IP Library › Granted Patent US 11,944,005

Granted Patent B2

US 11,944,005 · App. 16/936,494 · Granted Mar 26, 2024

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.

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

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Quick Facts

Patent No.: US 11,944,005
App. No.: 16/936,494
Granted: Mar 26, 2024
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 (463)

1. An organic molecule, comprising 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,

wherein M NRCT comprises 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 ;

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 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 -thioalkoxy,

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 2 -C 40 -alkenyl,

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 2 -C 40 -alkynyl,

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 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, and 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, and 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 optionally each form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with another, optionally form a ring system and/or R 2 and R IV optionally 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 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, and

wherein M TADF comprises

a first chemical moiety comprising a structure according to Formula I,

and

a second chemical moiety comprising 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; and

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

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, and 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 comprising 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 QII ;

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 ;

F; and

Ph; and

a fourth chemical moiety comprising a structure of Formula IIQ:

wherein:

§ 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, and 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, and 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 a structure of Formula Q,

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

S(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,

C 1 -C 40 -thioalkoxy,

C 2 -C 40 -alkenyl,

C 2 -C 40 -alkynyl,

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:

N(R 6 ) 2 ;

OR 6 ;

Si(R 6 ) 3 ;

S(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,

C 1 -C 40 -thioalkoxy,

C 2 -C 40 -alkenyl,

C 2 -C 40 -alkynyl,

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:

N(R 5f ) 2 ;

OR 5f ;

Si(R 5f ) 3 ;

B(OR 5f ) 2 ;

OSO 2 R 5f ;

CF 3 ;

CN;

Br;

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,

C 1 -C 40 -thioalkoxy,

C 2 -C 40 -alkenyl,

C 2 -C 40 -alkynyl,

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:

N(R 6f ) 2 ;

OR 6f ;

Si(R 6f ) 3 ;

B(OR 6f ) 2 ;

OSO 2 R 6f ;

CF 3 ;

CN;

Br;

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 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 ), 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 -thioalkoxy,

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 ), C═O, C═S, C═Se, C═NR 6f , P(═O)(R 6f ), SO, SO 2 , NR 6f , O, S, or CONR 6f ;

C 2 -C 40 -alkenyl,

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 ), C═O, C═S, C═Se, C═NR 6f , P(═O)(R 6f ), SO, SO 2 , NR 6f , O, S, or CONR 6f ;

C 2 -C 40 -alkynyl,

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:

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 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 ;

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

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

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

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

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

5. 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 ;

wherein R 1 and R 2 are 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 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.

6. 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.

7. The organic molecule according to claim 1 , wherein the first chemical moiety comprises 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 6b 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.

8. The organic molecule according to claim 1 , wherein the second chemical moiety comprises 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;

Br;

C 1 -C 40 -alkyl,

C 1 -C 40 -alkoxy,

C 1 -C 40 -thioalkoxy,

C 2 -C 40 -alkenyl,

C 2 -C 40 -alkynyl,

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 .

9. The organic molecule according to claim 1 , wherein the second chemical moiety comprises 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 ;

S(OR 5 ) 2 ;

OSO 2 R 5 ;

CF 3 ;

CN;

Br;

C 1 -C 40 -alkyl,

C 1 -C 40 -alkoxy,

C 1 -C 40 -thioalkoxy,

C 2 -C 40 -alkenyl,

C 2 -C 40 -alkynyl,

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 .

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

hydrogen;

deuterium;

Me, i Pr, t Bu, CN, and 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 .

11. An optoelectronic device comprising a luminescent emitter, wherein the luminescent emitter comprises the organic molecule according to claim 1 .

12. The optoelectronic device according to claim 11 , wherein the optoelectronic 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.

13. A composition comprising:

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

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

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

15. An optoelectronic device, comprising the composition according to claim 13 .

16. An optoelectronic device, comprising the organic molecule according to claim 1 , wherein the optoelectronic device is in the form of a device 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.

17. An optoelectronic device, comprising the composition according to claim 13 , wherein the optoelectronic device is in the form of a device 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 14 , comprising

a substrate;

an anode;

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.

19. The optoelectronic device according to claim 15 , comprising a substrate;

an anode;

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.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2022

From: CYNORA GMBH

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 060329/0712 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2020

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

To: CYNORA GMBH

Reel/Frame 053943/0070 →

Priority Claims (1)

EP 19189024 · Jul 30, 2019 · regional

Continuity (1)

Related Publication 20210036235A1 · Feb 4, 2021