BENZOTHIENOTHIOPHENE ISOINDIGO POLYMERS
20180009936 · 2018-01-11
Assignee
Inventors
- Pascal Hayoz (Hofstetten, CH)
- Daniel KAELBLEIN (Speyer, DE)
- Iain MCCULLOCH (Eastleigh, GB)
- Wan YUE (London, GB)
Cpc classification
C08G61/126
CHEMISTRY; METALLURGY
H10K85/111
ELECTRICITY
H01B1/127
ELECTRICITY
C09K2211/1483
CHEMISTRY; METALLURGY
C08G61/124
CHEMISTRY; METALLURGY
H01B1/128
ELECTRICITY
C08G2261/3223
CHEMISTRY; METALLURGY
International classification
C08G61/12
CHEMISTRY; METALLURGY
Abstract
Polymers comprising at least one unit of formula (1) and their use as semiconducting materials.
##STR00001##
Claims
1. A polymer comprising at least one unit of formula (1): ##STR00071## wherein R.sup.1 is at each occurrence selected from the group consisting of H, C.sub.1-100-alkyl, C.sub.2-100-alkenyl, C.sub.2-100-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl, a 5 to 20 membered heteroaryl, C(O)—C.sub.1-100-alkyl, C(O)—C.sub.5-12-cycloalkyl and C(O)—OC.sub.1-100-alkyl, wherein C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be substituted with one to fourty substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.aR.sup.b NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b], SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2, and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.aR.sup.b, NR.sup.a-C(O)R.sup.6, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b],SR.sup.aSi(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalky can be replaced by O, S, OC(O), CO, NR.sup.a or NR.sup.a-13 CO, C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.aR.sup.b, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b], SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, R.sup.Sia, R.sup.Sib and R.sup.Sic are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, O—C.sub.1-60-alkyl, O—C.sub.2-60-alkenyl, O—C.sub.2-60-alkynyl, O—C.sub.5-8-cycloalkyl, O—C.sub.6-14-aryl, O-5 to 14 membered heteroaryl, —[O—SiR.sup.SidR.sup.Sie].sub.o—R.sup.Sif, NR.sup.5R.sup.6, halogen and O—C(O)—R.sup.5, wherein o is an integer from 1 to 50, R.sup.Sid, R.sup.Sie, R.sup.Sif are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, O—C.sub.1-60-alkyl, O—C.sub.2-60-alkenyl, O—C.sub.2-60-alkynyl, O—C.sub.5-8-cycloalkyl, O—C.sub.6-14-aryl, O-5 to 14 membered heteroaryl, —[O—SiR.sup.SigR.sup.Sih].sub.p—R.sup.Sii, halogen and O—C(O)—R.sup.50; wherein p is an integer from 1 to 50, R.sup.Sig R.sup.Sih, R.sup.Sii are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, O—Si(CH.sub.3).sub.3, NR.sup.500R.sup.600, halogen and O—C(O)—R.sup.500 , R.sup.5, R.sup.6, R.sup.50, R.sup.60, R.sup.500 and R.sup.600 are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be substituted with one to twenty substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sub.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sup.c][C(O)R.sup.d], SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, CN, and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be replaced by O or S, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sup.c][C(O)R.sup.d], SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si (R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, CN, and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.c or NR.sup.c-CO, C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sub.c][C(O)R.sup.d], SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sii), halogen, CN and NO.sub.2; wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, R.sup.Sij, R.sup.Sik R.sup.Sil are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, [O—SiR.sup.SimR.sup.Sin].sub.qR.sup.Sio, NR.sup.7R.sup.8, halogen, and O—C(O)—R.sup.7, wherein q is an integer from 1 to 50, R.sup.Sim, R.sup.Sin, R.sup.Sio are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, —[O—SiR.sup.SipR.sup.Siq].sub.r—R.sup.Sir, NR.sup.70R.sup.80, halogen, and O—C(O)—R.sup.70; wherein r is an integer from 1 to 50, R.sup.Sip, R.sup.Siq, R.sup.Sir are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, O—Si(CH.sub.3).sub.3, NR.sup.700R.sup.800 , halogen and O—C(O)—R700 , R.sup.7, R.sup.8, R.sup.70, R.sup.80, R.sup.700 and R.sup.800 are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, and 5 to 10 membered heteroaryl, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents selected from the group consisting of halogen, CN and NO.sub.2, R.sup.2 is at each occurrence selected from the group consisting of hydrogen, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl, 5 to 20 membered heteroaryl, OR.sup.21, OC(O)—R.sup.21, C(O)—OR.sup.21, C(O)—R.sup.21, NR.sup.21R.sup.22, NR.sup.21—C(O)R.sup.22, C(O)—NR.sup.21R.sup.22, N[C(O)R.sup.21][C(O)R.sup.22], SR.sup.21, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and OH, wherein R.sup.21 and R.sup.22 and are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, and C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2, and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.e or NR.sup.e—CO, C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2, wherein R.sup.Sis, R.sup.Sit and R.sup.Siu are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, phenyl and O-13 Si(CH.sub.3).sub.3, R.sup.e and R.sup.f