US20040004433A1 - Buffer layers for organic electroluminescent devices and methods of manufacture and use - Google Patents
Buffer layers for organic electroluminescent devices and methods of manufacture and use Download PDFInfo
- Publication number
- US20040004433A1 US20040004433A1 US10/183,717 US18371702A US2004004433A1 US 20040004433 A1 US20040004433 A1 US 20040004433A1 US 18371702 A US18371702 A US 18371702A US 2004004433 A1 US2004004433 A1 US 2004004433A1
- Authority
- US
- United States
- Prior art keywords
- buffer layer
- electroluminescent device
- layer
- hole transport
- triarylamine
- 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.)
- Abandoned
Links
- 239000000872 buffer Substances 0.000 title claims abstract description 137
- 238000000034 method Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000463 material Substances 0.000 claims abstract description 179
- 125000005259 triarylamine group Chemical group 0.000 claims abstract description 71
- 230000005525 hole transport Effects 0.000 claims abstract description 41
- 239000011230 binding agent Substances 0.000 claims abstract description 25
- 239000002245 particle Substances 0.000 claims abstract description 14
- 238000004891 communication Methods 0.000 claims abstract description 12
- 238000000149 argon plasma sintering Methods 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims description 72
- 238000012546 transfer Methods 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 40
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 239000011147 inorganic material Substances 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 279
- -1 for example Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 26
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 25
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 239000000178 monomer Substances 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000975 dye Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000004793 Polystyrene Substances 0.000 description 14
- 125000000732 arylene group Chemical group 0.000 description 14
- 238000010276 construction Methods 0.000 description 14
- 239000011229 interlayer Substances 0.000 description 14
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 229920002223 polystyrene Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000370 acceptor Substances 0.000 description 12
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 12
- 230000005855 radiation Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 150000003384 small molecules Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 229910003827 NRaRb Inorganic materials 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229910052705 radium Inorganic materials 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 229910052701 rubidium Inorganic materials 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)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 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- BGGDZDRRHQTSPV-UHFFFAOYSA-N 4-ethenyl-n,n-diphenylaniline Chemical compound C1=CC(C=C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BGGDZDRRHQTSPV-UHFFFAOYSA-N 0.000 description 4
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- 229920001400 block copolymer Polymers 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 3
- BMKVLWGCSCKZTD-UHFFFAOYSA-N 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC(=CC=2)B2OC(C)(C)C(C)(C)O2)C3=C1 BMKVLWGCSCKZTD-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 229920001746 electroactive polymer Polymers 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 239000002491 polymer binding agent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- NPJJGMRERPXCSE-UHFFFAOYSA-N 1,4-bis(2-ethyl-6-methylanilino)anthracene-9,10-dione Chemical compound CCC1=CC=CC(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=CC=C1CC NPJJGMRERPXCSE-UHFFFAOYSA-N 0.000 description 2
- ABFHEPUDNWQFIF-UHFFFAOYSA-N 1-n,4-n-bis(4-bromophenyl)-1-n,4-n-bis(4-butylphenyl)benzene-1,4-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(Br)=CC=1)C=1C=CC(CCCC)=CC=1)C1=CC=C(Br)C=C1 ABFHEPUDNWQFIF-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920005731 JONCRYL® 67 Polymers 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZOQXMEDOTSCWAG-UHFFFAOYSA-N n-phenyl-n-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C=CC1=CC=CC=C1 ZOQXMEDOTSCWAG-UHFFFAOYSA-N 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- MLIWQXBKMZNZNF-PWDIZTEBSA-N (2e,6e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)C\C1=C/C1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-PWDIZTEBSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- KETXQNLMOUVTQB-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethylporphyrin;platinum Chemical compound [Pt].C=1C(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC2=NC=1C(CC)=C2CC KETXQNLMOUVTQB-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-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
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JBWRZTKHMKVFMQ-UHFFFAOYSA-N 3,6-dibromo-9-phenylcarbazole Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 JBWRZTKHMKVFMQ-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- XVMUGTFNHXHZIP-UHFFFAOYSA-N 4-[3,5-bis[4-(n-phenylanilino)phenyl]phenyl]-n,n-diphenylaniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=C(C=C(C=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)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 XVMUGTFNHXHZIP-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- UOZOCOQLYQNHII-UHFFFAOYSA-N 6-bromo-2-(6-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2cc(Br)ccc12)C1=[NH+]c2cc(Br)ccc2C1=O UOZOCOQLYQNHII-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- NPNMHHNXCILFEF-UHFFFAOYSA-N [F].[Sn]=O Chemical compound [F].[Sn]=O NPNMHHNXCILFEF-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- XEPMXWGXLQIFJN-UHFFFAOYSA-K aluminum;2-carboxyquinolin-8-olate Chemical compound [Al+3].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 XEPMXWGXLQIFJN-UHFFFAOYSA-K 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 239000006118 anti-smudge coating Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000987 azo dye Substances 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
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 229940043397 deconex Drugs 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- QPADNTZLUBYNEN-UHFFFAOYSA-N etallobarbital Chemical compound C=CCC1(CC)C(=O)NC(=O)NC1=O QPADNTZLUBYNEN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002504 iridium compounds Chemical class 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KYKLWYKWCAYAJY-UHFFFAOYSA-N oxotin;zinc Chemical compound [Zn].[Sn]=O KYKLWYKWCAYAJY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 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 1
- HTPJPKXFBLUBPI-UHFFFAOYSA-I pentasodium 5-[[4-[[4-anilino-6-[[8-hydroxy-7-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-3,6-disulfonatonaphthalen-1-yl]amino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].COc1cc(N=Nc2cc(cc3cc(cc(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2c(Nc3nc(Nc4ccccc4)nc(Nc4ccc(cc4)N=Nc4ccc(O)c(c4)C([O-])=O)n3)cc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O HTPJPKXFBLUBPI-UHFFFAOYSA-I 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000006100 radiation absorber Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007651 thermal printing Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- ZVAPIIDBWWULJN-UHFFFAOYSA-N tyrian purple Natural products N1C2=CC(Br)=CC=C2C(=O)C1=C1C(=O)C2=CC=C(Br)C=C2N1 ZVAPIIDBWWULJN-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Classifications
-
- 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
- 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
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
-
- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/854—Arrangements for extracting light from the devices comprising scattering means
-
- 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
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/18—Deposition of organic active material using non-liquid printing techniques, e.g. thermal transfer printing from a donor sheet
-
- 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
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
- H10K85/611—Charge transfer complexes
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
Definitions
- Organic electroluminescent devices include layers of organic materials, at least one of which can conduct a charge.
- organic electroluminescent devices include organic light emitting diodes (OLEDs).
- OEL devices organic light emitting diodes
- OEL devices have potential use in applications such as, for example, lighting applications, backlighting of graphics, pixelated displays, and large emissive graphics.
- OEL devices typically include an organic light emitter layer and optionally one or more charge transport layers, all of which are sandwiched between two electrodes: a cathode and an anode.
- Charge carriers, electrons and holes, are injected from the cathode and anode, respectively.
- Electrons are negatively charged atomic particles and holes are vacant electron energy states that behave as though they are positively charged particles. The charge carriers migrate to the emitter layer, where they combine to emit light.
- This basic OEL device structure can be modified to improve or enhance one or more electrical, chemical, or physical properties of the device. Such modification can include the addition or modification of one or more of the basic layers.
- the present invention relates to organic electroluminescent devices, articles containing the organic electroluminescent devices, and methods of making and using the organic electroluminescent devices and articles.
- One embodiment is an electroluminescent device having multiple layers including, but not limited to, an electrode, an emission layer, and a buffer layer.
- the emission layer includes a light emitting material.
- the buffer layer is disposed between and in electrical communication with the electrode and the emission layer and includes a triarylamine hole transport material and an electron acceptor material.
- the buffer layer optionally includes one or more of a) a polymeric binder, b) a color converting material, and c) light scattering particles.
- Another embodiment is a method of making an electroluminescent device.
- the method includes forming an electrode, coating a buffer layer from solution over the electrode, and disposing an emission layer over the buffer layer.
- the electrode, buffer layer, and emission layer are in electrical communication.
- the emission layer includes a light emitting material.
- the buffer layer includes a triarylamine hole transport material and an electron acceptor material.
- the buffer layer includes one or more of a) a polymeric binder, b) a color converting material, and c) light scattering particles.
- an electroluminescent device having multiple layers including, but not limited to, an electrode, an emission layer, and a buffer layer.
- the emission layer includes a light emitting material.
- the buffer layer is disposed between and in electrical communication with the electrode and the emission layer.
- the buffer layer includes (a) a polymeric hole transport material having triarylamine moieties and (b) an electron acceptor material.
- the buffer layer includes one or more of a) a color converting material, and b) light scattering particles.
- Another embodiment is a method of making an electroluminescent device.
- the method includes forming an electrode, coating a buffer layer from solution over the electrode, and disposing an emission layer over the buffer layer.
- the electrode, buffer layer, and emission layer are in electrical communication.
- the emission layer includes a light emitting material.
- the buffer layer includes (a) a polymeric hole transport material having triarylamine moieties and (b) an electron acceptor material.
- the buffer layer includes one or more of a) a color converting material, and b) light scattering particles.
- FIG. 1 is a schematic side view of an organic electroluminescent display construction
- FIG. 2 is a schematic side view of a first embodiment of an electroluminescent device, according to the present invention.
- FIG. 3 is a schematic side view of a second embodiment of an electroluminescent device, according to the present invention.
- FIG. 4 is a schematic side view of a third embodiment of an electroluminescent device, according to the present invention.
- FIG. 5 is a schematic side view of an organic electroluminescent display according to the present invention.
- the present invention is believed to be applicable to electroluminescent devices, articles containing the electroluminescent devices, and methods of making and using the electroluminescent devices and articles.
- the present invention is directed to organic electroluminescent devices containing a buffer layer with a triarylamine material and an electron acceptor material, articles containing the organic electroluminescent devices, and methods of making and using the organic electroluminescent devices and articles.
- Pixelated and non-pixelated electroluminescent displays, backlights, and other lighting components are examples of some of the articles that can include organic electroluminescent devices. While the present invention is not so limited, an appreciation of various aspects of the invention will be gained through a discussion of the examples provided below.
- Organic electroluminescent device refers to an electroluminescent device that includes an organic emissive material.
- the emissive material can include, for example, a small molecule (SM) emitter, a SM doped polymer, a light emitting polymer (LEP), a doped LEP, a blended LEP, or any combination of these materials.
