JP5133562B2 - 有機半導体を含む電子デバイス - Google Patents
有機半導体を含む電子デバイス Download PDFInfo
- Publication number
- JP5133562B2 JP5133562B2 JP2006525128A JP2006525128A JP5133562B2 JP 5133562 B2 JP5133562 B2 JP 5133562B2 JP 2006525128 A JP2006525128 A JP 2006525128A JP 2006525128 A JP2006525128 A JP 2006525128A JP 5133562 B2 JP5133562 B2 JP 5133562B2
- Authority
- JP
- Japan
- Prior art keywords
- organic
- polymer
- buffer layer
- atoms
- emitting diode
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004065 semiconductor Substances 0.000 title claims abstract description 57
- 229920000642 polymer Polymers 0.000 claims abstract description 93
- 238000004132 cross linking Methods 0.000 claims abstract description 56
- 239000000463 material Substances 0.000 claims abstract description 44
- 125000002091 cationic group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000000412 dendrimer Substances 0.000 claims description 12
- 229920000736 dendritic polymer Polymers 0.000 claims description 12
- 229920001940 conductive polymer Polymers 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- 239000012298 atmosphere Substances 0.000 claims description 8
- 239000004020 conductor Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920000767 polyaniline Polymers 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229920000123 polythiophene Polymers 0.000 claims description 6
- 125000005259 triarylamine group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229920000547 conjugated polymer Polymers 0.000 claims description 5
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 239000010405 anode material Substances 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 229920006037 cross link polymer Polymers 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 19
- 230000008569 process Effects 0.000 abstract description 9
- 238000007639 printing Methods 0.000 abstract description 7
- 230000005855 radiation Effects 0.000 abstract description 6
- 238000007641 inkjet printing Methods 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 2
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 238000007669 thermal treatment Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 123
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 27
- 239000000178 monomer Substances 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- -1 {4-[(2-hydroxytetradecyl) -oxyl] -phenyl} -phenyl Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 5
- 229910052776 Thorium Inorganic materials 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000012656 cationic ring opening polymerization Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- 239000002346 layers by function Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JEVIWOHJFUIYMO-UHFFFAOYSA-N 11-(4-bromophenoxy)undecan-1-ol Chemical compound OCCCCCCCCCCCOC1=CC=C(Br)C=C1 JEVIWOHJFUIYMO-UHFFFAOYSA-N 0.000 description 2
- OJKMWOSAZMWOMJ-UHFFFAOYSA-N 3-[11-(4-bromophenoxy)undecoxy]-3-ethyl-2-methylideneoxetane Chemical compound BrC1=CC=C(OCCCCCCCCCCCOC2(C(OC2)=C)CC)C=C1 OJKMWOSAZMWOMJ-UHFFFAOYSA-N 0.000 description 2
- XDJIQWRWOJKPCS-UHFFFAOYSA-N 3-ethyl-3-(iodomethyl)oxetane Chemical compound CCC1(CI)COC1 XDJIQWRWOJKPCS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002322 conducting polymer Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000011243 crosslinked material Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- XYJBIADAEAEWNG-UHFFFAOYSA-N 1,2-dipentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1OCCCCC XYJBIADAEAEWNG-UHFFFAOYSA-N 0.000 description 1
