US 12,331,062 B2Granted

Compound, production method therefor, and organic semiconductor material obtained using said compound

AssigneesOsaka University, Ishihara Sangyo Kaisha, Ltd.

InventorsYutaka Ie, Takuji Seo, Shreyam Chatterjee, Taichi Moriyama, Syun Kudo

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Abstract

Provided are a compound having an excellent semiconductor property and a method for producing the compound, an intermediate of the compound and a method for producing the intermediate, and an organic semiconductor material and an organic semiconductor device each obtained with use of the organic semiconductor material. A compound represented by general formula (2): where: A1 and A2 are CM1 or N, and M1 is H or the like; J1 and J2 are each independently a skeleton giving an electron donating property or an electron accepting property; and X1 and X2 are where: M2 to M4 are H or the like, and M3 and M4 may be bonded to each other to form a ring.

Claims7

Dependent claims

A compound represented by a general formula (1):

where:
in the general formula (1),
A1 and A2 are each independently CM1 or N, and M1 is a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, a cyano group, an alkoxy group optionally substituted with Z, an alkylthio group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl carbonyl group optionally substituted with Z, or an aryl group optionally substituted with Z;
Q1 and Q2 are each independently a hydrogen atom, a halogen atom, an aryl group optionally substituted with Z, a heterocyclic group optionally substituted with Z, a formyl group, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate ester group, a trifluoroborate salt group, a triolborate salt group, a trialkylsilyl group, or a trialkylstannyl group;
X1 and X2 are each independently
where:
M2 to M4 are each independently a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, an alkoxy group optionally substituted with Z, an alkyl ester group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl amino carbonyl group optionally substituted with Z, an acyl group optionally substituted with Z, an amino group optionally substituted with Z, an acylamino group optionally substituted with Z, an aryloxy group optionally substituted with Z, an aryloxycarbonyl group optionally substituted with Z, an acyloxy group optionally substituted with Z, an alkoxycarbonylamino group optionally substituted with Z, an aryloxycarbonylamino group optionally substituted with Z, an alkylthio group optionally substituted with Z, an arylthio group optionally substituted with Z, an aryl group optionally substituted with Z, or a heterocyclic group optionally substituted with Z, and M3 and M4 optionally form a ring together;
and
Z is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group, an alkoxy carbonyl group, an amino group, an alkoxy group, a cycloalkyloxy group, an aryloxy group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonyl amino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a silyl group, a sulfonyl group, a sulfinyl group, an ureide group, a phosphoric acid amido group, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, or an imino group.

6 more elements

A compound represented by a general formula (2-1):

where:
in the general formula (2-1),
A1 and A2 are each independently CM1 or N, and M1 is a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, a cyano group, an alkoxy group optionally substituted with Z, an alkylthio group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl carbonyl group optionally substituted with Z, or an aryl group optionally substituted with Z;
X1 and X2 are each independently
where:
M2 to M4 are each independently a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, an alkoxy group optionally substituted with Z, an alkyl ester group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl amino carbonyl group optionally substituted with Z, an acyl group optionally substituted with Z, an amino group optionally substituted with Z, an acylamino group optionally substituted with Z, an aryloxy group optionally substituted with Z, an aryloxycarbonyl group optionally substituted with Z, an acyloxy group optionally substituted with Z, an alkoxycarbonylamino group optionally substituted with Z, an aryloxycarbonylamino group optionally substituted with Z, an alkylthio group optionally substituted with Z, an arylthio group optionally substituted with Z, an aryl group optionally substituted with Z, or a heterocyclic group optionally substituted with Z, and M3 and M4 optionally form a ring together;
and
Z is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group, an alkoxy carbonyl group, an amino group, an alkoxy group, a cycloalkyloxy group, an aryloxy group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonyl amino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a silyl group, a sulfonyl group, a sulfinyl group, an ureide group, a phosphoric acid amido group, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, or an imino group,
D1, D2, G1, and G2 are each independently CM1 or N;
m and n are each independently 0 or a natural number;
T1 and T2 are each independently
where R1 to R9 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxy carbonyl group, an alkyl carbonyl group, or an aryl group;
and * represents a bond.

10 more elements

A method for producing a compound represented by a general formula (1):

