JP3204770U - 有機太陽電池 - Google Patents
有機太陽電池 Download PDFInfo
- Publication number
- JP3204770U JP3204770U JP2016001517U JP2016001517U JP3204770U JP 3204770 U JP3204770 U JP 3204770U JP 2016001517 U JP2016001517 U JP 2016001517U JP 2016001517 U JP2016001517 U JP 2016001517U JP 3204770 U JP3204770 U JP 3204770U
- Authority
- JP
- Japan
- Prior art keywords
- layer
- solar cell
- electron transport
- organic solar
- donor
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000004065 semiconductor Substances 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000010248 power generation Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 139
- 239000000463 material Substances 0.000 description 43
- 239000002800 charge carrier Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 16
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class 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 9
- 238000000151 deposition Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 5
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229910003472 fullerene Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003384 small molecules Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 2
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011358 absorbing material Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- DXUUXWKFVDVHIK-UHFFFAOYSA-N ambenonium chloride Chemical group [Cl-].[Cl-].C=1C=CC=C(Cl)C=1C[N+](CC)(CC)CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl DXUUXWKFVDVHIK-UHFFFAOYSA-N 0.000 description 2
- -1 anthracyl Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- HSMDIUMGCHZHNI-UHFFFAOYSA-N st51028380 Chemical compound C12=CC=CC=C2C(=O)C2=C1C(C(=O)C1=CC=CC=C11)=C1C1=C2C2=CC=CC=C2C1=O HSMDIUMGCHZHNI-UHFFFAOYSA-N 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 description 1
- FNDNINXBCCPYRA-UHFFFAOYSA-N 2-(1,3-dimethyl-2-propan-2-yl-4,5,6,7-tetrahydrobenzimidazol-2-yl)-1,3-dimethyl-2-propan-2-yl-4,5,6,7-tetrahydrobenzimidazole Chemical compound CN1C(CCCC2)=C2N(C)C1(C(C)C)C(N1C)(C(C)C)N(C)C2=C1CCCC2 FNDNINXBCCPYRA-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- BCEFWDSXZPDOOB-UHFFFAOYSA-J [W+2].[W+2].N1C=2N(CCC1C(=O)[O-])CCCN2.N2C=1N(CCC2C(=O)[O-])CCCN1.N1C=2N(CCC1C(=O)[O-])CCCN2.N2C=1N(CCC2C(=O)[O-])CCCN1 Chemical compound [W+2].[W+2].N1C=2N(CCC1C(=O)[O-])CCCN2.N2C=1N(CCC2C(=O)[O-])CCCN1.N1C=2N(CCC1C(=O)[O-])CCCN2.N2C=1N(CCC2C(=O)[O-])CCCN1 BCEFWDSXZPDOOB-UHFFFAOYSA-J 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical compound C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Images
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- H10K85/611—Charge transfer complexes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K30/211—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions comprising multiple junctions, e.g. double heterojunctions
-
- 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
- H10K30/353—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 comprising blocking layers, e.g. exciton blocking layers
-
- 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
- H10K30/57—Photovoltaic [PV] devices comprising multiple junctions, e.g. tandem PV cells
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Nanotechnology (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electromagnetism (AREA)
- Photovoltaic Devices (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本考案は、有機太陽電池としても知られる有機光電変換(OPV)素子に関する。
OPV素子は、最も様々な素子構造を有している。一般的に、OPV素子は、二つの電極の間に少なくとも一つの有機半導体層を含む。その有機層は、供与体と受容体との混合物(例えば、P3HT(ポリ3−ヘキシル−チオフェン)およびPCBM(フェニルCn酪酸メチルエステル)など)とすることができる。このような簡単な素子構造は、界面注入層(interfacial injection layers)が、電荷担体の注入/抽出を円滑に行うために用いられる場合、効率を合理的に達成するだけである(Liao et al., Appl. Phys. Lett., 2008. 92: p. 173303)。他の有機太陽電池は、多層構造を有しており、中にはハイブリッド高分子構造および小分子構造を有するものもある。また、タンデム型または複数ユニット型の堆積もまた知られている(Ameri, et al., Energy & Env. Science, 2009. 2: p. 347)。それぞれの層が、それぞれ異なる機能を行うのに好適な異なる材料を含むことができるため、多層素子をより簡単に最適化することができる。典型的な機能層は、輸送層、光学活性層、注入層などがある。
本考案の目的は、有機太陽電池に用いるための新たな有機半導体材料を提供することである。上記材料は、好ましくは、光学活性層の少なくとも一つおよび電子輸送層に用いられ、より好ましくは電子輸送層に用いられる。
この目的は、式(I)によって表される新たな化合物によって実現できる。この目的はまた、独立請求項1によって、ならびに従属請求項の考案される好ましい用途および素子によって実現できる。この目的は、下記式(I)によって表される化合物を少なくとも一つ含んでいる有機太陽電池によって実現できる:
R1およびR2は、それぞれ独立して、CN、アリール、アルキル、NO2、ハロゲン、ヘテロアリール、CF3から選択され、ここでアリールは置換されることができ、
A1、A2、A3、A4は、それぞれ独立してC、CH、N、CRから選択され、またはA1−A2、A2−A3、A3−A4の少なくとも一つが付加縮合された芳香環の一部であり、上記付加縮合された芳香環(additional aromatic condensed ring)は、好ましくは、フェニル、ピラジル、チエニル、イミダゾイル、ヘテロアリールであり、
Rは芳香環、好ましくは、以下に定義されているアリールである。
式(I)によって表される化合物は、好ましくは太陽電池における電子輸送層に用いられる。上記化合物は、電子輸送層の主成分である。好ましくは、式(I)によって表される化合物を含んでいる電子輸送層の少なくとも一つは、電気的なドーパントがドーピングされている。
図1は、太陽電池を形成する層の堆積を表している略図である。
図1によると、有機太陽電池は、基板(10)、陽極(11)、少なくとも一つの有機光学活性層(12)、および、陰極(13)を少なくとも含む。また、上記積層が逆型となることができ、その場合、層(11)が陰極となり、層(12)が陽極となる。
下記の式は、本考案における化合物の一般的な合成を示す。
[実施例C−2]
第1ステップ:5H−ジインデノ[1,2−a:1’,2’−c]フルオレン−5,10,15−トリオン(1)の合成。全ての操作を、市販の溶液/化学薬品をそれ以上精製せずに、大気中にて行った。
第1ステップ:5H−ジインデノ[1,2−a:1’,2’−c]フルオレン−5,10,15−トリオン(1)の合成。全ての操作を、市販の溶液/化学薬品をそれ以上精製せずに、大気中にて行った。
その後、上記混合物を室温まで冷却し、氷水500mLに注ぎ、ジクロロメタンを用いて抽出した。次いで、ロータリー・エバポレータを用いて上記溶媒を除去した。得られたオイルを、ジエチルエーテル(100mL)を用いて処理した。その懸濁液を濾過し、ジクロロメタンを除去した後、シリカパッドを通して(ジクロロメタンで)ゲル濾過し、橙色の固体を得た。
素子1(比較例)。最新技術の有機太陽電池を、以下の手順で製造することができる:ITOでコーティングされた、パターニングされたガラス基板を、エタノール、アセトン、およびイソプロパノールを含んでいる超音波洗浄機中にて洗浄する。その後、上記ITO基板を、15分間酸素プラズマ処理にさらす。上記基板を、窒素を含んでいるグローブボックスに通して真空中に入れる。真空において、従来のVTE(真空熱蒸着)を用いて上記有機層を蒸着する。まず、厚さ10nmの5%(モル濃度)のp−ドーピングされているCuPc層を、シャドーマスクを通して上記ITO上に蒸着する。10nmの非ドーピングのCuPc層を上記ドーピングされているCuPc層上に蒸着する。厚さ30nmのフラーレンC60とCuPcとの混合層を、モル比2(C60):1(CuPc)にて蒸着する。厚さ40nmのC60層を、上記混合層の上に蒸着する。10nmのBPhen(4,7−ジフェニル−1,10−フェナントロリン)層を、上記C60層の上に蒸着する。上記BPhen層に続けて、厚さ100nmのAl陰極を蒸着する。標準疑似AM1.5(気団1.5)太陽スペクトル下にて、このような素子は、一般的に、約8mA/cm2の短絡電流、約40%のFF、および約0.5Vの開路電圧を示す。
逆型(Inverted)−用語「逆型太陽電池」、または、「逆型構造」は、陰極が陽極よりも基板に近い層構造を有する素子をいう。逆型素子の製造方法において、上記陰極は、基板上に形成され、その後、陰極の蒸着に続けて有機層および他の層の蒸着が行われる。
Claims (9)
- 請求項1に記載の式(I)によって表される化合物を少なくとも一つ含んでいる上記層は、第一の電子輸送層および/または供与体−受容体のヘテロ接合である、請求項1に記載の有機太陽電池。
- 上記第一の電子輸送層が、ドーピングされている、請求項2に記載の有機太陽電池。
- 補助的な電子輸送層を含んでおり、上記補助的な電子輸送層はドーピングされておらず、ここで上記補助的な電子輸送層は上記供与体−受容体のヘテロ接合と隣接しており、上記第一の電子輸送層は上記補助的な電子輸送層と陰極との間に位置する、請求項2または3に記載の有機太陽電池。
- 上記補助的な電子輸送層は、正孔ブロッキング層および励起子ブロッキング層の少なくとも一つである、請求項4に記載の有機太陽電池。
- 上記供与体−受容体のヘテロ接合が、受容体として、請求項1に記載の式(I)によって表される化合物を含む、請求項2〜5のいずれか一項に記載の有機太陽電池。
- 上記供与体−受容体のヘテロ接合はバルク−ヘテロ接合である、請求項6に記載の有機太陽電池。
- 少なくとも一つの半導体高分子層を含んでいる、請求項2に記載の有機太陽電池。
- 上記第一の電子輸送層がn−ドーピングされている、請求項8に記載の有機太陽電池。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10400044.3 | 2010-09-10 | ||
EP10400044 | 2010-09-10 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013527489A Continuation JP2013541837A (ja) | 2010-09-10 | 2011-09-05 | 有機光電変換素子用化合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP3204770U true JP3204770U (ja) | 2016-06-16 |
Family
ID=44582872
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013527489A Pending JP2013541837A (ja) | 2010-09-10 | 2011-09-05 | 有機光電変換素子用化合物 |
JP2016001517U Expired - Lifetime JP3204770U (ja) | 2010-09-10 | 2016-04-01 | 有機太陽電池 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013527489A Pending JP2013541837A (ja) | 2010-09-10 | 2011-09-05 | 有機光電変換素子用化合物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20140144509A1 (ja) |
EP (1) | EP2614047B8 (ja) |
JP (2) | JP2013541837A (ja) |
CN (1) | CN103180289B (ja) |
WO (1) | WO2012031735A1 (ja) |
Families Citing this family (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101434658B1 (ko) * | 2011-12-28 | 2014-08-29 | 코오롱인더스트리 주식회사 | 유기 태양전지의 제조 방법 |
DE102013013876A1 (de) | 2013-08-20 | 2015-03-12 | Merck Patent Gmbh | Metallkomplexe |
EP3077382B1 (de) | 2013-12-06 | 2018-12-26 | Merck Patent GmbH | Substituierte oxepine |
JP6542228B2 (ja) | 2013-12-19 | 2019-07-10 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 複素環式スピロ化合物 |
KR101678580B1 (ko) * | 2014-07-03 | 2016-11-22 | 부산대학교 산학협력단 | 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기 전자 소자 및 유기 태양전지 소자 |
WO2016012075A1 (de) | 2014-07-21 | 2016-01-28 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
JP6695863B2 (ja) | 2014-09-05 | 2020-05-20 | メルク パテント ゲーエムベーハー | 調合物と電子素子 |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
JP6004293B2 (ja) * | 2015-01-19 | 2016-10-05 | 奥本 健二 | トルクセン誘導体およびそれを用いる有機半導体デバイス |
JP6800879B2 (ja) | 2015-03-30 | 2020-12-16 | メルク パテント ゲーエムベーハー | シロキサン溶媒を含む有機機能性材料の調合物 |
US10808170B2 (en) | 2015-06-12 | 2020-10-20 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for OLED formulations |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
KR20180090362A (ko) | 2015-12-10 | 2018-08-10 | 메르크 파텐트 게엠베하 | 비-방향족 사이클을 함유하는 케톤을 포함하는 제형 |
EP3391428B1 (en) | 2015-12-15 | 2022-06-29 | Merck Patent GmbH | Esters containing aromatic groups as solvents for organic electronic formulations |
KR20180095028A (ko) | 2015-12-16 | 2018-08-24 | 메르크 파텐트 게엠베하 | 둘 이상의 상이한 용매의 혼합물을 함유하는 제형 |
KR20180096676A (ko) | 2015-12-16 | 2018-08-29 | 메르크 파텐트 게엠베하 | 고체 용매를 함유하는 제형 |
EP3417033B1 (en) | 2016-02-17 | 2021-02-24 | Merck Patent GmbH | Formulation of an organic functional material |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
KR20190019138A (ko) | 2016-06-16 | 2019-02-26 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
US11041083B2 (en) | 2016-06-17 | 2021-06-22 | Merck Patent Gmbh | Formulation of an organic functional material |
TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
KR102427363B1 (ko) | 2016-08-04 | 2022-07-29 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
CN109863223B (zh) | 2016-10-31 | 2023-06-20 | 默克专利有限公司 | 有机功能材料的制剂 |
JP7013459B2 (ja) | 2016-10-31 | 2022-01-31 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
KR102472751B1 (ko) | 2016-12-06 | 2022-11-30 | 메르크 파텐트 게엠베하 | 전자 디바이스의 제조 방법 |
KR102486614B1 (ko) | 2016-12-13 | 2023-01-09 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光(el)元件之方法 |
TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
CN110446611B (zh) | 2017-03-31 | 2021-05-25 | 默克专利有限公司 | 用于有机发光二极管(oled)的印刷方法 |
CN110494514A (zh) | 2017-04-10 | 2019-11-22 | 默克专利有限公司 | 有机功能材料的制剂 |
JP2020522876A (ja) | 2017-04-13 | 2020-07-30 | メルク パテント ゲーエムベーハー | 有機電子デバイス用組成物 |
CN110573515B (zh) | 2017-04-25 | 2023-07-25 | 默克专利有限公司 | 用于电子器件的化合物 |
CN110546236A (zh) | 2017-05-03 | 2019-12-06 | 默克专利有限公司 | 有机功能材料的制剂 |
CN107253950B (zh) * | 2017-05-17 | 2019-12-10 | 上海天马有机发光显示技术有限公司 | 一种化合物及制备方法、一种有机发光显示装置 |
WO2018234346A1 (en) * | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
EP3645766A1 (en) | 2017-06-26 | 2020-05-06 | Merck Patent GmbH | Homogeneous mixtures |
WO2019007867A1 (de) | 2017-07-05 | 2019-01-10 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
US11591320B2 (en) | 2017-07-05 | 2023-02-28 | Merck Patent Gmbh | Composition for organic electronic devices |
KR20200030573A (ko) | 2017-07-18 | 2020-03-20 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
US11839147B2 (en) * | 2017-09-04 | 2023-12-05 | Beijing Summer Sprout Technology Co., Ltd. | Hole injection layer and charge generation layer containing a truxene based compound |
TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
JP7247231B2 (ja) | 2018-02-26 | 2023-03-28 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
EP3802520A1 (de) | 2018-05-30 | 2021-04-14 | Merck Patent GmbH | Zusammensetzung für organische elektronische vorrichtungen |
JP7379389B2 (ja) | 2018-06-15 | 2023-11-14 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
KR20210056432A (ko) | 2018-09-24 | 2021-05-18 | 메르크 파텐트 게엠베하 | 과립형 재료의 제조 방법 |
TW202034551A (zh) | 2018-11-06 | 2020-09-16 | 德商麥克專利有限公司 | 用於形成電子裝置的有機元件之方法 |
JP6962947B2 (ja) * | 2019-02-22 | 2021-11-05 | 株式会社東芝 | 放射線検出器 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
CN115867426A (zh) | 2020-06-23 | 2023-03-28 | 默克专利有限公司 | 生产混合物的方法 |
WO2022098917A1 (en) * | 2020-11-04 | 2022-05-12 | Ubiquitous Energy, Inc. | Photoactive compounds for vapor deposited organic photovoltaic devices |
WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
KR20240000559A (ko) | 2021-04-23 | 2024-01-02 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 포뮬레이션 |
WO2022243403A1 (de) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
TW202349760A (zh) | 2021-10-05 | 2023-12-16 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
WO2024094566A1 (en) | 2022-10-31 | 2024-05-10 | Credoxys GmbH | Indacene and azaindacene compounds and higher homologues and the use thereof |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4445584A1 (de) * | 1994-12-20 | 1996-06-27 | Basf Ag | Verwendung von organischen Materialien hoher nichtionischer Ladungsträgerbeweglichkeit |
JP4240841B2 (ja) * | 2001-04-27 | 2009-03-18 | キヤノン株式会社 | 有機発光素子 |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
DE102004010954A1 (de) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
FR2869318B1 (fr) * | 2004-04-21 | 2006-06-09 | Commissariat Energie Atomique | Composes mono-,oligo et polymeres pi -conjugues, et cellules photovoltaiques les contenant |
EP1837926B1 (de) | 2006-03-21 | 2008-05-07 | Novaled AG | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
JP2008068804A (ja) * | 2006-09-15 | 2008-03-27 | Toyota Motor Corp | 透明外装部品 |
JP2008268804A (ja) * | 2007-04-25 | 2008-11-06 | Kyocera Mita Corp | 電子写真感光体 |
US8317953B2 (en) * | 2008-05-16 | 2012-11-27 | Digital Solid State Propulsion, Llc | Family of metastable intermolecular composites utilizing energetic liquid oxidizers with nanoparticle fuels in sol-gel polymer network |
JP5785090B2 (ja) * | 2008-11-19 | 2015-09-24 | ノヴァレッド・アクチエンゲゼルシャフト | キノキサリン化合物及び半導体材料 |
US8313671B2 (en) * | 2008-11-21 | 2012-11-20 | Hiroshima University | Heterocyclic compound and use thereof |
US20110308592A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Use of substituted perylenes in organic solar cells |
-
2011
- 2011-09-05 JP JP2013527489A patent/JP2013541837A/ja active Pending
- 2011-09-05 US US13/819,152 patent/US20140144509A1/en not_active Abandoned
- 2011-09-05 EP EP11752493.4A patent/EP2614047B8/en active Active
- 2011-09-05 CN CN201180043303.6A patent/CN103180289B/zh active Active
- 2011-09-05 WO PCT/EP2011/004468 patent/WO2012031735A1/en active Application Filing
-
2016
- 2016-04-01 JP JP2016001517U patent/JP3204770U/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN103180289A (zh) | 2013-06-26 |
CN103180289B (zh) | 2016-03-02 |
EP2614047B8 (en) | 2016-12-14 |
EP2614047B1 (en) | 2016-10-26 |
JP2013541837A (ja) | 2013-11-14 |
EP2614047A1 (en) | 2013-07-17 |
US20140144509A1 (en) | 2014-05-29 |
WO2012031735A1 (en) | 2012-03-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3204770U (ja) | 有機太陽電池 | |
Calió et al. | Vacuum deposited perovskite solar cells employing dopant-free triazatruxene as the hole transport material | |
JP2014520394A (ja) | 有機電子素子のための化合物 | |
JP2022116248A (ja) | 化合物 | |
JP6542217B2 (ja) | ヘテロ接合型有機太陽電池用の新規吸収体 | |
CA2588113C (en) | Organic photosensitive optoelectronic device having a phenanthroline exciton blocking layer | |
JP2014510804A (ja) | アリールスクアラインからなる有機感光デバイスとその製造方法 | |
KR102079941B1 (ko) | 스피로비플루오렌 화합물 및 이를 포함하는 페로브스카이트 태양전지 | |
KR102028331B1 (ko) | 페로브스카이트 태양전지 | |
KR20150038353A (ko) | 전극 버퍼층을 갖는 유기 광전자 소자 | |
WO2013035303A1 (ja) | 有機薄膜太陽電池材料 | |
Sun et al. | High-efficiency planar pin perovskite solar cells based on dopant-free dibenzo [b, d] furan-centred linear hole transporting material | |
KR20150037974A (ko) | 용액 및 진공 침착된 활성층을 포함하는 다중접합 유기 광전변환 소자 | |
JP5106361B2 (ja) | ベンゾホスホール化合物を用いた有機光電変換素子 | |
JP2008091380A (ja) | 有機光電変換素子 | |
JP5658937B2 (ja) | インデノペリレン化合物及びそれを用いた有機薄膜太陽電池 | |
JP2011176233A (ja) | 有機光電変換素子 | |
AU2011218750A1 (en) | Organic photosensitive optoelectronic device having a phenanthroline exciton blocking layer |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7426 Effective date: 20160414 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20160414 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 3204770 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |