene, and mesitylene are preferable.
  • a solvent having a boiling point of 100 ° C. or higher is preferable in terms of film quality and the ability to enlarge the crystals of the above-mentioned compounds.
  • toluene xylene, mesitylene, tetraline, acetophenone, propiophenone, butyrophenone, dichlorobenzene, anisole, ethoxybenzene, propoxybenzene, isopropoxybenzene, butoxybenzene, 2-methylanisole, 3 -Methylanisole, 4-methylanisole, 1-methoxy-2-propanol, 2-methoxyethanol, 2-butoxyethanol, and benzonitrile can be mentioned.
  • toluene, xylene, tetraline, acetophenone, propiophenone, butyrophenone, anisole, ethoxybenzene, propoxybenzene, butoxybenzene, 2-methylanisole, 3-methylanisole, 4-methylanisole, or 2-butoxyethanol are more suitable.
  • a non-halogen solvent solvent having no halogen atom in the molecule
  • the solvent having a boiling point of 100 ° C. or higher is preferable as the solvent having a boiling point of 100 ° C. or higher.
  • the content of the solvent is preferably 90 to 99.9% by mass, more preferably 95 to 99.9% by mass, based on the total mass of the composition of the present invention. , 96-99.5% by mass, more preferably.
  • the viscosity of the composition of the present invention is preferably 10 mPa ⁇ s or more in terms of printability.
  • the method for preparing the composition of the present invention is not particularly limited, and a usual preparation method can be adopted. For example, a method of mixing the compound of the present invention with a solvent can be mentioned. If necessary, each component can be heated during or after stirring.
  • the heating temperature is not particularly limited and is determined, for example, in the range of 40 to 150 ° C. When a solvent is used, the temperature is determined to be within the above range and below the boiling point of the solvent.
  • the structure of the present invention is a structure including a substrate and the film (organic semiconductor film) of the present invention described above.
  • the substrate is the same as that of the organic thin film transistor described later.
  • the electronic device of the present invention is an electronic device including the above-described structure of the present invention.
  • the organic thin film transistor of the present invention is the above-mentioned electronic device of the present invention, which is an organic thin film transistor (organic TFT).
  • the organic TFT includes the above-mentioned organic semiconductor film. As a result, the organic TFT exhibits high carrier mobility, and is effectively suppressed from decreasing with time even in the atmosphere, and is stably driven.
  • the ambient temperature and humidity in the atmosphere are not particularly limited as long as they are the temperature and humidity in the environment in which the organic TFT is used. For example, the temperature is room temperature (20 ° C.) and the humidity is 10 to 90 RH%.
  • the organic TFT is preferably used as an organic field effect transistor (FET), and more preferably used as an insulated gate type FET in which the gate and the channel are insulated.
  • the thickness of the organic TFT is not particularly limited, but in the case of a thinner transistor, for example, the thickness of the entire organic TFT is preferably 0.1 to 0.5 ⁇ m.
  • the organic TFT has the above-mentioned organic semiconductor film (also referred to as an organic semiconductor layer or a semiconductor active layer), and may further have a source electrode, a drain electrode, a gate electrode, and a gate insulating film.
  • the organic TFT is provided on the substrate in contact with the gate electrode, the organic semiconductor film, the gate insulating film provided between the gate electrode and the organic semiconductor film, and the organic semiconductor film, and is connected via the organic semiconductor film. It is preferable to have a source electrode and a drain electrode.
  • an organic semiconductor film and a gate insulating film are provided adjacent to each other.
  • the structure of the organic TFT is not particularly limited as long as it includes each of the above layers.
  • the organic TFT may have any structure of bottom gate-bottom contact type, top gate-bottom contact type, bottom gate-top contact type, and top gate-top contact type.
  • a bottom gate type bottom gate-bottom contact type or bottom gate-top contact type in which a gate electrode is provided between the substrate and the organic semiconductor film is preferable.
  • an example of the organic TFT will be described with reference to the drawings.
  • FIG. 1 is a schematic cross-sectional view showing the structure of a bottom gate-bottom contact type organic TFT 10 which is an example of an organic TFT.
  • the organic TFT 10 includes a substrate (base material) 1, a gate electrode 2, a gate insulating film 3, a source electrode 4A, a drain electrode 4B, an organic semiconductor film 5, and a sealing layer 6.
  • a substrate (base material), a gate electrode, a gate insulating film, a source electrode, a drain electrode, an organic semiconductor film, a sealing layer, and a method for producing each of them will be described.
  • the substrate serves to support the gate electrode, the source electrode, the drain electrode, and other layers.
  • the type of the substrate is not particularly limited, and examples thereof include a plastic substrate, a silicon substrate, a glass substrate, and a ceramic substrate. Above all, a glass substrate or a plastic substrate is preferable from the viewpoint of applicability to each device and cost.
  • the thickness of the substrate is not particularly limited.
  • the upper limit of the thickness of the substrate is preferably 10 mm or less, more preferably 2 mm or less, and further preferably 1.5 mm or less.
  • the lower limit of the thickness of the substrate is preferably 0.01 mm or more, more preferably 0.05 mm or more.
  • a normal electrode used as a gate electrode of an organic TFT can be applied without particular limitation.
  • the material (electrode material) for forming the gate electrode is not particularly limited, and is, for example, a metal containing gold, silver, aluminum, copper, chromium, nickel, cobalt, titanium, platinum, magnesium, calcium, barium, and sodium. , InO 2 , SnO 2 , and conductive oxides including indium tin oxide (ITO), polyaniline, polypyrrole, polythiophene, polyacetylene, and conductive polymers containing polydiacetylene, silicon, germanium, and gallium.
  • ITO indium tin oxide
  • Examples include semiconductors containing arsenic, and carbon materials containing fullerene, carbon nanotubes, and graphite. Among them, the above metal is preferable, and silver or aluminum is more preferable.
  • the thickness of the gate electrode is not particularly limited, but is preferably 20 to 200 nm.
  • the gate electrode may function as the substrate, and in this case, the substrate may be omitted.
  • the method for forming the gate electrode is not particularly limited, and for example, a method of vacuum-depositing (hereinafter, simply referred to as “vapor deposition”) or sputtering of the above-mentioned electrode material on a substrate, and an electrode containing the above-mentioned electrode material. Examples thereof include a method of applying or printing the forming composition.
  • vapor deposition a method of vacuum-depositing
  • examples of the patterning method include a printing method including inkjet printing, screen printing, offset printing, and letterpress printing (flexographic printing), a photolithography method, and a mask vapor deposition method. ..
  • the gate insulating film is not particularly limited as long as it is a layer having an insulating property, and may be a single layer or a multilayer.
  • the material for forming the gate insulating film is not particularly limited, and for example, polymethylmethacrylate, polystyrene, polyvinylphenol, melamine resin, polyimide, polycarbonate, polyester, polyvinyl alcohol, polyvinylacetate, polyurethane, polysulphon, and polybenzoxa. Examples thereof include polymers containing sol, polyvinyl sesquioxane, epoxy resins and phenolic resins, silicon dioxide, aluminum oxide, inorganic oxides containing titanium oxide, and nitrides containing silicon nitride.
  • the polymer is preferable from the viewpoint of compatibility with the organic semiconductor film
  • the inorganic oxide is preferable from the viewpoint of film uniformity
  • silicon dioxide is more preferable.
  • the film thickness of the gate insulating film is not particularly limited, but is preferably 100 to 1000 nm.
  • the method for forming the gate insulating film is not particularly limited, and for example, a method of applying a gate insulating film forming composition containing the above material on a substrate on which a gate electrode is formed, and a method of depositing or depositing the above material. A method of sputtering can be mentioned.
  • a source electrode is an electrode into which a current flows from the outside through wiring.
  • the drain electrode is an electrode that sends an electric current to the outside through wiring.
  • the material for forming the source electrode and the drain electrode the same material as the electrode material for forming the gate electrode described above can be used. Among them, metal is preferable, and gold or silver is more preferable.
  • the thickness of the source electrode and the drain electrode is not particularly limited, but is preferably 1 nm or more, and more preferably 10 nm or more, respectively.
  • the upper limit of the thickness of the source electrode and the drain electrode is preferably 500 nm or less, more preferably 300 nm or less.
  • the distance (gate length L) between the source electrode and the drain electrode can be appropriately determined, but is preferably 200 ⁇ m or less, more preferably 100 ⁇ m or less.
  • the gate width W can be appropriately determined, but is preferably 5000 ⁇ m or less, and more preferably 1000 ⁇ m or less.
  • the ratio of the gate width W to the gate length L is not particularly limited, but for example, the ratio W / L is preferably 10 or more, and more preferably 20 or more.
