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US 7,901,594 B2Granted
Polyacene derivatives and production thereof
AssigneeJapan Science and Technology Corporation
InventorTamotsu Takahasi
Life of this patent
Estimating the term…
Abstract
The present invention relates to polyacene derivatives represented by general formula (I) below: (wherein R1 to R10, etc. each represents hydrogen atom, hydrocarbon group, or an alkoxy group; A1 and A2 are hydrogen atom, a halogen atom, a hydrocarbon group, an alkoxy group, cyano group, etc.; n is an integer of not less than 1; R6 and R7 may be linked to each other to form a ring); and a process for preparing the polyacene derivatives from polyhydro compounds as well as electrically conductive materials comprising the polyacene derivatives. According to the process for preparing the polyacene derivatives of the present invention, optional substituents can be introduced into any carbon atoms of the polyacene, and the number of aromatic rings can be increased.
Claims40
A polyacene derivative represented by general formula (I) below:
- wherein each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
- —N(R11)— wherein R11 is hydrogen atom or a hydrocarbon group, or may optionally be substituted;
- each of R1 and R2, which may be the same or different, independently represents a C1-C40 alkyl group which may optionally be substituted, or a C6-C18 aryl group which may optionally be substituted;
- each of R4 and R9, which may be the same or different, independently represents a C1-C40 alkyl group, or a C6-C18 aryl group which may optionally be substituted;
- each of A1 and A2, which may be the same or different, independently represents a C2-C40 alkoxycarbonyl group which may optionally be substituted;
- n is 1;
- with proviso that the case of (b) below is excluded:
- (b) R3, R4, R9 and R10 are all aryl groups that may optionally be substituted.
12 more elements
A polyacene derivative represented by general formula (I) below:
- wherein each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
- —N(R1)— wherein R11 is hydrogen atom or a hydrocarbon group, or may optionally be substituted;
- each of A1, A2, R1 and R2, which may be the same or different, independently represents a C1-C40 alkyl group which may optionally be substituted, or a C6-C18 aryl group which may optionally be substituted;
- each of R4 and R9, which may be the same or different, independently represents a C1-C40 alkyl group, or a C6-C18 aryl group which may optionally be substituted;
- n is 1;
- with proviso that the cases of (a) and (b) below are excluded:
- (a) R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, A1 and A2 are all methyl groups;
- and
- (b) R3, R4, R9 and R10 are all aryl groups that may optionally be substituted.
13 more elements
A polyacene derivative represented by general formula (I) below:
- wherein each of R1 and R2, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- each of R4 and R9, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 alkyl group, a C2-C40 alkenyl group which may optionally be substituted, a C2-C40 alkynyl group which may optionally be substituted, a C3-C40 allyl group group which may optionally be substituted, a C4-C40 alkyldienyl group which may optionally be substituted, a C4-C40 polyenyl group which may optionally be substituted, a C6-C18 aryl group which may optionally be substituted, a C6-C40 alkylaryl group which may optionally be substituted, a C6-C40 arylalkyl group which may optionally be substituted, a C4-C40 cycloalkyl group, a C4-C40 cycloalkenyl group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents a C1-C40 alkyl group which may optionally be substituted, or a C6-C18 aryl group which may optionally be substituted;
- each of A1 and A2, which may be the same or different, independently represents a halogen atom;
- n is 1
- with a proviso that R3, R4, R9 and R10 may not all be aryl groups.
15 more elements
A polyacene derivative represented by formula (Ia) below:
- wherein:
- A1 and A2 are a C2-C40 alkoxycarbonyl group which may optionally be substituted,
- R1, R2, R5b, R6, R7, and R8b are a C1-C40 alkyl group which may optionally be substituted;
- R4 and R9 are a C1-C40 alkyl group;
- each of R3, R5a, R8a and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
- —N(R11)— wherein R11 is hydrogen atom or a hydrocarbon group, or may optionally be substituted;
- and
- provided that the cases of (a′) and (b′) below are excluded:
- (a′) at least one of R3, R5a, R8a, and R10 is a diarylamine group;
- and
- (b′) R3 and R10 are both aryl groups which may optionally be substituted, or R5a and R8a are both aryl groups which may optionally be substituted.
15 more elements
A polyacene derivative represented by the formula (Ia),
- wherein:
- A1 and A2 are a halogen atom;
- R3, R5a, R8a and R10 are a C1-C40 alkyl group which may optionally be substituted;
- each of R1, R2, R5b, R6, R7 and R8b, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 alkyl group which may optionally be substituted;
- a C2-C40 alkenyl group which may optionally be substituted;
- a C2-C40 alkynyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring;
- and
- each of R4 and R9, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 alkyl group, a C2-C40 alkenyl group which may optionally be substituted, a C2-C40 alkynyl group which may optionally be substituted.
