Organic molecules for optoelectronic devices

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

wherein

X 1 and X 2 are at each occurrence independently selected from the group consisting of CR 21 and N;

X 3 and X 4 are at each occurrence independently selected from the group consisting of CR 22 and N;

X 5 and X 6 are at each occurrence independently selected from the group consisting of CR 23 and N;

R 11 is 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 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;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 12 is 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 2 -C 8 -alkenyl,

wherein one or ore hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 -alkynyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 13 is 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 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;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 21 is 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 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;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 22 is at each occurrence independently selected from the group consisting of hydrogen, deuterium,

C 1 -C 5 -alkyl,

wherein one or ore 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;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 23 is 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 2 -C 8 -alkenyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium;

C 2 -C 8 -alkynyl;

wherein one or ore hydrogen atoms are optionally substituted by deuterium;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R II , R III and R IV are 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 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 a is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I,

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 , O═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, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br,

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 , O═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 at each occurrence independently selected 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, independently substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -alkoxy,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 2 , or F;

C 1 -C 5 -thioalkoxy,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkenyl,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkynyl,

wherein one or more hydrogen atoms are optionally, independently 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);

wherein, optionally, the substituents R a or R 5 independently form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R a or R 5 ;

wherein

at least one variable selected from the group consisting of X 1 , X 2 is N;

at least one variable selected from the group consisting of X 3 , X 4 is N; and

at least one variable selected from the group consisting of X 5 , X 6 is N.

2. The organic molecule according to claim 1 , wherein R 11 , R 12 , R 13 , R II , R III and R IV are at each occurrence independently selected from the group consisting of H, methyl and phenyl, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and

R 21 , R 22 , R 23 are at each occurrence independently selected from the group consisting of H, methyl and phenyl, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, if only one of X 1 and X 2 is N, only one of X 3 and X 4 is N, and only one of X 5 and X 6 is N, respectively.

3. The organic molecule according to claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are N at each occurrence.

4. The organic molecule according to claim 1 , wherein

R 11 , R 12 , and R 13 are Ph at each occurrence, and

R II , R III , and R IV are H at each occurrence, and

one of R 21 is H, if only one of X 1 and X 2 is N, and

one of R 22 is H, if only one of X 3 and X 4 is N, and

one of R 23 is H, if only one of X 5 and X 6 is N.

5. The organic molecule according to claim 1 , wherein R a is at each occurrence independently selected from the group consisting of:

hydrogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 3 ,

Ph, which is optionally substituted with one or more substituents independently 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

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

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

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 selected

from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

and N(Ph) 2 .

6. The organic molecule according to claim 1 , wherein R a is at each occurrence independently selected from the group consisting of:

hydrogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 3 ,

Ph, which is optionally substituted with one or more substituents independently 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

selected from the group consisting of Me, i Pr, t Bu, CN, CF 2 , and Ph,

pyrimidinyl, which is optionally substituted with one or more substituents independently

selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and

triazinyl, which is optionally substituted with one or more substituents independently selected

from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph.

7. The organic molecule according to claim 1 , wherein R a is at each occurrence independently selected from the group consisting of hydrogen, methyl, i-propyl (OH(CH 3 ) 2 ) ( i Pr), t-butyl, phenyl, CN, CF 3 , and diphenylamine.

8. A composition comprising:

(a) at least one organic molecule according to claim 1 as an emitter and/or a host;

(b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1 ; and

(c) optionally one or more dyes and/or one or more solvents.

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

10. The optoelectronic device according to claim 9 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

11. The optoelectronic device according to claim 9 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

12. The optoelectronic device according to claim 10 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

13. An optoelectronic device comprising the organic molecule according to claim 2 .

14. The optoelectronic device according to claim 13 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

15. The optoelectronic device according to claim 14 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

16. An optoelectronic device comprising the composition according to claim 8 .

17. The optoelectronic device according to claim 16 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

18. The optoelectronic device according to claim 16 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

19. The optoelectronic device according to claim 17 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

20. A method for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.