# US 8,569,501 B2 · Semiconductor materials and methods of preparation and use thereof

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- Number: US 8,569,501 B2
- Document ID: US8569501B2
- Status: Granted
- Kind: B2
- Application number: 12/994,596
- Filed: 2009-05-29
- Published: 2011-06-09
- Granted: 2013-10-29
- Earliest claimed: 2008-05-30
- Assignees: BASF SE; Polyera Corporation
- Applicants: Antonio Facchetti; Zhihua Chen; Florian Doetz; Marcel Kastler; Tobin J. Marks; He Yan; Yan Zheng
- Inventors: Antonio Facchetti; Zhihua Chen; Florian Doetz; Marcel Kastler; Tobin J. Marks; He Yan; Yan Zheng
- Web page: https://patentgrep.com/patent/US8569501B2

## CPC

- C07D 471/06: Peri-condensed systems
- C09B 3/78: Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
- C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C09B 57/08: Naphthalimide dyes; Phthalimide dyes
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Disclosed are new semiconductor materials prepared from dimeric perylene compounds. Such compounds can exhibit high n-type carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

## Claims

### Claim 1

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 selected from the group consisting of b) —(Ar2)n′—, c) —(Ar1)n—(Ar2)n′—(Ar1)n″—, and d) —(Ar2)n′—(Ar1)n—(Ar2)n″—,
wherein:
Ar1, at each occurrence, independently is a 5- or 6-membered aryl or heteroaryl group, each optionally substituted with 1-4 Ri groups;
Ar2, at each occurrence, independently is selected from an optionally substituted polycyclic 8-22 membered aryl or heteroaryl group comprising at least one phenyl, thienyl, or thiazolyl group fused to a moiety selected from the group consisting of:
and
n, n′, and n″ independently are 1, 2, 3, 4, 5, or 6.

### Claim 2

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:

### Claim 3

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.

### Claim 4

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.

### Claim 5

A compound of the formula:
wherein Rb, at each occurrence, is a linear or branched C4-20 alkyl group.

### Claim 6 (depends on 1)

The compound of claim 1, wherein π-1, at each occurrence, is selected from the group consisting of:
wherein each Z is O or NRb.

### Claim 7 (depends on 1)

A composition comprising one or more compounds of claim 1, dissolved or dispersed in a liquid medium.

### Claim 8 (depends on 1)

An electronic, optical, or optoelectronic device comprising a thin film semiconductor comprising one or more compounds of claim 1.

### Claim 9 (depends on 7)

A method of making an electronic, optical, or optoelectronic device, the device comprising a thin film conductor, the method comprising depositing a composition of claim 7 onto a substrate, wherein depositing the composition comprises at least one selected from the group consisting of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, and spraying.

### Claim 10 (depends on 2)

The compound of claim 2, wherein π-1, at each occurrence, is selected from the group consisting of:
wherein each Z is O or NRb.

### Claim 11 (depends on 2)

A composition comprising one or more compounds of claim 2, dissolved or dispersed in a liquid medium.

### Claim 12 (depends on 2)

An electronic, optical, or optoelectronic device comprising a thin film semiconductor comprising one or more compounds of claim 2.

### Claim 13 (depends on 11)

A method of making an electronic, optical, or optoelectronic device, the device comprising a thin film conductor, the method comprising depositing a composition of claim 11 onto a substrate, wherein depositing the composition comprises at least one selected from the group consisting of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, and spraying.

### Claim 14 (depends on 3)

The compound of claim 3, wherein π-1, at each occurrence, is selected from the group consisting of:
wherein each Z is O or NRb.

### Claim 15 (depends on 3)

A composition comprising one or more compounds of claim 3, dissolved or dispersed in a liquid medium.

### Claim 16 (depends on 3)

An electronic, optical, or optoelectronic device comprising a thin film semiconductor comprising one or more compounds of claim 3.

### Claim 17 (depends on 15)

A method of making an electronic, optical, or optoelectronic device, the device comprising a thin film conductor, the method comprising depositing a composition of claim 15 onto a substrate, wherein depositing the composition comprises at least one selected from the group consisting of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, and spraying.

### Claim 18 (depends on 4)

The compound of claim 4, wherein π-1, at each occurrence, is selected from the group consisting of:
wherein each Z is O or NRb.

### Claim 19 (depends on 4)

A composition comprising one or more compounds of claim 4, dissolved or dispersed in a liquid medium.

### Claim 20 (depends on 4)

An electronic, optical, or optoelectronic device comprising a thin film semiconductor comprising one or more compounds of claim 4.

### Claim 21 (depends on 19)

A method of making an electronic, optical, or optoelectronic device, the device comprising a thin film conductor, the method comprising depositing a composition of claim 19 onto a substrate, wherein depositing the composition comprises at least one selected from the group consisting of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, and spraying.

### Claim 22 (depends on 5)

A composition comprising one or more compounds of claim 5, dissolved or dispersed in a liquid medium.

### Claim 23 (depends on 5)

An electronic, optical, or optoelectronic device comprising a thin film semiconductor comprising one or more compounds of claim 5.

### Claim 24 (depends on 22)

A method of making an electronic, optical, or optoelectronic device, the device comprising a thin film conductor, the method comprising depositing a composition of claim 22 onto a substrate, wherein depositing the composition comprises at least one selected from the group consisting of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, and spraying.