Organic molecules for optoelectronic devices

1 . An organic molecule, comprising a structure represented by Formula IIIe-0:

Formula IIIe-0, and

wherein in Formula IIIe-0,

Q 1 is selected from the group consisting of C and CR III ;

Q 2 is selected from the group consisting of C and CR II ;

Q 3 is selected from the group consisting of C and CR I ;

Q 4 is selected from the group consisting of C and CR 1 ;

wherein

at least one substituent selected from the group consisting of Q 2 and Q 3 is C; and

when only one substituent selected from the group consisting of Q 2 and Q 3 is C, exactly one substituent selected from the group consisting of Q 1 and Q 4 is C;

R 1 , R 2 , R 3 , R I , R II , R III , R IV and R V are each 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 , B(R 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 2 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ;

R a is at each occurrence 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 , B (R 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 2 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ;

R 5 is at each occurrence independently from one another selected from the group consisting of:

hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 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 2 -C 57 -heteroaryl,

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

R 6 is at each occurrence independently from one 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 2 -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 2 -C 17 -heteroaryl) 2 ; and

N(C 2 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

wherein any of the substituents R a and R 5 optionally form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R a and R 5 ; and

wherein any of the substituents R 1 , R 2 , R 3 , R 5 , R I , R II , R III , R IV , and R V optionally form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents R 1 , R 2 , R 3 , R 5 , R I , R II , R III , R IV and/or R V .

2 . The organic molecule according to claim 1 , wherein R 1 , R 2 , R 3 , R 5 , R I , R II , R III , R IV , and R V are each independently selected from the group consisting of:

hydrogen;

deuterium;

N(R 5 ) 2 ;

OR 5 ;

Si(R 5 ) 3 ;

B(R 5 ) 2 ;

CF 3 ;

CN;

halogen;

C 1 -C 18 -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 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ; and

R 5 is independently selected from the group consisting of:

hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(R 6 ) 2 , CF 3 , CN, F, Br, I;

C 1 -C 18 -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 6 -C 18 -aryl,

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

C 2 -C 17 -heteroaryl,

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

wherein any of the substituents R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , and R V are optionally bonded to each other and form an aryl or heteroaryl ring, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents, deuterium, halogen, CN or CF 3 .

3 . Organic molecule according to claim 1 , comprising a structure of Formula IIIe:

and

wherein R 1 , R 2 , R 3 , R 5 , R a , R III , R IV and R V are the same as respective defined in connection with Formula IIIe-0.

4 . The organic molecule according to claim 1 , wherein R 1 is not hydrogen and R 1 is not deuterium.

5 . The organic molecule according to claim 1 , wherein R a is at each occurrence 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 , B (R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, halogen;

C 1 -C 18 -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 18 -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 18 -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 18 -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 18 -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 18 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 5 .

6 . The organic molecule according to claim 1 , wherein R V is N(R 5 ) 2 and/or forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with R 2 , R 3 , R 5 , and/or R IV .

7 . The organic molecule according to claim 1 , wherein at least one substituent selected from the group consisting of R 1 , R 2 , R III , R IV , and R V forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 1 , R 2 , R 3 , R 5 , R I , R II , R III , R IV , and R V .

8 . The organic molecule according to claim 1 , wherein R 3 is at each occurrence independently selected from the group consisting of:

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 5 .

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

hydrogen;

deuterium;

C 1 -C 18 -alkyl,

which is optionally substituted with one or more substituents R 5 ;

C 6 -C 18 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 17 -heteroaryl,

which is optionally substituted with one or more substituents R 5 .

10 . An optoelectronic device comprising the organic molecule according to claim 1 as a luminescent emitter.

11 . The optoelectronic device according to claim 10 , wherein the optoelectronic device is selected from the group consisting of:

organic light-emitting diodes (OLEDs),

light-emitting electrochemical cells,

OLED-sensors,

organic diodes,

organic solar cells,

organic transistors,

organic field-effect transistors,

organic lasers, and

down-conversion elements.

12 . A composition, comprising:

(a) the organic molecule according to claim 1 , as an emitter and/or a host, and

(b) an emitter and/or a host material, which differs from the organic molecule, and

(c) optionally, a dye and/or a solvent.

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

wherein the device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.

14 . The optoelectronic device according to claim 13 , comprising:

a substrate,

an anode, and

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

a light-emitting layer between the anode and the cathode, and comprising the organic molecule.

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

16 . An optoelectronic device, comprising the composition according to claim 12 ,

wherein the device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.

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

a substrate,

an anode, and

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

a light-emitting layer between the anode and the cathode, and comprising the composition.

18 . A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 17 by a vacuum evaporation method or from a solution.