are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h NR.sup.g—C(O)R.sup.h C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; wherein R.sup.g and R.sup.h are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2, n is 0, 1, 2 or 3, m is 0, 1, 2 or 3, and L.sup.1 and are L.sup.2 are independently from each other and at each occurrence selected from the group consisting of C.sub.6-18-arylene, 5 to 20 membered heteroarylene, ##STR00072## wherein C.sub.6-18-arylene and 5 to 20 membered heteroarylene can be substituted with one to six substituents R.sup.3 at each occurrence selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, OR.sup.31, OC(O)—R.sup.31, C(O)—OR.sup.31, C(O)—R.sup.31, NR.sup.31R.sup.32, NR.sup.31—C(O)R.sup.32, C(O)—NR.sup.31R.sup.32, N[C(O)R.sup.31][C(O)R.sup.32], SR.sup.31, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and OH, and wherein ##STR00073## can be substituted with one or two substituents R.sup.4 at each occurrence selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, C(O)—R.sup.41, C(O)—NR.sup.41R.sup.42,C(O)—OR.sub.41 and CN, wherein R.sup.31, R.sup.32, R.sup.41 and R.sup.42 are independently from each other and at each occurrence selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, and wherein C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R.sup.i, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R.sup.i, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.i or NR.sup.i—CO, p1 C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2, wherein SiR.sup.SivR.sup.SiwR.sup.Six are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, phenyl and O—Si(CH.sub.3).sub.3, R.sup.i and R.sup.j are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)-R.sup.k, NR.sup.kR.sup.l, NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.l], SR.sup.k, halogen, CN, and NO.sub.2; C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)—R.sup.k, NR.sup.kR.sup.l NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.l], SR.sup.k, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)—R.sup.k, NR.sup.kR.sup.l NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.1], SR.sup.k, halogen, CN, and NO.sub.2, wherein R.sup.k and R.sup.l are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.
2. The polymer of claim 1, wherein R.sup.l is at each occurrence selected from the group consisting of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl, wherein C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be substituted with one to fourty substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, and CN; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be replaced by O or S, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, R.sup.Sia, R.sup.Sib and R.sup.Sic are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, -—[O—SiR.sup.SidR.sup.Sie].sub.o—R.sup.Sif, wherein o is an integer from 1 to 50, R.sup.Sid, R.sup.Sie and R.sup.Sif are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, —[O—SiR.sup.SigR.sup.Sih].sub.p—R.sup.Sii, wherein p is an integer from 1 to 50, R.sup.Sig R.sup.Sih, R.sup.Sih are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, O—Si(CH.sub.3).sub.3, R.sup.5, R.sup.6, R.sup.50, R.sup.60, R.sup.500 and R.sup.600 are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be substituted with one to twenty substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil, halogen, and CN; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be replaced by O or S, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, and CN; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.c or NR.sup.c—CO, C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, and CN; wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, R.sup.Sij, R.sup.Sik and R.sup.Sil are independently selected from the group consisting of H, C,.sub.1-30 alkyl C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, —[O—SiR.sup.Sim R.sup.Sin].sub.q—R.sup.Sio, wherein q is an integer from 1 to 50, R.sup.Sim, R.sup.Sin, R.sup.Sio are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, —[O—SiR.sup.SipR.sup.Siq].sub.r—R.sup.Sir, wherein r is an integer from 1 to 50, R.sup.Sip, R.sup.Siq, R.sup.Sir are independently selected from the group consisting of H,C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, O—Si(CH.sub.3).sub.3, C.sub.1-30alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents selected from the group consisting of halogen and CN, R.sup.2 is at each occurrence selected from the group consisting of hydrogen, C.sub.1-30-alkyl and halogen, wherein C.sub.-30-alkyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.c, OC(O)—R.sup.e C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-30-alkyl can be replaced by O or S, wherein R.sup.Sis, R.sup.Sit and R.sup.Siu are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, phenyl and O—Si(CH.sub.3).sub.3, R.sup.e and R.sup.f are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g , OC(O)—R.sup.g, C(O)—OR.sup.g , C(O)—R.sup.g , NR.sup.gR.sup.h, NR.sup.g —C(O)R.sup.h, C(O)13 NR.sup.g R.sup.h , N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; wherein R.sup.g and R.sup.h are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.
