Organic molecules for use in optoelectronic devices

1. An organic molecule having a structure of Formula I:

wherein

x is n or cr x ;

V is N or CR V ;

Z is N or CR II ;

provided that at least one of X, V, or Z is N;

W is selected from the group consisting of Si(R 3 ) 2 , C(R 3 ) 2 , and BR 3 ;

R 1 , R 2 and R 3 is independently from each other selected from the group consisting of:

C 1 -C 5 -alkyl,

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

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 I , R II , R III , R IV , R V , R vI , R IX , R X , and R XI are independently from each other 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,

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 each other selected from the group consisting of: hydrogen, deuterium, OPh, 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 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 5 -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 6 is at each occurrence independently from each other selected from the group consisting of hydrogen, deuterium, OPh, 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 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);

wherein at least one substituent selected from the group consisting of R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents of the same group that is/are positioned adjacent to the at least one substituent.

2. The organic molecule according to claim 1 , wherein R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI are independently selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 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, ′ Pr, tBu, CN, CF 3 , and Ph,

and N(Ph) 2 ;

R 1 and R 2 each independently from each other is selected from the group consisting of

C 1 -C 5 -alkyl,

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

C 6 -C 30 -aryl,

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

C 3 -C 30 -heteroaryl,

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

3. The organic molecule according to claim 2 , wherein R I , R III , R IV , R VI , and R XI are independently selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 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, and

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 R II , R V , and R X are independently selected from the group consisting of:

hydrogen,

deuterium,

Me,

i Pr,

t Bu,

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,

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,

and N(Ph) 2 .

4. The organic molecule according to claim 3 , wherein

R I , R III , R IV , R VI , R IX , and R XI are independently selected from the group consisting of: hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , and

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;

and R II , and R V , and R X are independently selected from the group consisting of hydrogen, deuterium, Me, i Pr, tBu,

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;

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, t Bu, and Ph;

and N(Ph) 2 .

5. The organic molecule according to claim 1 , wherein R 1 and R 2 independently from each other are C 6 -C 30 -aryl,

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.

6. The organic molecule according to claim 5 , wherein R 1 and R 2 are each independently phenyl or mesityl.

7. 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, and

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

8. An optoelectronic device comprising the composition according to claim 7 , 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.

9. The optoelectronic device according to claim 8 , 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.

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

12. An optoelectronic device comprising the organic molecule according to claim 1 , wherein the organic molecule is at least one selected from the group consisting of a luminescent emitter, an electron transport material, a hole injection material, and a hole blocking material in the optoelectronic device.

13. The optoelectronic device according to claim 12 , 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.

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