EP2066722A2 - Oligomeric compounds which form a semiconductor layer - Google Patents
Oligomeric compounds which form a semiconductor layerInfo
- Publication number
- EP2066722A2 EP2066722A2 EP07820116A EP07820116A EP2066722A2 EP 2066722 A2 EP2066722 A2 EP 2066722A2 EP 07820116 A EP07820116 A EP 07820116A EP 07820116 A EP07820116 A EP 07820116A EP 2066722 A2 EP2066722 A2 EP 2066722A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oligomeric
- linear
- compounds
- general formula
- compound
- 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- Withdrawn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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 178
- 239000004065 semiconductor Substances 0.000 title claims description 39
- 239000000203 mixture Substances 0.000 claims abstract description 93
- 239000011258 core-shell material Substances 0.000 claims abstract description 32
- 229920002521 macromolecule Polymers 0.000 claims abstract description 28
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 53
- -1 chlorosilyl Chemical group 0.000 claims description 42
- 229930192474 thiophene Natural products 0.000 claims description 31
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical group O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 239000010703 silicon Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000003577 thiophenes Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000005669 field effect Effects 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 46
- 239000010410 layer Substances 0.000 description 29
- 239000010408 film Substances 0.000 description 26
- 239000000758 substrate Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 230000037230 mobility Effects 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 238000012512 characterization method Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- IDCLTMRSSAXUNY-UHFFFAOYSA-N 5-hydroxylansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC(O)=CC=C2N1 IDCLTMRSSAXUNY-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229920000587 hyperbranched polymer Polymers 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005442 molecular electronic Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000412 polyarylene Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 210000001520 comb Anatomy 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000006104 solid solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 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
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 125000002378 chlorosyl group Chemical group O=Cl[*] 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical group BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- NVYQDQZEMGUESH-UHFFFAOYSA-N dimethylsilyloxy(dimethyl)silane Chemical compound C[SiH](C)O[SiH](C)C NVYQDQZEMGUESH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NAHBVNMACPIHAH-HLICZWCASA-N p-ii Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920003257 polycarbosilane Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000007704 wet chemistry method Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
-
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- 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
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Definitions
- the invention relates to oligomeric organic compounds and their mixtures with macromolecular compounds having a core-shell structure and / or monomeric linear compounds, with improved semiconducting properties, as well as their use in electronic components.
- OFETs Simple structuring and integration of OFETs into integrated organic semiconductor circuits makes possible low-cost solutions for smart cards or price tags, which hitherto can not be realized with the aid of silicon technology due to the price and lack of flexibility of the silicon components. Also, OFETs could be used as switching elements in large area flexible matrix displays.
- An overview of organic semiconductors, semiconductor integrated circuits and their applications is given, for example, in Electronics 2002, Vol. 15, p. 38 or H. Klauk (publisher), Organic Electronics, Materials, Manufacturing and Applications, Wiley-VCH 2006.
- a field effect transistor is a three-electrode element in which the conductivity of a thin conduction channel between two electrodes (called “source” and “drain”) is determined by means of an electrode (called “gate”) separated from the conduction channel by the third insulator layer.
- the most important characteristic features of a field-effect transistor are the mobility of the charge carriers, which decisively determine the switching speed of the transistor and the ratio between the currents in the switched and unswitched state, the so-called "on / off ratio”.
- Organic field-effect transistors have hitherto used two large classes of interconnects. Compounds of both classes have continuous conjugated units and are subdivided into conjugated polymers and conjugated oligomers depending on molecular weight and structure. Oligomers usually have a uniform molecular structure and a molecular weight below 10,000 daltons. Polymers usually consist of chains of uniform repeating units with a molecular weight distribution. However, there is a smooth transition between oligomers and polymers.
- oligomers are often vaporizable and are applied to substrates by vapor deposition.
- polymers are often referred to independent of their molecular structure compounds that are no longer volatile and therefore applied by other methods.
- polymers as a rule compounds are sought which are soluble in a liquid medium, for example organic solvents, and which can then be applied by means of corresponding application methods.
- a very common application method is e.g.
- the wet-chemical process has a greater potential for easily obtaining inexpensive organic integrated semiconductor circuits.
- oligomers as molecularly uniform and often volatile compounds, can be purified relatively simply by sublimation or chromatography.
- mobilities hereafter referred to as mobilities, have reached 0.02 cmVVs (Science, 2000, vol. 290, p. 2123), with regioregular poly (3-hexylthiophene-2,5-diyl) (U).
- oligomeric semiconducting compounds are, for example, oligothiophenes, especially those having terminal alkyl substituents according to formula (IU)
- Oligothiophene are usually hole semiconductors, ie only positive charge carriers are transported.
- the laid-open specification WO 02/26859 A1 describes polymers of a conjugated back wheel to which aromatic conjugated chains are attached.
- the polymers carry darylamine side groups that allow electron conduction.
- these compounds are unsuitable as semiconductors due to the diarylamine side groups.
- EP-A 1 398 341 and EP-A 1 580 217 describe semiconducting.
- Compounds with a core-shell structure used as semiconductors in electronic devices can be used and processed from solution.
- these compounds tend to give poorly crystallizing films during processing, which, as crystallized films are a prerequisite for high charge carrier mobility, may be a hindrance to some applications.
