Thiocyanato or isothiocyanato substituted naphthalene diimide and rylene diimide compounds and their use as n-type semiconductors

A compound of formula I:

• wherein:
• R1 and R2, at each occurrence, are independently H, a C1-30 alkyl group, a C2-30 alkenyl group, a C2-30 alkynyl group, a C1-30 haloalkyl group, or a 3-22 membered cyclic moiety, each optionally substituted with 1-4 groups independently selected from the group consisting of halogen, —CN, —NO2, —C(O)H, —C(O)OH, —CONH2, —OH, —NH2, —CO(C1-14 alkyl), —C(O)OC1-14 alkyl, —CONH(C1-14 alkyl), —CON(C1-14 alkyl)2, —S—C1-14 alkyl, —O—(CH2CH2O)n(C1-14 alkyl), —NH(C1-14 alkyl), —N(C1-14 alkyl)2, a C1-14 alkyl group, a C2-14 alkenyl group, a C2-14 alkynyl group, a C1-14 haloalkyl group, a C1-14 alkoxy group, a C6-14 aryl group, a C3-14 cycloalkyl group, a 3-14 membered cycloheteroalkyl group, and a 5-14 membered heteroaryl group;
• each R3 is independently a halogen, —CN, —NO2, —C(O)O(C1-14 alkyl), —C(O)O(C6-14 aryl), —CHO, C1-14 alkylsulfon, C6-14 arylsulfon, a sulfonic acid C1-14 alkylester or C6-14 arylester group, —CONH2, —CONH(C1-14 alkyl), —CONH(C6-14′aryl), —CON(C1-14 alky)2, —CON(C1-14 alkyl) (C6-14 aryl), —CON(C6-14 aryl)2, —C(O)H, a C1-14 alkoxy group, a C1-14 alkylthio group, a C6-14 aryloxy group, a C6-14 arylthio group, a C1-14 alkyl group, a 3-14 membered cycloheteroalkyl group, a C6-20 aryl group, or a 5-20 membered heteroaryl group;
• n is 0, 1 , 2, or 3;
• x is 0, 1, 2, 3, or 4;
• y is 1, 2, 3, or 4 if z is 0, and is 0, 1, 2, 3, or 4 if z is >0;
• and
• z is 1, 2, 3, or 4 if y is 0, and is 0, 1, 2, 3, or 4 if y is >0.