IP Library › Granted Patent US 12,735,638

Granted Patent B2

US 12,735,638 · App. 18/418,076 · Granted Sep 15, 2026

Organic molecules in particular for use in optoelectronic devices

Inventors: Stefan Seifermann (Buehl, DE); Harald Fluegge (Karlsruhe, DE); Sandra Bonus (Cologne, DE)

Assignee: Samsung Display Co., Ltd.

C09K11/06 C07F5/027 H10K85/654 H10K85/6572 H10K85/658 C09K2211/1007 C09K2211/1018 H10K50/11 H10K2101/20 H10K2101/30

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Quick Facts

Patent No.: US 12,735,638
App. No.: 18/418,076
Granted: Sep 15, 2026
Kind: B2

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Abstract

The invention relates to an organic molecule, comprising or consisting of Formula A: wherein M TADF represents a TADF moiety, M NRCT represents a near-range charge transfer (NRCT) emitter moiety, and L represents a divalent bridging unit that links M TADF and M NRCT and is linked to M TADF and to M NRCT via a single bond each. Furthermore, the present invention relates to the use of such organic molecule as a luminescent emitter in an optoelectronic device.

Claims (485)

1 . An organic molecule represented by Formula A:

wherein

L represents a divalent bridging unit that links M TADF and M NRCT and is linked to M TADF and to M NRCT via a single bond each, and

wherein M TADF consists of

a first chemical moiety consisting of a structure according to Formula I,

and

one second chemical moiety consisting of a structure according to Formula II,

wherein the first chemical moiety is linked to the second chemical moiety via a single bond;

T is selected from the group consisting of:

hydrogen (H), deuterium (D), R TADF1 , and the binding site of a single bond linking the first chemical moiety to the second chemical moiety,

W is selected from the group consisting of:

the binding site of a single bond linking the first chemical moiety to the second chemical moiety,

the binding site of a single bond linking the TADF moiety M TADF to the bridging unit L, H, D, and R TADF1 :

Y is selected from the group consisting of H, D, R TADF1 , and the binding site of a single bond linking the TADF moiety M TADF to the bridging unit L;

Acc 1 is selected from the group consisting of:

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

CN,

CF 3 ,

Ph, which is optionally substituted with one or more substituents selected from the group consisting of CN, CF 3 and F;

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

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

# represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety;

R Di is selected from the group consisting of the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L, H, D, Me, i Pr, t Bu, SiPh 3 , 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, and Ph, and

a third chemical moiety consisting of a structure of Formula Q:

wherein Q 1 is selected from the group consisting of N and C—R QI ;

Q 2 is selected from the group consisting of N and C—R QIII ;

Q 3 is selected from the group consisting of N and C—R QIV ;

Q 4 is selected from the group consisting of N and C—R QV ; and

$ Q represents the binding site of a single bond linking the third chemical moiety to the first chemical moiety;

R QI is selected from the group consisting of:

CN,

CF 3 ,

SiPh 3 ,

Ph, and

a fourth chemical moiety comprising or consisting of a structure of Formula IIQ:

§ Q represents the binding site of a single bond linking the fourth chemical moiety to the third chemical moiety;

R QII is selected from the group consisting of:

the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L, H, D, Me, i Pr, t Bu, SiPh 3 , and

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;

R QIII is selected from the group consisting of

the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L,

CN,

CF 3 ,

SiPh 3 ,

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

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

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

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

R QIV is selected from the group consisting of:

the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L,

CN,

CF 3 ,

SiPh 3 ,

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

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

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

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

R QV is selected from the group consisting of:

the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L, H, D, Me, i Pr, t Bu, SiPh 3 , and

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;

wherein in case one R Di represents the third chemical moiety comprising or consisting of a structure of Formula Q,

the other R Di is selected from the group consisting of H, D, Me, i Pr, t Bu, 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, and

the binding site of the single bond linking the TADF moiety M TADF to the bridging unit L;

R TADF1 is selected from the group consisting of:

Me, i Pr, t Bu, SiPh 3 , and

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;

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

N(R 5 ) 2 ,

OR 5 ,

Si(R 5 ) 3 ,

B(OR 5 ) 2

OSO 2 R 5

CF 3 ,

CN,

Br,

C 1 -C 40 -alkyl,

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

wherein one CH 2 -group or more than one 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

C 1 -C 40 -thioalkoxy,

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

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

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 5 is at each occurrence independently from another selected from the group consisting

of H,

N(R 6 ) 2 ,

OR 6 ,

Si(R 6 ) 3 ,

B(OR 6 ) 2 ,

OSO 2 R 6 ,

CF 3 ,

CN,

Br,

C 1 -C 40 -alkyl,

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

wherein one CH 2 -group or more than one 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

C 1 -C 40 -thioalkoxy,

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

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

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 6 is at each occurrence independently from another selected from the group consisting of

C 6 -C 18 -aryl, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;

hydrogen,

deuterium,

OPh,

CF 3 ,

CN,

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 3 -C 17 -heteroaryl, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;

N(C 6 -C 18 -aryl)(C 6 -C 18 -aryl);

N(C 3 -C 17 -heteroaryl)(C 3 -C 17 -heteroaryl); and

N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

wherein two or more of the substituents R a and/or R 5 independently from each other optionally form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with one or more substituents R a or R 5 ;

R f is at each occurrence independently from another selected from the group consisting

of H,

N(R 5f ) 2 ,

OR 5f ,

Si(R 5f ) 3 ,

B(OR 5f ) 2 ,

OSO 2 R 5f ,

CF 3 ,

CN,

C 1 -C 40 -alkyl,

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

wherein one CH 2 -group or more than one non-adjacent CH 2 -groups are optionally substituted by R 5f C═CR 5f , C≡C, Si(R 5f ) 2 , Ge(R 5f ) 2 , Sn(R 5f ) 2 , C═O, C═S, C═Se, C═NR 5f , P(═O)(R 5f ), SO, SO 2 , NR 5f , O, S or CONR 5f ,

C 1 -C 40 -alkoxy,

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

C 1 -C 40 -thioalkoxy,

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

wherein one CH 2 -group or more than one non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5f , C≡C, Si(R 5f ) 2 , Ge(R 5f ) 2 , Sn(R 5f ) 2 , C═O, C═S, C═Se, C═NR 5f , P(═O)(R 5f ), SO, SO 2 , NR 5f , O, S or CONR 5f ,

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

C 6 -C 60 -aryl,

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

C 3 -C 57 -heteroaryl,

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

R 5f is at each occurrence independently from another selected from the group consisting of H,

N(R 6f ) 2 ,

OR 6f ,

Si(R 6f ) 3 ,

B(OR 6f ) 2 ,

OSO 2 R 6f ,

CF 3 ,

CN,

C 1 -C 40 -alkyl,

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

wherein one CH 2 -group or more than one non-adjacent CH 2 -groups are optionally substituted by R 6f C═CR 6f , C≡C, Si(R 6f ) 2 , Ge(R 6f ) 2 , Sn(R 6f ) 2 , C═O, C═S, C═Se, C═NR 6f , P(═O)(R 6f ), SO, SO 2 , NR 6f , O, S or CONR 6f ,

C 1 -C 40 -alkoxy,

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

C 1 -C 40 -thioalkoxy,

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

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

C 6 -C 60 -aryl,

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

C 3 -C 57 -heteroaryl,

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

R 6f is at each occurrence independently from another selected from the group consisting of H,

OPh,

CF 3 ,

CN,

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)(C 6 -C 18 -aryl);

N(C 3 -C 17 -heteroaryl)(C 3 -C 17 -heteroaryl); and

N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

wherein two or more of the substituents R f and/or R 5f independently from each other optionally form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with one or more substituents R f or R 5f ,

wherein M TADF contains exactly one binding site of the single bond linking the TADF moiety M TADF to the bridging unit L and

wherein one selected from the group consisting of T, W, and Y represents the binding site of a single bond linking the first chemical moiety and the second chemical moiety, and

wherein M NRCT consists of a structure according to Formula NRCT I:

wherein

n is 0 or 1;

m=1-n;

X 1 is N or B;

X 2 is N or B;

X 3 is N or B;

W, if present, is selected from the group consisting of Si(R NRCT3 ) 2 , C(R NRCT3 ) 2 and BR NRCT3 ;

each of R 1 , R 2 and R NRCT3 is independently from each other selected from the group consisting of:

C 6 -C 60 -aryl, which is optionally substituted with one or more substituents R NRCT6 ; and

C 1 -C 5 -alkyl, which is optionally substituted with one or more substituents R NRCT6 ; and

