IP Library › Granted Patent US 10,815,236

Granted Patent B2

US 10,815,236 · App. 16/080,166 · Granted Oct 27, 2020

Semiconducting polymer

Inventors: Jean-Charles Flores (Basel, CH); Pascal Hayoz (Basel, CH); Iain McCulloch (Eastleigh, GB); Nkechinyerem Onwubiko (London, GB); Daniel Kaelblein (Ludwigshafen, DE); Wan Yue (Guangzhou, CN); Hung-Yang Chen (Somerset, NJ); Astrid-Caroline Knall (London, GB)

C07D487/04 C09B57/00 C09B57/004 C09B69/109 H01L51/0034 H01L51/0508 C08G2261/3223

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Quick Facts

Patent No.: US 10,815,236
App. No.: 16/080,166
Granted: Oct 27, 2020
Kind: B2

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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 .

Claims (134)

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 H, a C 1-30 -alkyl group, a C 2-30 -alkenyl group and a C 2-30 -alkynyl group,

R Sij , R Sik and R Sil 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 OC 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—SiR Sim R Sin ] q —R Sio group, an NR 7 R 8 group, a halogen, and an O—C(O)—R 7 group,

q is an integer from 1 to 50,

R Sim , R Sin , R Sio 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 OC 6-10 -aryl group, an O-5 to 10 membered heteroaryl group, an —[O—SiR Sip R Siq ] r —R Sir group, an NR 70 R 80 group, a halogen, and an O—C(O)—R 70 group,

r is an integer from 1 to 50,

R Sip , R Siq , R Sir 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 OC 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 700 R 800 group, a halogen and an O—C(O)—R 700 group,

R 7 , R 8 , R 70 , R 80 , R 700 and R 800 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, and a 5 to 10 membered heteroaryl group,

the C 1-30 -alkyl group, the C 2-30 -alkenyl group and the C 2-30 -alkynyl group optionally comprise one to ten substituents selected from the group consisting of a halogen, CN and NO 2 ,

each R 2 is 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 5-12 -cycloalkyl group, a C 6-18 -aryl group, a 5 to 20 membered heteroaryl group, an OR 21 group, an OC(O)—R 21 group, a C(O)—OR 21 group, a C(O)—R 21 group, an NR 21 R 22 group, an NR 21 —C(O)R 22 group, a C(O)—NR 21 R 22 group, an N[C(O)R 21 ][C(O)R 22 ] group, an SR 21 group, a halogen, CN, an SiR Sis R Sit R Sin group and OH,

R 21 and R 22 and 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 5-12 -cycloalkyl group, a C 6-18 -aryl group and a 5 to 20 membered heteroaryl group,

the C 1-30 -alkyl group, the C 2-30 -alkenyl group and the C 2-30 -alkynyl group optionally comprise one to ten 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 e group, an OC(O)—R e group, a C(O)—OR e group, a C(O)—R e group, an NR e R f group, an NR e —C(O)R f group, a C(O)—NR e R f group, an N[C(O)R e ][C(O)R f ] group, an SR e group, a halogen, CN, an SiR Sis R Sit R Siu group and NO 2 ,

at least two CH 2 -groups, but not adjacent CH 2 -groups, of the C 1-30 -alkyl group, the C 2-30 -alkenyl group and/or the C 2-30 -alkynyl group can be replaced by O or S,

the C 5-12 -cycloalkyl optionally comprises one to six substituents independently selected from the group consisting of a C 1-20 -alkyl group, a C 2-20 -alkenyl group, a C 2-20 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an OR e group, an OC(O)—R e group, a C(O)—OR e group, a C(O)—R e group, an NR e R f group, an NR e —C(O)R f group, a C(O)—NR e R f group, an N[C(O)R e ][C(O)R f ] group, an SR e group, a halogen, CN, an SiR Sis R Sit R Siu group 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 e group or an NR e —CO group, and

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 1-20 -alkyl group, a C 2-20 -alkenyl group, a C 2-20 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, a 5 to 14 membered heteroaryl group, an OR e group, an OC(O)—R e group, a C(O)—OR e group, a C(O)—R e group, an NR e R f group, an NR e —C(O)R f group, a C(O)—NR e R f group, an N[C(O)R e ][C(O)R f ] group, an SR e group, a halogen, CN, an SiR Sis R Sit R Siu group and NO 2 ,

R Sis , R Sit and R Siu are independently selected from the group consisting of H, a C 1-20 -alkyl group, a C 2-20 -alkenyl group, a C 2-20 -alkynyl group, a C 5-6 -cycloalkyl group, a phenyl group and an O—Si(CH 3 ) 3 group,

R e and R f are independently selected from the group consisting of H, a C 1-20 -alkyl group, a C 2-20 -alkenyl group, a C 2-20 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, and a 5 to 14 membered heteroaryl group,

the C 1-20 -alkyl group, the C 2-20 -alkenyl group and the C 2-20 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR g group, an OC(O)—R g group, a C(O)—OR g group, a C(O)—R g group, an NR g R h group, an NR g —C(O)R h group, a C(O)—NR g R h group, an N[C(O)R g ][C(O)R h ] group, an SR g group, a halogen, CN, and NO 2 ,

the C 5-8 -cycloalkyl group optionally comprises one to five substituents selected from the group consisting of a C 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR g group, an OC(O)—R g group, a C(O)—OR group, a C(O)—R group, an NR g R h group, an NR g —C(O)R h group, a C(O)—NR g R h group, an N[C(O)R g ][C(O)R h ] group, an SR g group, a halogen, CN, and NO 2 ,

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 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR g group, an OC(O)—R group, a C(O)—OR g group, a C(O)—R group, an NR g R h group, an NR g —C(O)R h group, a C(O)—NR g R h group, an N[C(O)R g ][C(O)R h ] group, an SR g group, a halogen, CN, and NO 2 ,

R g and R h are independently selected from the group consisting of H, a C 1-10 -alkyl group, a C 2-10 -alkenyl group and a C 2-10 -alkynyl group,

the C 1-10 -alkyl group, the C 2-10 -alkenyl group and the C 2-10 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a halogen, CN and NO 2 ,

each R 100 and R 101 is independently selected from the group consisting of H, a C 1-20 -alkyl group, a C 2-20 -alkenyl group, a C 2-20 -alkynyl group, a C 5-8 -cycloalkyl group, a C 6-14 -aryl group, and a 5 to 14 membered heteroaryl group; or wherein R 100 and R 101 , if attached to a same atom, together with the same atom, form a 5 to 12 membered ring system,

the C 1-20 -alkyl group, the C 2-20 -alkenyl group and the C 2-20 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R q group, a C(O)—OR q group, a C(O)—R q group, an NR q R r group, an NR q C(O)R r group, a C(O)—NR g R r group, an N[C(O)R q ][C(O)R r ] group, an SR q group, a halogen, CN, and NO 2 ,

the C 5-8 -cycloalkyl group optionally comprises one to five substituents selected from the group consisting of a C 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R q group, a C(O)—OR q group, a C(O)—R q group, an NR q R r group, an NR q —C(O)R r group, a C(O)—NR q R r group, an N[C(O)R q ][C(O)R r] group, an SR q group, a halogen, CN, and NO 2 ,

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 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R g group, a C(O)—OR g group, a C(O)—R g group, an NR q R r group, an NR q —C(O)R r group, a C(O)—NR q R r group, an N[C(O)R q ][C(O)R r ] group, a SR q group, a halogen, CN, and NO 2 ,

the 5 to 12 membered ring system optionally comprises one to five substituents selected from the group consisting of a C 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R g group, a C(O)—OR g group, a C(O)—R g group, an NR q R r group, an NR q —C(O)R r group, a C(O)—NR q R r group, an N[C(O)R q ][C(O)R r ] group, an SR q group, a halogen, CN, and NO 2 ,

R q and R r are independently selected from the group consisting of H, a C 1-10 alkyl group, a C 2-10 -alkenyl group and a C 2-10 -alkynyl group, the C 1-10 -alkyl group, the C 2-10 -alkenyl group and the C 2-10 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a halogen, CN and NO 2 , and

n is in a range from 3 to 1000.

2. The polymer of claim 1 , wherein Ar and Ar′ are independently selected from the group consisting of

3. The polymer of claim 1 , wherein Ar and Ar′ are independently selected from the group consisting of

4. The polymer of claim 1 , consisting of units having a structure of formula 1′, 2′ or 3′

wherein R 1b , R 1c and R 1d are independently defined as R 1a .