- films of organic semiconductors can be subordinated by temperature treatment (deLeeuw et al., WO 2005104265), the macromolecular nature of the compound can also hinder a complete subsequent order by means of temperature treatment.
- the object of the invention was to provide organic compounds which can be processed from common solvents which give semiconducting films with good properties and which remain sufficiently stable when stored in air. Such compounds would be ideal for the large-scale application of organic semiconducting layers.
- the compounds form high quality layers of uniform thickness and morphology and are suitable for electronic applications.
- oligomeric organic compounds and their mixtures with macromolecular compounds having a core-shell structure and / or compounds with monomeric linear compounds give particularly suitable films having particular properties.
- the oligomeric compounds consist of compounds with a linear structure, which are connected to one another via flexible bridges. This is surprising and extremely unexpected, since as far as possible compounds with high purity and uniformity have been sought in order to positively influence the crystallization behavior.
- the invention relates to oligomeric compounds of the general formula (M),
- L is a linear conjugated oligomeric chain, preferably one containing optionally substituted thiophene, phenylene or fluorenyl units,
- R A , R B independently of one another are the same or different, linear or branched C 2 -
- Oligo- or C 2 -C 20 -polyether radicals preferably for linear or branched C 2 -C 2 O alkylene radicals, X A , X B independently of one another for an identical or different group (s) selected from an optionally substituted vinyl group, a chlorine, iodine, hydroxyl, alkoxy group having 1 to 3 carbon atoms, alkoxysilyl, SiIyI, chlorosilyl, Siloxane, hydroxy, carboxy, methyl or ethyl carbonate, aldehyde, methyl carbonyl, amino amido, sulfone, sulfonic acid, halosulfonyl, sulfonate
- group (s) selected from an optionally substituted vinyl group, a chlorine, iodine, hydroxyl, alkoxy group having 1 to 3 carbon atoms, alkoxysilyl, SiIyI, chlorosilyl, Siloxane, hydroxy, carboxy, methyl or
- Phosphoric acid, phosphonate, trichloromethyl, tribromomethyl, cyanate, isocyanate, thiocyanate, isothiothiocyanate, cyano, nitro group or H preferably represents disuloxane or H,
- Y independently represent an identical or different group (s), but preferably for an identical group selected from an optionally substituted
- n is an integer from 1 to 10, preferably an integer from 1 to 3.
- Another object of the invention are mixtures containing at least one compound of general formula (M) and at least one macromolecular compound having a core-shell structure, wherein the core (K) has a macromolecular basic structure based on silicon and / or carbon and having at least 3 is connected via a carbon-based linking chain with carbon-based linear oligomeric chains having continuously conjugated double bonds, and wherein the linear conjugated chains are each saturated with at least one other, in particular aliphatic, araliphatic or oxyaliphatic chain having no conjugated double bonds.
- the embodiment according to the invention are mixtures comprising the oligomeric compound (s) of the general formula (M) and the macromolecular compound (s) having a core-shell structure in a weight ratio of 99: 1 to 1:99, preferably 10:90 to 90:10.
- Such mixtures may be either solid mixtures or solutions containing the two aforementioned components.
- Yet another object of the invention are mixtures comprising at least one oligomeric compound of the general formula (M) and at least one compound of the general formula (P) - o -
- L is a linear conjugated oligomeric chain, preferably one containing optionally substituted thiophene, phenylene or fluorenyl units,
- R c , R D independently of one another are the same or different, linear or branched C 2 -
- C 2 crAlkylenreste C 3 -C 8 cycloalkylene, mono- or polyunsaturated C 2 - C 20 -Alkeny ⁇ enreste, C 2 -C 20 -Oxyalkylenreste, C 2 -C 2 ( ⁇ -Aralkylenreste or C 2 -C 20 - oligo- or C 2 -C 2 crPolyetherreste, preferably for linear or branched C 2 -C 20 alkylene radicals,
- X c , X D independently of one another represent an identical or different group (s) selected from an optionally substituted vinyl group, a chlorine, iodine, hydroxyl, alkoxy group having 1 to 3 carbon atoms, alkoxysilyl, silyl, chlorosyl, Siloxane, hydroxy, carboxy, methyl or ethyl carbonate, aldehyde, methylcarbonyl, amino-amido, sulfonic, sulfonic, halosulfonyl, sulfonate, phosphonic acid, phosphonate, trichloromethyl, tribromomethyl, , Cyanate,
- the embodiment of the invention are mixtures containing the oHgomere (n) compounds) of the general formula (M) and the compounds) of the general formula (P) in a weight ratio of 99: 1 to 1:99, preferably 20:80 to 80:20.
- Such mixtures may be either solid mixtures or solutions containing the two aforementioned components.
- suitable solvents are aromatics, ethers or halogenated aliphatic hydrocarbons, such as for example Chlorofo ⁇ n, toluene, xylenes, benzene, diethyl ether, dichloromethane, chlorobenzene, dichlorobenzene or tetrahydrofuran, or mixtures of these.
- the organic macromolecular compounds having a core-shell structure may, in a preferred embodiment, be oligomers or polymers.
- oligomers are to be understood as meaning compounds having a molecular weight of less than 1000 daltons and among polymers, compounds having an average molecular weight of 1000 daltons and greater.
- the average molecular weight may be the number average (M n ) or weight average (M w ).
- M n number average
- M n weight average
- the core-shell structure is a structure at the molecular level, i. it refers to the construction of a molecule as such.
