Organic semiconducting compounds

Patent metadata

Field	Value
Publication number	US-11839155-B2
Application number	US-201917042662-A
Country	US
Kind code	B2
Filing date	Mar 26, 2019
Priority date	Mar 28, 2018
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

The invention relates to novel organic semiconducting compounds containing a polycyclic unit, to methods for their preparation and educts or intermediates used therein, to compositions, polymer blends and formulations containing them, to the use of the compounds, compositions and polymer blends as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD, OFET and OLED devices comprising these compounds, compositions or polymer blends.

First claim

The invention claimed is:

1. A compound of formula I

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
Ar 1 , Ar 2 are a group selected from the following formulae

Ar 3 is a group selected from the following formulae and their mirror images

Ar 4 is a group selected from the following formulae and their mirror images

Ar 5 is a group selected from the following formulae and their mirror images

Ar 6,7 are 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 S , or CY 1 ═CY 2 or —C≡C—,
U 1 , U 2 are CR 1 R 2 , SiR 1 R 2 , GeR 1 R 2 , C═CR 1 R 2 , NR 1 or C═O,
V 1 is CR 3 or N,
W 1 , W 2 , W 3 are S, O, Se or C═O,
W 4 is S, O, Se, C═O or NR 1 ,
R 1-9 is 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 S ,
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 S ,

R T1 , R T2 are an electron withdrawing group,
Y 1 , Y 2 are H, F, Cl or CN,
L S 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 H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X 0 is halogen,
a, b are 0 or an integer from 1 to 10,
k is an integer from 1 to 10,
m is 0 or an integer from 1 to 10,
wherein at least one of R T1 and R T2 is an electron withdrawing group of formula TG

Ar 8 is bi- or polycyclic arylene or heteroarylene having from 5 to 20 ring atoms which is optionally substituted with one or more groups L,
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 ,
Z 1 , Z 2 are O or C(CN) 2 ,
and wherein at least one group Ar 3 denotes thieno[3,2-b]thiophene and/or at least one of the groups Ar 4 and Ar 5 denotes thieno[3,2-b]thiophene that is optionally substituted with R 3 .

2. The compound according to claim 1 , characterized in that it is selected from the following subformulae

wherein U 1 , U 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , R T1 , R T2 , a and b, independently of each other and on each occurrence identically or differently, have the meanings given in claim 1 .

3. The compound according to claim 1 , characterized in that the groups Ar 3 are on each occurrence identically or differently selected from the following formulae and their mirror images

wherein R 5-8 have the meanings given in claim 1 .

4. The compound according to claim 1 , characterized in that the groups Ar 4 are on each occurrence identically or differently selected from the following formulae and their mirror images

wherein R 3-9 have the meanings given in claim 1 .

5. The compound according to claim 1 , characterized in that the groups Ar 5 are on each occurrence identically or differently selected from the following formulae and their mirror images

wherein R 3-9 have the meanings given in claim 1 .

6. The compound according to claim 1 , characterized in that the groups Ar 6 and Ar 7 are on each occurrence identically or differently selected from the following formulae and their mirror images

wherein, independently of each other and on each occurrence identically or differently, V 2 is CR 4 or N.

7. The compound according to claim 1 , characterized in that the groups Ar 6 and Ar 7 are on each occurrence identically or differently selected from the following formulae and their mirror images

wh

Assignees

• Raynergy Tek Inc

Inventors

• Mitchell William
• Pron Agnieszka
• D'Lavari Mansoor
• Heard Kane
• Snow Jonathan
• Burgues Ignasi
• Huaulme Quentin

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/6576 Primary

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D495/22

  in which the condensed system contains four or more hetero rings · CPC title

• H10K85/211

  Fullerenes, e.g. C60 · CPC title