Organic molecules for optoelectronic devices

An organic molecule, comprising:

• a first chemical moiety comprising a structure of formula I-a:
• and
• a second chemical moiety, comprising a structure of formula II:
• wherein:
• the first chemical moiety is linked to the second chemical moiety via a single bond;
• T is the binding site of a single bond linking the first chemical moiety to the second chemical moiety, or is selected from the group consisting of R2 and RX;
• V is the binding site of a single bond linking the first chemical moiety to the second chemical moiety, or is hydrogen (H);
• W is the binding site of a single bond linking the first chemical moiety to the second chemical moiety, or is selected from the group consisting of R2 and RX;
• X is selected from the group consisting of R2 and RX;
• Y is selected from the group consisting of R2 and RX;
• RX is selected from the group consisting of CN and CF3 or RX comprises a structure of formula BN-I,
• which is bonded to the structure of formula I-a via a single bond indicated by the dashed line and wherein exactly one group RBN is CN while the other two groups RBN are both hydrogen (H);
• R1 is selected from the group consisting of:
• hydrogen, deuterium, OR3, Si(R3)3, B(OR3)2, OSO2R3, CF3, CN, F, Cl, Br, I, C1-C40-alkyl,
• which is optionally substituted with one or more substituents R3 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R3 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R3 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R3 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R3 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR7, P(═O)(R3), SO, SO2, NR3, O, S or CONR3;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R3;
• R2 is at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium,
• C1-C10-alkyl,
• wherein one or more hydrogen atoms are optionally substituted by deuterium;
• C2-C10-alkenyl,
• wherein one or more hydrogen atoms are optionally substituted by deuterium;
• C2-C10-alkynyl,
• wherein one or more hydrogen atoms are optionally substituted by deuterium;
• C5-C10-aryl;
• wherein one or more hydrogen atoms are optionally substituted by a group R5;
• R3 is at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, N(R4)2, OR4, Si(R4)3, B(OR4)2, OSO2R4, CF3, CN, F, Cl, Br, I, C1-C40-alkyl,
• which is optionally substituted with one or more substituents R4 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R4 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R4 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R4 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R4 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R4;
• and
• C3-C60-heteroaryl,
• which is optionally substituted with one or more substituents R4;
• Ra, Rb, Rc, Rd, R6, and R7 are at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, N(R8)2, OR8, Si(R8)3, B(OR8)2, OSO2R8, CF3, CN, F, Cl, Br, I,
• C1-C40-alkyl,
• which is optionally substituted with one or more substituents R8 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R8C═CR8, C≡C, Si(R8)2, Ge(R8)2, Sn(R8)2, C═O, C═S, C═Se, C═NR8, P(═O)(R8), SO, SO2, NR8, O, S or CONR8;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R8 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R8C═CR8, C≡C, Si(R8)2, Ge(R8)2, Sn(R8)2, C═O, C═S, C═Se, C═NR8, P(═O)(R8), SO, SO2, NR8, O, S or CONR8;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R8 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R8C═CR8, C≡C, Si(R8)2, Ge(R8)2, Sn(R8)2, C═O, C═S, C═Se, C═NR8, P(═O)(R8), SO, SO2, NR8, O, S or CONR8;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R8 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R8C═CR8, C≡C, Si(R8)2, Ge(R8)2, Sn(R8)2, C═O, C═S, C═Se, C═NR8, P(═O)(R8), SO, SO2, NR8, O, S or CONR8;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R8 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R8C═CR8, C≡C, Si(R8)2, Ge(R8)2, Sn(R8)2, C═O, C═S, C═Se, C═NR8, P(═O)(R8), SO, SO2, NR8, O, S or CONR8;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R8;
• and
• C3-C60-heteroaryl,
• which is optionally substituted with one or more substituents R8;
• wherein, optionally, two moieties Rb form a group Y, which is selected from the group consisting of a direct bond, CR6R7, C═CR6R7, C═O, C═NR6, NR6, O, SiR6R7, S, S(O) and S(O)2;
• R8 is at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, N(R9)2, OR9, Si(R9)3, B(OR9)2, OSO2R9, CF3, CN, F, Cl, Br, I, C1-C40-alkyl,
• which is optionally substituted with one or more substituents R9 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R9C═CR9, C≡C, Si(R9)2, Ge(R9)2, Sn(R9)2, C═O, C═S, C═Se, C═NR9, P(═O)(R9), SO, SO2, NR9, O, S or CONR9;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R9 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R9C═CR9, C≡C, Si(R9)2, Ge(R9)2, Sn(R9)2, C═O, C═S, C═Se, C═NR9, P(═O)(R9), SO, SO2, NR9, O, S or CONR9;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R9 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R9C═CR9, C≡C, Si(R9)2, Ge(R9)2, Sn(R9)2, C═O, C═S, C═Se, C═NR9, P(═O)(R9), SO, SO2, NR9, O, S or CONR9;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R9 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R9C═CR9, C≡C, Si(R9)2, Ge(R9)2, Sn(R9)2, C═O, C═S, C═Se, C═NR9, P(═O)(R9), SO, SO2, NR9, O, S or CONR9;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R9 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R9C═CR9, C≡C, Si(R9)2, Ge(R9)2, Sn(R9)2, C═O, C═S, C═Se, C═NR9, P(═O)(R9), SO, SO2, NR9, O, S or CONR9;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R9;
