JP6418462B2 - ジケトピロロピロール半導体材料、その調製方法およびその使用 - Google Patents
ジケトピロロピロール半導体材料、その調製方法およびその使用 Download PDFInfo
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- JP6418462B2 JP6418462B2 JP2017012289A JP2017012289A JP6418462B2 JP 6418462 B2 JP6418462 B2 JP 6418462B2 JP 2017012289 A JP2017012289 A JP 2017012289A JP 2017012289 A JP2017012289 A JP 2017012289A JP 6418462 B2 JP6418462 B2 JP 6418462B2
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- Japan
- Prior art keywords
- optionally substituted
- alkyl
- group
- heteroaryl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000463 material Substances 0.000 title description 17
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title description 14
- 239000004065 semiconductor Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 34
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 33
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 125000004442 acylamino group Chemical group 0.000 claims description 22
- 125000004423 acyloxy group Chemical group 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 22
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
- 150000003573 thiols Chemical class 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
- 125000003107 substituted aryl group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 17
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
- 150000003462 sulfoxides Chemical class 0.000 claims description 16
- 125000001475 halogen functional group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 229930192474 thiophene Natural products 0.000 claims description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001356 alkyl thiols Chemical class 0.000 claims description 3
- -1 heterocyclic organic compounds Chemical class 0.000 description 69
- 125000001424 substituent group Chemical group 0.000 description 43
- 125000005843 halogen group Chemical group 0.000 description 42
- 229910052736 halogen Inorganic materials 0.000 description 23
- 150000002367 halogens Chemical class 0.000 description 23
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000003457 sulfones Chemical class 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229930194542 Keto Natural products 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000000468 ketone group Chemical group 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 125000000033 alkoxyamino group Chemical group 0.000 description 8
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
- 229910052787 antimony Inorganic materials 0.000 description 8
- 230000021615 conjugation Effects 0.000 description 8
- 125000005368 heteroarylthio group Chemical group 0.000 description 8
- 125000004470 heterocyclooxy group Chemical group 0.000 description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052714 tellurium Inorganic materials 0.000 description 5
- WFCTYNCVWIVGBK-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)N1C(CC=2C1=CC=1CC(N(C=1C=2)CCCCCCCCCCCCCCCC)=O)=O Chemical compound C(CCCCCCCCCCCCCCC)N1C(CC=2C1=CC=1CC(N(C=1C=2)CCCCCCCCCCCCCCCC)=O)=O WFCTYNCVWIVGBK-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 230000005669 field effect Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 208000015979 hopping Diseases 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- ICCBZGUDUOMNOF-UHFFFAOYSA-N azidoamine Chemical compound NN=[N+]=[N-] ICCBZGUDUOMNOF-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 230000005610 quantum mechanics Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000005156 substituted alkylene group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- ATCJTYORYKLVIA-SRXJVYAUSA-N vamp regimen Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1.C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C(C45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 ATCJTYORYKLVIA-SRXJVYAUSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- HKAIIKVJIRPASO-UHFFFAOYSA-N 1-butylpyrrolidine-2,5-dione Chemical compound CCCCN1C(=O)CCC1=O HKAIIKVJIRPASO-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 1
- AYIJDKOYXMRYKJ-UHFFFAOYSA-N 9h-carbazole;pteridine Chemical compound N1=CN=CC2=NC=CN=C21.C1=CC=C2C3=CC=CC=C3NC2=C1 AYIJDKOYXMRYKJ-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 230000002336 repolarization Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 150000003606 tin compounds Chemical class 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- 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
- C08G61/124—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 nitrogen atom in the ring
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
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- 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
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- 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
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Description
Arは、随意的に置換された芳香族またはヘテロ芳香族基であり;kが0である場合、その構造により、チオフェン基とピロール基との間に直接結合が生じるという条件で、kは、0から5の整数であり;共役のために、Xは1つ以上の追加のR1に結合されることがあるという条件で、各Xは、独立して、NR1、PR1、AsR1、Sb、O、S、Te、またはSeであり;各Yは、独立して、H、ハロ、トリアルキルシラン、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、アリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、ハロ、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、随意的に置換されたスルホン、OSO−アルキル、Mg−ハロ、Zn−ハロ、Sn(アルキル)3、SnH3、B(OH)2、B(アルコキシ)2、またはOTsであり;各R、R1、R2、およびR3は、独立して、H、ハロ、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、随意的に置換されたアリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、ハロ、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、または随意的に置換されたスルホンである。
Arは、随意的に置換された芳香族またはヘテロ芳香族基または共役基であり;kが0である場合、その構造により、チオフェン基とジインドール基との間に直接結合が生じるという条件で、kは、0から5の整数であり;nはゼロより大きい整数であり;共役のために、Xは1つ以上の追加のR1に結合されることがあるという条件で、各Xは、独立して、NR1、PR1、AsR1、Sb、O、S、Te、またはSeであり;各R、R1、R2、およびR3は、独立して、H、ハロ、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、随意的に置換されたアリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、または随意的に置換されたスルホンである。
Arは、随意的に置換された芳香族またはヘテロ芳香族基または共役基であり;kが0である場合、その構造により、チオフェン基とピロール基との間に直接結合が生じるという条件で、kは、0から5の整数であり;共役のために、Xは1つ以上の追加のR1に結合されることがあるという条件で、各Xは、独立して、NR1、PR1、AsR1、Sb、O、S、Te、またはSeであり;各Yは、独立して、H、ハロ、トリアルキルシラン、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、アリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、ハロ、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、随意的に置換されたスルホン、OSO−アルキル、Mg−ハロ、Zn−ハロ、Sn(アルキル)3、SnH3、B(OH)2、B(アルコキシ)2、またはOTsであり;各R、R1、R2、およびR3は、独立して、H、ハロ、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、随意的に置換されたアリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、ハロ、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、または随意的に置換されたスルホンである、組成物がここに記載されている。
下記構造の化合物:
構造1aまたは1bを有する、実施形態1に記載の化合物。
構造1c、1d、または1eを有する、実施形態1に記載の化合物。
構造2を有する、実施形態1に記載の化合物。
kが0〜3である、実施形態1から4いずれか1つに記載の化合物。
kが0である、実施形態5に記載の化合物。
Arが随意的に置換されたアリールまたはヘテロアリールである、実施形態1から5いずれか1つに記載の化合物。
Arがチオフェンまたは縮合チオフェンである、実施形態1から5いずれか1つに記載の化合物。
前記チオフェンまたは縮合チオフェンが、α位で化合物に結合しており、β位で1つ以上のC1〜C20アルキル基により随意的に置換されている、実施形態8に記載の化合物。
Xが、N、SまたはOである、実施形態1から9いずれか1つに記載の化合物。
Yが、H、随意的に置換されたアルキル、またはハロである、実施形態1から10いずれか1つに記載の化合物。
各R1およびR3が、独立して、H、随意的に置換されたアルキル、ハロ、随意的に置換されたアルコキシ、随意的に置換されたアルキルチオール、または随意的に置換されたアルケニルである、実施形態1から11いずれか1つに記載の化合物。
各RおよびR2が、独立して、H、随意的に置換されたアルキル、ハロ、または随意的に置換されたアルコキシである、実施形態12に記載の化合物。
実施形態1から13いずれか1つに記載の化合物を製造する方法であって、
下記構造:
下記構造:
Xがハロであり、ZがHまたは随意的に置換されたアルキルである、方法。
下記構造の少なくとも1つの部分を含むポリマー:
nが1から500の整数である、実施形態15に記載のポリマー。
nが3から20の整数である、実施形態16に記載のポリマー。
構造1a’または1b’を有する、実施形態15から17いずれか1つに記載のポリマー。
構造1c’、1d’、または1e’を有する、実施形態15から17いずれか1つに記載のポリマー。
構造2’を有する、実施形態15から17いずれか1つに記載のポリマー。
kが0から3である、実施形態15から20いずれか1つに記載のポリマー。
kが0である、実施形態21に記載のポリマー。
Arが随意的に置換されたアリールまたはヘテロアリールである、実施形態15から22いずれか1つに記載のポリマー。
Arがチオフェンまたは縮合チオフェンである、実施形態23に記載のポリマー。
前記チオフェンまたは縮合チオフェンが、α位で化合物に結合しており、β位で1つ以上のC1〜C20アルキル基により随意的に置換されている、実施形態24に記載のポリマー。
Xが、N、SまたはOである、実施形態15から25いずれか1つに記載のポリマー。
Yが、H、随意的に置換されたアルキル、またはハロである、実施形態15から26いずれか1つに記載のポリマー。
各R1およびR3が、独立して、H、随意的に置換されたアルキル、ハロ、随意的に置換されたアルコキシ、随意的に置換されたアルキルチオール、または随意的に置換されたアルケニルである、実施形態15から27いずれか1つに記載のポリマー。
各RおよびR2が、独立して、H、随意的に置換されたアルキル、ハロ、または随意的に置換されたアルコキシである、実施形態28に記載のポリマー。
実施形態15から29いずれか1つに記載のポリマーを製造する方法であって、
下記構造:
下記構造:
Xがハロであり、ZがHまたは随意的に置換されたアルキルである、方法。
Claims (9)
- 下記構造の少なくとも1つを含むポリマー:
nはゼロより大きい整数であり;
Arは、随意的に置換された芳香族またはヘテロ芳香族基または共役基であり;
kは、0から5の整数であり、但し、kが0の場合、チオフェン基とピロール基との間に直接結合が生じる;
各R、R2、およびR3は独立して、H、ハロ、随意的に置換されたC1〜C40アルキル、随意的に置換されたアラルキル、アルコキシ、アルキルチオ、随意的に置換されたC2〜C40アルケニル、随意的に置換されたC2〜C40アルキニル、アミノカルボニル、アシルアミノ、アシルオキシ、随意的に置換されたアリール、アリールオキシ、随意的に置換されたアミノ、カルボキシアルキル、随意的に置換されたシクロアルキル、随意的に置換されたシクロアルケニル、アシル、随意的に置換されたヘテロアリール、随意的に置換されたヘテロアラルキル、ヘテロアリールオキシ、随意的に置換されたヘテロシクリル、チオール、アルキルチオ、ヘテロアリールチオール、随意的に置換されたスルホキシド、または随意的に置換されたスルホンである。 - nが1から500の整数である、請求項1記載のポリマー。
- 構造1a’または1b’を含む、請求項1または2記載のポリマー。
- kが0から3である、請求項1から3いずれか1項記載のポリマー。
- Arが随意的に置換されたアリールまたはヘテロアリールである、請求項1から4いずれか1項記載のポリマー。
- Arがチオフェンまたは縮合チオフェンである、請求項1から5いずれか1項記載のポリマー。
- 各R3が独立して、H、随意的に置換されたアルキル、ハロ、随意的に置換されたアルコキシ、随意的に置換されたアルキルチオール、または随意的に置換されたアルケニルである、請求項1から6いずれか1項記載のポリマー。
- 各RおよびR2が独立して、H、随意的に置換されたアルキル、ハロ、または随意的に置換されたアルコキシである、請求項7記載のポリマー。
- 請求項1から8いずれか1項記載のポリマーを製造する方法であって、
下記構造:
下記構造:
Xはハロであり、ZはHまたは随意的に置換されたアルキルである、方法。
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EP3680241A1 (en) | 2017-03-20 | 2020-07-15 | Forma Therapeutics, Inc. | Pyrrolopyrrole compositions as pyruvate kinase (pkr) activators |
KR102235223B1 (ko) | 2017-11-28 | 2021-04-02 | 주식회사 엘지화학 | 광활성층 및 이를 포함하는 유기태양전지 |
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WO2020061378A1 (en) | 2018-09-19 | 2020-03-26 | Forma Therapeutics, Inc. | Treating sickle cell disease with a pyruvate kinase r activating compound |
US20230055923A1 (en) | 2018-09-19 | 2023-02-23 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
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US20130085256A1 (en) | 2004-09-14 | 2013-04-04 | Mingqian He | Fused thiophenes, methods of making fused thiophenes, and uses thereof |
CA2700713A1 (en) | 2007-10-09 | 2009-04-16 | Zhimin Hao | Pyrrolopyrrole derivatives, their manufacture and use |
DE102008018748A1 (de) | 2008-04-14 | 2009-10-15 | Repower Systems Ag | Windenergieanlage mit Anschlussschutzeinrichtung |
KR101582696B1 (ko) | 2009-04-21 | 2016-01-06 | 엘지전자 주식회사 | 다중 반송파 시스템에서 무선통신의 수행장치 및 방법 |
JP5675787B2 (ja) | 2009-05-27 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有機半導体装置で使用するためのジケトピロロピロールポリマー |
WO2011025455A1 (en) * | 2009-08-28 | 2011-03-03 | Agency For Science, Technology And Research | P-type materials and organic electronic devices |
JP2013523931A (ja) | 2010-03-31 | 2013-06-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 縮合環系ジチオフェンコポリマー |
US8729220B2 (en) | 2010-03-31 | 2014-05-20 | Basf Se | Annellated dithiophene copolymers |
US8217183B2 (en) | 2010-05-18 | 2012-07-10 | Corning Incorporated | Methods of making fused thiophenes |
US8278346B2 (en) | 2010-08-06 | 2012-10-02 | Corning Incorporated | Di-tin fused thiophene compounds and polymers and methods of making |
WO2012058209A1 (en) | 2010-10-27 | 2012-05-03 | Plextronics, Inc. | Organic electronic devices, including organic photovoltaic devices, polymers, and monomers |
TWI635111B (zh) * | 2012-03-16 | 2018-09-11 | 馬克專利公司 | 共軛聚合物 |
JP2015519300A (ja) | 2012-03-29 | 2015-07-09 | コーニング インコーポレイテッド | 新規な縮合ナフタレンシクロヘテロ環式化合物、並びにその方法及び使用 |
US9379335B2 (en) * | 2012-04-08 | 2016-06-28 | The Regents Of The University Of California | Benzodipyrrolidones and their polymers: synthesis and applications for organic electronics and optoelectronics |
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2015
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CN106573940A (zh) | 2017-04-19 |
US9896536B2 (en) | 2018-02-20 |
KR20160127106A (ko) | 2016-11-02 |
JP2017119872A (ja) | 2017-07-06 |
JP6366728B2 (ja) | 2018-08-01 |
US20160365518A1 (en) | 2016-12-15 |
US10100143B2 (en) | 2018-10-16 |
EP3147287A1 (en) | 2017-03-29 |
EP3110821B1 (en) | 2019-10-30 |
CN106573940B (zh) | 2019-10-25 |
WO2015130915A1 (en) | 2015-09-03 |
US20180118879A1 (en) | 2018-05-03 |
TW201542555A (zh) | 2015-11-16 |
SG11201607135SA (en) | 2016-09-29 |
US20160362517A1 (en) | 2016-12-15 |
JP2017507948A (ja) | 2017-03-23 |
EP3110821A1 (en) | 2017-01-04 |
US10144800B2 (en) | 2018-12-04 |
TWI639604B (zh) | 2018-11-01 |
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