Granted Patent B2

US 12,698,297 · App. 17/997,023 · Granted Aug 4, 2026

Inventor: Sebastian Dück (Heidelberg, DE)

Assignee: Samsung Display Co., Ltd.

C07F5/027C09K11/06H10K50/11H10K85/615H10K85/636H10K85/657H10K85/658C09K2211/1018

Abstract

Claims (212)

1 . An organic molecule, comprising a structure with a plurality of units, wherein each unit comprises a structure represented by Formula IV:

Formula IV, and

wherein in Formula IV,

m is an integer from 2 to 6,

n=0 or 1;

X is at each occurrence independently selected from the group consisting of a direct bond, CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 ;

R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R V are each independently selected from the group consisting of:

hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 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 d and R e are each independently selected from the group consisting of:

hydrogen, deuterium, CF 3 , CN, F, Br, I;

C 1 -C 40 -alkyl,

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

C 2 -C 57 -heteroaryl,

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

R a is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 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 one another 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 one 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 substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -alkoxy,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -thioalkoxy,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkenyl,

wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkynyl,

wherein one or more hydrogen atoms are optionally, independently 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 , R d , R e , 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 , R d , R e , and R 5 ;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV and R V , 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 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV and R V , and

wherein the plurality of units of the organic molecule optionally link to one another via a linking group selected from the group consisting of a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, an anthracene group, a pyrene group, a pyridine group, a pyrimidine group and a triazine group;

wherein ring a, ring b, and/or ring c of at least one unit of the organic molecule is optionally shared by an adjacent unit of the organic molecule;

wherein, when ring b and ring c of one unit are shared by ring b and ring c of an adjacent unit, the direct bond between ring b and ring c in the one unit is also shared by the adjacent unit;

wherein ring a, ring b, and/or ring c of one unit is optionally fused with ring a, ring b, or ring c of an adjacent unit;

wherein any part of one unit is optionally bonded to any part of an adjacent unit such that a part of the one unit is shared with the structure of the adjacent unit; and

wherein any substituent R a , R d , R e , R IV , R V , R 2 , R 1 , R I , R II , R III , R 3 or R 4 of one unit is optionally bonded to any substituent R a , R d , R e , R IV , R V , R 2 , R 1 , R I , R II , R III , R 3 or R 4 of an adjacent unit to form a direct bond or an aryl or heteroaryl ring by fusion, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents, Ph, deuterium, halogen, CN or CF 3 .

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

3 . The organic molecule according to claim 1 , comprising a structure represented by one of the following Formulae:

and

wherein X, R 1 , R 2 , R I , R II , R III , R IV and R V , R a , R d , R e , and n are the same as respectively defined in connection with Formula IV.

4 . The organic molecule according to claim 1 , comprising a structure represented by Formula IVa-0, and/or Formula IVb-0:

wherein X, R 1 , R 2 , R I , R III , R IV , R V , R a , R d , and R e are the same as respectively defined in connection with Formula IV.

5 . The organic molecule according to claim 1 , comprising a structure represented by Formula IVb-0b:

wherein X, R 1 , R 2 , R III , R IV , R V , and R a are the same as respectively defined in connection with Formula IV.

6 . The organic molecule according to claim 1 , wherein X is NR 3 .

7 . The organic molecule according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , and R V are each independently selected from the group consisting of:

hydrogen;

deuterium;

N(R 5 ) 2 ;

OR 5 ;

Si(R 5 ) 3 ;

B(R 5 ) 2 ;

CF 3 ;

CN;

halogen;

C 1 -C 18 -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 6 -C 18 -aryl,

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

C 2 -C 17 -heteroaryl,

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

R 5 is at each occurrence independently from one another selected from the group consisting of: hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(R 6 ) 2 , CF 3 , CN, F, Br, I;

C 1 -C 18 -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 6 -C 18 -aryl,

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

C 2 -C 17 -heteroaryl,

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

wherein R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , and R V , independently from each other, are optionally bonded to an adjacent group selected from among R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , and R V to form an aryl or heteroaryl ring, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents, deuterium, halogen, CN or CF 3 .

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

hydrogen;

deuterium;

N(R 5 ) 2 ;

OR 5 ;

SR 5 ;

Si(R 5 ) 3 ;

B(OR 5 ) 2 ;

B(R 5 ) 2 ;

OSO 2 R 5 ;

CF 3 ;

CN;

halogen;

C 1 -C 18 -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 18 -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 18 -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 18 -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 18 -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 18 -aryl,

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

C 2 -C 17 -heteroaryl,

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

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

N(R 5 ) 2 ;

OR 5 ;

C 1 -C 18 -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 6 -C 18 -aryl,

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

C 2 -C 17 -heteroaryl,

wherein R V , at each occurrence independently from each other, optionally forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 2 and R IV , which is optionally substituted with one or more C 1 -C 6 -alkyl substituents, deuterium, halogen, CN or CF 3 .

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 device is 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) an 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 is 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 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 organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

16 . The organic molecule according to claim 1 , wherein m is 2.

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

wherein the device is 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.

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.

19 . 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.

Assignments (2)

Priority Claims (2)

Continuity (1)

References Cited (102)