Thienothiadiazole compounds and related semiconductor devices

1. A compound comprising one or more moieties represented by formula (I):

wherein X is a chalcogen; and one or more linear conjugated moieties and/or one or more cyclic conjugated moieties other than the moieties represented by formula (I), and

wherein the compound is a polymer having a first repeating unit M 1 selected from the group consisting of:

wherein:

pi-2 is an optionally substituted conjugated polycyclic moiety;

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

Z is a conjugated noncyclic linker;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

p and p′ independently are 0 and 1, provided that at least one of p and p′ is 1; and

the polymer has a degree of polymerization (n) ranging from 3 to 1,000.

2. The compound of claim 1 , wherein the compound comprises one or more moieties represented by formula (II):

wherein R 1 , at each occurrence, independently is selected from the group consisting of H, halogen, —CN, NO 2 , R 2 , -L-R 3 , OH, OR 2 , OR 3 , NH 2 , NHR 2 , N(R 2 ) 2 , NHR 3 , NR 2 R 3 , N(R 3 ) 2 , SH, SR 2 , SR 3 , S(O) 2 OH, —S(O) 2 OR 2 , —S(O) 2 OR 3 , C(O)H, C(O)R 2 , C(O)R 3 , C(O)OH, C(O)OR 2 , C(O)OR 3 , C(O)NH 2 , C(O)NHR 2 , C(O)N(R 2 ) 2 , C(O)NHR 3 , C(O)NR 2 R 3 , C(O)N(R 3 ) 2 , SiH(R 2 ) 2 , SiH 2 (R 2 ), and Si(R 2 ) 3 , wherein L is selected from the group consisting of a divalent C 1-40 alkyl group, a divalent C 2-40 alkenyl group, a divalent C 1-40 haloalkyl group, and a covalent bond; R 2 is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group; and R 3 is selected from the group consisting of a C 3-10 cycloalkyl group, a C 6-14 aryl group, a C 6-14 haloaryl group, a 3-12 membered cycloheteroalkyl group, and a 5-14 membered heteroaryl group, each of which optionally is substituted with 1-5 substituents selected from the group consisting of a halogen, —CN, NO 2 , R 2 , OR 2 , and SR 2 .

3. The compound of claim 1 , wherein X is selected from the group consisting of O, S, and Se.

4. The compound of claim 3 , wherein the compound comprises one or more moieties represented by formula (III) or (IV):

5. The compound of claim 1 , wherein the compound is a polymer having a first repeating unit M 1 selected from the group consisting of:

6. The compound of claim 2 , wherein the compound is a polymer having a first repeating unit M 1 selected from the group consisting of:

wherein:

pi-2 is an optionally substituted conjugated polycyclic moiety;

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

Z is a conjugated noncyclic linker;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

p and p′ independently are 0 and 1, provided that at least one of p and p′ is 1; and

the polymer has a degree of polymerization (n) ranging from 3 to 1,000.

7. The compound of claim 6 , wherein the compound is a polymer having a first repeating unit M 1 selected from the group consisting of:

8. The compound of claim 6 , wherein R 1 , at each occurrence, independently is selected from the group consisting of H, F, Cl, —CN, —NO 2 , R 2 , OR 2 , and SR 2 , wherein R 2 is selected from the group consisting of a linear or branched C 1-40 alkyl group, a linear or branched C 2-40 alkenyl group, and a linear or branched C 1-40 haloalkyl group.

9. The compound of claim 1 further comprising one or more additional repeating units M 2 that are different from the first repeating unit M 1 , said additional repeating units M 2 being selected from the group consisting of:

wherein:

pi-2 is an optionally substituted conjugated polycyclic moiety;

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

Z is a conjugated noncyclic linker;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

m″ is 1, 2, 3, 4, 5 or 6; and

p and p′ independently are 0 and 1, provided that at least one of p and p′ is 1.

10. The compound of claim 9 represented by formula (V) or (VI):

wherein n is an integer ranging from 3 to 1,000.

11. The compound of claim 10 , wherein pi-2 in the first repeating unit M 1 and any additional repeating unit M 2 is an optionally substituted C 8-26 aryl group or 8-26 membered heteroaryl group selected from the group consisting of:

wherein:

R a is selected from the group consisting of H, F, Cl, —CN, R, —OR, —SR, —C(O)R, —OC(O)R, and —C(O)OR;

R b is selected from the group consisting of H, R, and -L′-R f ;

R 0 is H or R;

R d is selected from the group consisting of H, F, Cl, —CN, R, —OR, —SR, —C(O)R, —OC(O)R,

—C(O)OR, and -L′-R f ;

R e is selected from the group consisting of H, F, Cl, —CN, R, —OR, —SR, —C(O)R, —OC(O)R, —C(O)OR, and R f ;

R f is a C 6-20 aryl group or a 5-20-membered heteroaryl group, each optionally substituted with 1-8 groups independently selected from the group consisting of F, Cl, —CN, R, —OR, and —SR;

L′ is selected from the group consisting of —O—, —S—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and

R is selected from the group consisting of a C 1-40 alkyl group, a C 1-40 haloalkyl group, a C 2-40 alkenyl group, and a C 2-40 alkynyl group.