- the terminal point of attachment of the linear conjugated oligomeric chain is to be understood as meaning the point in the terminal unit of the linear oligomeric chain having conjugated double bonds via which no further linking of a further one occurs. Terminal is to be understood as furthest from the core.
- the linear oligomeric chain with continuously conjugated double bonds is also referred to below as shortened linear conjugated oligomeric chain.
- the macromolecular compounds having a core-shell structure preferably have a core-shell structure of the general formula (Z) 5
- K is an n-functional core
- L is a linear conjugated oligomeric chain
- R for linear or branched C 2 -C 2 ⁇ ralkyl radicals, C 3 -Cs cycloalkylene radicals, mono- or polyunsaturated C 2 -C 2 o-alkenyl radicals, C 2 -C 20 -alkoxy radicals, C 2 "C 3 ⁇ rAralkylreste or
- q is an integer greater than or equal to 3, preferably equal to 4
- the shell of the preferred compounds is formed from the q -V-L-R building blocks, which are each attached to the core.
- Such compounds are designed to produce a multifunctional entity, i. branched core, linking chains, linear conjugated oligomeric chains and non-conjugated chains are linked together.
- the core composed of multifunctional units preferably has dendritic or hyperbranched structures.
- Hyperbranched structures and their preparation are known per se to those skilled in the art.
- Hyperbranched polymers or oligomers have a special structure, which is predetermined by the structure of the monomers used. As monomers so-called. ABn monomers are used, i. Monomers carrying two different functionalities A and B. Of these, one functionality (A) is present only once per molecule and the other functionality (B) several times (n times). The two functionalities A and B can be reacted with each other to form a chemical bond, e.g. be polymerized. Due to the monomer structure, branched polymers with a tree-like structure, so-called hyperbranched polymers, are formed during the polymerization.
- Hyperbranched polymers have no regular branching sites, no rings, and almost exclusively B functionalities at the chain ends. Hyperbranched polymers, their structure, the question of branching and their nomenclature are for the example of hyperbranched polymers based on silicones in LJ. Mathias, T.W. Carothers, Adv. Dendritic Macromol. (1995), 2, 101-121 and the work cited therein.
- the hyperbranched structures are preferably dendritic polymers.
- dendritic structures are synthetic macromolecular structures which are obtained stepwise by linking in each case 2 or more monomers to each builds up bound monomers, so that with each step, the number of monomer end groups grows exponentially and at the end of a spherical tree structure is formed.
- three-dimensional, macromolecular structures are formed with groups that have branch points and continue from one center to the periphery in a regular fashion.
- Such structures are usually built up layer by layer by methods known to those skilled in the art. The number of layers is usually called generation. The number of branches in each layer as well as the number of terminal groups increase with increasing generation. Due to their regular structure, dendritic structures can offer special advantages. Dendritic structures, preparation methods and nomenclature are known to those skilled in the art and described, for example, in GRNewkome et al., Dendrimers and Dendrons, Wiley-VCH, Weinheim, 2001.
- dendritic or hyperbranched core are, for example, those described in US Pat. No. 6,025,462.
- hyperbranched structures such as polyphenylenes, polyether ketones, polyesters, such as e.g. in US-A 5,183,862, US-A 5,225,522 and US-A 5,270,402, aramids as e.g. in US-A 5,264,543, polyamides, e.g. in US-A 5,346,984, polycarbosilanes or polycarbosiloxanes, e.g.
- dendritic or hyperbranched core other structural units can be used to construct the dendritic or hyperbranched core.
- the role of the dendritic or hyperbranched core is primarily to provide a range of functionalities and thus to form a matrix to which the linker chains with the linear conjugated oligomeric chains are attached and thus arranged in a core-shell structure can.
- the linear conjugated oligomeric chains are pre-ordered by attachment to the matrix, thus increasing their effectiveness.
- the dendritic or hyperbranched core has a number of functionalities - in the sense of linking sites - which are suitable for attaching the linking chains with the linear conjugated oligomeric chains.
- the dendritic core like the core composed of hyperbranched structures, has at least 3, but preferably at least 4, functionalities.
- Preferred structures in the dendritic or hyperbranched core are 1,3,5-phenylene units (formula Va) and units of the formulas (Vb) to (Ve), where a plurality of identical or different units of the formulas (Va) to (Ve) linked together,
- dendritic cores (K) composed of units of formula (V-a) are as follows:
- the link is made via the connecting chains (V) with the linear conjugated oHgomeren chains (L).
- the shell of the macromolecular compounds with core-shell structure is formed by connecting chains (V), linear conjugated oligomeric chains (L) and the nonconjugated chains (R).
- the oligomeric compounds of the general formula (M) are formed from the linear conjugated oligomeric chains (L) and the nonconjugated chains (R) having a terminal functionality (X) and a bridging unit (Y).
- the compounds of the general formula (P) are formed from the linear conjugated chains (L) and the non-conjugated chains (R) having a terminal functionality (X).
- Linking chains (V) are preferably those which provide high flexibility, i. have a high (intra) - raolekulare mobility and thereby cause a geometric arrangement of the segments -L- R to the core K. Flexible in the context of the invention in the sense of (intra) molecularly mobile to understand.
