WO2013010661A1 - Sam layers with an htl function - Google Patents
Sam layers with an htl function Download PDFInfo
- Publication number
- WO2013010661A1 WO2013010661A1 PCT/EP2012/002989 EP2012002989W WO2013010661A1 WO 2013010661 A1 WO2013010661 A1 WO 2013010661A1 EP 2012002989 W EP2012002989 W EP 2012002989W WO 2013010661 A1 WO2013010661 A1 WO 2013010661A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- layer
- layered body
- tetraarylbenzidine
- polythiophene
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 41
- 230000008569 process Effects 0.000 claims abstract description 29
- 150000003254 radicals Chemical class 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 179
- 229920000123 polythiophene Polymers 0.000 claims description 47
- -1 poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 46
- 238000002347 injection Methods 0.000 claims description 37
- 239000007924 injection Substances 0.000 claims description 37
- 229920001940 conductive polymer Polymers 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 19
- 239000013545 self-assembled monolayer Substances 0.000 claims description 18
- 239000006185 dispersion Substances 0.000 claims description 16
- 239000002094 self assembled monolayer Substances 0.000 claims description 14
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 13
- 239000002270 dispersing agent Substances 0.000 claims description 10
- 229920000144 PEDOT:PSS Polymers 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920000447 polyanionic polymer Polymers 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- HBPVGJGBRWIVSX-UHFFFAOYSA-N 6-bromohexanoyl chloride Chemical compound ClC(=O)CCCCCBr HBPVGJGBRWIVSX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000867 polyelectrolyte Polymers 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- 0 CC(N(c(c(*)c1*c2c3*)c(*)c(*4)c1-c2c4c(*)c3N(*)*1*C1)N=C)=O Chemical compound CC(N(c(c(*)c1*c2c3*)c(*)c(*4)c1-c2c4c(*)c3N(*)*1*C1)N=C)=O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001398 aluminium Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JDAAOTPJKFEHLO-UHFFFAOYSA-N n-[4-(4-anilinophenyl)phenyl]-4-(6-bromohexyl)-n-phenylnaphthalen-1-amine Chemical compound C12=CC=CC=C2C(CCCCCCBr)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(NC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 JDAAOTPJKFEHLO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives, a layered body, a process for the production of a layered body, the layered body obtainable by this process, electronic components comprising a layered body and the use of an ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative.
- An electroluminescent arrangement is characterized in that when an electrical voltage is applied, it emits light with a flow of current.
- Such arrangements have been known for a long time by the name “light-emitting diodes” (LEDs).
- LEDs light-emitting diodes
- the emission of light arises by positive charges (holes) and negative charges (electrons) recombining with the emission of light.
- LEDs customary in the art are all made predominantly of inorganic semiconductor materials.
- EL arrangements of which the essential constituents are organic materials have been known for some years.
- OLED organic light-emitting diode
- the main layer configuration of an EL arrangement is e.g. as follows:
- an EL arrangement consists of two electrodes, between which is an organic layer which fulfils all the functions - including the emission of light.
- the polymerization of EDOT is carried out in an aqueous solution of the polyanion, and a polyelectrolyte complex is formed.
- Cationic polythiophenes which contain polymeric anions as counter-ions for charge compensation are also often called polythiophene/polyanion complexes in the technical field. Due to the polyelectrolyte properties of PEDOT as a polycation and PSS as a polyanion, this complex in this context is not a true solution, but rather a dispersion.
- NPB bis(l-naphthyl)-N,N'-diphenylbenzidine
- the present invention was based on the object of overcoming the disadvantages resulting from the prior art in connection with OLEDs, in particular in connection with OLEDs which include hole injection layers comprising conductive polymers, in particular hole injection layers comprising polythiophenes and polyanions functional ized with acid groups.
- the present invention was based on the object of providing compounds which are suitable as a hole transport or electron blocking layer, in particular on a hole injection layer comprising PEDOT/PSS, and which as far as possible are not washed off from this PEDOT/PSS layer when further layers, for example an emitter layer, are deposited on this hole transport or electron blocking layer from aqueous or organic solutions.
- the present invention was furthermore based on the object of providing a layered body comprising a hole injection layer and a hole transport and/or electron blocking layer, the hole injection layer comprising conductive polymers, in particular conductive polymers comprising polythiophenes and polyanions functionalized with acid groups.
- the hole transport and/or electron blocking layer should as far as possible not be washed off from the hole injection layer when further layers, for example an emitter layer, are deposited on this hole transport or electron blocking layer from aqueous or organic solutions.
- the present invention was also based on the object of providing a process for the production of a layered body which renders possible the production of hole injection layers comprising conductive polymers, in particular conductive polymers including polythiophenes and polyanions functionalized with acid groups, followed by a hole transport and/or electron blocking layer by means of process measures which are as simple as possible.
- a contribution towards achieving the abovementioned objects is made by ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives of the general formula (I)
- R can in each case be identical or different and in each case represents a hydrogen atom, a halogen atom, or an optionally substituted, straight-chain or branched Ci-C3o-alkyl group,
- Ar can in each case be identical or different and represents an optionally mono- or polysubstituted aryl radical, wherein at least one of the aryl radicals is substituted by at least one radical -R -NR 2 R 3 , in which — R 1 represents a straight-chain or branched C 2 -C 20 -alkylene radical, particularly preferably a straight-chain or branched C 3 -Ci5-alkylene radical and most preferably a straight-chain or branched C4-C 10 - alkylene radical and R and R can be identical or different and in each case represent a hydrogen atom or a d-Cs-alkyl group, but particularly preferably a hydrogen atom.
- ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives of the general formula (I) can form a self-assembled monolayer (SAM) on a surface of a conductive polymer, in particular on a surface of a conductive polymer comprising a polythiophene and a polymer functionalized with acid groups, for example on a PEDOT : PSS surface, and an SAM layer of these ⁇ , ⁇ , ⁇ ', ⁇ '- tetraarylbenzidine derivatives can be employed, for example, as a hole transport layer in an OLED.
- SAM self-assembled monolayer
- ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives according to the invention, these have the general formula (II) in which R 4 and R 5 correspond to the radical R, as defined above, with the proviso that at least one of the radicals R 4 represents a radical -R'-NR 2 R 3 , as likewise defined above.
- R 4 and R 5 correspond to the radical R, as defined above, with the proviso that at least one of the radicals R 4 represents a radical -R'-NR 2 R 3 , as likewise defined above.
- R 4 and R 5 correspond to the radical R, as defined above, with the proviso that at least one of the radicals R 4 represents a radical -R'-NR 2 R 3 , as likewise defined above.
- R 4 and R 5 correspond to the radical R, as defined above, with the proviso that at least one of the radicals R 4 represents a radical -R'-NR 2 R 3 , as likewise defined above.
- R 4 and R 5 correspond
- R represents a radical -R -NR R as defined above.
- R 4 represents a radical -R ! -NR 2 R 3 as defined above.
- R 1 represents a C 2 -Ci 0 - alkylene group, in particular -(C H ]2 )-, and for R and R to represent a hydrogen atom.
- a contribution towards achieving the abovementioned objects is also made by a layered body comprising at least - a first layer comprising a conductive polymer; a further layer following the first layer, comprising an ⁇ , ⁇ , ⁇ ', ⁇ '- tetraarylbenzidine derivative according to the invention.
- the layered body according to the invention comprises a first layer which comprises a conductive polymer and which preferably serves as a hole injection layer.
- a conductive polymer in this context are all polymers which have an electrical conductivity, such as, for example, conductive polymers based on optionally substituted polyanilines, optionally substituted polypyrroles or optionally substituted polythiophenes, conductive polymers based on optionally substituted polythiophenes being particularly preferred.
- the conductive polymer in the first layer comprises a preferably cationic polythiophene and a preferably anionic polymer functionalized with acid groups.
- the polythiophene is preferably a polythiophene with recurring units of the general formula (i) or (ii) or a combination of units of the general formulae (i) and (ii), preferably a polythiophene with recurring units of the general formula (ii) wherein
- A represents an optionally substituted Ci-Cs-alkylene radical
- R represents a linear or branched, optionally substituted Q-ds-alkyl radical, an optionally substituted C 5 -C 12 -cycloalkyl radical, an optionally substituted C 6 -C 14 -aryl radical, an optionally substituted C 7 -C 18 -aralkyl radical, an optionally substituted C 1 -C 4 -hydroxyalkyl radical or a hydroxyl radical, x represents an integer from 0 to 8 and in the case where several radicals R are bonded to A, these can be identical different.
- Polythiophenes with recurring units of the general formula (ii) wherein A represents an optionally substituted C 2 -C 3 -alkylene radical and x represents 0 or 1 are particularly preferred.
- Poly(3,4-ethylenedioxythiophene), which is optionally substituted, is very particularly preferred as the polythiophene.
- the prefix poly- is to be understood as meaning that the polymer or polythiophene contains more than one identical or different recurring units of the general formulae (i) and (ii).
- the polythiophenes can optionally also comprise other recurring units, but it is preferable for at least 50%, particularly preferably at least 75% and most preferably at least 95% of all recurring units of the polythiophene to have the general formula (i) and/or (ii), preferably the general formula (ii).
- the polythiophenes contain a total of n recurring units of the general formula (i) and/or (ii), preferably of the general formula (ii), wherein n is an integer from 2 to 2,000, preferably 2 to 100.
- the recurring units of the general formula (i) and/or (ii), preferably of the general formula (ii), can in each case be identical or different within a polythiophene.
- Polythiophenes with in each case identical recurring units of the general formula (ii) are preferred.
- the polythiophenes preferably in each case carry H on the end groups.
- Cj-Cs-alkylene radicals A are preferably methylene, ethylene, n-propylene, n-butylene or n-pentylene.
- C]-C 18 -alkyl radicals preferably represent linear or branched Ci-Ci 8 -alkyl radicals, such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, 1 -methyl butyl, 2-methylbutyl, 3-methylbutyl, 1 -ethylpropyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n- nonyl, n-decyl, n-undecyl, n-do
- radicals A and/or of the radicals R for example alkyl, cycloalkyl, aryl, aralkyl, alkoxy, halogen, ether, thioether, disulphide, sulphoxide, sulphone, sulphonate, amino, aldehyde, keto, carboxylic acid ester, carboxylic acid, carbonate, carboxylate, cyano, alkylsilane and alkoxysilane groups and carboxamide groups.
- the polythiophenes can be neutral or cationic. In preferred embodiments they are cationic, "cationic" relating only to the charges on the polythiophene main chain.
- the polythiophenes can carry positive and negative charges in the structural unit, depending on the substituent on the radicals R, the positive charges being on the polythiophene main chain and the negative charges optionally being on the radicals R substituted by sulphonate or carboxylate groups.
- the positive charges of the polythiophene main chain can be partly or completely satisfied by the anionic groups optionally present on the radicals R. Overall, in these cases the polythiophenes can be cationic, neutral or even anionic.
- the positive charges on the polythiophene main chain are the deciding factor.
- the positive charges are not shown in the formulae, since their precise number and position cannot be determined absolutely. However, the number of positive charges is at least 1 and at most n, where n is the total number of all recurring units (identical or different) within the polythiophene.
- the first layer furthermore comprises a polyanion based on polymers functionalized with acid groups.
- Anions of polymeric carboxylic acids such as polyacrylic acids, polymethacrylic acid or polymaleic acids, or of polymeric sulphonic acids, such as polystyrenesulphonic acids and polyvinylsulphonic acids, are possible in particular as the polyanion.
- These polycarboxylic and -sulphonic acids can also be copolymers of vinylcarboxylic and vinylsulphonic acids with other polymerizable monomers, such as acrylic acid esters and styrene.
- the first layer contains an anion of a polymeric carboxylic or sulphonic acid for compensation of the positive charge of the polythiophene.
- PSS polystyrenesulphonic acid
- a polythiophene which, if a polythiophene is used, in particular poly(3,4-ethylenedioxythiophene), is preferably present bonded as a complex in the form of the PEDOT : PSS complexes known from the prior art, is particularly preferred as the polyanion.
- Such complexes are obtainable by polymerizing the thiophene monomers, preferably 3,4-ethylenedioxythiophene, oxidatively in aqueous solution in the presence of polystyrenesulphonic acid.
- the molecular weight of the polymers functionalized with acid groups which supply the polyanions is preferably 1,000 to 2,000,000, particularly preferably 2,000 to 500,000.
- the polymers functionalized with acid groups or their alkali metal salts are commercially obtainable, e.g. polystyrenesulphonic acids and polyacrylic acids, or can be prepared by known processes (see e.g. Houben Weyl, Methoden der organischen Chemie, vol. E 20 Makromolekulare Stoffe, part 2, (1987), p. 1 141 et seq.).
- Polymers functionalized with acid groups (polyanions) and polythiophenes, in particular polystyrenesulphonic acid and poly(3,4-ethylenedioxythiophene), can be present in the first layer in a weight ratio of from 0.5 : 1 to 50 : 1, preferably from 1 : 1 to 30 : 1, particularly preferably 2 : 1 to 20 : 1.
- the weight of the electrically conductive polymers here corresponds to the weight of the monomers employed for the preparation of the conductive polymers, assuming that complete conversion takes place during the polymerization.
- the polystyrenesulphonic acid is present in an excess by weight compared with the polythiophene, in particular compared with poly(3,4-ethylenedioxythiophene).
- the first layer consists of the polythiophene and the polymer functionalized with acid groups, particularly preferably PEDOT : PSS, to the extent of at least 40 wt.%, particularly preferably to the extent of at least 55 wt.% and most preferably to the extent of at least 70 wt.%, in each case based on the total weight of the first layer.
- the layer thickness of the first layer is preferably in a range of from 1 nm to 10 ⁇ , particularly preferably in a range of from 10 nm to 500 nm and most preferably in a range of from 20 nm to 200 nm.
- the layered body according to the invention comprises a further layer which follows the first layer and comprises the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative according to the invention described above, it being particularly preferable according to the invention for this further layer to be a layer which forms a self-assembled monolayer (SAM).
- SAM self-assembled monolayer
- a self- assembled monolayer in general forms spontaneously when a substrate is immersed in a fluid comprising the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative. It is an organized layer of amphiphilic molecules, one end of the particular molecules having a specific, reversible affinity for a substrate.
- SAMs have a defined layer thickness, conventionally a layer thickness in the range of from approximately 0.5 to 3 nm.
- a contribution towards achieving the abovementioned objects is also made by a process for the production of a layered body, comprising the process steps i) application of a conductive polymer to a substrate to obtain a first layer; ii) application of an ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative according to the invention.
- a conductive polymer is applied to a substrate to obtain a first layer.
- Possible substrates in this context are all layers which can be employed in electronic components, such as, for example, an OLED.
- the substrate can thus be in particular a substrate which is provided with a preferably transparent base electrode and is preferably likewise transparent.
- the transparent substrate which can be employed in this context is glass, PET or other transparent plastics, for example, on to which a transparent electrically conductive electrode, such as e.g. an electrode of indium tin oxide (ITO), doped zinc oxide or tin oxide or a conductive polymer, is then applied.
- a transparent electrically conductive electrode such as e.g. an electrode of indium tin oxide (ITO), doped zinc oxide or tin oxide or a conductive polymer
- transparent substrates of plastic are, for example, polycarbonates, polyesters, such as e.g.
- PET and PEN polyethylene terephthalate or polyethylene-naphthalene dicarboxylate
- copolycarbonates polyacrylates, polysulphones, polyether sulphones (PES), polyimides, polyethylene, polypropylene, cyclic polyolefins or cyclic olefin copolymers (COC), hydrogenated styrene polymers or hydrogenated styrene copolymers.
- Suitable polymer substrates can also be, for example, films, such as polyester films, PES films from Sumitomo or polycarbonate films from Bayer AG (Makrofol ® ). Glass coated with ITO is particularly preferred according to the invention as the substrate.
- the conductive polymer is applied to such a substrate or also the electrode layer applied to such a substrate to obtain the first layer of the layered body according to the invention, those conductive polymers which have already been mentioned above as the preferred conductive polymer in connection with the layered body according to the invention being particularly preferred as the conductive polymer.
- a conductive polymer comprising a polythiophene, particularly preferably PEDOT, and a polymer fiinctionalized with acid groups, particularly preferably PSS is accordingly particularly preferred according to the invention, here also the use of PEDOT : PSS complexes as the conductive polymer being very particularly preferred.
- the conductive polymer is applied to the substrate in the form of a dispersion comprising the conductive polymer and a dispersing agent, particularly preferably in the form of a dispersion comprising a polythiophene, a polymer fiinctionalized with acid groups and a dispersing agent, very particularly preferably in the form of a PEDOT : PSS dispersion, and the dispersing agent is then at least partially removed to obtain the first layer.
- a dispersing agent particularly preferably in the form of a dispersion comprising a polythiophene, a polymer fiinctionalized with acid groups and a dispersing agent, very particularly preferably in the form of a PEDOT : PSS dispersion
- the application of the dispersions can be carried out, for example, by known processes, e.g.
- the at least partial removal of the dispersing agent is preferably carried out by drying at a temperature in a range of from 20 °C to 200 °C, it possibly being advantageous to at least partially remove the supernatant dispersion from the substrate before the drying process, for example by spinning off.
- dispersions comprising a polythiophene, a polymer fiinctionalized with acid groups and a dispersing agent is described in principle in EP-A 1 122 274 or US 5, 1 11 ,327.
- the polymerization of the corresponding monomelic compounds is carried out in the presence of the polymers fiinctionalized with acid groups with suitable oxidizing agents in suitable solvents.
- suitable oxidizing agents are iron(III) salts, in particular FeCl 3 und iron(III) salts of aromatic and aliphatic sulphonic acids, H 2 0 2 , K 2 Cr 2 0 7 , K 2 S 2 0 8 , Na 2 S 2 0 8 , ⁇ 0 4 , alkali metal perborates and alkali metal or ammonium persulphates or mixtures of these oxidizing agents.
- iron(III) salts in particular FeCl 3 und iron(III) salts of aromatic and aliphatic sulphonic acids, H 2 0 2 , K 2 Cr 2 0 7 , K 2 S 2 0 8 , Na 2 S 2 0 8 , ⁇ 0 4 , alkali metal perborates and alkali metal or ammonium persulphates or mixtures of these oxidizing agents.
- suitable oxidizing agents are described, for example, in Handbook of Conducting Polymers (ed. Skotheim, T.A.), Marcel Dekker: New York,
- Particularly preferred oxidizing agents are FeCl 3 , Na 2 S 2 0 8 and 2 S 2 0 8 or mixtures of these.
- the polymerization is preferably carried out at a reaction temperature of from -20 to 100 °C. Reaction temperatures of from 20 to 100 °C are particularly preferred. If appropriate, the reaction solution is then treated with at least one ion exchanger.
- Suitable solvents are e.g. polar solvents, such as, for example, water, alcohols, such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, diacetone alcohol, ethylene glycol, glycerol or mixtures of these.
- polar solvents such as, for example, water, alcohols, such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, diacetone alcohol, ethylene glycol, glycerol or mixtures of these.
- Aliphatic ketones such as acetone and methyl ethyl ketone, aliphatic nitriles, such as acetonitrile, aliphatic and cyclic amides, such as N,N-dimethylacetamide, ⁇ , ⁇ -dimethylformamide (DMF) and 1- methyl-2-pyrrolidone (NMP), ethers, such as tetrahydrofuran (THF), and sulphoxides, such as dimethylsulphoxide (DMSO), or mixtures of these with one another or with the abovementioned solvents are likewise suitable.
- aliphatic ketones such as acetone and methyl ethyl ketone
- aliphatic nitriles such as acetonitrile
- aliphatic and cyclic amides such as N,N-dimethylacetamide, ⁇ , ⁇ -dimethylformamide (DMF) and 1- methyl-2-pyrrolidone (NMP)
- the dispersions have a solids content in a range of from 0.01 to 20 wt.% and particularly preferably in a range of from 0.2 to 5 wt.%, i.e. they contain in total 0.01 to 20 wt.%, particularly preferably 0.2 to 5 wt.% of polythiophene(s), preferably PEDOT, of polymer functionalized with acid groups, preferably PSS, and optionally further components, such as e.g. binders, crosslinking agents and/or surfactants, in dissolved and/or dispersed form.
- the viscosity at 20 °C of the dispersions employed for the preparation of the first layer is preferably between the viscosity of the dispersing agent and 200 mPas, preferably between the viscosity of the dispersing agent and 100 mPas.
- the desired amount of dispersing agent can be removed from the dispersions by distillation, preferably in vacuo, or by other processes, e.g. ultrafiltration.
- Organic, polymeric binders and/or organic, low molecular weight crosslinking agents or surfactants can moreover be added to the dispersions.
- Corresponding binders are described e.g. in EP-A 564 91 1. There may be mentioned here by way of example polyvinylcarbazole, silanes, such as Silquest ® A 187 (OSi Specialities), or surfactants, such as the fluoro-surfactant FT 248 (Bayer AG).
- an ⁇ , ⁇ , ⁇ ', ⁇ '- tetraarylbenzidine derivative according to the invention is then applied to the first layer to obtain a further layer, it being particularly preferable for an SAM to be formed on application of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative to the first layer in process step ii).
- Preferred ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives in this context are those ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives which have already been described above as preferred ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives in connection with the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative according to the invention.
- the ⁇ , ⁇ '- bis(l-naphthyl)-N,N'-diphenylbenzidine derivatives of the general formula (III) or (IV) are accordingly very particularly preferred in this connection.
- the application of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives to the first layer is preferably carried out by a procedure in which the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives are dissolved in a suitable, preferably polar solvent, for example water, an alcohol, such as, for example, methanol, ethanol, n-propanol, isopropanol, ethylene glycol or glycerol, a sulphoxide, such as, for example, dimethylsulphoxide, an ester, such as, for example, ⁇ -butyrolactone, methyl acetate or ethyl acetate, an ether, such as, for example, tetrahydrofuran or 1,4- dioxane, a ketone, such as, for example, acetone or methyl ethyl ketone, an amide, such as, for example, formamide, dimethylformamide, N-methylformamide or
- the coating is also washed once or several times with suitable solvents after the spinning off, in order to ensure that a monolayer of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative remains.
- the process conditions during application of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative to the first layer should preferably be chosen such that an SAM layer of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative is formed on the first layer comprising the conductive polymer, preferably on the layer comprising PEDOT : PSS.
- the concentration of ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative in the solution which is employed for application of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative to the first layer is preferably in a range of from 0.1 to 20 wt.%, particularly preferably in a range of from 1 to 10 wt.%, in each case based on the total weight of the solution.
- process step ii) can be followed by still further process steps, such as, for example, iii) application of an emitter layer to the hole transport layer; iv) application of an electron injection layer to the emitter layer; v) application of a cathode layer to the electron injection layer.
- the hole transport layer or the hole injection layer can also be called an electron blocking layer. If the electron injection layer has the ability to block the hole transport, the electron injection layer can also be called a hole blocking layer.
- Suitable materials for the emitter layer are conjugated polymers, such as polyphenylenevinylenes and/or polyfluorenes, for example the polyparaphenylenevinylene derivatives and polyfluorene derivatives described in WO-A-90/13148, or emitters from the class of low molecular weight emitters, also called "small molecules" in technical circles, such as aluminium complexes, such as, for example, tris(8-hydroxyquinolinato)aluminium (Alq 3 ), fluorescent dyestuffs, e.g. quinacridones, or phosphorescent emitters, such as, for example, Ir(ppy) 3 .
- Further suitable materials for the emitter layer are described e.g. in DE- A-196 27 071. Tris(8-hydroxyquinolinato)aluminium (Alq 3 ) is particularly preferred according to the invention as the emitter layer.
- metals of group IA of the periodic table which have an exit work of from 1.5 to 3.0 eV and of oxides, halides and carbonates thereof are lithium, lithium fluoride, sodium oxide, lithium oxide and lithium carbonate.
- Examples of metals of group IIA of the periodic table, excluding Ca, which have an exit work of from 1.5 to 3.0 eV and of oxides, halides and carbonates thereof are strontium, magnesium oxide, magnesium fluoride, strontium fluoride, barium fluoride, strontium oxide and magnesium carbonate.
- Suitable materials for the cathode layer are, in particular, transparent or translucent materials with a relatively low exit work (of preferably less than 4.0 eV).
- metals such as, for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), Be, magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), aluminium (Al), scandium (Sc), vanadium (V), Zn, yttrium (Y), indium (In), cerium (Ce), samarium (Sm), Eu, Tb, and ytterbium (Yb); alloys which consist of two or more of these metals; alloys which consist of one or more of these metals and one or more metals which are chosen from Au, Ag, Pt, Cu, manganese (Mn), titanium (Ti), cobalt (Co), nickel (Ni), tungsten (W) and tin (Sn); graphite
- a contribution towards achieving the abovementioned objects is also made by a layered body, particularly preferably an OLED or an OPV element, which is or are obtainable by the process according to the invention.
- an electronic component comprising a layered body according to the invention or a layered body obtainable by the process according to the invention, wherein this component is preferably an OLED or an OPV element, particularly preferably an
- the layer configuration of the OLED can have all the configurations known to the person skilled in the art, but preferably the layer sequence of hole injection layer/hole transport layer is replaced by the layered body according to the invention such that further layers of ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives according to the invention, preferably the further SAM layer of ⁇ , ⁇ , ⁇ ', ⁇ '- tetraarylbenzidine derivatives according to the invention, face the emitter layer.
- the OLED according to the invention can have any of the following layer configurations (a) to (d) as desired:
- the anode is arranged on the side of the substrate, for example glass or a transparent film of plastic, or an embodiment in which the cathode is arranged on the side of the substrate is used.
- the electron transport layer can be made of materials such as, for example, oxadiazole derivatives, anthraquinodimethane or derivatives thereof, benzoquinone or derivatives thereof, naphthoquinone or derivatives thereof, anthraquinone or derivatives thereof, tetracyanoanthraquinodimethane or derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene or derivatives thereof, diphenoquinone derivatives and metal complexes of 8- hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof or polyfluorene or derivatives thereof.
- materials such as, for example, oxadiazole derivatives, anthraquinodimethane or derivatives thereof, benzoquinone or derivatives thereof, naphthoquinone or derivatives thereof, anthraquinone or derivatives thereof, tetracyanoanthraquinodimethane or derivatives thereof, fluor
- an OLED which is built up from the following layers is particularly preferred according to the invention: anode layer/first layer of the layered body according to the invention or of the layered body obtainable by the process according to the invention/further layer of the layered body according to the invention or of the layered body obtainable by the process according to the invention/optionally emitter layer/optionally electron injection layer/cathode layer.
- a contribution towards achieving the abovementioned objects is also made by the use of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivatives of the general formula (I) according to the invention, in particular the use of the N,N'-bis(l-naphthyl)-N,N'- diphenylbenzidine derivatives of the general formula (III) or (IV) according to the invention, for the formation of an SAM in an electronic component.
- the electronic component is preferably an OLED, very particularly preferably an OLED which is built up from the following layers: anode/hole injection layer/layer of the N,N,N',N'-tetraarylbenzidine derivative according to the invention, preferably SAM layer of the ⁇ , ⁇ , ⁇ ', ⁇ '-tetraarylbenzidine derivative according to the invention/emitter layer/electron injection layer/cathode.
- the hole injection layer preferably comprises a conductive polymer, particularly preferably complexes of PEDOT : PSS.
- Example 2 The combined organic phases were washed with water, dried over MgS0 4 and filtered and the solvent was stripped off in vacuo.
- the crude product obtained (20.5 g) was purified by chromatography (silica gel 60, eluent: toluene). Yield: 10.3 g (60 % of theory); slightly reddish oil with a product content according to GC-MS analysis of 79.5 %.
- the product was employed in Example 2 without further purification.
- Example 2
- Aluminium chloride (12.66 g, 94.9 mmol) was added in portions to a suspension of l-(6-bromohexano)naphthone (9.06 g, 29.7 mmol) and sodium borohydride (6.47 g, 171 mmol) in anhydrous THF (200 ml) at 0-4 °C. Then, heating under reflux was carried out for 3 hours. After cooling, water (100 ml) was slowly metered in. Ethyl acetate (100 ml) was then added, the organic phase was separated off and the aqueous phase was extracted with ethyl acetate (30 ml). The combined organic phases were dried with sodium sulphate and filtered and the solvent was evaporated.
- N-Bromosuccinimide (2.93 g, 16.5 mmol) was added in one portion to a solution of r-(6-bromohexyl)naphthene (4.37 g, 15 mmol) in acetonitrile (45 ml). The solution was stirred for 16 hours with exclusion of light. The reaction solution was added to water (100 ml) and extracted with 3 x 50 ml of methylene chloride. The combined organic phases were dried over Na 2 S0 4 and filtered and the solvent was evaporated. The crude product obtained (4.08 g, brown oil) was purified by chromatography (silica gel, eluent: hexane).
- 0.326 g of potassium phthalimide was added to a solution of 0.54 g of ⁇ , ⁇ '- diphenyl-N,N'-di-4-(6-bromohexyl)naphthylbenzidine in 15 ml of anhydrous DMF. The solution was stirred at 100 °C for 16 hours. After cooling, the solvent was stripped off in vacuo, water was added to the residue and the residue was filtered off, rinsed with water and dried in vacuo at 40 °C. The intermediate product was suspended in 20 ml of ethylene glycol, 0.165 g of hydrazine hydrate (98 % pure) were added and it was stirred at 175 °C for 18 hours.
- the solution was degassed and a solution, prepared under argon, of 0.03 g (0.1 mmol) of bis(dibenzylideneacetone)palladium(0) and 0.01 g (0.05 mmol) of tri-tert- butylphosphine in 15 ml of anhydrous toluene was then injected at 1 10 °C.
- the reaction solution was boiled under reflux for 19.5 h. After cooling, 250 ml of methylene chloride were added and extracted with 2 x 40 ml of water. The organic phase was dried over Na 2 S0 4 , filtered and concentrated.
- the crude product obtained was purified by chromatography (silica gel, mobile phase: hexane/toluene 1 : 1).
- N,N'-Diphenyl-N-4-(6-bromohexyl)naphthyl-N'-4-naphthylbenzidine is reacted in accordance with Example 7 to give the product.
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WO2009017024A1 (ja) | 2007-07-31 | 2009-02-05 | Sumitomo Chemical Company, Limited | 有機エレクトロルミネッセンス装置の製造方法 |
-
2011
- 2011-07-19 DE DE102011107921A patent/DE102011107921B3/de not_active Expired - Fee Related
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2012
- 2012-07-16 WO PCT/EP2012/002989 patent/WO2013010661A1/en active Application Filing
- 2012-07-18 TW TW101125718A patent/TW201311862A/zh unknown
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DE102011107921B3 (de) | 2012-11-15 |
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