EP3452474A1 - Organic ternary blends - Google Patents
Organic ternary blendsInfo
- Publication number
- EP3452474A1 EP3452474A1 EP17723482.0A EP17723482A EP3452474A1 EP 3452474 A1 EP3452474 A1 EP 3452474A1 EP 17723482 A EP17723482 A EP 17723482A EP 3452474 A1 EP3452474 A1 EP 3452474A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- optionally substituted
- independently
- aryl
- composition
- heteroaryl
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 239000000370 acceptor Substances 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 102
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 67
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 64
- 125000001931 aliphatic group Chemical group 0.000 claims description 54
- 125000005842 heteroatom Chemical group 0.000 claims description 52
- -1 heteroaliphatic Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003384 small molecules Chemical class 0.000 claims description 8
- 230000002950 deficient Effects 0.000 claims description 7
- 229910052732 germanium Inorganic materials 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000005466 alkylenyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000013590 bulk material Substances 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 claims description 2
- 230000001699 photocatalysis Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 229910003472 fullerene Inorganic materials 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000012267 brine Substances 0.000 description 10
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- UPCYEFFISUGBRW-UHFFFAOYSA-N 3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound CCN1C(=O)CSC1=S UPCYEFFISUGBRW-UHFFFAOYSA-N 0.000 description 7
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000000137 annealing Methods 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- PGZSJKQDQHLSJG-UHFFFAOYSA-N dichloro(dioctyl)germane Chemical compound CCCCCCCC[Ge](Cl)(Cl)CCCCCCCC PGZSJKQDQHLSJG-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000935 solvent evaporation Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- HKJHYTKBDDVGRK-IOUDQCQMSA-N (5Z)-3-ethyl-2-sulfanylidene-5-[[4-[9,9,18,18-tetrakis(2-ethylhexyl)-15-[7-[(Z)-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,1,3-benzothiadiazol-4-yl]-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaen-6-yl]-2,1,3-benzothiadiazol-7-yl]methylidene]-1,3-thiazolidin-4-one Chemical compound CCCCC(CC)CC1(CC(CC)CCCC)c2cc(sc2-c2cc3c(cc12)-c1sc(cc1C3(CC(CC)CCCC)CC(CC)CCCC)-c1ccc(\C=C2/SC(=S)N(CC)C2=O)c2nsnc12)-c1ccc(\C=C2/SC(=S)N(CC)C2=O)c2nsnc12 HKJHYTKBDDVGRK-IOUDQCQMSA-N 0.000 description 3
- XCRWUZOODPKQQB-UHFFFAOYSA-N 2-N,2-N,6-N,6-N-tetraethyl-3,7-dihydroxynaphthalene-2,6-dicarboxamide Chemical compound C(C)N(C(=O)C1=CC2=CC(=C(C=C2C=C1O)C(=O)N(CC)CC)O)CC XCRWUZOODPKQQB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- GBTYXLLVZDUERL-UHFFFAOYSA-N [6-(diethylcarbamoyloxy)naphthalen-2-yl] N,N-diethylcarbamate Chemical compound C(C)N(C(OC1=CC2=CC=C(C=C2C=C1)OC(N(CC)CC)=O)=O)CC GBTYXLLVZDUERL-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- YWFGSZXYXPXBFF-UHFFFAOYSA-N dimethyl 3,7-dihydroxynaphthalene-2,6-dicarboxylate Chemical compound OC=1C(=CC2=CC(=C(C=C2C=1)C(=O)OC)O)C(=O)OC YWFGSZXYXPXBFF-UHFFFAOYSA-N 0.000 description 3
- UWTJPNYSQHCWDV-UHFFFAOYSA-N dimethyl 3,7-dithiophen-2-ylnaphthalene-2,6-dicarboxylate Chemical compound COC(=O)C1=CC2=CC(=C(C=C2C=C1C=1SC=CC=1)C(=O)OC)C=1SC=CC=1 UWTJPNYSQHCWDV-UHFFFAOYSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- YVFXJPBZGXLIPW-UHFFFAOYSA-N 3-bromo-2-[2,5-dibromo-4-(3-bromothiophen-2-yl)phenyl]thiophene Chemical compound C1=CSC(C=2C(=CC(=C(Br)C=2)C2=C(C=CS2)Br)Br)=C1Br YVFXJPBZGXLIPW-UHFFFAOYSA-N 0.000 description 2
- VPDPNJVAWKCZEH-UHFFFAOYSA-N 4-bromo-2,1,3-benzothiadiazole-7-carbaldehyde Chemical compound BrC1=CC=C(C=O)C2=NSN=C12 VPDPNJVAWKCZEH-UHFFFAOYSA-N 0.000 description 2
- OKVJKEGHHLZGNB-UHFFFAOYSA-N 5-bromo-1,2,3-benzothiadiazole-4-carbaldehyde Chemical group BrC1=CC=C2C(N=NS2)=C1C=O OKVJKEGHHLZGNB-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XOJVVFBFDXDTEG-UHFFFAOYSA-N Norphytane Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 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
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 1
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- SURAFOYTVQAFCK-UHFFFAOYSA-N dimethyl 1,4-dimethyl-3,7-dithiophen-2-ylnaphthalene-2,6-dicarboxylate Chemical compound COC(=O)C1=C(C2=CC(=C(C=C2C(=C1C=1SC=CC=1)C)C(=O)OC)C=1SC=CC=1)C SURAFOYTVQAFCK-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RZCSPUKVPNZXPV-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]pyridine Chemical compound S1C=CC2=C1C=NC1=C2SC=C1 RZCSPUKVPNZXPV-UHFFFAOYSA-N 0.000 description 1
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 238000004773 frontier orbital Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000009862 microstructural analysis Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/30—Germanium compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- 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
Definitions
- the invention relates to organic blends comprising more than one non-fullerene electron acceptors for use in organic optical or electronic devices.
