Thieno-indeno-monomers and polymers

Patent metadata

Field	Value
Publication number	US-2022041617-A1
Application number	US-202117508164-A
Country	US
Kind code	A1
Filing date	Oct 22, 2021
Priority date	Dec 6, 2016
Publication date	Feb 10, 2022
Grant date	—

Abstract

Polymers comprising at least one unit of formulaeand compounds of the formulaewherein, in formulae 1, 1′, 2 and 2′n is 0, 1, 2, 3 or 4m is 0, 1, 2, 3 or 4M1 and M2 are independently of each other an aromatic or heteroaromatic monocyclic or bicyclic ring system;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 GeR is at each occurrence selected from the group consisting of hydrogen, C1-100-alkyl, C2-100-alkenyl, C2-100-alkynyl, C5-12-cycloalkyl, C6-18-aryl, a 5 to 20 membered heteroaryl, C(O)—C1-100-alkyl, C(O)—C5-12-cycloalkyl and C(O)—OC1-100-alkyl.R2, R2′, R2″, R* are at each occurrence independently selected from the group consisting of hydrogen, C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, C5-12-cycloalkyl, C6-18-aryl, 5 to 20 membered heteroaryl, OR21, OC(O)—R21, C(O)—OR21, C(O)—R21, NR21R22, NR21—C(O)R22, C(O)—NR21R22, N[C(O)R21][C(O)R22], SR21, halogen, CN, SiRSisRSitRSiu and OH,L1 and L2 are independently from each other and at each occurrence selected from the group consisting of C6-30-arylene, 5 to 30 membered heteroarylene,

First claim

1 : A polymer, comprising a unit of formulae (1c):

Wherein:
X, Y are S;
Q is C;
L 2 is selected from the group consisting of C 6-30 -arylene, 5 to 30 membered heteroarylene,

C 6-30 -arylene and 5 to 30 membered heteroarylene can be substituted with one to six substituents R 3 at each occurrence 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 , N[C(O)R 31 ][C(O)R 32 ], SR 31 halogen, CN, SiR Siv R Siw R Six and OH,

can be substituted with one or two substituents R 4 at each occurrence 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, R 31 , R 32 , R 41 and R 42 are independently from each other and at each occurrence 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,
C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be 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 can be replaced by O or S,
C 5-12 -cycloalkyl can be 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 i , 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 ], SRI, 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 can be replaced by O, S, OC(O), CO, NR i or NR i —CO,
C 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 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 ,
R Siv , R Siw , R Six are independently from each other 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 ,
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 6-10 -aryl, and 5 to 14 membered heteroaryl,
C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl can be 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 l , NR k —C(O)R l , C(O)—NR k R l , N[C(O)R k ][C(O)R l ], SR k , halogen, CN, and NO 2 ,
C 5-8 -cycloalkyl can be substituted with one to five substituents selected from the group consisting of C 1-10 -alkyl, C 2-20 -alkenyl, C 2-20 -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 l , N[C(O)R k ][C(O)R l ], SR k , halogen, CN, and NO 2 ,
C 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 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 l , N[C(O)R k ][C(O)R l ], SR k , halogen, CN, and NO 2 ,
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, C 1-10 -alkyl, C 2-10 -alkenyl and C 2-10 -alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO 2 ,
R 2 , R 2′ and R 2″ are at each occurrence selected from the group consisting of hydrogen, unsubstituted C 1-30 -alkyl and halogen,
R is at each occurrence unsubstituted C 1-50 -alkyl, C 3-50 -alkenyl, or C 3-50 -alkynyl,
m is 0, 1, 2, 3 or 4, and
p is 2 to 1000.

2 . The polymer according to claim 1 , wherein:
R 2 , R 2′ and R 2″ are at each occurrence hydrogen, and R is at each occurrence C 1-36 -alkyl.

3 : The polymer of claim 1 , wherein:
L 2 is selected from the group from the group consisting of C 6-30 -arylene and 5 to 30 membered heteroarylene, and

C 6-30 -arylene and 5 to 30 membered heteroarylene can be substituted with one to six substituents R 3 at each occurrence 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,

can be substituted with one or two substituents R 4 at each occurrence 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,
R 31 , R 32 , R 41 and R 42 are independently from each other and at each occurrence 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,
C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be 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 can be replaced by O or S,
C 5-12 -cycloalkyl can be 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 i , 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 can be replaced by O, S, OC(O), CO, NR i or NR i —CO,
C 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 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

Assignees

• Basf Se
• Univ King Abdullah Sci & Tech

Inventors

• Chen Hu
• Zhang Weimin
• Hurhangee Michael
• Mcculloch Iain
• Hayoz Pascal
• Kaelblein Daniel

Classifications

• C08G2261/3246

  containing nitrogen and sulfur as heteroatoms · CPC title

• C08G2261/5222

  electrofluorescent · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• C08G2261/414

  Stille reactions · CPC title

• H01B1/127

  comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes · CPC title