Organic molecules for optoelectronic devices

Patent metadata

Field	Value
Publication number	US-2022285621-A1
Application number	US-202017628641-A
Country	US
Kind code	A1
Filing date	Jul 24, 2020
Priority date	Jul 25, 2019
Publication date	Sep 8, 2022
Grant date	—

Abstract

The invention relates to an organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule has a structure of formula I:whereinRI, RII, RIII and RIV is independently from another selected from the group consisting of: hydrogen, deuterium, N(R5)2, OR5, SR5, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, halogen, C1-C40-alkyl, C1-C40-alkoxy, C1-C40-thioalkoxy, C2-C40-alkenyl, C2-C40-alkynyl, C6-C60-aryl, and C3-C57-heteroaryl,andRV is selected from the group of C1-C5 alkyl, C6-C18 aryl and C3-C15 heteroaryl.

First claim

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

wherein
R I , R II , R III and R IV are independently from another selected from the group consisting of:
hydrogen,
deuterium,
N(R 5 ) 2 ,
OR 5 ,
SR 5 ,
Si(R 5 ) 3 ,
B(OR 5 ) 2 ,
OSO 2 R 5 ,
CF 3 ,
CN,
halogen,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C—C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 5 ; and

C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 5 ;

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

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

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

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

C 2 -C 5 -alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted 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 V is at each occurrence independently from another selected from the group consisting of:
a C 3 -C 15 -heteroaryl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, halogen, C 1 -C 5 -alkyl, CN, CF 3 , SiMe 3 , SiPh 3 ,
C 3 -C 15 -heteroaryl, and
C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl, CN, CF 3 and Ph;

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

C 6 -C 18 -aryl,
wherein optionally one or more hydrogen atoms are independently from each other
substituted by C 1 -C 5 -alkyl, C 6 -Cis aryl or C 3 -C 17 -heteroaryl;

C 3 -C 15 -heteroaryl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl, C 6 -Cis aryl or C 3 -C 17 -heteroaryl.

2 . The organic molecule according to claim 1 , wherein R V comprises a structure of Formula I-0:

wherein
m is 0 or 1;
n is 0 or 1;
is 0 or 1;
if n=0, then o=0;
G a is C if m=1; G a is CR a or N if m=0;
J a is C if m=1; J a is CR a or N if m=0;
Q b is C if n=1; Q b is CR 1 or N if n=0;
Q c is C if n=1; Q c is CR 2 or N if n=0;
G 2 is C if o=1; G 2 is CR b or N if o=0;
if o=1 exactly one J 2 is C and the other J 2 is N or CR b ;
if o=0 J 2 is at each occurrence independently from another selected from the group consisting of N and CR b ;
Z is Q or a direct single bond;
Q is at each occurrence independently from each other selected from the group consisting
of N and C—R 2 ;
if Z is a direct bond:
Q a is selected from a group consisting of NR c , O;
Q b and Q c are connected via a double bond and Q c and Q a are connected via a single bond;

if Z is Q:
Q a is selected from a group consisting N, O, C—R a ;
Z and Q b are connected via a double bond, while Q b and Q c are connected via a single bond and Q c and Q a are connected via a double bond;

R a is at each occurrence independently from another selected from the group consisting of the binding site or R 2
R 1 and R 2 are at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, halogen, C 1 -C 5 -alkyl, CN, CF 3 , SiMe 3 , SiPh 3 (Ph=phenyl), C 3 -C 15 -heteroaryl, and
C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl, CN, CF 3 and Ph;
R b is at each occurrence independently from another selected from the group consisting of the binding site, hydrogen, deuterium, C 1 -C 5 -alkyl, C 6 -Cis aryl or C 3 -C 17 -heteroaryl;

R c is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C 1 -C 5 -alkyl, C 6 -Cis aryl or C 3 -C 17 -heteroaryl;
exactly one of R a and R b is the binding site of R V to the structure shown in formula I; and
at least one atom of Formula I-0 is N or O.

3 . The organic molecule according to claim 1 , wherein
R I , R II , R III and R IV are independently from another selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 3 , Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, triazinyl, which is optionally substituted with

Assignees

• Cynora Gmbh

Inventors

• Thirion Damien
• Dück Sebastian
• Zink Daniel
• Resetnic Anastasia

Classifications

• C07C15/28

  Anthracenes · CPC title

• C07C251/24

  having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07C255/51

  containing at least two cyano groups bound to the carbon skeleton · CPC title