Organic semiconducting compounds for use in organic electronic devices

A compound having Formula IV-V:

• where M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R6)—, —C(R7)2—C(R8)2—, —CR7═CR8—, —S(═O)2—, —S(═O)—, —C(═O)—, —C(═S)—, or —C(═N—R1)—;
• where R1 is H or a substituent;
• R6 is H or a substituent;
• R7 is H or a substituent;
• R8 is H or a substituent;
• X1 is N or C—R9, Y1 is N or C—R9, one of X1 and Y1 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X2 is N or C—R9, Y2 is N or C—R9, one of X2 and Y2 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X3 is N or C—R9, Y3 is N or C—R9, one of X3 and Y3 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• Q is a trivalent aryl or heteroaryl group;
• each E1 is independently either nonentity, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl groups, or
• each L3 is, independently, —B2 or -A1-B2
• each A1 is independently selected from substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group,
• where A2 is independently a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group;
• each B2 is independently selected from H, a substituent, halogen, —Sn(C1-C4 alkyl)4, —Zn(halide),
• —Mg(halide), —B(OH)2, or boronate ester, or
• where n is an integer between 0 and 5, inclusive and m is an integer between 0 and 5, inclusive, and 1≦m+n≦5;
• and where R1, R2, R3, and R4 are each independently H or a substituent, R5 is H, a substituent, halogen, —Sn(C1-C4 alkyl)3, —Zn(halide), —Mg(halide), —B(OH)2, or boronate ester.

A compound having Formula VI-VII:

• where the moiety
• is a tetravalent aryl or heteroaryl group selected from
• (2, 2′,7,7′-yl-9,9′-spirobi[fluorene]),
• (3,3′,7,7′-yl-5,5′-spirobi[dibenzo[b,d]silole]),
• (2,2′,6,6′-yl-4,4″-spirobi[cyclopenta[1,2-b:5,4-b′]dithiophene]), or
• (2,2′,6,6′-yl-4,4′-spirobi[silolo[3,2-b:4,5-b′]dithiophene]);
• where M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R6)—, —C(R7)2—C(R8)2—, —CR7═CR8—, —S(═O)2—, —S(═O)—, —C(═O)—, —C(═S)—, or —C(═N—R1)—;
• where R1 is H or a substituent;
• R6 is H or a substituent;
• R7 is H or a substituent;
• R8 is H or a substituent;
• X1 is N or C—R9, Y1 is N or C—R9, one of X1 and Y1 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X2 is N or C—R9, Y2 is N or C—R9, one of X2 and Y2 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X3 is N or C—R9, Y3 is N or C—R9, one of X3 and Y3 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X4 is N or C—R9, Y4 is N or C—R9, one of X4 and Y4 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• each F1 is independently either nonentity, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl groups, or
• each L4 is, independently, —B2 or -A1-B2;
• each A1 is independently selected from substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group
• where A2 is independently a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group;
• each B2 is independently selected from H, a substituent,
• halogen, —Sn(C1-C4 alkyl)4, —Zn(halide),
• —Mg(halide), —B(OH)2, or boronate ester, or
• where n is an integer between 0 and 5, inclusive and m is an integer between 0 and 5, inclusive, and 1≦m+n≦5;
• and where R1, R2, R3, and R4 are each independently H or a substituent, R5 is H, a substituent,
• halogen, —Sn(C1-C4 alkyl)3, —Zn(halide), —Mg(halide), —B(OH)2, or boronate ester.

A compound selected from Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7, Formula 8, Formula 9 or Formula 10:

