RU2016101074A - Способ получения электрохромных полимеров на основе диоксигетероциклов - Google Patents
Способ получения электрохромных полимеров на основе диоксигетероциклов Download PDFInfo
- Publication number
- RU2016101074A RU2016101074A RU2016101074A RU2016101074A RU2016101074A RU 2016101074 A RU2016101074 A RU 2016101074A RU 2016101074 A RU2016101074 A RU 2016101074A RU 2016101074 A RU2016101074 A RU 2016101074A RU 2016101074 A RU2016101074 A RU 2016101074A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- aryl
- arylalkyl
- amino
- thirophenol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 239000000178 monomer Substances 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 125000003368 amide group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 238000006116 polymerization reaction Methods 0.000 claims 5
- -1 thirophene Chemical group 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 229920000728 polyester Polymers 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000005027 hydroxyaryl group Chemical group 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 229910052711 selenium Inorganic materials 0.000 claims 3
- 229910052714 tellurium Inorganic materials 0.000 claims 3
- MLCPSWPIYHDOKG-BUHFOSPRSA-N (3e)-3-(2-oxo-1h-indol-3-ylidene)-1h-indol-2-one Chemical compound O=C\1NC2=CC=CC=C2C/1=C1/C2=CC=CC=C2NC1=O MLCPSWPIYHDOKG-BUHFOSPRSA-N 0.000 claims 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 2
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims 2
- FILUFGAZMJGNEN-UHFFFAOYSA-N pent-1-en-3-yne Chemical group CC#CC=C FILUFGAZMJGNEN-UHFFFAOYSA-N 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 2
- 125000002577 pseudohalo group Chemical group 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical group BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 claims 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 claims 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- HBDIJEQBNZWIJR-UHFFFAOYSA-N 2-(3h-cyclopenta[c]dithiol-4-ylidene)propanedinitrile Chemical compound C1SSC2=C1C(=C(C#N)C#N)C=C2 HBDIJEQBNZWIJR-UHFFFAOYSA-N 0.000 claims 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims 1
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical compound C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 claims 1
- YYKZOERQHDYCMV-UHFFFAOYSA-N 3,3-bis(2-ethylhexoxymethyl)-2,4-dihydrothieno[3,4-b][1,4]dioxepine Chemical group O1CC(COCC(CC)CCCC)(COCC(CC)CCCC)COC2=CSC=C21 YYKZOERQHDYCMV-UHFFFAOYSA-N 0.000 claims 1
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 claims 1
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- FRSCCZDSSYMDKY-UHFFFAOYSA-N 6,8-dibromo-3,3-bis(2-ethylhexoxymethyl)-2,4-dihydrothieno[3,4-b][1,4]dioxepine Chemical compound O1CC(COCC(CC)CCCC)(COCC(CC)CCCC)COC2=C(Br)SC(Br)=C21 FRSCCZDSSYMDKY-UHFFFAOYSA-N 0.000 claims 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 claims 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims 1
- HRQNQGYOKJAUID-UHFFFAOYSA-N CCCCC(CC)COCC1(COCC(CC)CCCC)COc2csc(Br)c2OC1 Chemical compound CCCCC(CC)COCC1(COCC(CC)CCCC)COc2csc(Br)c2OC1 HRQNQGYOKJAUID-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- PFDOOVOOEKSMNW-UHFFFAOYSA-N [1,2,5]oxadiazolo[3,4-c]pyridine Chemical compound C1=NC=CC2=NON=C21 PFDOOVOOEKSMNW-UHFFFAOYSA-N 0.000 claims 1
- POQXSXLBPPFJFO-UHFFFAOYSA-N [1,3]thiazolo[5,4-d][1,3]thiazole Chemical compound S1C=NC2=C1N=CS2 POQXSXLBPPFJFO-UHFFFAOYSA-N 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000006323 alkenyl amino group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000006319 alkynyl amino group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229920000547 conjugated polymer Polymers 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- ZEHZNAXXOOYTJM-UHFFFAOYSA-N dicyanoacetylene Chemical group N#CC#CC#N ZEHZNAXXOOYTJM-UHFFFAOYSA-N 0.000 claims 1
- VGWBXRXNERKBSJ-UHFFFAOYSA-N dithieno[2,3-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC=C1 VGWBXRXNERKBSJ-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940097275 indigo Drugs 0.000 claims 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 229920002601 oligoester Polymers 0.000 claims 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- CVSGFMWKZVZOJD-UHFFFAOYSA-N pyrazino[2,3-f]quinoxaline Chemical compound C1=CN=C2C3=NC=CN=C3C=CC2=N1 CVSGFMWKZVZOJD-UHFFFAOYSA-N 0.000 claims 1
- TYLGVQVJCVFREB-UHFFFAOYSA-N pyrido[3,4-b]pyrazine Chemical compound C1=NC=CC2=NC=CN=C21 TYLGVQVJCVFREB-UHFFFAOYSA-N 0.000 claims 1
- QKWILNTYPDJSME-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=NC(=O)C2=C1C(=O)N=C2 QKWILNTYPDJSME-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- DTDZVQXOCHUQLZ-UHFFFAOYSA-N thiadiazolo[5,4-f]quinoxaline Chemical compound C1=CC2=NC=CN=C2C2=C1N=NS2 DTDZVQXOCHUQLZ-UHFFFAOYSA-N 0.000 claims 1
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 claims 1
- YCIFPAMAAWDQJS-UHFFFAOYSA-N thieno[2,3-d]thiadiazole Chemical compound S1N=NC2=C1C=CS2 YCIFPAMAAWDQJS-UHFFFAOYSA-N 0.000 claims 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/54—Physical properties electrochromatic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (23)
1. Способ получения сопряженного полимера, включающий
подачу, по меньшей мере, одного первого мономера, включающего 3,4-диокситиофен, 3,4-диоксиселенофен, 3,4-диоксителлурофен, 3,4-диоксифуран или 3,4-диоксипиррол;
необязательно подачу, по меньшей мере, одного второго мономера, содержащего сопряженное звено;
подачу катализатора, содержащего Pd или Ni;
подачу апротонного растворителя;
подачу карбоновой кислоты;
объединение первого мономера, второго мономера, катализатора, растворителя и карбоновой кислоты в качестве полимеризационной смеси; и
нагревание полимеризационной смеси до более чем 120°С, где, по меньшей мере, один из первых мономеров или вторых мономеров является замещенным функциональностями, реакционноспособными по отношению к атому водорода, и, по меньшей мере, один из первых или вторых мономеров является замещенным функциональностями, реакционноспособными по отношению к атому неводорода, где функциональности, реакционноспособные по отношению к атому неводорода, представляют собой Cl, Br, I, OTs, OTf, CN, OCN, SCN, и где соотношение между функциональностями, реакционноспособными по отношению к атому водорода, и функциональностями, реакционноспособными по отношению к атому неводорода, делает возможной степень полимеризации, превышающую четыре.
2. Способ по п. 1, где первый мономер обладает структурой:
где х находится в диапазоне от 0 до 3; L независимо представляет собой H, Cl, Br, I, OTs, OTf, CN, OCN, SCN или другой псевдогалогенид, Х представляет собой S, Se, Te, O или NR; R независимо представляет собой Н, алкил, арил, замещенный алкил или замещенный арил, простой олигоэфир, аминоалкил, гидроксиалкил, алкоксиалкил, ацилоксиалкил, HOS(O)2алкил, НОС(О)алкил, (НО)2Р(О)алкил, аминоарил, гидроксиарил, алкоксиарил, ацилоксиарил, HOS(O)2арил, НОС(О)арил или (НО)2Р(О)арил, -(СН2)m-YC(O)R2, -(СН2)m-C(O)YR2, -(СН2)m-O-(CH2)vYC(O)R2, -(СН2)m-O-(CH2)vC(O)YR2, -(СН2)m-OCHz(CH3)y[(CH2)wYC(O)R2]3-z, -(СН2)m-OCHz(CH3)y[(CH2)wC(O)YR2]3-z, или две группы R на соседних атомах углерода в комбинации представляют собой алкилен, арилен, замещенный алкилен или замещенный арилен; m находится в диапазоне от 1 до 8; у находится в диапазоне от 0 до 2; z находится в диапазоне от 0 до 2; сумма y+z находится в диапазоне от 0 до 2; w находится в диапазоне от 1 до 8; v находится в диапазоне от 2 до 8; Y представляет собой O, S или NR3, R2 представляет собой прямоцепочечную, разветвленно-цепочечную, циклическую или замещенную циклическую алкильную группу, содержащую от 1 до 12 атомов углерода; а R3 представляет собой прямоцепочечную, разветвленно-цепочечную, циклическую или замещенную циклическую алкильную группу, содержащую от 1 до 6 атомов углерода.
3. Способ по п. 1, где второй мономер включает этен, карбазол, флуорен, бензотиадиазол, тиадиазолохиноксалин, хинолин, хиноксалин, тиенотиадиазол, тиенопиразин, пиразинохиноксалин, бензобистиадиазол, тиадиазолотиенопиразин, тиофен, пиррол, фуран, селенофен, теллурофен, тиено[3,2-b]тиофен, дитиено[3,2-b:2’,3’-d]тиофен, бензо[c][1,2,5]тиадиазол, бензо[c][1,2,5]оксадиазол, бензо[d][1,2,3]триазол, пиридо[3,4-b]пиразин, циановинилен, тиазоло[5,4-d]тиазол, 1,3,4-оксадиазол, 1,3,4-тиадиазол, 1,3,4-триазол, пирроло[3,4-c]пиррол-1,4-дион, 2,2’-битиазол, [1,2,5]тиадиазол[3,4-c]пиридин, тиено[3,4-b]пиразин, [1,2,5]оксадиазоло[3,4-c]пиридин, дициановинилен, бензо[1,2-c;4,5-c’]бис[1,2,5]тиадиазол, [1,2,5]тиадиазоло[3,4-g]хиноксалин, циклопентадитиофен-4-он, 4-дицианометиленциклопентадитиолен, бензо[c]тиофен, изоиндиго, индиго, 4,4’-бис(алкил)[6,6’-битиено[3,2-b]пирролилиден]-5,5’(4H,4’H)дион, фенантрен, фенантрен-9,10-дион, бензо[1,2-b:6,5-b’]дитиофен-4,5-дион, нафталиндиимид, перилендиимид, любое ароматическое соединение, обладающее структурой:
где L независимо представляет собой H, Cl, Br, I, OTs, OTf, CN, OCN, SCN или другой псевдогалогенид; Х представляет собой NR’, PR’, S, O, Se, Te, CR2, SiR’2, GeR’2, BR’ или SOx, где х = 1 или 2; Z представляет собой NR’, PR’, S, O, Se или Те; R’ независимо представляет собой Н, С1-30 алкил, С2-30 алкенил, С2-30 алкинил, С6-14 арил, С7-30 арилалкил, С8-30 арилалкенил, С8-30 арилалкинил, С1-С30 гидроксиалкил, С6-С14 гидроксиарил, С7-С30 гидроксиарилалкил, С3-С30 гидроксиалкенил, С3-С30 гидроксиалкинил, С8-С30 гидроксиарилалкенил, С8-С30 гидроксиарилалкинил, С3-С30 простой полиэфир, С3-С30 полиэфироэфир на основе простых и сложных эфиров, С3-С30 сложный полиэфир, С3-С30 полиамино, С3-С30 полиаминоамидо, С3-С30 простой полиаминоэфир, С3-С30 сложный полиаминоэфир, С3-С30 сложный полиамидоэфир, С3-С30 алкилсульфоновую кислоту, соль С3-С30 алкилсульфоновой кислоты, соль С1-С30 алкилкарбоновой кислоты, соль С1-С30 алкилтиокарбоновой кислоты, соль С1-С30 алкилдитиокарбоновой кислоты или С3-С30 алкил(С1-С4 триалкил)аммониевую соль; и R независимо представляет собой Н, С1-С30 алкил, С2-С30 алкенил, С2-С30 алкинил, С6-С14 арил, С7-С30 арилалкил, С8-С30 арилалкенил, С8-С30 арилалкинил, гидрокси, СО2Н, С2-С30 алкиловый сложный эфир, С7-С15 ариловый сложный эфир, С8-С30 алкилариловый сложный эфир, С3-С30 алкениловый сложный эфир, С3-С30 алкиниловый сложный эфир, NH2, С1-С30 алкиламино, С6-С14 ариламино, С7-С30 (арилалкил)амино, С2-С30 алкениламино, С2-С30 алкиниламино, С8-С30 (арилалкенил)амино, С8-С30 (арилалкинил)амино, С2-С30 диалкиламино, С12-С28 диариламино, С4-С30 диалкениламино, С4-С30 диалкиниламино, С7-С30 арил(алкил)амино, С7-С30 ди(арилалкил)амино, С8-С30 алкил(арилалкил)амино, С15-С30 арил(арилалкил)амино, С8-С30 алкенил(арил)амино, С8-С30 алкинил(арил)амино, С(О)NH2 (амидо), С2-С30 алкиламидо, С7-С14 ариламидо, С8-С30 (арилалкил)амидо, С2-С30 диалкиламидо, С12-С28 диариламидо, С8-С30 арил(алкил)амидо, С15-С30 ди(арилалкил)амидо, С9-С30 алкил(арилалкил)амидо, С16-С30 арил(арилалкил)амидо, тиол, С1-С30 гидроксиалкил, С6-С14 гидроксиарил, С7-С30 гидроксиарилалкил, С3-С30 гидроксиалкенил, С3-С30 гидроксиалкинил, С8-С30 гидроксиарилалкенил, С8-С30 гидроксиарилалкинил, С3-С30 простой полиэфир, С3-С30 полиэфироэфир на основе простых и сложных эфиров, С3-С30 сложный полиэфир, С3-С30 полиамино, С3-С30 полиаминоамидо, С3-С30 простой полиаминоэфир, С3-С30 сложный полиаминоэфир, С3-С30 сложный полиамидоэфир, С3-С30 алкилсульфоновую кислоту, соль С3-С30 алкилсульфоновой кислоты, соль С1-С30 карбоновой кислоты, соль С1-С30 тиокарбоновой кислоты, соль С1-С30 дитиокарбоновой кислоты или С3-С30 алкил(С1-С4 триалкил)аммониевую соль.
4. Способ по п. 1, где апротонный растворитель включает диметилформамид (ДМФА), ДМА, N-метилпирролидон (HMП), гексаметилфосфорамид (ГМФА), диметилсульфоксид (ДМСО) или пропиленкарбонат.
5. Способ по п. 1, где катализатор представляет собой диацетат палладия, дитрифторацетат палладия или бис(дибензилиденацетон)палладий(0).
6. Способ по п. 1, где карбоновой кислотой являются пивалиновая кислота или другая алифатическая карбоновая кислота.
7. Способ по п. 1, где температура составляет, по меньшей мере, 130°С.
8. Способ по п. 1, где температура составляет, по меньшей мере, 140°С.
9. Способ по п. 1, где полимеризационная смесь является свободной от фосфинового лиганда.
10. Способ по п. 1, где полимеризационная смесь является свободной от агента фазового переноса.
11. Способ по п. 1, где первый мономер представляет собой 3,3-бис((2-этилгексилокси)метил)-3,4-дигидро-2Н-тиено[3,4-b][1,4]диоксепин, 6,8-дибром-3,3-бис((2-этилгексилокси)метил)-3,4-дигидро-2Н-тиено[3,4-b][1,4]диоксепин и/или 6-бром-3,3-бис((2-этилгексилокси)метил)-3,4-дигидро-2Н-тиено[3,4-b][1,4]диоксепин.
12. Способ по п. 11, где второй мономер представляет собой 1,4-дибромбензол или 4,7-дибром-2,1,3-бензотиадиазол.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361836206P | 2013-06-18 | 2013-06-18 | |
| US61/836,206 | 2013-06-18 | ||
| PCT/US2014/042844 WO2014205024A1 (en) | 2013-06-18 | 2014-06-18 | Method for preparing dioxyheterocycle-based electrochromic polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2016101074A true RU2016101074A (ru) | 2017-07-21 |
Family
ID=52105201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016101074A RU2016101074A (ru) | 2013-06-18 | 2014-06-18 | Способ получения электрохромных полимеров на основе диоксигетероциклов |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9790326B2 (ru) |
| EP (1) | EP3010959B1 (ru) |
| JP (1) | JP6449865B2 (ru) |
| KR (1) | KR20160023788A (ru) |
| CN (1) | CN105473641A (ru) |
| AU (1) | AU2014281580A1 (ru) |
| BR (1) | BR112015031519A2 (ru) |
| CA (1) | CA2915381C (ru) |
| IL (1) | IL243062B (ru) |
| MX (1) | MX2015017659A (ru) |
| RU (1) | RU2016101074A (ru) |
| SG (1) | SG11201510277YA (ru) |
| WO (1) | WO2014205024A1 (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013111357B4 (de) | 2013-10-15 | 2015-11-05 | Lemken Gmbh & Co. Kg | Sämaschine mit Mehrfachfunktionswalze |
| US10294326B2 (en) | 2014-05-23 | 2019-05-21 | University Of Florida Research Foundation, Incorporated | Broadly absorbing electrochromic polymers |
| TWI516520B (zh) * | 2014-10-31 | 2016-01-11 | 財團法人工業技術研究院 | 波長轉換聚合物、其製法及包含其之波長轉換裝置 |
| US9902804B2 (en) | 2015-02-20 | 2018-02-27 | Georgia Tech Research Corporation | Donor-acceptor compositions to achieve high contrast broadly absorbing electrochromic polymers |
| CN105576125B (zh) * | 2016-02-04 | 2018-06-29 | 南京邮电大学 | 一种用于离子检测的有机场效应晶体管及其检测方法 |
| CN105679939A (zh) * | 2016-03-15 | 2016-06-15 | 南京邮电大学 | 一种基于掺杂噻吩异靛的有机薄膜场效应晶体管及其制备方法 |
| US9975989B2 (en) * | 2016-05-04 | 2018-05-22 | Furcifer Inc. | Multicolored electrochromic polymer compositions and methods of making and using the same |
| DK3652235T3 (da) * | 2017-07-14 | 2022-09-05 | Furcifer Inc | Elektokrom polymer og syntese og anvendelser deraf |
| CN108795089B (zh) * | 2018-07-23 | 2020-01-10 | 温州医科大学 | 基于二（噻吩并吡咯）并苯并噻二唑π桥的纯有机染料及其在染料敏化太阳能电池中的应用 |
| CN111072932A (zh) * | 2019-12-19 | 2020-04-28 | 南京宜凯瑞新材料有限公司 | 黑色至透明交联型电致变色聚合物及其制备方法 |
| CN111171292B (zh) * | 2020-02-14 | 2023-02-03 | 南京宜凯瑞新材料有限公司 | 两亲性电致变色聚合物及其制备方法 |
| CN111158167A (zh) * | 2020-02-14 | 2020-05-15 | 南京宜凯瑞新材料有限公司 | 可调光变色眼镜 |
| CN111349216B (zh) * | 2020-02-14 | 2023-02-03 | 南京宜凯瑞新材料有限公司 | 一种电致变色聚合物及用于大规模纯化电致变色聚合物的方法 |
| CN111187397B (zh) * | 2020-02-15 | 2023-02-24 | 南京宜凯瑞新材料有限公司 | 紫色至透明电致变色聚合物及其制备方法 |
| CN111171293A (zh) * | 2020-02-15 | 2020-05-19 | 南京宜凯瑞新材料有限公司 | 绿色至透明电致变色聚合物及其制备方法 |
| CN112574397A (zh) * | 2021-01-12 | 2021-03-30 | 长春工业大学 | 一类可绿色溶剂加工电致变色共轭聚合物制备及应用 |
| WO2024035888A1 (en) * | 2022-08-10 | 2024-02-15 | Kennesaw State University Research And Service Foundation, Inc. | Pyrrole derived compositions and sythesis methods |
| CN115926119B (zh) * | 2022-11-25 | 2024-10-15 | 中国人民解放军96901部队25分队 | 一种宽波段吸收的电致变色聚合物及其制备方法和一种电致变色薄膜 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3808071A1 (de) * | 1988-03-11 | 1989-09-21 | Basf Ag | Verfahren zur herstellung von acylierten imidazolen |
| DE102005031349A1 (de) * | 2005-07-05 | 2007-01-11 | H.C. Starck Gmbh | Verfahren zur Herstellung von Polyethylendioxythiophenen |
| LT2209830T (lt) * | 2007-10-30 | 2016-09-26 | University Of Florida Research Foundation, Inc. | Žali, pereinantys į pralaidžius, tirpūs elektrochrominiai polimerai |
| EP2449051B1 (en) * | 2009-07-02 | 2016-04-06 | University of Florida Research Foundation, Inc. | Soluble alternating donor-acceptor conjugated polymer electrochromes |
| WO2011075664A1 (en) | 2009-12-17 | 2011-06-23 | Abinitio Vsd Llc | Vacuum clip for storage bags |
| WO2011075644A2 (en) * | 2009-12-18 | 2011-06-23 | Plextronics, Inc. | Copolymers of 3,4-dialkoxythiophenes and methods for making and devices |
| EP2632996B1 (en) * | 2010-10-28 | 2019-12-25 | University of Florida Research Foundation, Incorporated | Cathodically coloring yellow soluble electrochromic and light emitting polymers |
| WO2013056355A1 (en) | 2011-10-20 | 2013-04-25 | UNIVERSITé LAVAL | Preparation of high molecular weight polymers 8y direct arylation and heteroarylation |
| KR101286014B1 (ko) * | 2011-11-21 | 2013-07-18 | 광주과학기술원 | 팔라듐계 촉매를 사용한 직접적 ｃｈ 아릴화 방법 |
| WO2015154190A1 (en) | 2014-04-11 | 2015-10-15 | The Governing Council Of The University Of Toronto | Conjugated polymers, and synthesis and use thereof |
| JP2016199658A (ja) | 2015-04-09 | 2016-12-01 | 国立大学法人山口大学 | 発光性材料、それを用いた発光性微粒子及びその製造方法 |
-
2014
- 2014-06-18 MX MX2015017659A patent/MX2015017659A/es unknown
- 2014-06-18 CN CN201480034567.9A patent/CN105473641A/zh active Pending
- 2014-06-18 WO PCT/US2014/042844 patent/WO2014205024A1/en active Application Filing
- 2014-06-18 RU RU2016101074A patent/RU2016101074A/ru unknown
- 2014-06-18 CA CA2915381A patent/CA2915381C/en not_active Expired - Fee Related
- 2014-06-18 SG SG11201510277YA patent/SG11201510277YA/en unknown
- 2014-06-18 AU AU2014281580A patent/AU2014281580A1/en not_active Abandoned
- 2014-06-18 JP JP2016521530A patent/JP6449865B2/ja not_active Expired - Fee Related
- 2014-06-18 US US14/897,063 patent/US9790326B2/en active Active
- 2014-06-18 KR KR1020167001389A patent/KR20160023788A/ko not_active Application Discontinuation
- 2014-06-18 EP EP14813805.0A patent/EP3010959B1/en active Active
- 2014-06-18 BR BR112015031519A patent/BR112015031519A2/pt not_active IP Right Cessation
-
2015
- 2015-12-07 IL IL243062A patent/IL243062B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014281580A1 (en) | 2016-01-21 |
| KR20160023788A (ko) | 2016-03-03 |
| US20160122476A1 (en) | 2016-05-05 |
| EP3010959A1 (en) | 2016-04-27 |
| MX2015017659A (es) | 2016-08-08 |
| US9790326B2 (en) | 2017-10-17 |
| CA2915381C (en) | 2021-04-27 |
| CN105473641A (zh) | 2016-04-06 |
| CA2915381A1 (en) | 2014-12-24 |
| WO2014205024A1 (en) | 2014-12-24 |
| EP3010959B1 (en) | 2021-04-21 |
| JP6449865B2 (ja) | 2019-01-09 |
| BR112015031519A2 (pt) | 2017-07-25 |
| JP2016523298A (ja) | 2016-08-08 |
| SG11201510277YA (en) | 2016-01-28 |
| AU2014281580A8 (en) | 2016-02-11 |
| EP3010959A4 (en) | 2017-03-08 |
| IL243062B (en) | 2019-09-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2016101074A (ru) | Способ получения электрохромных полимеров на основе диоксигетероциклов | |
| Kuwabara et al. | The effect of a solvent on direct arylation polycondensation of substituted thiophenes | |
| Kowalski et al. | Direct arylation polycondensation as simplified alternative for the synthesis of conjugated (co) polymers | |
| Wu et al. | Donor–acceptor polymers based on multi-fused heptacyclic structures: synthesis, characterization and photovoltaic applications | |
| Do et al. | Effect of the number of thiophene rings in polymers with 2, 1, 3-benzooxadiazole core on the photovoltaic properties | |
| Huo et al. | Benzo [1, 2-b: 4, 5-b′] dithiophene-based conjugated polymers: band gap and energy level control and their application in polymer solar cells | |
| TWI519565B (zh) | 共軛聚合物 | |
| TWI508992B (zh) | 半傳導性聚合物 | |
| JP5801322B2 (ja) | 半導体ポリマー | |
| Wu et al. | Synthesis and application of dithieno [2, 3-d: 2′, 3′-d′] benzo [1, 2-b: 4, 5-b′] dithiophene in conjugated polymer | |
| RU2012100902A (ru) | Растворимые сопряженные электрохромные полимеры с чередованием донорных и акцепторных звеньев | |
| Allard et al. | Easy and versatile synthesis of new poly (thieno [3, 4-d] thiazole) s | |
| JP2014515043A (ja) | 共役ポリマー | |
| RU2012145007A (ru) | Полимеры 8, 9-дигидробензо[def]карбазола и их применение в качестве органических полупроводников | |
| He et al. | Non-fullerene polymer solar cells with V OC> 1 V based on fluorinated quinoxaline unit conjugated polymers | |
| Hwang et al. | Synergistic effects of an alkylthieno [3, 2-b] thiophene π-bridging backbone extension on the photovoltaic performances of donor–acceptor copolymers | |
| TW201307432A (zh) | 共軛聚合物 | |
| Huang et al. | Synthesis and charge-transporting properties of electron-deficient CN 2–fluorene based D–A copolymers | |
| Park et al. | Effect of fused thiophene bridges on the efficiency of non-fullerene polymer solar cells made with conjugated donor copolymers containing alkyl thiophene-3-carboxylate | |
| Trilling et al. | π-Expanded diketopyrrolopyrroles as acceptor building blocks for the formation of novel donor–acceptor copolymers | |
| Sun et al. | Improved bulk-heterojunction polymer solar cell performance through optimization of the linker groupin donor–acceptor conjugated polymer | |
| Handoko et al. | Effect of cyano substituent on photovoltaic properties of quinoxaline-based polymers | |
| Hu et al. | Benzothiadiazole [1, 2-b: 4, 3-b′] dithiophene, a new ladder-type multifused block: Synthesis and photovoltaic application | |
| CN111683993B (zh) | 高分子化合物的制造方法 | |
| Deng et al. | Novel photovoltaic donor 1–acceptor–donor 2–acceptor terpolymers with tunable energy levels based on a difluorinated benzothiadiazole acceptor |