- a ternary system offers a simple and alternative approach to enhance the light harvesting in a single junction device.
- a typical ternary BHJ system consists of two electron donor and an electron acceptor usually a fullerene derivative or vice versa.
- Recently, many groups have reported different types of ternary blend systems, such as two electron donor polymers or one polymer and a small molecule donor and a fullerene acceptor, one polymer donor and two fullerene derivatives as electron acceptors. In most cases, ternary blends have surpassed the corresponding binary blends mainly due to increase in short circuit current (J sc ).
- ternary blends The working mechanism of ternary blends depends on a particular blend structure and can be of following four types, charge transfer (CT), energy transfer, parallel and alloy structure. One or all of the four mechanisms may possibly be present in a particular ternary system.
- CT charge transfer
- One or all of the four mechanisms may possibly be present in a particular ternary system.
- the resultant performance greatly depends on the blend morphology, miscibility and surface energy of donor or acceptor components.
- the third component plays an important role in the blend morphology and can act as a vitrifying or crystallisation template to facilitate a favourable BHJ morphology. Careful design and judicial positioning of energy levels are crucial for efficient charge transport.
- the low band gap polymer or molecule can act as a sensitizer and transfer holes to the wide band gap donor component.
- the open circuit voltage (V oc ) is usually pinned to the smallest V oc of corresponding binary blend.
- the working mechanism can be parallel-like or alloy type. In case of parallel-like ternary solar cells, excitons generated in an individual donor would migrate to the respective donor/acceptor interface and then dissociate into free electrons and holes.
- V oc can be tuned across its full composition range in such ternary systems and record efficiencies are achieved with low band gap polymers.
- the materials used in these systems present difficulties to scale up, issues with solubility, device irreproducibility and photochemical instability.
- P3HT is the only polymer being scaled above 10 Kg scale, making it a strong candidate for OPV commercialisation, and it has already been widely employed in large area, printed solar cells.
- P3HT is often neglected due to narrow absorption, it is important to develop new acceptors that can be used with P3HT.
- FBR non-fullerene acceptor
- the invention provides a composition comprising a blend of two or more organic electron acceptor compounds and an organic electron donor compound, wherein at least one of the electron acceptor compounds is a compound of Formula (I):
- A is a divalent conjugated fused ring system containing aromatic groups directly conjugated to groups B 1 and B 2 , and having the structure:
- X ! is C, Ge or Si
- R 1 is, at each occurrence, independently, H, or optionally substituted Ci. 30 aliphatic, aryl or heteroaryl;
- Cy 1"10 are, at each occurrence, independently, absent or a 5 or 6-membered ring having 0, 1 or 2 ring heteroatoms, or a fused polycyclic (for example, bicyclic or tricyclic) ring optionally having one or more ring heteroatoms, provided that at least one of Cy 1"5 and at least one of Cy 6"10 is not absent, and wherein each of Cy 1"10 , when present, is optionally substituted by one or more groups R 2 ; R 2 is, at each occurrence, independently, halo, Ci.
- aliphatic, aryl, heteroaryl, silyl or hydrocarbyl are optionally substituted, and wherein X° is halogen and R° and R 00 are, independently, H or optionally substituted Ci. 40 hydrocarbyl; or two R 2 , with the intervening atoms form an optionally substituted fused ring, having 0, 1 or 2 ring heteroatoms;
- Y 1 and Y 2 are, independently, H, F, CI or CN;
- a and b are, independently of each other, 0, 1 or 2;
- T 1 and T 2 are, independently of each other, an electron deficient group conjugated to group B 1 or B 2 , respectively, or wherein when a and/or b are 0, T 1 and T 2 are, independently of each other, an electron deficient group conjugated to group A, respectively;
- A contains an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups B 1 and B 2 , respectively, or wherein when a and/or b are 0, A contains an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups T 1 and T 2 , respectively.
- * represents the bond to B 1 and B 2 , respectively.
- the one of Cy 1"10 which is bonded to B 1 or B 2 , respectively is an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms .
- the one of Cy 1"10 which is bonded to T 1 or T 2 , respectively is an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups T 1 and T 2 , respectively.
- Cy 1"10 are preferably, at each occurrence, independently, absent or a 5 or 6-membered ring having 0, 1 or 2 ring heteroatoms, each optionally substituted by one or more groups R 2 , provided that at least one of Cy 1"5 and at least one of Cy 6"10 is not absent.
- the one of Cy 1"5 and at the one of Cy 6"10 that are directly bonded to groups B 1 and B 2 , or wherein when a and/or b are 0, the one of Cy 1"5 and at the one of Cy 6"10 that are directly bonded to groups T 1 and T 2 , are each independently a 5 or 6-membered aromatic ring having 0, 1 or 2 ring heteroatoms (preferably phenyl or thiophenyl), each optionally substituted by one or more groups R 2 .
- Cy 1"10 may have the , wherein X ! is C, Ge or Si.
- Cy 1"10 is preferably, independently, abs ent, or a 5 or 6-membered aromatic ring having 0, 1 or 2 ring heteroatoms (preferably phenyl or thiophenyl), each optionally substituted by one or more groups R 2 .
- Cy 4"10 are at each occurrence, independently a 5 or 6-membered aromatic ring having 0, 1 or 2 ring heteroatoms (preferably phenyl or thiophenyl), each optionally substituted by one or more groups R 2 .
- A may be selected from:
- R 1 may, at each occurrence, independently, be Ci-3o aliphatic or aryl optionally substituted with CM 0 aliphatic, preferably C 6 -io aliphatic (for example, linear or branched C 8 aliphatic) or aryl (for example, phenyl) substituted with Ci_ 6 aliphatic.
- R 2 may, at each occurrence, independently, be H, optionally substituted Ci. 30 aliphatic, aryl or heteroaryl, preferably Ci.
- CM 0 aliphatic preferably C 6 -s aliphatic (for example, linear or branched C 8 aliphatic) or aryl (for example, phenyl) substituted with Ci_ 6 aliphatic.
- Prefera is:
- X 2 is S, O or C(R 6 ) 2 ;
- W is S, O or C(R 6 ) 2 ;
- heteroaliphatic, aryl, heteroaryl, silyl or hydrocarbyl are optionally substituted, and wherein X° is halogen and R° and R 00 are, independently, H or optionally substituted C1-40 hydrocarbyl (preferably optionally substituted aliphatic, heteroaliphatic, aryl or heteroaryl);
- n 0-4.
- n 0-3 and o is 0-2; and R 5 , R 6 and X 2 are as defined above.
- X 2 is O.
- R 5 is preferably CM 2 aliphatic, preferably CM alkyl, more preferably Ci_ 8 alkyl.
- a and b are, independently, 1 or 2, more preferably a and b are both 1.
- each occurrence of B 1 and B 2 may preferably be, independently, mono-, bi- or tri-cyclic aryl or heteroaryl group, unsubstituted or substituted by one or more groups R 3 , wherein the aryl or heteroaryl group may optionally include a non-aromatic carbocyclic or heterocyclic ring fused thereto.
- one or more occurrences of B 1 and B 2 is:
- a compound of Formula (I) as defined herein may preferably be selected from:
- R 1 is Ci -8 aliphatic, preferably -CsH ! 7 or -CH2C(C2H5)HC 4 H 9 and R 5 is methyl or ethyl (preferably ethyl).
- a compound of Formula (I) as defined herein may preferably be selected from:
- a composition according to any embodiment of the first aspect of the invention comprises a first electron acceptor compound and a second electron acceptor compound.
- the first electron acceptor compound is a compound of formula (I) as defined herein and the second electron acceptor compound is a compound
- the second electron acceptor compound may be a small molecule, for example a compound having a molecular weight of 1000Da or less.
- both the first and the second electron acceptor compounds are a compound of formula (I) as defined herein, provided that the first and electron acceptor compounds of formula (I) are not the same.
- the composition comprises a first electron acceptor compound and a second electron acceptor compound, wherein the second electron acceptor compound has an electron affinity and ionization potential between that of the electron donor and the first electron acceptor compound.
- the composition comprises a first electron acceptor compound and a second electron acceptor compound, wherein the first electron acceptor compound has an electron affinity and ionization potential between that of the electron donor and the second electron acceptor compound.
- the first electron acceptor compound is compound of formula (I) and the second electron acceptor compound is a compound as depicted in Figure 7.
- the electron donor is preferably a polymer or small molecule, e.g. a small molecule light absorber.
- P3HT Preferabl 5-diyl
- Y4 exemplary electron donor compounds
- Other exemplary electron donor compounds include the polymeric compounds disclosed in WO 2013/000532, US 2015/0255725 and US
- composition comprises an IDTBR moiety
- composition comprises IDTBR and IDFBR at a weight ratio of 0.6-0.7:0.3-0.4.
- a composition of the invention may be provided, for example, in the form of a bulk material or a film, for example a thin film.
- a thin film is a film with a thickness of about 100 ⁇ or less, preferably from about 5nm to about 100 ⁇ , more preferably from about 5 to about 500nm.
- the invention provides an optical or electronic device comprising a composition according to any one of the preceding claims.
- the device is a photovoltaic cell (optionally an organic solar cell), an organic transistor, a light emitting diode, a photodetector or a photocatalytic device.
- the device may further comprise an anode and a cathode.
- the composition may forms an active layer between the anode and the cathode.
- the device is an organic solar cell comprising a bulk
- heterojunction active layer comprising the composition according to the first aspect of the invention.
- the device further comprises a hole transport layer and an electron transport layer.
- the invention provides a process for producing a composition according to the first aspect of the invention, the process comprising:
- the first and second organic electron acceptors and the organic electron donor are selected such that the second electron acceptor compound has an electron affinity and ionization potential between that of the electron donor and the first electron acceptor compound.
- the invention provides a process for producing a device according to the second aspect of the invention, comprising
- the process further comprises depositing an electrode on the active layer.
- the invention provides a compound of Formula (IA)
- A is a divalent conjugated fused ring system having the structure:
- Xi is C, Ge or Si (preferably C);
- R 1 is, at each occurrence, independently, H, or optionally substituted Ci. 30 aliphatic, aryl or heteroaryl;
- Cy 1"8 are, at each occurrence, independently, absent or a 5 or 6-membered ring having 0, 1 or 2 ring heteroatoms, or a fused polycyclic (for example bicyclic or tricyclic) ring optionally having one or more ring heteroatoms, provided that at least one of Cy 1"4 and at least one of Cy 5"8 is not absent, and wherein each of Cy 1"8 , when present, is optionally substituted by one or more groups R 2 ;
- Y 1 and Y 2 are, independently, H, F, CI or CN;
- a and b are, independently of each other, 0, 1 or 2;
- T 1 and T 2 are, independently of each other, an electron deficient group conjugated to group B 1 or B 2 , respectively, or wherein when a and/or b are 0, T 1 and T 2 are, independently of each other, an electron deficient group conjugated to group A, respectively;
- A contains an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups B 1 and B 2 , respectively, or wherein when a and/or b are 0, A contains an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups T 1 and T 2 , respectively.
- each occurrence of * represents the bond to B 1 and B 2 , respectively.
- the point of attachment to B 1 and B 2 is instead on the next adjacent one of Cy 1"10 that is not absent.
- the bond between A and B 1 will be between Cy 2 and B 1 .
- a or b, respectively is not 0, the one of Cy 1"10 which is bonded to B 1 or B 2 , respectively, is an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms .
- the one of Cy 1"10 which is bonded to T 1 or T 2 , respectively, is an optionally substituted aromatic ring having 0, 1 , 2 or more ring heteroatoms directly bonded to groups T 1 and T 2 , respectively.
- Cy 1"10 are preferably, at each occurrence, independently, absent or a 5 or 6-membered ring having 0, 1 or 2 ring heteroatoms, each optionally substituted by one or more groups R 2 , provided that at least one of Cy 1"5 and at least one of Cy 6"10 is not absent.
- the one of Cy 1"5 and at the one of Cy 6"10 that are directly bonded to groups B 1 and B 2 , or wherein when a and/or b are 0, the one of Cy 1"5 and at the one of Cy 6"10 that are directly bonded to groups T 1 and T 2 , are each independently a 5 or 6-membered aromatic ring having 0, 1 or 2 ring heteroatoms (preferably phenyl), each optionally substituted by one or more groups R 2 .
- Cy 1"8 may have the structure V— .
- A may preferably be selected from: wherein Cy 1"8 are as defined above.
- Cy 1-8 are, at each occurrence, independently a 5 or 6-membered aromatic ring having 0, 1 or 2 ring heteroatoms (preferably phenyl), optionally substituted by one or more groups R 2 .
- A is , optionally substituted by one or more groups R 2 .
- R 1 may, at each occurrence, independently, be Ci-3o aliphatic or aryl optionally substituted with CM 0 aliphatic, preferably C 6 -io aliphatic (for example, linear or branched C 8 aliphatic) or aryl (for example, phenyl) substituted with Ci_ 6 aliphatic.
- R 2 may, at each occurrence, independently, be H, optionally substituted Ci. 30 aliphatic, aryl or heteroaryl, preferably Ci. 30 aliphatic or aryl substituted with CM 0 aliphatic, preferably C 6 -s aliphatic (for example, linear or branched C 8 aliphatic) or aryl (for example, phenyl) substituted with Ci_ 6 aliphatic.
- Prefera is:
- W is S, O or C(R 6 ) 2 (preferably S);
- -- ⁇ ' may be present or absent and represents a fused mono-, bi- or tri- cyclic hydrocarbyl group, preferably aryl or heteroaryl, optionally substituted by one or more R 7 , wherein R 7 has the meaning of R 2 ;
- n 0-4.
- n 0-3 and o is 0-2 and R 5 , R 6 and X 2 are as defined above.
- X 2 is O.
- R 5 is preferably CM 2 aliphatic, preferably CM 2 alkyl, more preferably Ci_ 8 alkyl.
- a and b are, independently, 1 or 2, more preferably a and b are both 1 .
- each occurrence of B 1 and B 2 may preferably be, independently, mono-, bi- or tri-cyclic aryl or heteroaryl group, unsubstituted or substituted by one or more groups R 3 , wherein the aryl or heteroaryl group may optionally include a non-aromatic carbocyclic or heterocyclic ring fused thereto.
- one or more occurrences of B 1 and B 2 is:
- p 0, 1 or 2;
- a compound of Formula (IA) as defined herein, may preferably be selected from:
- a compound of Formula (IA) as defined herein, may preferably be selected from:
- R 1 is Ci -8 alkyl, preferably -C 8 H 17 or -CH 2 C(C2H5)HC 4 H9 and R 5 is methyl ethyl (preferably ethyl).
- Figure 1 (a to b) shows exemplary electron acceptor and donor compounds.
- Figure 2 shows a) the UV-absorption spectra for IDTBR, OIDFBR and P3HT, b) the energy level diagrams of P3HT, FBR, IDFBR, IDTBR and 60PCBM and c) the change in thin films absorption of binary P3HT: IDTBR and ternary P3HT: IDTBR: IDFBR blends upon annealing in inert atmosphere at 130 °C for 10 mins..
- Figure 3 shows a) the JV and b) EQE spectra of IDTBR: IDFBR: P3HT ternary solar cells.
- Figure 4 shows variations in Voc, FF, Jsc and PCE(%) of ternary blends of
- IDTBR IDFBR: P3HT as a function of change in IDFBR weight ratio.
- Figure 5 shows microstructural analysis of P3HT: IDTBR: IDFBR ternary blend a) DSC heating profiles of individual P3HT, IDTBR and IDFBR along with binary P3HT: IDTBR, P3HT:IDFBR and ternary P3HT: IDTBR: IDFBR blends; b) illustration of the binary
- P3HT:IDTBR blend without IDFBR presence where crystallinity of both P3HT and IDTBR is preserved
- Figure 6 shows the oxidative stability of a IDTBR:IDFBR:P3HT device efficiencies (PCE) compared with IDTBR:P3HT and other high performance polymer:fullerene systems. Devices were exposed to ambient conditions over the course of 1200 hours.
- PCE device efficiencies
- Figure 7 shows further exemplary electron acceptor compounds that may be used in devices described herein.
- the terms "donor” or “donating” and “acceptor” or “accepting” will be understood to mean an electron donor or electron acceptor, respectively.
- “Electron donor” will be understood to mean a chemical entity that donates electrons to another compound or another group of atoms of a compound.
- “Electron acceptor” will be understood to mean a chemical entity that accepts electrons transferred to it from another compound or another group of atoms of a compound, (see also U.S.
- any organic electron acceptor compound referenced in any aspect or embodiment of the invention as described herein is preferably a non-fullerene organic electron acceptor compound, i.e. an organic compound comprising no fullerene components.
- An organic electron donor compound referenced in any aspect or embodiment of the invention as described herein is preferably a non-fullerene organic electron donor compound, i.e. an organic compound comprising no fullerene components.
- a composition of the invention does not contain any fullerene components.
- Ternary compositions comprising two electron acceptor compounds enable improved efficiencies due to, for example, providing a broader and/or stronger absorption of the active layer.
- a ternary composition of the invention, or an optical or electronic device comprising a ternary composition of the invention there are a number of considerations to optimise the parameters of the device. This enables the photovoltaic parameters to be improved over those of a binary device.
- the second electron acceptor compound preferably it may be selected such that it has one or more of the following properties:
- the second electron compound may be a compound having energy levels that satisfy the following: a lower electron affinity than the primary acceptor, to facilitate an energy cascade heterojunction leading to larger open circuit voltages than can be obtained with just the first acceptor; an ionisation potential that is not too large to inhibit hole transfer to the electron donor; and a bandgap at a wavelength which can contribute to the cell external quantum efficiency.
- the surface energy of the electron acceptor (either the first electron acceptor or the second electron acceptor) with the lowest ionisation affinity should be in-between that of the electron donor and other electron acceptor.
- Ionisation potential and electron affinity can be obtained by many standard techniques known to a skilled person in the art including, for example, cyclic voltammetry, ultraviolet photoelectron spectroscopy and inverse photoelectron
- Exemplary second electron acceptor compounds are set out in Figure 7.
- n-type or n-type semiconductor will be understood to mean an extrinsic semiconductor in which the conduction electron density is in excess of the mobile hole density
- p-type or p-type semiconductor will be understood to mean an extrinsic semiconductor in which mobile hole density is in excess of the conduction electron density
- conjugated will be understood to mean a compound (for example a small molecule or a polymer) that contains mainly C atoms with sp2- hybridisation (or optionally also sp-hybridisation), and wherein these C atoms may also be replaced by hetero atoms. In the simplest case this is for example a compound with alternating C— C single and double (or triple) bonds, but is also inclusive of compounds with aromatic units like for example 1 ,4-phenylene.
- the term "mainly” in this connection will be understood to mean that a compound with naturally (spontaneously) occurring defects, which may lead to interruption of the conjugation, is still regarded as a conjugated compound.
- conjugation is the interaction of one p-orbital with another across an intervening o-bond in such structures.
- d-orbitals may be involved.
- a conjugated system is a system of connected p-orbitals with delocalized electrons in molecules with alternating single and multiple bonds.
- a conjugated system has a region of overlapping p-orbitals, bridging the adjacent single bonds. They allow a derealization of electrons across all the adjacent aligned p-orbitals.
- the conjugated system may be cyclic, acyclic, linear, branched or mixed.
- a conjugated system according to the present invention is a system which may be partly or completely conjugated.
- asmall molecule may be a compound having a molecular weight of 1000Da or less.
- groups or indices like Cy, Ar, R 1"4 , n etc. in case of multiple occurrences are selected independently from each other and may be identical or different from each other. Thus several different groups may be represented by a single label like
- aliphatic includes both saturated and unsaturated, nonaromatic, straight chain (i.e., unbranched), branched, acyclic, and cyclic (i.e., carbocyclic) hydrocarbons, which are optionally substituted with one or more functional groups.
- aliphatic is intended herein to include, but is not limited to, alkyl, alkenyl, alkynyl, cycloalkyi, cycloalkenyl, and cycloalkynyl moieties containing from 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms.
- Heteroaliphatic is an aliphatic group where one or more carbon atoms are replaced with a heteroatom, such as O, N, S, P etc.
- alkyl', 'aryl', 'heteroaryl' etc also include multivalent species, for example alkylene, arylene, 'heteroarylene' etc.
- carbyl group denotes any monovalent or multivalent organic radical moiety which comprises at least one carbon atom either without any non- carbon atoms (like for example -C ⁇ C-), or optionally combined with at least one non- carbon atom such as N, O, S, P, Si, Se, As, Te or Ge (for example carbonyl etc.).
- hydrocarbyl group denotes a carbyl group that does additionally contain one or more H atoms and optionally contains one or more hetero atoms like for example N, O, S, P, Si, Se, As, Te or Ge.
- a carbyl or hydrocarbyl group comprising a chain of 3 or more C atoms may also be linear, branched and/or cyclic, including spiro and/or fused rings.
- Preferred carbyl and hydrocarbyl groups include alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy, each of which is optionally substituted and has 1 to 40, preferably 1 to 25, more preferably 1 to 20 or 1 to 18 C atoms, and optionally substituted aryl, arylalkyl, alkylaryl, or aryloxy having 5 to 40, preferably 5 to 25 C atoms, alkylaryloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy, each of which is optionally substituted and has 5 to 40, preferably 5 to 25 C atoms.
- the carbyl or hydrocarbyl group may be a saturated or unsaturated acyclic group, or a saturated or unsaturated cyclic group. Unsaturated acyclic or cyclic groups are preferred, especially aryl, alkenyl and alkynyl groups (especially ethynyl). Where the CrC 40 carbyl or hydrocarbyl group is acyclic, the group may be linear or branched.
- the Ci-C 40 carbyl or hydrocarbyl group includes for example: a C C 40 alkyl group, a C 2 - C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 allyl group, a C 4 -C 40 alkyldienyl group, a C 4 -C 40 polyenyl group, a C 6 -Ci 8 aryl group, a C 6 -C 40 alkylaryl group, a C 6 -C 40 arylalkyl group, a C 4 -C 40 cycloalkyl group, a C 4 -C 40 cycloalkenyl group, and the like.
- Preferred among the foregoing groups are a C C 20 alkyl group, a C 2 -C 2 o alkenyl group, a C 2 -C 20 alkynyl group, a C 3 -C 20 allyl group, a C 4 -C 20 alkyldienyl group, a C 5 -Ci 2 aryl group, a C 6 - C 20 arylalkyl group, a 5 to 20 membered heteroaryl and a C 4 -C 20 polyenyl group, respectively.
- groups having carbon atoms and groups having hetero atoms like e.g. an alkynyl group, preferably ethynyl, that is substituted with a silyl group, preferably a trialkylsilyl group.
- carbyl and hydrocarbyl groups include straight-chain, branched or cyclic alkyl with 1 to 40, preferably 1 to 25 C-atoms, which is unsubstituted, mono- or
- Halogen is F, CI, Br or I.
- an alkyl group is a straight chain or branched, cyclic or acyclic, substituted or unsubstituted group containing from 1 to 40 carbon atoms, from 1 to 25 carbon atoms, from 1 to 20 carbon atoms, from 1 to 18 carbon atoms, from 1 to 12 carbon atoms or from 1 to 8 carbon atoms, inclusive.
- An alkyl group may optionally be
- alkyl groups include, without limitation, methyl, ethyl, n-propyl, i-propyl, n-butyl,
- Preferred alkenyl groups include, without limitation, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl etc.
- Preferred alkynyl groups include, without limitation, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl etc.
- Preferred alkoxy groups include, without limitation, methoxy, ethoxy, 2-methoxyethoxy, n- propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n- hexoxy, n-heptoxy, n-octoxy etc.
- Preferred amino groups include, without limitation, dimethylamino, methylamino, methylphenylamino, phenylamino, etc.
- Aromatic rings are cyclic aromatic groups that may have 0, 1 or 2 or more, preferably 0, 1 or 2 ring heteroatoms. Aromatic rings may be optionally substituted and/or may be fused to one or more aromatic or non-aromatic rings, which may contain 0, 1 , 2, or more ring heteroatoms, to form a polycyclic ring system.
- Aromatic rings include both aryl and heteroaryl groups.
- Aryl and heteroaryl groups may be mononuclear, i.e. having only one aromatic ring (like for example phenyl or phenylene), or polynuclear, i.e. having two or more aromatic rings which may be fused (like for example napthyl or naphthylene), individually covalently linked (like for example biphenyl), and/or a combination of both fused and individually linked aromatic rings.
- the aryl or heteroaryl group is an aromatic group which is substantially conjugated over substantially the whole group.
- Aryl groups may contain from 5 to 40 ring carbon atoms, from 5 to 25 carbon atoms, from 5 to 20 carbon atoms, or from 5 to 12 carbon atoms.
- Heteroaryl groups may be from 5 to 40 membered, from 5 to 25 membered, from 5 to 20 membered or from 5 to 12 membered rings, containing 1 or more ring heteroatoms selected from N, O, S and P.
- An aryl or heteroaryl may be fused to one or more aromatic or non-aromatic rings to form a polycyclic ring system.
- Aryl and heteroaryl preferably denote a mono-, bi- or tricyclic aromatic or heteroaromatic group with up to 25 ring atoms that may also comprise condensed rings and is optionally substituted.
- Preferred aryl groups include, without limitation, benzene, biphenylene, triphenylene, [1 ,1 ':3',1 "]terphenyl-2'-ylene, naphthalene, anthracene, binaphthylene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzpyrene, fluorene, indene, indenofluorene, spirobifluorene, etc.
- Preferred heteroaryl groups include, without limitation, 5-membered rings like pyrrole, pyrazole, silole, imidazole, 1 ,2,3-triazole, 1 ,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1 ,2-thiazole, 1 ,3-thiazole, 1 ,2,3-oxadiazole,
- heteroaryl groups may be substituted with alkyl, alkoxy, thioalkyl, fluoro, fluoroalkyl or further aryl or heteroaryl substituents.
- Preferred arylalkyl groups include, without limitation, 2-tolyl, 3-tolyl, 4-tolyl, 2,6- dimethylphenyl, 2,6-diethylphenyl, 2,6-di-i-propylphenyl, 2,6-di-t-butylphenyl, o-t- butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 4-phenoxyphenyl, 4-fluorophenyl, 3- carbomethoxyphenyl, 4-carbomethoxyphenyl etc.
- Preferred alkylaryl groups include, without limitation, benzyl, ethylphenyl, 2-phenoxyethyl, propylphenyl, diphenylmethyl, triphenylmethyl or naphthalinylmethyl.
- Preferred aryloxy groups include, without limitation, phenoxy, naphthoxy, 4- phenylphenoxy, 4-methylphenoxy, biphenyloxy, anthracenyloxy, phenanthrenyloxy etc.
- fused refers to a cyclic group, for example an aryl or heteroaryl group, in which two adjacent ring atoms , together with additional atoms, forms a fused ring to give a polycyclic (for example, a bicyclic) ring system.
- Backbone twisting is also caused by the relatively small amount of quinoidal character of the phenyl-phenyl link. This lack of planarity disrupts the crystal packing of the acceptor, reducing its crystallinity.
- the branched 2-ethylhexyl pendant alkyl chains also are expected to disrupt the crystal packing, relative to the linear n-octyl chains, which would give it a slightly different morphology in blends compared to O-FBR.
- the optoelectronic properties of the acceptor were expected to be very similar to those of O- FBR.
- EH-IDFBR and O-IDFBR were carried out in accordance with Scheme 2.
- the alkylated indenofluorene units were brominated, followed by the formation of the boronic acid pinacol esters according to standard procedures, so that they too could undergo Suzuki cross coupling reactions with the bromo benzothidiazole carboxaldehyde units.
- Indenofluorene has similar sterics to fluorene, and is not so electron rich as to cause significant deboronation, hence it was deemed suitable to use the Suzuki reaction with the same conditions as for the synthesis of EH-FBR and O-FBR.
- flanking 3- ethylrhodanine units were introduced using a Knoevenagel condensation reaction with the aldehyde functionality of the benzothiadiazole units.
- the identities of the products formed were confirmed to be O-IDFBR and EH-IDFBR with the use of 1 H and 13 C NMR along with mass spectrometry.
- the indenofluorene core is larger and more conjugated than fluorene; hence the IDFBR acceptors were designed to be slightly more crystalline than their fluorene counterparts. This is due to increased ⁇ - ⁇ stacking of the larger, more conjugated indenofluorene core Again, the phenyl-phenyl link should lead to backbone twisting in order to avoid the steric clash of ortho hydrogens.
- the reduced quinoidal character is also likely to contribute to this reduced planarity, which would limit the crystallinity of the acceptors to some degree.
- the acceptor bearing the branched 2-ethylhexyl alkyl side chains was expected to be more amorphous than the acceptor with the linear n-octyl chains for crystal packing reasons. Despite the slightly more crystalline order expected in these acceptors, they still exhibit good solubility in common organic solvents, hence are suitable for solution processing.
- the more conjugated indenofluorene core was also expected to raise the HOMO level slightly, whilst having little effect on the LUMO, relative to the FBR acceptors.
- the HOMO is expected to be delocalized across the entire molecule, as discussed for O-FBR; hence increasing the conjugation of the aromatic core will raise the HOMO.
- the LUMO is expected to be localized onto the electron deficient periphery of the molecule
- Compound 1 was prepared according to the methods set out in Zhang, W. et al., J Am Chem Soc 131 , 10814-10815, (2009) and Setayesh, S. et al., Macromolecules 33, 2016- 2020, (2000), the contents of which are herein incorporated by reference in their entirety.
- the indacenodithiophene core contains a thiophene-like moiety at either end of the unit; hence the IDTBR acceptors contain a thiophene-phenyl link rather than the phenyl-phenyl link in the FBR acceptors.
- This link leads to far less steric repulsion of ortho protons than its phenyl-phenyl counterpart, hence these acceptors are expected to have a much more planar structure.
- the thiophene-phenyl link has more quinoidal character than a phenyl-phenyl link, which further enhances the planarity of the molecule.
- the enhanced planarity of the IDTBR acceptors would allow much greater conjugation throughout the molecules.
- the bandgap of these acceptors is expected to be much narrower than for the FBR and IDFBR acceptors. This would red shift the absorption profile further, leading to an even larger fraction of the solar spectrum being utilized in devices with P3HT.
- O-GelDTBR was synthesised according to scheme 4 and the experimental procedures below.
- compound 3 (3 g, 4.27 mmol) was dissolved in 60 mL of anhydrous THF and cooled to -90°C.
- a second dry three-necked round bottom flask were introduced 30 mL of anhydrous THF, which were cooled down to -90°C before a 1.7 M solution of te/f-butyllithium (20.7 mL, 35.11 mmol) in pentane was added.
- the solution containing compound 3 was added dropwise to the f-butyllithium solution, whilst maintaining the temperature below -85°C. After complete addition, the resulting dark brown solution was stirred during one hour at -90°C.
- Tris(dibenzylideneacetone)dipalladiumO (0.0158 g, 0.0172 mmol) and tri(o-tolyl)phosphine (0.0105 g, 0.0345 mmol) were added to the solution before degassing for a further 30 mins.
- Degassed 2M sodium carbonate solution (1.38 mL, 2.758 mmol) was then added and the reaction was heated to 110 °C with stirring overnight, under an inert argon atmosphere. The mixture was then poured into H 2 0, extracted with CH 2 CI 2 , and the organic phase was washed with H 2 0 and brine, before drying over anhydrous magnesium sulphate.
- EH-NIDTBR was synthesised according to scheme 5 and the experimental procedures below.
- N 2 ,N 2 ,N 6 ,N 6 -tetraethyl-3,7-dihydroxynaphthalene-2,6-dicarboxamide (1 equiv.) were dissolved in DMF and imidazole (3.5 equiv.) was added. Then, TBSCI (3 equiv.) was added portionwise and the reaction mixture stirred at room temperature for 24 h. The reaction was quenched by pouring into water and the resulting white precipitate was filtered off, washed with copious amounts of water, and dried in vacuum. The crude product was dissolved in anhydrous DCM and (CH 3 ) 3 OBF 4 (2.4 equiv.) was added in portions.
- the reaction mixture was evaporated to dryness and methanol was added followed by a saturated solution of Na 2 C0 3 and solid Na 2 C0 3 .
- the resulting mixture was filtered and acidified with HCI to a pH of 1.
- the formed solid was recovered by filtration as a first fraction, which could be used without further purification (34%).
- the organic layer was dried, evaporated and purified by silica gel filtration (chloroform as eluent) to yield a second fraction 49% yield was obtained in total.
- the resulting brown solution was extracted with dichloromethane (three times) and the organic layer was dried over magnesium sulfate and evaporated to dryness.
- the received brown oil was purified by column chromatography on silica, eluting with hexanes, to give a colourless oil (10%).
- Tris(dibenzylideneacetone)dipalladiumO (0.05 equiv.) and tri(o-tolyl)phosphine (0.1 equiv.) were added to the solution before degassing for a further 30 mins.
- Degassed 2M sodium carbonate solution (8 equiv.) was then added and the reaction was heated to 110 °C with stirring overnight, under an inert argon atmosphere. The mixture was then poured into H 2 0, extracted with CH 2 CI 2 , and the organic phase was washed with H 2 0 and brine, before drying over anhydrous magnesium sulphate.
- the resulting solid was purified by column chromatography over silica using CH 2 CI 2 , and precipitated out from CH 2 CI 2 / methanol to yield 15.
- O-GeNIDTBR was synthesised according to scheme 6 and the experimental procedures below.
- NIDFBR may be synthesised according to scheme 7, below.
- Figure 2a shows the absorption spectra of P3HT, IDFBR and IDTBR.
- the absorption profiles of both acceptors are quite different, depending on the structure of the middle core.
- reduced steric twisting from adjacent alpha C-H bonds on the coupled phenyl rings and increased quinoidal character of the phenyl-thienyl bond in IDTBR leads to enhanced planarity and more electron-rich thiophene-based core of IDTBR acts to raise the highest occupied molecular orbital (HOMO), leading to a significantly red-shifted UV-vis absorption spectrum relative to that of IDFBR.
- HOMO occupied molecular orbital
- the photovoltaic performances of the binary P3HT: IDTBR and ternary blends are measured with a device architecture comprising: indium tin oxide (ITO)/ zinc oxide (ZnO)/active layer (90 ⁇ 5 nm) /molybdenum oxide (Mo0 3 )/Ag, where the active layer consists of binary P3HT:electron acceptor compound or ternary P3HT:IDTBR:second electron acceptor compound blends.
- the active layer blends were spin-coated from chlorobenzene solution under ambient conditions without the use of additives. Thermal annealing (10 min at 130 °C) was carried out to promote ordering of the polymer, as is typical in P3HT solar cells, as well as to induce acceptor crystallisation.
- the weight ratio of IDFBR in IDTBR was changed from 10-70%. In all cases, the active layers were spin coated from chlorobenzene (CB) under ambient conditions and for all acceptor ratios; the weight ratio of acceptor to P3HT was kept at 1 : 1.
- Figure 3 shows the JV and EQE Spectra of binary and ternary blends under simulated AM 1.5 G illuminations at l OOmWcm "2 .
- the P3HT:IDTBR device exhibits a J sc and FF of 13.9 mA/cm 2 and 0.60, respectively and a relatively high V ⁇ of 0.73 V for P3HT based solar cells (0.58V for P3HT:60PCBM) (Table S3) which results in a PCE of 6.3%.
- 30% (with respect to IDTBR) 60PCBM into the P3HT:IDTBR (1 :0.7) blend, all J sc , V ⁇ and FF values substantially decrease with an overall efficiency of 3.6 % mainly due to reduced V ⁇ (0.59V) and low FF values around 0.5 compared to binary devices.
- the third component is selected to be IDFBR.
- the optimized P3HT:IDFBR reference binary devices are achieved with 1 :1 (w:w) ratio in the same solvent as P3HT:IDTBR system (CB) with a remarkably high V ⁇ and FF values up to 0.88V and 0.64, respectively, with an overall efficiency of 4.5%.
- the small amount (10% by weight) addition of IDFBR as third component into P3HT:IDTBR binary blend increased both J sc and V oc in the ternary blend with a slightly lower FF values.
- P3HT:IDTBR: IDFBR (100:70:30) devices exhibit a J sc of 14.4 mAcm "2 and a 100 meV higher V ⁇ than the binary P3HT:IDTBR blend of 0.82V and relatively high FF of 0.64 with a remarkable power conversion efficiency of 7.7% which means an average of over 20% PCE improvement compared to binary P3HT:IDTBR devices.
- Further addition (above 30%) of IDFBR did not further increase the V oc or FF values (up to 70%) but decreased the Jsc mainly due to diluted IDTBR amount in the ternary blend, and subsequently lower photocurrent generation.
- P3HT:IDTBR:IDFBR devices retain the high FF values (65%) with slightly lower V oc and J sc (0.78 V and 11.3 mAcm "2 ) with an overall efficiency of 5.7% even at high thicknesses (-200 nm). Furthermore, larger area
- P3HT:IDTBR:IDFBR devices ( ⁇ 1 cm 2 ) were also successfully demonstrated with efficiencies as high as 6.5%, with the slightly lower efficiencies attributed to the lower FF.
- the heat flow profiles reveal that both the IDFBR and IDTBR binary blends with P3HT exhibits broad endothermic transitions at temperatures above 200 °C, attributed to a P3HT crystalline phase melt.
- the melting transition of P3HT is significantly broadened and supressed in all blends.
- the P3HT melting transition enthalpy for the IDFBR binary blend is also reduced by a factor of 5, whereas it is only slightly lower than the pristine P3HT in the case of the IDTBR blend. This difference indicates that both small molecules can diffuse into the P3HT phases, being more prominent for IDFBR leading to extensive disorder in the polymer.
- the endotherm is prominent, although its peak has broadened, and there is a reduction in melting temperature and melting enthalpy.
- the P3HT crystalline phase still persists, with a broad melt endotherm.
- the P3HT melting point and melting enthalpies in the ternaries are intermediate between those of the respective binaries.
- the IDTBR crystalline transition in the ternary blends exhibits a melting point depression and lower enthalpy in comparison to the IDTBR binary film, indicating that the IDFBR has been able to also diffuse into the IDTBR phase. No evidence of any IDFBR thermal transitions is present.
- a cooling scan shows a strongly super-cooled
- the ternary film therefore, can be described as having three partially miscible components, comprising of a crystalline P3HT phase, which also hosts a molecular dispersion of both IDFBR and IDFBR molecules, as well as an IDTBR rich crystalline phase that also contains IDFBR. There is also likely to be a disordered phase containing a molecularly dissolved mix of the three components.
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GBGB1607942.8A GB201607942D0 (en) | 2016-05-06 | 2016-05-06 | Electron acceptor compounds |
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EP3306690B1 (en) | 2016-10-05 | 2022-09-07 | Raynergy Tek Inc. | Organic semiconducting compounds |
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KR102091018B1 (en) * | 2017-11-30 | 2020-03-19 | 경상대학교산학협력단 | Novel compound and organic electronic device using them |
KR102114485B1 (en) * | 2018-03-16 | 2020-05-22 | 이화여자대학교 산학협력단 | Organic semiconductor compound and electronic device using the same |
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CN109824703B (en) * | 2019-02-28 | 2020-05-05 | 山东师范大学 | Organic compound with non-planar core structure and preparation method and application thereof |
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US20230143779A1 (en) * | 2020-02-13 | 2023-05-11 | Koala Tech Inc. | Organic solid-state laser, compound and use thereof |
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