IP Library Granted Patent US 11,276,825
Granted Patent B2
US 11,276,825 · App. 16/322,775 · Granted Mar 15, 2022

Organic molecules for use in organic devices

Inventors: Stefan Seifermann (Bühl, DE); Michael Danz (Eggenstein-Leopoldshafen, DE); Daniel Volz (Karlsruhe, DE)
Assignee: CYNORA GmbH
H01L51/0072C07D403/04C07D403/14C07D471/04C09K11/06H01L51/0067C09K2211/1007C09K2211/1018H01L51/5012
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Quick Facts
Patent No.
US 11,276,825
App. No.
16/322,775
Granted
Mar 15, 2022
Kind
B2
Abstract

An organic molecules for use in optoelectronic devices is disclosed having a structure of formula A1: where A, R N , R a and R 2 are as defined herein.

Claims (125)

1. An organic molecule comprising a structure of Formula A1:

where

A at each instance is independently CR b or N;

R N is methyl, phenyl, xylyl, mesityl, naphthyl, biphenyl, naphthylphenyl, terphenyl or 2,4,6-triphenylphenyl;

R a at each instance is independently H, deuterium, an alkyl group or an aryl group;

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

H,

deuterium,

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group which is unsubstituted or substituted by one or more R 2 ,

an aryl group which is unsubstituted or substituted by one or more R 2 and is optionally additionally substituted by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where:

R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

R N3 is an alkyl group, an aryl group or a heteroaryl group;

R 1 at each instance is an aryl group which is unsubstituted or substituted by one or more R 2 ;

R 2 at each instance is independently F, CF 3 or CN;

where one to four A are N or at least one R b is selected from the group consisting of:

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group substituted by one or more R 2 ,

an aryl group substituted by one or more R 2 , and optionally additionally substituted by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

and where # indicates the point via which the group of the sub-formula T1 or T2 is attached via a single bond.

2. The organic molecule according to claim 1 , comprising a structure of Formula A2:

where

R c at each instance is independently selected from the group consisting of:

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group substituted by one or more R 2 ,

an aryl group substituted by one or more R 2 , and optionally additionally substituted by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

R d at each instance is independently selected from the group consisting of:

H,

deuterium,

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group which is unsubstituted or substituted by one or more R 2 ,

an aryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups, and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

and #, R a , R 1 , R 2 and R N3 have the aforestated meanings.

3. The organic molecule according to claim 1 , comprising a structure of Formula A3:

where

R c at each instance is independently selected from the group consisting of:

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group substituted by one or more R 2 ,

an aryl group substituted by one or more R 2 , and optionally additionally substituted by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

R d is the same or different at each instance and is independently selected from the group consisting of:

H,

deuterium,

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group which is unsubstituted or substituted by one or more R 2 ,

an aryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

and #, R a , R 1 , R 2 and R N3 have the aforestated meanings.

4. The organic molecule according to claim 1 , comprising a structure of Formula A4:

where

R c at each instance is independently selected from the group consisting of:

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group substituted by one or more R 2 ,

an aryl group substituted by one or more R 2 , and optionally additionally substituted by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

R d is the same or different at each instance and is independently selected from the group consisting of:

H,

deuterium,

CF 3 ,

C(═O)R 1 ,

CN,

an alkyl group which is unsubstituted or substituted by one or more R 2 ,

an aryl group which is unsubstituted or substituted by one or more R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups,

a heteroaryl group which is unsubstituted or substituted by R 2 and/or by one or more unsubstituted alkyl groups and/or by one or more unsubstituted or alkyl-substituted aryl groups and

a group of the sub-formula T1 or a group of the sub-formula T2:

where R N2 is an alkyl group, an aryl group which is unsubstituted or substituted by one or more R N3 or a heteroaryl group which is unsubstituted or substituted by one or more R N3 ;

and #, R a , R 1 , R 2 and R N3 have the aforestated meanings.

5. The organic molecule according to claim 1 , where the organic molecule has at least one CN group.

6. The organic molecule according to claim 2 , where the organic molecule has at least one CN group.

7. The organic molecule according to claim 3 , where the organic molecule has at least one CN group.

8. The organic molecule according to claim 4 , where the organic molecule has at least one CN group.

9. 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.

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

11. The optoelectronic device according to claim 10 , 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.

12. The optoelectronic device according to claim 10 , wherein the organic molecule is one of an emitter and an absorber in the optoelectronic device.

13. The optoelectronic device according to claim 12 , wherein a proportion of the organic molecule in the emitter or the absorber is in the range of 1% to 80%.

14. The optoelectronic device according to claim 10 , 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 is disposed between the anode and the cathode and which comprises the organic molecule.

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

16. The optoelectronic device according to claim 15 , wherein the organic molecule is one of an emitter and an absorber in the optoelectronic device.

17. An optoelectronic device comprising the composition according to claim 9 .

18. The optoelectronic device according to claim 17 , 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.

19. The optoelectronic device according to claim 17 , wherein the composition is one of an emitter and an absorber in the optoelectronic device.

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

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 Mar 20, 2019
From: SEIFERMANN, STEFAN; DANZ, MICHAEL; VOLZ, DANIEL
To: CYNORA GMBH
Reel/Frame 048646/0184 →
Priority Claims (1)
EP 16205427 · Dec 20, 2016 · regional
Continuity (1)
Related Publication 20210184134A1 · Jun 17, 2021