JP4582093B2 - El素子 - Google Patents
El素子 Download PDFInfo
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- JP4582093B2 JP4582093B2 JP2006526700A JP2006526700A JP4582093B2 JP 4582093 B2 JP4582093 B2 JP 4582093B2 JP 2006526700 A JP2006526700 A JP 2006526700A JP 2006526700 A JP2006526700 A JP 2006526700A JP 4582093 B2 JP4582093 B2 JP 4582093B2
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- 239000010410 layer Substances 0.000 claims description 72
- 239000000463 material Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 24
- 239000002019 doping agent Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 150000003573 thiols Chemical class 0.000 claims description 11
- 125000006850 spacer group Chemical group 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 8
- 239000002800 charge carrier Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 239000002195 soluble material Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 229920000642 polymer Polymers 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- -1 poly (p-phenylene vinylene) Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- FYLKHVAQFJBJOW-UHFFFAOYSA-N 9-[4-[4-(3-formylcarbazol-9-yl)phenyl]phenyl]carbazole-3-carbaldehyde Chemical group C12=CC=CC=C2C2=CC(C=O)=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=C(C=O)C=C3C3=CC=CC=C32)C=C1 FYLKHVAQFJBJOW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- JQGGYGKXKWTXTF-UHFFFAOYSA-N 1-ethenoxy-3-prop-2-enoxy-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COC=C JQGGYGKXKWTXTF-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910016455 AlBN Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- JKVHJZAMJFGVIY-UHFFFAOYSA-N [9-[4-[4-[3-(hydroxymethyl)carbazol-9-yl]phenyl]phenyl]carbazol-3-yl]methanol Chemical group C12=CC=CC=C2C2=CC(CO)=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=C(CO)C=C3C3=CC=CC=C32)C=C1 JKVHJZAMJFGVIY-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 125000002009 alkene group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical group [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- IAPHXJRHXBQDQJ-WKMWQDDRSA-N jacobine Chemical compound C[C@@H]1O[C@]11C(=O)O[C@@H]([C@@H]23)CCN3CC=C2COC(=O)[C@](C)(O)[C@H](C)C1 IAPHXJRHXBQDQJ-WKMWQDDRSA-N 0.000 description 2
- IAPHXJRHXBQDQJ-ODLOZXJASA-N jacobine Natural products O=C1[C@@]2([C@H](C)O2)C[C@H](C)[C@](O)(C)C(=O)OCC=2[C@H]3N(CC=2)CC[C@H]3O1 IAPHXJRHXBQDQJ-ODLOZXJASA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 1
- SGPZQRDTKWINJJ-UHFFFAOYSA-N 2,3,4-triphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SGPZQRDTKWINJJ-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- IXPCJOPIVIEBBA-UHFFFAOYSA-N [Pt+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Pt+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 IXPCJOPIVIEBBA-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- UCOHKZKRNWNULS-UHFFFAOYSA-N aminocyanamide Chemical compound NNC#N UCOHKZKRNWNULS-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical class O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid 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
- 125000001188 haloalkyl group Chemical group 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
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- MUJNAWXXOJRNGK-UHFFFAOYSA-N n-[3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propyl]cyclohexanamine Chemical compound C1=2CCCCC=2C2=CC(C)=CC=C2N1CCCNC1CCCCC1 MUJNAWXXOJRNGK-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Chemical group 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing 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
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 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 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- 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
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- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Description
架橋は、湿式法によりデバイス層を積層するために使用される。例えば、US6107452は、末端ビニル基を含むフルオレン含有オリゴマーを溶液から塗布し、その上に追加の層を塗布できるよう不溶性ポリマーを形成するため架橋される。同様に、KimらによるSynthetic Metals 122 (2001), 363-368は、ポリマーの塗布後に架橋できるトリアリールアミン基及びエチニル基について記載している。
ホスト材料、及び下記式(I)の発光ドーパントモノマーを含む組成物を基板上に塗布することにより表面を有するEL層を形成すること、
式(I)のモノマーを重合することにより、EL層の少なくともある部分を溶媒に不溶にすること、
EL層を溶媒にさらすこと、及び
EL層上に第2の型の電荷キャリアを注入し得る第2の電極を成膜すること
を含むELデバイスを形成する方法を提供する。
(式中、Xは重合可能な基を示し、Aは発光基を示し、Cは結合又はスペーサー基を示し、nは整数である。)
好ましくは、この組成物は、Xとの共重合のための第2の重合可能な基Yを含む。
チオール−エン混合物は、容易に熱重合及び光重合され得る。光重合は、良好な解像度でパターニングされた膜が得られるという利点を有し、そのため光重合は、OLED用には好ましい。反応性不飽和炭素−炭素結合は、好ましくは電子リッチであり、又は歪んだリング系を形成する。後者の場合、反応性不飽和炭素−炭素結合とチオールとの反応は、リングの歪みを開放する。反応性不飽和基は、好ましくはノルボルニル又はビニルエーテル部分からなり、他の有用なアリルエーテルからなるエン、又は不飽和環状系からなる。チオール−エン系の場合、UV光又は可視光のいずれかによる活性化のための適切な開始剤がある。良好な重合開始のためには、開始剤により吸収されるが、膜の他の成分によっては強く吸収されない波長の光を用いることが好ましい。このようにして、開始剤は良好に機能し、膜の光劣化は最小にされる。
式中、Mは金属、L1、L2及びL3のそれぞれは配位基、qは整数、r及びsはそれぞれ独立に0又は整数、(a.q)+(b.r)+(c.s)は、Mに配位する配位部位の数を示し、aはL1への配位部位の数、bはL2への配位部位の数、cはL3への配位部位の数である。
4,4’−ビス(3−(アリルオキシメチル)カルバゾール−9−イル)(1)
式(I)の化合物は、図2に示す式に従って合成された。
トルエン(88ml)中にtert-ブチルホスフィン(III)(880mg、4.35mmol)を含む溶液を、トルエン(50ml)中にカルバゾール(11.9g、71.0mmol)、4,4’−ジブロモビフェニル(10.0g、32.11mmol)、tert-ブトキシドナトリウム(23.2g、241mmol)及び酢酸パラジウム(324mg、32.1.34mmol)を加え脱酸素化した混合物に、窒素下で添加し、得られた混合物を窒素雰囲気で10日間加熱還流した。反応混合物を室温に冷却し、更にトルエン(200ml)で希釈した。反応混合物を濾過してナトリウム塩を除去し、濾液からすべての微量の生成物を除去した。濾液を乾燥して濃縮し、粗生成物を薄い褐色の固形物として得た。この粗生成物は、最初に、溶出液としてジクロロメタンを用いてシリカゲルクロマトグラフィーにより精製し、次いでトルエンから再結晶した。次いで、この物質を10−6mmHgで280−281℃で昇華させ、生成物4,4’−ビス(カルバゾール−9−イル)ビフェニルを、融点280−281℃(lit.融点281℃)を有する灰色がかった白色の固形物として得た。
オキシ塩化リン(13ml,21.5g,140mmol)を、N,N−ジメチルホルムアミド(5.40ml,5.10g,69.7mmol)及び4,4’−ビス(カルバゾール−9−イル)ビフェニル(7.72ml,16.0mmol)の攪拌混合物に滴下し、得られた混合物を室温で5分間攪拌し、24時間で90℃に加熱した(nb反応混合物は、溶出液として5%エタノール/ジクロロメタンを用いてTLCに供された。)。反応混合物を水(800ml)に注ぎ、このビーカーを超音波浴に2時間置き、物質を加水分解した。この混合物を更に2時間攪拌し、濾過した。残渣を水で、次いでヘキサンで洗浄し、真空中で2時間乾燥した。粗生成物をアセトン(3×400ml)とともに加熱し、濾過した。この生成物は、多くの有機溶媒に不溶であった。アセトンで洗浄することにより不純物を除去した。融点295℃(dec.)を有する生成物である4,4’−ビス(3−ホルミルカルバゾール−9−イル)ビフェニル(7.92g,87%)が得られた。実測値:C,81.74;H,4.71;N,4.45.C38H28N2O2.(CH3)2COの計算値:C,82.25;H,5.05;N,4.68%.1H n.m.r.(300MHz,Me2SO):δ10.09(2H,s,CHO);8.88(2H,d,J0.88Hz,芳香族H);8.41(2H,d,J7.61Hz,芳香族H);8.41(4H,d,J8.49Hz,芳香族H);8.00(2H,dd,J8.49,1.46Hz,芳香族H);7.83(4H,d,J8.49Hz,芳香族H);7.38−7.61(8H,m,芳香族H).λmax(CH2Cl2):215nm(ε/Lmol−1cm−19163),241(68 488),272(65 928),294(67 194),328(42 620).FT−IR(固体):3045,2825,2730,1682,1623,1591,1505,1456,1438,1365,1319,1275,1230,1180,802,745cm−1.
