Organic molecules for optoelectronic devices

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

wherein

R I , R II , R III is independently from another selected from the group consisting of

hydrogen (H),

deuterium,

CF 3 ,

CN,

halogen,

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R 1 ,

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R 1 ,

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 1 ;

R 1 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, CF 3 , CN, F,

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 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 6 -C 18 -aryl,

which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;

R IV , R V , R VI , R VII , R VIII , R IX , R X is at each occurrence independently from another 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 , 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,

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 , 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 from another 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 from each other substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -alkoxy,

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

C 1 -C 5 -thioalkoxy,

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

C 2 -C 5 -alkenyl,

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

C 2 -C 5 -alkynyl,

wherein one or more hydrogen atoms are optionally, 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);

wherein the substituents R IV , R V , R VI , R VII , R VIII , R IX , R X or R 5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R IV , R V , R VI , R VII , R VIII , R IX , R X or R 5 ;

R XI , R XII , R XII is independently from another selected from the group consisting of hydrogen and R A ;

R A is independently from another selected from the group consisting of

C 1 -C 5 -alkyl,

which is optionally substituted with one or more substituents R 2 ,

phenyl,

which is optionally substituted with one or more substituents R 2 ;

R 2 is at each occurrence independently from another selected from the group consisting of C 1 -C 5 -alkyl and phenyl;

wherein one or two substituents selected from the group consisting of R XI , R XII and R XIII is R A .

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

wherein R VI and R IX is at each occurrence independently from another 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 , 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,

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 , 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 from another 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 from each other substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -alkoxy,

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

C 1 -C 5 -thioalkoxy,

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

C 2 -C 5 -alkenyl,

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

C 2 -C 5 -alkynyl,

wherein one or more hydrogen atoms are optionally, 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).

3. The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of formula Ib:

wherein

R VI and R IX are at each occurrence independently from another selected from the group consisting of

H, Me, i Pr, t Bu, CN, CF 3 ,

phenyl,

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 .

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

wherein

R VI and R IX are at each occurrence independently from another selected from the group consisting of

H, Me, i Pr, t Bu, CN, CF 3 ,

phenyl,

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 ,

R I , R II , R III are independently from another selected from the group consisting of

hydrogen,

Me,

i Pr,

t Bu,

and C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents selected from the group consisting of Me, i Pr, t Bu and phenyl.

5. The organic molecule according to claim 1 , wherein R IV , R V , R VI , R VII , R VIII , R IX , R X are at each occurrence independently from another selected from the group consisting of

hydrogen, Me, i Pr, t Bu, CN, CF 3 ,

phenyl,

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 ,

and further wherein

R I , R II , R III are independently from another selected from the group consisting of

hydrogen,

Me,

i Pr,

t Bu,

and C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents selected from the group consisting of Me, i Pr, t Bu and phenyl.

6. The organic molecule according to claim 1 , wherein R I , R II , R III are independently from another selected from the group consisting of

hydrogen,

Me,

i Pr,

t Bu,

and C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents selected from the group consisting of Me, i Pr, t Bu and phenyl.

7. The organic molecule according to claim 1 , wherein R A is at each occurrence independently from another selected from the group consisting of phenyl, biphenyl and tert-butyl.

8. A composition comprising:

(a) at least one organic molecule according to claim 1 as an emitter and/or 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 disposed on the substrate; and

at least one light-emitting layer arranged 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 disposed on the substrate; and

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

13. An optoelectronic device comprising the organic molecule according to claim 1 , wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

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

15. The optoelectronic device according to claim 14 , 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.

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

a substrate;

an anode;

a cathode, wherein the anode or the cathode is disposed on the substrate; and

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

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

18. The optoelectronic device according to claim 17 , 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.

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

a substrate;

an anode;

a cathode, wherein the anode or the cathode is disposed on the substrate; and

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

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.