- ORQHBYAQYTUUJN-UHFFFAOYSA-N 1,2-dipentoxybenzene hydrobromide Chemical compound Br.CCCCCOC1=CC=CC=C1OCCCCC ORQHBYAQYTUUJN-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- IRTCJFCIQKNFPP-UHFFFAOYSA-N 2-methyl-1,4-dioxane Chemical compound CC1COCCO1 IRTCJFCIQKNFPP-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- UPFRYENSFLJWKO-UHFFFAOYSA-N 4-[4-(4-tert-butylanilino)phenyl]-N-(4-tert-butylphenyl)-3-phenylaniline Chemical compound C1(=CC=CC=C1)C1=C(C=CC(=C1)NC1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)NC1=CC=C(C=C1)C(C)(C)C UPFRYENSFLJWKO-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001167 Poly(triaryl amine) Polymers 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- UWAXDPWQPGZNIO-UHFFFAOYSA-N benzylsilane Chemical compound [SiH3]CC1=CC=CC=C1 UWAXDPWQPGZNIO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910001449 indium ion Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- QBODEGFCUGKATP-UHFFFAOYSA-N n-(4-bromophenyl)-4-[4-(n-(4-bromophenyl)-4-tert-butylanilino)phenyl]-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(Br)=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(Br)C=C1 QBODEGFCUGKATP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000007750 plasma spraying Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/20—Changing the shape of the active layer in the devices, e.g. patterning
- H10K71/211—Changing the shape of the active layer in the devices, e.g. patterning by selective transformation of an existing layer
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
- Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
- Y10T428/264—Up to 3 mils
- Y10T428/265—1 mil or less
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
- Y10T428/269—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension including synthetic resin or polymer layer or component
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Thin Film Transistor (AREA)
- Formation Of Insulating Films (AREA)
- Junction Field-Effect Transistors (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10340711.1 | 2003-09-04 | ||
| DE2003140711 DE10340711A1 (de) | 2003-09-04 | 2003-09-04 | Elektronische Vorrichtung enthaltend organische Halbleiter |
| PCT/EP2004/009902 WO2005024970A1 (de) | 2003-09-04 | 2004-09-04 | Elektronische vorrichtung enthaltend einen organischen halbleiter und dazwischen eine pufferschicht bestehend aus einem polymer welches kationisch polymerisierbar ist und keine photosäure enthält |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007504656A JP2007504656A (ja) | 2007-03-01 |
| JP5133562B2 true JP5133562B2 (ja) | 2013-01-30 |
Family
ID=34258390
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006525129A Expired - Lifetime JP5355857B2 (ja) | 2003-09-04 | 2004-09-04 | 有機導体および半導体と架橋したポリマーからなる中間バッファー層とを備えた電子デバイス |
| JP2006525128A Expired - Lifetime JP5133562B2 (ja) | 2003-09-04 | 2004-09-04 | 有機半導体を含む電子デバイス |
