Organic semiconducting compounds

Patent metadata

Field	Value
Publication number	US-11196005-B2
Application number	US-201716339573-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Oct 5, 2016
Publication date	Dec 7, 2021
Grant date	Dec 7, 2021

Abstract

The invention relates to a blend containing an electron acceptor and an electron donor, the acceptor being an n-type semiconductor which is a small molecule that does not contain a fullerene moiety, the electron donor being a p-type semiconductor which is a conjugated polymer comprising donor and acceptor units in random sequence, to a formulation containing such a blend, to the use of the blend in organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD and OLED devices comprising the blend.

First claim

The invention claimed is:

1. A blend containing an n-type organic semiconducting (OSC) compound which does not contain a fullerene moiety and contains a polycyclic electron donating core and attached thereto one or two terminal electron withdrawing groups, as shown in formula N

wherein w is 0 or 1,
and further containing a p-type OSC compound which is a conjugated copolymer comprising donor and acceptor units that are distributed in random sequence along the polymer backbone,
wherein the n-type OSC compound is selected from the following formulae

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
Ar 11 , Ar 12 , Ar 13 , Ar 32 , Ar 33 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
Ar 21 are, independently, arylene or heteroarylene that has from 6 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is substituted by one or more identical or different groups R 21 ,
wherein Ar 21 contains at least one benzene ring that is connected to U 2 ,

Ar 23 is

wherein the benzene ring is substituted by one or more identical or different groups R 1-4 ,

Ar 22 , Ar 26 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is substituted by one or more identical or different groups R 1-4 ,
Ar 41 is benzene or a group consisting of 2, 3 or 4 fused benzene rings, all of which are unsubstituted or substituted by one or more identical or different groups L,
Ar 42 is

Ar 43 is

wherein Ar 42 and Ar 43 have different meanings and Ar 42 is not a mirror image of Ar 43 ,

Ar 51 is benzene or a group consisting of 2, 3, or 4 fused benzene rings, all of which are unsubstituted or substituted by one or more identical or different groups R 1 , L or Z 1 ,
wherein Ar 51 is substituted by at least one groups R 1 , L or Z 1 that are selected from electron withdrawing groups,

Ar 52, 53 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups R 1 or L,
Ar 54,55 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups R 1 or L, or CY 1 ═CY 2 or —C≡C—,
Ar 4,5 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L, or CY 1 ═CY 2 or —C≡C—,
Ar 6,7 are, independently, arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
U 1 is CR 1 R 2 , SiR 1 R 2 , GeR 1 R 2 , NR 1 or C═O,
U 2 is CR 3 R 4 , SiR 3 R 4 , GeR 3 R 4 , NR 3 or C═O,
R 21 is one of the meanings given for R 1-4 ,
W 1 is S or Se,
W 2 is S or Se,
c, d are, independently, 0 or 1, wherein c+d≥1
h is 1, 2 or 3,
and
R 1-4 are, independently Z 1 , H, F, Cl, CN, or straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more CH 2 groups are optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —C(═O)—O—, —O—C(═O)—, —NR 0 —, —SiR 0 R 00 —, —CF 2 —, —CR 0 ═CR 00 —, —CY 1 ═CY 2 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, and in which one or more CH 2 or CH 3 groups are optionally replaced by a cationic or anionic group, or aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxy or heteroaryloxy, wherein each of the aforementioned cyclic groups has 5 to 20 ring atoms, is mono- or polycyclic, does optionally contain fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
and the pair of R 1 and R 2 together with the C, Si or Ge atom to which they are attached, may also form a spiro group with 5 to 20 ring atoms which is mono- or polycyclic, does optionally contain fused rings, and is unsubstituted or substituted by one or more identical or different groups L,

Z 1 is an electron withdrawing group,
R T1,T2 are, independently, H, a carbyl or hydrocarbyl group with 1 to 30 C atoms that is optionally substituted by one or more groups L and optionally comprises one or more hetero atoms,
wherein at least one of R T1 and R T2 is an electron withdrawing group,

Y 1,2 are, independently, H, F, Cl or CN,
L is F, Cl, —NO 2 , —CN, —NC, —NCO, —NCS, —OCN, —SCN, R 0 , OR 0 , SR 0 , —C(═O)X 0 , —C(═O)R 0 , —C(═O)—OR 0 , —O—C(═O)—R 0 , —NH 2 , —NHR 0 , —NR 0 R 00 , —C(═O)NHR 0 , —C(═O)NR 0 R 00 , —SO 3 R 0 —SO 2 R 0 , —OH, —NO 2 —CF 3 —SF 5 , or optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 30 C atoms that is optionally substituted and optionally comprises one or more hetero atoms,
R 0 , R 00 are independently, H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X 0 is halogen,
a and b are independently 0, 1, 2 or 3, and
wherein the p-type conjugated OSC polymer is selected from the following formulae

Assignees

• Raynergy Tek Inc

Inventors

• Mitchell William
• Blouin Nicolas

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/151

  Copolymers · CPC title

• C08G61/123 Primary

  derived from five-membered heterocyclic compounds · CPC title

• C08G2261/91

  Photovoltaic applications · CPC title