12. The compound of claim 1 , wherein Ar in (Ar) m , (Ar) m′ , and (Ar) m″ in the first repeating unit M 1 and any additional repeating unit M 2 is represented by:

wherein each W independently is selected from the group consisting of N, CH, and CR 4 , wherein R 4 is selected from the group consisting of F, Cl, —CN, R 2 , OR 2 , SR 2 , C(O)R 2 , OC(O)R 2 , and C(O)OR 2 , and wherein R 2 is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.

13. The compound of claim 12 , wherein (Ar) m , (Ar) m′ , and (Ar) m″ if present in either the first repeating unit M 1 or any additional repeating unit M 2 independently are selected from the group consisting of:

14. The compound of claim 1 , wherein each Z if present in either the first repeating unit M 1 or any additional repeating unit M 2 is independently selected from the group consisting of:

wherein R 4 is selected from the group consisting of F, Cl, —CN, R 2 , OR 2 , SR 2 , C(O)R 2 , OC(O)R 2 , and C(O)OR 2 , and wherein R 2 is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.

15. A compound comprising one or more moieties represented by formula (I):

wherein X is a chalcogen; and one or more linear conjugated moieties and/or one or more cyclic conjugated moieties other than the moieties represented by formula (I), wherein the compound is a small molecule represented by formula (VII) or (VIII):

wherein:

R 1 , at each occurrence, independently is selected from the group consisting of H, halogen, —CN, NO 2 , R 2 , -L-R 3 , OH, OR 2 , OR 3 , NH 2 , NHR 2 , N(R 2 ) 2 , NHR 3 , NR 2 R 3 , N(R 3 ) 2 , SH, SR 2 , SR 3 , S(O) 2 OH, —S(O) 2 OR 2 , —S(O) 2 OR 3 , C(O)H, C(O)R 2 , C(O)R 3 , C(O)OH, C(O)OR 2 , C(O)OR 3 , C(O)NH 2 , C(O)NHR 2 , C(O)N(R 2 ) 2 , C(O)NHR 3 , C(O)NR 2 R 3 , C(O)N(R 3 ) 2 , SiH 3 , SiH(R 2 ) 2 , SiH 2 (R 2 ), and Si(R 2 ) 3 , wherein L is selected from the group consisting of a divalent C 1-40 alkyl group, a divalent C 2-40 alkenyl group, a divalent C 1-40 haloalkyl group, and a covalent bond; R 2 is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group; and R 3 is selected from the group consisting of a C 3-10 cycloalkyl group, a C 6-14 aryl group, a C 6-14 haloaryl group, a 3-12 membered cycloheteroalkyl group, and a 5-14 membered heteroaryl group, each of which optionally is substituted with 1-5 substituents selected from the group consisting of a halogen, —CN, NO 2 , R 2 , OR 2 , and SR 2 ;

R 5 and R 6 independently are selected from the group consisting of H, R 2 , OR 2 , SR 2 , C(O)R 2 , OC(O)R 2 , and C(O)OR 2 ;

Q 1 and Q 2 independently are selected from the group consisting of:

wherein:

pi-2 is an optionally substituted conjugated polycyclic moiety;

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

Z is a conjugated noncyclic linker;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

m″ is 1, 2, 3, 4, 5 or 6; and

p and p′ independently are 0 and 1, provided that at least one of p and p′ is 1.

16. A compound comprising one or more moieties represented by formula (I):

wherein X is a chalcogen; and one or more linear conjugated moieties and/or one or more cyclic conjugated moieties other than the moieties represented by formula (I), wherein the compound is a small molecule represented by formula (IX) or (X):

wherein:

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

R 5 and R 6 independently are selected from the group consisting of H, R 2 , OR 2 , SR 2 , C(O)R 2 , OC(O)R 2 , and C(O)OR 2 ;

Q is absent or selected from the group consisting of:

and a covalent bond,

wherein:

pi-2 is an optionally substituted conjugated polycyclic moiety;

Ar, at each occurrence, is independently an optionally substituted 5- or 6-membered aryl or heteroaryl group;

Z is a conjugated noncyclic linker;

m and m′ independently are 0, 1, 2, 3, 4, 5 or 6, provided that at least one of m and m′ is not 0;

m″ is 1, 2, 3, 4, 5 or 6; and

p and p′ independently are 0 and 1, provided that at least one of p and p′ is 1.

17. The compound of claim 16 , wherein the compound is a small molecule represented by formula (XI), (XII), (XIII), (XIV), (XV), or (XVI):

18. The compound of 16 , wherein X is S, and wherein one of m and m′ is 0 and the other of m and m′ is 1, 2, 3, 4, 5 or 6.

19. An electronic device, an optical device, or an optoelectronic device comprising a thin film semiconductor component, the thin film semiconductor component comprising one or more compounds of claim 1 .

20. The compound of claim 15 , wherein X is selected from the group consisting of O, S, and Se.