- SM small molecule
- LEP light emitting polymer
- This emissive material can be provided alone or in combination with any other organic or inorganic materials, including, for example, binders, color converting materials, and scattering materials, that are functional or non-functional in the organic electroluminescent device.
- R. H. Friend, et al. (“Electroluminescence in Conjugated Polymers” Nature, 397, 1999, 121, incorporated herein by reference) describe one mechanism of electroluminescence as including the “injection of electrons from one electrode and holes from the other, the capture of oppositely charged carriers (so-called recombination), and the radiative decay of the excited electron-hole state (exciton) produced by this recombination process.”
- FIG. 1 illustrates an organic electroluminescent device 100 that includes a device layer 110 and a substrate 120 . Any other suitable device component can also be included with the device 100 .
- additional optical elements or other devices suitable for use with electronic displays, devices, or lamps can be provided between the display 100 and a viewer position 140 as indicated by an optional element 130 .
- Substrate 120 can be any substrate suitable for the electroluminescent device application.
- substrate 120 can include glass, clear plastic, or other suitable material(s) that are substantially transparent to visible light.
- suitable plastic substrates include those made of polymers such as polyolefins, polyethersulfones, polycarbonates, polyesters, and polyarylates.
- Substrate 120 can also be opaque to visible light such as, for example, stainless steel, crystalline silicon, poly-silicon, or the like. Because some materials in electroluminescent devices can be particularly susceptible to damage due to exposure to oxygen or water, substrate 120 preferably provides an adequate environmental barrier or is supplied with one or more layers, coatings, or laminates that provide an adequate environmental barrier.
- Substrate 120 can also include any number of devices or components suitable in electroluminescent devices and displays such as, for example, transistor arrays and other electronic devices; color filters, polarizers, wave plates, diffusers, and other optical devices; insulators, barrier ribs, black matrix, mask works and other such components; and the like.
- one or more electrodes is coated, deposited, patterned, or otherwise disposed on substrate 120 before forming the remaining layer or layers of the electroluminescent device or devices of the device layer 110 .
- the electrode or electrodes that are disposed between the substrate 120 and the emissive material(s) are preferably substantially transparent to light.
- transparent conductive electrodes such as indium tin oxide (ITO) or any of a number of other semi-transparent or transparent conductive oxides or nitrides, or semi-transparent or transparent metals can be used.
- Element 130 can be any element or combination of elements suitable for use with electroluminescent device 100 .
- element 130 can be an LCD module when device 100 is a backlight.
- One or more polarizers or other elements can be provided between the LCD module and the backlight device 100 , for instance an absorbing or reflective clean-up polarizer.
- element 130 can include one or more of polarizers, wave plates, touch panels, antireflective coatings, anti-smudge coatings, projection screens, brightness enhancement films, scattering films, light extraction films, refractive index gradient films, or other optical components, coatings, user interface devices, or the like.
- device layer 110 includes one or more electroluminescent devices that emit light through the substrate toward a viewer position 140 .
- the viewer position 140 is used generically to indicate an intended destination for the emitted light whether it be an actual human observer, a screen, an optical component, an electronic device, or the like.
- device layer 110 is positioned between substrate 120 and the viewer position 140 .
- the device configuration shown in FIG. 1 may be used when, for example, substrate 120 is transmissive to light emitted by device layer 110 and when a transparent conductive electrode is disposed in the device between the emissive layer of the device and the substrate.
- the inverted configuration may be used when, for example, substrate 120 does or does not transmit the light emitted by the device layer and the electrode disposed between the substrate and the light emitting layer of the device does not transmit the light emitted by the device.
- the device may emit from both the top and bottom, in which case both conductive electrodes are preferably transparent or semi-transparent.
- Device layer 110 can include one or more electroluminescent devices arranged in any suitable manner.
- device layer 110 in lamp applications (e.g., backlights for liquid crystal display (LCD) modules), device layer 110 can constitute a single electroluminescent device that spans an entire intended backlight area.
- device layer 110 in other lamp applications, device layer 110 can constitute a plurality of closely spaced electroluminescent devices that can be contemporaneously activated. For example, relatively small and closely spaced red, green, and blue light emitters can be patterned between common electrodes so that device layer 110 appears to emit white light when the emitters are activated. Other arrangements for backlight applications are also contemplated.
- device layer 110 may include a plurality of independently addressable electroluminescent devices that emit the same or different colors.
- Each device can represent a separate pixel or a separate sub-pixel of a pixilated display (e.g., high resolution display), a separate segment or sub-segment of a segmented display (e.g., low information content display), or a separate icon, portion of an icon, or lamp for an icon (e.g., indicator applications).
- an electroluminescent device includes a thin layer, or layers, of one or more suitable materials sandwiched between a cathode and an anode.
- electrons are injected into the layer(s) from the cathode and holes are injected into the layer(s) from the anode.
- the charges can recombine to form electron-hole pairs which are typically referred to as excitons.
- the region of the device in which the exitons are generally formed can be referred to as the recombination zone.
- These excitons, or excited state species can emit energy in the form of light as they decay back to a ground state.
- Electroluminescent devices such as hole transport layers, electron transport layers, hole injection layers, electron injection layers, hole blocking layers, electron blocking layers, buffer layers, and the like.
- photoluminescent materials can be present in the electroluminescent or other layers in electroluminescent devices, for example, to convert the color of light emitted by the electroluminescent material to another color.
- These and other such layers and materials can be used to alter or tune the electronic properties and behavior of the layered electroluminescent device, for example, to achieve one or more features such as a desired current/voltage response, a desired device efficiency, a desired color, a desired brightness, a desired device lifetime, or a desired combination of these features.
- FIGS. 2, 3, and 4 illustrate examples of different electroluminescent device configurations where like elements are provided the same reference numeral.
- Each configuration includes a substrate 250 , an anode 252 , a buffer layer 254 , an emission layer 256 , and a cathode 258 .
- the configurations of FIGS. 3 and 4 also include a hole transport layer 260 between the buffer layer 254 and the emission layer 256 . Alternatively or additionally, a hole transport layer (not shown) may be positioned between the anode and the buffer layer.
- the configuration of FIG. 4 includes an electron transport or electron injection layer 262 .
- the substrate 250 can be made of any of the materials discussed with respect to substrate 120 of FIG. 1.
- a hole injection layer, electron injection layer, or both can also be added or the hole transport layer 260 could be removed.
- the buffer layer 254 acts, at least in part, as a hole injection layer or hole transport layer.
- any of the layers illustrated in FIGS. 2, 3, and 4 can be formed using a single layer of material or multiple layers of the same or different materials. The material for each layer can be a single compound or a combination of two or more different compounds.
- the anode 252 and cathode 258 are typically formed using conducting materials such as metals, alloys, metallic compounds, metal oxides, conductive ceramics, conductive dispersions, and conductive polymers, including, for example, gold, silver, copper, platinum, palladium, aluminum, calcium, barium, magnesium, titanium, titanium nitride, indium oxide, indium tin oxide (ITO), vanadium oxide, zinc tin oxide, fluorine tin oxide (FTO), polyaniline, polypyrrole, polythiophene, and combinations or alloys of these materials.
- the anode 252 and the cathode 258 can be single layers of conducting materials or they can include multiple layers.
- an anode or a cathode can include a layer of aluminum and a layer of gold, a layer of calcium and a layer of aluminum, a layer of lithium fluoride and a layer of aluminum, a layer of magnesium and silver, a layer of magnesium and silver followed by another layer of silver, or a metal layer and a conductive organic layer.
- the emission layer 256 includes one or more light emitting materials, such as a small molecule (SM) emitter, a SM doped polymer, a light emitting polymer (LEP), a doped LEP, a blended LEP, another organic emissive material, or any combination of these materials.
- SM small molecule
- LEP light emitting polymer
- suitable LEP materials include poly(phenylenevinylene)s (PPVs), poly-para-phenylenes (PPPs), polyfluorenes (PFs), other LEP materials now known or later developed, and co-polymers or blends thereof.
- Suitable LEPs can also be molecularly doped, dispersed with luminescent dyes or other photoluminescent (PL) materials, blended with active or non-active materials, dispersed with active or non-active materials, and the like.
- suitable LEP materials are described in, for example, Kraft, et al., Angew. Chem. Int. Ed., 37, 402-428 (1998); U.S. Pat. Nos. 5,621,131; 5,708,130; 5,728,801; 5,840,217; 5,869,350; 5,900,327; 5,929,194; 6,132,641; and 6,169,163; and PCT Patent Application Publication No. 99/40655, all of which are incorporated herein by reference.
- SM materials are generally non-polymer organic or organometallic molecular materials that can be used in organic electroluminescent displays and devices as emitter materials, charge transport materials, as dopants in emitter layers (e.g., to control the emitted color) or charge transport layers, and the like.
- Commonly used SM materials include metal chelate compounds, for example, tris(8-hydroxyquinoline) aluminum (AlQ) and derivatives thereof, and organic compounds, for example, N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD).
- metal chelate compounds for example, tris(8-hydroxyquinoline) aluminum (AlQ) and derivatives thereof
- organic compounds for example, N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD).
- TPD N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine
- the optional hole transport layer 260 facilitates the injection of holes from the anode into the device and their migration towards the recombination zone.
- the hole transport layer 260 can further act as a barrier for the passage of electrons to the anode 252 .
- the hole transport layer 260 can include, for example, a diamine derivative, such as N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (also known as TPD) or N,N′-bis(3-naphthalen-2-yl)-N,N′-bis(phenyl)benzidine (NPD), or a triarylamine derivative, such as, 4,4′,4′′-Tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4′′-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA), 4,4′,4′′-tri(N-phenothiazinyl) triphenylamine (TPTTA), 4,4′,4′′-tri(N-phenoxazinyl) triphenylamine (TPOTA).
- a diamine derivative such as N,N′-bis(3-methylphenyl)-N,N′
- CuPC copper phthalocyanine
- TDAPBs 1,3,5-Tris(4-diphenylaminophenyl)benzenes
- poly(vinyl carbazole) examples include copper phthalocyanine (CuPC); 1,3,5-Tris(4-diphenylaminophenyl)benzenes (TDAPBs); poly(vinyl carbazole); and other compounds such as those described in Shirota, J. Mater. Chem., 10, 1 (2000), H. Fujikawa, et al., Synthetic Metals, 91, 161 (1997), and J. V. Grazulevicius, P. Strohriegl, “Charge-Transporting Polymers and Molecular Glasses”, Handbook of Advanced Electronic and Photonic Materials and Devices, H. S. Nalwa (ed.), 10, 233-274 (2001), all of which are incorporated herein by reference.
