Carbazole derivates for use in optoelectronic devices

Patent metadata

Field	Value
Publication number	US-2022131080-A1
Application number	US-201917294453-A
Country	US
Kind code	A1
Filing date	Nov 8, 2019
Priority date	Nov 16, 2018
Publication date	Apr 28, 2022
Grant date	—

Abstract

The invention relates to an organic molecule, in particular for use in organic optoelectronic devices. According to the invention, the organic molecule has a structure of Formula Iwhereinn is 1 or 2; andX is selected from the group consisting of H, SiMe3, SiPh3, CN, and CF3.

First claim

1 . An organic molecule comprising a structure of Formula I:

wherein
n is 1 or 2;
X is selected from the group consisting of H, SiMe 3 , SiPh 3 , CN, and CF 3 ;
Ar EWG is selected from the group consisting of Formulas IIa to IIo:

wherein # represents the binding site of the single bond shown in Formula I, which connects Ar EWG to the phenyl ring;
R 1 is selected independently of one another at each occurrence from the group consisting of
hydrogen,
deuterium,
C 1 -C 5 alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and

C 6 -C 18 aryl,
which is optionally substituted with one or more substituents R 6 ;

R 2 is selected independently of one another at each occurrence from the group consisting of
hydrogen,
deuterium,
C 1 -C 5 alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and

C 6 -C 18 aryl,
which is optionally substituted with one or more substituents R 6 ;

R d is selected independently of one another at each occurrence from the group consisting of hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I,
C 1 -C 40 alkyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 1 -C 40 alkoxy,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 1 -C 40 thioalkoxy,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 2 -C 40 alkenyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 2 -C 40 alkynyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 6 -C 60 aryl,
which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 57 heteroaryl,
which is optionally substituted with one or more substituents R 6 ;

R a is selected independently of one another at each occurrence from the group consisting of R A ,
hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I,
C 1 -C 40 alkyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 1 -C 40 alkoxy,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 1 -C 40 thioalkoxy,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 2 -C 40 alkenyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 2 -C 40 alkynyl,
which is optionally substituted with one or more substituents R 6 , and
wherein one or more non-adjacent CH 2 groups are optionally substituted by R 6 C═CR 6 , C═C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S, or CONR 6 ;

C 6 -C 60 aryl,
which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 57 heteroaryl,
which is optionally substituted with one or more substituents R 6 ;

R 6 is selected independently of one another at each occurrence from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F,
C 1 -C 5 alkyl,
wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, CN, CF 3 , or F;

C 1 -C 5 alkoxy,
wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, CN, CF 3 , or F;

C 1 -C 5 thioalkoxy,
wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, CN, CF 3 , or F;

C 2 -C 5 alkenyl,
wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, CN, CF 3 , or F;

C 2 -C 5 alkynyl,
wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, CN, CF 3 , or F;

C 6 -C 18 aryl,
which is optionally substituted with one or more C 1 -C 5 alkyl substituents;

C 3 -C 17 heteroaryl,
which is optionally substituted with one or more C 1 -C 5 alkyl substituents;

N(C 6 -C 18 aryl) 2 ;
N(C 3 -C 17 heteroaryl) 2 ,
and N(C 3 -C 17 heteroaryl)(C 6 -C 18 aryl);
R A is selected independently of one another at each occurrence from a chemical structure of Formula IIA

or a chemical structure of Formula IIB

wherein R N is selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph;
wherein $ represents the binding site of a single bond;
wherein at least one substituent R a is R A ;
wherein R B is selected from the group consisting of
H,
Ph,
CN,
CF 3 ,
of a chemical structure of Formula IIA-2

or a chemical structure of Formula IIB-2

where

Assignees

• Cynora Gmbh

Inventors

• Danz Michael
• Thirion Damien
• Digennaro Angela
• Seifermann Stefan
• Joly Damien

Classifications

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title

• Y02E10/549

  Organic PV cells · CPC title