• where M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R6)—, —C(R7)2—C(R8)2—, —CR7═CR8—, —S(═O)2—, —S(═O)—, —C(═O)—, —C(═S)—, or —C(═N—R1)—;
• where R1 is H or a substituent;
• R6 is H or a substituent;
• R7 is H or a substituent;
• R8 is H or a substituent;
• X1 is N or C—R9, Y1 is N or C—R9, one of X1 and Y1 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X2 is N or C—R9, Y2 is N or C—R9, one of X2 and Y2 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• X3 is N or C—R9, Y3 is N or C—R9, one of X3 and Y3 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• n is an integer from 0 to 5 inclusive;
• m is an integer from 0 to 5 inclusive;
• R7 is selected from H or a substituent;
• J is selected from CH and N;
• X is S, O, or NH when X is CH;
• and X is S when J is N;
• R8 is C6-C30 aryl optionally substituted with one or more C1-C16 alkyl groups;
• R6 is selected from aryl, perfluoroaryl, or C6-C30 aryl optionally perfluorinated or optionally substituted with one or more C1-C16 alkyl groups;
• and
• each DONOR is an aryl or heteroaryl group independently selected from:
• where X is C or Si;
• A is N or P;
• R11 is selected from C1-C16 alkyl;
• R12 is selected from C1-C16 alkyl, C6-C20 unsubstituted aryl, or C6-C20 aryl substituted with one or more groups selected from —F, C1-C20 alkyl, C1-C20 fluoroalkyl, —O—C1-C20 alkyl, or —C1-C20 fluoroalkyl;
• R13 is selected from C1-C16 alkyl or C6-C20 aryl;
• R14 is selected from C1-C16 alkyl, —O—C—C16 alkyl, —C(═O)—O—C1-C16 alkyl, or —O—C(═O)—C1-C16 alkyl;
• and
• R15 is selected from C1-C16 alkyl, C6-C20 unsubstituted aryl, or C6-C20 aryl substituted with one or more groups selected from —F, C1-C20 alkyl, C1-C20 fluoroalkyl, —O—C1-C20 alkyl, or —C1-C20 fluoroalkyl;
• and
• R16 is selected from C1-C16 alkyl, C6-C20 unsubstituted aryl, or C6-C20 aryl substituted with one or more groups selected from —F, C1-C20 alkyl, C1-C20 fluoroalkyl, —O—C1-C20 alkyl, or —C1-C20 fluoroalkyl.

A compound of Formula B:

• where M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R6)—, —C(R7)2—C(R8)2—, —CR7═CR8—, —S(═O)2—, —S(═O)—, —C(═O)—, —C(═S)—, or —C(═N—R1)—;
• where R1 is H or a substituent;
• R6 is H or a substituent;
• R7 is H or a substituent;
• R8 is H or a substituent;
• X1 is N or C—R9, Y1 is N or C—R9, and one of X1 and Y1 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• H1 is selected from -A1-B1, -A1-B2, or
• n is an integer between 0 and 5, inclusive and m is an integer between 0 and 5, inclusive, and 1≦m+n≦5;
• A1 is independently selected from substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group,
• where A2 is independently a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group;
• each B1 is independently selected from a an aryl or heteroaryl groups substituted with one, two, or more B2;
• and
• each B2 is independently selected from a substituent, halogen, —Sn(C1-C4 alkyl)4, —Zn(halide),
• —Mg(halide), —B(OH)2, or boronate ester, or
• where n is an integer between 0 and 5, inclusive and m is an integer between 0 and 5, inclusive, and 1≦m+n≦5;
• and where R1, R2, R3, and R4 are each independently H or a substituent, R5 is H, a substituent, halogen, —Sn(C1-C4 alkyl)3, —Zn(halide), —Mg(halide), —B(OH)2, or boronate ester;
• H2 is selected from —B2, -A1-B1, -A1-B2,
• where p is 1, 2, or 3;
• each X2 is N or C—R9, Y2 is N or C—R9, one of X2 and Y2 is N, and the other is C—R9;
• where R9 is F, Cl, Br, or I;
• each J1 is independently selected from a nonentity, substituted or unsubstituted aryl,
• substituted or unsubstituted heteroaryl groups, or
• Q is a bivalent, trivalent, or tetravalent aryl or heteroaryl group or
• L1 is selected from —B2, -A1-B1, -A1-B2,
• where each A1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C6-C30 substituted or unsubstituted aryl or heteroaryl groups, C6-C20 substituted or unsubstituted aryl or heteroaryl groups, and C6-C10 substituted or unsubstituted aryl or heteroaryl groups;
• wherein the compound is a polymer.