Thiophene compound having sulfonyl group and process for producing the same

A sulfonylthiophene polymer compound represented by the following formula [25]:

• wherein R3 and R3′ each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W, or R3 and R3′ are fused together to represent an alkylene group which has 1 to 3 carbon atoms and may be substituted by W, phenylene group which may be substituted by W, or —(CH2)q-SO2—(CH2)q-SO2—(CH2)q- in which q stands for an integer of from 1 to 3,
• R5 and R6 each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W,
• R4 and R7 each independently represent a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W,
• W represents a halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, diphenylamino group which may be substituted by W′, dinaphthylamino group which may be substituted by W′, dianthranylamino group which may be substituted by W′, N-phenyl-N-naphthylamino group which may be substituted by W′, N-phenyl-N-anthranylamino group which may be substituted by W′, N-naphthyl-N-anthranylamino group which may be substituted by W′, trialkylsilyl group having 1 to 10 carbon atoms, alkylcarbonyl group having 1 to 10 carbon atoms, alkoxycarbonyl group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W′,
• W′ represents an alky group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, or alkoxy group having 1 to 10 carbon atoms,
• m″, n″ and o″ each independently stand for 0 or an integer of 1 or greater, p′ stands for 0 or an integer of 1 or greater, and m″, n″, o″ and p′ satisfy m″+n″+o″≧1 and 50<m″+n″+o″+p′<5,000,
• Z is at least one divalent organic group selected from the following formulas [3] to [11]:
• wherein R8 to R30 each independently represent a hydrogen atom, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W, W has the same meaning as defined above, R31 represents a hydrogen atom, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W′, and W′ has the same meaning as defined above, and
• Y1 and Y2 each independently represent at least one monovalent organic group selected from the following formulas [12] to [15]:
• wherein R3 to R7 and Z have the same meanings as defined above, Q are both end groups of said sulfonyithiophene oligomer compound and each independently represent a hydrogen atom, halogen atom, cyano group, phenyl group which may be substituted by W, naphthyl group which may be substituted by W, anthranyl group which may be substituted by W, hydroxyl group, amino group, formyl group, carboxyl group, dihydroxyboryl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, trialkylstannyl group having 1 to 10 carbon atoms, trialkylsilyl group having 1 to 10 carbon atoms, or dialkoxyboryl group having 1 to 10 carbon atoms, and W has the same meaning as defined above.

A sulfonylthiophene oligomer compound represented by the following formula [16]:

• wherein R3 and R3′ each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W, or R3 and R3′ are fused together to represent an alkylene group which has 1 to 3 carbon atoms and may be substituted by W, phenylene group which may be substituted by W, or —(CH2)q-SO2—(CH2)q-SO2—(CH2)q- in which q stands for an integer of from 1 to 3,
• R5 and R6 each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W,
• R4 and R7 each independently represent a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W,
• W represents a halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, diphenylamino group which may be substituted by W′, dinaphthylamino group which may be substituted by W′, dianthranylamino group which may be substituted by W′, N-phenyl-N-naphthylamino group which may be substituted by W′, N-phenyl-N-anthranylamino group which may be substituted by W′, N-naphthyl-N-anthranylamino group which may be substituted by W′, trialkylsilyl group having 1 to 10 carbon atoms, alkylcarbonyl group having 1 to 10 carbon atoms, alkoxycarbonyl group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W′,
• W′ represents an alky group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, or alkoxy group having 1 to 10 carbon atoms, and
• m′ stands for an integer of 1 or greater, n′ and o′ each independently stand for 0 or an integer of 1 or greater, and m′, n′ and o′ satisfy 2≦m′+n′+o′≦50,
• with a proviso that both ends of said sulfonylthiophene oligomer compound each independently represent a hydrogen atom, halogen atom, cyano group, phenyl group which may be substituted by W, naphthyl group which may be substituted by W, anthranyl group which may be substituted by W, hydroxyl group, amino group, formyl group, carboxyl group, dihydroxyboryl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, trialkylstannyl group having 1 to 10 carbon atoms, trialkylsilyl group having 1 to 10 carbon atoms, or dialkoxyboryl group having 1 to 10 carbon atoms, and W has the same meaning as defined above.

A sulfonylthiophene polymer compound represented by the following formula [26]:

• wherein R3 and R3′ each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W, or R3 and R3′ are fused together to represent an alkylene group which has 1 to 3 carbon atoms and may be substituted by W, phenylene group which may be substituted by W, or
• —(CH2)q-SO2—(CH2)q-SO2—(CH2)q- in which q stands for an integer of from 1 to 3,
• R5 and R6 each independently represent an alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, phenyl group which may be substituted by W, or thienyl group which may be substituted by W,
• R4 and R7 each independently represent a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W,
• W represents a halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, formyl group, carboxyl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 10 carbon atoms, alkynyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, diphenylamino group which may be substituted by W′, dinaphthylamino group which may be substituted by W′, dianthranylamino group which may be substituted by W′, N-phenyl-N-naphthylamino group which may be substituted by W′, N-phenyl-N-anthranylamino group which may be substituted by W′, N-naphthyl-N-anthranylamino group which may be substituted by W′, trialkylsilyl group having 1 to 10 carbon atoms, alkylcarbonyl group having 1 to 10 carbon atoms, alkoxycarbonyl group having 1 to 10 carbon atoms, or phenyl group which may be substituted by W′,
• W′ represents an alky group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, or alkoxy group having 1 to 10 carbon atoms, and
• m′″, n′″ and o′″ each independently stand for 0 or an integer of 1 or greater, and n′″, and o′″ satisfy 50<m′″+n′″+o″<5,000,
• with a proviso that both end groups of said sulfonylthiophene polymer compound each independently represent a hydrogen atom, halogen atom, cyano group, phenyl group which may be substituted by W, naphthyl group which may be substituted by W, anthranyl group which may be substituted by W, hydroxyl group, amino group, formyl group, carboxyl group, dihydroxyboryl group, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, monoalkylamino group having 1 to 10 carbon atoms, dialkylamino group having 1 to 10 carbon atoms, trialkylstannyl group having 1 to 10 carbon atoms, trialkylsilyl group having 1 to 10 carbon atoms, or dialkoxyboryl group having 1 to 10 carbon atoms, and W has the same meaning as defined above.