Granted Patent B2

US 12,466,994 · App. 17/296,324 · Granted Nov 11, 2025

Inventor: Sebastian Dück (Heidelberg, DE)

Assignee: Samsung Display Co., Ltd.

C09K11/06C07F5/02H10K85/322H10K85/6572H10K85/658C09K2211/1018H10K50/11

Abstract

Claims (255)

1 . An organic molecule having a structure represented by Formula I,

wherein

n is 0 or 1;

m=1−n;

X is N or CR II ;

V is N or CR XV ;

W is selected from the group consisting of a single bond, Si(R 3 ) 2 , C(R 3 ) 2 and BR 3 ;

R 1 is selected from the group consisting of:

C 1 -C 5 -alkyl,

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

C 6 -C 60 -aryl,

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

C 3 -C 57 -heteroaryl,

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

R I , R II , R III , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , and R XVI is independently from another selected from the group consisting of: hydrogen,

deuterium,

N(R 5 ) 2 ,

OR 5 ,

SR 5 ,

Si(R 5 ) 3 ,

B(OR 5 ) 2 ,

OSO 2 R 5 ,

CF 3 ,

CN,

halogen,

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 3 -C 57 -heteroaryl,

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

R IV and R V are independently from another selected from the group consisting of:

hydrogen,

deuterium,

N(R 5 ) 2 ,

OR 5 ,

SR 5 ,

Si(R 5 ) 3 ,

B(OR 5 ) 2 ,

OSO 2 R 5 ,

CF 3 ,

CN,

halogen,

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 3 -C 57 -heteroaryl,

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

RX IV is selected from the group consisting of:

hydrogen,

deuterium,

SiMe 3 ,

SiPh 3 ,

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,

and N(Ph) 2 ;

R XV is independently from another selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 3 ,

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, and

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;

R 5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 ,

C 1 -C 5 -alkyl,

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

C 1 -C 5 -alkoxy,

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

C 1 -C 5 -thioalkoxy,

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

C 2 -C 5 -alkenyl,

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

C 2 -C 5 -alkynyl,

wherein optionally one or more hydrogen atoms are 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);

R 6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 ,

C 1 -C 5 -alkyl,

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

C 1 -C 5 -alkoxy,

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

C 1 -C 5 -thioalkoxy,

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

C 2 -C 5 -alkenyl,

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

C 2 -C 5 -alkynyl,

wherein optionally one or more hydrogen atoms are 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 at least one substituent selected from the group consisting of R 1 , R I , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , and R XVI optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents from the group that is/are positioned adjacent to the at least one substituent.

2 . The organic molecule according to claim 1 , wherein R IV and R V are independently from another selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 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 ;

and

R IX and R X are independently from another selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 3 ,

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 .

3 . The organic molecule according to claim 1 , with a structure of Formula II:

4 . The organic molecule according to claim 1 , wherein X is CR II and V is CR XV .

5 . The organic molecule according to claim 1 , wherein R I , R II , R III , R VI , R VII , R VIII , R XI , R XII , R XIII , and R XVI is independently from another selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 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 ;

and

R 1 is selected from the group consisting of

C 1 -C 5 -alkyl,

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

C 6 -C 30 -aryl,

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

C 3 -C 30 -heteroaryl,

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

6 . The organic molecule according to claim 1 , wherein R II , R VI , R VIII , R XI , and R XIII is independently from another selected from the group consisting of:

hydrogen,

deuterium,

halogen,

Me,

i Pr,

t Bu,

CN,

CF 3 ,

SiMe 3 ,

SiPh 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, and

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 R I , R II , R VII , R XII , and R XVI is independently from another selected from the group consisting of:

hydrogen,

deuterium,

Me,

i Pr,

t Bu,

SiMe 3 ,

SiPh 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, 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, and N(Ph) 2 .

7 . The organic molecule according to claim 6 , wherein

R II , R VI , R VIII , R XI , and R XIII is independently from another selected from the group consisting of:

hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 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;

R XV is selected from the group consisting of:

hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 3 ; and

R I , R II , R VII , R XII , and R XVI is independently from another selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, SiMe 3 , SiPh 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, and Ph;

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

N(Ph) 2 .

8 . The organic molecule according to claim 1 , wherein R 1 is C 6 -C 30 -aryl,

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 , SiMe 3 , SiPh 3 , and Ph.

9 . A composition comprising:

(a) at least one organic molecule according to claim 1 as an emitter and/or a host;

(b) one or more emitter and/or host materials different from the 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 11 , 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 organic molecule.

13 . An optoelectronic device comprising the organic molecule according to claim 1 , wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

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

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

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

17 . The optoelectronic device according to claim 16 , 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.

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

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (49)