Conjugated heteroaromatic homopolymer and copolymer, and applications thereof
AssigneePolyM technology corporation
InventorsChien-Chung Han, Balasubramanian Arumugam
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Abstract
A method for forming a conjugated heteroaromatic polymer is described, wherein at least one compound of formula (1) is polymerized using an acid as a catalyst, wherein X is selected from S, O, Se, Te, PR2 and NR2, Y is hydrogen (H) or a precursor of a good leaving group Y− whose conjugate acid (HY) has a pKa of less than 30, Z is hydrogen (H), silyl, or a good leaving group whose conjugate acid (HY) has a pKa of less than 30, b is 0, 1 or 2, each R1 is a substituent, and the at least one compound of formula (1) being polymerized includes at least one compound of formula (1) with Z═H and Y≠H.
Claims17
A conjugated heteroaromatic polymer, which
- i) is prepared from a method comprising polymerizing at least one compound of formula (2) using an acid as a catalyst,
- wherein
- X is the same or different at each occurrence, and is independently selected from the group consisting of S, O, Se, Te, PR2 and NR2, wherein R2 is selected from the group consisting of hydrogen, and substituted and unsubstituted alkyl, aryl, heteroaryl, alkanoyl, and aryloy groups;
- Y is hydrogen (H), or a precursor of a good leaving group Y− whose conjugate acid (HY) has a pKa of less than 30;
- Z is hydrogen (H), silyl, or a precursor of a good leaving group Z− whose conjugate acid (HZ) has a pKa of less than 30;
- Ar is a substituted or unsubstituted, mono- or poly-nuclear, aryl or heteroaryl ring;
- m, o and p are each independently an integer equal to or greater than 0, with a proviso that m+p≥1;
- each k is independently 0, 1 or 2;
- each R5 is a substituent, wherein any two R5 on the same ring or on two neighboring rings, or R5 and a substituent group on a neighboring Ar ring, may join together to form another ring;
- the at least one compound of formula (2) being polymerized comprises at least one compound of formula (2) with Z═H and Y≠H that triggers the polymerization;
- the acid as the catalyst is selected from Lewis acids, polymeric acids, and protic acids other than HBr and HCl;
- a polymerization degree of the conjugated heteroaromatic polymer is at least 4;
- the acid as the catalyst initiates the polymerization;
- and
- the at least one compound of formula (2) is polymerized at 2- and 5-positions thereof,
- ii) contains at least a leaving group Y at a chain end thereof,
- iii) is transition-metal free, and
- (iv) contains, as a dopant therefor, the acid as the catalyst.
A conjugated heteroaromatic multi-block copolymer, which is prepared from a method comprising polymerizing at least one compound of formula (1) using an acid as a catalyst, and is transition-metal free,
- wherein
- X is selected from the group consisting of S, O, Se, Te, PR2 and NR2, wherein R2 is selected from the group consisting of hydrogen, and substituted and unsubstituted alkyl, aryl, heteroaryl, alkanoyl, and aryloyl groups;
- Y is hydrogen (H), or a precursor of a good leaving group Y− whose conjugate acid (HY) has a pKa of less than 30;
- Z is hydrogen (H), silyl, or a precursor of a good leaving group Z− whose conjugate acid (HZ) has a pKa of less than 30;
- b is 0, 1 or 2;
- each R1 is a substituent, wherein when b=2, the two R1 are the same or different and may joint together to form a ring;
- the at least one compound of formula (1) being polymerized comprises at least one compound of formula (1) with Z═H and Y≠H that triggers the polymerization, and one or more other compounds of formula (1) that contain one or more different combination sets of X, R1 and b;
- the acid as the catalyst is selected from Lewis acids, polymeric acids, and protic acids other than HBr and HCl;
- a polymerization degree of the conjugated heteroaromatic polymer is at least 4;
- the acid as the catalyst initiates the polymerization;
- the at least one compound of formula (1) is polymerized at 2- and 5-positions thereof;
- the at least one compound of formula (1) with Z═H and Y≠H is polymerized first to form a polymer chain, and then the one or more other compounds of formula (1) are added in a sequence to react with a terminal of the polymer chain and elongate the polymer chain to form one or more different polymer blocks;
- and
- the conjugated heteroaromatic multi-block copolymer contains, as a dopant therefor, the acid as the catalyst.
A conjugated heteroaromatic block copolymer, comprising a fragment expressed by formula (3), being transition-metal free, and being prepared through a polymerization using an acid catalyst:
- wherein
- n is an integer equal to or greater than 1;
- m1, m2, m3 are independently integral equal to or greater than 2;
- n1, n2, n3 are independently 1 or 0;
- X1, X2, and X3 are the same or different and are independently selected from the group consisting of S, O, Se, Te, PR2 and NR2, wherein R2 is selected from the group consisting of hydrogen, and substituted and unsubstituted alkyl, aryl, heteroaryl, alkanoyl, and aryloy groups;
- k1, k2, k3 are independently 0, 1 or 2;
- and
- R6, R7, and R8 are the same or different substituents, wherein any two R6 or two R7 or two R8 groups on the same ring may join together to form another ring,
- with a proviso that any two neighboring blocks have different repeat units, and
- wherein the conjugated heteroaromatic block copolymer contains, as a dopant therefor, the acid catalyst.
Dependencies are inferred from the claim text.