C 3 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R NRCT6 ;

wherein at least one of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is a binding site of a single bond linking the NRCT emitter moiety M NRCT to the bridging unit L;

the further residues R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI and, as far as present, R VII and R VIII , are each independently from another selected from the group consisting of:

hydrogen,

a further binding site of a single bond linking the NRCT emitter moiety M NRCT to the bridging unit L,

deuterium,

N(R NRCT5 ) 2 ,

OR NRCT5 ,

Si(R NRCT5 ) 3 ,

B(OR NRCT5 ) 2 ,

OSO 2 R NRCT5 ,

CF 3 ,

CN,

halogen,

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R NRCT5 and

wherein one CH 2 -group or more than one non-adjacent CH 2 -groups are each optionally substituted by R NRCT5 C═CR NRCT5 , C≡C, Si(R NRCT5 ) 2 , Ge(R NRCT5 ) 2 , Sn(R NRCT5 ) 2 , C═O, C═S, C═Se, C═NR NRCT5 , P(═O)(R NRCT5 ), SO, SO 2 , NR NRCT5 , O, S or CONR NRCT5 ;

C 1 -C 40 -alkoxy,

which is optionally substituted with one or more substituents R NRCT5 and

C 1 -C 40 -thioalkoxy,

which is optionally substituted with one or more substituents R NRCT5 and

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R NRCT5 and

C 2 -C 40 -alkynyl,

which is optionally substituted with one or more substituents R NRCT5 and

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R NRCT5 , and

C 3 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R NRCT5 ;

R NRCT5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF 3 , CN, F,

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)(C 6 -C 18 -aryl),

N(C 3 -C 17 -heteroaryl)(C 3 -C 17 -heteroaryl); and

N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

R NRCT6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F,

the binding site of a single bond linking M NRCT to the bridging unit L,

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)(C 6 -C 18 -aryl),

N(C 3 -C 17 -heteroaryl)(C 3 -C 17 -heteroaryl); and

N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

wherein two or more of the substituents selected from the group consisting of R 1 , R 2 , R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI and, as far as present, R VII and R VIII that are positioned adjacent to another may each form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with another, may form a ring system and/or R 2 and R IV may form a ring system;

wherein at least one of X 1 , X 2 and X 3 is B and at least one of X 1 , X 2 and X 3 is N;

and wherein exactly one more of the substituents selected from the group consisting of R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI and, as far as present, R VII and R VIII represents the binding site of a single bond linking the NRCT emitter moiety M NRCT to the bridging unit L.

2 . The organic molecule according to claim 1 , wherein L comprises or consists of one or more consecutively linked divalent moieties selected from the group consisting of

C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

R L Si(R L 2 );

Si(R L 2 )R L ;

Si(R L 2 ); and

R L Si(R L 2 )R L ;

wherein R L is at each occurrence independently from another selected from the group consisting of

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CN, CF 3 and Ph;

pyridinyl or pyridinylene, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CN, CF 3 or Ph;

pyrimidinyl or pyrimidinylene, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CN, CF 3 and Ph;

carbazolyl or carbazolylene, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CN, CF 3 and Ph;

triazinyl or triazinylene, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CN, CF 3 and Ph; and

N(Ph) 2 .

3 . The organic molecule according to claim 1 , wherein L is selected from the group consisting of:

C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

C 6 -C 60 -arylene-C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene-C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 6 -C 60 -arylene-C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene-C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

C 6 -C 60 -arylene-C 3 -C 57 -heteroarylene-C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene-C 6 -C 60 -arylene-C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

C 6 -C 60 -arylene-C 6 -C 60 -arylene-C 6 -C 60 -arylene, which is optionally substituted with one or more substituents R L ;

C 3 -C 57 -heteroarylene-C 3 -C 57 -heteroarylene-C 3 -C 57 -heteroarylene, which is optionally substituted with one or more substituents R L ;

R L Si(R L 2 );

Si(R L 2 )R L ;

Si(R L 2 ); and

R L Si(R L 2 )R L —;

wherein R L is at each occurrence independently from another selected from the group consisting of:

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;

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

pyridinyl or pyridinylene, 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 or pyrimidinylene, 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 or carbazolylene, 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 or triazinylene, 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 .

4 . The organic molecule according to claim 1 , wherein L is selected from the group consisting of structures of Formula L1 to L46:

wherein $ represents the binding site of the single bond linking L and M TADF and

§ represents the binding site of the single bond linking L and M NRCT ;

and R L2 is at each occurrence independently selected from the group consisting of H, deuterium, Me, i Pr, t Bu, Ph and pyridyl.

5 . The organic molecule according to claim 1 , wherein X 1 and X 3 each are N and X 2 is B.

6 . The organic molecule according to claim 1 , wherein X 1 and X 3 each are B and X 2 is N.

7 . The organic molecule according to claim 1 , wherein n=0.

