Patent ID: 11944005
Assignee: SAMSUNG ELECTRONICS CO., LTD.
Field: Organic fine chemistry (Chemistry)
Classification: CPC H  C  Y | IPC C  H

Claim 0:
1. An organic molecule, comprising Formula A:, wherein
MTADF represents a TADF moiety;
MNRCT represents a near-range charge transfer (NRCT) emitter moiety; and
L represents a divalent bridging unit that links MTADF and MNRCT and is linked to MTADF and to MNRCT via a single bond each,
wherein MNRCT comprises a structure according to Formula NRCT I:, wherein
n is 0 or 1;
m=1-n;
X1 is N or B;
X2 is N or B;
X3 is N or B;
W, if present, is selected from the group consisting of Si(RNRCT3)2, C(RNRCT3)2, and BRNRCT3;
each of R1, R2, and RNRCT3 is independently from each other selected from the group consisting of:
C6-C60-aryl, which is optionally substituted with one or more substituents RNRCT6;
C1-C5-alkyl, which is optionally substituted with one or more substituents RNRCT6; and
C3-C57-heteroaryl, which is optionally substituted with one or more substituents RNRCT6;

wherein at least one of RI, RII, RIII, RIV, RV, RVI, RVII, RVIII, RIX, RX, and RXI is a binding site of a single bond linking the NRCT emitter moiety MNRCT to the bridging unit L;
the further residues RI, RII, RIII, RIV, RV, RVI, RIX, RX, and RXI and, as far as present, RVII and RVIII, 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 MNRCT to the bridging unit L;
deuterium;
N(RNRCT5)2;
ORNRCT5;
Si(RNRCT5)3;
B(ORNRCT5)2;
OSO2RNRCT5;
CF3;
CN;
Halogen;
C1-C40-alkyl,
which is optionally substituted with one or more substituents RNRCT5 and wherein one CH2-group or more than one non-adjacent CH2-groups are each optionally substituted by RNRCT5C═CRNRCT5, C≡C, Si(RNRCT5)2, Ge(RNRCT5)2, Sn(RNRCT5)2, C═O, C═S, C═Se, C═NRNRCT5, p(═O)(RNRCT5), SO, SO2, NRNRCT5, O, S, or CONRNRCT5;

C1-C40-alkoxy,
which is optionally substituted with one or more substituents RNRCT5 and wherein one CH2-group or more than one non-adjacent CH2-groups are each optionally substituted by RNRCT5C═CRNRCT5, C≡C, Si(RNRCT5)2, Ge(RNRCT5)2, Sn(RNRCT5)2, C═O, C═S, C═Se, C═NRNRCT5, P(═O)(RNRCT5), SO, SO2, NRNRCT5, O, S, or CONRNRCT5;

C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents RNRCT5 and wherein one CH2-group or more than one non-adjacent CH2-groups are each optionally substituted by RNRCT5C═CRNRCT5, C≡C, Si(RNRCT5)2, Ge(RNRCT5)2, Sn(RNRCT5)2, C═O, C═S, C═Se, C═NRNRCT5, P(═O)(RNRCT5), SO, SO2, NRNRCT5, O, S, or CONRNRCT5;

C2-C40-alkenyl,
which is optionally substituted with one or more substituents RNRCT5 and wherein one CH2-group or more than one non-adjacent CH2-groups are each optionally substituted by RNRCT5C═CRNRCT5, C≡C, Si(RNRCT5)2, Ge(RNRCT5)2, Sn(RNRCT5)2, C═O, C═S, C═Se, C═NRNRCT5, P(═O)(RNRCT5), SO, SO2, NRNRCT5, O, S, or CONRNRCT5;

C2-C40-alkynyl,
which is optionally substituted with one or more substituents RNRCT5 and wherein one CH2-group or more than one non-adjacent CH2-groups are each optionally substituted by RNRCT5C═CRNRCT5, C≡C, Si(RNRCT5)2, Ge(RNRCT5)2, Sn(RNRCT5)2, C═O, C═S, C═Se, C═NRNRCT5, P(═O)(RNRCT5), SO, SO2, NRNRCT5, O, S, or CONRNRCT5;

C6-C60-aryl,
which is optionally substituted with one or more substituents RNRCT5; and

C3-C57-heteroaryl,
which is optionally substituted with one or more substituents RNRCT5;

RNRCT5 is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, OPh, CF3, CN, and F;
C1-C5-alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-alkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-thioalkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkenyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C6-C18-aryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

C3-C17-heteroaryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

N(C6-C18-aryl)(C6-C18-aryl);
N(C3-C17-heteroaryl)(C3-C17-heteroaryl); and
N(C3-C17-heteroaryl)(C6-C18-aryl);

RNRCT6 is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, OPh, CF3, CN, and F;
the binding site of a single bond linking MNRCT to the bridging unit L;
C1-C5-alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-alkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-thioalkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkenyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C6-C18-aryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

C3-C17-heteroaryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

N(C6-C18-aryl)(C6-C18-aryl);
N(C3-C17-heteroaryl)(C3-C17-heteroaryl); and
N(C3-C17-heteroaryl)(C6-C18-aryl);

wherein two or more of the substituents selected from the group consisting of R1, R2, RI, RII, RIII, RIV, RV, RVI, RIX, RX, and RXI and, as far as present, RVII and RVIII 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 R2 and RIV optionally form a ring system;
wherein at least one of X1, X2, and X3 is B and at least one of X1, X2, and X3 is N; and
wherein exactly one more of the substituents selected from the group consisting of RI, RII, RIII, RIV, RVI, RIX, RX, and RXI and, as far as present, RVII and RVIII represents the binding site of a single bond linking the NRCT emitter moiety MNRCT to the bridging unit L, and
wherein MTADF 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), RTADF1, 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, RTADF1, and the binding site of a single bond linking the TADF moiety MTADF to the bridging unit L;

Y is selected from the group consisting of:
H, D, RTADF1, and the binding site of a single bond linking the TADF moiety MTADF to the bridging unit L;

Acc1 is selected from the group consisting of:
triazinyl, which is optionally substituted with one or more substituents R6;
CN;
CF3;
Ph,
which is optionally substituted with one or more substituents selected from the group consisting of CN, CF3, and F;

pyridyl,
which is optionally substituted with one or more substituents R6; and

pyrimidyl,
which is optionally substituted with one or more substituents R6;

# represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety;
RDi is selected from the group consisting of the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L, H, D, Me, iPr, tBu, SiPh3, CN, and CF3;
Ph,
which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph; and

a third chemical moiety comprising a structure of Formula Q:, wherein:
Q1 is selected from the group consisting of N and C—RQI;
Q2 is selected from the group consisting of N and C—RQII;
Q3 is selected from the group consisting of N and C—RQIV;
Q4 is selected from the group consisting of N and C—RQV; and
$Q represents the binding site of a single bond linking the third chemical moiety to the first chemical moiety;
RQI is selected from the group consisting of:
H;
D;
CN;
CF3;
SiPh3;
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;
RQII is selected from the group consisting of:
the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L;
H, D, Me, iPr, tBu, and SiPh3; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph;

RQIII is selected from the group consisting of:
the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L;
H;
D;
CN;
CF3;
SiPh3;
F;
Ph, which is optionally substituted with one or more substituents R6;
triazinyl, which is optionally substituted with one or more substituents R6;
pyridyl, which is optionally substituted with one or more substituents R6; and
pyrimidyl, which is optionally substituted with one or more substituents R6;

RQIV is selected from the group consisting of:
the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L;
H;
D;
CN;
CF3;
SiPh3;
F;
Ph, which is optionally substituted with one or more substituents R6;
triazinyl, which is optionally substituted with one or more substituents R6;
pyridyl, which is optionally substituted with one or more substituents R6; and
pyrimidyl, which is optionally substituted with one or more substituents R6;

RQV is selected from the group consisting of:
the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L;
H, D, Me, iPr, tBu, and SiPh3; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph;

wherein in case one RDi represents the third chemical moiety comprising a structure of Formula Q,
the other RDi is selected from the group consisting of H, D, Me, iPr, tBu, and SiPh3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph, and
the binding site of the single bond linking the TADF moiety MTADF to the bridging unit L;

RTADF1 is selected from the group consisting of:
Me, iPr, tBu, and SiPh3, and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph;

Ra at each occurrence independently from another selected from the group consisting of:
H;
D;
N(R5)2;
OR5;
Si(R5)3;
S(OR5)2;
OSO2R5;
CF3;
CN;
F;
Br;
I;
C1-C40-alkyl,
which is optionally substituted with one or more substituents R5 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5;

C1-C40-alkoxy,
which is optionally substituted with one or more substituents R5 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5;

C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R5 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5;

C2-C40-alkenyl,
which is optionally substituted with one or more substituents R5 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5;

C2-C40-alkynyl,
which is optionally substituted with one or more substituents R5 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5;

C6-C60-aryl,
which is optionally substituted with one or more substituents R5; and

C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5;

R5 is at each occurrence independently from another selected from the group consisting of:
H;
D;
N(R6)2;
OR6;
Si(R6)3;
S(OR6)2;
OSO2R6;
CF3;
CN;
F;
Br;
I;
C1-C40-alkyl,
which is optionally substituted with one or more substituents R6 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S, or CONR6;

C1-C40-alkoxy,
which is optionally substituted with one or more substituents R6 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S, or CONR6;

C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R6 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S, or CONR6;

C2-C40-alkenyl,
which is optionally substituted with one or more substituents R6 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S, or CONR6;

C2-C40-alkynyl,
which is optionally substituted with one or more substituents R6 and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S, or CONR6;

C6-C60-aryl,
which is optionally substituted with one or more substituents R6; and

C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R6;

R6 is at each occurrence independently from another selected from the group consisting of:
C6-C18-aryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
Hydrogen;
Deuterium;
Oph;
CF3;
CN;
F;
C1-C5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C3-C17-heteroaryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
N(C6-C18-aryl)(C6-C18-aryl);
N(C3-C17-heteroaryl)(C3-C17-heteroaryl); and
N(C3-C17-heteroaryl)(C6-C18-aryl);

wherein two or more of the substituents Ra and/or R5 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 Ra or R5;
Rf is at each occurrence independently from another selected from the group consisting of:
H:
D;
N(R5f)2;
OR5f;
Si(R5f)3;
B(OR5f)2;
OSO2R5f;
CF3;
CN;
F;
Br;
I;
C1-C40-alkyl,
which is optionally substituted with one or more substituents R5f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5fC═CR5f, C≡C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C═S, C═Se, C═NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S, or CONR5f;

C1-C40-alkoxy,
which is optionally substituted with one or more substituents R5f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5fC═CR5f, C≡C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C═S, C═Se, C═NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S, or CONR5f;

C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R5f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5fC═CR5f, C≡C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C═S, C═Se, C═NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S, or CONR5f;

C2-C40-alkenyl,
which is optionally substituted with one or more substituents R5f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5fC═CR5f, C≡C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C═S, C═Se, C═NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S, or CONR5f;

C2-C40-alkynyl,
which is optionally substituted with one or more substituents R5f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R5fC═CR5f, C≡C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C═S, C═Se, C═NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S, or CONR5f;

C6-C60-aryl,
which is optionally substituted with one or more substituents R5f; and

C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5f;

R5f is at each occurrence independently from another selected from the group consisting of:
H;
D;
N(R6f)2;
OR6f;
Si(R6f)3;
B(OR6f)2;
OSO2R6f;
CF3;
CN;
F;
Br;
I;
C1-C40-alkyl,
which is optionally substituted with one or more substituents R6f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6fC═CR6f, C≡C, Si(R6f)2, Ge(R6f)2, Sn(R6f)2, C═O, C═S, C═Se, C═NR6f, P(═O)(R6f), SO, SO2, NR6f, O, S, or CONR6f;

C1-C40-alkoxy,
which is optionally substituted with one or more substituents R6f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6fC═CR6f, C≡C, Si(R6f)2, Ge(R6f)2, Sn(R6f), C═O, C═S, C═Se, C═NR6f, P(═O)(R6f), SO, SO2, NR6f, O, S, or CONR6f;

C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R6f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6fC═CR6f, C≡C, Si(R6f)2, Ge(R6f)2, Sn(R6f), C═O, C═S, C═Se, C═NR6f, P(═O)(R6f), SO, SO2, NR6f, O, S, or CONR6f;

C2-C40-alkenyl,
which is optionally substituted with one or more substituents R6f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6fC═CR6f, C≡C, Si(R6f)2, Ge(R6f)2, Sn(R6f), C═O, C═S, C═Se, C═NR6f, P(═O)(R6f), SO, SO2, NR6f, O, S, or CONR6f;

C2-C40-alkynyl,
which is optionally substituted with one or more substituents R6f and wherein one CH2-group or more than one non-adjacent CH2-groups are optionally substituted by R6fC═CR6f, C≡C, Si(R6f)2, Ge(R6f)2, Sn(R6f)2, C═O, C═S, C═Se, C═NR6f, P(═O)(R6f), SO, SO2, NR6f, O, S, or CONR6f;

C6-C60-aryl,
which is optionally substituted with one or more substituents R6f; and

C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R6f;

R6f is at each occurrence independently from another selected from the group consisting of:
H;
D;
OPh;
CF3;
CN;
F;
C1-C5-alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-alkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C1-C5-thioalkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkenyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C2-C5-alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;

C6-C18-aryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

C3-C17-heteroaryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;

N(C6-C18-aryl)(C6-C18-aryl);
N(C3-C17-heteroaryl)(C3-C17-heteroaryl); and
N(C3-C17-heteroaryl)(C6-C18-aryl);

wherein two or more of the substituents Rf and/or R5f 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 Rf or R5f;
wherein MTADF contains exactly one binding site of the single bond linking the TADF moiety MTADF 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 MTADF;
§ represents the binding site of the single bond linking L and MNRCT; and
RL2 at each occurrence independently selected from the group consisting of H, deuterium, Me, iPr, tBu, Ph, and pyridyl.