Organic semiconducting compounds

Patent metadata

Field	Value
Publication number	US-11637246-B2
Application number	US-201715733303-A
Country	US
Kind code	B2
Filing date	Dec 21, 2017
Priority date	Dec 21, 2017
Publication date	Apr 25, 2023
Grant date	Apr 25, 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 selected from formulae IA and IB

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
one of Z 1 and Z 2 is O or S and the other is CR 1 R 2 , SiR 1 R 2 or C═CR 1 R 2 ,
one of Z 3 and Z 4 is O or S and the other is CR 1 R 2 , SiR 1 R 2 or C═CR 1 R 2 ,
wherein Z 2 and Z 3 are not at the same time O,
Ar 1 is selected from the following formulae

Ar 2 , Ar 3 are trivalent arylene or heteroarylene which has from 5 to 20 ring atoms, which is mono- or polycyclic, which optionally contains fused rings, and which is unsubstituted or substituted by one or more identical or different groups L, or CY 1 ═CY 2 or —C≡C—,
Ar 4-7 are divalent arylene or heteroarylene which has from 5 to 20 ring atoms, which is mono- or polycyclic, which optionally contains fused rings, and which is unsubstituted or substituted by one or more identical or different groups L, or CY 1 ═CY 2 or —C≡C—,
Y 1 , Y 2 are H, F, Cl or CN,
W 1 , W 2 , W 3 are S, O, Se or C═O,
W 4 is S, O or NR 0 ,
R 1 , R 2 are R W , 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 each 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 each optionally replaced by F, Cl, Br, I or CN, and in which one or more CH 2 or CH 3 groups are each 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, optionally contains 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 or Si atom to which they are attached, may also form a spiro group with 5 to 20 ring atoms which is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
R 5-8 are 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 each 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 each optionally replaced by F, Cl, Br, I or CN, and in which one or more CH 2 or CH 3 groups are each 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, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
R W is an electron withdrawing group,
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, —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,
R T1 , R T2 are each independently selected from the group consisting of the following formulae

R a , R b are aryl or heteroaryl, each having from 4 to 30 ring atoms, optionally containing fused rings and being unsubstituted or substituted with one or more groups L, or one of the meanings given for L,
R*, R**, R*** are alkyl with 1 to 20 C atoms which is straight-chain, branched or cyclic, and is unsubstituted, or substituted with one or more F or Cl atoms or CN groups, or perfluorinated, and in which one or more C atoms are optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —SiR 0 R 00 —, —NR 0 R 00 —, —CHR 0 ═CR 00 — or —C≡C— such that O- and/or S-atoms are not directly linked to each other,
L′ is H or one of the meanings of L,
Y 1 , Y 2 are H, F, Cl or CN,
r is 0, 1, 2, 3 or 4,
s is 0, 1, 2, 3, 4 or 5,
t is 0, 1, 2 or 3,
u is 0, 1 or 2,

a, b are 0, 1, 2 or 3,
c, d are 0, 1, 2 or 3,
m is 1, 2 or 3,
k is 1, 2 or 3.

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

wherein R 1 , R 2 , R T1 , R T2 , Ar 1-5 , a, b and m have the meanings given in claim 1 , and Z 1 and Z 4 are independently of each other O or S.

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

wherein R 0 and R 5-8 have the meanings given in claim 1 .

4. The compound according to claim 1 , characterized in that Ar 2 is on each occurrence identically or differently selected from the following formulae and their mirror images

wherein W 1 , W 2 , W 3 , R 3-8 have the meanings given in claim 1 , V 1 is CR 3 or N, and R 3 has one of the meanings given for R 5 in claim 1 .

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

Assignees

• Raynergy Tek Inc
• Univ Beijing

Inventors

• Pron Agnieszka
• Huaulme Quentin
• Mitchell William
• D'Lavari Mansoor
• Zhan Xiaowei
• Wang Wei
• Cai Guilong

Classifications

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K30/30

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

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D495/22 Primary

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