Organic molecules for use in optoelectronic devices

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

with

X=CN or CF3, and

D=

wherein

# is the point of attachment of unit D to one of the phenyl rings shown in Formula I;

Z is a direct bond or is selected from the group consisting of CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 ;

in each occurrence R 1 and R 2 are the same or different and are selected from the group consisting of:

H, deuterium;

a linear alkyl group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium;

a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein one or more H atoms can be replaced by deuterium;

a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium; and

an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;

in each occurrence R a , R 3 and R 4 are the same or different and are selected from the group consisting of:

H, deuterium, N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I,

a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case can be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;

an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 5 ; and

a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 5 ;

in each occurrence R 5 is the same or different and is selected from the group consisting of:

H, deuterium, N(R 6 ) 2 , OH, Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I,

a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;

an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 6 ; and

a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 6 ;

in each occurrence R 6 is the same or different and is selected from the group consisting of:

H, deuterium, OH, CF 3 , CN, F, Br, I,

a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms;

an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and

a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;

wherein each of the radicals R a , R 3 , R 4 or R 5 can also form a mono- or polycyclic, aliphatic, aromatic and/or benzoannelated ring system with one or more further radicals R a , R 3 , R 4 or R 5 ; and

wherein at least one R a is not H, and

wherein at least one R 2 is H.

2. The organic molecule according to claim 1 , wherein R 1 is H or methyl and R 2 is H.

3. The organic molecule according to claim 1 , wherein both X are CN.

4. The organic molecule according to claim 1 , wherein D comprises a structure of Formula IIa:

wherein # and R a have the aforestated meanings.

5. The organic molecule according to claim 1 , wherein D comprises a structure of Formula

wherein

in each occurrence R b is the same or different and is selected from the group consisting of:

N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I;

a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;

an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 5 ; and

a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 5 ;

and # and R 5 have the aforestated meanings.

6. The organic molecule according to claim 1 , wherein D comprises a structure of Formula IIc:

wherein

in each occurrence R b is the same or different and is selected from the group consisting of:

N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I;

a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R5)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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;

an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;

an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 5 ; and

a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 5 ;

and # and R 5 have the aforestated meanings.

7. The organic molecule according to claim 5 , wherein in each occurrence R b is the same or different and is selected from the group consisting of:

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

Ph, which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

pyridinyl, which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

carbazolyl which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph; and

N(Ph) 2 .

8. A method for producing an organic molecule according to claim 1 , wherein a in 6 position R 1 -substituted and in 3 and 5 position R 2 -substituted 2-bromo-4-fluorobenzonitrile or a in 6 position R 1 -substituted and in 3 and 5 position R 2 -substituted 2-bromo-4-fluorobenzotrifluoride is used as the educt.

9. An optoelectronic device comprising an 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. 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.

12. An optoelectronic device comprising the composition according to claim 11 .

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

a substrate;

an anode; and

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.

14. The optoelectronic device according to claim 9 , wherein the organic molecule is one of an emitter and a host in the optoelectronic component.

15. The optoelectronic device according to claim 10 , wherein the organic molecule is one of an emitter and a host in the optoelectronic component.

16. The optoelectronic device according to claim 14 , wherein the proportion of the organic molecule in the emitter or the host is in the range of 1% to 80%.

17. 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.

18. The organic molecule according to claim 2 , wherein both X are CN.

19. The organic molecule according to claim 6 , wherein in each occurrence R b is the same or different and is selected from the group consisting of:

wherein in each occurrence R b is the same or different and is selected from the group consisting of:

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

Ph, which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

pyridinyl, which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph;

carbazolyl which can in each case be substituted with one or more radicals selected from Me, i Pr, t Bu, CN, CF 3 , or Ph; and

N(Ph) 2 .

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