| JP2013098569A Withdrawn JP2013191867A (ja) | 2003-09-04 | 2013-05-08 | 有機導体および半導体と架橋したポリマーからなる中間バッファー層とを備えた電子デバイス |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006525129A Expired - Lifetime JP5355857B2 (ja) | 2003-09-04 | 2004-09-04 | 有機導体および半導体と架橋したポリマーからなる中間バッファー層とを備えた電子デバイス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013098569A Withdrawn JP2013191867A (ja) | 2003-09-04 | 2013-05-08 | 有機導体および半導体と架橋したポリマーからなる中間バッファー層とを備えた電子デバイス |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20070034862A1 (enExample) |
| EP (2) | EP1661191B1 (enExample) |
| JP (3) | JP5355857B2 (enExample) |
| KR (2) | KR101042863B1 (enExample) |
| CN (2) | CN100508237C (enExample) |
| AT (2) | ATE418161T1 (enExample) |
| DE (3) | DE10340711A1 (enExample) |
| WO (2) | WO2005024971A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10340711A1 (de) * | 2003-09-04 | 2005-04-07 | Covion Organic Semiconductors Gmbh | Elektronische Vorrichtung enthaltend organische Halbleiter |
| KR100738219B1 (ko) * | 2003-12-23 | 2007-07-12 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자용 중간층 형성 물질 및 이를 이용한유기 전계 발광 소자 |
| DE102004021567A1 (de) | 2004-05-03 | 2005-12-08 | Covion Organic Semiconductors Gmbh | Elektronische Vorrichtungen enthaltend organische Halbleiter |
| GB2425654B (en) * | 2005-04-29 | 2010-03-17 | Seiko Epson Corp | A method of fabricating a heterojunction of organic semiconducting polymers |
| KR100715548B1 (ko) * | 2005-07-29 | 2007-05-07 | 광 석 서 | 부분 치환된 고분자 도판트를 사용하여 합성된 전도성고분자 |
| US7576356B2 (en) * | 2005-08-08 | 2009-08-18 | Osram Opto Semiconductors Gmbh | Solution processed crosslinkable hole injection and hole transport polymers for OLEDs |
| US8440324B2 (en) | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
| EP2412699A1 (en) * | 2005-12-28 | 2012-02-01 | E.I. Du Pont De Nemours And Company | Compositions comprising novel compounds and electronic devices made with such compositions |
| US8138075B1 (en) | 2006-02-06 | 2012-03-20 | Eberlein Dietmar C | Systems and methods for the manufacture of flat panel devices |
| DE102006006412A1 (de) * | 2006-02-13 | 2007-08-16 | Merck Patent Gmbh | Elektronisches Bauteil, Verfahren zu dessen Herstellung und dessen Verwendung |
| DE112007000699T5 (de) | 2006-05-12 | 2009-06-04 | Merck Patent Gmbh | Auf Indenofluorenpolymeren basierende organische Halbleitermaterialien |
| JP4175397B2 (ja) * | 2006-06-28 | 2008-11-05 | セイコーエプソン株式会社 | 有機エレクトロルミネセンス装置の製造方法 |
| JPWO2008010487A1 (ja) | 2006-07-19 | 2009-12-17 | 日立化成工業株式会社 | 有機エレクトロニクス用材料、有機エレクトロニクス素子および有機エレクトロルミネセンス素子 |
| EP2112702B2 (en) * | 2007-02-15 | 2017-12-13 | Mitsubishi Chemical Corporation | Method for manufacturing an organic electroluminescence device |
| JP5196928B2 (ja) * | 2007-09-18 | 2013-05-15 | キヤノン株式会社 | 有機発光素子及び表示装置 |
| US8586684B2 (en) | 2007-11-21 | 2013-11-19 | Merck Patent Gmbh | Conjugated copolymer |
| US20090236979A1 (en) * | 2008-03-24 | 2009-09-24 | Air Products And Chemicals, Inc. | Organic Electroluminescent Device and the Method of Making |
| JP5540600B2 (ja) * | 2008-08-13 | 2014-07-02 | 三菱化学株式会社 | 電子デバイス、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明 |
| US8643000B2 (en) * | 2008-11-18 | 2014-02-04 | E I Du Pont De Nemours And Company | Organic electronic device with low-reflectance electrode |
| JP5359255B2 (ja) * | 2008-12-19 | 2013-12-04 | コニカミノルタ株式会社 | 有機光電変換素子 |
| JP5141600B2 (ja) * | 2009-03-09 | 2013-02-13 | 三菱化学株式会社 | 有機電界発光素子用組成物の製造方法 |
| JP5696662B2 (ja) | 2009-06-01 | 2015-04-08 | 日立化成株式会社 | 有機エレクトロルミネセンス素子、表示素子、照明装置および表示装置 |
