Organic semiconducting compounds

Patent metadata

Field	Value
Publication number	US-11289663-B2
Application number	US-201816492377-A
Country	US
Kind code	B2
Filing date	Mar 6, 2018
Priority date	Mar 9, 2017
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

The invention relates to novel organic semiconducting compounds containing a π-extended ω-disubstituted dicyanomethylene quinoid structure, 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
one of U 11 and U 12 is a C═C double bond and the other is CR 1 R 2 ,
one of U 21 and U 22 is a C═C double bond and the other is CR 3 R 4 ,
Ar 1-5 , Ar 4 , Ar 5 a quinoidal alicyclic or heterocyclic group that has 5 to 30 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 2 and Ar 3 are selected from the following formulae and their mirror images:

X O, S, Se or Te,
R, R′ One of the meanings of R 1 of L as defined for formula I,
# an sp 2 carbon that is linked to the adjacent group in formula I via a C═C double bond, and
* an sp 2 carbon atom that is linked to the adjacent group in formula I via a C—C single bond,
Z, Z′ O, S, C(═O), NR, ═N— or ═CR—, wherein at least one of Z and Z′ is different from ═N— and ═CR—,
Ar x , Ar y a fused 5- or 6-membered aromatic ring wherein one or more CH groups are optionally replaced by —O—, —S—, Se, Te, ═N—, —NR— or —C(═O)—, and one or more H atoms are optionally replaced by R 1 or L,
Y CR 1 R 2 , SiR 1 R 2 , GeR 1 R 2 , NR, C(═O) or S(═O),
R 1-4 H, F, Cl, CN, straight-chain, branched or cyclic alkyl with 1 to 40 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 straight-chain, branched or cyclic silyl with 1 to 40 Si atoms,
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,

L 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 with 1 to 20 Si atoms, 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 H or straight-chain or branched alkyl with 1 to 40 C atoms that is optionally fluorinated,
X 0 halogen,
a, b 0 or an integer from 1 to 10.

2. The compound according to claim 1 , which is selected from the following formulae

wherein Ar 1-5 , U 11 , U 21 , U 22 , a, b have the meanings for formula I, and Ar 11 and Ar 12 have one of the meanings given for Ar 1 .

3. The compound according to claim 1 , wherein Ar 1 in formula I is selected from the following formulae and their mirror images:

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
X O, S, Se or Te,
R, R′ one of the meanings of R 1 or L as defined for formula I,
# an sp 2 carbon atom that is linked to the adjacent group in formula I via a C═C double bond, and
* an sp 2 carbon atom that is linked to the adjacent group in formula I via a C—C single bond,
Z, Z′ O, S, C(═O), NR, ═N— or ═CR—, wherein at least one of Z and Z′ is different from ═N— and ═CR—.

4. The compound according to claim 1 , wherein Ar 1 in formula I are selected from the following formulae and their mirror images:

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
X O, S, Se or Te,
R One of the meanings of R 1 of L as defined for formula I,
# an sp 2 carbon that is linked to the adjacent group in formula I via a C═C double bond, and
* an sp 2 carbon atom that is linked to the adjacent group in formula I via a C—C single bond,
Z, Z′ O, S, C(═O), NR, ═N— or ═CR—, wherein at least one of Z and Z′ is different from ═N— and ═CR—,
Ar x , Ar y a fused 5- or 6-membered aromatic ring wherein one or more CH groups are optionally replaced by —O—, —S—, Se, Te, ═N—, —NR— or —C(═O)—, and one or more H atoms are optionally replaced by R 1 or L,
Y CR 1 R 2 , SiR 1 R 2 , GeR 1 R 2 , NR, C(═O) or S(═O),
with L, R 1 and R 2 being as defined for formula I.

5. The compound according to claim 1 , wherein Ar 4 and Ar 5 are selected from the following formulae and their mirror images:

Y′ denotes N or CR
X O, S, Se or Te,
R, R′ One of the meanings of R 1 of L as defined for formula I,
# an sp 2 carbon that is linked to the adjacent group in formula I via a C═C double bond, and
* an sp 2 carbon atom that is linked to the adjacent group in formula I via a C═C single bond,
Z, Z′ O, S, C(═O), NR, ═N— or ═CR—, wherein at least one of Z and Z′ is different from ═N— and ═CR—,
Ar x , Ar y a fused 5- or 6-membered aromatic ring wherein one or more CH groups are optionally replaced by —O—, —S—, Se, Te, ═N—, —NR— or —C(═O)—, and one or more

Assignees

• Raynergy Tek Inc

Inventors

• Wang Changsheng
• Mitchell William

Classifications

• H10K85/50

  Organic perovskites; Hybrid organic-inorganic perovskites [HOIP], e.g. CH3NH3PbI3 · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/6576

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

• C07D495/04 Primary

  Ortho-condensed systems · CPC title