IP Library › Granted Patent US 12,312,338

Granted Patent B2

US 12,312,338 · App. 16/181,106 · Granted May 27, 2025

Organic molecules for use in optoelectronic devices

Inventors: Michael Danz (Eggenstein-Leopoldshafen, DE); Alhama Arjona Esteban (Stuttgart, DE)

C07D403/14 C07D471/04 C07D491/048 C07D495/04 C07D519/00 C09K11/06 H10K30/80 H10K50/18 H10K50/30 H10K85/654 H10K85/6572 C09K2211/1007 C09K2211/1029 C09K2211/1033 C09K2211/1037 C09K2211/1044 C09K2211/1059 H10K50/11 H10K50/15 H10K50/16

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Quick Facts

Patent No.: US 12,312,338
App. No.: 16/181,106
Granted: May 27, 2025
Kind: B2

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Abstract

The invention relates to an organic molecule for the use in optoelectronic devices. According to the invention, the organic molecule has a first chemical moiety with a structure of formula I, and two second chemical moieties with a structure of formula II, wherein # represents the binding site of a single bond linking the first chemical moiety to the second chemical moiety; V is selected from the group consisting of CN and CF 3 ; and W is the bond linking the first chemical moiety to one of the two second chemical moieties.

Claims (135)

1. An organic molecule, comprising:

a first chemical moiety comprising a structure of Formula I,

and

two second chemical moieties, each comprising a structure of Formula IIb or Formula IIc,

wherein the first chemical moiety is linked to the second chemical moiety via a single bond;

wherein # represents the binding site of the first chemical moiety to the second chemical moiety;

W is the bond linking the first chemical moiety to one of the two second chemical moieties;

V is CN;

R I is at each occurrence independently from another selected 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;

R 11 , R 12 , R 13 , R 14 and R 15 is at each occurrence independently from another selected from the group consisting of

hydrogen, deuterium, CN, CF 3 ,

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;

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

B(OR 5 ) 2 ,

C 1 -C 40 -alkyl, which is substituted with at least one selected from the group consisting of 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 -alkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkenyl, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkynyl, which is unsubstituted or substituted with one or more substituents R 6 , C 6 -C 60 -aryl, which is unsubstituted or substituted with one or more substituents R 6 , and C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with one or more substituents R 6 provided that R b is not a carbazolyl group,

C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with at least one selected 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 unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -alkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkenyl, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkynyl, which is unsubstituted or substituted with one or more substituents R 6 , C 6 -C 60 -aryl, which is unsubstituted or substituted with one or more substituents R 6 , and C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with one or more substituents R 6 ,

C 2 -C 40 -alkenyl, which is unsubstituted or substituted with at least one selected 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 unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -alkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkynyl, which is unsubstituted or substituted with one or more substituents R 6 , C 6 -C 60 -aryl, which is unsubstituted or substituted with one or more substituents R 6 , and C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with one or more substituents R 6 ,

C 2 -C 40 -alkynyl, which is unsubstituted or substituted with at least one selected 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 unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -alkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkenyl, which is unsubstituted or substituted with one or more substituents R 6 , C 6 -C 60 -aryl, which is unsubstituted or substituted with one or more substituents R 6 , and C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with one or more substituents R 6 , and

C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with at least one selected 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 unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -alkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkenyl, which is unsubstituted or substituted with one or more substituents R 6 , C 2 -C 40 -alkynyl, which is unsubstituted or substituted with one or more substituents R 6 , and C 6 -C 60 -aryl, which is unsubstituted or substituted with one or more substituents R 6 ;

R 5 is at each occurrence independently from another selected 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 unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -thioalkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 6 -C 18 -aryl, which is unsubstituted or substituted by one or more C 1 -C 5 -alkyl substituents, C 3 -C 17 -heteroaryl, which is unsubstituted or substituted by 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),

C 1 -C 40 -thioalkoxy, which is unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 40 -alkyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 6 -C 18 -aryl, which is unsubstituted or substituted by one or more C 1 -C 5 -alkyl substituents, C 3 -C 17 -heteroaryl, which is unsubstituted or substituted by 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),

C 2 -C 40 -alkenyl, which is unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 40 -alkyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -thioalkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 6 -C 18 -aryl, which is unsubstituted or substituted by one or more C 1 -C 5 -alkyl substituents, C 3 -C 17 -heteroaryl, which is unsubstituted or substituted by 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),

