Conjugated polymer and semiconductor devices including the same

1. A conjugated polymer comprising a repeating unit comprising structure (I):

wherein each R 1 at each occurrence is independently chosen from —R 2 , —H, —OH, —OR 2 , —NR 2 2 and halide, wherein R 2 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl, and each A at each occurrence is independently chosen from N, S, and O, wherein one 5-membered ring in structure (I) independently at each occurrence has one A that is N and one A that is S or O and the other 5-membered ring in structure (I) independently at each occurrence has one A that is N and one A that is O.

2. The polymer of claim 1 , wherein structure (I) is

3. The polymer of claim 1 , wherein each R 1 at each occurrence is independently substituted or unsubstituted C 1-30 alkyl.

4. The polymer of claim 1 , wherein the benzene ring of structure (I) in each repetition of the repeating unit in the polymer is conjugated together.

5. The polymer of claim 1 , wherein the polymer comprises a polymer backbone, wherein the polymer backbone comprises a conjugated system including the benzene ring of structure (I).

6. The polymer of claim 1 , wherein the repeating unit comprises structure (II)

wherein M 1 and M 2 are each independently at each occurrence chosen from a bond and

wherein each of D 1 and D 2 at each occurrence are independently chosen from a bond, substituted or unsubstituted ethenylene, and ethynylene, each Ar at each occurrence is independently chosen from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl, each m at each occurrence is 0 to 30, and at least one of M 1 and M 2 is not a bond.

7. The polymer of claim 6 , wherein M 2 is a bond.

8. The polymer of claim 6 , wherein m is 1.

9. The polymer of claim 6 , wherein Ar at each occurrence is independently chosen from

wherein A 1 at each occurrence is independently chosen from N—R 3 , CR 3 2 , SiR 3 2 , S, and O,

each R 3 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl,

each R 4 at each occurrence is independently chosen from —H, —R 3 , —OR 3 , —NR 3 2 , and halide,

p at each occurrence is independently chosen from 0, 1, and 2,

r at each occurrence is independently chosen from 0, 1, 2, 3, and 4,

q at each occurrence is independently chosen from 0, 1, 2, and 3, and

s at each occurrence is independently chosen from 0 and 1.

10. The polymer of claim 9 , wherein Ar at each occurrence is independently chosen from

11. The polymer of claim 9 , wherein R 3 is at each occurrence independently C 1-15 hydrocarbyl.

12. The polymer of claim 9 , wherein the polymer comprises the structure

wherein Ar at each occurrence is independently chosen from

13. The polymer of claim 1 , wherein the polymer is terminated by end groups -E wherein each -E at each occurrence is independently chosen from substituted or unsubstituted —R 5 , —H, —OH, —OR 5 , —NR 5 2 and halide, wherein R 5 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl.

14. The polymer of claim 1 , wherein -E at each occurrence is independently C 1-15 aryl and heteroaryl.

15. The polymer of claim 6 , wherein the polymer is structure (II)

wherein n is about 2 to about 10,000, and end groups E 1 and E 2 are each independently at each occurrence chosen from substituted or unsubstituted —R 5 , —H, —OH, —OR 5 , —NR 5 2 and halide, wherein R 5 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl.

16. The polymer of claim 1 , wherein the polymer has the structure

wherein Ar at each occurrence is independently chosen from

wherein each R 3 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl, and n is about 2 to about 10,000.

17. A semiconductor device comprising the polymer of claim 1 .

18. The semiconductor device of claim 17 , wherein the semiconductor device comprises at least one of a transistor, a diode, a photovoltaic cell, an integrated circuit, or an optoelectronic device.

