Organic molecules for optoelectronic devices

Patent metadata

Field	Value
Publication number	US-2022289769-A1
Application number	US-202017628432-A
Country	US
Kind code	A1
Filing date	Jul 24, 2020
Priority date	Jul 25, 2019
Publication date	Sep 15, 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 are 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
each of R I , R II , R III and R IV is independently selected from the group consisting of:
hydrogen,
deuterium,
N(R 5 ) 2 ,
OR 5 ,
SR 5 ,
Si(R 5 ) 3 ,
B(OR 5 ) 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 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 selected from the group consisting of: C 1 -C 5 -alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;

R VI , R VII and R VIII are at each occurrence independently 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 -C 18 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 -C 18 aryl or C 3 -C 17 -heteroaryl.

2 . The organic molecule according to claim 1 , wherein R I , R II , R III and R IV are independently from each other 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 one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .

3 . The organic molecule according to claim 1 , wherein each of R I , R II , R III and R IV is independently selected from the group consisting of:
hydrogen, deuterium, Me, i Pr, t Bu, 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, and Ph, and N(Ph) 2 .

4 . The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula Ia:

5 . The organic molecule according to claim 1 , wherein R II is equal to R III .

6 . The organic molecule according to claim 1 , wherein R V is methyl (Me), wherein one or more hydrogen atoms are optionally substituted by deuterium.

7 . The organic molecule according to claim 1 , wherein R VI , R VII and R VIII are at each occurrence independently from each other selected from the group consisting of hydrogen,
C 1 -C 5 -alkyl, 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 or C 6 -C 18 -aryl.

8 . The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula I-0:

9 . The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula Ic:

10 . (canceled)

11 . (canceled)

12 . A composition, comprising:
(a) an organic molecule according to claim 1 as an emitter and/or a host; (b) an emitter and/or a host material different from the organic molecule according to claim 1 ; and (c) optionally, a dye and/or a solvent.

13 . (canceled)

14 . (canceled)

15 . (canceled)

16 . An optoelectronic device comprising the organic molecule according to claim 1 .

17 . The optoelectronic device according to claim 16 , wherein the

Assignees

• Cynora Gmbh

Inventors

• Dück Sebastian
• Arjona Esteban Alhama
• Koch Federico

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K50/82

  Cathodes · CPC title

• H10K50/81

  Anodes · CPC title

• H10K85/322

  comprising boron · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title