Naphthoindacenodithiophenes and polymers
Polymers comprising at least one unit of formula 1 and compounds of the formula 1′ wherein, in formulae 1 and 1′ n is 0, 1, 2, 3 or 4 m is 0, 1, 2, 3 or 4 X is at each occurrence selected from the group consisting of O, S, Se or Te, Q is at each occurrence selected from the group consisting of C, Si or Ge R is at each occurrence selected from the group consisting of hydrogen, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, R 2 , R 2′ , R* are at each occurrence independently selected from the group consisting of hydrogen, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, 5 to 20 membered hetero-aryl, OR 21 , OC(O)—R 21 , C(O)—OR 21 , C(O)—R 21 , NR 21 R 22 , NR 21 —C(O)R 22 , C(O)—NR 21 R 22 , N[C(O)R 21 ][C(O)R 22 ], SR 21 , halogen, CN, SiR Sis R Sit R Siu and OH, L 1 and L 2 are independently from each other and at each occurrence selected from the group consisting of C 6-30 -arylene, 5 to 30 membered heteroarylene.
1. A polymer comprising a unit of formula 1:
wherein:
n is 0, 1, 2, 3, or 4;
m is 0, 1, 2, 3, or 4;
R is selected from the group consisting of hydrogen, C 1-30 -alkyl, and phenyl;
L 1 and L 2 are each independently selected from the group consisting of C 6-30 -arylene, 5 to 30 membered heteroarylene,
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl, OR 31 , OC(O)—R 31 , C(O)—OR 31 , C(O)—R 31 R 32 , NR 31 —C(O)R 32 ,C(O)—NR 31 R 32 , N[C(O)R 31 ][C(O)R 32 ], SR 31 , halogen, CN, SiR Siv R Siw R Six and OH,
wherein
are optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl, C(O)—R 41 , C(O)—NR 41 R 42 , C(O)—OR 41 and CN,
wherein, in R 31 , R 32 , R 41 , and R 42 , are each independently selected from the group consisting of H, C 1-30 -alkynyl, C 2-30 -alkenyl, C 2-36 -alkynyl, C 5-12 , -cycloalkyl, C 6-18 -aryl and 5 and 20 membered heroaryl,
wherein, in R 31 , R 32 , R 41 , are each independently selected from the group consisting of H, C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl C 5-12 - cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 5-12 -cycloalkyl is optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 : and one or two CH 2 -groups, but not adjacent CH 2 -groups, of C 5-12 -cycloalkyl are optionally replaced by O, S, OC(O), CO, NR i or NR i —CO,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 6-18 -aryl and 5 to 20 membered heteroaryl are optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR siv R Siw R Six and NO 2 ,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally substituted with one to ten substituents independently selected from the group consisting of C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 ; and at least two CH 2 -groups, but not adjacent CH 2 -groups of C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally replaced by O or S,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 5-12 -cycloalkyl is optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, and C 2-20 -alkeynyl and C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C (O)R j , C(O)—NR i R j , N[C(O)R i C(O)R i ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 : and one or two CH 2 -groups, but not adjacent CH 2 -groups, of C 5-12 -cycloalkyl are optionally replaced by O, S, OC(O), CO, NR i or NR i —CO,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 6-18 -aryl and 5 to 20 membered heteroaryl are optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 ,
wherein R Siv , R Siw , and R Six are each independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, phenyl and O-Si(CH 3 ) 3 ,
wherein R i , R j are each independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl,
wherein, in R Siv , R Siw , R Six , R i , R j , C 1-20 -alkyl, C 2-20 -alkenyl and C 20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R l , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R Siv , R Siw , R Six , R i , and R j , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R l , C(O)—OR k , C(O)—R k , NR k R l , NR k —C(O)R l , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 .
wherein, in R Siv , R Siw , R Six , R i , and R j , C 6-14 -aryl and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R l , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R l ], SR k , halogen, CN, and NO 2 ,
wherein R k and R l , are independently selected from the group consisting of H, C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl, and
wherein, in R k and R l , C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN and NO 2 .