| US8575303B2 (en) * | 2010-01-19 | 2013-11-05 | Sirigen Group Limited | Reagents for directed biomarker signal amplification |
| US8859171B2 (en) * | 2010-03-03 | 2014-10-14 | Xerox Corporation | Charge transport particles |
| KR101181228B1 (ko) * | 2010-10-11 | 2012-09-10 | 포항공과대학교 산학협력단 | 유기 태양 전지 및 이의 제조 방법 |
| KR101756657B1 (ko) * | 2010-11-03 | 2017-07-12 | 엘지디스플레이 주식회사 | 백색 유기 발광 소자 및 이를 이용한 표시 장치 |
| JP5944120B2 (ja) * | 2011-07-21 | 2016-07-05 | コニカミノルタ株式会社 | 有機光電変換素子とその製造方法、およびそれを用いた有機太陽電池 |
| KR20150052024A (ko) * | 2012-09-04 | 2015-05-13 | 미쯔비시 가가꾸 가부시끼가이샤 | 유기 전계 발광 소자 및 그의 제조 방법 |
| US9502657B2 (en) | 2012-09-07 | 2016-11-22 | Pioneer Corporation | Organic electroluminescence device and manufacturing method thereof |
| CN104756274B (zh) | 2012-09-18 | 2017-06-09 | 荷兰应用自然科学研究组织Tno | 电光器件堆叠体 |
| JP6545619B2 (ja) * | 2012-09-27 | 2019-07-17 | メルク パテント ゲーエムベーハー | 有機エレクトロルミッセンス素子のための材料 |
| JP6371304B2 (ja) * | 2012-12-13 | 2018-08-08 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 閉じ込め層およびそれを使って製造されるデバイスを製造するための方法および材料 |
| KR102372211B1 (ko) * | 2014-03-27 | 2022-03-08 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 |
| CN106133938B (zh) * | 2014-04-09 | 2018-06-19 | 住友化学株式会社 | 发光元件和用于该发光元件的组合物 |
| JP6593432B2 (ja) * | 2015-02-25 | 2019-10-23 | 三菱ケミカル株式会社 | 重合体、有機電界発光素子用組成物、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明 |
| CN108701765A (zh) * | 2015-10-16 | 2018-10-23 | 陶氏环球技术有限责任公司 | 用于制备有机电荷传输膜的方法 |
| US9644112B1 (en) * | 2016-04-20 | 2017-05-09 | Eastman Kodak Company | Articles having electrically-conductive layer or pattern |
| KR102472751B1 (ko) | 2016-12-06 | 2022-11-30 | 메르크 파텐트 게엠베하 | 전자 디바이스의 제조 방법 |
| WO2018173801A1 (ja) * | 2017-03-24 | 2018-09-27 | 日産化学株式会社 | フッ素原子含有重合体及びその利用 |
| JP2018203889A (ja) * | 2017-06-06 | 2018-12-27 | 日立化成株式会社 | 硬化性重合体、重合液、導電性膜及び有機発光素子 |
| WO2019009327A1 (ja) | 2017-07-04 | 2019-01-10 | 日立化成株式会社 | 有機エレクトロニクス材料及び有機エレクトロニクス素子 |
| KR102385225B1 (ko) | 2017-07-12 | 2022-04-11 | 삼성디스플레이 주식회사 | 유기막 형성용 조성물, 이를 이용한 표시 장치 및 표시 장치의 제조 방법 |
| CN107799571B (zh) * | 2017-10-12 | 2020-10-09 | 武汉华星光电半导体显示技术有限公司 | 有机发光二极管器件及显示装置 |
| CN112352331A (zh) * | 2018-07-11 | 2021-02-09 | 默克专利有限公司 | 含高度支化聚合物的制剂、高度支化聚合物和含此高度支化聚合物的电光器件 |
| CN111048663B (zh) | 2018-10-12 | 2025-07-08 | 康宁股份有限公司 | 用于有机薄膜晶体管的可uv图案化的聚合物掺混物 |
| CN111138810B (zh) | 2018-11-05 | 2024-05-17 | 康宁股份有限公司 | 用于有机薄膜晶体管的可uv图案化的聚合物掺混物 |
| KR102806396B1 (ko) | 2018-12-05 | 2025-05-14 | 삼성디스플레이 주식회사 | 축합환 화합물, 이를 포함한 조성물 및 이로부터 형성된 박막을 포함하는 유기 발광 소자 |
| KR20220036393A (ko) | 2020-09-14 | 2022-03-23 | 삼성디스플레이 주식회사 | 표시 장치 |
| KR20220060630A (ko) | 2020-11-04 | 2022-05-12 | 삼성디스플레이 주식회사 | 기판의 도전성 본딩 구조 및 이를 포함하는 표시 장치 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4720432A (en) * | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
| US5331183A (en) | 1992-08-17 | 1994-07-19 | The Regents Of The University Of California | Conjugated polymer - acceptor heterojunctions; diodes, photodiodes, and photovoltaic cells |
| JP3082479B2 (ja) * | 1992-10-23 | 2000-08-28 | ジェイエスアール株式会社 | ネガ型感放射線性樹脂組成物 |
| DE4325885A1 (de) * | 1993-08-02 | 1995-02-09 | Basf Ag | Elektrolumineszierende Anordnung |
| JP2848207B2 (ja) * | 1993-09-17 | 1999-01-20 | 凸版印刷株式会社 | 有機薄膜ｅｌ素子 |
| EP0666298A3 (en) * | 1994-02-08 | 1995-11-15 | Tdk Corp | Organic electroluminescent element and compound used therein. |