iii)4,4’−ビス(3−(ヒドロキシメチル)カルバゾール−9−イル)ビフェニル(1c)の合成
水素化ホウ素ナトリウム(2.40g,63.4mmol)を、THF(1.2L)中に4,4’−ビス (3−ホルミルカルバゾール−9−イル)ビフェニル(3.42g,6.33mmol)を含む溶液に加え、得られた混合物を室温で24時間攪拌した。反応後、溶出液として5%エタノール/ジクロロメタンを用いてTLCに供された。反応が完了すると、混合物を水(400ml)にゆっくり注ぎ、混合物を室温で更に30分間攪拌するままとした。反応混合物を塩酸(5M)によりpH1に酸性化した。生成物をジクロロメタン(3×300ml)で抽出した。合わせた有機相を水(400ml)及び塩水(400ml)で洗浄し、乾燥し(MgSO4)、濾過し、濾液を蒸発乾固した。粗生成物を溶出液として50%THF/トルエンを用いてシリカゲルクロマトグラフィーにより精製した。生成物をエタノールから再結晶し、生成物4,4’−ビス(3−(ヒドロキシメチル)カルバゾール−9−イル)ビフェニルを、融点268℃(dec)を有する淡い黄色の固形物(3.22g,94%)として得た。実測値:C,82.51;H,4.64;N,4.86.C38H28N2O2.EtOHの計算値:C,81.33;H,5.80;N,4.74%.1H n.m.r.(300MHz,Me2SO):δ8.23(2H,d,J7.61Hz,芳香族H);8.18(2H,s,芳香族H);8.06(4H,d,J8.19Hz,芳香族H);7.75(4H,J8.19Hz,芳香族H);7.38−7.50(8H,m,芳香族H);7.29(2H,m,芳香族H);5.25(2H,t,J5.58Hz,OH);4.68(4H,d,J5.56Hz,CH2).λmax(CH2Cl2):216nm(ε/Lmol−1cm−1177 455),240(57 873),271(56 558),294(55 330),329(37 758).FT−IR(固体):3343,1604,1500,1485,1455,1362,1330,1230,803,745cm−1.
iv)4,4’−ビス(3−(アリルオキシメチル)カルバゾール−9−イル)ビフェニル(1)の合成
DMSOを水素化カルシウム上で乾燥し、次いで真空下で蒸留し、モレキュラーシーブズ上で貯蔵した。DMSO(20ml)に水酸化カリウム(2.07g,36.9mmol)を加え、窒素下、室温で15分間攪拌した。次いで、ジオール(2.39g,4.39mmol)のDMSO溶液(20ml)を加え、更に臭化アリル(2ml,2.80g,21.7mmol)を加え、得られた混合物を窒素下、室温で一昼夜攪拌した。反応混合物を水(200ml)に注ぎ、生成物をジクロロメタン(3×50ml)で抽出した。有機相を合体し、水(5×150ml)、塩水(200ml)で洗浄し、硫酸マグネシウム上で乾燥した。混合物を濾過し、濾液を蒸発乾固した。この物質を溶出液としてジクロロメタンを用いてシリカゲルクロマトグラフィーにより精製した。問題の留分を合体し、減圧下で溶媒を除去した。生成物をジクロロメタン及びヘキサンから回収し、融点118−120℃を有する淡い黄色の固形物として生成物を得た。(実測値:C,82.51;H,4.64;N,4.86.C38H28N2O2.EtOHの計算値:C,81.33;H,5.80;N,4.74%.1H n.m.r.(300MHz,Me2SO):δ8.13−8.20(4H,m,芳香族H);7.87−7.93(4H,m,芳香族H);7.65−7.72(4H,m,芳香族H);7.40−7.65(8H,芳香族H);7.27−7.35(2H,m,芳香族H);5.93−6.09(2H,m,CH=CH);5.30−5.39(2H,m,CH=CH);5.20−5.29(2H,m,CH=CH);4.74(4H,s,CH2);(8H,m,CH2−CH=CH2).λmax(CH2Cl2):241nm(ε/Lmol−1cm−188 506),296(40 331),319(29657).FT−IR(固体):3047,2852,1604,1500,1455,1359,1331,1230,1074,915,807cm−1.
テトライソプロピルペンタエリスリトール(2)の合成
式(2)の化合物を、Nouguier R, Mchich M, J. Chem. 1985, 50, (3296-3298)に開示されているテトラアリルペンタエリスリトールから出発した2段階合成で製造した。
攪拌器を備えた10mlの丸底フラスコに、2.0g(6.74mmol)のテトラアリルペンタエリスリトールを加えた。この試薬を、4.11g(53.98mmol)の新しい蒸留されたチオ酢酸を1mlの部分に加えたアイス浴で冷却した。添加が完了した後、5mgのAlBNを加え、反応混合物を15分間攪拌した。AlBNが溶解した後、反応混合物を60℃で12時間加熱し、この反応後、T.L.C.に供した。反応生成物は、シリカゲル上ジクロロメタン(DCM)で0.05のRf、エタノールで0.9のRfを有していた。真空下で反応混合物から過剰のチオ酢酸を除去し、残渣を最小限のDCM中を使って短いシリカゲルカラム上にのせた。このカラムを500mlのDCMで、次いで500mlのエタノールで溶出した。エタノール部分を回収し、溶媒を除去した。2.9g(71.5%収率)のテトラチオアセチルプロピルペンタエリスリトールを、淡い黄色の固体として単離した。
ii) テトラチオプロピルペンタエリスリトール(2)の合成
100mlの丸底フラスコ内の10mlの無水THFに、1.8g(2.99mmol)のテトラチオアセチルプロピルペンタエリスリトールを加え、混合物を攪拌しつつ脱ガスした。反応容器内を窒素でパージし、THF中に12.3mlの1MのLiAlH4を含む溶液を滴下した。反応物を室温で18時間攪拌し、反応をT.L.C.(ジクロロメタン)によりモニターした。反応が完了したとき、混合物を0.1MのHClでpH3に酸性化し、50mlのDCMを加えた。有機相を回収し、水相を2×50mlのDCMで抽出した。有機層を合体し、100mlの塩水で4回、及び50mlの水で2回抽出した。硫酸ナトリウム上で有機相を乾燥し、濾過し、溶媒を除去した。生成物を、0.92g(71.2%収率)の淡い黄色のオイルとして単離した。生成物をKugelrohr装置で蒸留し、10−4ミルバールで230℃の沸点を有する、流動性のある無色のオイルを得た。
WO 02/060910に開示されているように、Fac−トリス[2−(2−ピリジニル−κN)フェニル−κC]−イリジウム(III)(3)を合成した。
トルエン(90cm3)中に(4)(0.582g,0.717mmol)を含むサスペンジョンを、(5)(0.294g,1.79mmol)のエタノール溶液(40cm3)、炭酸ナトリウム(0.9cm3,1.79mmol)の水溶液、及び水(30cm3)で処理した。混合物を窒素ガスで75分間バブリングした。窒素気流下で、混合物に固体テトラキス(トリフェニルホスフィン)パラジウム(0.040g,0.036mmol)を加えた。次いで、混合物を窒素下で加熱還流した。還流に到達すると、サスペンジョンは透明となり、黄色のサスペンジョンからオレンジ色の混合物に変わった。混合物を窒素下、14.5時間還流を続け、次いで室温に冷却した。反応混合物を室温に冷却すると、両相は透明となった。混合物をジクロロメタン(100cm3)で処理し、有機相を分離した。水相をジクロロメタン(2×50cm3)で洗浄した。合体した有機抽出物を、水(40cm3)で洗浄した。合体した有機抽出物を、次いで、硫酸マグネシウムにより乾燥し、濾過し、真空中で濃縮した。粗生成物を、1:1ジクロロメタン/ヘキサン溶出液でシリカゲルクロマトグラフィーにより精製した。生成物を黄色粉末(0.560g,90%)として単離した。1H nmr(300MHz,CDCL3):8.1−7.4(16H,m),7.4−7.3(4H,m),7.2−7.1(2H,m),7.0−6.7(10H,m),5.79(2H,d,J=18Hz),5.30(CH2Cl2),5.25(2H,d,J=11Hz).ES−MS:860.20(MH+).元素分析:実測値:C:63.55,H:4.17,N:4.97%,IrC49H36N3O2・CH2Cl2の計算値:C:63.62,H:4.06,N:4.45%.
C)りん光発光体をドープした光重合可能なOLEDの製造
ホスト材料1(8mg)、リン光ドーパント3(8wt%)及びチオール2(1.8mg)を、1.5mlの純クロロホルム(トータル濃度5−7mgml−1)中に溶解した。ITOを被覆したガラス基板(市販の洗浄剤中で超音波処理することにより、かつ脱イオン水により洗浄することにより、あらかじめ清浄化され、Emitech K1050Xプラズマユニットでプラズマ処理された(プロセスガス酸素,100W,2分))にその溶液をスピンコートすることにより、発光層を形成した。2000rpm、加速500rs−1で回転する基板上に、トータル30s、溶液をスピンコートし、厚さ約50nmの発光層を得た。次いで、Hanovir UVA 250W UV源を用いて、不活性雰囲気(N2)の下で、膜を光重合した。15nm×20nmの矩形照射領域を与える5”×5”のガラスホトマスク(カットオフ360nm)を通して6−8分間、膜に照射した。トルエンで洗浄し、乾燥窒素流の下で乾燥し、蒸着装置(Kurt J Lesker)に移送し、50nmの厚さの電子輸送/正孔ブロッキング層としてTPBI(以下に示す)及びLiF(1.2nm)とアルミニウム(100−150nm)の二層の上部電極(カソード)を蒸着することにより、OLEDを完成した。アノードとカソードの重なり部が、4mm×5mmの6画素からなる発光領域となる。
Claims (6)
- 第1の型の電荷キャリアを注入するための第1の電極を含む基板を提供すること、
ホスト材料、及び下記式(I)の発光ドーパントモノマーを含む組成物を基板上に成膜することにより、表面を有するEL層を形成すること、
前記EL層の表面の少なくともある部分に光を照射して、下記式(I)のモノマーを重合することにより、EL層の少なくともある部分を溶媒に不溶にすること、
EL層を溶媒にさらすこと、及び
EL層上に第2の型の電荷キャリアを注入し得る第2の電極を成膜すること
を含み、
前記組成物は、下記式(I)に示すXとの共重合のための第2の重合可能な基Yを含み、X及びYの一方は、任意に置換されたチオールであり、他方は、反応性不飽和炭素−炭素結合を含む基であり、前記ホスト材料は、更に別の第1の重合可能な基X又は第2の重合可能な基Yに結合されている、ELデバイスを形成する方法。
A-C-(X)n (I)
(式中、Xは重合可能な基を示し、Aは発光基を示し、Cは結合又はスペーサー基を示し、nは少なくとも2の整数である。ただし、スペーサー基はカルボニル基を含まない。) - 前記発光基は、りん光性化合物である請求項1に記載の方法。
- 前記EL層を溶媒にさらすことにより、洗浄されてパターン化された不溶性EL層を残す溶解性物質を生ずるように、前記EL層の表面のある部分のみにUV光を照射することを式(I)のモノマーを重合する工程が含む請求項1又は2に記載の方法。
- 前記EL層の全面は、不溶性にされている請求項1又は2に記載の方法。
- EL層を溶媒にさらすことは、EL層上に溶媒及び電気的機能物質を含む組成物を成膜することにより、電気的機能層を形成することを含む請求項3に記載の方法。
- 請求項1〜5のいずれかに記載の方法により得られたELデバイス。
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US7700148B2 (en) | 2010-04-20 |
JP2007506237A (ja) | 2007-03-15 |
WO2005027583A1 (en) | 2005-03-24 |
CN1853448A (zh) | 2006-10-25 |
KR101116047B1 (ko) | 2012-03-14 |
US20060216411A1 (en) | 2006-09-28 |
KR20060085243A (ko) | 2006-07-26 |
EP1665895A1 (en) | 2006-06-07 |
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