  • the method of forming the source electrode and the drain electrode is not particularly limited, and for example, a method of vacuum-depositing or sputtering an electrode material on a substrate on which a gate electrode and a gate insulating film are formed, and an electrode forming composition. Examples include a method of applying or printing.
  • the patterning method for patterning the source electrode and the drain electrode is the same as the above-described gate electrode patterning method.
  • Organic semiconductor film is the film of the present invention described above.
  • the entire organic TFT may be sealed with a metal sealing can, or a sealing layer may be formed using a sealing agent.
  • a sealing agent composition for forming a sealing layer usually used for organic TFTs can be used.
  • the sealing agent include an inorganic material containing glass and silicon nitride, a polymer material containing parylene, and a low molecular weight material.
  • the sealing layer can be formed by a usual method such as coating and drying using the above-mentioned sealing agent.
  • the thickness of the sealing layer is not particularly limited, but is preferably 0.2 to 10 ⁇ m.
  • FIG. 2 is a schematic cross-sectional view showing the structure of a bottom gate-top contact type organic TFT 20 which is an example of an organic TFT.
  • the organic TFT 20 has a substrate 1, a gate electrode 2, a gate insulating film 3, an organic semiconductor film 5, a source electrode 4A, a drain electrode 4B, and a sealing layer 6 in this order. Be prepared.
  • the organic TFT 20 is the same as the organic TFT 10 except that the layer structure (lamination mode) is different. Therefore, the substrate, the gate electrode, the gate insulating film, the source electrode, the drain electrode, the organic semiconductor film, and the sealing layer are the same as those in the bottom gate-bottom contact type organic TFT described above. Is omitted.
  • the organic TFT of the present invention is not particularly limited in its use, and can be used for, for example, electronic paper, display devices, sensors, and electronic tags.
  • Comparative compound (1) was synthesized by the method described in paragraphs [0130] to [0133] of Japanese Patent No. 6219314.
  • Comparative compound (2) was synthesized by the method described in paragraph [0228] of Japanese Patent No. 4945757.
  • the obtained solid was dissolved in chloroform, and the solid precipitated by adding methanol was filtered and dried to obtain an intermediate (4-1) (245 mg, yield 55%).
  • a thermal oxide film (thickness ) of SiO 2 is formed on the surface of a p-type silicon substrate (thickness: 0.4 mm, corresponding to a substrate 1 provided with a gate electrode 2) 1.
  • a substrate (size: 25 mm ⁇ 25 mm) having (s: 200 nm) was prepared.
  • the surface of the thermal oxide film (gate insulating film 3) of this substrate was washed with ultraviolet rays (UV) -ozone and then treated with ⁇ -phenetiltrimethoxysilane.
  • UV ultraviolet rays
  • the organic semiconductor film 5 was formed by the following three types of film forming methods.
  • Mobility ratio (maximum carrier mobility in 10 organic thin film transistors) / (minimum carrier mobility in 10 organic thin film transistors) Then, it was evaluated according to the following evaluation criteria. The results are shown in Table 1. Practically, it is preferable that A or B is used in any of the film forming methods. (Evaluation criteria) ⁇ A: Mobility ratio is less than 1.5 ⁇ B: Mobility ratio is 1.5 or more and less than 1.8 ⁇ C: Mobility ratio is 1.8 or more and less than 2.1 ⁇ D: Mobility ratio is 2. 1 or more
  • Examples 1 to 9 which are organic thin films using certain compounds (1) to (9) for the organic semiconductor film, showed excellent performance reproducibility.
  • Examples 1 to 8 in which the compound of the present invention is a compound represented by the general formula (5) showed better performance reproducibility (spin coating) and higher carrier mobility.
  • Examples 1 to 5 and Examples 7 to 8 in which the number of conjugated rings of A in the general formula (5) is 3 or more showed higher carrier mobility.
  • the compound of the present invention is a compound represented by the general formula (1), and L in the general formula (1) is the above-mentioned * -CH 2 Z-**.
  • One Example 1 showed better performance reproducibility (dropcast) and higher carrier mobility.
  • Substrate 2 Gate electrode 3 Gate insulating film 4A Source electrode 4B Drain electrode 5 Organic semiconductor film (organic semiconductor layer) 6 Sealing layer 10, 20 Organic thin film transistor (organic TFT)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid State Image Pick-Up Elements (AREA)
  • Thin Film Transistor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
PCT/JP2020/034652 2019-09-25 2020-09-14 化合物、組成物、膜、構造体及び電子デバイス WO2021060042A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2021548811A JP7316365B2 (ja) 2019-09-25 2020-09-14 化合物、組成物、膜、構造体及び電子デバイス