8 more elements
A process of producing the polyacene derivative represented by formula (I) below:
- wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
- —N(R11)— wherein R11 is hydrogen atom or a hydrocarbon group, or may optionally be substituted;
- each of A1 and A2, which may be the same or different, independently represents hydrogen atom;
- a halogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- a C7-C40 alkylaryloxy group which may optionally be substituted;
- a C2-C40 alkoxycarbonyl group which may optionally be substituted;
- a C7-C40 aryloxycarbonyl group which may optionally be substituted;
- cyano group —CN;
- carbamoyl group —C(═O)NH2;
- a haloformyl group —C(═O)—X, wherein X represents a halogen atom;
- formyl group —C(═O)—H;
- isocyano group;
- isocyanate group;
- thiocyanate group or thioisocyanate group;
- provided that A1 and A2 may be cross-bridged with each other to form a ring shown by formula:
- —C(═O)—B—C(═O)— wherein B is oxygen atom or a group shown by formula —N(B1)— wherein B1 is hydrogen atom, a C1-C40 hydrocarbon group or a halogen atom;
- and,
- n is 1 or 2,
- which comprises aromatizing hydrocarbon condensed rings represented by formula (II) below:
- wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, A1, A2 and n have the same significance as defined above;
- the bond shown by formula below represents a single bond or a double bond;
- provided that when the bond is a single bond, hydrogen atom is further bound directly to the carbon atoms which are directly bound to R5, R6, R7 and R8;
- in the presence of a dehydrogenation reagent comprising a combination of an alkyl lithium and an alkyl halide.
30 more elements
A polyacene derivative represented by general formula (I) below:
- wherein:
- each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group;
- a C1-C40 alkoxy group;
- a C6-C40 aryloxy group;
- an amino group;
- a hydroxy group;
- or a silyl group;
- each of R1, R2, R4 and R9, which may be the same or different, independently represents a C1-C40 alkyl group, or a C6-C18 aryl group;
- each of A1 and A2, which may be the same or different, independently represents a C2-C40 alkoxycarbonyl group;
- and
- n is 1;
- with proviso that the case of (b) below is excluded:
- (b) R3, R4, R9 and R10 are all aryl groups that may optionally be substituted.
11 more elements
A polyacene derivative represented by general formula (I) below:
- wherein:
- each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group;
- a C1-C40 alkoxy group;
- a C6-C40 aryloxy group;
- an amino group;
- a hydroxy group;
- or a silyl group;
- each of A1, A2, R1, R2, R4 and R9, which may be the same or different, independently represents a C1-C40 alkyl group, or a C6-C18 aryl group;
- and
- n is 1;
- with proviso that the cases of (a) and (b) below are excluded:
- (a) R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, A1 and A2 are all methyl groups;
- and
- (b) R3, R4, R9 and R10 are all aryl groups that may optionally be substituted.
12 more elements
A polyacene derivative represented by general formula (I) below:
- wherein:
- each of R1, R2, R4 and R9, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group;
- a C1-C40 alkoxy group;
- a C6-C40 aryloxy group;
- an amino group;
- a hydroxy group;
- or a silyl group;
- each of R3, R5, R6, R7, R8 and R10, which may be the same or different, independently represents a C1-C40 alkyl group, or a C6-C18 aryl group;
- each of A1 and A2, which may be the same or different, independently represents a halogen atom;
- n is 1;
- with a proviso that R3, R4, R9 and R10 are not all aryl groups.
9 more elements
A polyacene derivative represented by formula (Ia) below:
- A1 and A2 are a C2-C40 alkoxycarbonyl group;
- R1, R2, R4, R5b, R6, R7, R8b and R9 are a C1-C40 alkyl group;
- each of R3, R5a, R8a and R10, which may be the same or different, independently represents hydrogen atom;
- a C1-C40 hydrocarbon group which may optionally be substituted;
- a C1-C40 alkoxy group which may optionally be substituted;
- a C6-C40 aryloxy group which may optionally be substituted;
- an amino group which may optionally be substituted;
- a hydroxy group;
- or a silyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
- —N(R11)— wherein R11 is hydrogen atom or a hydrocarbon group, or may optionally be substituted;
- and
- provided that the cases of (a′) and (b′) below are excluded:
- (a′) at least one of R3, R5a, R8b and R10 is a diarylamine group;
- and
- (b′) R3 and R10 are both aryl groups which may optionally be substituted, or R5a and R8a are both aryl groups which may optionally be substituted.
13 more elements
A polyacene derivative represented by the formula (Ia),
- wherein:
- A1 and A2 are a halogen atom;
- R3, R5a, R8a and R10 are a C1-C40 alkyl group;
- each of R1, R2, R5b, R6, R7, and R8b, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 alkyl group which may optionally be substituted;
- a C2-C40 alkenyl group which may optionally be substituted;
- a C2-C40 alkynyl group which may optionally be substituted;
- provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring;
- and
- each of R4 and R9, which may be the same or different, independently represents a hydrogen atom;
- a C1-C40 alkyl group, a C2-C40 alkenyl group which may optionally be substituted, a C2-C40 alkynyl group which may optionally be substituted.
8 more elements
A polyacene derivative selected from the group consisting of dimethyl 1,4,6,8,9,10,11,13-octapropylpentacene-2,3-dicarboxylate, dimethyl 1,4,6,11-tetrapropylnaphtacene-2,3-dicarbooxylate, dimethyl 1,4,6,8,9,10,11,13-octaethylpentacene-2,3-dicarbooxylate, 5,14-bis(p-bromophenyl)-7,12-dipropyl- 1,2,3,4-tetrahydropentacene, 2,3-diiodo-5,7,8,9,10,12-hexapropylnaphtacene, and 1,2,3,4,6,11-hexapropylnaphtacene.
Dependencies are inferred from the claim text.