19. The polymer of claim 1 , wherein the polymer has the structure

wherein each A at each occurrence is independently chosen from N, S, and O, wherein one 5-membered ring in the fused benzene ring system independently at each occurrence has one A that is N and one A that is S or O and the other 5-membered ring in the fused benzene ring system independently at each occurrence has one A that is N and one A that is O, and M 1 and M 2 are each independently at each occurrence chosen from a bond and

wherein each of D 1 and D 2 at each occurrence are independently chosen from a bond, substituted or unsubstituted ethenylene, and ethynylene, each m at each occurrence is 0 to 30, and at least one of M 1 and M 2 is not a bond,

wherein Ar at each occurrence is independently chosen from

wherein A 1 at each occurrence is independently chosen from N—R 3 , CR 3 2 , SiR 3 2 , S, and O,

wherein each R 3 at each occurrence is independently chosen from —H and C 1-15 hydrocarbyl, and

wherein n is about 2 to about 10,000, and E 1 and E 2 are each independently at each occurrence chosen from substituted or unsubstituted —R 5 , —H, —OH, —OR 5 , —NR 5 2 and halide, wherein R 5 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl.

20. A method of making a polymer, comprising:

obtaining or providing a fused benzene ring system having the structure

wherein each A at each occurrence is independently chosen from N, S, and O, wherein one 5-membered ring in structure (III) independently at each occurrence has one A that is N and one A that is S or O and the other 5-membered ring in structure (III) independently at each occurrence has one A that is N and one A that is O,

each R 1 at each occurrence is independently chosen from —R 2 , —H, —OH, —OR 2 , —NR 2 2 and halide, wherein R 2 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl, and X is —I, —Br, —Cl, or —F, and

each R 6 at each occurrence is independently a bond or Ar, wherein each Ar at each occurrence is independently chosen from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

obtaining or providing a conjugated linker having the structure

wherein each L at each occurrence is —Sn(R 7 ) 3 or —B(OR 8 ) 2 , wherein R 7 at each occurrence is independently C 1-15 hydrocarbyl, wherein R 8 is C 1-30 hydrocarbyl or together with another R 8 is a C 2-30 hydrocarbylene that forms a cyclic boronic acid ester structure with the —B(O—) 2 , and each m at each occurrence is 0 to 30; and

contacting the fused benzene ring system and the conjugated linker under conditions so as to provide a conjugated polymer having a repeating unit comprising structure (II)

wherein M 1 and M 2 are each independently at each occurrence chosen from a bond and

wherein each of D 1 and D 2 at each occurrence are independently chosen from a bond and ethynylene, and at least one of M 1 and M 2 is not a bond.

21. A conjugated polymer having the formula

wherein each R 1 at each occurrence is independently chosen from —R 2 , —H, —OH, —OR 2 , —NR 2 2 and halide, wherein R 2 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl, and each A at each occurrence is independently chosen from N, S, and O, wherein one 5-membered ring independently at each occurrence has one A that is N and one A that is S or O and the other 5-membered ring independently at each occurrence has one A that is N and one A that is O and M 1 and M 2 are each independently at each occurrence chosen from a bond and

wherein each of D 1 and D 2 at each occurrence are independently chosen from a bond, substituted or unsubstituted ethenylene, and ethynylene, each m at each occurrence is 0 to 30, and at least one of M 1 and M 2 is not a bond,

wherein Ar at each occurrence is independently chosen from

wherein A 1 at each occurrence is independently chosen from N—R 3 , CR 3 2 , SiR 3 2 , S, and O,

wherein each R 3 at each occurrence is independently chosen from —H and C 1-15 hydrocarbyl, and

wherein each R 9 at each occurrence is independently chosen from —H, C 1-8 straight chain alkyl, dodecyl, C 1-15 branched alkyl, and C 1-15 cyclic hydrocarbon,

wherein n is about 2 to about 10,000, and E 1 and E 2 are each independently at each occurrence chosen from substituted or unsubstituted —R 5 , —H, —OH, —OR 5 , —NR 5 2 , and halide, wherein R 5 at each occurrence is independently chosen from —H and substituted or unsubstituted C 1-60 hydrocarbyl.