Granted Patent B2

US 12,486,247 · App. 17/754,652 · Granted Dec 2, 2025

Inventors: Elena Galán García (Dresden, DE); Benjamin Schulze (Dresden, DE); Domagoj Pavicic (Dresden, DE); Lidia Marin (Dresden, DE)

Assignee: Novaled GmbH

C07D401/10C07D239/74C07D241/12C07D251/22C07D413/14H10K50/165H10K85/615H10K85/654H10K85/6574

Abstract

Claims (42)

1 . Compound having the general Formula (I)

wherein

A is substituted or unsubstituted C 3 to C 14 heteroarylene comprising at least one six-membered ring, the six-membered ring comprising at least two N-atoms, wherein the one or more substituents, if present in the group A, are independently selected from the group consisting of C 1 to C 7 alkyl, C 1 to C 7 alkoxy, partially or perdeuterated C 1 to C 7 alkyl, partially or perdeuterated C 1 to C 7 alkoxy, partially or perfluorinated C 1 to C 7 alkyl, partially or perfluorinated C 1 to C 7 alkoxy, D, F and CN;

R 1 , R 2 , Q-Ar 1 and Z—Y are bound to C-atoms of A;

Q-Ar 1 and Z—Y are bound to C-atoms of the six-membered ring comprising at least two N-atoms of A;

R 1 is selected from the group consisting of H, substituted or unsubstituted C 6 to C 18 aryl, and substituted or unsubstituted C 2 to Cis heteroaryl, wherein the one or more substituents, if present in the group R 1 , are independently selected from the group consisting of C 1 to C 7 alkyl, C 1 to C 7 alkoxy, partially or perdeuterated C 1 to C 7 alkyl, partially or perdeuterated C 1 to C 7 alkoxy, partially or perfluorinated C 1 to C 7 alkyl, partially or perfluorinated C 1 to C 7 alkoxy, D, F and CN;

R 2 is selected from the group consisting of H, substituted or unsubstituted C 6 to C 18 aryl, and substituted or unsubstituted C 2 to C 18 heteroaryl, wherein the one or more substituents, if present in the group R 2 , are independently selected from the group consisting of C 1 to C 7 alkyl, C 1 to C 7 alkoxy, partially or perdeuterated C 1 to C 7 alkyl, partially or perdeuterated C 1 to C 7 alkoxy, partially or perfluorinated C 1 to C 7 alkyl, partially or perfluorinated C 1 to C 7 alkoxy, D, F and CN; or is absent in case that A is C 3 heteroarylene;

Q represents a single bond between A and Ar 1 or is a group having the Formula (II)

in Formula (II) the “*” symbols represent the positions for binding to A and Ar 1 , respectively;

X is H, C 1 to C 7 alkyl or is represented by the general formula (IV)

in formula (IV)

at least two of Ar 2 to Ar 6 are in ortho-position to each other; and/or

at least one of Ar 2 and Ar 6 is in ortho-position to the *-position; or

in case that a to e are 0 at the same time, X is in ortho-position to Ar 1 ;

Ar 1 is selected from the group consisting of CN-substituted phenyl and substituted or unsubstituted N-containing C 3 to C 20 heteroaryl, wherein the one or more substituents, if present in the group Ar 1 , are independently selected from the group consisting of C 1 to C 7 alkyl, C 1 to C 7 alkoxy, partially or perdeuterated C 1 to C 7 alkyl, partially or perdeuterated C 1 to C 7 alkoxy, partially or perfluorinated C 1 to C 7 alkyl, partially or perfluorinated C 1 to C 7 alkoxy, D, F and CN;

Ar 1 is different from A;

Z represents a single bond between A and Y or a group having the Formula (V)

in Formula (V) the “*” symbols represent the positions for binding to A and Y, respectively;

Y is H, C 1 to C 7 alkyl or is represented by the general formula (VII)

in formula (VII)

at least two of Ar 7 to Ar 11 are in ortho-position to each other; and/or

at least one of Ar 7 and Ar 11 is in ortho-position to the *-position;

X and Y cannot be H and/or C 1 to C 7 alkyl at the same time;

Q and Y may be substituted with one or more substituents selected from the group consisting of C 1 to C 7 alkyl, C 1 to C 7 alkoxy, partially or perdeuterated C 1 to C 7 alkyl, partially or perdeuterated C 1 to C 7 alkoxy, partially or perfluorinated C 1 to C 7 alkyl, partially or perfluorinated C 1 to C 7 alkoxy, D, F and CN;

a to k are independently 0 or 1, provided that 2≤a+b+c+d+e+f+g+h+i+k≤5;

Ar 2 to Ar 11 are independently selected from the group consisting of substituted or unsubstituted C 6 to C 12 aryl and C 4 to C 10 heteroaryl, wherein the one or more substituents, if present in one or more of the groups Ar 2 to Ar 11 , are independently selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 alkoxy, partially or perdeuterated C 1 to C 6 alkyl, partially or perdeuterated C 1 to C 6 alkoxy, partially or perfluorinated C 1 to C 6 alkyl, partially or perfluorinated C 1 to C 6 alkoxy, D, F and CN;

neither Formula (IV) nor Formula (VII) comprises condensed aromatic rings;

or a compound of having a structure selected from the following structures 13, 15, 16, 17, and 49 to 67

and

a compound having the following formula is excluded

2 . Compound according to claim 1 , wherein the 6-membered ring of A comprises 2 to 3 N-atoms.

3 . Compound according to claim 1 , wherein Q represents a group having the Formula (II) and/or Z represents a group having the Formula (v).

4 . Compound according to claim 1 , wherein Q represents a group having the Formula (II) and Z represents a group having the Formula (V).

5 . Compound according to claim 1 , wherein A is selected from the group consisting of triazinylene, pyrimidinylene, pyrazinylene, quinoxalinyl, quinazolinylene, and benzoquinazolinylene.

6 . Compound according to claim 1 , wherein Ar 1 is selected from the group consisting of pyridinyl, quinolinyl, isoquinolinyl, azaphenanthrenyl, carbazolyl, benzo-nitrilyl,

7 . Compound according to claim 1 , wherein the total number of aromatic rings comprised in the compound of Formula (I) is from 7 to 14.

8 . Organic semiconducting layer comprising the compound of Formula 1 according to claim 1 .

9 . Organic electronic device comprising the organic semiconducting layer according to claim 8 , wherein the organic semiconducting layer is a charge generation layer.

10 . Organic electronic device comprising the organic semiconducting layer according to claim 8 , wherein the organic semiconducting layer is an electron transport layer and the electron transport layer comprises one or more additives, wherein the additive may be an n-type dopant.

11 . Organic electronic device comprising the organic semiconducting layer according to claim 8 , wherein the organic semiconducting layer is an electron transport layer and the electron transport layer consists of a compound of Formula 1.

12 . Display device comprising the organic electronic device according to claim 9 .

13 . Lighting device comprising the organic electronic device according to claim 9 .

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (60)