Semiconducting polymer

Patent metadata

Field	Value
Publication number	US-10815236-B2
Application number	US-201716080166-A
Country	US
Kind code	B2
Filing date	Feb 27, 2017
Priority date	Feb 29, 2016
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

Compounds of formula (I) and polymers comprising at least a structure of formula (II), wherein T 1 or T 2 are independently of each other a group of Formula (III), Formula (iv) Q a , Q b , Q c , Q d , Q e or Q f are independently of each other O, S or NR 1 .

First claim

The invention claimed is:

1. A polymer, consisting of unit having a structure of formula (II′)

wherein
Q a , Q b , Q c and Q d are independently O, S or an NR 1 group,
Ar and Ar′ are independently selected from the group consisting of

each Y, Y′, Y″ and Y* is independently O, S, an NR 1a group, Se, or Te, and
each R W is independently H, a C 1-30 -alkyl group, a C 1-30 -alkoxy group, or a moiety

R s1 , R s2 and R s3 are independently H, a C 1-20 -alkyl group, a C 2-20 -alkenyl group, or a phenyl group,
Ar or Ar′ is bound via the single bonds and to the moieties

Q is Q a , Q b , Q c or Q d ,
Ar and/or Ar′ optionally comprise a substituent R 2 ,
each R 1 and R 1a is independently selected from the group consisting of H, a C 1-100 -alkyl group, a C 2-100 -alkenyl group, a C 2-100 -alkynyl group, a C 5-12 -cycloalkyl group, a C 6-18 -aryl group, a 5 to 20 membered heteroaryl group, a C(O)—C 1-100 -alkyl group, a C(O)—C 5-12 -cycloalkyl group and a C(O)—OC 1-100 -alkyl group,
the C 1-100 -alkyl group, the C 2-100 -alkenyl group and the C 2-100 -alkynyl group optionally comprise one to forty substituents independently selected from the group consisting of a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an OR a group, an OC(O)—R a group, a C(O)—OR a group, a C(O)—R a group, an NR a R b group, an NR a —C(O)R b group, a C(O)—NR a R b group, an N[C(O)R a ][C(O)R b ] group, an SR a group, an Si(R Sia )(R Sib )(R Sic ) group, an —O—Si(R Sia )(R Sib )(R Sic ) group, a halogen, CN, and NO 2 ,
at least two CH 2 -groups, but not adjacent CH 2 -groups, of the C 1-100 -alkyl group, the C 2-100 -alkenyl group and/or the C 2-100 -alkynyl group can be replaced by O or S,
the C 5-12 -cycloalkyl group optionally comprises one to six substituents independently selected from the group consisting of a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an OR a group, an OC(O)—R a group, a C(O)—OR a group, a C(O)—R a group, an NR a R b group, an NR a —C(O)R b group, a C(O)—NR a R b group, an N[C(O)R a ][C(O)R b ] group, an SR a group, an Si(R Sia )(R Sib )(R Sic ) group, an —O—Si(R Sia )(R Sib )(R Sic ) group, a halogen, CN, and NO 2 ,
one or two CH 2 -groups, but not adjacent CH 2 -groups, of the C 5-12 -cycloalkyl group can be replaced by O, S, OC(O), CO, an NR a group or an NR a —CO group,
the C 6-18 -aryl group and the 5 to 20 membered heteroaryl group optionally comprise one to six substituents independently selected from the group consisting of a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an OR a group, an OC(O)—R a group, a C(O)—OR a group, a C(O)—R a group, an NR a R b group, an NR a —C(O)R b group, a C(O)—NR a R b group, an N[C(O)R a ][C(O)R b ] group, an SR a group, an Si(R Sia )(R Sib )(R Sic ) group, an —O—Si(R Sia )(R Sib )(R Sic ) group, a halogen, CN, and NO 2 ,
R a and R b are independently selected from the group consisting of H, a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group and a 5 to 14 membered heteroaryl group,
R Sia , R Sib and R Sic are independently selected from the group consisting of H, a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an O—C 1-60 -alkyl group, an O—C 2-60 -alkenyl group, an O—C 2-60 -alkynyl group, an O—C 5-8 -cycloalkyl group, an O—C 6-14 -aryl group, an O-5 to 14 membered heteroaryl group, an —[O—SiR Sid R Sie ] o —R Sif group, an NR 5 R 6 group, a halogen and an O—C(O)—R 5 group,
