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1. (WO2019001838) ORGANIC MOLECULES, IN PARTICULAR FOR USE IN OPTOELECTRONIC DEVICES
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Claims

1 . Organic molecule, comprising

- a first chemical moiety comprising a structure of Formula I,


Formula I

and

- two second chemical moieties, each independently from another comprising a structure of Formula II,


Formula II

wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;

wherein

T is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen;

V is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen;

W is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF3;

X is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF3;

Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF3;

# represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;

Z is at each occurrence independently from another selected from the group consisting of a direct bond, CR3R4, C=CR3R4, C=0, C=NR3, NR3, O, SiR3R4, S, S(O) and S(0)2;

R1 ,R2 is independently form each other at each occurrence independently from another selected from the group consisting of

hydrogen,

deuterium,

d-Cs-alkyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium;

C2-C8-alkenyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium;

C2-C8-alkynyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium; and

which is optionally substituted with one or more substituents R6; and

Ra, R3 and R4 is at each occurrence independently from another selected from the group consisting of hydrogen,

deuterium,

N(R5)2,

OR5,

Si(R5)3,

B(OR5)2,

CF3,

CN,

F,

Br,

I,

Ci-C4o-alkyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-alkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-thioalkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkenyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkynyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ce-Ceo-aryl,

which is optionally substituted with one or more substituents R5; and

C3-C57-heteroaryl,

which is optionally substituted with one or more substituents R5;

R5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OS02R6, CF3, CN, F, Br, I,

Ci-C4o-alkyl,

which is optionally substituted with one or more substituents R6 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;

Ci-C4o-alkoxy,

which is optionally substituted with one or more substituents R6 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;

Ci-C4o-thioalkoxy,

which is optionally substituted with one or more substituents R6 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;

C2-C4o-alkenyl,

which is optionally substituted with one or more substituents R6 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;

C2-C4o-alkynyl,

which is optionally substituted with one or more substituents R6 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;

Ce-Ceo-aryl,

which is optionally substituted with one or more substituents R6; and

C3-C57-heteroaryl,

which is optionally substituted with one or more substituents R6;

R6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF3, CN, F,

d-Cs-alkyl,

wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;

Ci-C5-alkoxy,

wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;

Ci-C5-thioalkoxy,

wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkenyl,

wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkynyl,

wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;

which is optionally substituted with one or more d-Cs-alkyl substituents;

C3-Ci7-heteroaryl,

which is optionally substituted with one or more d-Cs-alkyl substituents;


N(C3-Ci7-heteroaryl)2,

and N(C3-Ci7-heteroaryl)(C6-Ci8-aryl);

wherein the substituents Ra, R3, R4 or R5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Ra, R3, R4 or R5;

wherein exactly one substituent selected from the group consisting of W, X, and Y is CN or CF3, and exactly two substituents selected from the group consisting of T, V, W, X and Y represent the binding sites of a single bond linking the first chemical moiety and one of the two second chemical moieties.

2. The organic molecule according to claim 1 , wherein R1 and R2 is independently from each other at each occurrence independently from another selected from the group consisting of H, methyl and phenyl.

3. The organic molecule according to claim 1 or 2, wherein W is CN.

4. The organic molecule according to one or more of claims 1 to 3, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of Formula lla:


Formula lla

wherein # and Ra are defined as in claim 1.

5. The organic molecule according to one or more of claims 1 to 4, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of Formula lib:


Formula lib

wherein

Rb is at each occurrence independently from another selected from the group consisting of deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OS02R5, CF3, CN, F, Br, I,

Ci-C4o-alkyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-alkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-thioalkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkenyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkynyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ce-Ceo-aryl,

which is optionally substituted with one or more substituents R5; and

C3-C57-heteroaryl,

which is optionally substituted with one or more substituents R5;

and wherein apart from that the definitions in claim 1 apply.

6. The organic molecule according to one or more of claims 1 to 4, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of formula lie:


Formula lie

wherein

Rb is at each occurrence independently from another selected from the group consisting of deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OS02R5, CF3, CN, F, Br, I,

Ci-C4o-alkyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-alkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ci-C4o-thioalkoxy,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkenyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

C2-C4o-alkynyl,

which is optionally substituted with one or more substituents R5 and

wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;

Ce-Ceo-aryl,

which is optionally substituted with one or more substituents R5; and

C3-C57-heteroaryl,

which is optionally substituted with one or more substituents R5;

and wherein apart from that the definitions in claim 1 apply.

7. The organic molecule according to claim 5 or 6, wherein Rb is at each occurrence independently from another selected from the group consisting of

Me, jPr, 'Bu, CN, CF3,

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, 'Bu, CN, CF3 and Ph;

pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, 'Bu, CN, CF3 and Ph;

pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, 'Bu, CN, CF3 and Ph;

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, 'Bu, CN, CF3 and Ph;

triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, 'Bu, CN, CF3, and Ph;

and

N(Ph)2.

8. A process for preparing organic molecules according to claims 1 to 7, wherein a 2,4-R1-6-R2-substituted 3-bromo/chloro-5-cyanobenzotrifluoride is used as a reactant, which preferably reacts with a difluoro-substituted, cyano/(trifluoromethyl)-phenylboronic acid ester or a difluoro-substituted, cyano/(trifluoromethyl)-phenylboronic acid.

9. Use of a molecule according to one or more of claims 1 to 7 as luminescent emitter and/or host material and or electron transport material and/or hole injection material and/or hole blocking material in an organic optoelectronic device.

10. The use according to claim 9, wherein the organic optoelectronic device is selected from the group consisting of:

• organic light-emitting diodes (OLEDS),

• light-emitting electrochemical cells,

• OLED-sensors, in particular in non-hermetically shielded gas and vapor sensors,

• organic diodes,

• organic solar cells,

• organic transistors,

• organic field-effect transistors,

• organic lasers and

• down-conversion elements.

1 1 . A composition comprising:

(a) at least one organic molecule according to one or more of claims 1 to 7, in particular in the form of an emitter and/or a host, and

(b) one or more emitter and/or host materials, which differ from the organic molecule of one or more of claims 1 to 7 and

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

12. An organic optoelectronic device, comprising one organic molecule according to one or more of claims 1 to 7 or a composition according to claim 1 1 , in particular in form of a device 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.

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

- a substrate,

- an anode and

- a cathode, wherein the anode or the cathode are disposed on the substrate and

- at least a light-emitting layer, which is arranged between anode and cathode and which comprises the organic molecule according to claims 1 to 7 or a composition according to claim 1 1.

14. A process for producing an optoelectronic device, wherein an organic molecule according to one of claims 1 to 7 or a composition according to claim 1 1 is used, in particular comprising the processing of the organic compound by vacuum evaporation method or from a solution.