- CuPC copper phthalocyanine
- TDAPBs 1,3,5-Tris(
- the optional electron transport layer 262 facilitates the injection of electrons and their migration towards the recombination zone.
- the electron transport layer 262 can further act as a barrier for the passage of holes to the cathode 258 , if desired.
- the electron transport layer 262 can be formed using the organometallic compound tris(8-hydroxyquinolato) aluminum (AlQ).
- electron transport materials include 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 1,3-bis[5-(4-(1,1-dimethylethyl)phenyl)-1,3,4-oxadiazol-2-yl]benzene, 2-(biphenyl-4-yl)-5-(4-(1,1-dimethylethyl)phenyl)-1,3,4-oxadiazole (tBuPBD) and other compounds described in Shirota, J. Mater. Chem., 10, 1 (2000), C. H. Chen, et al., Macromol. Symp.
- the buffer layer 254 facilitates the injection of holes from the anode into the hole transport layer 260 or emission layer 256 .
- the buffer layer may also assist in planarization of previously formed layers, such as the anode. This planarization may also assist in reducing or eliminating short circuits due to non-uniformity in the anode.
- the buffer layer may facilitate formation of other layers on the buffer layer, including the forming of other layers by thermal transfer onto the buffer layer.
- the buffer layer includes a triarylamine material and an electron acceptor material.
- the triarylamine material includes at least one compound, including polymers, that has one or more triarylamine moieties with formula 1:
- Ar 1 , Ar 2 , and Ar 3 are substituted or unsubstituted aryl or arylene functional groups and where, optionally, the triarylamine moiety(ies) is/are coupled to other portions of the compound through one or more of the arylene functional groups, if present.
- suitable materials include triphenylamine and biphenyldiamines such as, for example, N,N′-bis(naphthalene-2-yl)-N,N′-bis(phenyl)benzidine (NPD), N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD), and 4,4′-bis(carbazol-9-yl)biphenyl (CPB).
- NPD N,N′-bis(naphthalene-2-yl)-N,N′-bis(phenyl)benzidine
- TPD N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine
- CPB 4,4′-bis(carbazol-9-yl)biphenyl
- triarylamine compounds with tetrahedral cores such as compounds having formulas 2, 3, and 4:
- each R 1 is independently selected (i.e., each R 1 can be the same or different from the other R 1 substituents in the formula) from triarylamine moieties (including moieties which form a triarylamine structure in combination with the phenyl group to which R 1 is attached).
- triarylamine moieties include formulas 5, 6, 7, and 8:
- R 2 is alkyl or aryl and each R 3 , R 4 , and R 5 is independently H, alkyl, aryl, alkoxy, aryloxy, halo, alkylthio, arylthio, or —NR a R b , where R a and R b are aryl or alkyl.
- R a and R b are aryl or alkyl.
- all R 3 are the same
- all R 4 are the same
- all R 5 are the same, or any combination thereof (e.g., all R 3 and R 4 are the same).
- Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted including, for example, fluorinated and perfluorinated alkyls.
- the triarylamine material preferably incorporates one or more arylenediamine linkages of the formula 9:
- Ar 4 , Ar 5 , Ar 6 , Ar 7 , and Ar 8 are substituted or unsubstituted aryl or arylene groups and where, optionally, the arylenediamine linkage(s) is/are coupled to other portions of the compound through one or more of the arylene functional groups, if present.
- One preferred arylenediamine linkage is a phenylenediamine linkage where Ar 8 is a phenylene group. Examples of suitable compounds of this type include those compounds illustrated in Formulas 10-12:
- each R 2 is independently alkyl or aryl and each R 3 and R 4 is independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NR a R b , where R a and R b are aryl or alkyl.
- R a and R b are aryl or alkyl.
- one of the following conditions applies: all of the R 3 and R 4 substituents are the same; all of the R 3 substituents are the same; all of the R 4 substituents are the same; or all of the R 3 substituents and all of the R 4 substituents are the same, but R 3 and R 4 are different.
- suitable compounds of this type include 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine (TDATA) (Formula 13), 4,4′,4′′-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA) (Formula 14), 4,4′,4′′-tris(carbozol-9-yl)triphenylamine (TCTA) (Formula 15), 4,4′,4′′-tris(N-naphthyl-N-phenylamino)triphenylamine (2-TNATA) (Formula 16):
- polymeric materials with triarylamine moieties can be used as an alternative to small molecule triarylamine materials.
- the triarylamine moieties can be in the backbone of the polymeric material, can be pendent groups extending from the backbone of the polymeric material, or both.
- Polymers with triarylamine moieties in the backbone include, for example, the polymers of Formulas 18, 19, 20, and 21:
- R 3 and R 4 are independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NR a R b , where R a and R b are aryl or alkyl, Ar 9 is aryl or arylene, CM is one or more comonomers, n is an integer of three or greater and preferably 10 or greater, and m is an integer of zero or greater. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted.
- Suitable comonomers, CM include, for example, another triarylamine-containing monomer such as those illustrated in Formulas 18-21 or 33-34 below, arylene (including substituted or unsubstituted para- or meta-phenylene), substituted or unsubstituted styrene comonomers, derivatized carbazole comonomers (such as N-alkyl carbazole or N-aryl carbazole, for example, the comomoners as illustrated in Formulas 29 and 32), ether- and polyether-linked comonomers, carbonate comonomers, urethane-linked comonomers, thioether-linked comonomers, ester-linked comonomers, and imide- and amide-linked comonomers.
- carbazole comonomers such as N-alkyl carbazole or N-aryl carbazole, for example, the comomoners as illustrated in Formulas 29 and 32
- Such comonomers include, but are not limited to, —O—(C n H 2n O)— and —Ar 10 —O—(C n H 2n O)—A 11 — where Ar 10 and Ar 11 are arylene.
- the comonomer contains one or more photo- or thermocrosslinking functional groups, such a benzocyclobutene (Formula 22) or acrylate or methacrylate groups, such as, for example, the acrylate group of Formula 23.
- photo- or thermocrosslinking functional groups such as a benzocyclobutene (Formula 22) or acrylate or methacrylate groups, such as, for example, the acrylate group of Formula 23.
- cross-linkable moieties are described in, for example, PCT Patent Application Publication No. WO 97/33193, incorporated herein by reference.
- the polymers containing such cross-linkable moieties are selected to crosslink under relatively mild photochemical or thermal conditions.
- thermal crosslinking may occur at 100 to 150° C.
- UV-visible radiation in the range of 300 to 700 nm might be used to crosslink the polymers.
- the comonomer is copolymerized with the triarylamine-containing monomer unit.
- the comonomer can be coupled to the triarylamine-containing monomer unit prior to polymerization.
- Such a polymer might not be considered a copolymer, but rather a homopolymer with the coupled triarylamine-containing unit/comonomer unit as the basic monomer unit of the polymer. Examples of such polymers are illustrated by Formulas 24-27.
- polymers of Formulas 24-27 include the polymers of Formulas 28-32:
- the comonomer unit is coupled to the triarylamine moiety-containing monomer unit in such a way that the two monomer units alternate in the polymer.
- Formulas 33 and 34 illustrate polymers with triarylamine pendent groups:
- R 3 , R 4 , and R 5 are independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NR a R b , where R a and R b are aryl or alkyl, CM is one or more comonomers, n is an integer of three or greater and preferably 10 or greater, and m is an integer of zero or greater. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted.
- Suitable comonomers include, for example, another triarylamine-containing monomer containing one or more chain polymerizable moieties, arylenes (including substituted or unsubstituted para- or meta-phenylene) with one or more chain polymerizable moieties, derivatized carbazole comonomers (such as N-vinyl carbazole), carbonate comonomers, urethane-linked comonomers, thioether-linked comonomers, ester-linked comonomers, imide- and amide-linked comonomers, substituted or unsubstituted styrene comonomers, (meth)acrylate comonomers of, for example, C1-C12 alcohols, diene comonomers such as, for example, butadiene, isoprene and 1,3 cyclohexadiene, and other chain-polymerizable comonomers.
- the comonomer is copolymerized with the triarylamine-containing monomer unit.
- the comonomer can be coupled to the triarylamine-containing monomer unit prior to polymerization.
- Such a polymer might not be considered a copolymer, but rather a homopolymer with the coupled triarylamine-containing unit/comonomer unit as the basic monomer unit of the polymer.
- One example is illustrated as Formula 35.
- the pendent groups can also extend from backbone moieties other than the ethylene moieties illustrated in Formulas 33 and 34.
- backbone units from which the triarylamine pendent groups can extend include, for example, alkylene (such as propylene, butylenes, isoprene, or 1,3-cyclohexadiene), silane, arylenes (including substituted or unsubstituted para- or meta-phenylene), derivatized carbazole monomers (as illustrated in Formulas 29 and 32), carbonate monomers, urethane-linked monomers, thioethers-linked monomers, ester-linked monomers, imide- and amide-linked monomers, substituted and unsubstituted styrene monomers, and (meth)acrylate monomers.
- alkylene such as propylene, butylenes, isoprene, or 1,3-cyclohexadiene
- silane such as propylene, butylenes, isopre
- suitable polymers with pendent triarylamine groups include, for example, the polymers of Formulas 36-38:
- each R 3 , R 4 , R 5 , R 6 , and R 7 is independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NR a R b , where R a and R b are aryl or alkyl.
- R a and R b are aryl or alkyl.
- R 3 , R 4 , and R 5 substituents are the same; all of the R 3 substituents are the same; all of the R 4 substituents are the same; all of the R 5 substituents are the same; all of the R 7 substituents are the same; or all of the R 3 substituents and all of the R 4 substituents are the same, but R 3 and R 4 are different.
- R 3 , R 5 , R 6 , and R 7 can be H and R 4 can be methyl in any of Formulas 36-38.
- alkyl includes both straight-chained, branched, and cyclic alkyl groups and includes both unsubstituted and substituted alkyl groups. Unless otherwise indicated, the alkyl groups are typically C1-C20. Examples of “alkyl” as used herein include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, isobutyl, and isopropyl, and the like.
- aryl refers to monovalent unsaturated aromatic carbocyclic radicals having one to fifteen rings, such as phenyl or bipheynyl, or multiple fused rings, such as naphthyl or anthryl, or combinations thereof.