o is an integer from 1 to 50,
R Sid , R Sie , R Sif are independently selected from the group consisting of H, a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an O—C 1-60 -alkyl group, an O—C 2-60 -alkenyl group, an O—C 2-60 -alkynyl group, an O—C 5-8 -cycloalkyl group, an O—C 6-14 -aryl group, an O-5 to 14 membered heteroaryl group, an —[O—SiR Sig R Sih ] p —R Sii group, an NR 50 R 60 group, a halogen and an O—C(O)—R 50 group,
p is an integer from 1 to 50,
R Sig R Sih , R Sii are independently selected from the group consisting of H, a C 1-30 -alkyl group, a C 2-30 -alkenyl group, a C 2-30 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an O—C 1-30 -alkyl group, an O—C 2-30 -alkenyl group, an O—C 2-30 -alkynyl group, an O—C 5-6 -cycloalkyl group, an O—C 6-10 -aryl group, an O-5 to 10 membered heteroaryl group, an O—Si(CH 3 ) 3 group, an NR 500 R 600 group, a halogen and an O—C(O)—R 500 group,
R 5 , R 6 , R 50 , R 60 , R 500 and R 600 are independently selected from the group consisting of H, a C 1-60 -alkyl group, a C 2-60 -alkenyl group, a C 2-60 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, and a 5 to 14 membered heteroaryl group,
the C 1-60 -alkyl group, the C 2-60 -alkenyl group and the C 2-60 -alkynyl group optionally comprise one to twenty substituents selected from the group consisting of a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, an OR c group, an OC(O)—R c group, a C(O)—OR c group, a C(O)—R c group, an NR c R d group, an NR c —C(O)R d group, a C(O)—NR c R d group, an N[C(O)R c ][C(O)R d ] group, an SR c group, an Si(R Sij )(R Sik )(R Sil ) group, an —O—Si(R Sij )(R Sik )(R Sil ) group, a halogen, CN, and NO 2 ,
at least two CH 2 -groups, but not adjacent CH 2 -groups, of the C 1-60 -alkyl group, the C 2-60 -alkenyl group and/or the C 2-60 -alkynyl group can be replaced by O or S,
the C 5-8 -cycloalkyl group optionally comprises one to five substituents selected from the group consisting of a C 1-30 -alkyl group, a C 2-30 -alkenyl group, a C 2-30 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, an OR group, an OC(O)—R c group, a C(O)—OR c group, an C(O)—R c group, an NR c R d group, an NR c —C(O)R d group, a C(O)—NR c R d group, an N[C(O)R c ][C(O)R d ] group, an SR c group, an Si(R Sij )(R Sik )(R Sil ) group, an —O—Si(R Sij )(R Sik )(R Sil ) group, a halogen, CN, and NO 2 ,
one or two CH 2 -groups, but not adjacent CH 2 -groups, of the C 5-8 -cycloalkyl group can be replaced by O, S, OC(O), CO, an NR group or an NR c —CO group,
the C 6-14 -aryl group and the 5 to 14 membered heteroaryl group optionally comprise one to five substituents independently selected from the group consisting of a C 1-30 -alkyl group, a C 2-30 -alkenyl group, a C 2-30 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, an OR group, an OC(O)—R c group, a C(O)—OR c group, a C(O)—R c group, an NR c R d group, an NR c —C(O)R d group, a C(O)—NR c R d group, an N[C(O)R c ][C(O)R d ] group, an SR c group, an Si(R Sij )(R Sik )(R Sil ) group, an —O—Si(R Sij )(R Sik )(R Sil ) group, a halogen, CN and NO 2 ,
R c and R d are independently selected from the group consisting of

Assignees

• Basf Se

Inventors

• Flores Jean-Charles
• Hayoz Pascal
• Mcculloch Iain
• Onwubiko Nkechinyerem
• Kaelblein Daniel
• Yue wan
• Chen Hung-Yang
• Knall Astrid-Caroline

Classifications

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B57/004

  Diketopyrrolopyrrole dyes · CPC title

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C09B69/109

  containing other specific dyes · CPC title