5. A polymer consisting of units having a a structure of formula II″

Q a and Q b are independently O, S or an NR 1 group,

Ar is selected from the group consisting of:

each Y, Y′, Y″ and Y* is independently O, S, and NR 1a group, Se, or Te, and

each R W is independently H, a C 1-20 -alkyl group, a C 1-30 -alkoxy group, or a moiety:

R a1 , R a2 and R a3 are independently H, a C 1-20 -alkyl group, a C 2-20 -alkenyl group or a phenyl group,

Ar or Ar′ is bound viathe 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 ,

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,

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,

o is an integer from 1 to 50,

p is an integer from 1 to 50,

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,

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,

R c and R d are independently selected from the group consisting of H, a C 1-30 -alkyl group, a C 2-30 -alkenyl group and a C 2-30 -alkynyl group,

R Sij , R Sik and R Sil 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—SiR Sim R Sin ] q —R Sio group, an NR 7 R 8 group, a halogen, and an O—C(O)—R 7 group,

q is an integer from 1 to 50,

R Sim , R Sin , R Sio 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—SiR Sip R Siq ] r —R Sir group, an NR 70 R 80 group, a halogen, and an O—C(O)—R 70 group,

r is an integer from 1 to 50,

R Sip , R Siq , R Sir 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 700 R 800 group, a halogen and an O—C(O)—R 700 group,

the C 1-30 -alkyl group, the C 2-30 -alkenyl group and the C 2-30 -alkynyl group optionally comprise one to ten substituents selected from the group consisting of a halogen, CN and NO 2 ,

at least two CH 2 -groups, but not adjacent CH 2 -groups, of the C 1-30 -alkyl group, the C 2-30 -alkenyl group and/or the C 2-30 -alkynyl group can be replaced by O or S,

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 e group or an NR e —CO group,

R g and R h are independently selected from the group consisting of H, a C 1-10 -alkyl group, a C 2-10 -alkenyl group and a C 2-10 -alkynyl group,

the C 1-10 -alkyl group, the C 2-10 -alkenyl group and the C 2-10 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a halogen, CN and NO 2 ,

the C 1-20 -alkyl group, the C 2-20 -alkenyl group and the C 2-20 -alkynyl group optionally comprise one to five substituents selected from the group consisting of a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R q group, a C(O)—OR q group, a C(O)—R q group, an NR q R r group, an NR q C(O)R r group, a C(O)—NR g R r group, an N[C(O)R q ][C(O)R r ] group, an SR q group, a halogen, CN, and NO 2 ,

the C 5-8 -cycloalkyl group optionally comprises one to five substituents selected from the group consisting of a C 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R q group, a C(O)—OR q group, a C(O)—R q group, an NR q R r group, an NR q —C(O)R r group, a C(O)—NR q R r group, an N[C(O)R q ][C(O)R r] group, an SR q group, a halogen, CN, and NO 2 ,

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 1-10 -alkyl group, a C 2-10 -alkenyl group, a C 2-10 -alkynyl group, a C 5-6 -cycloalkyl group, a C 6-10 -aryl group, a 5 to 10 membered heteroaryl group, an OR q group, an OC(O)—R g group, a C(O)—OR g group, a C(O)—R g group, an NR q R r group, an NR q —C(O)R r group, a C(O)—NR q R r group, an N[C(O)R q ][C(O)R r ] group, a SR q group, a halogen, CN, and NO 2 ,

m is in a range from 3 to 1000.

6. The polymer of claim 5 , consisting of units haing a structure of formula 4′

R 1b is independently defined as R 1a , and

m is in a range from 3 to 1000.

7. A process for preparing the polymer of claim 1 , the process comprising condensing a tetraone A and a dione B:

wherein Q a , Q b , Q c , Q d , Ar and Ar′ are as defined in claim 1 .

8. The process of claim 7 , wherein:

Q a and Q b are an NR 1 group, and

Q c and Q d are O or an NR 1 group.

9. A process for preparing the polymer of claim 5 , the process comprising homopolymerizing a tetraone A:

10. An electronic device comprising the polymer of claim 1 .

11. The electronic device of claim 10 , wherein the electronic device is an organic field effect transistor.

12. A polymer consisting of units having a formula selected from P1 to P11:

wherein:

n is an integer from 3 to 1000.

13. polymer consisting of units having a formula selected from P12 to P14:

wherein:

m is an integer from 3 to 1000.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2020

From: BASF SE

To: CLAP CO., LTD.

Reel/Frame 052459/0201 →

Priority Claims (2)

EP 16157844 · Feb 29, 2016 · regional

EP 16207316 · Dec 29, 2016 · regional

Continuity (1)

Related Publication 20190048015A1 · Feb 14, 2019