8 . The organic molecule according to claim 1 , wherein each of R I , R II , R III , R IV , R V , R VI , R IX , R X , and R XI and, as far as present, R VII and R VIII , is independently from another selected from the group consisting of:

a binding site of the single bond linking the NRCT emitter moiety M NRCT to the bridging unit L;

hydrogen,

deuterium,

halogen,

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 ; and

R 1 and R 2 is each 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 NRCT6 ;

C 6 -C 30 -aryl,

which is optionally substituted with one or more substituents R NRCT6 ; and

C 3 -C 30 -heteroaryl,

which is optionally substituted with one or more substituents R NRCT6 ;

and wherein exactly one more of the substituents selected from the group consisting of

R I , R II , R II , R IV , R V , R VI , R IX , R X , and R XI and, as far as present, R VII and R VIII represents the binding site of a single bond linking the NRCT emitter moiety M NRCT to the bridging unit L.

9 . The organic molecule according to claim 1 , wherein R I or R II represents the binding site of the single bond linking the NRCT emitter moiety M NRCT to the bridging unit L.

10 . The organic molecule according to claim 1 , wherein the first chemical moiety consists of a structure of Formula Ia:

wherein R Di , T, W and Y are defined as in claim 1 ;

Q 5 is selected from the group consisting of N and C—H;

Q 6 is selected from the group consisting of N and C—H;

wherein at least one of Q 5 and Q 6 is N; and

wherein exactly one substituent selected from the group consisting of T and W represents the binding site of a single bond linking the first chemical moiety and the second chemical moiety.

11 . The organic molecule according to claim 1 , wherein the second chemical moiety comprises or consists of a structure of Formula IIb:

wherein R b is at each occurrence independently from another 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

C 1 -C 40 -alkoxy,

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

C 1 -C 40 -thioalkoxy,

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

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

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 .

12 . The organic molecule according to claim 1 , wherein the second chemical moiety comprises or consists of a structure of formula IIc:

wherein R b is at each occurrence independently from another 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

C 1 -C 40 -alkoxy,

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

C 1 -C 40 -thioalkoxy,

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

C 2 -C 40 -alkenyl,

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

C 2 -C 40 -alkynyl,

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

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 .

13 . The organic molecule according to claim 12 , wherein R b is at each occurrence independently from another selected from the group consisting of:

hydrogen,

deuterium

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 .

14 . A composition, comprising:

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

(b) one or more emitter and/or host compounds, which differ from the organic molecule according to claim 1 , and

15 . The composition according to claim 14 , satisfying the Condition A or B,

Condition A

E HOMO (H)>E HOMO (E),

Condition B

E LUMO (H)>E LUMO (E),

wherein E HOMO (H) represents a highest occupied molecular orbital energy of the host compound, E HOMO (E) represents a highest occupied molecular orbital energy of the emitter, E LUMO (H) represents a lowest unoccupied molecular orbital energy of the host compound, and E LUMO (E) represents a lowest unoccupied molecular orbital energy of the emitter.

16 . The composition according to claim 15 , comprising one or more further host compound, and satisfying the Condition C or D,

Condition C

E HOMO (H)>E HOMO (D),

Condition D

E LUMO (H)>E LUMO (D),

wherein E HOMO (H) represents a highest occupied molecular orbital energy of the host compound, E HOMO (D) represents a highest occupied molecular orbital energy of the further host compound, E LUMO (H) represents a lowest unoccupied molecular orbital energy of the host compound, and E LUMO (D) represents a lowest unoccupied molecular orbital energy of the further host compound.

17 . An optoelectronic device, comprising:

a substrate,

an anode, and

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

a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule according to claim 1 .

18 . An optoelectronic device, comprising:

a substrate,

an anode, and

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

a light-emitting layer, which is arranged between the anode and the cathode and which comprises the composition according to claim 16 .

19 . The organic molecule according to claim 1 , wherein M TADF and M NRCT meet Equation 1,

λ max (TADF)<λ max (NRCT), Equation 1

wherein λ max (TADF) represents an emission maximum of the spectrum of TADF material (M TADF -H(hydrogen)), and

λ max (NRCT) represents an emission maximum of the spectrum of NRCT material (M NRCT -H(hydrogen)).

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2024

From: SEIFERMANN, STEFAN; FLUEGGE, HARALD; BONUS, SANDRA

To: CYNORA GMBH

Reel/Frame 066196/0222 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2024

From: CYNORA GMBH

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 066196/0267 →

Priority Claims (1)

EP 19189024 · Jul 30, 2019 · regional

Continuity (2)

Continuation 16936494 · Jul 23, 2020

Related Publication 20240188426A1 · Jun 6, 2024

References Cited (51)

US 7829204B2 · Iwakuma · 2010 [cited by examiner]

US 11165035B2 · Liaptsis et al. · 2021 [cited by applicant]

US 11462692B2 · Fluegge et al. · 2022 [cited by applicant]

US 11545632B2 · Seifermann · 2023 [cited by applicant]

US 11683978B2 · Dück · 2023 [cited by examiner]

US 11944005B2 · Seifermann · 2024 [cited by examiner]

US 20150236274A1 · Hatakeyama · 2015 [cited by examiner]

US 20170183360A1 · Ishii et al. · 2017 [cited by applicant]

US 20180062085A1 · Bergmann · 2018 [cited by examiner]

US 20180301629A1 · Hatakeyama et al. · 2018 [cited by applicant]

US 20190378982A1 · He et al. · 2019 [cited by applicant]

US 20200035922A1 · Ogiwara et al. · 2020 [cited by applicant]

US 20200176679A1 · Jeong et al. · 2020 [cited by applicant]

US 20200203617A1 · Duan et al. · 2020 [cited by applicant]

US 20200203651A1 · Duan et al. · 2020 [cited by applicant]

US 20200203652A1 · Duan et al. · 2020 [cited by applicant]

US 20200303662A1 · Seifermann · 2020 [cited by applicant]

US 20200347081A1 · Gao · 2020 [cited by examiner]

US 20200361961A1 · Zink et al. · 2020 [cited by applicant]

US 20210013413A1 · Dück · 2021 [cited by examiner]

US 20210277026A1 · Geum · 2021 [cited by examiner]

US 20220052266A1 · Li et al. · 2022 [cited by applicant]

US 20230033974A1 · Fluegge et al. · 2023 [cited by applicant]

US 20230157169A1 · Zink et al. · 2023 [cited by applicant]

CN 108358905A · 2018 [cited by applicant]

CN 109192874A · 2019 [cited by applicant]

CN 110003258A · 2019 [cited by examiner]

EP 2182040A2 · 2010 [cited by applicant]

EP 3109253A1 · 2016 [cited by applicant]

EP 19185839A · 2019 [cited by examiner]

JP 2017126606A · 2017 [cited by examiner]

JP 2018061029A · 2018 [cited by applicant]

KR 101876763B1 · 2018 [cited by applicant]

KR 1020180085936 · 2018 [cited by examiner]

WO WO2018095394A1 · 2018 [cited by applicant]

WO WO2018181188A1 · 2018 [cited by applicant]

WO WO2019002355A1 · 2019 [cited by examiner]

WO WO2019052939A1 · 2019 [cited by applicant]

WO WO2019120125A1 · 2019 [cited by applicant]

WO WO2020022770A1 · 2020 [cited by applicant]

WO WO2021008374A1 · 2021 [cited by applicant]

M. Colella et al., 10 ACS Applied Materials & Interfaces, 40001-40007 (2018) (Year: 2018). [cited by examiner]

F. Dias et al., 5 Methods and Applications in Fluorescence, 1-25 (2017) (Year: 2017). [cited by examiner]

M. Mamada et al., 3 ACS Central Science, 769-777 (2017) (Year: 2017). [cited by examiner]

H. Uoyama et al., 492 Nature (2012) (Year: 2012). [cited by examiner]

A. Arjona-Esteban et al., Chapter 15, Status and next steps of TADF technology: An industrial perspective, in Highly Efficient OLEDS: Materials Based on Thermally Activated Delayed Fluorescence, 543-572 (2018) (Year: 20… [cited by examiner]

Chen et al., 9 The Journal of Physical Chemistry Letters, 5240-5245 (2018) (Year: 2018). [cited by examiner]

J. Lakowicz, Instrumentation for fluorescence spectroscopy, in Principles of fluorescence spectroscopy, 25-61 (1999) (Year: 1999). [cited by examiner]

Hatakeyama, Takuji et al.; “Ultrapure Blue Thermally Activated Delayed Fluorescence Molecules: Efficient HOMO-LUMO Separation by the Multiple Resonance Effect”; Adv. Mater.; 2016; 28(14); pp. 2777-2781. [cited by applicant]

Liang, Xiao et al.; “Peripheral Amplification of Multi-Resonance Induced Thermally Activated Delayed Fluorescence for Highly Efficient OLEDs”; Angew. Chem. Int. Ed.; 2018; 57(35); pp. 11316-11320. [cited by applicant]

Okinaka, Keiji et al.; New Fluorescent Blue Host Materials for Achieving Low Voltage in OLEDs; SID 2015 Digest; pp. 312-315. [cited by applicant]