Organic molecules in particular for use in optoelectronic devices

An organic molecule represented by Formula A:

• wherein
• L represents a divalent bridging unit that links MTADF and MNRCT and is linked to MTADF and to MNRCT via a single bond each, and
• wherein MTADF 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), 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,
• the binding site of a single bond linking the TADF moiety MTADF to the bridging unit L, H, D, and RTADF1:
• 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, 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 consisting of 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—RQIII;
• 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,
• 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;
• 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, 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, 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 or consisting of a structure of Formula Q,
• the other RDi is selected from the group consisting of H, D, Me, iPr, tBu, 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, 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,
• B(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,
• B(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 R5C═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)2, 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)2, 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)2, 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 MNRCT consists of 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;
• and
• 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, 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, 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 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 R2 and RIV may 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, RV, 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.