EP1817804A2 - Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol - Google Patents
Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiolInfo
- Publication number
- EP1817804A2 EP1817804A2 EP05823798A EP05823798A EP1817804A2 EP 1817804 A2 EP1817804 A2 EP 1817804A2 EP 05823798 A EP05823798 A EP 05823798A EP 05823798 A EP05823798 A EP 05823798A EP 1817804 A2 EP1817804 A2 EP 1817804A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- general formula
- radical
- chain
- alkyl
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 35
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title description 3
- 150000003007 phosphonic acid derivatives Chemical class 0.000 title description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000003573 thiols Chemical class 0.000 claims abstract description 14
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 13
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 239000013545 self-assembled monolayer Substances 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 19
- 239000002094 self assembled monolayer Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000011669 selenium Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract description 10
- 150000001336 alkenes Chemical class 0.000 abstract 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 abstract 1
- 230000036571 hydration Effects 0.000 abstract 1
- 238000006703 hydration reaction Methods 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002356 single layer Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 23
- 239000010931 gold Substances 0.000 description 18
- 229910052737 gold Inorganic materials 0.000 description 17
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000011368 organic material Substances 0.000 description 10
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 10
- 230000005669 field effect Effects 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 238000004377 microelectronic Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- -1 lithium aluminum hydride Chemical compound 0.000 description 7
- 238000004806 packaging method and process Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 150000003009 phosphonic acids Chemical class 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 238000004896 high resolution mass spectrometry Methods 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 150000007970 thio esters Chemical class 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CJWZIIKGQGCMIU-UHFFFAOYSA-N 18-phenoxyoctadecane-1-thiol Chemical compound SCCCCCCCCCCCCCCCCCCOC1=CC=CC=C1 CJWZIIKGQGCMIU-UHFFFAOYSA-N 0.000 description 2
- JEKCXXJDFIQLIU-UHFFFAOYSA-N 18-phenoxyoctadecylphosphonic acid Chemical compound OP(O)(=O)CCCCCCCCCCCCCCCCCCOC1=CC=CC=C1 JEKCXXJDFIQLIU-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WEQRTSIIRDGIFN-UHFFFAOYSA-N octadec-17-enoxybenzene Chemical compound C=CCCCCCCCCCCCCCCCCOC1=CC=CC=C1 WEQRTSIIRDGIFN-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
- DLQDGVZAEYZNTG-UHFFFAOYSA-N dimethyl hydrogen phosphite Chemical compound COP(O)OC DLQDGVZAEYZNTG-UHFFFAOYSA-N 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000001883 metal evaporation Methods 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- FTMKAMVLFVRZQX-UHFFFAOYSA-N octadecylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCP(O)(O)=O FTMKAMVLFVRZQX-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K3/00—Circuits for generating electric pulses; Monostable, bistable or multistable circuits
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K17/00—Electronic switching or gating, i.e. not by contact-making and –breaking
Definitions
- the present invention relates to two new processes for preparing low molecular weight organic compounds which can be used in the field of microelectronics, in particular in the field of polymer electronics, in electronic components, such as organic field effect transistors (OFETs), for the production of thin dielectric layers.
- the organic compounds can be applied to a suitable substrate in the form of a self-assembled monolayer (SAM).
- SAM self-assembled monolayer
- Microelectronics was based only a few years ago on the use of inorganic semiconductors, such as silicon or gallium arsenide. These inorganic materials necessitate expensive and costly processes for the production of structured electronic components containing them. This had, among other things means that microelectronics was essentially limited to the manufacture navalwer ⁇ tiger products. In recent years, a large number of new electronic applications have been proposed which, on the one hand, should make use of the technical achievements of silicon-based microelectronics, but on the other hand are intended for mass production.
- Examples of such mass products are large active matrix screens, which are increasingly the established tubes ⁇ to replace equipment, or RFID systems (abbr. For "rapid dio frequency identification "), which are used for the active identification and identification of goods and merchandise.
- Active matrix displays such as TFT LC displays, typically include field effect transistors based on amorphous or polycrystalline silicon layers. For the production of these high-quality transistors temperatures are necessary, which are usually above 250 ° C. Such high temperatures necessitate the use of rigid and fragile glass or quartz substrates.
- Transponders as used in RFID technology, are usually produced using integrated circuits based on monocrystalline silicon. This leads u.a. at considerable cost in the assembly and connection technology. Passive RF-ID systems draw their energy from the radiated alternating field. The maximum permissible distance between the reader and the transponder for the reading process depends on the radiated power of the reader and the energy consumption of the transponder. Silicon-based transponders therefore operate at supply voltages of 3 V. Products containing a silicon-based chip are too expensive for many applications. Therefore, for example, silicon-based identification tags are used for the
- Examples of microelectronic components based on organic components are the organic field effect Transistors (abbr .: "OFETs”) in z. B. bottom-gate bottom-contact architecture.
- the gate electrode is deposited on a substrate in the first step, after which the gate dielectric (ie the insulator layer) is applied.
- the next step is the deposition and patterning of the source and drain electrodes.
- the semiconductor is deposited between the source and drain electrodes on the gate dielectric.
- the last layer is followed by the deposition of a passivation layer.
- Such a transistor is referred to as OFET, if at least the active semiconductor layer consists of an organic semiconductor.
- the aim is to produce OFETs in which further layers, such as the substrate and / or the gate dielectric, consist of organic materials with tailor-made properties.
- the basic structure of an OFET or polymer transistor with "bottom-gate" structure is shown in FIG.
- OFETs can be used for the fabrication of transistors and integrated circuits over large active areas, e.g. B. as pixel controls in the above-mentioned active matrix screens. In addition, they provide access to extremely low-cost integrated circuits, such as those required for transponders in RFID systems.
- An advantage of organic microelectronic devices is that they use organic materials that can be processed at relatively low temperatures, which are usually below 200 ° C. Therefore, it is possible to use cheap, flexible, transparent and unbreakable polymer films instead of rigid and fragile glass or quartz substrates.
- the organic materials also allow the practitioner ⁇ dung faster, easier and less expensive manufacturing techniques.
- cheap printing techniques can can be set to apply the polymers used for the various layers and / or low molecular weight organic materials to the flexible substrate and to structure.
- the gate potential for the control of transistors can be selected the smaller, the thinner the gate dielectric is produced.
- High-quality, extremely thin dielectric layers made of organic materials are therefore of great interest for a large number of applications, such as the realization of the above-mentioned low-cost, possibly battery-operated and optionally on large-area flexible substrates.
- the thickness of the gate dielectric is generally optimized by throwing or printing the solution of a polymer thinner and thinner (top-down). This method, however, reaches its limits when layer thicknesses below 50 nm are to be achieved.
- the generation of organic gate dielectrics with a thickness below 50 nm is made possible by the use of long-chain organic molecules, which consist of an anchor group, a ⁇ lectric unit and an optional head group. By correctly coordinating the chemical composition and structure of the anchor group on the chemical properties of the surface on which the organic dielectric is to be formed, a self - organization of the long ⁇ chain organic molecules on the surface, in which the molecules on their anchor group on the Surface anchored.
- the layers thus obtainable consist of monolayers of the long-chain organic compound and are accordingly designated as self-assembled monolayers (abbr .: SAM, of "self-assembled monolayer”).
- SAMs have excellent insulating properties and can be used as a gate dielectric in the transistor architecture sketched in FIG. They have a thickness of less than 5 nm on special preferably between 1.5 nm and 3 nm. This method can be referred to as a bottom-up approach.
- T-SAMs top-linked self-assembled monolayers
- Molecules for T-SAMs additionally have a head group in addition to the anchor group and the dielectric unit.
- the head groups of the ⁇ ser molecules provide for a particular stability of the SAMs to chemical and physical attacks by ver ⁇ various processes such as wet chemical etching or metal evaporation by the layer additionally by from ⁇ form a binding ⁇ - ⁇ -interaction stabilize ( top link).
- the top link has enabled the production of gate dielectrics of corresponding quality and thus the production of OFETs.
- the molecules with silane anchor group described in these two patent applications are particularly well suited for the formation of monolayers on silicon substrates with silicon dioxide natural layer.
- the compounds with silane anchor group described in DE 103 28 810 and DE 103 28 811 also form SAMs.
- the leakage currents of the gate dielectrics are too high for real applications obtained with these SAMs, for example by precipitation of 18-phenoxyoctadecyl-1-trichlorosilane on aluminum.
- organic molecules are described with phosphonic acid anchor group, which can serve to form SAMs in OFETs.
- Phosphonic acids with a long alkyl chain and terminal methyl group can be prepared by nucleophilic substitution (S H 2 mechanism) of a long-chain alkyl bromide with a trialkyl phosphite in the manner of a Michaelis-Arbuzow reaction.
- S H 2 mechanism nucleophilic substitution
- 1-octadecyl bromide with triethylphosphite the commercially available octadecylphosphonic acid is produced in good yield.
- SAMs self-assembled monolayer
- X is a radical which is selected from a) the alkyl chains having 2 to 20 carbon atoms, which may be straight-chain or branched and / or substituted and / or may contain one or more unsaturated bonds;
- Y is oxygen, sulfur, selenium or NH, when X is a partially or completely fluorinated alkyl chain and (CH 2 ) m O,
- Ar is an optionally substituted aromatic group, and - the radicals Ri to R 4 independently of one another hydrogen,
- Alkyl radicals having 1 to 20 carbon atoms which may be straight-chain or branched and / or substituted and / or contains unsaturated bond, a per-fluroalkyl radical;
- R 5 and R 6 are an alkyl radical having 1 to 20 carbon atoms, which may be straight-chain or branched and / or monosubstituted or polysubstituted and / or may contain one or more unsaturated bonds or a perfluoroalkyl radical.
- the radical X is an n-alkyl chain of the formula - (CHa) x -, in which x represents an integer in the range of 1 and 19.
- Ar represents the following radicals:
- the phenyl group is particularly preferred. It has been found, quite surprisingly, that the compound of the general formula I can be reacted virtually quantitatively with a thiocarboxylic acid of the general formula II without addition of a catalyst to obtain a thioester. The thioester can then be reduced with a reducing agent, especially with lithium aluminum hydride LiAlH 4 , to the corresponding thiol. The resulting thiol binds to metallic components and surfaces, in particular of noble metal, such as Au, Ag, Pt, Pd, Rh, Ru, etc. but also to some semiconductors such as GaAs or indium phosphide and forms a SAM, which is additionally stabilized by the head group ,
- thioester is not necessary in some cases.
- Many thioesters such as the thioacetic acid ester, add with elimination of the corresponding carboxylic acid, such as acetic acid to the surface of a noble metal r in particular of gold, and then form a self-assembled monolayer.
- AIBN azobisisobutyrodinitrile
- the synthetic routes described above for the preparation of thiols and phosphonic acids and their derivatives are very flexible and allow the preparation of a large class of compounds which have an anchor group (thiol radical or phosphonic acid radical) which can interact with the surface, and a omega-permanent group (the head group). These compounds form on their surface self-assembled monolayers via their anchor group, which are stabilized by the head groups.
- the compounds having a phosphonic acid residue prepared by the process according to the invention bind particularly well to layers of a material selected from aluminum, silicon and titanium. These materials are always coated with a thin layer of oxide because of their non-noble character in an oxygen-containing atmosphere.
- alloys containing the said metals are particularly preferred.
- the compounds prepared by the process according to the invention with a thiol radical bind particularly well to noble metal surfaces, for.
- electrodes consisting of silver, gold, platinum, rhodium, ruthenium, palladium or mercury or an alloy of one or more of these precious metals.
- alloys containing the said metals are also alloys containing the said metals to a proportion greater than 30%.
- Particularly preferred are surfaces which consist of gold or gold.
- Fig. 1 shows the basic structure of a polymer transistor with a bottom-gate bottom-contact structure
- FIG. 2 illustrates a bottom-gate top-contact structure that examines the suitability of the organic materials for microelectronics produced in the following embodiments, the gate electrode being made of aluminum or gold;
- FIG. 3 shows the characteristic curves of the test transistor whose gate dielectric consists of a self-organized layer of the organic compound according to Example 2;
- FIG. 4 contains a schematic representation of the five-stage ring oscillator from Example 9, a snapshot of the oscillation on the oscilloscope and the dependence of the step delay on the supply voltage.
- Example 2 The reaction is carried out as in Example 1 with the difference that diethyl phosphite is used instead of dimethyl phosphite. In this case, the corresponding diethyl ester is obtained. Subsequently, the diethyl ester is hydrolyzed to 18-phenoxyoctadecylphosphonic acid under the reaction conditions indicated in Example 2.
- Example 7 Production of an organic field effect transistor with a gate electrode made of aluminum
- Aluminum is vapor-deposited on a glass plate with a layer thickness of 100 nits in a vacuum.
- the self-assembled monolayer is deposited from the liquid phase or the gas phase or in the ⁇ -contact pressure as described in DE 10 2004 00 960.7.
- 30 nm of pentacene are vapor-deposited from the gas phase.
- the transistor test structure shown in Fig. 2 is completed by vapor deposition of gold electrodes through a shadow mask. The transistor characteristics obtained for this transistor are shown in FIG.
- Example 8 Production of a component for the food packaging industry
- Example 7 The manufacturing method shown in Example 7 is carried out with the difference that a polyester film, as used for example in the food packaging industry, is coated with aluminum instead of a glass plate.
- the finished component can be used in the food packaging industry for labeling foods.
- the glass plate from Example 7 is provided with a photoresist and exposed at a wavelength of 365 nm through a chromium-on-glass mask.
- the photoresist is developed with an aqueous KOH solution, which simultaneously etches the aluminum layer.
- a bottom Contact transistor structure of FIG. 2 completed.
- the individual masks were matched to each other or the transistors interconnected so that a ring oscillator according to FIG. 4 is formed.
- An oscilloscope recording of the ring oscillator and the dependence of the step delay of the supply voltage of the ring oscillator are also shown in Fig. 4.
- Example 11 Production of an organic field-effect transistor with a gate electrode made of platinum or palladium
- the OFETs are prepared as in Example 10 with the difference that in the first process step platinum or palladium is vapor-deposited on the glass plate to produce the gate electrode.
- platinum or palladium is vapor-deposited on the glass plate to produce the gate electrode.
- very stable Top-link SAMs are obtained when the organic compound obtained in Example 5 is used.
- Example 12 Production of a component for the food packaging industry The manufacturing process shown in Example 10 is carried out with the difference that a polyester film, as used for example in the food packaging industry, is vapor-deposited instead of a glass plate with a very thin layer of gold.
- the obtained substrate is suitable for the production of polymer electronic circuits, such as an organic field effect transistor for labeling foodstuffs in the food packaging industry.
- Example 13 Production of a ring oscillator
- the glass plate of Example 10 is provided with a photoresist and exposed at a wavelength of 365 nm through a chromium-on-glass mask.
- the photoresist is developed with an aqueous KOH solution.
- the etching of the gold layer takes place in highly diluted aqua regia (1:30).
- a bottom-contact transistor structure according to FIG. 2 is completed in the further structure analogously to Example 10.
- the individual masks have been matched to one another or the transistors are interconnected in such a way that a ring oscillator is produced which corresponds to the ring oscillator depicted in FIG. 4.
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Abstract
La présente invention concerne un procédé pour synthétiser des composés organiques qui peuvent former une couche monomoléculaire auto-organisée. Ces composés sont obtenus en mettant en réaction une oléfine avec un acide thiocarboxylique, puis en mettant en oeuvre une hydrogénation afin d'obtenir un thiol, ou avec un phosphite, puis en mettant en oeuvre une hydrolyse afin d'obtenir de l'acide phosphonique.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102004057760A DE102004057760A1 (de) | 2004-11-30 | 2004-11-30 | Methode zur Synthese von langkettigen Phosphonsäurederivaten und Thiolderivaten |
PCT/EP2005/056176 WO2006058858A2 (fr) | 2004-11-30 | 2005-11-23 | Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol |
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EP1817804A2 true EP1817804A2 (fr) | 2007-08-15 |
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EP05823798A Withdrawn EP1817804A2 (fr) | 2004-11-30 | 2005-11-23 | Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol |
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US (1) | US20080275273A1 (fr) |
EP (1) | EP1817804A2 (fr) |
DE (1) | DE102004057760A1 (fr) |
WO (1) | WO2006058858A2 (fr) |
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DE102006033713A1 (de) | 2006-05-30 | 2007-12-06 | Osram Opto Semiconductors Gmbh | Organisches lichtemittierendes Bauelement, Vorrichtung mit einem organischen lichtemittierenden Bauelement und Beleuchtungseinrichtung sowie Verfahren zur Herstellung eines organischen lichtemittierenden Bauelements |
WO2009000820A2 (fr) * | 2007-06-28 | 2008-12-31 | Siemens Aktiengesellschaft | Additif anticorrosion pour liquides |
DE102008006374B4 (de) * | 2007-09-27 | 2018-12-06 | Osram Oled Gmbh | Elektrisches organisches Bauelement und Verfahren zu seiner Herstellung |
US7657999B2 (en) * | 2007-10-08 | 2010-02-09 | Advantech Global, Ltd | Method of forming an electrical circuit with overlaying integration layer |
EP2304820A1 (fr) | 2008-07-18 | 2011-04-06 | Georgia Tech Research Corporation | Électrodes stable à travail d'extraction modifié et procédés pour dispositifs électroniques organiques |
KR101880838B1 (ko) * | 2008-08-04 | 2018-08-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 박막 트랜지스터용 하이브리드 유전 재료 |
JP5699127B2 (ja) * | 2009-04-06 | 2015-04-08 | ジョージア・テック・リサーチ・コーポレーション | 新規なホスホン酸表面改質剤を含む電子デバイス |
US8124485B1 (en) | 2011-02-23 | 2012-02-28 | International Business Machines Corporation | Molecular spacer layer for semiconductor oxide surface and high-K dielectric stack |
US9701698B2 (en) * | 2014-06-13 | 2017-07-11 | The Chinese University Of Hong Kong | Self-assembled monolayers of phosphonic acids as dielectric surfaces for high-performance organic thin film transistors |
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US4036984A (en) * | 1974-04-30 | 1977-07-19 | Nissan Chemical Industries, Ltd. | Soil fungi inhibiting agent |
DE3012000A1 (de) * | 1980-03-28 | 1981-10-15 | Troponwerke GmbH & Co KG, 5000 Köln | S-alkyl-3-alkylthiopropionthioate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
JPS59111636A (ja) * | 1982-12-17 | 1984-06-27 | Fuji Photo Film Co Ltd | 熱現像カラー感光材料およびそれを用いたカラー画像形成方法 |
DE19927787C2 (de) * | 1999-06-18 | 2003-12-11 | Clariant Gmbh | Verfahren zur Herstellung von Alkylphosphonsäuren |
DE10206420A1 (de) * | 2002-02-15 | 2003-08-28 | Infineon Technologies Ag | Bedruckter Probenträger, ein Verfahren zu dessen Herstellung sowie dessen Verwendung |
DE10328810B4 (de) * | 2003-06-20 | 2005-10-20 | Infineon Technologies Ag | Syntheseverfahren für eine Verbindung zur Bildung einer selbstorganisierenden Monolage, Verbindung zur Bildung einer selbstorganisierenden Monolage und eine Schichtstruktur für ein Halbleiterbauelement |
DE10328811B4 (de) * | 2003-06-20 | 2005-12-29 | Infineon Technologies Ag | Verbindung zur Bildung einer selbstorganisierenden Monolage, Schichtstruktur, Halbleiterbauelement mit einer Schichtstruktur und Verfahren zur Herstellung einer Schichtstruktur |
JP4200212B2 (ja) * | 2003-08-06 | 2008-12-24 | 独立行政法人産業技術総合研究所 | アゾアリールメルカプトアルキルポリエチレングリコール |
DE102004009600B4 (de) * | 2004-02-27 | 2008-04-03 | Qimonda Ag | Selbstorganisierende organische Dielektrikumsschichten auf der Basis von Phosphonsäure-Derivaten |
GB0404372D0 (en) * | 2004-02-27 | 2004-03-31 | Koninkl Philips Electronics Nv | Liquid crystal display |
-
2004
- 2004-11-30 DE DE102004057760A patent/DE102004057760A1/de not_active Withdrawn
-
2005
- 2005-11-23 US US11/720,453 patent/US20080275273A1/en not_active Abandoned
- 2005-11-23 EP EP05823798A patent/EP1817804A2/fr not_active Withdrawn
- 2005-11-23 WO PCT/EP2005/056176 patent/WO2006058858A2/fr active Application Filing
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DE102004057760A1 (de) | 2006-06-08 |
US20080275273A1 (en) | 2008-11-06 |
WO2006058858A2 (fr) | 2006-06-08 |
WO2006058858A3 (fr) | 2006-09-21 |
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