Formation of conjugated polymers for solid-state devices
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
H01L-051/00
C25B-003/00
G02F-001/15
H01L-051/05
H01L-051/42
H01L-051/50
출원번호
US-0511450
(2014-10-10)
등록번호
US-9680102
(2017-06-13)
발명자
/ 주소
Sotzing, Gregory Allen
Invernale, Michael A.
출원인 / 주소
UNIVERSITY OF CONNECTICUT
대리인 / 주소
Cantor Colburn LLP
인용정보
피인용 횟수 :
0인용 특허 :
22
초록▼
Disclosed herein is a facile process for the formation of conjugated polymers inside or outside assembled solid-state devices. One process generally involves applying a voltage to a device comprising at least two electrodes, a combination of an electrolyte composition and a electroactive monomer dis
Disclosed herein is a facile process for the formation of conjugated polymers inside or outside assembled solid-state devices. One process generally involves applying a voltage to a device comprising at least two electrodes, a combination of an electrolyte composition and a electroactive monomer disposed between the electrodes, and a potential source in electrical connection with the at least two electrodes; wherein the applying voltage polymerizes the electroactive monomer into a conjugated polymer. Also disclosed are electrochromic articles prepared from the process and solid-state devices comprising a composite of an electrolyte composition and a conjugated polymer.
대표청구항▼
1. A method of forming a solid-state device, comprising: providing a gel electrolyte precursor and an electroactive monomer disposed between at least two electrodes to form a device,applying a voltage to the device to polymerize the electroactive monomer in the presence of the gel electrolyte precur
1. A method of forming a solid-state device, comprising: providing a gel electrolyte precursor and an electroactive monomer disposed between at least two electrodes to form a device,applying a voltage to the device to polymerize the electroactive monomer in the presence of the gel electrolyte precursor to form a conjugated polymer, andcrosslinking the gel electrolyte precursor to form a crosslinked gel electrolyte composition to form a solid-state device comprising a composite comprising conjugated polymer and crosslinked gel electrolyte composition. 2. The method of claim 1, wherein the crosslinked gel electrolyte composition comprises a lithium, sodium, or potassium salt, or an ionic liquid. 3. The method of claim 1, wherein the device further comprises a reference electrode. 4. The method of claim 1, wherein the electroactive monomer is thiophene, substituted thiophene, carbazole, 3,4-ethylenedioxythiophene, thieno[3,4-b]thiophene, substituted thieno[3,4-b]thiophene, dithieno[3,4-b:3′,4′-d]thiophene, thieno[3,4-b]furan, substituted thieno[3,4-b]furan, bithiophene, substituted bithiophene, pyrrole, substituted pyrrole, acetylene, phenylene, substituted phenylene, naphthalene, substituted naphthalene, biphenyl and terphenyl and their substituted versions, phenylene vinylene (e.g., p-phenylene vinylene), substituted phenylene vinylene, aniline, substituted aniline, indole, substituted indole, or a combination thereof. 5. The method of claim 1, wherein the electroactive monomer is whereineach occurrence of Q1 is independently S, O, or Se;Q2 is S, O, or N—R2;each occurrence of Q3 is independently CH or N;Q4 is C(R1)2, S, O, or N—R2;each occurrence of Q5 is independently CH2, S, or O;each occurrence of R1 is independently hydrogen, C1-C12 alkyl, C1-C12 alkyl-OH, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, or —C1-C6 alkyl-O-aryl;R2 is hydrogen or C1-C6 alkyl;each occurrence of R3, R4, R5, and R6 independently is hydrogen; optionally substituted C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1-C10 alkyl-aryl; or hydroxyl;each occurrence of R7 is an electron withdrawing group;each occurrence of R8 is independently hydrogen, C1-C6 alkyl, or cyano;each occurrence of R9 is independently C1-C12 alkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, —C1-C6 alkyl-O-aryl, or N—R2;each occurrence of R10 is independently C1-C12 alkyl, C1-C12 haloalkyl, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, or —C1-C6 alkyl-O-aryl;E is O or C(R7)2; represents an aryl; is C2, C4, or C6 alkenylene, an aryl or heteroaryl; and g is 0, 1, 2, or 3. 6. The method of claim 1, wherein the combination of gel electrolyte precursor and an electroactive monomer further comprises a conducting oligomer, a conducting precursor polymer, a viologen, or a combination thereof. 7. The method of claim 1, further comprising patterning the device using a blocking material;direct patterning;lithography;individually addressable electrodes; ordirected polymerization by the selective application of voltage. 8. The method of claim 1, wherein an electrochemical atomic force microscope (AFM) tip is used as an external working electrode to supply the voltage for the applying. 9. A solid-state device, comprising: at least two electrodes; anda composite disposed between the at least two electrodes, the composite comprising a conjugated polymer and a crosslinked gel electrolyte composition;wherein the solid-state device is formed byproviding a gel electrolyte precursor and an electroactive monomer disposed between at least two electrodes to form a device,applying a voltage to the device to polymerize the electroactive monomer in the presence of the gel electrolyte precursor to form a conjugated polymer, andcrosslinking the gel electrolyte precursor to form a crosslinked gel electrolyte composition to form the solid-state device comprising a composite comprising conjugated polymer and crosslinked gel electrolyte composition, wherein the conjugated polymer is not formed as a discrete film. 10. The solid-state device of claim 9, wherein the crosslinked gel electrolyte composition comprises a lithium, sodium, or potassium salt, or an ionic liquid. 11. The solid-state device of claim 9, further comprising a layer disposed on the composite, the layer comprising a second electrolyte composition, ora second composite comprising the second electrolyte composition and a second conjugated polymer formed by in situ polymerization of a second electroactive monomer in a second combination comprising the second electrolyte composition and second electroactive monomer. 12. The solid-state device of claim 9, wherein the electroactive monomer is thiophene, substituted thiophene, carbazole, 3,4-ethylenedioxythiophene, thieno[3,4-b]thiophene, substituted thieno[3,4-b]thiophene, dithieno[3,4-b:3′,4′-d]thiophene, thieno[3,4-b]furan, substituted thieno[3,4-b]furan, bithiophene, substituted bithiophene, pyrrole, substituted pyrrole, acetylene, phenylene, substituted phenylene, naphthalene, substituted naphthalene, biphenyl and terphenyl and their substituted versions, phenylene vinylene (e.g., p-phenylene vinylene), substituted phenylene vinylene, aniline, substituted aniline, indole, substituted indole, or a combination thereof. 13. The solid-state device of claim 9, wherein the electroactive monomer is wherein each occurrence of Q1 is independently S, O, or Se;Q2 is S, O, or N—R2;each occurrence of Q3 is independently CH or N;Q4 is C(R1)2, S, O, or N—R2;each occurrence of Q5 is independently CH2, S, or O;each occurrence of R1 is independently hydrogen, C1-C12 alkyl, C1-C12 alkyl-OH, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, or —C1-C6 alkyl-O-aryl;R2 is hydrogen or C1-C6 alkyl;each occurrence of R3, R4, R5, and R6 independently is hydrogen; optionally substituted C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1-C10 alkyl-aryl; or hydroxyl;each occurrence of R7 is an electron withdrawing group;each occurrence of R8 is independently hydrogen, C1-C6 alkyl, or cyano;each occurrence of R9 is independently C1-C12 alkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C1-C12 haloalkoxy, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, —C1-C6 alkyl-O-aryl, or N—R2;each occurrence of R10 is independently C1-C12 alkyl, C1-C12 haloalkyl, aryl, —C1-C6 alkyl-O—C1-C6 alkyl, or —C1-C6 alkyl-O-aryl;E is O or C(R7)2; represents an aryl; is C2, C4, C6 alkenylene, an aryl or heteroaryl; and g is 0, 1, 2, or 3. 14. The solid-state device of claim 9, wherein the providing a gel electrolyte precursor and an electroactive monomer further comprises providing a conducting oligomer, a conducting precursor polymer, a viologen, or a combination thereof. 15. The solid-state device of claim 9, wherein the at least two electrodes are indium-doped tin oxide (ITO) coated substrates. 16. The solid-state device of claim 9, further comprising a reference electrode. 17. The solid-state device of claim 9, further comprising a potential source in electrical connection with the at least two electrodes. 18. The solid-state device of claim 9, wherein the device is an electrochromic device, an organic thin-film transistor, an organic light-emitting diode, or an organic photovoltaic cell. 19. A solid-state device prepared by the method of claim 1.
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