3. The polymer of claim 1, wherein R.sup.l is at each occurrence selected from the group consisting of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100alkynyl, wherein C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be substituted with one to fourty substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic) —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, and CN; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be replaced by O or S, wherein R.sup.a and R.sup.h are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, R.sup.Sia, R.sup.Sib and R.sup.Sic are independently selected from the group consisting of H, C.sub.1-60-alkyk C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, —[O—SiR.sup.SidR.sup.Sie].sub.o-R.sup.Sif, wherein o is an integer from 1 to 50, R.sup.Sid, R.sup.Sie and R.sup.Sif are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, —[O—Sir.sup.SigR.sup.Sih].sub.p—R.sup.Sii, wherein p is an integer from 1 to 50, R.sup.Sig R.sup.Sih, R.sup.Sii are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, O—Si(CH.sub.3).sub.3, C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be substituted with one to twenty substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sii), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil) , halogen, and CN; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be replaced by O or S, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sii), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, and CN; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.c or NR.sup.c—CO, C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cC(O)R.sup.d, C(O)—NR.sup.cR.sup.d, SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sii), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, and CN; wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, R.sup.Sij, R.sup.Sik and R.sup.Sid are independently selected from the group consisting of H, C.sup.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl —[O—SiR.sup.SimR.sup.Sin].sub.q—R.sup.Sio, wherein q is an integer from 1 to 50, R.sup.Sim, R.sup.Sin, R.sup.Sio are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, —[O—SiR.sup.SipR.sup.Siq].sub.r—R.sup.Sir, wherein r is an integer from 1 to 50, R.sup.Sip, R.sup.Siq, R.sup.Sir rare independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, O—Si(CH.sub.3).sub.3, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents selected from the group consisting of halogen and CN, R.sup.2 is at each occurrence selected from the group consisting of hydrogen, C.sub.1-30-alkyl and halogen, wherein C.sub.1-30-alkyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Sin and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-30-alkyl can be replaced by O or S, wherein R.sup.Sis, R.sup.Sit and R.sup.Sin are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, phenyl and O—Si(CH.sub.3).sub.3, R.sup.e and R.sup.f are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-.sub.10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; wherein R.sup.g and R.sup.h are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.
4. The polymer of claim 1 wherein R.sup.l is at each occurrence selected from the group consisting of C.sub.1-36-alkyl, C.sub.2-36-alkenyl and C.sub.2-36-alkynyl, wherein C.sub.1-36-alkyl, C.sub.2-36-alkenyl and C.sub.2-36-alkynyl can be substituted with one to twenty substituents independently selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, and CN; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-36-alkyl, C.sub.2-36-alkenyl and C.sub.2-36-alkynyl can be replaced by O or S, wherein R.sup.a is independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl and C.sub.6-10.sup.-aryl R.sup.Sia, R.sup.Sib and R.sup.Sic are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl,—[O—SiR.sup.SidR.sup.Sie].sub.o—R.sup.Sif wherein o is an integer from 1 to 50, R.sup.Sid, R.sup.Sie, R.sup.Sif are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, —[O—SiR.sup.SigR.sup.Sih].sub.p-—R.sup.Sii, wherein p is an integer from 1 to 50, R.sup.Sig R.sup.Sih, R.sup.Sii are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, O—Si(CH.sub.3).sub.3, C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to ten substituents selected from the group consisting of halogen and CN, R.sup.2 is at each occurrence selected from the group consisting of unsubstituted hydrogen, C.sub.1-30-alkyl and halogen.
5. The polymer of claim 1, wherein R.sup.1 is at each occurrence unsubstituted C.sub.1-36-alkyl, and R.sup.2 is at each occurrence hydrogen.
6. The polymer of claim 1, wherein L.sup.1 and L.sup.2 are independently from each other and at each occurrence selected from the group consisting of 5 to 20 membered heteroarylene, ##STR00074## and wherein 5 to 20 membered heteroarylene can be substituted with one to six substituents R.sup.3 at each occurrence selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, OR.sup.31, OC(O)—R.sup.31, C(O)—OR.sup.31, C(O)—R.sup.31, NR.sup.31R.sup.32, NR.sup.31—C(O)R.sup.32, C(O)—NR.sup.31R.sup.32, SR.sup.31, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and OH, and wherein ##STR00075## can be substituted with one or two substituents R.sup.4 at each occurrence selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, C(O)—R.sup.41, C(O)—NR.sup.41R.sup.42, C(O)—OR.sup.41 and CN, wherein R.sup.31, R.sup.32, R.sup.41 and R.sup.42 are independently from each other and at each occurrence selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, and wherein C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R.sup.i, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R.sup.i, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.i or NR.sup.i—CO, C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.i, OC(O)—R.sup.j, C(O)—OR.sup.i, C(O)—R.sup.i, NR.sup.iR.sup.j, NR.sup.i—C(O)R.sup.j, C(O)—NR.sup.iR.sup.j, N[C(O)R.sup.i][C(O)R.sup.j], SR.sup.i, halogen, CN, SiR.sup.SivR.sup.SiwR.sup.Six and NO.sub.2, wherein SiR.sup.SivR.sup.SiwR.sup.Six are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.—6-cycloalkyl, phenyl and O—Si(CH.sub.3).sub.3, R.sup.i and R.sup.j are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-.sub.10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)—R.sup.k, NR.sup.kR.sup.l, NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.l], SR.sup.k, halogen, CN, and NO.sub.2, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)—R.sup.k, NR.sup.kR.sup.l NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.l], SR.sup.khalogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.k, OC(O)—R.sup.l, C(O)—OR.sup.k, C(O)—R.sup.k, NR.sup.kR.sup.l NR.sup.k—C(O)R.sup.l, C(O)—NR.sup.kR.sup.l, N[C(O)R.sup.k][C(O)R.sup.l], SR.sup.k, halogen, CN, and NO.sub.2; wherein R.sup.k and R.sup.l are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.
7. The polymer of claim 6, wherein L.sup.1 and L.sup.2 are independently from each other and at each occurrence selected from the group consisting of 5 to 20 membered heteroarylene, ##STR00076## and wherein 5 to 20 membered heteroarylene is selected from the group consisting of ##STR00077## wherein R.sup.104 and R.sup.105 are independently and at each occurrence selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, or R.sup.104 and R.sup.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 C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.s, OC(O)—R.sup.t, C(O)—OR.sup.s, C(O)—R.sup.s, NR.sup.sR.sup.t NR.sup.s—C(O)R.sup.t, C(O)—NR.sup.sR.sup.t, N[C(O)R.sup.s][C(O)R.sup.t], SR.sup.s, halogen, CN, and NO.sub.2; C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.s, OC(O)—R.sup.t, C(O)—OR.sup.s, C(O)—R.sup.s, NR.sup.sR.sup.t NR.sup.s—C(O)R.sup.t, C(O)—NRsR.sup.t, N[C(O)R.sup.s] [C(O)R.sup.t], SR.sup.s, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-.sub.10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.s, OC(O)—R.sup.t, C(O)—OR.sup.s, C(O)—R.sup.s, NR.sup.sR.sup.t NR.sup.s—C(O)R.sup.t, C(O)—NR.sup.sR.sup.t, N[C(O)R.sup.s][C(O)R.sup.t],SR.sup.s, halogen, CN, and NO.sub.2; 5 to 12 membered ring system can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.s, OC(O)—R.sup.t, C(O)—OR.sup.s, C(O)—R.sup.s, NR.sup.sR.sup.t, NR.sup.s—C(O)R.sup.t, C(O)—NR.sup.sR.sup.t, N[C(O)R.sup.s][C(O)R.sup.t], SR.sup.s, halogen, CN, and NO.sub.2; wherein R.sup.s and R.sup.t are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2, wherein 5 to 20 membered heteroarylene can be substituted with one to six substituents R.sup.3 at each occurrence selected from the group consisting of C.sub.1-30-alkyl and halogen, and wherein ##STR00078## can be substituted with one or two substituents R.sup.4 at each occurrence selected from the group consisting of C.sub.1-30-alkyl, C(O)—R.sup.41, C(O)—OR.sup.41 and CN, wherein R.sup.41 is at each occurrence C.sub.1-30-alkyl.
8. The polymer of claim 7, wherein L.sup.1 and L.sup.2 are independently from each other and at each occurrence 5 to 20 membered heteroarylene, wherein 5 to 20 membered heteroarylene is selected from the group consisting of ##STR00079## wherein 5 to 20 membered heteroarylene is unsubstituted.
9. The polymer of claim 1, wherein n is 0, 1 or 2, and m is 0, 1 or 2.
10. A process for preparing the polymer of claim 1, wherein the formula (1) is formula (1-1) ##STR00080## the process comprising: reacting a compound of formula (2) ##STR00081## wherein Y is at each occurrence I, Br, Cl or O—S(O).sub.2CF.sub.3, with a compound of formula (3) ##STR00082## wherein Z.sup.a and Z.sup.b are independently selected from the group consisting of B(OZ.sup.1)(OZ.sup.2), SnZ.sup.1Z.sup.2Z.sup.3, ##STR00083## wherein Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 and Z.sup.6 are independently from each other and at each occurrence H or C.sub.1-4-alkyl.
11. An intermediate of formula (2) or (2′) ##STR00084## wherein Y is at each occurrence I, Br, Cl or O—S(O).sub.2CF.sub.3, R.sup.1 is at each occurrence selected from the group consisting of H, C.sub.1-100-alkyl, C.sub.2-100-alkenyl, C.sub.2-100-alkynyl, C.sub.5-12cycloalkyl, C.sub.6-18-aryl, a 5 to 20 membered heteroaryl, C(O)—C.sub.1-100-alkyl, C (O)—C.sub.5-12-cycloalkyl and C(O)—OC.sub.1-100-alkyl, wherein C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be substituted with one to fourty substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR, C(O)—R.sup.a, NR.sup.aR.sup.b, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b], SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-100-alkyl, C.sub.2-100-alkenyl and C.sub.2-100-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C,.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.aR.sup.b, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b], SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.a or NR.sup.a—CO, C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-60-alkyl, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.a, OC(O)—R.sup.a, C(O)—OR.sup.a, C(O)—R.sup.a, NR.sup.aR.sup.b, NR.sup.a—C(O)R.sup.b, C(O)—NR.sup.aR.sup.b, N[C(O)R.sup.a][C(O)R.sup.b], SR.sup.a, Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), —O—Si(R.sup.Sia)(R.sup.Sib)(R.sup.Sic), halogen, CN, and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, R.sup.Sia, R.sup.Sib R.sup.Sic are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, O—C.sub.1-60-alkyl,O—C.sub.2-60-alkenyl, O—C.sub.2-60-alkynyl, O—C.sub.5-8cycloalkyl, O—C.sub.6-14-aryl, O-5 to 14 membered heteroaryl, —[O—SiR.sup.SidR.sup.Sie].sub.o—R.sup.Sif, NR.sup.5R.sub.6, halogen and O—C(O)—R.sup.5, wherein o is an integer from 1 to 50, R.sup.Sid, R.sup.Sie, R.sup.Sif are independently selected from the group consisting of H, C.sub.1-60-alkyl, C .sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, O—C.sub.1-60-alkyl, O—C.sub.2-60-alkenyl, O—C.sub.2-60-alkynyl, O—C.sub.5-8-cycloalkyl, O—C.sub.6-14-aryl, O-5 to 14 membered heteroaryl, —[O—SiR.sup.SigR.sup.Sih].sub.p—R.sup.Sii, NR .sup.50R.sup.60 , halogen and O-13 C(O)—R.sup.50; wherein p is an integer from 1 to 50, R.sup.Sig R.sup.Sih, R.sup.Sii are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C .sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, O—Si(CH.sub.3).sub.3, NR.sup.500R.sup.600, halogen and O—C(O)—R.sup.500, R.sup.5, R.sup.6, R.sup.50, R.sup.60, R.sup.500 and R.sup.600 are independently selected from the group consisting of H, C.sub.1-60-alkyl, C.sub.2-60-alkenyl, C.sub.2-60-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be substituted with one to twenty substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sup.c][C(O)R.sup.d], SR.sup.c, Si (R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, CN, and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-60-alkyl, C.sub.2-60-alkenyl and C.sub.2-60-alkynyl can be replaced by O or S, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkenyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sup.c][C(O)R.sup.d], SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil)—O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sik),halogen, CN, and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.c or NR.sup.c—CO, C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, OR.sup.c, OC(O)—R.sup.c, C(O)—OR.sup.c, C(O)—R.sup.c, NR.sup.cR.sup.d, NR.sup.c—C(O)R.sup.d, C(O)—NR.sup.cR.sup.d, N[C(O)R.sup.c][C(O)R.sup.d], SR.sup.c, Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), —O—Si(R.sup.Sij)(R.sup.Sik)(R.sup.Sil), halogen, CN and NO.sub.2; wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.2-30-alkyl, C.sub.2-30-alkenyl, and C.sub.2-30-alkynyl, R.sup.Sij, R.sup.Sik and R.sup.Sil are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, —[O—SiR.sup.SimR.sup.Sim].sub.q—R.sup.Sio, NR.sup.7R.sup.8, halogen, and O—C(O)—R.sup.7, wherein q is an integer from 1 to 50, R.sup.Sim, R.sup.Sin, R.sup.Sio are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, O—C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl,—[O—Sir .sup.SipR.sup.Siq].sub.r-R.sup.Sir, NR.sup.70R.sup.80, halogen, O—C(O)—R.sup.70; wherein r is an integer from 1 to 50, R.sup.SiP, R.sup.Siq, R.sup.Sir are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.6-5-cycloalkyl, C.sub.6-10aryl, 5 to 10 membered heteroaryl, O-13 C.sub.1-30-alkyl, O—C.sub.2-30-alkenyl, O—C.sub.2-30-alkynyl, O—C.sub.5-6-cycloalkyl, O—C.sub.6-10-aryl, O-5 to 10 membered heteroaryl, O—Si(CH.sub.3) , NR.sup.700R.sup.800, halogen and O—C(O)—R700, R.sup.7, R.sup.8, R.sup.70, R.sup.80, R.sup.700 and R.sup.80 are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, and 5 to 10 membered heteroaryl, C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents selected from the group consisting of halogen, CN and NO.sub.2, R.sup.2 is at each occurrence selected from the group consisting of hydrogen, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl, 5 to 20 membered heteroaryl, OR.sup.21, OC(O)—R.sup.21, C(O)—OR.sup.21, C(O)—R21, NR.sup.21R.sup.22, NR.sup.21-C(O)R.sup.22, C(O)-13 NR.sup.21R.sup.22, N[C(O)R.sup.21][C(O)R.sup.22], SR.sup.21, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and OH, wherein R.sup.21 and R.sup.22 and are independently selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl and 5 to 20 membered heteroaryl, and C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2; and at least two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl can be replaced by O or S, C.sub.5-12-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20alkyl, C.sub.2-20alkenyl C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2; and one or two CH.sub.2-groups, but not adjacent CH.sub.2-groups, of C.sub.5-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR.sup.e or NR.sup.e—CO, C.sub.6-18-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, OR.sup.e, OC(O)—R.sup.e, C(O)—OR.sup.e, C(O)—R.sup.e, NR.sup.eR.sup.f, NR.sup.e—C(O)R.sup.f, C(O)—NR.sup.eR.sup.f, N[C(O)R.sup.e][C(O)R.sup.f], SR.sup.e, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and NO.sub.2, wherein R.sup.Sis, R.sup.Sit and R.sup.Siu are independently from each other selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, phenyl and O—Si(CH.sub.3).sub.3, R.sup.e and R.sup.f are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-8-cycloalkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, wherein C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sub.g, NR.sup.g—C(O)R.sub.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2, C.sub.5-8-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, C.sub.5-6-cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.h, C(O)—NR.sup.gR.sup.h, N[C(O)R.sup.g][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; C.sub.6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-.sub.10.sup.-alkenyl, C.sub.2-1-alkynyl, C.sub.5-6cycloalkyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.g, OC(O)—R.sup.g, C(O)—OR.sup.g, C(O)—R.sup.g, NR.sup.gR.sup.h, NR.sup.g—C(O)R.sup.K, C(O)—NR.sup.gR.sup.h, N[C(O)Rg][C(O)R.sup.h], SR.sup.g, halogen, CN, and NO.sub.2; wherein R.sup.g and R.sup.h are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.7-10-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.
12. An electronic device, comprising: a polymer of claim 1.
13. The electronic device of claim 12, wherein the electronic device is an organic field effect transistor.
14. (canceled)
Description
EXAMPLES
Example 1
[0457] a) Synthesis of compound I-1 is made is made in analogy to the literature by alkylation of 6,6′-dibromoisoindigo:
##STR00057##
[0458] b) Synthesis of 6,6′-diborate ester-isoindigo (I-2)
##STR00058##
[0459] A mixture of 6,6′-dibromoisoindigo I-1 (3 g, 2.75 mmol), bis(pinacolato)diboron (1.75 g, 6.88 mmol), Pd(PPh.sub.3).sub.2Cl.sub.2 (190 mg, 0.275 mmol) and potassium acetate (1.08 g, 11 mmol) in anhydrous toluene (50 mL) are heated to 110° C. for 16 h under argon. The reaction mixture is then cooled to r.t and plugged through a short pad silica gel with methylene chloride. The collected filtration is concentrated and dried to give 6, 6′-diborate ester isoindigo without further purification as a dark red solid (2.65 g, 81%). .sup.1H NMR (400 MHz, CDCI.sub.3, 300 K), δ (ppm): 9.14 (d, .sup.3J=7.9 Hz, 2 H), 7.48 (dd, .sup.3J=7.9, .sup.4J=0.6 Hz, 2 H), 7.16 (s, 2 H), 3.70-3.68 (m, 4 H), 1.96 (t, 2 H), 1.36 (s, 24 H), 1.35-1.24 (m, 80 H), 0.89-0.85 (m, 12 H). .sup.13C NMR (100 MHz, CDCI.sub.3, 300 K), δ (ppm): 168.09, 144.47, 134.31, 128.88, 128.74, 124.24, 113.50, 84.03, 44.45, 31.94, 30.02, 29.66, 29.37, 24.88, 22.70, 14.13.
[0460] c) Synthesis of 6, 6′- di(3-methylsulfinylthiophene) isoindigo (I-4):
##STR00059##
[0461] To an oven-dried 20 mL microwave vial, 6, 6′-diborate easter-isoindigo (I-2) (1.0 g, 7.7 mmol), Pd.sub.2(dba).sub.3 (38 mg, 0.038 mmol) and P-(o-tol).sub.3 (46 mg, 0.15 mmol), Bromo-3-methylsulfinylthiophene (I-3, made in analogy to the literature) (430 mg, 19.25 mol), the tube is sealed, then toluene (10 mL) with 2 drops of aliquat and 2M K.sub.3PO.sub.4 (3.5 mL) are added. The mixture is degassed under Argon for half an hour, and then the argon inlet is removed. The tube is subjected to reflux for 18 h. After cooling to room temperature, the reaction mixture is extracted with EA, and the organic phase is collected and dried with magnesium sulfate, solvent is removed by the reduced pressure, purified by column chromatography (eluent: DCM: EA=10:1) to afford a dark red solid (530 mg, 53%). .sup.1H NMR (400 MHz, CDCI3, 300 K) δ (ppm): 9.26 (d, .sup.3J=8.3 Hz, 2 H), 7.66 (d, .sup.3J =5.4 Hz, 2 H), 7.50 (d, .sup.3J =5.4 Hz, 2 H), 7.12 (dd, .sup.3J =8.3, .sup.4J=1.6 Hz, 2H), 6.95 (d, .sup.4J =1.4 Hz, 2 H), 3.76-3.65 (m, 4 H), 2.79 (s, 6 H), 1.94 (t, 2 H), 1.37-1.23 (m, 80 H), 0.88-0.84 (m, 12 H). .sup.13C NMR (100 MHz, CDCl.sub.3, 300 K), δ (ppm): 168.53, 145.66, 143.24, 135.45, 132.98, 130.72, 127.27, 125.41, 123.22, 122.00, 108.69, 44.05, 31.92, 31.76, 30.08, 29.63, 29.36, 26.52, 22.69, 14.12. HRMS (ESI, pos. mode): Calculated for C74H115N2O4S4: 1223.7661, [M+H]+, found: 1223.7594.