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019174704 2019-09-25
JP2019-174704 2019-09-25

Publications (1)

Publication Number Publication Date
WO2021060042A1 true WO2021060042A1 (ja) 2021-04-01

Family

ID=75166942

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/034652 WO2021060042A1 (ja) 2019-09-25 2020-09-14 化合物、組成物、膜、構造体及び電子デバイス

Country Status (2)

Country Link
JP (1) JP7316365B2 (enrdf_load_stackoverflow)
WO (1) WO2021060042A1 (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023282114A1 (ja) * 2021-07-09 2023-01-12 東京エレクトロン株式会社 パターン形成方法、及びプラズマ処理方法
WO2023210378A1 (ja) * 2022-04-28 2023-11-02 Ａｇｃ株式会社 化合物、組成物、表面処理剤、物品の製造方法、及び物品

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004506791A (ja) * 2000-08-21 2004-03-04 マサチューセッツ・インスティチュート・オブ・テクノロジー 高い内部自由体積を有するポリマー
US20120073662A1 (en) * 2010-09-29 2012-03-29 Massachusetts Institute Of Technology Compositions, methods, and systems comprising poly(thiophenes)
WO2012121393A1 (ja) * 2011-03-10 2012-09-13 国立大学法人東京工業大学 有機半導体材料
WO2014111980A1 (ja) * 2013-01-16 2014-07-24 独立行政法人科学技術振興機構 自己組織化膜形成材料として有用なトリプチセン誘導体、その製造方法、それを用いた膜、及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004506791A (ja) * 2000-08-21 2004-03-04 マサチューセッツ・インスティチュート・オブ・テクノロジー 高い内部自由体積を有するポリマー
US20120073662A1 (en) * 2010-09-29 2012-03-29 Massachusetts Institute Of Technology Compositions, methods, and systems comprising poly(thiophenes)
WO2012121393A1 (ja) * 2011-03-10 2012-09-13 国立大学法人東京工業大学 有機半導体材料
WO2014111980A1 (ja) * 2013-01-16 2014-07-24 独立行政法人科学技術振興機構 自己組織化膜形成材料として有用なトリプチセン誘導体、その製造方法、それを用いた膜、及びその製造方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023282114A1 (ja) * 2021-07-09 2023-01-12 東京エレクトロン株式会社 パターン形成方法、及びプラズマ処理方法
WO2023210378A1 (ja) * 2022-04-28 2023-11-02 Ａｇｃ株式会社 化合物、組成物、表面処理剤、物品の製造方法、及び物品

Also Published As

Publication number Publication date
JPWO2021060042A1 (enrdf_load_stackoverflow) 2021-04-01
JP7316365B2 (ja) 2023-07-27

Similar Documents

Publication Publication Date Title
CN109478595B (zh) 有机薄膜晶体管、有机半导体膜、化合物、有机薄膜晶体管用组合物及有机薄膜晶体管的制造方法
KR101917939B1 (ko) 유기 박막 트랜지스터 및 그 제조 방법
JP5975834B2 (ja) 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
US11011706B2 (en) Organic semiconductor element, organic semiconductor composition, organic semiconductor film, method of manufacturing organic semiconductor film, and polymer using the same
KR101931863B1 (ko) 박막 트랜지스터
JP6689393B2 (ja) 有機半導体膜形成用組成物、有機半導体膜及びその製造方法、並びに、有機半導体素子
WO2015170577A1 (ja) 半導体素子及び絶縁層形成用組成物
KR20150125687A (ko) 유기 박막 트랜지스터, 유기 반도체 박막 및 유기 반도체 재료
WO2021060042A1 (ja) 化合物、組成物、膜、構造体及び電子デバイス
KR101879524B1 (ko) 반도체 소자 및 절연층 형성용 조성물
WO2018003701A1 (ja) 有機薄膜トランジスタ、有機半導体膜、化合物、有機薄膜トランジスタ用組成物及び有機薄膜トランジスタの製造方法
JP6110802B2 (ja) 薄膜トランジスタ
JP6034326B2 (ja) 半導体素子及び絶縁層形成用組成物
JP6754126B2 (ja) 有機半導体素子、有機半導体組成物、有機半導体膜の製造方法、有機半導体膜、並びに、これらに用いる化合物及びポリマー
JP6709275B2 (ja) 有機半導体膜、有機半導体素子、重合体及び有機半導体組成物
JP2017178911A (ja) 含窒素複素環アルケニル化合物、有機半導体材料及び有機半導体デバイス
WO2015008753A1 (ja) 有機膜トランジスタ、有機半導体膜、有機半導体材料およびそれらの応用
JP7266697B2 (ja) 有機薄膜トランジスタ、ポリマー、組成物、有機半導体膜、化合物
TWI623582B (zh) 有機膜電晶體、有機膜電晶體用化合物及其應用
JP6174404B2 (ja) 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
JPWO2017057747A1 (ja) 有機半導体膜形成用組成物、化合物、有機半導体膜、有機半導体素子
JP2023130000A (ja) 高分子化合物及びその製造方法、並びにそれを用いた有機薄膜太陽電池及び有機トランジスタ
WO2020218293A1 (ja) 組成物
JP2015023188A (ja) 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20869091

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021548811

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20869091

Country of ref document: EP

Kind code of ref document: A1