Semiconductor materials and methods of preparation and use thereof

A compound having Formula I:

• Q-L-Q′ I,
• wherein:
• Q and Q′ independently are:
• and
• wherein:
• π-1 is a perylene moiety optionally substituted with 1-8 Ra groups;
• Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NRb, d) C(O), and e) CRcRd;
• Ra, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) —ORf, e) —SRf, f) —NRgRh, g) —N(O)RgRh, h) —S(O)mRg, i) —S(O)mORg, j) —S(O)mNRgRh, k) —C(O)Rg, l) —C(O)ORf, m) —C(O)NRgRh, n) —C(S)NRgRh, o) —SiH3, p) —SiH(C1-20alkyl)2, q) —SiH2(C1-20alkyl), r) —Si(C1-20alkyl)3, s) a C1-20alkyl group, t) a C2-20alkenyl group, u) a C2-20alkynyl group, v) a C1-20haloalkyl group, w) a —Y—C3-14cycloalkyl group, x) a —Y—C6-14aryl group, y) a —Y-3-14 membered cycloheteroalkyl group, or z) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rb, at each occurrence, is a) H, b) —(CH2CH2O)qH, c) —(CH2CH2O)q—CH3, d) —C(O)ORf, e) —C(O)Rg, f) —C(O)NRgRh, g) —C(S)ORf, h) —C(S)Rg, i) —C(S)NRgRh, j) —S(O)mRg, k) —S(O)mORg, l) a C1-20alkyl group, m) a C2-20alkenyl group, n) a C2-20 alkynyl group, o) a C1-20alkoxy group, p) a —Y—C3-14cycloalkyl group, q) a —Y—C6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, or s) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C1-20alkoxy group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rc and Rd, at each occurrence, independently are a) H, b) halogen, c) —(CH2CH2O)qH, d —(CH2CH2O)q—CH3, e) a C1-20alkoxy group, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a —Y—C3-14cycloalkyl group, j) a —Y—C6-14aryl group, k) a —Y-3-14 membered cycloheteroalkyl group, or l) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rf, at each occurrence, is a) H, b) —C(O)Rg, c) —C(O)NRgRh, d) —C(S)Rg, e) —C(S)NRgRh, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a C3-14cycloalkyl group, j) a C6-14aryl group, k) a 3-14 membered cycloheteroalkyl group, or l) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rg and Rh, at each occurrence, independently are a) H, b) —OH, c) —SH, d) —S(O)2OH, e) —C(O)OH, f) —C(O)NH2, g) —C(S)NH2, h) —OC1-10alkyl, i) —C(O)—C1-20 alkyl, j) —C(O)—OC1-20alkyl, k) —C(S)N(C1-20alkyl)2, l) —C(S)NH—C1-20alkyl, m) —C(O)NH—C1-20alkyl, n) —C(O)N(C1-20alkyl)2, o) —S(O)m—C1-20alkyl, p) —S(O)m—OC1-20 alkyl, q) a C1-20alkyl group, r) a C2-20alkenyl group, s) a C2-20alkynyl group, t) a C1-20 alkoxy group, u) a C3-14cycloalkyl group, v) a C6-14aryl group, w) a 3-14 membered cycloheteroalkyl group, or x) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl groups, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14 cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Ri, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) —NH2, g) —NH(C1-20alkyl), h) —N(C1-20alkyl)2, i) —N(C1-20alkyl)-C6-14aryl, j) —N(C6-14aryl)2, k) —S(O)mH, l) —S(O)m—C1-20alkyl, m) —S(O)2OH, n) —S(O)m—OC1-20alkyl, o) —S(O)m—OC6-14aryl, p) —CHO, q) —C(O)—C1-20alkyl, r) —C(O)-C6-14aryl, s) —C(O)OH, t) —C(O)—OC1-20alkyl, u) —C(O)—CO6-14aryl, v) —C(O)NH2, w) —C(O)NH—C1-20alkyl, x) —C(O)N(C1-20alkyl)2, y) —C(O)NH—C6-14aryl, z) —C(O)N(C1-20alkyl)-C6-14aryl, aa) —C(O)N(C6-14aryl)2, ab) —C(S)NH2, ac) —(C(S)NH—C1-20alkyl, ad) —C(S)N(C1-20alkyl)2, ae) —C(S)N(C6-14aryl)2, af) —C(S)N(C1-20alkyl)-C6-14aryl, ag) —C(S)NH—C6-14 aryl, ah) —S(O)mNH2, ai) —S(O)mNH(C1-20alkyl), aj) —S(OmN(C1-20alkyl)2, ak) —S(O)mNH(C6-14aryl), al) —S(O)mN(C1-20alkyl)-C6-14aryl, am) —S(O)mN(C6-14aryl)2, an) —SiH3, ao) —SiH(C1-20alkyl)2, ap) —SiH2(C1-20alkyl), ar) —Si(C1-20alkyl)3, as) a C1-20alkoxy group, at) a C2-20alkenyl group, au) a C2-20alkynyl group, av) a C1-20alkoxy group, aw) a C1-20alkylthio group, ax) a C1-20haloalkyl group, ay) a C3-14cycloalkyl group, az) a C6-14aryl group, ba) a 3-14 membered cycloheteroalkyl group, or bb) a 5-14 membered heteroaryl group;
• Y, at each occurrence, is a) a divalent C1-20alkyl group, b) a divalent C1-20 haloalkyl group, or c) a covalent bond;
• m, at each occurrence, is 0, 1, or 2 and
• q, at each occurrence, is an integer in the range of 1 to 20,
• L is —(Ar1)n— and is selected from the group consisting of:

A compound having Formula I:

• Q-L-Q′ I,
• wherein:
• Q and Q′ independently are:
• and
• wherein:
• π-1 is a perylene moiety optionally substituted with 1-8 Ra groups;
• Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NRb, d) C(O), and e) CRcRd;
• Ra, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) —ORf, e) —SRf, f) —NRgRh, g) —N(O)RgRh, h) —S(O)mRg, i) —S(O)mORg, j) —S(O)mNRgRh, k) —C(O)Rg, l) —C(O)ORf, m) —C(O)NRgRh, n) —C(S)NRgRh, o) —SiH3, p) —SiH(C1-20alkyl)2, q) —SiH2(C1-20alkyl), r) —Si(C1-20alkyl)3, s) a C1-20alkyl group, t) a C2-20alkenyl group, u) a C2-20alkynyl group, v) a C1-20haloalkyl group, w) a —Y—C3-14cycloalkyl group, x) a —Y—C6-14aryl group, y) a —Y-3-14 membered cycloheteroalkyl group, or z) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rb, at each occurrence, is a) H, b) —(CH2CH2O)qH, c) —(CH2CH2O)q—CH3, d) —C(O)ORf, e) —C(O)Rg, f) —C(O)NRgRh, g) —C(S)ORf, h) —C(S)Rg, i) —C(S)NRgRh, j) —S(O)mRg, k) —S(O)mORg, l) a C1-20alkyl group, m) a C2-20alkenyl group, n) a C2-20 alkynyl group, o) a C1-20alkoxy group, p) a —Y—C3-14cycloalkyl group, q) a —Y—C6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, or s) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C1-20alkoxy group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rc and Rd, at each occurrence, independently are a) H, b) halogen, c) —(CH2CH2O)qH, d —(CH2CH2O)q—CH3, e) a C1-20alkoxy group, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a —Y—C3-14cycloalkyl group, j) a —Y—C6-14aryl group, k) a —Y-3-14 membered cycloheteroalkyl group, or l) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rf, at each occurrence, is a) H, b) —C(O)Rg, c) —C(O)NRgRh, d) —C(S)Rg, e) —C(S)NRgRh, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a C3-14cycloalkyl group, j) a C6-14aryl group, k) a 3-14 membered cycloheteroalkyl group, or l) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rg and Rh, at each occurrence, independently are a) H, b) —OH, c) —SH, d) —S(O)2OH, e) —C(O)OH, f) —C(O)NH2, g) —C(S)NH2, h) —OC1-10alkyl, i) —C(O)—C1-20 alkyl, j) —C(O)—OC1-20alkyl, k) —C(S)N(C1-20alkyl)2, l) —C(S)NH—C1-20alkyl, m) —C(O)NH—C1-20alkyl, n) —C(O)N(C1-20alkyl)2, o) —S(O)m—C1-20alkyl, p) —S(O)m—OC1-20 alkyl, q) a C1-20alkyl group, r) a C2-20alkenyl group, s) a C2-20alkynyl group, t) a C1-20 alkoxy group, u) a C3-14cycloalkyl group, v) a C6-14aryl group, w) a 3-14 membered cycloheteroalkyl group, or x) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl groups, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14 cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Ri, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) —NH2, g) —NH(C1-20alkyl), h) —N(C1-20alkyl)2, i) —N(C1-20alkyl)-C6-14aryl, j) —N(C6-14aryl)2, k) —S(O)mH, l) —S(O)m—C1-20alkyl, m) —S(O)2OH, n) —S(O)m—OC1-20alkyl, o) —S(O)m—OC6-14aryl, p) —CHO, q) —C(O)—C1-20alkyl, r) —C(O)-C6-14aryl, s) —C(O)OH, t) —C(O)—OC1-20alkyl, u) —C(O)—CO6-14aryl, v) —C(O)NH2, w) —C(O)NH—C1-20alkyl, x) —C(O)N(C1-20alkyl)2, y) —C(O)NH—C6-14aryl, z) —C(O)N(C1-20alkyl)-C6-14aryl, aa) —C(O)N(C6-14aryl)2, ab) —C(S)NH2, ac) —(C(S)NH—C1-20alkyl, ad) —C(S)N(C1-20alkyl)2, ae) —C(S)N(C6-14aryl)2, af) —C(S)N(C1-20alkyl)-C6-14aryl, ag) —C(S)NH—C6-14 aryl, ah) —S(O)mNH2, ai) —S(O)mNH(C1-20alkyl), aj) —S(OmN(C1-20alkyl)2, ak) —S(O)mNH(C6-14aryl), al) —S(O)mN(C1-20alkyl)-C6-14aryl, am) —S(O)mN(C6-14aryl)2, an) —SiH3, ao) —SiH(C1-20alkyl)2, ap) —SiH2(C1-20alkyl), ar) —Si(C1-20alkyl)3, as) a C1-20alkoxy group, at) a C2-20alkenyl group, au) a C2-20alkynyl group, av) a C1-20alkoxy group, aw) a C1-20alkylthio group, ax) a C1-20haloalkyl group, ay) a C3-14cycloalkyl group, az) a C6-14aryl group, ba) a 3-14 membered cycloheteroalkyl group, or bb) a 5-14 membered heteroaryl group;
• Y, at each occurrence, is a) a divalent C1-20alkyl group, b) a divalent C1-20 haloalkyl group, or c) a covalent bond;
• m, at each occurrence, is 0, 1, or 2 and
• q, at each occurrence, is an integer in the range of 1 to 20,
• L is —(Ar2)—, wherein Ar2 is selected from the group consisting of:
• wherein R2, at each occurrence, independently is H or Ri.

A compound having Formula I:

• Q-L-Q′ I,
• wherein:
• Q and Q′ independently are:
• and
• wherein:
• π-1 is a perylene moiety optionally substituted with 1-8 Ra groups;
• Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NRb, d) C(O), and e) CRcRd;
• Ra, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) —ORf, e) —SRf, f) —NRgRh, g) —N(O)RgRh, h) —S(O)mRg, i) —S(O)mORg, j) —S(O)mNRgRh, k) —C(O)Rg, l) —C(O)ORf, m) —C(O)NRgRh, n) —C(S)NRgRh, o) —SiH3, p) —SiH(C1-20alkyl)2, q) —SiH2(C1-20alkyl), r) —Si(C1-20alkyl)3, s) a C1-20alkyl group, t) a C2-20alkenyl group, u) a C2-20alkynyl group, v) a C1-20haloalkyl group, w) a —Y—C3-14cycloalkyl group, x) a —Y—C6-14aryl group, y) a —Y-3-14 membered cycloheteroalkyl group, or z) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rb, at each occurrence, is a) H, b) —(CH2CH2O)qH, c) —(CH2CH2O)q—CH3, d) —C(O)ORf, e) —C(O)Rg, f) —C(O)NRgRh, g) —C(S)ORf, h) —C(S)Rg, i) —C(S)NRgRh, j) —S(O)mRg, k) —S(O)mORg, l) a C1-20alkyl group, m) a C2-20alkenyl group, n) a C2-20 alkynyl group, o) a C1-20alkoxy group, p) a —Y—C3-14cycloalkyl group, q) a —Y—C6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, or s) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C1-20alkoxy group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rc and Rd, at each occurrence, independently are a) H, b) halogen, c) —(CH2CH2O)qH, d —(CH2CH2O)q—CH3, e) a C1-20alkoxy group, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a —Y—C3-14cycloalkyl group, j) a —Y—C6-14aryl group, k) a —Y-3-14 membered cycloheteroalkyl group, or l) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rf, at each occurrence, is a) H, b) —C(O)Rg, c) —C(O)NRgRh, d) —C(S)Rg, e) —C(S)NRgRh, f) a C1-20alkyl group, g) a C2-20alkenyl group, h) a C2-20alkynyl group, i) a C3-14cycloalkyl group, j) a C6-14aryl group, k) a 3-14 membered cycloheteroalkyl group, or l) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl group, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Rg and Rh, at each occurrence, independently are a) H, b) —OH, c) —SH, d) —S(O)2OH, e) —C(O)OH, f) —C(O)NH2, g) —C(S)NH2, h) —OC1-10alkyl, i) —C(O)—C1-20 alkyl, j) —C(O)—OC1-20alkyl, k) —C(S)N(C1-20alkyl)2, l) —C(S)NH—C1-20alkyl, m) —C(O)NH—C1-20alkyl, n) —C(O)N(C1-20alkyl)2, o) —S(O)m—C1-20alkyl, p) —S(O)m—OC1-20 alkyl, q) a C1-20alkyl group, r) a C2-20alkenyl group, s) a C2-20alkynyl group, t) a C1-20 alkoxy group, u) a C3-14cycloalkyl group, v) a C6-14aryl group, w) a 3-14 membered cycloheteroalkyl group, or x) a 5-14 membered heteroaryl group, wherein each of the C1-20alkyl groups, the C2-20alkenyl group, the C2-20alkynyl group, the C3-14 cycloalkyl group, the C6-14aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 Ri groups;
• Ri, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) —NH2, g) —NH(C1-20alkyl), h) —N(C1-20alkyl)2, i) —N(C1-20alkyl)-C6-14aryl, j) —N(C6-14aryl)2, k) —S(O)mH, l) —S(O)m—C1-20alkyl, m) —S(O)2OH, n) —S(O)m—OC1-20alkyl, o) —S(O)m—OC6-14aryl, p) —CHO, q) —C(O)—C1-20alkyl, r) —C(O)-C6-14aryl, s) —C(O)OH, t) —C(O)—OC1-20alkyl, u) —C(O)—OC6-14aryl, v) —C(O)NH2, w) —C(O)NH—C1-20alkyl, x) —C(O)N(C1-20alkyl)2, y) —C(O)NH—C6-14aryl, z) —C(O)N(C1-20alkyl)-C6-14aryl, aa) —C(O)N(C6-14aryl)2, ab) —C(S)NH2, ac) —(C(S)NH—C1-20alkyl, ad) —C(S)N(C1-20alkyl)2, ae) —C(S)N(C6-14aryl)2, af) —C(S)N(C1-20alkyl)-C6-14aryl, ag) —C(S)NH—C6-14 aryl, ah) —S(O)mNH2, ai) —S(O)mNH(C1-20alkyl), aj) —S(OmN(C1-20alkyl)2, ak) —S(O)mNH(C6-14aryl), al) —S(O)mN(C1-20alkyl)-C6-14aryl, am) —S(O)mN(C6-14aryl)2, an) —SiH3, ao) —SiH(C1-20alkyl)2, ap) —SiH2(C1-20alkyl), ar) —Si(C1-20alkyl)3, as) a C1-20alkoxy group, at) a C2-20alkenyl group, au) a C2-20alkynyl group, av) a C1-20alkoxy group, aw) a C1-20alkylthio group, ax) a C1-20haloalkyl group, ay) a C3-14cycloalkyl group, az) a C6-14aryl group, ba) a 3-14 membered cycloheteroalkyl group, or bb) a 5-14 membered heteroaryl group;
• Y, at each occurrence, is a) a divalent C1-20alkyl group, b) a divalent C1-20 haloalkyl group, or c) a covalent bond;
• m, at each occurrence, is 0, 1, or 2 and
• q, at each occurrence, is an integer in the range of 1 to 20,
• L is
• wherein each of n and n″ is 1 or 2.