C 2 -C 40 -alkynyl, which is unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 40 -alkyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -thioalkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 6 -C 18 -aryl, which is unsubstituted or substituted by one or more C 1 -C 5 -alkyl substituents, C 3 -C 17 -heteroaryl, which is unsubstituted or substituted by 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),

C 6 -C 60 -aryl, which is unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 40 -alkyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -thioalkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 3 -C 17 -heteroaryl, which is unsubstituted or substituted by 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); and

C 3 -C 57 -heteroaryl, which is unsubstituted or substituted with at least one selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 40 -alkyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -alkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 1 -C 5 -thioalkoxy, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkenyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 2 -C 5 -alkynyl, which is unsubstituted or substituted by deuterium, CN, CF 3 , or F, C 6 -C 18 -aryl, which is unsubstituted or substituted by 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 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 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 the substituents R 5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R 5 .

2. The organic molecule according to claim 1 , wherein R I , R 11 , R 12 , R 13 , R 14 , R 15 is at each occurrence independently from another selected from the group consisting of H, methyl and phenyl.

3. An organic molecule, comprising:

a first chemical moiety comprising a structure of Formula I,

and

two second chemical moieties, each comprising a structure of Formula IIa′,

wherein the first chemical moiety is linked to the second chemical moiety via a single bond;

wherein

# represents the binding site of the first chemical moiety to the second chemical moiety;

W is the bond linking the first chemical moiety to one of the two second chemical moieties;

V is CN;

R I is at each occurrence independently from another selected 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;

R 11 , R 12 , R 13 , R 14 and R 15 is at each occurrence independently from another selected from the group consisting of

hydrogen, deuterium, CN, CF 3 ,

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;

R a is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , Br, I,

wherein at least one of R a is not hydrogen;

R 6 is at each occurrence independently from 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 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 the substituents R 5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R 5 provided that substituents R a do not form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R a ,

wherein the organic molecule exhibits an emission maxima in the blue or sky-blue spectral range.

4. A method for preparing an organic molecule according to claim 1 , wherein a R 11 -R 15 -substituted 2,4-dichloro-6-phenyltriazine is used as reactant.

5. A composition, comprising:

(a) at least one organic molecule according to claim 1 , 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 claim 1 , and

6. A composition, comprising:

(i) 1-50% by weight of one organic molecule according to claim 1 ;

(ii) 5-98% by weight of one host compound H;

(iii) 1-30% by weight of at least one further emitter molecule with a structure differing from the structure of the organic molecule according to claim 1 ; and

(iv) optionally, 0-94% by weight of at least one further host compound D with a structure differing from the structure of the organic molecules according to claim 1 ; and

(v) optionally, 0-94% by weight of a solvent.

7. An optoelectronic device, comprising an organic molecule according to claim 1 .

8. An optoelectronic device, comprising:

a substrate,

an anode and

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

at least one light-emitting layer, which is arranged between the anode and the cathode and which comprises an organic molecule according to claim 1 .

9. The optoelectronic device according to claim 8 , in form of a device selected from the group consisting of: organic light-emitting diodes (OLEDS), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistors, organic laser, and down-conversion element.

10. The optoelectronic device according to claim 7 , wherein the organic molecule is one or more of a luminescent emitter, a host material, an electron transport material, a hole injection material and a hole blocking material.

11. A method for producing an optoelectronic device, wherein an organic molecule according to claim 1 .

12. The method according to claim 11 , comprising depositing the organic molecule by a vacuum evaporation method or from a solution.

13. An optoelectronic device, comprising an organic molecule according to claim 5 .

14. An optoelectronic device comprising:

a substrate,

an anode and

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

at least one light-emitting layer, which is arranged between the anode and the cathode and which comprises a composition according to claim 5 .

15. A method for producing an optoelectronic device, wherein a composition according to claim 5 is deposited.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2022

From: CYNORA GMBH

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 060329/0712 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019

From: DANZ, MICHAEL, DR.; ARJONA ESTEBAN, ALHAMA

To: CYNORA GMBH

Reel/Frame 048037/0954 →

Priority Claims (2)

DE 10 2017 126 064.1 · Nov 8, 2017 · national

DE 10 2018 113 459.2 · Jun 6, 2018 · national

Continuity (1)

Related Publication 20190177303A1 · Jun 13, 2019

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