- aryl as used herein include, but are not limited to, phenyl, 2-naphthyl, 1-naphthyl, biphenyl, 2-hydroxyphenyl, 2-aminophenyl, 2-methoxyphenyl and the like.
- arylene refers to divalent unsaturated aromatic carbocyclic radicals having one to fifteen rings, such as phenylene, or multiple fused rings, such as fluorene, naphthylene or anthrylene, or combinations thereof.
- arylene as used herein include, but are not limited to, benzene-1,2-diyl, benzene-1,3-diyl, benzene-1,4-diyl, naphthalene-1,8-diyl, anthracene-1,4-diyl, fluorene, phenylenevinylene, phenylenedivinylene, and the like.
- alkoxy refers to the functional group —OR where R is a substituted or unsubstituted alkyl group. Unless otherwise indicated, the alkyl group is typically C1-C20. Examples of “alkoxy” as used herein include, but are not limited to, methoxy, ethoxy, n-propoxy, and 1-methylethoxy, and the like.
- aryloxy refers to the functional group —OAr where Ar is a substituted or unsubstituted aryl group.
- aryloxy as used herein include, but are not limited to, phenyloxy, naphthyloxy, and the like.
- Suitable substituents for substituted alkyl, aryl, and arylene groups include, but are not limited to, alkyl, alkylene, aryl, arylene, heteroaryl, heteroarylene, alkenyl, alkenylene, —NRR′, F, Cl, Br, I, —OR, —SR, cyano, nitro, —COOH, and —COO-alkyl where R and R′ are independently hydrogen, alkyl, or aryl.
- halo includes fluoro, chloro, bromo, and iodo.
- polymer includes homopolymers and copolymers including block copolymers and random copolymers.
- the buffer layer also includes an electron acceptor material to improve electron transport.
- an electron acceptor material to improve electron transport.
- such compounds have relatively high electron affinity and relatively low energy of the lowest unoccupied molecular orbital (LUMO).
- Suitable electron acceptor materials include electron deficient compounds such as, for example, tetracyanoquinodimethane and derivatives, thiopyranylidines, polynitrofluorenones, tetracyanoethylene (TCNE), chloranil, and other compounds commonly used as electron acceptors in charge transfer materials and electrophotography.
- electron acceptor materials include tetracyanoquinodimethane (TCNQ) (Formula 39), tetrafluoro-tetracyanoquinodimethane (F 4 -TCNQ) (Formula 40), tetracyanoethylene, chloranil, 2-(4-(1-methylethyl)phenyl-6-phenyl-4H-thiopyran-4-ylidene)-propanedinitrile-1,1-dioxyide (PTYPD) (Formula 41), and 2,4,7-trinitrofluorenone (Formula 42).
- TCNQ tetracyanoquinodimethane
- F 4 -TCNQ tetrafluoro-tetracyanoquinodimethane
- PTYPD 2-(4-(1-methylethyl)phenyl-6-phenyl-4H-thiopyran-4-ylidene)-propanedinitrile-1,1-dioxyide
- the electron acceptor material is soluble in one or more organic solvents, more preferably, one or more organic solvents in which the triarylamine material is also soluble.
- the electron donor material is present in the buffer layer in the range of 0.5 to 20 wt. % of the triarylamine material. In some embodiments, the electron donor material is present in the buffer layer in the range of 1 to 5 wt. % of the triarylamine material.
- the buffer layer optionally includes a polymeric binder.
- the polymeric binder can include inert or electroactive polymers or combinations thereof. Suitable polymers for the polymeric binder include, for example, polystyrene, poly(N-vinyl carbazole), polyfluorenes, poly(para-phenylenes), poly(phenylenevinylenes), polycarbonates, polyimides, polyolefins, polyacrylates, polymethacrylates (for example, poly(methylmethacrylate)), polyethers, polysulfones, polyether ketones, and copolymers or mixtures thereof.
- the triarylamine material includes a triarylamine-containing polymer
- that polymer can act as or in cooperation with a polymeric binder, if desired.
- the polymeric binder is typically provided in the range of 20 to 150 wt. %, preferably 70 to 120 wt. %, of the triarylamine material.
- the polymeric binder can be photochemically or thermally crosslinked with itself or with other components in the buffer layer.
- a thermochemical or photochemical crosslinking agent such as, for example, 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone, can optionally be included in the buffer layer.
- Crosslinking can be desirable for one or more purposes, such as decreasing the migration of buffer layer components out of the buffer layer, decreasing the migration of other materials into the buffer layer, increasing thermal stability, increasing mechanical stability, increasing morphological stability, increasing buffer layer stability, and increasing layer integrity, particularly during further solution processing.
- Crosslinking the buffer layer can also facilitate manufacture of a device by providing a buffer layer upon which other layers can be solution coated or cast with substantially less concern about dissolving the buffer layer.
- the buffer layer can optionally include a color converting material.
- This material can be a luminescent or non-luminescent organic, organometallic, or inorganic compound or combinations thereof.
- the color converting material changes the color of electroluminescence from an emitting layer by selective absorption of light or by absorption of light and re-emission of the light in a different spectral range.
- Suitable materials include, for example, dyes, pigments, and nanoparticles.
- suitable non-luminescent and luminescent dyes include: azo dyes (e.g. C.I. Direct Green 26 and others), anthraquinone dyes (e.g. C.I. Reactive Blue 4 and others), indigoid dyes (e.g.
- triphenylmethane-based dyes e.g. Eosin and others
- coumarin dyes e.g. Coumarin 6 and others
- metal porphyrins e.g. platinum [II] octaethylporphyrin and others
- cyclometalated transition metal complexes e.g. iridium tris(2-phenylpyridine) and others
- other dyes including those discussed in H. Zollinger, Color Chemistry, 1991, VCH Publishers: New York, and The Chemistry and Application of Dyes, Ed. By D. R. Waring and G. Halls, 1990, Plenum Press: New York, both of which are incorporated herein by reference.
- the color converting material can be polymeric with color converting moieties in the backbone, on pendant chains, or both.
- the color converting material, if used, is typically included in the buffer layer in an amount in the range of 0.1 to 100 wt. %, preferably 0.1 to 10 wt. %, of the triarylamine material.
- the buffer layer can also optionally include scattering material, such as small particles, nanocrystals, or clusters.
- suitable materials include clays, oxides, metals, and glasses.
- Specific examples of suitable materials include titania, alumina and silica powders having a mean particle size of approximately 0.05 to 0.2 microns, and added to the buffer layer composition in a concentration of from 0.1 to 20% by weight, and preferably from about 1-5% by weight.
- the buffer layer 254 is formed by solution coating the material of the buffer layer onto the substrate 250. After formation of the buffer layer 254, additional layers, such as the hole transport layer 260 or emission layer 256, can be formed on the buffer layer by a variety of techniques including, for example, solution coating, physical or chemical vapor deposition, and thermal transfer, including light-induced thermal transfer as described below.
- An organic solvent is used to make the solution for the buffer layer.
- suitable organic solvents include carbon tetrachloride, toluene, chloroform, 1,2-dichloroethane, 1,2-dichlorobenzene, tetrahydrofuran, pyridine, and the like.
- the remaining materials of the buffer layer are typically dispersible or, preferably, soluble in the organic solvent.
- the materials of a layer are disposed by vapor deposition.
- a number of materials are difficult to accurately and consistently deposit by vapor deposition methods. Included in these materials are a variety of polymers and ionic compounds. Thus, it can be difficult to deposit materials such as a polymeric binder and cross-linking agent using vapor deposition techniques. In addition, the consistency and uniformity of a vapor deposited composition becomes increasingly difficult when the composition contains multiple components.
- forming a buffer layer by solution coating can facilitate the use of materials such as polymeric binders, polymeric triarylamine materials, crosslinking agents, dyes, pigments, scattering particles, and so on.
- the coating technique permits the use of multi-component systems when all of the components are soluble or dispersible in the solvent.
- the buffer layer material can be coated onto a donor sheet and then transferred by techniques such as thermal transfer to the substrate. This can be particularly useful for patterning the buffer layer onto the substrate.
- the buffer layer material can be selectively transferred from the donor sheet to the substrate according to a pattern by selective application of, for example, light or heat to the donor sheet. This can be useful, for example, to pattern individual buffer layers with a different color converting materials (or lack of color converting material) onto the substrate.
- a full-color display could be formed using, for example, three different buffer layers with three different color converting materials (or two different color converting materials and the third buffer layer lacking a color converting material).
- Other methods of selectively patterning color converting materials in buffer layer(s) include, for example, thermal diffusion of the color converting material, inkjet transfer of the buffer material with (or without) color converting materials onto the substrate, and selective photobleaching.
- Suitable thermal transfer methods for transferring a buffer layer or other device layers to the substrate or onto a previously-formed buffer layer include, for example, thermal head transfer methods and light-induced thermal transfer methods.
- the presence of the buffer layer on the substrate can, at least in some instances, facilitate the transfer of other layers to the substrate by these methods.
- Materials, layers, or other structures can be selectively transferred from the transfer layer of a donor sheet to a receptor substrate by placing the transfer layer of the donor element adjacent to the receptor and selectively heating the donor element.
- the donor element can be selectively heated by irradiating the donor element with imaging radiation that can be absorbed by light-to-heat converter material disposed in the donor, often in a separate light-to-heat conversion (LTHC) layer, and converted into heat.
- LTHC light-to-heat conversion
- the donor can be exposed to imaging radiation through the donor substrate, through the receptor, or both.
- the radiation can include one or more wavelengths, including visible light, infrared radiation, or ultraviolet radiation, for example from a laser, lamp, or other radiation source.
- thermal print heads or other heating elements may be particularly suited for making lower resolution patterns of material or for patterning elements whose placement need not be precisely controlled.
- Material from the transfer layer can be selectively transferred to a receptor in this manner to imagewise form patterns of the transferred material on the receptor.
- thermal transfer using light from, for example, a lamp or laser, to patternwise expose the donor can be advantageous because of the accuracy and precision that can often be achieved.
- the size and shape of the transferred pattern (e.g., a line, circle, square, or other shape) can be controlled by, for example, selecting the size of the light beam, the exposure pattern of the light beam, the duration of directed beam contact with the donor sheet, or the materials of the donor sheet.
- the transferred pattern can also be controlled by irradiating the donor element through a mask.
- Transfer layers can also be transferred from donor sheets without selectively transferring the transfer layer.
- a transfer layer can be formed on a donor substrate that, in essence, acts as a temporary liner that can be released after the transfer layer is contacted to a receptor substrate, typically with the application of heat or pressure.