- connecting chains are basically linear or branched chains suitable, which have the following structural features:
- Suitable connecting chains are particularly preferably linear or branched C 2 -C 20 -alkylene chains, such as, for example, ethylene, n-butylene, n-hexylene, n-octylene and n-dodecylene chains, linear or branched polyoxyalkylene chains, for example -OCHr 5 Oligoether chains containing -OCH (CH 3 ) - or -O- (CH 2 ) 4 - segments, linear or branched siloxane chains, for example those with dimethylsiloxane structural units and / or straight-chain or branched carbo-silane chains, ie chains containing silicon-carbon Single bonds, wherein the silicon and the carbon atoms in the chains can be arranged in an alternating, random or block-like manner, such as those with -SiR 2 -CH 2 -CH 2 -CH 2 -SiR 2 -Strukturmaschineen. - -
- Suitable linear conjugated oligomeric chains (L) of the general formulas (M), (P) and (Z) are in principle all chains which have structures which as such form electrically conductive or semiconductive oligomers or polymers. These are, for example, optionally substituted polyanilines, polythiophenes, polyethylenedioxythiophenes, polyphenylenes, polypyrroles, polyacetylenes, polyisonaphthenes, polyphenylenevinylenes, polyfluorenes, which can be used as horaopolymers or oligomers or as copolymers or oligomers. Examples of such structures which can preferably be used as linear conjugated oligomeric chains are chains of 2 to 10, more preferably 2 to 8 units of the general formulas (VI-a) to (VI-f),
- R 1, R 2 and R 3 may be the same or different and represent hydrogen, straight-chain or branched CrC stand 2 o alkyl or CrQo alkoxy groups, preferred are the same and stand for hydrogen,
- R 4 may be the same or different and represent hydrogen, straight or branched Ci-C 2 o-Alky ⁇ phenomenon or C
- the positions of the formulas (Va) to (Vf) marked with * denote the linking sites via which the units (Va) to (VO are linked to one another to the linear conjugated oligomeric chain or to the non-conjugated chains (R) at the respective chain ends. wear.
- the prefixed numbers 2,5- resp. 1,4- specify the positions in the units that are linked.
- the linear conjugated oligomeric chains are each saturated at the terminal attachment sites with a nonconjugated chain (R).
- Non-conjugated chains are preferably those which have high flexibility, ie high (intra) molecular mobility, thereby interact well with solvent molecules and thus produce improved solubility. Flexible in the context of the invention in the sense of (intra) molecularly mobile to understand.
- the non-conjugated chains (R) are optionally oxygen-interrupted straight-chain or branched aliphatic, unsaturated or araliphatic chains having 2 to 20 carbon atoms, preferably having 6 to 20 carbon atoms, or C 3 -C 8 cycloalkylenes.
- Particularly preferred are unbranched C 2 -C 2 o-alkyl or C 2 -C 2 O-alkoxy groups or C 3 -C 8 cycloalkylenes.
- Suitable chains are alkyl groups such as n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl and n-dodecyl groups and also alkoxy groups such as n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy , n-decyloxy and n-dodecyloxy groups or C3-C8 cycloalkylenes such as cyclopentyl, cyclohexyl or cycloheptyl.
- Structural elements of the general formulas (V ⁇ -aR) and (VI-bR) may be mentioned as examples of structural elements LR of the general formula (Z) consisting of linear conjugated oligomeric chains, which are each saturated at the terminal point of attachment by a nonconjugated chain:
- p is an integer from 2 to 10, preferably from 2 to 8, more preferably 2 to 7.
- Structural elements of the general formulas (VI-aR A / B ) and (VI-bR ⁇ 6 ) may be mentioned as examples of structural elements ⁇ R A -LR B - of the general formula (M):
- p is an integer from 2 to 10, preferably from 2 to 8, more preferably 4 to 6.
- Preferred embodiments of the macromolecular compounds having a core-shell structure are core-shell structures which comprise siloxane and / or carbosilane units in the dendritic core, linear unbranched alkylene groups as connecting chain, oligothiophene chain unsubstituted as linear conjugated oligomeric chains and / or oligo (3, 4-ethylenedioxythiophene) chains having 2 to 8, preferably 4 to 6 optionally substituted thiophene or 3,4-ethylenedioxythiophene input units and C 6 ⁇ C contained 2 -AIkyl fate as flexible non-conjugated chains.
- Preferred embodiments of the oligomeric compounds of the general formula (M) are those which optionally substituted as linear conjugated oligomeric chains (L) thiophene units, particularly preferably optionally substituted O ⁇ igothiophenketten and / or oligo (3,4-ethylendioxythiophen) chains having 2 to 8 Thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b), particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b).
- the oligomeric compounds of the general formula (M) contain as unconjugated chains R A and R B identical or different, linear or branched C) -C) 2 - alkylene groups and as the terminal group X A and X B hydrogen ,
- Y represents, in the case of the oligomeric compounds of the general formula (M), a carbonate, ether or a two-membered disiloxane group, more preferably an ethereal or divalent disiloxane group.
- a very particularly preferred embodiment of the invention contains oligomeric compounds of the general formula (M) in which n is 1.
- Preferred embodiments of the present invention are mixtures comprising one or more compounds of the general formula (Z) and one or more compounds of the general formula (M) in a weight ratio of from 1:99 to 99: 1, preferably 10:90 to 90:10 to which the components of the formulas (Z) and (M) linear oligomeric chains (L) having the same units, preferably linear oligomeric chains having 2 to 8 thiophene or 3,4-ethylene dioxythiophene units of the general formula (VI-a ) or (VI-b) "very particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b).
