Granted Patent B2

US 12,643,914 · App. 18/008,376 · Granted Jun 2, 2026

Inventors: Daniel Zink (Graben-Neudorf, DE); Damien Thirion (Karlsdorf-Neuthard, DE); Sebastian Dück (Heidelberg, DE); Qiang Wang (Weingarten, DE)

Assignee: Samsung Display Co., Ltd.

C07F5/027C09K11/06H10K85/658C09K2211/1018H10K50/11H10K2101/20H10K2101/90

Abstract

Claims (183)

1 . An organic molecule, comprising:

a first chemical moiety comprising a structure of Formula Ia:

and

a second chemical moiety comprising a structure of Formula Ib:

wherein in Formulae Ia and Ib,

T is a binding site of a single bond linking the first chemical moiety to the second chemical moiety or is R 2 ;

V is a binding site of a single bond linking the first chemical moiety to the second chemical moiety or is R 2 ;

W is a binding site of a single bond linking the first chemical moiety to the second chemical moiety or is R 2 ;

X is a binding site of a single bond linking the first chemical moiety to the second chemical moiety or is R 2 ;

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

R 1 is at each occurrence independently from each other selected from the group consisting of:

C 1 -C 5 -alkyl,

which is optionally substituted with one or more substituents R 5 ;

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ;

R 2 is at each occurrence independently from each other 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,

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

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

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

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 1 -C 40 -alkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 1 -C 40 -thioalkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkynyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 2 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ;

R 5 is at each occurrence independently from each other selected from the group consisting of:

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

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R 6 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 1 -C 40 -alkoxy,

which is optionally substituted with one or more substituents R 6 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 1 -C 40 -thioalkoxy,

which is optionally substituted with one or more substituents R 6 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R 6 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkynyl,

which is optionally substituted with one or more substituents R 6 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 6 ; and

C 2 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 6 ;

R 6 is at each occurrence independently from each other 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 2 -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 2 -C 17 -heteroaryl) 2 ; and

N(C 2 -C 17 -heteroaryl) (C 6 -C 18 -aryl);

wherein R a and R 5 , independently from each other, optionally form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R a and R 5 ;

wherein exactly two adjacent substituents selected from the group consisting of T, V, W and X, represent the binding sites of a single bond linking the first chemical moiety to the second chemical moiety to form a ring.

2 . The organic molecule according to claim 1 , wherein R 1 is at each occurrence independently from each other selected from the group consisting of:

methyl; and

phenyl, which is optionally substituted with one or more substituents selected from the group consisting of:

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

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and

N(Ph) 2 .

3 . The organic molecule according to claim 1 , wherein R 1 is at each occurrence phenyl, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents.

4 . The organic molecule according to claim 1 , wherein R 2 is at each occurrence independently from each other selected from the group consisting of H, deuterium, C 1 -C 5 -alkyl and phenyl.

5 . The organic molecule according to claim 1 , wherein R 2 is H at each occurrence.

6 . The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula II or Formula III:

wherein in Formulae II and III, R a , R 1 , and R 2 are each independently the same as defined in connection with Formulae Ia and Ib.

7 . The organic molecule according to claim 1 , wherein R a is at each occurrence independently from each other selected from the group consisting of:

hydrogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and

N(Ph) 2 .

8 . The organic molecule according to claim 1 , wherein the second chemical moiety comprises a structure of Formula Ib-3, a structure of Formula Ib-4, or a structure of Formula Ib-5:

wherein in Formulae Ib-3, Ib-4 and Ib-5,

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

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

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 1 -C 40 -alkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , CEC, 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 ;

C 1 -C 40 -thioalkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 2 -C 40 -alkynyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 3 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 , and

wherein R 1 is the same as defined in connection with Formulae Ia and Ib.

9 . The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula IIa or Formula IIIa:

wherein in Formulae IIa and IIIa,

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

hydrogen,

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

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and

N(Ph) 2 , and

wherein R 1 and R 2 are each independently the same as defined in connection with Formulae Ia and Ib.

10 . An optoelectronic device comprising the organic molecule according to claim 1 as a luminescent emitter.

11 . The optoelectronic device according to claim 10 , wherein the optoelectronic device comprises at least one selected from the group consisting of:

organic light-emitting diodes (OLEDs),

light-emitting electrochemical cells,

OLED-sensors,

organic diodes,

organic solar cells,

organic transistors,

organic field-effect transistors,

organic lasers, and

down-conversion elements.

12 . A composition, comprising:

(a) the organic molecule according to claim 1 , as an emitter and/or a host, and

(b) an emitter and/or a host material, which differs from the organic molecule, and

(c) optionally, a dye and/or a solvent.

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

wherein the device comprises at least one 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.

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

a substrate,

an anode, and

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

a light-emitting layer between the anode and the cathode, and comprising the organic molecule.

15 . A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 12 by a vacuum evaporation method or from a solution.

16 . A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

17 . An optoelectronic device, comprising the composition according to claim 12 ,

wherein the device comprises at least one selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

18 . The optoelectronic device according to claim 17 , comprising:

a substrate,

an anode, and

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

a light-emitting layer between the anode and the cathode, and comprising the composition.

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (16)