2. The polymer of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of C 6-30 -arylene and 5 to 30 membered heteroarylene, and
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl, OR 31 , OC(O)—R 31 , C(O)—OR 31 , C(O)—R 31 , NR 31 R 32 , NR 31 —C(O)R 32 , C(O)—NR 31 R 32 , SR 31 , halogen, CN, SiR Siv R Siw R Six and OH, and
wherein
is optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl, C(O)—R 41 , C(O)—NR 41 R 42 , C(O)—OR 41 and CN,
wherein R 31 , R 32 , R 41 and R 42 are each independently selected from the group consisting of H, C 1-30 alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl,
wherein, R 31 , R 32 , R 41 , and R 42 , C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally substituted with one to ten substituents independently selected from the group consisting of C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)R j , C(O)- OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 ; and at least two CH 2 -groups, but not adjacent CH 2 -groups of C 1-30 - alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally replaced by O or S,
wherein, R 31 , R 32 , R 41 , and R 42 , C 5-12 -cycloalkyl is optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR—C(O)R k , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 ; and one or two CH 2 -groups, but not adjacent CH 2 -groups, of C 5-12 -cycloalkyl are optionally replaced by O, S, OC(O), CO, NR i or NR i —CO,
wherein, R 31 , R 32 , R 41 , and R 42 , C 6-18 -aryl and 5 to 20 membered heteroaryl are optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six and NO 2 ,
wherein SiR Siv R Siw R Six are each independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, phenyl and O-Si(CH 3 ) 3 , and
wherein R i and R j are independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl,
wherein, in R i and R j , C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R l , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R i and R j , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R l ], SR k , halogen, CN, and NO 2 ,
wherein, in R i and R j , C 6-14 -aryl and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein R k and R 1 are independently selected from the group consisting of H, C 1-10 alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl, and
wherein, in R k and R 1 , C 2-10 -alkenyl and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN and NO 2 .
3. The polymer of claim 2 , wherein L 1 and L 2 are each independently selected from the group consisting of C 6-30 -arylene and 5 to 30 membered heteroarylene, and
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene is selected from the group consisting of
wherein R l is selected from the group consisting of C 1-36 -alkyl, C 3-36 -alkenyl and C 3-36 alkynyl,
wherein C 1-36 -alkyl, C 3-36 -alkenyl and C 3-36 -alkynyl are optionally substituted with one to twenty substituents independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR a , SR a , Si(R sia )(R Sib )(R Sic ), —O-Si(R Sia )(R Sib )(R Sic ), halogen, and CN; and at least two CH 2 -groups, but not adjacent CH 2 -groups, of C 1-36 -alkyl, C 2-36 -alkenyl and C 2-36 -alkynyl are optionally replaced by O or S,
wherein R a is independently selected from the group consisting of H, C 3-20 -alkenyl, C 3-20 -alkynyl, C 5-6 -cycloalkyl and C 6-10 aryl,
wherein R Sia , R Sib and R Sic are independently selected from the group consisting of H, C 1-26 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, —[O-SiR Sid R Sie ] 0 —R Sif
wherein o is an integer from 1 to 50,
wherein R Sid , R Sie , R Sif are independentl selected from the group consisting of H, C 1-30 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, -[O-SiR Sig R Sih ] p —R Sii ,
wherein p is an integer from 1 to 50,
wherein R Sig R Sih , R Sii are indeendently selected from the group consisting of H, C 1-30 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, O-Si(CH 3 ) 3 ,
C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl are optionally substituted with one to ten substituents selected from the group consisting of halogen and CN,
wherein R 104 and R 105 are independently and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl, or R 104 and R 105 , if attached to the same atom, together with the atom, to which they are attached, form a 5 to 12 membered ring system,
wherein, in R 104 and R 105 , C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R l , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R 1 , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R l ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , C 6-14 -aryl and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , 5 to 12 membered ring system is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR 3 , OC(O)—R t , C(O)—OR s , C(O)-R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein R s and R t are independently selected from the group consisting of H, C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl,
wherein, in R s and R t , C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN and NO 2 ,
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 at each occurrence selected from the group consisting of C 1-30 -alkyl and halogen,
wherein
is optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C(O)—R 41 , C(O)—OR 41 and CN, and
wherein R 41 is at each occurrence C 1-30 -alkyl.
4. The polymer of claim 3 , wherein L 1 and L 2 are each independently selected from a group consisting of
and wherein L 1 and L 2 are not further substituted.
5. The polymer of claim 1 , wherein L 1 and L 2 are selected from
6. The polymer of claim 1 , wherein:
n is 0, 1, or 2; and
m is 0, 1, or 2.
7. An electronic device, comprising the polymer of claim 1 .
8. The electronic device of claim 7 , wherein the electronic device is an organic field effect transistor.
9. The polymer of claim 1 , comprising at least 2 units of the formula 1 and having a M n of up to 15000 and/or M w of up to 26000.