- lamination transfer can be used to transfer the entire transfer layer, or a large portion thereof, to the receptor.
- a donor sheet for light-induced thermal transfer can include, for example, a donor substrate, an optional underlayer, an optional light-to-heat conversion (LTHC) layer, an optional interlayer, and a transfer layer.
- the donor substrate can be a polymer film or any other suitable, preferably transparent, substrate.
- the donor substrate is also typically selected from materials that remain stable despite heating of one or more layers of the donor.
- the inclusion of an underlayer between the substrate and an LTHC layer can be used to insulate the substrate from heat generated in the LTHC layer during imaging.
- the underlayer can include materials that impart desired mechanical or thermal properties to the donor element.
- the underlayer can include materials that exhibit a low value for the mathematical product of specific heat and density or low thermal conductivity relative to the donor substrate. Such an underlayer may be used to increase heat flow to the transfer layer, for example to improve the imaging sensitivity of the donor.
- the underlayer can also include materials for their mechanical properties or for adhesion between the substrate and the LTHC.
- An LTHC layer can be included in donor sheets of the present invention to couple irradiation energy into the donor sheet.
- the LTHC layer preferably includes a radiation absorber that absorbs incident radiation (e.g., laser light) and converts at least a portion of the incident radiation into heat to enable transfer of the transfer layer from the donor sheet to the receptor.
- An optional interlayer can be disposed between the LTHC layer and transfer layer.
- the interlayer can be used, for example, to minimize damage and contamination of the transferred portion of the transfer layer and may also reduce distortion in the transferred portion of the transfer layer.
- the interlayer can also influence the adhesion of the transfer layer to the rest of the donor sheet.
- the interlayer has high thermal resistance.
- the interlayer does not distort or chemically decompose under the imaging conditions, particularly to an extent that renders the transferred image non-functional.
- the interlayer typically remains in contact with the LTHC layer during the transfer process and is not substantially transferred with the transfer layer.
- the interlayer can provide a number of benefits, if desired.
- the interlayer can be a barrier against the transfer of material from the light-to-heat conversion layer. It can also modulate the temperature attained in the transfer layer so that thermally unstable materials can be transferred.
- the interlayer can act as a thermal diffuser to control the temperature at the interface between the interlayer and the transfer layer relative to the temperature attained in the LTHC layer. This can improve the quality (i.e., surface roughness, edge roughness, etc.) of the transferred layer.
- the presence of an interlayer can also result in improved plastic memory in the transferred material.
- the thermal transfer layer includes the buffer material to form the buffer layer, if desired, or appropriate materials to form other layers depending on the desired thermal transfer.
- other layers of the device such as the hole transport layer or the emission layer, can be transferred onto the substrate or onto the buffer layer or other layers disposed on the substrate by these methods.
- Such transfer can be sequential using multiple donor sheets or, in some embodiments, multiple layers can be transferred using a single donor sheet with the transfer layer having individual sublayers.
- OEL displays can be made that emit light and that have adjacent devices that can emit light having different color.
- FIG. 5 shows an OEL display 300 that includes a plurality of OEL devices 310 disposed on a substrate 320 . Adjacent devices 310 can be made to emit different colors of light.
- Adjacent devices may be separated, in contact, overlapping, etc., or different combinations of these in more than one direction on the display substrate.
- Adjacent devices may be separated, in contact, overlapping, etc., or different combinations of these in more than one direction on the display substrate.
- a pattern of parallel striped transparent conductive anodes can be formed on the substrate followed by a striped pattern of a hole transport material and a striped repeating pattern of red, green, and blue light emitting LEP layers, followed by a striped pattern of cathodes, the cathode stripes oriented perpendicular to the anode stripes.
- Such a construction may be suitable for forming passive matrix displays.
- transparent conductive anode pads can be provided in a two-dimensional pattern on the substrate and associated with addressing electronics such as one or more transistors, capacitors, etc., such as are suitable for making active matrix displays.
- addressing electronics such as one or more transistors, capacitors, etc.
- Other layers, including the light emitting layer(s) can then be coated or deposited as a single layer or can be patterned (e.g., parallel stripes, two-dimensional pattern commensurate with the anodes, etc.) over the anodes or electronic devices. Any other suitable construction is also contemplated by the present invention.
- display 300 can be a multiple color display. As such, it may be desirable to position optional polarizer 330 between the light emitting devices and a viewer, for example to enhance the contrast of the display.
- each of the devices 310 emits light.
- FIG. 3 There are many displays and devices constructions covered by the general construction illustrated in FIG. 3. Some of those constructions are discussed as follows.
- OEL backlights can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like.
- Applications include white or single color large area single pixel lamps, for example where an emissive material is provided by thermal stamp transfer, lamination transfer, resistive head thermal printing, or the like; white or single color large area single electrode pair lamps that have a large number of closely spaced emissive layers patterned by laser induced thermal transfer; and tunable color multiple electrode large area lamps.
- Low resolution OEL displays can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like.
- Applications include graphic indicator lamps (e.g., icons); segmented alphanumeric displays (e.g., appliance time indicators); small monochrome passive or active matrix displays; small monochrome passive or active matrix displays plus graphic indicator lamps as part of an integrated display (e.g., cell phone displays); large area pixel display tiles (e.g., a plurality of modules, or tiles, each having a relatively small number of pixels), such as may be suitable for outdoor display used; and security display applications.
- graphic indicator lamps e.g., icons
- segmented alphanumeric displays e.g., appliance time indicators
- small monochrome passive or active matrix displays e.g., small monochrome passive or active matrix displays plus graphic indicator lamps as part of an integrated display (e.g., cell phone displays); large area pixel display tiles (e.g., a plurality of modules, or tiles, each having a relatively small number of pixels), such as may be suitable for outdoor display used; and security display applications.
- High resolution OEL displays can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like. Applications include active or passive matrix multicolor or full color displays; active or passive matrix multicolor or full color displays plus segmented or graphic indicator lamps (e.g., laser induced transfer of high resolution devices plus thermal hot stamp of icons on the same substrate); and security display applications.
- ITO substrates were prepared as follows: ITO (indium tin oxide) glass substrates (Applied Films Corporation, CO; ca. 25 ⁇ /sq.) were rinsed in acetone (Aldrich Chemical Company), dried with nitrogen, and rubbed with TX1010 Vectra Sealed-Border Wipers (ITW Texwipe, Upper Saddle River, N.J.) soaked in methanol (Aldrich Chemical Company, Milwaukee, Wis.), after which they were subjected to oxygen plasma treatment for four minutes at 200 mT (about 27 Pa) base oxygen pressure and output power of 50 W in Technics Micro Reactive Ion Etcher, Series 80 (K&M Company, CA).
- the OLED's described below were generally 1 to 1.5 cm 2 in size.
- This Example describes the formation of OLEDs having a solution-processed hole-injecting buffer layer incorporating 4,4′,4′′-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA) as a triarylamine material, polystyrene (PS) as an electrically inert polymer binder, and tetrafluoro-tetracyanoquinodimethane (F 4 -TCNQ) or tetracyanoquinodimethane (TCNQ) as an electron accepting dopant material.
- MTDATA 4,4′,4′′-tris(N-3-methylphenyl-N-phenylamino)triphenylamine
- PS polystyrene
- F 4 -TCNQ tetrafluoro-tetracyanoquinodimethane
- TCNQ tetracyanoquinodimethane
- the OLED is prepared by vapor depositing, onto an ITO substrate with a buffer layer, 20 nm of N,N′-bis(naphthan-2-yl)-N,N′-bis(phenyl)benzidine (NPD, H. W. Sands Corp., Jupiter, Fla.), followed by 30 nm of aluminum tris(8-hydroxyquinolate) (AlQ, H. W. Sands Corp, Jupiter, Fla.) doped with ca. 1 wt. % of green-emitting Coumarin 545T (C545T, Eastman Kodak Co., Rochester, N.Y.), and followed by 20 nm of AlQ.
- the OLED was capped with a cathode composed of ca.
- the NPD layer acts as a hole-transport layer and electron-blocking layer
- the layer of AlQ doped with C545T acts as a light emitting layer
- the layer of AlQ acts as an electron injection and transport layer.
- All organic and cathode layers except the buffer layers were fabricated in a standard vacuum-deposition procedure at a base vacuum of ca. 10 ⁇ 7 to 10 ⁇ 5 torr (about 10 ⁇ 5 to 10 ⁇ 3 Pa) with evaporation rates of 0.05-0.2 nm/s for organic materials, 0.05 nm/s for LiF, and 1.5-2 nm/s for Al.
- Comparative Example 1 polypyrrole (PPY, Aldrich Chemical Co.) was used as a control hole-injecting buffer layer for purposes of comparison of the OLED behavior of the devices deposited onto PPY and onto doped triarylamine-based buffer layers.
- PPY was spun-coat from its water suspension after filtering the suspension through 0.2 ⁇ m Nylon microfilters, followed by annealing under nitrogen gas flow at 110° C. for ca. 15 min.
- OLEDs with buffer layers containing MTDATA, PS, and TCNQ were prepared and their performance evaluated along with that of the control PPY-based OLEDs.
- MTDATA, PS, and TCNQ were purchased from H W Sands Corp. (Jupiter, Fla.), Polysciences Inc. (Eppelheim, Germany), and TCI America (Portland, Oreg.), respectively.
- the buffer layers were spun-coat from their ca. 1.5 wt. % solutions in toluene at the spin-rate of 2000 RPM (about 33 s ⁇ 1 ) to form ca. 90 nm thick films on the ITO coated substrates.
- the device structures are glass-ITO/buffer layer/NPD/AlQ:C545T/AlQ/LiF/Al.
- the buffers layers for the Examples are:
- Example. 1 31 wt. % PS, 62 wt. % MTDATA, and 7 wt. % TCNQ
- Example 2 47 wt. % PS, 46 wt. % MTDATA, and 7 wt. % TCNQ
- Example 3 62 wt. % PS, 31 wt. % MTDATA, and 7 wt. % TCNQ
- High bandgap hole-transporting poly(N-vinylcarbazole) (PVK, Polymer Source Inc., Dorval, Quebec) having relatively high oxidation potential (ca. 1V vs. SCE) and low hole mobility (ca. 10 ⁇ 6 ⁇ 10 ⁇ 5 cm 2 /V*s (about 10 ⁇ 10 ⁇ 10 ⁇ 9 m 2 /V s)) was used as an electroactive binder in the following buffer compositions: a) 60 wt. % PVK and 40 wt. % MTDATA, and b) 56 wt. % PVK, 37 wt. % MTDATA, and 7 wt. % F 4 -TCNQ. These buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s ⁇ 1 ) to form ca. 90 nm thick films on the ITO coated substrates.