- mixtures comprising one or more compounds of the general formula (Z) and one or more compounds of the general formula (M) in a weight ratio of from 1:99 to 99: 1, preferably 10:90 to 90:10, in which the components of the formulas (Z) and (M) linear oligomeric chains (L) having the same number of identical units in the oligomeric chains, preference is given to those linear oligomeric chains having 2 to 8 thiophene or 3,4-ethylenedioxythiophene units of the general formula ( VI-a) or (VI-b), very particularly preferably 4 to 6 thiophene »or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b).
- Preferred embodiments of the monomeric linear compounds of the general formula (P) are those which contain optionally substituted thiophene units as linear conjugated oligomeric chains (L), preferably optionally substituted oligothiophene chains and / or oligo (3,4-ethylenedioxythio) phenols and / or thiophene-phenylene chains with 2 to 8 aromatic units of the general formula (VI-a), (VI-b) or (VI-c), very particularly preferably 4 to 6 aromatic units consisting of thiophene or 3,4-ethylenedioxythiophene, or Have thiophene-phenylene chains of the general formula (V ⁇ -a), (VI-b) or (VI-c).
- the compounds of the general formula (P) as nonconjugated chains R c and R D contain identical or different, linear or branched C] - Cir alkylene groups and as the terminal group X c and X D hydrogen.
- the compounds P-I, P-II and P-EU are known, for example, from Chem. Mater. (1998), Vol. 10, p. 457, J. Mater. Chem. (2003), Vol. 13, p. 197, J. Am. Chem. Soc. (2005), Vol. 127, p. 1348 and EP-A-1 531 155.
- a preferred embodiment of the present invention are mixtures comprising one or more compounds of the general formula (M) and one or more compounds of the general formula (P) in a weight ratio of from 1:99 to 99: 1, preferably from 20:80 to 80:20, in which the components of the formulas (M) and (P) have linear oligomeric chains (L) with identical units, preferably linear oligomeric chains with 2 to 8 thiophene or 3,4-ethylene-dioxythiophene units of the general formula (VI) a) or (VI-b), very particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b).
- mixtures comprising one or more compounds of the general formula (M) and one or more compounds of the general formula (P) in a weight ratio of 1:99 to 99: 1, preferably 20:80 to 80:20, in which the components of the formulas (M) and (P) linear oligomeric chains (L) with the same number of ⁇ ⁇ U - same units in the oligomeric chains, preferably those linear oligomeric chains having 2 to 8, most preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI ⁇ b ) exhibit.
- Another object of the invention are mixtures containing at least one oligomeric compound of the general formula (M), at least one macromolecular compound having a core-shell structure and at least one compound of the general formula (P).
- the abovementioned preferred ranges apply to the respective compounds of the general formula (M), (P) and (Z).
- Preferred embodiments of the present invention are mixtures comprising one or more compounds of the general formula (Z), one or more compounds of the general formula (M) and one or more compounds of the general formula (P) in a weight ratio of from 1:99 to 99: 1 , preferably 10:90 to 90:10, in which the components of the formulas (Z), (M) and (P) are linear oligomeric chains (L) having the same units, preferably linear oligomeric chains having 2 to 8 thiophene or 3 , 4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b), very particularly preferably 4 to 6 thiophene or 3,4-ethylene-dioxythiophene units of the general formula (VI-a) or ( VI-b).
- mixtures comprising one or more compounds of the general formula (Z), one or more compounds of the general formula (M) and one or more compounds of the general formula (P) in a weight ratio of 1:99 to 99: 1, preferably 10 : 90 to 90:10 wherein the components of formulas (Z), (M) and (P) are linear oligomeric chains (L) of equal number of equal units in the oligomeric chains, preferably those linear oligomeric chains of 2 to 8 Thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b), very particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a ) or (VI-b).
- weight ratios in a mixture according to the invention are to be understood, for example, as meaning that one or more compounds of the general formula (Z) and one or more compounds of the general formula (M) together have a weight fraction of 1 and one or more compounds of the general formula ( P) form 99 parts by weight of the mixture.
- Yet another object of the invention are mixtures containing at least one compound of the general Fo ⁇ nel (P) and at least one macromolecular compound having a core-shell structure, wherein the core has a MakromoJekuIare basic structure based on silicon and / or carbon and having at least 3 on a carbon-based linking chain is linked to carbon-based linear oligomeric chains having contiguous conjugated double bonds, and wherein the linear conjugated chains are each is saturated with at least one other, in particular aliphatic, araliphatic or oxyaliphatic chain without conjugated double bonds.
- the abovementioned preferred ranges apply to the respective compounds of the general formula (P) and (Z).
- Preferred embodiments of the present invention are mixtures comprising one or more compounds of the general formula (Z), and one or more compounds of the general formula (P) in a weight ratio of 1:99 to 99: 1, preferably 20:80 to 80:20, in which the components of the formulas (Z) and (P) have linear oligomeric chains (L) with identical units, preferably linear oligomeric chains with 2 to 8 thiophene or 3,4-ethylene-dioxythiophene units of the general formula (VI) a) or (VI-b), very particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythlophene units of the general formula (VI-a) or (VI-b).
- mixtures comprising one or more compounds of the general formula (Z) and one or more compounds of the general formula (M) and (P) in a weight ratio of from 1:99 to 99: 1, preferably from 20:80 to 80:20, in which the components of the formulas (Z), (M) and (P) are linear oligomeric chains (L) having the same number of identical units in the oligomeric chains, preferably those linear oligomeric chains having 2 to 8 thiophene or 3,4 -Ethylenedioxythiophene units of the general formula (VI-a) or (VI-b), very particularly preferably 4 to 6 thiophene or 3,4-ethylenedioxythiophene units of the general formula (VI-a) or (VI-b) exhibit.
- Layers of the inventive oligomeric compounds of the general formula (M) and layers of the inventive mixtures containing the oligomeric compounds of the general formula (M) and the macromolecular compounds with core-shell structure and / or the monomeric linear compounds of the general formula (P ) and layers containing the macromolecular compounds having a core-shell structure and monomeric linear compounds of the general formula (P) are preferably conductive or semiconducting.
- Particularly preferred subject matter of the invention are those layers of the compounds or mixtures which are semiconducting.
- Particular preference is given to those layers of the compounds or mixtures which have a mobility for charge carriers of at least 10.sup.- 4 cmWs.Coads are, for example, positive hole charges.
- the compounds according to the invention and mixtures are typically readily soluble in common organic solvents and thus excellent for processing
- solvents are aromatics, ethers or halogenated aliphatic hydrocarbons, such as, for example, chloroform, toluene, benzene, xylenes,
- inventive oligomeric compounds of the general formula (M) and mixtures thereof with macromolecular compounds having a core-shell structure and / or compounds of the general formula (P) or mixtures of compounds of the general formula (P) with macromolecular compounds with nuclear Shell structure for example, over the known monomeric compounds has the advantage that an increased solubility in the common organic solvents is achieved. This facilitates the processing of the connections to semiconductor layers.
- the general formula (P) can be carried out by co-dissolving in the corresponding solvents.
- the dissolution process is preferably carried out in the heat.
- the solutions obtained are stable and processable.
- the mixture of the components can be prepared by adding one component during the preparation of the other component, for example adding the monomeric compounds of the general formula (P) during the synthesis of the oligomeric compounds of the general formula (M), or addition of the oligomeric compounds of the general formula (M) during the synthesis of the macromolecular compounds with core-shell structure, so that the erfmdungshacke ⁇ mixtures are obtained in the isolation.
- the mixtures according to the invention can furthermore be prepared by combining solutions of the individual components on a suitable substrate.
- the substrate may be, for example, a structured silicon wafer or a coated glass substrate, for example coated with ITO.
- the individual components of the mixtures according to the invention can be prepared for example by separate dripping, beispielswise by an ink-jet printing process, on the substrate.
- Another method is, for example, the preparation of the mixtures according to the invention by simultaneous or successively separate metering of the individual components onto the substrate during spin-coating.
- the preparation route is not significant for the properties of the compounds and mixtures according to the invention.
- the compounds of the invention and mixtures are prepared in common solvents, e.g. Aromatics, ethers or halogenated aliphatic hydrocarbons, e.g. in chloroform, toluene, benzene, xylene, diethyl ether, dichloromethane, chbrbenzene, dichlorobenzene or tetrahydrofuran, to at least 0.1 wt .-%, preferably at least 1 wt .-%, more preferably at least 5 wt .-% soluble.
- solvents e.g. Aromatics, ethers or halogenated aliphatic hydrocarbons, e.g. in chloroform, toluene, benzene, xylene, diethyl ether, dichloromethane, chbrbenzene, dichlorobenzene or tetrahydrofuran
- the compounds and mixtures according to the invention form high-quality layers of uniform thickness and morphology from evaporated solutions and are therefore suitable for electronic applications.
- the invention furthermore relates to the use of the compounds according to the invention and mixtures as semiconductors in electronic components such as field-effect transistors, light-emitting components such as organic light-emitting diodes or photovoltaic cells, lasers and sensors.
- electronic components such as field-effect transistors, light-emitting components such as organic light-emitting diodes or photovoltaic cells, lasers and sensors.
- the compounds according to the invention and mixtures in the form of layers are preferably used for this purpose.
- the compounds and mixtures according to the invention have sufficient mobility, for example at least 10.sup.- 4 cm.sup.s.sup.th charge mobilities can be obtained, for example, as in M. Pope and CE Swenberg, Electronic Processes in Organic Crystals and Polymers, 2nd Ed , Pp. 709-713 (Oxford University Press, New York Oxford 1999).
- the compounds according to the invention and mixtures are applied to suitable substrates, for example silicon wafers provided with electrical or electronic structures, polymer films or glass panes. In principle, all order methods can be considered for the order.
- the compounds according to the invention and mixtures of liquid phase, ie from solution, applied and the solvent is then evaporated.
- the application from solution can be carried out by the known methods, for example by spraying, dipping, printing and knife coating. Particularly preferred is the application by spin coating and by ink-jet printing.
- the layers made from the compounds of the invention and mixtures may be further modified after application, for example by a thermal treatment, e.g. while passing through a liquid crystalline phase or for structuring e.g. by laser ablation.
- the invention furthermore relates to electronic components comprising the compounds according to the invention and mixtures as semiconductors.
- the compounds of the formula Z were prepared by known processes from, for example, EP-A 1 580 217 and Chem. Mater. 2006, Volume 18, p. 4101.
- the compounds of the formula P were prepared by known processes from, for example, EP-A 1 439 173, J. Mater, Chem. 2003, Vol. 13, p. 197, Synthesis 1993, p.1099 or Chem. Mater. 1993, Volume 5, p. 430 synthesized.
- the compounds of the formula (M) according to the invention can be prepared analogously to the syntheses as shown in Examples 1-3.
- One-side polished p-type silicon wafers with a thermally grown oxide layer of 300 nm thickness were cut into 25 mm x 25 mm substrates.
- the substrates were first carefully cleaned.
- the adherent silicon Spfitter were removed by rubbing with a clean room cloth (Bemot M-3, Ashaih Kasei Corp.) under running distilled water and then the substrates in an aqueous 2% water / Mucasol solution at 60 0 C 15 minutes long in Ullraschallbad cleaned. Thereafter, the substrates were rinsed with distilled water and spun dry in a centrifuge. Immediately prior to coating, the polished surface was cleaned in a UV / ozone reactor (PR-100, UVP Inc., Cambridge, UK) for 10 minutes.
- UV / ozone reactor PR-100, UVP Inc., Cambridge, UK
- ODMC Octyidimethylchlorosilane
- Hexamethyldisilazane (Aldrich, 37921-2) was poured into a beaker containing the magazine with the upright, cleaned Si substrates. The silazane completely covered the substrates. The beaker was covered and placed on a Heating plate heated to 70 0 C. The substrates remained for 24 hrs. in silazane, then the substrates were dried in a dry stream of nitrogen.
- ODMC is used as the interlayer dielectric; in the case that the use of HMDS as a dielectric interlayer takes place, it is explicitly pointed out.
- a solution of the compounds in a suitable solvent was prepared.
- the solution was placed for about 1 min in an ultrasonic bath at 60 0 C.
- the concentration of the solution was 0.3% by weight.
- the substrate provided with the dielectric interlayer was placed with the polished side up in the holder of a spin coater (Carl Süss, RC 8 with Gyrset®) and heated with a hair dryer to about 70 0 C. Approximately 1 ml of the still warm solution was dropped onto the surface and the solution was spun off with the organic semiconductor at 1200 rpm for 30 sec at an acceleration of 500 U / sec 2 and open Gyrset® on the substrate. The film thus produced was dried on a hot plate at 70 0 C for 3 min. The layer was homogeneous and had no haze.
- a spin coater Carl Süss, RC 8 with Gyrset®
- a shadow mask was used, which consisted of a galvanically produced Ni foil with 4 recesses of two intermeshing combs.
- the teeth of the individual combs were 100 ⁇ m wide and 4.7 mm long.
- the mask was placed on the surface of the coated substrate and fixed with a magnet from the back.
- the substrates were vapor-deposited with gold.
- the electrode structure thus produced had a length of 14.85 cm at a distance of 100 microns.
- the electrical capacitance of the devices was determined by evaporating an identically prepared substrate, but without an organic semiconductor layer, in parallel behind the same shadow masks.
- the capacitance between the p-doped silicon wafer and the deposited electrode was determined with a multimeter, MetraHit 18S, Gossen Metrawatt GmbH).
- the characteristic curves were measured by means of two Slom voltage sources (Keithley 238).
- the one voltage source applies an electrical potential to the source and drain, thereby determining the flowing current, while the second sets an electrical potential at the gate and source.
- the source and drain were contacted with pressed-on Au-St ⁇ ften, the highly doped Si wafer formed the gate electrode and was contacted via the back scratched by the oxide.
- the recording of the characteristic curves and their evaluation was carried out according to the known method, such as e.g. described in "Organic thin-film transistor: A review of recent advances", C.D. Dimitrakopoulos, D.J. Mascaro, IBM J. Res. & Dev. Vol.45 No. 1 January 2001.
- a solution containing the compound of the formula (P-I) and the compound of the formula (M-VI) in a weight ratio of 1: 2 was prepared in a mixture of one part by volume of chloroform and one part by volume of toluene.
- the substance mixture gave optically homogeneous films. The mixture remains stable even with prolonged storage in air as shown in FIG. 14.
- a solution containing the compound of the formula (P-I) and the compound of the formula (M-VO) in a weight ratio of 1: 2 was prepared in a mixture of a Vo ⁇ umenteil chloroform and one part by volume of toluene.
- the substance mixture gave optically homogeneous films.
- organic dielectric layer hexamethyldisilazane was used.
- organic semiconductor a solution of the compound (Z-4-a-1) and the compound of Fonnel (P-I) was used.
- a solution of the compound (Z-4-al) 3 of the compound (M-VI) and the compound (PI) in a weight ratio of 13: 2: 5 was prepared in a mixture of one volume of chloroform and one volume of toluene. Homogeneous films of optically good quality were obtained.
- Table 1 summarizes the results of the transistor measurements.
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Abstract
Description
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Application Number | Priority Date | Filing Date | Title |
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DE102006043039A DE102006043039A1 (en) | 2006-09-14 | 2006-09-14 | Semiconductor layers forming mixtures of organic compounds |
PCT/EP2007/059506 WO2008031813A2 (en) | 2006-09-14 | 2007-09-11 | Oligomeric compounds which form a semiconductor layer |
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EP2066722A2 true EP2066722A2 (en) | 2009-06-10 |
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EP07820116A Withdrawn EP2066722A2 (en) | 2006-09-14 | 2007-09-11 | Oligomeric compounds which form a semiconductor layer |
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US (1) | US20090283723A1 (en) |
EP (1) | EP2066722A2 (en) |
JP (1) | JP2010503635A (en) |
KR (1) | KR20090057265A (en) |
DE (1) | DE102006043039A1 (en) |
TW (1) | TW200837095A (en) |
WO (1) | WO2008031813A2 (en) |
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DE102008014158A1 (en) * | 2008-03-14 | 2009-09-17 | H.C. Starck Gmbh | Novel macromolecular compounds having a core-shell structure for use as semiconductors |
DE102011009415A1 (en) * | 2011-01-25 | 2012-07-26 | Heraeus Precious Metals Gmbh & Co. Kg | Star-shaped compounds for organic solar cells |
US10293368B2 (en) * | 2015-04-20 | 2019-05-21 | Sharp Kabushiki Kaisha | Film-forming method |
US10050203B2 (en) | 2016-05-27 | 2018-08-14 | Samsung Electronics Co., Ltd. | Polymer and electronic device and organic thin film transistor including the same |
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US4435548A (en) * | 1981-04-27 | 1984-03-06 | The Dow Chemical Company | Branched polyamidoamines |
US4507466A (en) * | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
US4631337A (en) * | 1983-01-07 | 1986-12-23 | The Dow Chemical Company | Hydrolytically-stable dense star polyamine |
US5145930A (en) * | 1987-12-07 | 1992-09-08 | E. I. Du Pont De Nemours And Company | Preparation of hyperbranched polyarylenes |
US5070183A (en) * | 1987-12-07 | 1991-12-03 | E. I. Du Pont De Nemours And Company | Hyperbranched polyarylene |
US5183862A (en) * | 1990-06-22 | 1993-02-02 | E. I. Du Pont De Nemours And Company | Hyperbranched polyesters |
US5270402A (en) * | 1990-06-22 | 1993-12-14 | E. I. Du Pont De Nemours And Company | Hyperbranched polyesters |
US5264543A (en) * | 1991-10-30 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Hyperbranched aramid |
JP3355612B2 (en) * | 1992-04-14 | 2002-12-09 | 株式会社豊田中央研究所 | Star-shaped nylon and its production method, and tetrasubstituted carboxylic acid and its production method |
US5225522A (en) * | 1992-07-13 | 1993-07-06 | Eastman Kodak Company | Multiply-branched aliphatic-aromatic polyesters and method for preparing multiply-branched aliphatic-aromatic polyesters |
US6025462A (en) * | 1997-03-06 | 2000-02-15 | Eic Laboratories, Inc. | Reflective and conductive star polymers |
US6384172B1 (en) * | 2001-01-02 | 2002-05-07 | Michigan Molecular Institute | Hyperbranched polycarbosilanes, polycarbosiloxanes, polycarbosilazenes and copolymers thereof |
EP1279690A1 (en) * | 2001-07-25 | 2003-01-29 | MERCK PATENT GmbH | Mono-oligo- and poly-3-substituted-4-fluorothiophenes and their use as charge transport materials |
AU2003235181A1 (en) * | 2002-04-22 | 2003-11-03 | Konica Minolta Holdings, Inc. | Organic semiconductor composition, organic semiconductor element, and process for producing the same |
DE50309671D1 (en) * | 2002-09-13 | 2008-06-05 | Starck H C Gmbh | Organic compounds with core-shell structure |
DE10248876B4 (en) * | 2002-10-18 | 2006-07-06 | H.C. Starck Gmbh | Process for the preparation of linear organic oligomers |
DE10353093A1 (en) * | 2003-11-12 | 2005-06-16 | H.C. Starck Gmbh | Unsymmetrical linear organic oligomers |
DE10353094A1 (en) * | 2003-11-12 | 2005-06-09 | H.C. Starck Gmbh | Process for preparing linear organic thiophene-phenylene oligomers |
DE102004014621A1 (en) * | 2004-03-25 | 2005-10-13 | H.C. Starck Gmbh | Organic compounds with core-shell structure |
JP2007311569A (en) * | 2006-05-18 | 2007-11-29 | Hiroshima Univ | Silicon-cross-linked thiophene oligomer and electronic device using the same |
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2006
- 2006-09-14 DE DE102006043039A patent/DE102006043039A1/en not_active Withdrawn
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2007
- 2007-09-11 EP EP07820116A patent/EP2066722A2/en not_active Withdrawn
- 2007-09-11 JP JP2009527804A patent/JP2010503635A/en active Pending
- 2007-09-11 US US12/441,153 patent/US20090283723A1/en not_active Abandoned
- 2007-09-11 WO PCT/EP2007/059506 patent/WO2008031813A2/en active Application Filing
- 2007-09-11 KR KR1020097005833A patent/KR20090057265A/en not_active Application Discontinuation
- 2007-09-13 TW TW096134144A patent/TW200837095A/en unknown
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JP2010503635A (en) | 2010-02-04 |
TW200837095A (en) | 2008-09-16 |
US20090283723A1 (en) | 2009-11-19 |
WO2008031813A2 (en) | 2008-03-20 |
DE102006043039A1 (en) | 2008-03-27 |
KR20090057265A (en) | 2009-06-04 |
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