CARBAZOLE DERIVATES FOR USE IN OPTOELECTRONIC DEVICES

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

wherein

n is 1 or 2;

X is selected from the group consisting of H, SiMe 3 , SiPh 3 , CN, and CF 3 ;

Ar EWG is selected from the group consisting of Formulas IIa to IIo:

wherein # represents the binding site of the single bond shown in Formula I, which connects Ar EWG to the phenyl ring;

R 1 is selected independently of one another at each occurrence 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 2 is selected independently of one another at each occurrence 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 d is selected independently of one another at each occurrence 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 , 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 a is selected independently of one another at each occurrence from the group consisting of R A ,

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 , 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 selected independently of one another at each occurrence 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 substituted independently of one another by deuterium, CN, CF 3 , or F;

C 1 -C 5 alkoxy,

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

C 1 -C 5 thioalkoxy,

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

C 2 -C 5 alkenyl,

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

C 2 -C 5 alkynyl,

wherein one or more hydrogen atoms are optionally substituted independently of one another 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 A is selected independently of one another at each occurrence from a chemical structure of Formula IIA

or a chemical structure of Formula IIB

wherein R N is selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph;

wherein $ represents the binding site of a single bond;

wherein at least one substituent R a is R A ;

wherein R B is selected from the group consisting of

H,

Ph,

CN,

CF 3 ,

of a chemical structure of Formula IIA-2

or a chemical structure of Formula IIB-2

wherein R N# is selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph;

wherein § represents the binding site of a single bond.

2 . The organic molecule according to claim 1 , wherein, independently of one another at each occurrence, R 1 is phenyl, which is optionally substituted with one or more substituents R 6 , and

R 2 is independently of one another at each occurrence selected from the group consisting of

hydrogen,

CN,

CF 3 , and

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

3 . The organic molecule according to claim 1 , comprising a structure selected from the group consisting of Formula IIa-1, Formula IIa-2, and Formula IIa-3:

wherein R b is independently of one another at each occurrence selected from the group consisting of

H,

Me,

i Pr,

t Bu,

CN,

CF 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 .

4 . The organic molecule according to claim 1 , comprising a structure selected from the groups shown below:

5 . The organic molecule according to claim 1 , wherein R b is independently at each occurrence selected from the group consisting of H and CN.

6 . The organic molecule according to claim 1 , comprising or consisting of a structure selected from the groups shown below:

7 . The organic molecule according to claim 1 , comprising a structure selected from the group consisting of Formula IB and Formula IC:

8 .- 15 . (canceled)

16 . 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 organic molecule according to claim 1 , and

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

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

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 18 , 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 disposed between the anode and the cathode and which comprises the organic molecule.

20 . 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.

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

22 . The optoelectronic device according to claim 21 , 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.

23 . An optoelectronic device comprising the organic molecule according to claim 3 , 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.

24 . The optoelectronic device according to claim 23 , 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.

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

26 . The optoelectronic device according to claim 25 , 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.

27 . The optoelectronic device according to claim 26 , 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 disposed between the anode and the cathode and which comprises the composition.

28 . 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.