where:
in the general formula (1),
A1 and A2 are each independently CM1 or N, and M1 is a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, a cyano group, an alkoxy group optionally substituted with Z, an alkylthio group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl carbonyl group optionally substituted with Z, or an aryl group optionally substituted with Z;
Q1 and Q2 are each independently a hydrogen atom, a halogen atom, an aryl group optionally substituted with Z, a heterocyclic group optionally substituted with Z, a formyl group, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate ester group, a trifluoroborate salt group, a triolborate salt group, a trialkylsilyl group, or a trialkylstannyl group;
X1 and X2 are each independently
where:
M2 to M4 are each independently a hydrogen atom, a halogen atom, an alkyl group optionally substituted with Z, an alkoxy group optionally substituted with Z, an alkyl ester group optionally substituted with Z, an alkoxy carbonyl group optionally substituted with Z, an alkyl amino carbonyl group optionally substituted with Z, an acyl group optionally substituted with Z, an amino group optionally substituted with Z, an acylamino group optionally substituted with Z, an aryloxy group optionally substituted with Z, an aryloxycarbonyl group optionally substituted with Z, an acyloxy group optionally substituted with Z, an alkoxycarbonylamino group optionally substituted with Z, an aryloxycarbonylamino group optionally substituted with Z, an alkylthio group optionally substituted with Z, an arylthio group optionally substituted with Z, an aryl group optionally substituted with Z, or a heterocyclic group optionally substituted with Z, and M3 and M4 optionally form a ring together;
and
Z is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group, an alkoxy carbonyl group, an amino group, an alkoxy group, a cycloalkyloxy group, an aryloxy group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonyl amino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a silyl group, a sulfonyl group, a sulfinyl group, an ureide group, a phosphoric acid amido group, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, or an imino group,
said method being any of the following method (1), (2), (3), (4), (5), or (6):
the method (1) including:
(i) a step 1a of causing a compound represented by a general formula (A5) to react with trialkylsilylacetylene to produce a compound represented by a general formula (A6):
where, in the general formula (A5), each Hal is independently a halogen atom;
and X1 and X2 are the same as those defined above,
where, in the general formula (A6);
TAS represents a trialkylsilyl group;
and X1 and X2 are the same as those defined above;
(ii) a step 2a of causing the compound represented by the general formula (A6) obtained in the step 1a to react with a sulphurizing agent to produce a compound represented by a general formula (A7):
where, in the general formula (A7), TAS, X1, and X2 are the same as those defined above;
and R10 and R11 are each independently an alkyl group optionally substituted with Z, and Z is the same as that defined above;
and
(iii) a step 3a of causing the compound represented by the general formula (A7) obtained in the step 2a to react with a halogenating agent to produce a compound represented by a general formula (1-1):
where, in the general formula (1-1), TAS, Hal, X1, and X2 are the same as those defined above,
the general formula (1-1) being encompassed in the general formula (1);
the method (2) including:
a step 4a of causing the compound represented by the general formula (1-1) obtained in the step 3a to react with a boron compound to produce a compound represented by a general formula (1-2):
where, in the general formula (1-2), TAS, M1, X1, and X2 are the same as those defined above,
the general formula (1-2) being encompassed in the general formula (1);
the method (3) including:
a step 5a of causing the compound represented by the general formula (1-2) obtained in the step 4a to react with a halogenating agent to produce a compound represented by a general formula (1-3):
where, in the general formula (1-3), M1, X1, and X2 are the same as those defined above;
and Q1a and Q2a are each independently a halogen atom,
the general formula (1-3) being encompassed in the general formula (1);
the method (4) including:
a step 6a of causing the compound represented by the general formula (1-3) to react with a boron compound or a tin compound to produce a compound represented by a general formula (1-4):
where, in the general formula (1-4), M1, X1, and X2 are the same as those defined above;
and Q1b and Q2b are each independently a hydrogen atom, an aryl group optionally substituted with Z, a heterocyclic group optionally substituted with Z, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate ester group, a trifluoroborate salt group, a triolborate salt group, a trialkylsilyl group, or a trialkylstannyl group,
the general formula (1-4) being encompassed in the general formula (1);
the method (5) including:
formylating the compound represented by the general formula (1-4) to produce a compound represented by a general formula (1-5):
where, in the general formula (1-5), M1, X1, and X2 are the same as those defined above;
and Q1c and Q2c are each independently a formyl group;
the method (6) including:
(i) a step 1b of causing a compound represented by a general formula (A9) to react with a halogenating agent to produce a compound represented by a general formula (A10):
where, in the general formula (A9), X1 and X2 are the same as those defined above;
where, in the general formula (A10), X1, X2, and Hal are the same as those defined above;
(ii) a step 2b of causing the compound represented by the general formula (A10) obtained in the step 1b to react with an aminating agent to produce a compound represented by a general formula (A11):
where, in the general formula (A11), X1 and X2 are the same as those defined above;
(iii) a step 3b of causing the compound represented by the general formula (A11) obtained in the step 2b to react with a compound represented by Q1-CO2Cl, where Q1 is the same as that defined above, and a compound represented by Q2-CO2Cl, where Q2 is the same as that defined above, to produce a compound represented by a general formula (A12):
where, in the general formula (A12), X1, X2, Q1, and Q2 are the same as those defined above;
and
(iv) a step 4b of causing the compound represented by the general formula (A12) obtained in the step 3b to react with a sulphurizing agent to produce a compound represented by a general formula (1-6):
where, in the general formula (1-6), X1, X2, Q1, and Q2 are the same as those defined above,
the general formula (1-6) being encompassed in the general formula (1).

51 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/288,949Filed 25 Oct 2019
Priority: JP 2018-20373530 Oct 2018
Published: US 2021/0399228 A123 Dec 2021
Granted: 17 Jun 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 513/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero…
C07D 495/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms: in which the…
C07D 498/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 517/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero…