EP1743389A2 - Ultradünne dielektrika und deren anwendung in organischen feldeffekt-transistoren - Google Patents
Ultradünne dielektrika und deren anwendung in organischen feldeffekt-transistorenInfo
- Publication number
- EP1743389A2 EP1743389A2 EP05753846A EP05753846A EP1743389A2 EP 1743389 A2 EP1743389 A2 EP 1743389A2 EP 05753846 A EP05753846 A EP 05753846A EP 05753846 A EP05753846 A EP 05753846A EP 1743389 A2 EP1743389 A2 EP 1743389A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- effect transistor
- organic field
- organic
- field effect
- 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- Withdrawn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
- 230000005669 field effect Effects 0.000 title claims abstract description 57
- 239000010410 layer Substances 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 32
- 239000004065 semiconductor Substances 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 17
- 125000005647 linker group Chemical group 0.000 claims abstract description 15
- 239000002356 single layer Substances 0.000 claims abstract description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000010703 silicon Substances 0.000 claims description 16
- 239000013545 self-assembled monolayer Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000151 deposition Methods 0.000 claims description 10
- 239000010936 titanium Substances 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 claims description 8
- 230000003993 interaction Effects 0.000 claims description 8
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052721 tungsten Inorganic materials 0.000 claims description 8
- 239000010937 tungsten Substances 0.000 claims description 8
- 239000010931 gold Substances 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims description 6
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 6
- 239000002094 self assembled monolayer Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- WLPWBUSZWTZYTQ-UHFFFAOYSA-N amino(aminoazo)amine Chemical compound NNN=NN WLPWBUSZWTZYTQ-UHFFFAOYSA-N 0.000 claims description 4
- IVHJCRXBQPGLOV-UHFFFAOYSA-N azanylidynetungsten Chemical compound [W]#N IVHJCRXBQPGLOV-UHFFFAOYSA-N 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- -1 irridium oxide Chemical compound 0.000 claims description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003384 small molecules Chemical class 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 4
- XGZGDYQRJKMWNM-UHFFFAOYSA-N tantalum tungsten Chemical compound [Ta][W][Ta] XGZGDYQRJKMWNM-UHFFFAOYSA-N 0.000 claims description 4
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- JFWLFXVBLPDVDZ-UHFFFAOYSA-N [Ru]=O.[Sr] Chemical compound [Ru]=O.[Sr] JFWLFXVBLPDVDZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002390 heteroarenes Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 150000004655 tetrazenes Chemical class 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000005411 Van der Waals force Methods 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 229910004121 SrRuO Inorganic materials 0.000 claims 1
- QAKZFDCCFWBSGH-UHFFFAOYSA-N [Ru].[Sr] Chemical compound [Ru].[Sr] QAKZFDCCFWBSGH-UHFFFAOYSA-N 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- KUJYDIFFRDAYDH-UHFFFAOYSA-N 2-thiophen-2-yl-5-[5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC=CC=2)=C1 KUJYDIFFRDAYDH-UHFFFAOYSA-N 0.000 description 1
- 229910018516 Al—O Inorganic materials 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
-
- 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]
- H10K10/464—Lateral top-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]
- H10K10/466—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
- H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
-
- 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
- H10K10/474—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a multilayered structure
- H10K10/476—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a multilayered structure comprising at least one organic layer and at least one inorganic layer
Definitions
- Organic field effect transistors can be used in a variety of ways. For example, organic ones are suitable
- Field effect transistors as pixel controls in active matrix screens are usually manufactured using field-effect transistors based on amorphous or polycrystalline silicon layers.
- the temperatures of usually more than 250 ° C required for the production of high-quality transistors based on amorphous or polycrystalline silicon layers require the use of rigid and fragile glass or quartz substrates. Thanks to the relatively low temperatures at which transistors are made based on organic semiconductors, which are usually less than 200 ° C, organic transistors allow the production of active matrix screens using cheap, flexible, transparent, unbreakable polymer films with considerable advantages compared to glass or quartz substrates.
- FIG. 1 The structure of an organic field effect transistor according to the prior art is shown schematically in FIG. 1.
- the minimum gate-source voltage required for the transistor is linearly related to the thickness of the gate dielectric; the thicker the gate dielectric, the greater the required gate-source voltage. It is therefore necessary to develop gate dielectrics that are as thin as possible, which, in addition to adequate electrical insulation, also enable optimal molecular orientation of the organic semiconductor layer and thus high charge carrier mobility in the semiconductor. Molecules which form an electrically insulating molecular self-assembled monolayer (“self-assembled monolayer” SAM) on the gate electrode are outstandingly suitable for this purpose.
- T-SAMs Topic-Linked Soap Assembled Mono Layers
- insulator layer serves as an insulator layer and can be used, for example, for organic field-effect transistors.
- T-SAMs Topic-Linked Soap Assembled Mono Layers
- They are particularly suitable there described molecular structures for the formation of monolayers on silicon substrates with a natural silicon oxide layer.
- organic field effect transistors with the T-SAM tsolator layers described in the above-mentioned patent applications in connection with pentazene, tetrazene and oligothiophenes show poorer electrical properties than when using silicon as gate material
- DE 10 2004 009 600.7 also describes SAMs for use in field effect transistors.
- the object of the present invention is to provide new classes of compounds which can serve as a monomolecular dielectric for use in field-effect transistors based on organic semiconductors. Another object of the invention is to provide organic field effect transistors which have a dielectric layer with improved properties. Another object of the invention is to propose materials that can be used in the manufacture of field effect transistors.
- independent claim 1 ' is therefore a field effect transistor with a substrate, with a source, a drain and a gate electrode and with an organic semiconductor material, a dielectric layer (gate dielectric) on the gate electrode. is arranged, which is formed from a self-assembled monolayer of a compound which is an aliphatic orientation group, has a head group, a linker group and an anchor group, the aliphatic orientation group, the head group, the linker group and the anchor group being linked to one another in the order mentioned.
- the materials according to the invention solve the problem of poorer electrical properties of organic field-effect transistors with the structure metal gate / T-SAM / semiconductor / metal contacts or with the structure metal gate / T-SAM / metal contact / semiconductor by one in the
- T-SAM molecules e.g. 18-phenoxy-octadecyl
- trichlorosilane of the formula C6H5 ⁇ (CH 2 ) i8SiCl3)
- the essential structural element of the T-SAM layers according to the invention is the aliphatic orientation group which is linked to the head group.
- Particularly suitable aliphatic orientation groups are relatively short n-alkane chains of the general formula - (CH 2 ) n-, where n is an integer from 2 to 10. The chains are particularly suitable if n has an even number.
- the aliphatic orientation group can with divalent heteroatoms, such as. B. 0 or S may be substituted.
- the aliphatic orientation group is attached to the head group either directly or via a bridge atom.
- All groups can be used as head groups which are to be determined in the position on the one hand the orientation of the molecule and on the other hand to stabilize through interactions, such as e.g. B. dipole-dipole, CT interactions, ⁇ interactions or by the van der Waals forces to contribute to the stabilization of the self-organized layer.
- all aromatics or heteroaromatics come into consideration as head groups, which contribute to the stabilization of the layer through the formation of ⁇ j interactions with neighboring molecules of the self-organized monolayers.
- Particularly suitable head groups according to the invention are aromatics or heteroaromatics with one and two-ring systems, since their spatial expansion best fulfills the space requirement in a densely packed monolayer.
- the particularly suitable groups are e.g. As phenyl, thiophene, furan, pyrrole, oxazole, thiazole, imidazole and pyridine.
- oligomers of such molecular building blocks are also possible, provided that they are connected as linearly as possible to ensure a tight packing on the surface.
- the connection to the corresponding linker group can be via a bridge atom such. B. 0 or S or directly, the synthetic accessibility determines the preferred variant.
- the linker groups preferably consist of n-alkane chains of the general formula - (CH 2 ) m-, where m is preferably between 2 and 26. An even number for m is particularly preferred.
- the n-alkyl chain can also with divalent heteroatoms such as. B. 0 or S may be substituted.
- Linear chains of the general formula [(-CH 2 -CH 2 -X) z], where X is 0 or S and z is a number between 2 and 10, are therefore also possible.
- the alkane or poly (thio) ether chain can also contain unsaturated bonds or have substituents.
- the anchor group can be varied depending on the electrode materials and should be chosen so that there is an interaction between the anchor group and the surface of the gate electrode.
- the anchor group can have a radical which consists of the group consisting of R-SiCl 3 , R-SiCl 2 alkyl, R-SiCl (alkyl) 2 , R-S OR 1 ⁇ , R-Si (OR 1 ) 2 alkyl , or R-SiOR 1 (alkyl) 2 if the Electrode consists of Si, Al, Ti, TaN, TiN or WN, or has a layer of the above-mentioned metals or alloys of these metals with a native or specifically produced oxide layer which is in contact with the anchor group.
- the anchor group can also have radicals consisting of the group consisting of R-SiCl 3 , R-SiCl 2 -alkyl, R-SiCl (Alkyl) 2 , R-Si (OR 1 ) 3 , R-Si (OR 1 ) 2 alkyl or R-SiOR 1 (alkyl) 2 are selected.
- the anchor group can be selected from the group consisting of e.g. B.
- the anchor group can be R-SH, R-SAc, RSS-Rl or R-S0 2 H.
- R denotes a linker group described above and Rl denotes an alkyl group which can also be substituted with, for example, heteroatoms.
- the thickness of the dielectric layer corresponds approximately to the length of the molecules according to the invention, which form the self-organized monolayer.
- the dielectric layer has a thickness of approximately 1 to approximately 10 nm, preferably approximately 2 to approximately 5 nm
- all materials that are one of the self-organized monolayer are suitable as materials for the gate electrode contain facing layer and interact with the anchor groups of the compounds of the invention.
- the preferred materials for the gate electrode are aluminum (Al), titanium (Ti), titanium nitride (TiN), tantalum (Ta), tantalum nitride (TaN), tungsten (W), titanium tungsten (TiW), tantalum tungsten (TaW), tungsten nitride (WN), tungsten carbonitride (WCN), irridium oxide (IrO), ruthenium oxide (RuO), strontium ruthenium oxide (SrRuO) or a combination of these layers and / or materials.
- the gate electrode optionally also has a layer of silicon (Si), titanium nitride silicon (TiNSi), silicon oxynitride (SiON), silicon oxide (SiO), silicon carbide (SiC) or silicon carbonitride (SiCN).
- Si silicon
- TiNSi titanium nitride silicon
- SiON silicon oxynitride
- SiO silicon oxide
- SiC silicon carbide
- SiCN silicon carbonitride
- the materials for the source and drain electrodes are not decisive for the function of the component.
- all conductive metals, formulations of these or polymers are suitable.
- the source or drain electrode can also have a layer of Si, TiNSi, SiON, SiO, SiC or SiCN.
- PEDOT.PSS (Baytron ® ) or polyaniline, for example, are suitable as polymeric contact materials.
- the semiconductor material based on an organic compound based on an organic compound
- semiconductor is selected from the group of “small molecules”.
- small molecules is understood to mean all organic semiconductor materials that are not polymers.
- the organic semiconductor is selected from the "small molecules” group consisting of pentazene, tetrazene, oligothiophene, phthalocyanines and merocyanines.
- the supply voltage of a field effect transistor depends in particular on the thickness of the dielectric layer (the gate dielectric) arranged on the gate electrode. Therefore, the field effect transistor according to the invention can be operated with a supply voltage of less than 5 volts and in particular less than 3 volts, namely in the range from 1 to 3 volts.