[0462] d) Synthesis of BTTIID (I-5)
##STR00060##
[0463] 6,6′-di(3-methylsulfinylthiophene) isoindigo (I-4) (800 mg, 0.65 mmol) is stirred with Eaton's reagent (6 mL) at room temperature in the dark for 3 days. The mixture is poured into ice-water, extracted with chloroform and the organic phased is dried with MgSO4, the solvent is removed by reduced pressure and the crude product is dried in vacuum, which is followed to be redissolved in pyridine (10 mL) and then the mixture is refluxed overnight. After the mixture is cooled to room temperature, extracted with chloroform and diluted hydrochloride acid, the separated organic phase is dried over MgSO4, and solvent is removed by reduced pressure. The crude is purified by column chromatography on silica gel (eluent: CHCl.sub.3: PE=1:3) to afford a red solid BTTIID (I-5) (450 mg, 59%). .sup.1H NMR (400 MHz, CDCl.sub.3, 300 K) δ (ppm): 9.81 (s, 2 H), 7.56 (d, .sup.3J=5.1 Hz, 2 H), 7.32 (d, .sup.3J=5.1 Hz, 2 H), 6.98 (s, 2 H), 3.72-3.70 (m, 4 H), 1.99 (t, 2 H), 1.38-1.21 (m, 80H), 0.88-0.83 (m, 12 H)..sup.13C NMR (100 MHz, CDCl.sub.3, 300 K), 6 (ppm): 168.52, 142.60, 142.18, 136.62, 134.86, 134.48, 132.12, 129.38, 125.86, 120.74, 120.07, 99.45, 44.74, 31.93, 31.67, 30.05, 29.68, 29.36, 26.54, 22.69, 14.12. MS (MALDI-TOF, CHCl.sub.3): Calculated for C72H106N202S4: 1158.71, found: 1158.4. UV-vis (CHCl.sub.3): lmax/nm (e/M-1 cm-1) =510 (36700). CV (CH2012, 0.1 M TBAHFP, vs Fc/Fc.sup.+): E.sub.1/2red (X/X.sup.−)=−1.28 V, E.sub.1/2red (X/X.sup.2−)=−1.64 V, E.sub.1/2ox (X/X+)=0.78 V
Example 2
[0464] Synthesis of dibromo BTTIID (I-6)
##STR00061##
[0465] NBS (65g, 0.36 mmol) is added in small portions to a solution of benzothienothiophene isoindigo (200g, 0.17 mmol) in CHCl.sub.3/AcOH (20 mL: 5 mL), the reaction mixture is stirred at reflux for about 5 h, which can be monitored by TLC. When the reaction is finished, cooled down to room temperature, the solvent is removed by reduced pressure and purified by column chromatography on silica gel (eluent: CHCl.sub.3: PE=1:4) to afford a red solid dibromo-BTTIID (I-6) (164 mg, 72%). .sup.1H NMR (400 MHz, CDCl.sub.3, 300 K), 6 (ppm): 9.70 (s, 2 H), 7.23 (s, 2 H), 6.67 (s, 2 H), 3.66−3.64 (m, 4 H), 1.92 (t, 2 H), 1.37−1.21 (m, 80 H), 0.88−0.83 (m, 12 H)..sup.130 NMR (100 MHz, CDCl.sub.3, 300 K), 6 (ppm): 168.25, 142.62, 140.63, 135.07, 134.79, 133.61, 131.87, 125.68, 123.27, 120.07, 116.14, 98.77, 44.72, 31.94, 30.08, 29.75, 29.69, 29.39, 26.61, 22.71, 14.13. MS (MALDI-TOF, CHCl.sub.3): Calculated for C72H104Br2N2O2S4: 1314.5, found: 1314.1.
Example 3
[0466] Synthesis of P1
##STR00062##
[0467] To a microwave vial is added dibromoBTTIID (I-6) (100 mg, 0.076 mmol, 1 equiv.) and 2,5-bis(trimethylstannyl)thiophene (31.04 mg, 0.076 μmol, 1 equiv), Pd2(dba)3 (1.50 mg) and P(o-Tol).sub.3 (1.84 mg). The tube is sealed and flushed with Argon, and then degassed chlorobenzene (2 mL) is added. The mixture is thoroughly degassed under Argon, and then the argon inlet is removed. The tube is subjected to the following conditions in a microwave reactor: 100° C. for 5 min, 140° C. for 5 min, 160° C. for 30 min. After cooling to RT, the polymer is precipitated into methanol, and filtered through a Soxhlet thimble. The polymer is extracted using Soxhlet apparatus with methanol, acetone, hexane, dichloromethane, chloroform and chlorobenzene. The chlorobenzene solution is concentrated and precipitated into methanol. The precipitates are filtered and dried under vacuum to afford P1 as a dark blue solid (40 mg, 40%). GPC (chlorobenzene, 80° C.): Mn 33000, Mw 91135 g mol-1, PDI=2.74. .sup.1H NMR (1,1,2,2-tetrachloroethane-d.sub.2, 130° C., 400 MHz), δ (ppm): 9.68 (broad), 6.63 (broad), 3.96−3.89 (broad), 2.15−2.13 (broad), 1.76−0.96 (broad).
Example 4
[0468] Synthesis of P2
##STR00063##
[0469] To a microwave vial is added dibromoBTTIID (I-6) (68.6 mg, 0.052 mmol,1 equiv.) and 2,5-bis(trimethylstannyl)selenophene (23.78 mg, 0.052 μmol, 1 equiv), Pd2(dba)3 (2 mg) and P(o-Tol) 3 (2.58 mg). The tube is sealed and flushed with Argon, and then degassed chlorobenzene (1.0 mL) is added. The mixture is thoroughly degassed under Argon, and then the argon inlet is removed. The tube is subjected to the following conditions in a microwave reactor: 100° C. for 5 min, 140° C. for 5 min, 160° C. for 30 min. After cooling to RT, the polymer is precipitated into methanol, and filtered through a Soxhlet thimble. The polymer is extracted using Soxhlet apparatus with methanol, acetone, hexane, dichloromethane, chloroform and chlorobenzene. The chloroform and chlorobenzene solution is concentrated and precipitated into methanol. The precipitates are filtered and dried under vacuum to afford P2 as a dark blue solid (55 mg (chloroform) and 6 mg (chlorobenzene), 87.1%). .sup.1H NMR (1,1,2,2-tetrachloroethane-d2, 130° C., 400 MHz), δ (ppm): 9.67 (broad), 6.49 (broad), 3.96−3.87 (broad), 1.64−0.96 (broad). GPC (chloroform fraction) (chlorobenzene, 80° C.): Mn 51500, Mw 17966 g mol-1, PDI=3.49.
Example 5
[0470] Synthesis of P3
[0471] The synthesis of polymer P3 is made in analogy to the synthesis of polymer P2:
##STR00064##
Example 6
[0472] Synthesis of P4
[0473] The synthesis of polymer P4 is made in analogy to the synthesis of polymer P2:
##STR00065##
Example 7
[0474] Synthesis of P5
[0475] The synthesis of polymer P5 is made in analogy to the synthesis of polymer P2:
##STR00066##
Example 8
[0476] Synthesis of compound (I-7)
[0477] Compound I-7 is synthesized in analogy to compound I-5
##STR00067##
Example 9
[0478] Synthesis of compound (I-8)
[0479] Compound I-8 is synthesized from I-7 in analogy to compound I-6
##STR00068##
Example 10
[0480] Synthesis of polymer (P6)
[0481] Polymer P6 is synthesized from I-8 in analogy to polymer P2
##STR00069##
Example 11
[0482] Synthesis of compound (I-9)
[0483] Compound I-9 is synthesized in analogy to compound I-5
##STR00070##
Example 12
[0484] Fabrication and electrical characterization of organic field-effect transistors (OFET) based on compounds and polymers of the present invention
[0485] Preparation of back-contact, top-gate FETs
[0486] Semiconducting compound I-x or polymer Px is dissolved at a concentration of 0,75wt % in orthodichlorobenzene and subsequently coated onto a PET-substrate with lithographically prepatterned gold contacts, serving as Source and Drain contact of the FET. 100 μl of the formulation is coated by a standard blade coater at a coating speed of 20 mm/s, yielding a homogenous layer of the semiconductor over the entire substrate. After the coating is completed, the substrate is immediately transferred onto a preheated hotplate and heated for 30s at 90° C. Next the gate dielectric layer consisting of Cytop CTL-809M is spincoated on top of the organic semiconductor (1200 rpm, 30s). After Spincoating, the substrate is again transferred to the hotplate and annealed for another 5 Min at 100° C. The thickness of the dielectric layer is 535 nm measured by profilometer. Finally 50 nm thick shadow-mask patterend gold gate electrodes are deposited by vacuum evaporation to complete FETs in the BGTC-configuration (See FIG. 1a-h)
Electrical characterization
[0487] The mobility μ is calculated from the root representation of the transfer characteristic curve (solid grey curve) calculated in the saturation region. The slope m is determined from the dashed black line in FIG. 1. The dashed black line in FIG. 1 is fitted to a region of the root representation of the current characteristic ID such that a good correlation to the linear slope of the root representation is obtained.
[0488] The threshold voltage U.sub.Th can be taken from the intersection of black dashed line in FIG. 1 with the X-axis portion (V.sub.GS).
[0489] In order to calculate the electrical properties of the OFET, the following equations are employed:
[0490] where ε.sub.0 is the vacuum permittivity of 8.85×10.sup.−12 As/Vm. ε.sub.r=2,1 for Cytop and d=535 nm is the thickness of the dielectric. With the channel length L=10 μm and the channel width W=250 μm.
[0491] The following mobilities have been calculated for the respective compounds:
TABLE-US-00001 Compound I-x Field-effect mobility μ Threshold voltage ON/OFF Polymer Px [cm.sup.2/Vs] U.sub.TH [V] ratio I-7 1.3E−2 0.72 5E3 I-9 6E−4 −10.8 8E2 P6 3E−3 −6.0 1E3 P1 high Mw 4.5E−2 −4.7 6E4 P3 5E−4 −13.87 7E2 P1 low Mw 9E−3 −3.62 9E3 P2 5E−2 −2.05 1E4 P4 2E−3 7.5 3E8