- Example 5 60 wt. % PVK and 40 wt. % MTDATA
- Example 6 56 wt. % PVK, 37 wt. % MTDATA, and 7 wt. % F 4 -TCNQ
- Luminance-voltage-current density screening of the OLEDs indicated that high efficiencies can be obtained in the composition including triarylamine-based buffers along with low operational voltages. Doping the PVK:MTDATA blend with F 4 -TCNQ significantly lowered the operational voltage of the OLEDs. Operational lifetime studies on the triarylamine-based compositions, in which the OLEDs were driven at a constant current of ca. 1.8 mA/cm 2 (about 18 A/m 2 ) under inert atmosphere, show that projected operation lifetimes of these OLEDs extend into 10 3 -10 4 hours range at an initial luminance of several hundred Cd/m 2 .
- Buffer Layers Contains Copolymers With Triarylamine Moieties Pendant to a Polyolefin Backbone
- doped triarylamine buffer layers based on copolymers incorporating triarylamine moieties as a functionality pendant to a polyolefin backbone were incorporated into OLEDs.
- a block co-polymer of styrene with diphenylaminostyrene (PS-pDPAS), having approximately 6:1 molar ratio of the monomers was synthesized and screened as a triarylamine-containing polymer.
- the mixture was extracted with ether, and the combined organic layers were dried over MgSO 4 and concentrated under vacuum.
- the crude solid was purified by column chromatography on silica gel using a 50/50 mixture of methylene chloride and hexane to give a yellow solid that was further recrystallized once from hexane (15.37 g, 78%).
- a round-bottom glass reactor was baked out under vacuum at 200° C. for 2 hours, then allowed to cool. The reactor was filled with dry nitrogen. Subsequently, 71.8 g of cyclohexane and 4.4 mL of tetrahydrofuran (THF) were added to the reactor by syringe.
- THF tetrahydrofuran
- the THF was distilled from sodium/benzophenone solution under nitrogen prior to use, in order to scavenge water and oxygen.
- the cyclohexane was dried by passage through activated basic alumina, followed by sparging with nitrogen gas for 30 minutes prior to use. After addition of the solvents, the reaction flask was cooled to 3° C.
- the resulting PS-pDPAS block polymer contained 74.1 mol % styrene and 25.9 mol % p-diphenylaminostyrene, based on 13 C NMR.
- the molecular weight of the block copolymer was 7700 g/mol, based on gel permeation chromatography in THF against polystyrene standards.
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Example 8 93 wt. % PS-pDPAS and 7 wt. % F 4 -TCNQ
- buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s ⁇ 1 ) to form ca. 90 nm thick films on the ITO coated substrates.
- the buffer layers include PEDT (poly(3,4-ethylenedioxythiophene) available as CH8000 from Bayer A G, Leverkusen, Germany), undoped poly ⁇ (9-phenyl-9H-carbazole-3,6-diyl)[N,N′-bis(phenyl-4-yl)-N,N′-bis(4-butylphenyl)benzene-1,4-diamine] ⁇ (Cz-triarylamine), and Cz-triarylamine doped with F 4 -TCNQ.
- PEDT poly(3,4-ethylenedioxythiophene) available as CH8000 from Bayer A G, Leverkusen, Germany
- Cz-triarylamine as a triarylamine-containing co-polymer for hole injecting buffer layers lies in the presence of phenylenediamine linkages, which typically cause lower ionization potential (higher energy of the highest occupied molecular orbital). This provides favorable conditions for increased conductivity due to doping with electron acceptors (e.g. F 4 -TCNQ).
- electron acceptors e.g. F 4 -TCNQ
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Example 10 93 wt. % Cz-triarylamine and 7 wt. % F 4 -TCNQ.
- buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s ⁇ 1 ) to form ca. 90 nm thick films on the ITO coated substrates.
- This Example describes the fabrication of hole-injecting solution-processed buffer layers based on doped triarylamines blended with electroactive polymer binder and blended with color-converting organic dye material in order to tune electroluminescence energy and CIE color coordinates of the OLEDs incorporating such buffer layers.
- the Dye can be prepared according to U.S. Pat. No. 5,639,896, incorporated herein by reference and is available as “Amaplast Blue RFC” supplied by “American Aniline Products”, N.Y., N.Y., a unit of Koppers Co., Pittsburgh, Pa. Each solution was then spun coat onto cleaned ITO substrates at 3000 R.P.M. for 30 s.
- a vapor deposited small-molecule OLED with NPD (20 nm, 0.2 nm/s), AlQ (50 nm, 0.1 nm/s), LiF (0.7 nm, 0.05 nm/s), Al (200 nm, 2 nm/s) was sequentially deposited on top in a standard vacuum deposition procedure at 10-6 torr (about 10-4 Pa) as described in Comparative Example 1 and Examples 1-3.
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Example 11 Solution a) corresponding to 58 wt. % PVK, 38 wt. % MTDATA and 4 wt. % F 4 -TCNQ
- Example 12 Solution b) corresponding to 24 wt. % PVK, 16 wt. % MTDATA, 2 wt. % F 4 -TCNQ, and 58 wt. % Dye
- Example 13 Solution c) corresponding to 18 wt. % PVK, 12 wt. % MTDATA, 1 wt. % F 4 -TCNQ, and 69 wt. % Dye.
- a thermal transfer donor sheet was prepared in the following manner:
- An LTHC solution given in Table II, was coated onto a 0.1 mm thick polyethylene terephthalate (PET) film substrate (M7 from Teijin, Osaka, Japan). Coating was performed using a Yasui Seiki Lab Coater, Model CAG-150, using a microgravure roll with 150 helical cells per inch. The LTHC coating was in-line dried at 80° C. and cured under ultraviolet (UV) radiation.
- PET polyethylene terephthalate
- an interlayer solution given in Table III, was coated onto the cured LTHC layer by a rotogravure coating method using the Yasui Seiki lab coater, Model CAG-150, with a microgravure roll having 180 helical cells per lineal inch. This coating was in-line dried at 60° C. and cured under ultraviolet (UV) radiation.
- UV ultraviolet
- MTDATA (4,4′,4′′-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine) (OSA 3939, H. W. Sands Corp., Jupiter, Fla.) 1.0% (w/w) in toluene was filtered and dispensed through a Whatman PuradiscTM 0.45 ⁇ m Polypropylene (PP) syringe filter.
- PVK Poly(9-vinylcarbazole) (Aldrich Chemical Co., Milwaukee, Wis.) 1.0% (w/w) in toluene was filtered and dispensed through a Whatman PuradiscTM 0.45 ⁇ m Polypropylene (PP) syringe filter.
- F 4 -TCNQ Tetrafluorotetracyanoquinodimethane (Tokyo Kasei Kogyo Co., Tokyo, Japan) 0.25% (w/w) in toluene was filtered and dispensed through a Whatman PuradiscTM 0.45 ⁇ m Polypropylene (PP) syringe filter.
- PP Polypropylene
- MTDATA/F 4 -TCNQ 98/2 w/w% mixture of MTDATA/F 4 -TCNQ.
- MTDATA/PVK 65/35 w/w% mixture of MTDATA/PVK
- MTDATA/PVK/F 4 -TCNO 64/35/1 w/w/w% mixture of MTDATA/PVK/F 4 -TCNQ
- Receptors were formed as follows: ITO(indium tin oxide) glass (Delta Technologies, Stillwater, Minn., less than 100 ⁇ /square, 1.1 mm thick) was processed using photolithography to provide a patterned ITO structure capable of making an electroluminescent device.
- the substrate was ultrasonically cleaned in a hot, 3% solution of Deconex 12NS (Borer Chemie A G, Zuchwil Switzerland). The substrates were then placed in the Plasma Science plasma treater for surface treatment under the following conditions: Time: 2 minutes Power: 500 watt (165 W/cm 2 ) Oxygen Flow: 100 sccm
- Covion Super Yellow Covion PPV polymer PDY 132 “Super Yellow” (75 mg) from Covion Organic Semiconductors GmbH, Frankfurt, Germany was weighed out into an amber vial with a PTFE cap. To this was added 9.925 g of toluene (HPLC grade obtained from Aldrich Chemical, Milwaukee, Wis.). The solution was stirred over night. The solution was filtered through a 5 ⁇ m Millipore Millex syringe filter.
- PP polypropylene
- Transfer layers were formed on the donor sheets using a 33/67 w/w% blend of the solutions of Covion Super Yellow and polystyrene from the previous section. To obtain the blends, the above-described solutions were mixed at the appropriate ratios and the resulting blend solutions were stirred for 20 min at room temperature.
- the transfer layers were disposed on the donor sheets by spinning (Headway Research spincoater) the blend solution at about 2000-2500 rpm for 30 s to yield a film thickness of approximately 100 nm.
- the donor sheets coated with Covion Super Yellow/polystyrene were brought into contact with each of the receptor substrates prepared in an above section.
- the donor sheets were imaged using two single-mode Nd:YAG lasers. Scanning was performed using a system of linear galvanometers, with the combined laser beams focused onto the image plane using an f-theta scan lens as part of a near-telecentric configuration.
- the laser energy density was 0.4 to 0.8 J/cm 2 .
- the laser spot size, measured at the 1/e 2 intensity, was 30 micrometers by 350 micrometers.
- the linear laser spot velocity was adjustable between 10 and 30 meters per second, measured at the image plane.
- the laser spot was dithered perpendicular to the major displacement direction with about a 100 nm amplitude.
- the transfer layers were transferred as lines onto the receptor substrates, and the intended width of the lines was about 100 nm.
- Electroluminescent devices were prepared by depositing calcium/silver cathodes on top of the LEP (Covion Super Yellow/PS) transferred in the above section. Approximately 40 nm of calcium was vapor deposited at a rate of 0.11 nm/s onto the LEP, followed by approximately 400 nm of silver at a rate of 0.5 nm/s. In all cases, diode behavior and yellow light emission was observed.
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
Description
- Organic electroluminescent devices (OELs) include layers of organic materials, at least one of which can conduct a charge. Examples of organic electroluminescent devices include organic light emitting diodes (OLEDs). Specific OEL devices, sometimes referred to as lamps, are desirable for use in electronic media because of their thin profile, low weight, and low driving voltage. OEL devices have potential use in applications such as, for example, lighting applications, backlighting of graphics, pixelated displays, and large emissive graphics.
- OEL devices typically include an organic light emitter layer and optionally one or more charge transport layers, all of which are sandwiched between two electrodes: a cathode and an anode. Charge carriers, electrons and holes, are injected from the cathode and anode, respectively. Electrons are negatively charged atomic particles and holes are vacant electron energy states that behave as though they are positively charged particles. The charge carriers migrate to the emitter layer, where they combine to emit light.
- This basic OEL device structure can be modified to improve or enhance one or more electrical, chemical, or physical properties of the device. Such modification can include the addition or modification of one or more of the basic layers.
- Generally, the present invention relates to organic electroluminescent devices, articles containing the organic electroluminescent devices, and methods of making and using the organic electroluminescent devices and articles.
- One embodiment is an electroluminescent device having multiple layers including, but not limited to, an electrode, an emission layer, and a buffer layer. The emission layer includes a light emitting material. The buffer layer is disposed between and in electrical communication with the electrode and the emission layer and includes a triarylamine hole transport material and an electron acceptor material. The buffer layer optionally includes one or more of a) a polymeric binder, b) a color converting material, and c) light scattering particles.
- Another embodiment is a method of making an electroluminescent device. The method includes forming an electrode, coating a buffer layer from solution over the electrode, and disposing an emission layer over the buffer layer. The electrode, buffer layer, and emission layer are in electrical communication. The emission layer includes a light emitting material. The buffer layer includes a triarylamine hole transport material and an electron acceptor material. Optionally, the buffer layer includes one or more of a) a polymeric binder, b) a color converting material, and c) light scattering particles.
- Yet another embodiment is an electroluminescent device having multiple layers including, but not limited to, an electrode, an emission layer, and a buffer layer. The emission layer includes a light emitting material. The buffer layer is disposed between and in electrical communication with the electrode and the emission layer. The buffer layer includes (a) a polymeric hole transport material having triarylamine moieties and (b) an electron acceptor material. Optionally, the buffer layer includes one or more of a) a color converting material, and b) light scattering particles.
- Another embodiment is a method of making an electroluminescent device. The method includes forming an electrode, coating a buffer layer from solution over the electrode, and disposing an emission layer over the buffer layer. The electrode, buffer layer, and emission layer are in electrical communication. The emission layer includes a light emitting material. The buffer layer includes (a) a polymeric hole transport material having triarylamine moieties and (b) an electron acceptor material. Optionally, the buffer layer includes one or more of a) a color converting material, and b) light scattering particles.
- The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the present invention. The Figures and the detailed description which follow more particularly exemplify these embodiments.
- The invention may be more completely understood in consideration of the following detailed description of various embodiments of the invention in connection with the accompanying drawings, in which:
- FIG. 1 is a schematic side view of an organic electroluminescent display construction;
- FIG. 2 is a schematic side view of a first embodiment of an electroluminescent device, according to the present invention;
- FIG. 3 is a schematic side view of a second embodiment of an electroluminescent device, according to the present invention;
- FIG. 4 is a schematic side view of a third embodiment of an electroluminescent device, according to the present invention; and
- FIG. 5 is a schematic side view of an organic electroluminescent display according to the present invention.
- While the invention is amenable to various modifications and alternative forms, specifics thereof have been shown by way of example in the drawings and will be described in detail. It should be understood, however, that the intention is not to limit the invention to the particular embodiments described. On the contrary, the intention is to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.
- The present invention is believed to be applicable to electroluminescent devices, articles containing the electroluminescent devices, and methods of making and using the electroluminescent devices and articles. In particular, the present invention is directed to organic electroluminescent devices containing a buffer layer with a triarylamine material and an electron acceptor material, articles containing the organic electroluminescent devices, and methods of making and using the organic electroluminescent devices and articles. Pixelated and non-pixelated electroluminescent displays, backlights, and other lighting components are examples of some of the articles that can include organic electroluminescent devices. While the present invention is not so limited, an appreciation of various aspects of the invention will be gained through a discussion of the examples provided below.
- Organic electroluminescent device refers to an electroluminescent device that includes an organic emissive material. The emissive material can include, for example, a small molecule (SM) emitter, a SM doped polymer, a light emitting polymer (LEP), a doped LEP, a blended LEP, or any combination of these materials. This emissive material can be provided alone or in combination with any other organic or inorganic materials, including, for example, binders, color converting materials, and scattering materials, that are functional or non-functional in the organic electroluminescent device.
- R. H. Friend, et al. (“Electroluminescence in Conjugated Polymers” Nature, 397, 1999, 121, incorporated herein by reference) describe one mechanism of electroluminescence as including the “injection of electrons from one electrode and holes from the other, the capture of oppositely charged carriers (so-called recombination), and the radiative decay of the excited electron-hole state (exciton) produced by this recombination process.”
- As an example of electroluminescent device structure, FIG. 1 illustrates an organic
electroluminescent device 100 that includes adevice layer 110 and asubstrate 120. Any other suitable device component can also be included with thedevice 100. Optionally, additional optical elements or other devices suitable for use with electronic displays, devices, or lamps can be provided between thedisplay 100 and aviewer position 140 as indicated by anoptional element 130. -
Substrate 120 can be any substrate suitable for the electroluminescent device application. For example,substrate 120 can include glass, clear plastic, or other suitable material(s) that are substantially transparent to visible light. Examples of suitable plastic substrates include those made of polymers such as polyolefins, polyethersulfones, polycarbonates, polyesters, and polyarylates.Substrate 120 can also be opaque to visible light such as, for example, stainless steel, crystalline silicon, poly-silicon, or the like. Because some materials in electroluminescent devices can be particularly susceptible to damage due to exposure to oxygen or water,substrate 120 preferably provides an adequate environmental barrier or is supplied with one or more layers, coatings, or laminates that provide an adequate environmental barrier. -
Substrate 120 can also include any number of devices or components suitable in electroluminescent devices and displays such as, for example, transistor arrays and other electronic devices; color filters, polarizers, wave plates, diffusers, and other optical devices; insulators, barrier ribs, black matrix, mask works and other such components; and the like. Generally, one or more electrodes is coated, deposited, patterned, or otherwise disposed onsubstrate 120 before forming the remaining layer or layers of the electroluminescent device or devices of thedevice layer 110. When alight transmissive substrate 120 is used and the organic electroluminescent device or devices are bottom emitting, the electrode or electrodes that are disposed between thesubstrate 120 and the emissive material(s) are preferably substantially transparent to light. For example, transparent conductive electrodes such as indium tin oxide (ITO) or any of a number of other semi-transparent or transparent conductive oxides or nitrides, or semi-transparent or transparent metals can be used. -
Element 130 can be any element or combination of elements suitable for use withelectroluminescent device 100. For example,element 130 can be an LCD module whendevice 100 is a backlight. One or more polarizers or other elements can be provided between the LCD module and thebacklight device 100, for instance an absorbing or reflective clean-up polarizer. Alternatively, whendevice 100 is itself an information display,element 130 can include one or more of polarizers, wave plates, touch panels, antireflective coatings, anti-smudge coatings, projection screens, brightness enhancement films, scattering films, light extraction films, refractive index gradient films, or other optical components, coatings, user interface devices, or the like. - In some embodiments like the one shown,
device layer 110 includes one or more electroluminescent devices that emit light through the substrate toward aviewer position 140. Theviewer position 140 is used generically to indicate an intended destination for the emitted light whether it be an actual human observer, a screen, an optical component, an electronic device, or the like. In other embodiments (not shown),device layer 110 is positioned betweensubstrate 120 and theviewer position 140. The device configuration shown in FIG. 1 (termed “bottom emitting”) may be used when, for example,substrate 120 is transmissive to light emitted bydevice layer 110 and when a transparent conductive electrode is disposed in the device between the emissive layer of the device and the substrate. The inverted configuration (termed “top emitting”) may be used when, for example,substrate 120 does or does not transmit the light emitted by the device layer and the electrode disposed between the substrate and the light emitting layer of the device does not transmit the light emitted by the device. In yet other embodiments, the device may emit from both the top and bottom, in which case both conductive electrodes are preferably transparent or semi-transparent. -
Device layer 110 can include one or more electroluminescent devices arranged in any suitable manner. For example, in lamp applications (e.g., backlights for liquid crystal display (LCD) modules),device layer 110 can constitute a single electroluminescent device that spans an entire intended backlight area. Alternatively, in other lamp applications,device layer 110 can constitute a plurality of closely spaced electroluminescent devices that can be contemporaneously activated. For example, relatively small and closely spaced red, green, and blue light emitters can be patterned between common electrodes so thatdevice layer 110 appears to emit white light when the emitters are activated. Other arrangements for backlight applications are also contemplated. - In direct view or other display applications, it may be desirable for
device layer 110 to include a plurality of independently addressable electroluminescent devices that emit the same or different colors. Each device can represent a separate pixel or a separate sub-pixel of a pixilated display (e.g., high resolution display), a separate segment or sub-segment of a segmented display (e.g., low information content display), or a separate icon, portion of an icon, or lamp for an icon (e.g., indicator applications). - In at least some instances, an electroluminescent device includes a thin layer, or layers, of one or more suitable materials sandwiched between a cathode and an anode. When activated, electrons are injected into the layer(s) from the cathode and holes are injected into the layer(s) from the anode. As the injected charges migrate towards the oppositely charged electrodes, the charges can recombine to form electron-hole pairs which are typically referred to as excitons. The region of the device in which the exitons are generally formed can be referred to as the recombination zone. These excitons, or excited state species, can emit energy in the form of light as they decay back to a ground state.
- Other layers can also be present in electroluminescent devices such as hole transport layers, electron transport layers, hole injection layers, electron injection layers, hole blocking layers, electron blocking layers, buffer layers, and the like. In addition, photoluminescent materials can be present in the electroluminescent or other layers in electroluminescent devices, for example, to convert the color of light emitted by the electroluminescent material to another color. These and other such layers and materials can be used to alter or tune the electronic properties and behavior of the layered electroluminescent device, for example, to achieve one or more features such as a desired current/voltage response, a desired device efficiency, a desired color, a desired brightness, a desired device lifetime, or a desired combination of these features.