10. The polymer of claim 1 , wherein the polymer has a PDI up to 1.7.
11. A polymer comprising a unit of formula 1
or
a compound of formula 1′:
wherein
n is 1, 2, 3, or 4,
m is 0, 1, 2, 3, or 4,
R is hydrogen, C 1-30 -alkyl, and phenyl;
wherein L 1 comprises
wherein L 2 , is selected from the group consisting of C 6-30 -arylene, 5 to 30 membered heteroarylene,
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, 5 to 20 membered heteroaryl, OR 31 , OC(O)—R 31 , C(O)—OR 31 , C(O)—R 31 , NR 31 R 32 , NR 31 —C(O)R 32 , C(O)—NR 31 R 32 , N[C(O)R 31 ][C(O)R 32 ], SR 31 , halogen, CN, SiR Siv R Siw R Six , and OH,
wherein
are optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, 5 to 20 membered heteroaryl, C(O)—R 41 , C(O)—NR 41 R 42 , C(O)—OR 41 , and CN,
wherein R 31 , R 32 , R 41 , and R 42 are each independently selected from the group consisting of H, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, and 5 to 20 membered heteroaryl,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally substituted with one to ten substituents independently selected from the group consisting of C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR I C(O)—R i , NR i R I , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R six , and NO 2 ; and at least two CH 2 -groups, but not adjacent CH 2 -groups of C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally replaced by O or S,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 5-12 -cycloalkyl is optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six , and NO 2 ; and one or two CH 2 -groups, but not adjacent CH 2 -groups, of C 5-12 -cycloalkyl are optionally replaced by O, S, OC(O), CO, NR i , or NR i —CO,
wherein, in R 31 , R 32 , R 41 , and R 42 , C 6-18 -aryl and 5 to 20 membered heteroaryl are optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R I ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six , and NO 2 ,
wherein R Siv , R Siw , R Six are each independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, phenyl and O-Si(CH 3 ) 3 ,
wherein R i and R j are independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl,
wherein, in R Siv , R Siw , R Six , R i , R j , C 1-20 -alkyl, C 2-20 -alkenyl, and C 2-20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R Siv , R Siw , R Six , R i , and R j , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R Siv , R Siw , R Six , R i , R j , C 6-14 -aryl and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R l , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein R k and R 1 are independently selected from the group consisting of H, C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl, and
wherein, in R k and R 1 , C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN, and NO 2 .
12. The polymer or compound of claim 11 , wherein L 2 is selected from the group consisting of C 6-30 -arylene and 5 to 30 membered heteroarylene, and
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, 5 to 20 membered heteroaryl, OR 31 , OC(O)—R 31 , C(O)—OR 31 , C(O)-R 31 , NR 31 R 32 , NR 31 —C(O)R 32 , C(O)—NR 31 R 32 , SR 31 , halogen, CN, SiR Siv R Siw R Six , and OH, and
wherein
is optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl and 5 to 20 membered heteroaryl, C(O)R -41 , C(O)—NR 41 R 42 , C(O)—OR 41 , and CN,
wherein R 31 , R 32 , R 41 , and R 42 are each independently selected from the group consisting of H, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-12 -cycloalkyl, C 6-18 -aryl, and 5 to 20 membered heteroaryl,
wherein, R 31 , R 32 , R 41 , and R 42 , C 1-30 -alkyl, C 2-30 -alkenyl, and C 2-30 -alkynyl are optionally substituted with one to ten substituents independently selected from the group consisting of C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)-R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six , and NO 2 ; and at least two CH 2 -groups, but not adjacent CH 2 -groups of C 1-30 -alkyl, C 2-30 -alkenyl, and C 2-30 -alkynyl are optionally replaced by O or S,
wherein, R 31 , R 32 , R 41 , and R 42 , C 5-12 -cycloalkyl is optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ], [C(O)R j ], SR i , halogen, CN, SiR Siv R Siw R Six , and NO 2 ; and one or two CH 2 -groups, but not adjacent CH 2 -groups, of C 5-12 -cycloalkyl are optionally replaced by O, S, OC(O), CO, NR i , or NR i —CO,
wherein, R 31 , R 32 , R 41 , and R 42 , C 6-18 -aryl and 5 to 20 membered heteroaryl are optionally substituted with one to six substituents independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, 5 to 14 membered heteroaryl, OR i , OC(O)—R j , C(O)—OR i , C(O)—R i , NR i R j , NR i —C(O)R j , C(O)—NR i R j , N[C(O)R i ][C(O)R j ], SR i , halogen, CN, SiRs Siv R Siw R Six , and NO 2 ,
wherein SiR Siv R Siw R Six are each independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, phenyl, and O-Si(CH 3 ) 3 , and
wherein R i and R j are independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl,
wherein, in R i and R j , C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R l , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R i and R j , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N [C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein, in R i and R j , C 6-14 -aryl, and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR k , OC(O)—R 1 , C(O)—OR k , C(O)—R k , NR k R 1 , NR k —C(O)R 1 , C(O)—NR k R 1 , N[C(O)R k ][C(O)R 1 ], SR k , halogen, CN, and NO 2 ,
wherein R k and R 1 are independently selected from the group consisting of H, C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl, and
wherein, in R k and R 1 , C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN and NO 2 .
13. The polymer or compound of claim 12 , wherein L 2 is selected from the group consisting of C 6-30 -arylene and 5 to 30 membered heteroarylene, and
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene is selected from the group consisting of
wherein R 1 is selected from the group consisting of C 1-36 -alkyl, C 3-36 -alkenyl, and C 3-36 -alkynyl,
wherein C 1-36 -alkyl, C 3-36 -alkenyl and C 3-36 -alkynyl are optionally substituted with one to twenty substituents independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR a , SR a , Si(R Sia )(R Sib )(R Sic ), —O—Si(R Sia )(R Sib )(R Sic ), halogen, and CN; and at least two CH 2 -groups, but not adjacent CH 2 ,-groups, of C 1-36 -alkyl, C 2-36 -alkenyl, and C 2-36 -alkynyl are optionally replaced by O or S,
wherein R a is independently selected from the group consisting of H, C 3-20 -alkenyl, C 3-20 -alkynyl, C 5-6 -cycloalkyl, and C 6-10 -aryl,
wherein R Soa , R Sib and R Sic are independently selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, and -[O-SiR Sid R Sie ] o—R Sif
wherein o is an integer from 1 to 50,
wherein R Sid , R Sie , R Sif are independently selected from the group consisting of H, C 1-30 - alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, and —[O-SiR Sig R Sih ]p—R Sii ,
wherein p is an integer from 1 to 50,
wherein R Sig R Sih , R Sii are independently selected from the group consisting of H, C 1-30 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, and O-Si(CH 3 ) 3 ,
C 1-20 -alkyl, C 2-20 -alkenyl, and C 2-20 -alkynyl are optionally substituted with one to ten substituents selected from the group consisting of halogen and CN,
wherein R 104 and R 105 are independently and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl, and 5 to 14 membered heteroaryl, or R 104 and R 105 , if attached to the same atom, together with the atom, to which they are attached, form a 5 to 12 membered ring system,
wherein, in R 104 and R 105 , C 1-20 -alkyl, C 2-20 -alkenyl, and C 2-20 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of C 5-6 -cycloalkyl, C 6-l0 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , C 5-8 -cycloalkyl is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , C 6-14 -aryl and 5 to 14 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein, in R 104 and R 105 , 5 to 12 membered ring system is optionally substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-10 -alkenyl, C 2-10 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 10 membered heteroaryl, OR s , OC(O)—R t , C(O)—OR s , C(O)—R s , NR s R t , NR s —C(O)R t , C(O)—NR s R t , N[C(O)R s ][C(O)R t ], SR s , halogen, CN, and NO 2 ,
wherein R s and R t are independently selected from the group consisting of H, C 1-10 - alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl,
wherein, in R s and R t , C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN, and NO 2 ,
wherein C 6-30 -arylene and 5 to 30 membered heteroarylene are optionally substituted with one to six substituents R 3 at each occurrence selected from the group consisting of C 1-30 -alkyl and halogen,
wherein
is optionally substituted with one or two substituents R 4 selected from the group consisting of C 1-30 -alkyl, C(O)—R 41 , C(O)—OR 41 and CN, and
wherein R 41 is at each occurrence C 1-30 -alkyl.
14. The polymer or compound of claim 13 , wherein L 2 is selected from a group consisting of
wherein L 1 and L 2 are not further substituted.
15. The polymer or compound of claim 11 , wherein L 2 is selected from
16. The polymer or compound of claim 11 , wherein:
n is 1, or 2; and
m is 0, 1, or 2.
17. An electronic device, comprising the polymer or compound of claim 11 .
18. The electronic device of claim 11 , wherein the electronic device is an organic field effect transistor.
19. The polymer or compound of claim 11 , wherein L 1 comprises:
20. The polymer or compound of claim 11 , wherein L 1 comprises: