Benzo[b][1,4]benzazaborinine for optoelectronic devices

Patent metadata

Field	Value
Publication number	US-2023422614-A1
Application number	US-202118022732-A
Country	US
Kind code	A1
Filing date	Aug 23, 2021
Priority date	Aug 24, 2020
Publication date	Dec 28, 2023
Grant date	—

Abstract

The invention relates to an organic molecule for use in optoelectronic devices. The organic molecule has a structure of Formula I:

wherein
X and Y are independently selected from the group consisting of a direct bond, N—R 3 ,
O, S, Si(R 3 ) 2 and C(R 3 ) 2 ;
Z is a direct bond;
m is 0 or 1;
n is 0 or 1;
is 0 or 1;
R 1 is independently selected from the group consisting of: hydrogen, deuterium, N(R 3 ) 2 , OR 3 , SR 3 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , CF 3 , CN, halogen, C 1 -C 40 -alkyl, C 1 -C 40 -alkoxy, C 1 -C 40 -thioalkoxy, C 2 -C 40 -alkenyl, C 2 -C 40 -alkynyl, C 6 -C 60 -aryl; and
R a and R 2 are independently selected from the group consisting of: hydrogen, deuterium, N(R 3 ) 2 , OR 3 , SR 3 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , CF 3 , CN, halogen, C 1 -C 40 alkyl, C 1 -C 40 -alkoxy, C 1 -C 40 -thioalkoxy, C 2 -C 40 -alkenyl, C 2 -C 40 -alkynyl, C 6 -C 60 -aryl; and C 3 -C 57 -heteroaryl.

First claim

1 - 15 . (canceled)

16 . An organic molecule represented by Formula I:

wherein in Formula I,
X and Y are independently from each other selected from the group consisting of a direct bond, N—R 3 , O, S, Si(R 3 ) 2 and C(R 3 ) 2 ;
Z is a direct bond;
m is 0 or 1;
n is 0 or 1;
o is 0 or 1;
R 1 is at each occurrence independently selected from the group consisting of:
hydrogen;
deuterium;
N(R 3 ) 2 ;
OR 3 ;
SR 3 ;
Si(R 3 ) 3 ;
B(OR 3 ) 2 ;
OSO 2 R 3 ;
CF 3 ;
CN;
halogen;
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ; and
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 3 ;
R a and R 2 are at each occurrence independently selected from the group consisting of:
hydrogen;
deuterium;
N(R 3 ) 2 ;
OR 3 ;
SR 3 ;
Si(R 3 ) 3 ;
B(OR 3 ) 2 ;
OSO 2 R 3 ;
CF 3 ;
CN;
halogen;
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 3 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 3 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 3 ;
R 3 is at each occurrence independently selected from the group consisting of:
hydrogen;
deuterium;
N(R 4 ) 2 ;
OR 4 ;
SR 4 ;
Si(R 4 ) 3 ;
B(OR 4 ) 2 ;
OSO 2 R 4 ;
CF 3 ;
CN;
halogen;
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 4 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 4 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 4 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 4 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 4 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 4 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 4 ;
R 4 is at each occurrence independently selected from the group consisting of:
hydrogen; deuterium; halogen; OPh; SPh; CF 3 ; CN; Si(C 1 -C 5 -alkyl) 3 ; Si(Ph) 3 ;
C 1 -C 5 -alkyl,
wherein optionally one or more hydrogen atoms are independently substituted by deuterium, halogen, CN, or CF 3 ;
C 1 -C 5 -alkoxy,
wherein optionally one or more hydrogen atoms are independently substituted by deuterium, halogen, CN, or CF 3 ;
C 1 -C 5 -thioalkoxy,
wherein optionally one or more hydrogen atoms are independently substituted by deuterium, halogen, CN, or CF 3 ;
C 2 -C 5 -alkenyl,
wherein optionally one or more hydrogen atoms are independently substituted by deuterium, halogen, CN, or CF 3 ;
C 2 -C 5 -alkynyl,
wherein optionally one or more hydrogen atoms are independently substituted by deuterium, halogen, CN, or CF 3 ;
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

Assignees

• Samsung Display Co Ltd

Inventors

• Seifermann Stefan
• Danz Michael
• Dück Sebastian

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F5/027

  Organoboranes and organoborohydrides · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title