- the field effect transistors according to the invention are particularly suitable for use in the so-called "low cost” area of electronics and especially for organic field effect transistors with low supply voltages.
- a manufacturing method for manufacturing field effect transistors is provided.
- a substrate based on inorganic or organic materials is provided, on which a gate electrode is deposited.
- the gate electrode can then with the invention
- connection are brought into contact in order to obtain a self-organized monolayer of the connection according to the invention arranged on the gate electrode.
- the surface of the gate electrode has such properties that the anchor groups of the compounds according to the invention interact with the surface of the gate electrode.
- One so preserved Self-organized monolayer of the compound according to the invention can then be subjected to further production steps.
- the deposition and structuring of a source and a drain electrode with the subsequent deposition of a semiconductor material is therefore provided as the next step.
- the organic compound can be brought into contact with the material of the gate electrode by immersing a substrate with the gate electrode arranged thereon in a solution which has the organic compound according to the invention.
- Particularly suitable solvents are polar, aprotic solvents, such as toluene, tetrahydrofuran or cyclohexane.
- the density of the self-assembled monolayer of the organic compound and the duration of the deposition can be influenced by the concentration of the solution of the organic compound in which the substrate is immersed.
- concentration of the solution in the range of about 10 ⁇ 4 to 0.1 mol% of the organic compound is particularly suitable for the production of dense layers.
- the SAMs are deposited by immersing the substrate (with a defined first electrode) in the prepared solution. After the substrate has been immersed in the solution of the organic compound, a rinsing step with pure process solvent can then take place.
- the substrate can then optionally be rinsed with a volatile solvent such as acetone or dichloromethane and then dried. Drying can take place, for example, in the oven or on a hot plate under protective gas.
- the organic compound can also be brought into contact with the gate electrode by vapor deposition of the organic compound onto the gate electrode.
- the organic compound can then be separated in a closed reactor with heating.
- the reactor interior is evacuated after loading with the substrate with a defined gate electrode and aerated with inert gas such as argon or nitrogen in order to remove residual oxygen.
- the working pressure and working temperature are set, which essentially depend on the organic rest.
- a pressure of about 10 ⁇ 6 to 400 mbar and a temperature of about 80 to 200 ° C are particularly preferred.
- the ideal process conditions depend on the volatility of the organic compound. Depending on the process conditions, the coating times are usually between 3 min and 24 h.
- Fig. 1 The structure of a field effect transistor according to the prior art
- 2b shows a schematic representation of the compounds according to the invention, which can be used to form self-organized monolayers in field-effect transistors;
- Fig. 3 voltage characteristics of the field effect transistor according to the invention.
- FIG. 4 continuity characteristics of the field effect transistor according to the invention.
- the structure of a field effect transistor shown in FIG. 1 has already been described in the introductory part.
- This aliphatic orientation group for improving the electrical properties of organic field-effect transistors can be described in analogy to the mode of action of octadecyltrichlorosilane (OTS) on Si0 2 surfaces.
- OTS octadecyltrichlorosilane
- the mode of action is e.g. B. in DJ Gundlach et al. , Organic Field Effect Transistors - Proceedings of SPIE, vol. 4466 (2001) 5464 and K. Klauk et al., J. Appl. Phys. 92 (2002) 5259 to 5263.
- the aliphatic orientation group takes over the function of OTS on Si0 2 , the insulation properties being largely determined by the rest of the molecule, namely by the anchor groups, linker groups and head groups. It is advantageous with these materials that only one molecule has to be deposited in order to set all of these desired properties.
- the general The structure of the materials according to the invention allows great flexibility in the choice of the individual components for their synthesis. As a result, the number of materials according to the invention is significantly expanded compared to the compounds described in patent applications DE 103 28 810 and DE 103 28 811 with improved function.
- the materials according to the invention are particularly suitable for the production of organic field-effect transistors and integrated circuits based thereon with metallic gate electrodes.
- the electronic properties of the field effect transistor according to the invention are shown in FIGS. 3 and 4.
- the organic field effect transistor was obtained by depositing 18- (4-hexyl-phenoxy-octadecyl) trichlorosilane on a silicon gate electrode.
- the self-organized monolayer of 18- (4-hexyl-phenoxy-octadecyl) trichlorosilane is approx. 2.8 n thick.
- the source and drain contacts are made of gold and the semiconductor material was pentacene.
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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Formation Of Insulating Films (AREA)
- Electrodes Of Semiconductors (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004022603A DE102004022603A1 (de) | 2004-05-07 | 2004-05-07 | Ultradünne Dielektrika und deren Anwendung in organischen Feldeffekt-Transistoren |
| PCT/DE2005/000847 WO2005109538A2 (de) | 2004-05-07 | 2005-05-04 | Ultradünne dielektrika und deren anwendung in organischen feldeffekt-transistoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1743389A2 true EP1743389A2 (de) | 2007-01-17 |
Family
ID=35320915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05753846A Withdrawn EP1743389A2 (de) | 2004-05-07 | 2005-05-04 | Ultradünne dielektrika und deren anwendung in organischen feldeffekt-transistoren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20080290337A1 (de) |
| EP (1) | EP1743389A2 (de) |
| JP (1) | JP2007536748A (de) |
| KR (1) | KR100836981B1 (de) |
| CN (1) | CN1998096A (de) |
| DE (1) | DE102004022603A1 (de) |
| WO (1) | WO2005109538A2 (de) |
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| JP5036256B2 (ja) * | 2006-09-12 | 2012-09-26 | 株式会社リコー | 有機無機複合材料 |
| DE102007027473A1 (de) | 2007-06-14 | 2008-12-18 | Manroland Ag | Drucktechnisch hergestellte funktionale Komponenten |
| DE102007029836A1 (de) | 2007-06-28 | 2009-01-02 | Siemens Ag | Zusatz für Kühlwasserkreisläufe in Kraftwerken sowie Verfahren zum Korrisionsschutz in Kühlwasserkreisläufen von Kraftwerken |
| DE102007029837A1 (de) | 2007-06-28 | 2009-01-02 | Siemens Ag | Zusatz für ein Reinigungs- und/oder Pflegemittel zur Verwendung in Haushaltsgeräten sowie derartiges Reinigungs- und/oder Pflegemittel |
| KR100878449B1 (ko) * | 2007-08-08 | 2009-01-19 | 한국화학연구원 | 유기절연체의 신규 표면 처리 방법 및 이를 적용한유기박막트랜지스터 |
| DE102008006374B4 (de) * | 2007-09-27 | 2018-12-06 | Osram Oled Gmbh | Elektrisches organisches Bauelement und Verfahren zu seiner Herstellung |
| DE102007046444A1 (de) * | 2007-09-28 | 2009-04-02 | Siemens Ag | Organischer Photodetektor mit reduziertem Dunkelstrom |
| US8899470B2 (en) * | 2007-11-29 | 2014-12-02 | Corning Incorporated | Method for bonding refractory ceramic and metal |
| JP5022950B2 (ja) * | 2008-03-07 | 2012-09-12 | 株式会社日立製作所 | 有機薄膜トランジスタおよびその製造方法 |
| KR20100091663A (ko) * | 2009-02-11 | 2010-08-19 | 삼성전자주식회사 | 표면개질제, 이를 사용하여 제조된 적층 구조, 그 구조의 제조방법 및 이를 포함하는 트랜지스터 |
| US8114787B2 (en) | 2009-02-19 | 2012-02-14 | Empire Technology Development Llc | Integrated circuit nanowires |
| JP4923120B2 (ja) * | 2009-03-17 | 2012-04-25 | 株式会社東芝 | 粒子および近接場光導波路 |
| DE102009023350A1 (de) | 2009-05-29 | 2010-12-02 | Osram Opto Semiconductors Gmbh | Elektronisches Bauelement und Verfahren zur Herstellung eines elektronischen Bauelements |
| JP5717490B2 (ja) | 2011-03-24 | 2015-05-13 | 株式会社東芝 | 有機分子メモリ |
| FR2978292B1 (fr) * | 2011-07-22 | 2013-08-23 | Commissariat Energie Atomique | Utilisation de couches auto-assemblees pour le controle de la tension de seuil de transistors organiques |
| US9899317B1 (en) | 2016-09-29 | 2018-02-20 | International Business Machines Corporation | Nitridization for semiconductor structures |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0766990B2 (ja) * | 1988-07-15 | 1995-07-19 | 松下電器産業株式会社 | 有機デバイスおよびその製造方法 |
| US5349089A (en) * | 1989-07-07 | 1994-09-20 | National Starch And Chemical Investment Holding Corporation | Reagent for preparing polycationic polysaccharides |
| US5981970A (en) * | 1997-03-25 | 1999-11-09 | International Business Machines Corporation | Thin-film field-effect transistor with organic semiconductor requiring low operating voltages |
| NO312867B1 (no) * | 1999-06-30 | 2002-07-08 | Penn State Res Found | Anordning til elektrisk kontaktering eller isolering av organiske eller uorganiske halvledere, samt fremgangsmåte til densfremstilling |
| JP2001244467A (ja) * | 2000-02-28 | 2001-09-07 | Hitachi Ltd | コプラナー型半導体装置とそれを用いた表示装置および製法 |
| US6433359B1 (en) * | 2001-09-06 | 2002-08-13 | 3M Innovative Properties Company | Surface modifying layers for organic thin film transistors |
| US6870181B2 (en) * | 2002-07-02 | 2005-03-22 | Motorola, Inc. | Organic contact-enhancing layer for organic field effect transistors |
| US7285440B2 (en) * | 2002-11-25 | 2007-10-23 | International Business Machines Corporation | Organic underlayers that improve the performance of organic semiconductors |
| US7132678B2 (en) * | 2003-03-21 | 2006-11-07 | International Business Machines Corporation | Electronic device including a self-assembled monolayer, and a method of fabricating the same |
| JP2005079560A (ja) * | 2003-09-04 | 2005-03-24 | Hitachi Ltd | 薄膜トランジスタ,表示装置、およびその製造方法 |
| JP2005158765A (ja) * | 2003-11-20 | 2005-06-16 | Canon Inc | 電界効果型有機トランジスタおよびその製造方法 |
| DE102004009600B4 (de) * | 2004-02-27 | 2008-04-03 | Qimonda Ag | Selbstorganisierende organische Dielektrikumsschichten auf der Basis von Phosphonsäure-Derivaten |
-
2004
- 2004-05-07 DE DE102004022603A patent/DE102004022603A1/de not_active Ceased
-
2005
- 2005-05-04 CN CNA2005800227476A patent/CN1998096A/zh active Pending
- 2005-05-04 EP EP05753846A patent/EP1743389A2/de not_active Withdrawn
- 2005-05-04 WO PCT/DE2005/000847 patent/WO2005109538A2/de not_active Ceased
- 2005-05-04 JP JP2007511852A patent/JP2007536748A/ja active Pending
- 2005-05-04 KR KR1020067023280A patent/KR100836981B1/ko not_active Expired - Fee Related
- 2005-11-17 US US11/568,791 patent/US20080290337A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005109538A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004022603A9 (de) | 2007-03-08 |
| KR100836981B1 (ko) | 2008-06-10 |
| US20080290337A1 (en) | 2008-11-27 |
| JP2007536748A (ja) | 2007-12-13 |
| WO2005109538A3 (de) | 2006-09-08 |
| KR20070015565A (ko) | 2007-02-05 |
| WO2005109538A2 (de) | 2005-11-17 |
| CN1998096A (zh) | 2007-07-11 |
| DE102004022603A1 (de) | 2005-12-15 |
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