| EP0676461B1 (de) | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
| DE69531477T2 (de) | 1994-05-16 | 2004-07-15 | Koninklijke Philips Electronics N.V. | Halbleiteranordnung aus halbleitendem, organischem material |
| JP3246189B2 (ja) | 1994-06-28 | 2002-01-15 | 株式会社日立製作所 | 半導体表示装置 |
| TW293172B (enExample) | 1994-12-09 | 1996-12-11 | At & T Corp | |
| DE19500912A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Elektrolumineszierende Anordnung |
| KR100431015B1 (ko) * | 1995-07-28 | 2004-07-30 | 다우 글로벌 테크놀로지스 인크. | 2,7-아릴-9-치환된플루오렌및9-치환된플루오렌올리고머및중합체 |
| WO1997005184A1 (en) * | 1995-07-28 | 1997-02-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
| US5929194A (en) † | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
| JP3643433B2 (ja) | 1996-03-25 | 2005-04-27 | ケミプロ化成株式会社 | トリフェニルアミン含有ポリエーテルケトン、その製法およびそれを用いた有機ｅｌ素子 |
| WO1998003566A1 (en) | 1996-07-19 | 1998-01-29 | The Regents Of The University Of California | Conjugated polymers as materials for solid state lasers |
| JP3899566B2 (ja) | 1996-11-25 | 2007-03-28 | セイコーエプソン株式会社 | 有機ｅｌ表示装置の製造方法 |
| DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
| DE19711713A1 (de) | 1997-03-20 | 1998-10-01 | Hoechst Ag | Photovoltaische Zelle |
| US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| WO1999010939A2 (en) | 1997-08-22 | 1999-03-04 | Koninklijke Philips Electronics N.V. | A method of manufacturing a field-effect transistor substantially consisting of organic materials |
| JP2000077185A (ja) * | 1998-08-28 | 2000-03-14 | Asahi Chem Ind Co Ltd | 有機エレクトロルミネッセンス素子 |
| US6107452A (en) * | 1998-10-09 | 2000-08-22 | International Business Machines Corporation | Thermally and/or photochemically crosslinked electroactive polymers in the manufacture of opto-electronic devices |
| KR100400291B1 (ko) * | 1998-11-27 | 2004-02-05 | 주식회사 하이닉스반도체 | 신규의포토레지스트용단량체,그의공중합체및이를이용한포토레지스트조성물 |
| KR100766288B1 (ko) | 1999-01-15 | 2007-10-11 | 스미또모 가가꾸 가부시키가이샤 | 반도체성 중합체 전계 효과 트랜지스터 |
| JP2001076874A (ja) * | 1999-09-07 | 2001-03-23 | Tdk Corp | 有機ｅｌ表示装置 |
| KR20020095210A (ko) * | 2000-04-11 | 2002-12-20 | 듀폰 디스플레이즈, 인크. | 가용성 폴리(플루오렌-옥사디아졸) 공액 중합체 |
| DE10037391A1 (de) * | 2000-08-01 | 2002-02-14 | Covion Organic Semiconductors | Strukturierbare Materialien, Verfahren zu deren Herstellung und deren Verwendung |
| DE10044840A1 (de) * | 2000-09-11 | 2002-04-04 | Siemens Ag | Photostrukturierbare neue organische Halbleitermaterialien |
| EP1370619B1 (de) | 2001-03-10 | 2006-06-21 | MERCK PATENT GmbH | Lösung und dispersionen organischer halbleiter |
| JP2003007471A (ja) * | 2001-04-13 | 2003-01-10 | Semiconductor Energy Lab Co Ltd | 有機発光素子および前記素子を用いた発光装置 |
| EP1390962B2 (en) * | 2001-05-16 | 2023-07-05 | The Trustees Of Princeton University | High efficiency multi-color electro-phosphorescent oleds |
| JP2003007475A (ja) * | 2001-06-20 | 2003-01-10 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
| JP2003029400A (ja) * | 2001-07-19 | 2003-01-29 | Fuji Photo Film Co Ltd | 画像形成材料 |
| DE10143353A1 (de) | 2001-09-04 | 2003-03-20 | Covion Organic Semiconductors | Konjugierte Polymere enthaltend Spirobifluoren-Einheiten und deren Verwendung |
| JP2003103696A (ja) * | 2001-09-27 | 2003-04-09 | Hitachi Chem Co Ltd | 凹凸を形成するための版、その製造方法、それを用いた電磁波シールド材料、その製造方法、並びにその電磁波シールド材料を用いた電磁波遮蔽構成体及び電磁波シールドディスプレイ |
| EP1308781A3 (en) | 2001-10-05 | 2003-09-03 | Shipley Co. L.L.C. | Cyclic sulfonium and sulfoxonium photoacid generators and photoresists containing them |
| JP2003142272A (ja) * | 2001-11-01 | 2003-05-16 | Nichia Chem Ind Ltd | 高分子正孔輸送材およびそれを用いた有機電界発光素子 |
| JP4197117B2 (ja) † | 2001-11-22 | 2008-12-17 | シャープ株式会社 | キャリア輸送性を有する高分子材料を用いた有機薄膜素子、有機薄膜素子の製造方法、および配線 |
| JP2003163086A (ja) * | 2001-11-27 | 2003-06-06 | Nippon Hoso Kyokai <Nhk> | 有機ｅｌ素子および有機ｅｌディスプレイ |
| US6743757B2 (en) * | 2001-12-06 | 2004-06-01 | Infineum International Ltd. | Dispersants and lubricating oil compositions containing same |
| DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
| TW536924B (en) | 2002-02-22 | 2003-06-11 | E Ray Optoelectronics Technolo | Efficient organic electroluminescent device with new red fluorescent dopants |
| JP3946671B2 (ja) | 2002-07-23 | 2007-07-18 | 三星エスディアイ株式会社 | 光子発光抑制素子基盤の画像表示装置及びこれを利用した画像表示方法 |
| US20040028804A1 (en) * | 2002-08-07 | 2004-02-12 | Anderson Daniel G. | Production of polymeric microarrays |
| US7531377B2 (en) † | 2002-09-03 | 2009-05-12 | Cambridge Display Technology Limited | Optical device |
| DE10249723A1 (de) | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
| GB0226010D0 (en) * | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
| US6982179B2 (en) * | 2002-11-15 | 2006-01-03 | University Display Corporation | Structure and method of fabricating organic devices |
| JP4500304B2 (ja) * | 2003-05-12 | 2010-07-14 | ケンブリッジ エンタープライズ リミティド | ポリマーデバイスの製造 |
| US20050017629A1 (en) * | 2003-07-22 | 2005-01-27 | Altair Center, Llc. | Light emitting devices based on hyperbranched polymers with lanthanide ions |
| DE10340711A1 (de) * | 2003-09-04 | 2005-04-07 | Covion Organic Semiconductors Gmbh | Elektronische Vorrichtung enthaltend organische Halbleiter |
-
2003
- 2003-09-04 DE DE2003140711 patent/DE10340711A1/de not_active Withdrawn
-
2004
- 2004-09-04 DE DE200450012028 patent/DE502004012028D1/de not_active Expired - Lifetime
- 2004-09-04 US US10/570,640 patent/US20070034862A1/en not_active Abandoned
- 2004-09-04 AT AT04764854T patent/ATE418161T1/de not_active IP Right Cessation
- 2004-09-04 CN CNB2004800289980A patent/CN100508237C/zh not_active Expired - Fee Related
- 2004-09-04 CN CNA2004800253688A patent/CN1849717A/zh active Pending
- 2004-09-04 US US10/570,372 patent/US7901766B2/en not_active Expired - Fee Related
- 2004-09-04 WO PCT/EP2004/009903 patent/WO2005024971A1/de not_active Ceased
- 2004-09-04 AT AT04764853T patent/ATE492913T1/de active
- 2004-09-04 KR KR1020067004566A patent/KR101042863B1/ko not_active Expired - Lifetime
- 2004-09-04 JP JP2006525129A patent/JP5355857B2/ja not_active Expired - Lifetime
- 2004-09-04 DE DE200450008698 patent/DE502004008698D1/de not_active Expired - Lifetime
- 2004-09-04 EP EP20040764854 patent/EP1661191B1/de not_active Expired - Lifetime
- 2004-09-04 EP EP04764853.0A patent/EP1671379B2/de not_active Expired - Lifetime
- 2004-09-04 WO PCT/EP2004/009902 patent/WO2005024970A1/de not_active Ceased
- 2004-09-04 JP JP2006525128A patent/JP5133562B2/ja not_active Expired - Lifetime
-
2006
- 2006-03-03 KR KR1020067004561A patent/KR101071034B1/ko not_active Expired - Lifetime
-
2013
- 2013-05-08 JP JP2013098569A patent/JP2013191867A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN100508237C (zh) | 2009-07-01 |
| KR101042863B1 (ko) | 2011-06-20 |
| US20060251886A1 (en) | 2006-11-09 |
| CN1849717A (zh) | 2006-10-18 |
| JP2013191867A (ja) | 2013-09-26 |
| JP2007504656A (ja) | 2007-03-01 |
| JP5355857B2 (ja) | 2013-11-27 |
| WO2005024970A1 (de) | 2005-03-17 |
| CN1864280A (zh) | 2006-11-15 |
| EP1671379B8 (de) | 2011-03-23 |
| EP1661191B1 (de) | 2008-12-17 |
| EP1661191A1 (de) | 2006-05-31 |
| DE502004012028D1 (de) | 2011-02-03 |
| KR20060096414A (ko) | 2006-09-11 |
| KR20070036014A (ko) | 2007-04-02 |
| EP1671379B1 (de) | 2010-12-22 |
| DE502004008698D1 (de) | 2009-01-29 |
| WO2005024971A1 (de) | 2005-03-17 |
| ATE418161T1 (de) | 2009-01-15 |
| US7901766B2 (en) | 2011-03-08 |
| ATE492913T1 (de) | 2011-01-15 |
| EP1671379B2 (de) | 2014-10-01 |
| JP2007504657A (ja) | 2007-03-01 |
| DE10340711A1 (de) | 2005-04-07 |
| EP1671379A1 (de) | 2006-06-21 |
| US20070034862A1 (en) | 2007-02-15 |
| KR101071034B1 (ko) | 2011-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5133562B2 (ja) | 有機半導体を含む電子デバイス | |
| JP5096378B2 (ja) | 有機電子素子、その製造方法及びその使用 | |
| Yang et al. | Deep-red electroluminescent polymers: synthesis and characterization of new low-band-gap conjugated copolymers for light-emitting diodes and photovoltaic devices | |
| US20070290194A1 (en) | Method for Cross-Linking an Organic Semi-Conductor | |
| WO2005034199A2 (en) | Organic diodes and materials | |
| JP2010528119A (ja) | 共役ポリマーのための溶媒システム | |
| CN1404521A (zh) | 发光聚合物 | |
| JP2013179181A (ja) | 有機光電変換素子 | |
| EP2001925A2 (en) | Electronic devices containing acene-thiophene copolymers | |
| EP3489240A1 (en) | In-situ cross-linkable hole transporting triazatruxene monomers for optoelectronic devicestr | |
| JP2004002741A (ja) | 高分子化合物、１，４−フェニレンジアミン誘導体、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 | |
| JP5778030B2 (ja) | 光電子的応用のためのフッ素で橋かけされた会合体 | |
| Bolink et al. | Optimization of Polymer Blue‐Light‐Emitting Devices by Introducing a Hole‐Injection Layer Doped with the Molecular Nanomagnet [Mn12O12 (H2O) 4 (C6F5COO) 16] | |
| KR101637058B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 태양전지 | |
| Liu et al. | Synthesis and characterization of novel polymers containing aminophenylsilole | |
| KR102850797B1 (ko) | 가교결합성 벤조시클로부텐기를 갖는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
| KR102310582B1 (ko) | 유기 반도체 화합물 및 이를 포함하는 유기 전자 소자 | |
| KR20250074303A (ko) | 정공 수송용 재료 및 이를 이용한 유기 전기 소자 및 그 전자기기 | |
| JP2010251235A (ja) | 電子素子 | |
| Dumur et al. | Photoinitiated Cross‐Linking in OLEDs: An Efficient Tool for Addressing the Solution‐Processed Devices Elaboration and Stability Issues | |
| KR20100132788A (ko) | 유기 태양 전지 및 그 제조방법 | |
| WO2012121233A1 (ja) | 化合物及び該化合物を用いてなる薄膜 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070903 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100316 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100614 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110222 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110617 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20110622 |
|
| A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20110930 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120905 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121108 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151116 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5133562 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |