IP Library › Granted Patent US 8,569,501

Granted Patent B2

US 8,569,501 · App. 12/994,596 · Granted Oct 29, 2013

Semiconductor materials and methods of preparation and use thereof

Inventors: Antonio Facchetti (Chicago, IL); Zhihua Chen (Skokie, IL); Florian Doetz (Singapore, SG); Marcel Kastler (Basel, CH); Tobin J. Marks (Evanston, IL); He Yan (Skokie, IL); Yan Zheng (Skokie, IL)

Assignees: BASF SE; Polyera Corporation

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Quick Facts

Patent No.: US 8,569,501
App. No.: 12/994,596
Granted: Oct 29, 2013
Kind: B2

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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 (104)

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 R a groups;

Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NR b , d) C(O), and e) CR c R d ;

R a , at each occurrence, is a) halogen, b) —CN, c) —NO 2 , d) —OR f , e) —SR f , f) —NR g R h , g) —N(O)R g R h , h) —S(O) m R g , i) —S(O) m OR g , j) —S(O) m NR g R h , k) —C(O)R g , l) —C(O)OR f , m) —C(O)NR g R h , n) —C(S)NR g R h , o) —SiH 3 , p) —SiH(C 1-20 alkyl) 2 , q) —SiH 2 (C 1-20 alkyl), r) —Si(C 1-20 alkyl) 3 , s) a C 1-20 alkyl group, t) a C 2-20 alkenyl group, u) a C 2-20 alkynyl group, v) a C 1-20 haloalkyl group, w) a —Y—C 3-14 cycloalkyl group, x) a —Y—C 6-14 aryl group, y) a —Y-3-14 membered cycloheteroalkyl group, or z) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 R i groups;

R b , at each occurrence, is a) H, b) —(CH 2 CH 2 O) q H, c) —(CH 2 CH 2 O) q —CH 3 , d) —C(O)OR f , e) —C(O)R g , f) —C(O)NR g R h , g) —C(S)OR f , h) —C(S)R g , i) —C(S)NR g R h , j) —S(O) m R g , k) —S(O) m OR g , l) a C 1-20 alkyl group, m) a C 2-20 alkenyl group, n) a C 2-20 alkynyl group, o) a C 1-20 alkoxy group, p) a —Y—C 3-14 cycloalkyl group, q) a —Y—C 6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, or s) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 1-20 alkoxy group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 R i groups;

R c and R d , at each occurrence, independently are a) H, b) halogen, c) —(CH 2 CH 2 O) q H, d —(CH 2 CH 2 O) q —CH 3 , e) a C 1-20 alkoxy group, f) a C 1-20 alkyl group, g) a C 2-20 alkenyl group, h) a C 2-20 alkynyl group, i) a —Y—C 3-14 cycloalkyl group, j) a —Y—C 6-14 aryl group, k) a —Y-3-14 membered cycloheteroalkyl group, or l) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 R i groups;

R f , at each occurrence, is a) H, b) —C(O)R g , c) —C(O)NR g R h , d) —C(S)R g , e) —C(S)NR g R h , f) a C 1-20 alkyl group, g) a C 2-20 alkenyl group, h) a C 2-20 alkynyl group, i) a C 3-14 cycloalkyl group, j) a C 6-14 aryl group, k) a 3-14 membered cycloheteroalkyl group, or l) a 5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 R i groups;

R g and R h , at each occurrence, independently are a) H, b) —OH, c) —SH, d) —S(O) 2 OH, e) —C(O)OH, f) —C(O)NH 2 , g) —C(S)NH 2 , h) —OC 1-10 alkyl, i) —C(O)—C 1-20 alkyl, j) —C(O)—OC 1-20 alkyl, k) —C(S)N(C 1-20 alkyl) 2 , l) —C(S)NH—C 1-20 alkyl, m) —C(O)NH—C 1-20 alkyl, n) —C(O)N(C 1-20 alkyl) 2 , o) —S(O) m —C 1-20 alkyl, p) —S(O) m —OC 1-20 alkyl, q) a C 1-20 alkyl group, r) a C 2-20 alkenyl group, s) a C 2-20 alkynyl group, t) a C 1-20 alkoxy group, u) a C 3-14 cycloalkyl group, v) a C 6-14 aryl group, w) a 3-14 membered cycloheteroalkyl group, or x) a 5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl groups, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4 R i groups;

R i , at each occurrence, is a) halogen, b) —CN, c) —NO 2 , d) oxo, e) —OH, f) —NH 2 , g) —NH(C 1-20 alkyl), h) —N(C 1-20 alkyl) 2 , i) —N(C 1-20 alkyl)-C 6-14 aryl, j) —N(C 6-14 aryl) 2 , k) —S(O) m H, l) —S(O) m —C 1-20 alkyl, m) —S(O) 2 OH, n) —S(O) m —OC 1-20 alkyl, o) —S(O) m —OC 6-14 aryl, p) —CHO, q) —C(O)—C 1-20 alkyl, r) —C(O)-C 6-14 aryl, s) —C(O)OH, t) —C(O)—OC 1-20 alkyl, u) —C(O)—CO 6-14 aryl, v) —C(O)NH 2 , w) —C(O)NH—C 1-20 alkyl, x) —C(O)N(C 1-20 alkyl) 2 , y) —C(O)NH—C 6-14 aryl, z) —C(O)N(C 1-20 alkyl)-C 6-14 aryl, aa) —C(O)N(C 6-14 aryl) 2 , ab) —C(S)NH 2 , ac) —(C(S)NH—C 1-20 alkyl, ad) —C(S)N(C 1-20 alkyl) 2 , ae) —C(S)N(C 6-14 aryl) 2 , af) —C(S)N(C 1-20 alkyl)-C 6-14 aryl, ag) —C(S)NH—C 6-14 aryl, ah) —S(O) m NH 2 , ai) —S(O) m NH(C 1-20 alkyl), aj) —S(O m N(C 1-20 alkyl) 2 , ak) —S(O) m NH(C 6-14 aryl), al) —S(O) m N(C 1-20 alkyl)-C 6-14 aryl, am) —S(O) m N(C 6-14 aryl) 2 , an) —SiH 3 , ao) —SiH(C 1-20 alkyl) 2 , ap) —SiH 2 (C 1-20 alkyl), ar) —Si(C 1-20 alkyl) 3 , as) a C 1-20 alkoxy group, at) a C 2-20 alkenyl group, au) a C 2-20 alkynyl group, av) a C 1-20 alkoxy group, aw) a C 1-20 alkylthio group, ax) a C 1-20 haloalkyl group, ay) a C 3-14 cycloalkyl group, az) a C 6-14 aryl group, ba) a 3-14 membered cycloheteroalkyl group, or bb) a 5-14 membered heteroaryl group;

Y, at each occurrence, is a) a divalent C 1-20 alkyl group, b) a divalent C 1-20 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) —(Ar 2 ) n′ —, c) —(Ar 1 ) n —(Ar 2 ) n′ —(Ar 1 ) n″ —, and d) —(Ar 2 ) n′ —(Ar 1 ) n —(Ar 2 ) n″ —,

wherein:

Ar 1 , at each occurrence, independently is a 5- or 6-membered aryl or heteroaryl group, each optionally substituted with 1-4 R i groups;

Ar 2 , 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.

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 R a groups;

Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NR b , d) C(O), and e) CR c R d ;

Y, at each occurrence, is a) a divalent C 1-20 alkyl group, b) a divalent C 1-20 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 —(Ar 1 ) n — and is selected from the group consisting of:

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 R a groups;

Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NR b , d) C(O), and e) CR c R d ;

Y, at each occurrence, is a) a divalent C 1-20 alkyl group, b) a divalent C 1-20 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 —(Ar 2 )—, wherein Ar 2 is selected from the group consisting of:

wherein R 2 , at each occurrence, independently is H or R i .

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 R a groups;

Z, at each occurrence, is selected from the group consisting of a) O, b) S, c) NR b , d) C(O), and e) CR c R d ;

R i , at each occurrence, is a) halogen, b) —CN, c) —NO 2 , d) oxo, e) —OH, f) —NH 2 , g) —NH(C 1-20 alkyl), h) —N(C 1-20 alkyl) 2 , i) —N(C 1-20 alkyl)-C 6-14 aryl, j) —N(C 6-14 aryl) 2 , k) —S(O) m H, l) —S(O) m —C 1-20 alkyl, m) —S(O) 2 OH, n) —S(O) m —OC 1-20 alkyl, o) —S(O) m —OC 6-14 aryl, p) —CHO, q) —C(O)—C 1-20 alkyl, r) —C(O)-C 6-14 aryl, s) —C(O)OH, t) —C(O)—OC 1-20 alkyl, u) —C(O)—OC 6-14 aryl, v) —C(O)NH 2 , w) —C(O)NH—C 1-20 alkyl, x) —C(O)N(C 1-20 alkyl) 2 , y) —C(O)NH—C 6-14 aryl, z) —C(O)N(C 1-20 alkyl)-C 6-14 aryl, aa) —C(O)N(C 6-14 aryl) 2 , ab) —C(S)NH 2 , ac) —(C(S)NH—C 1-20 alkyl, ad) —C(S)N(C 1-20 alkyl) 2 , ae) —C(S)N(C 6-14 aryl) 2 , af) —C(S)N(C 1-20 alkyl)-C 6-14 aryl, ag) —C(S)NH—C 6-14 aryl, ah) —S(O) m NH 2 , ai) —S(O) m NH(C 1-20 alkyl), aj) —S(O m N(C 1-20 alkyl) 2 , ak) —S(O) m NH(C 6-14 aryl), al) —S(O) m N(C 1-20 alkyl)-C 6-14 aryl, am) —S(O) m N(C 6-14 aryl) 2 , an) —SiH 3 , ao) —SiH(C 1-20 alkyl) 2 , ap) —SiH 2 (C 1-20 alkyl), ar) —Si(C 1-20 alkyl) 3 , as) a C 1-20 alkoxy group, at) a C 2-20 alkenyl group, au) a C 2-20 alkynyl group, av) a C 1-20 alkoxy group, aw) a C 1-20 alkylthio group, ax) a C 1-20 haloalkyl group, ay) a C 3-14 cycloalkyl group, az) a C 6-14 aryl group, ba) a 3-14 membered cycloheteroalkyl group, or bb) a 5-14 membered heteroaryl group;

Y, at each occurrence, is a) a divalent C 1-20 alkyl group, b) a divalent C 1-20 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.

5. A compound of the formula:

wherein R b , at each occurrence, is a linear or branched C 4-20 alkyl group.

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

wherein each Z is O or NR b .

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

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

9. 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.

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

wherein each Z is O or NR b .

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

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

13. 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.

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

wherein each Z is O or NR b .

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

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

17. 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.

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

wherein each Z is O or NR b .

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

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

21. 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.

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

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

24. 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.

Assignments (9)

ASSET PURCHASE AGREEMENT Recorded Dec 13, 2025

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