• and
• C3-C57-heteroaryl,
• which is optionally substituted with one or more substituents R9;
• wherein, optionally, any of the substituents selected from the group consisting of Ra, Rb, Rc, Rd, R6, R7, and R8 independently form a mono- or polycyclic, aliphatic or aromatic, carbo- or heterocyclic and/or benzo-fused ring or ring system with one or more adjacent substituents selected from the group consisting of Ra, Rb, Rc, Rd, R6, R7, and R8;
• wherein the formed additional ring or rings are optionally substituted with one or more substituents R10;
• #represents the binding site of the first chemical moiety to the second chemical moiety;
• Z is selected from the group consisting of a direct bond, CR11R12, C═CR11R12, C═O, C═NR11, NR11, O, SiR11R12, S, S(O), and S(O)2;
• Re, Rf, Rg, R11, and R12 are at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, N(R13)2, OR13, Si(R13)3, B(OR13)2, OSO2R13, CF3, CN, F, Cl, Br, I,
• C1-C40-alkyl,
• which is optionally substituted with one or more substituents R13 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R13 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R13 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R13 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R13 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R13;
• and
• C3-C60-heteroaryl,
• which is optionally substituted with one or more substituents R13;
• R13 is at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, N(R14)2, OR14, Si(R14)3, B(OR14)2, OSO2R14, CF3, CN, F, Br, I, C1-C40-alkyl,
• which is optionally substituted with one or more substituents R14 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14;
• C1-C40-alkoxy,
• which is optionally substituted with one or more substituents R14 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14;
• C1-C40-thioalkoxy,
• which is optionally substituted with one or more substituents R14 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14;
• C2-C40-alkenyl,
• which is optionally substituted with one or more substituents R14 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14;
• C2-C40-alkynyl,
• which is optionally substituted with one or more substituents R14 and
• wherein one or more non-adjacent CH2-groups are optionally substituted by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14;
• C6-C60-aryl,
• which is optionally substituted with one or more substituents R14;
• and
• C3-C57-heteroaryl,
• which is optionally substituted with one or more substituents R14;
• wherein, optionally, any of the substituents selected from the group consisting of Re, Rf, Rg, R11, R12, and R13 independently form a mono- or polycyclic, aliphatic or aromatic, carbo- or heterocyclic and/or benzo-fused ring or ring system with one or more adjacent substituents selected from selected from the group consisting of Re, Rf, Rg, R11, R12, and R13;
• wherein the formed additional ring or rings are optionally substituted with one or more substituents R15;
• R4, R9, R10, R14, and R15 are at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, OPh, CF3, CN, F,
• C1-C5-alkyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C1-C5-alkoxy,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C1-C5-thioalkoxy,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C2-C5-alkenyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C2-C5-alkynyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C3-C18-aryl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, C1-C5-alkyl, Ph or CN;
• C3-C15-heteroaryl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, Ph or C1-C5-alkyl;
• N(C6-C18-aryl)2;
• N(C3-C17-heteroaryl)2, and
• N(C3-C17-heteroaryl)(C6-C18-aryl);
• R5 is at each occurrence independently selected from the group consisting of:
• hydrogen, deuterium, OPh, CF3, F,
• C1-C5-alkyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C1-C5-alkoxy,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C1-C5-thioalkoxy,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C2-C5-alkenyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C2-C5-alkynyl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
• C6-C18-aryl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, C1-C5-alkyl, Ph or CN;
• C3-C15-heteroaryl,
• wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, Ph or C1-C5-alkyl;
• N(C6-C18-aryl)2;
• N(C3-C17-heteroaryl)2, and
• N(C3-C17-heteroaryl)(C6-C18-aryl);
• and wherein:
• exactly one substituent selected from the group consisting of T, W, X, and Y is RX, and exactly one substituent selected from the group consisting of T, V, and W represents the binding site of a single bond linking the first chemical moiety to the second chemical moiety;
• and
• wherein W is hydrogen (H), if T is RX and V is the binding site of a single bond linking the first chemical moiety and the second chemical moiety.