- FIGS. 2, 3, and4 illustrate examples of different electroluminescent device configurations where like elements are provided the same reference numeral. Each configuration includes a
substrate 250, ananode 252, abuffer layer 254, anemission layer 256, and acathode 258. The configurations of FIGS. 3 and 4 also include ahole transport layer 260 between thebuffer layer 254 and theemission layer 256. Alternatively or additionally, a hole transport layer (not shown) may be positioned between the anode and the buffer layer. The configuration of FIG. 4 includes an electron transport orelectron injection layer 262. Thesubstrate 250 can be made of any of the materials discussed with respect tosubstrate 120 of FIG. 1. Optionally, a hole injection layer, electron injection layer, or both can also be added or thehole transport layer 260 could be removed. In some embodiments, thebuffer layer 254 acts, at least in part, as a hole injection layer or hole transport layer. In addition, any of the layers illustrated in FIGS. 2, 3, and 4 can be formed using a single layer of material or multiple layers of the same or different materials. The material for each layer can be a single compound or a combination of two or more different compounds. - The
anode 252 andcathode 258 are typically formed using conducting materials such as metals, alloys, metallic compounds, metal oxides, conductive ceramics, conductive dispersions, and conductive polymers, including, for example, gold, silver, copper, platinum, palladium, aluminum, calcium, barium, magnesium, titanium, titanium nitride, indium oxide, indium tin oxide (ITO), vanadium oxide, zinc tin oxide, fluorine tin oxide (FTO), polyaniline, polypyrrole, polythiophene, and combinations or alloys of these materials. Theanode 252 and thecathode 258 can be single layers of conducting materials or they can include multiple layers. For example, an anode or a cathode can include a layer of aluminum and a layer of gold, a layer of calcium and a layer of aluminum, a layer of lithium fluoride and a layer of aluminum, a layer of magnesium and silver, a layer of magnesium and silver followed by another layer of silver, or a metal layer and a conductive organic layer. - The
emission layer 256 includes one or more light emitting materials, such as a small molecule (SM) emitter, a SM doped polymer, a light emitting polymer (LEP), a doped LEP, a blended LEP, another organic emissive material, or any combination of these materials. Examples of classes of suitable LEP materials include poly(phenylenevinylene)s (PPVs), poly-para-phenylenes (PPPs), polyfluorenes (PFs), other LEP materials now known or later developed, and co-polymers or blends thereof. Suitable LEPs can also be molecularly doped, dispersed with luminescent dyes or other photoluminescent (PL) materials, blended with active or non-active materials, dispersed with active or non-active materials, and the like. Examples of suitable LEP materials are described in, for example, Kraft, et al., Angew. Chem. Int. Ed., 37, 402-428 (1998); U.S. Pat. Nos. 5,621,131; 5,708,130; 5,728,801; 5,840,217; 5,869,350; 5,900,327; 5,929,194; 6,132,641; and 6,169,163; and PCT Patent Application Publication No. 99/40655, all of which are incorporated herein by reference. - SM materials are generally non-polymer organic or organometallic molecular materials that can be used in organic electroluminescent displays and devices as emitter materials, charge transport materials, as dopants in emitter layers (e.g., to control the emitted color) or charge transport layers, and the like. Commonly used SM materials include metal chelate compounds, for example, tris(8-hydroxyquinoline) aluminum (AlQ) and derivatives thereof, and organic compounds, for example, N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD). Other SM materials are disclosed in, for example, C. H. Chen, et al.,Macromol. Symp. 125, 1 (1997), Japanese Laid Open Patent Application 2000-195673, U.S. Pat. Nos. 6,030,715, 6,150,043, and 6,242,115 and, PCT Patent Applications Publication Nos. WO 00/18851 (divalent lanthanide metal complexes), WO 00/70655 (cyclometallated iridium compounds and others), and WO 98/55561, all of which are incorporated herein by reference.
- The optional
hole transport layer 260 facilitates the injection of holes from the anode into the device and their migration towards the recombination zone. Thehole transport layer 260 can further act as a barrier for the passage of electrons to theanode 252. Thehole transport layer 260 can include, for example, a diamine derivative, such as N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (also known as TPD) or N,N′-bis(3-naphthalen-2-yl)-N,N′-bis(phenyl)benzidine (NPD), or a triarylamine derivative, such as, 4,4′,4″-Tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA), 4,4′,4″-tri(N-phenothiazinyl) triphenylamine (TPTTA), 4,4′,4″-tri(N-phenoxazinyl) triphenylamine (TPOTA). Other examples include copper phthalocyanine (CuPC); 1,3,5-Tris(4-diphenylaminophenyl)benzenes (TDAPBs); poly(vinyl carbazole); and other compounds such as those described in Shirota, J. Mater. Chem., 10, 1 (2000), H. Fujikawa, et al., Synthetic Metals, 91, 161 (1997), and J. V. Grazulevicius, P. Strohriegl, “Charge-Transporting Polymers and Molecular Glasses”, Handbook of Advanced Electronic and Photonic Materials and Devices, H. S. Nalwa (ed.), 10, 233-274 (2001), all of which are incorporated herein by reference. - The optional
electron transport layer 262 facilitates the injection of electrons and their migration towards the recombination zone. Theelectron transport layer 262 can further act as a barrier for the passage of holes to thecathode 258, if desired. As an example, theelectron transport layer 262 can be formed using the organometallic compound tris(8-hydroxyquinolato) aluminum (AlQ). Other examples of electron transport materials include 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 1,3-bis[5-(4-(1,1-dimethylethyl)phenyl)-1,3,4-oxadiazol-2-yl]benzene, 2-(biphenyl-4-yl)-5-(4-(1,1-dimethylethyl)phenyl)-1,3,4-oxadiazole (tBuPBD) and other compounds described in Shirota, J. Mater. Chem., 10, 1 (2000), C. H. Chen, et al., Macromol. Symp. 125, 1 (1997), and J. V. Grazulevicius, P. Strohriegl, “Charge-Transporting Polymers and Molecular Glasses”, Handbook of Advanced Electronic and Photonic Materials and Devices, H. S. Nalwa (ed.),10, 233 (2001), all of which are incorporated herein by reference. - The
buffer layer 254 facilitates the injection of holes from the anode into thehole transport layer 260 oremission layer 256. The buffer layer may also assist in planarization of previously formed layers, such as the anode. This planarization may also assist in reducing or eliminating short circuits due to non-uniformity in the anode. In addition, the buffer layer may facilitate formation of other layers on the buffer layer, including the forming of other layers by thermal transfer onto the buffer layer. -
- where Ar1, Ar2, and Ar3 are substituted or unsubstituted aryl or arylene functional groups and where, optionally, the triarylamine moiety(ies) is/are coupled to other portions of the compound through one or more of the arylene functional groups, if present. Examples of suitable materials include triphenylamine and biphenyldiamines such as, for example, N,N′-bis(naphthalene-2-yl)-N,N′-bis(phenyl)benzidine (NPD), N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD), and 4,4′-bis(carbazol-9-yl)biphenyl (CPB).
-
-
- where R2 is alkyl or aryl and each R3, R4, and R5 is independently H, alkyl, aryl, alkoxy, aryloxy, halo, alkylthio, arylthio, or —NRaRb, where Ra and Rb are aryl or alkyl. With respect to Formula 8, in some embodiments, all R3 are the same, all R4 are the same, all R5 are the same, or any combination thereof (e.g., all R3 and R4 are the same). Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted including, for example, fluorinated and perfluorinated alkyls.
-
-
- where each R2 is independently alkyl or aryl and each R3 and R4 is independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NRaRb, where Ra and Rb are aryl or alkyl. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted. In some embodiments, one of the following conditions applies: all of the R3 and R4 substituents are the same; all of the R3 substituents are the same; all of the R4 substituents are the same; or all of the R3 substituents and all of the R4 substituents are the same, but R3 and R4 are different.
- Specific examples of suitable compounds of this type include 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA) (Formula 13), 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA) (Formula 14), 4,4′,4″-tris(carbozol-9-yl)triphenylamine (TCTA) (Formula 15), 4,4′,4″-tris(N-naphthyl-N-phenylamino)triphenylamine (2-TNATA) (Formula 16):
-
- As an alternative to small molecule triarylamine materials, polymeric materials with triarylamine moieties can be used. The triarylamine moieties can be in the backbone of the polymeric material, can be pendent groups extending from the backbone of the polymeric material, or both. Polymers with triarylamine moieties in the backbone include, for example, the polymers of Formulas 18, 19, 20, and 21:
- where R3 and R4 are independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NRaRb, where Ra and Rb are aryl or alkyl, Ar9 is aryl or arylene, CM is one or more comonomers, n is an integer of three or greater and preferably 10 or greater, and m is an integer of zero or greater. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted. Suitable comonomers, CM, include, for example, another triarylamine-containing monomer such as those illustrated in Formulas 18-21 or 33-34 below, arylene (including substituted or unsubstituted para- or meta-phenylene), substituted or unsubstituted styrene comonomers, derivatized carbazole comonomers (such as N-alkyl carbazole or N-aryl carbazole, for example, the comomoners as illustrated in Formulas 29 and 32), ether- and polyether-linked comonomers, carbonate comonomers, urethane-linked comonomers, thioether-linked comonomers, ester-linked comonomers, and imide- and amide-linked comonomers. Examples of such comonomers include, but are not limited to, —O—(CnH2nO)— and —Ar10—O—(CnH2nO)—A11— where Ar10 and Ar11 are arylene.
-
- Other examples of cross-linkable moieties are described in, for example, PCT Patent Application Publication No. WO 97/33193, incorporated herein by reference. In some embodiments, the polymers containing such cross-linkable moieties are selected to crosslink under relatively mild photochemical or thermal conditions. For example, thermal crosslinking may occur at 100 to 150° C. Alternatively, UV-visible radiation in the range of 300 to 700 nm might be used to crosslink the polymers.
- Typically the comonomer is copolymerized with the triarylamine-containing monomer unit. However, in some instances, the comonomer can be coupled to the triarylamine-containing monomer unit prior to polymerization. Such a polymer might not be considered a copolymer, but rather a homopolymer with the coupled triarylamine-containing unit/comonomer unit as the basic monomer unit of the polymer. Examples of such polymers are illustrated by Formulas 24-27.
-
- In Formulas 29-32, the comonomer unit is coupled to the triarylamine moiety-containing monomer unit in such a way that the two monomer units alternate in the polymer.
-
- where R3, R4, and R5 are independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NRaRb, where Ra and Rb are aryl or alkyl, CM is one or more comonomers, n is an integer of three or greater and preferably 10 or greater, and m is an integer of zero or greater. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted. Suitable comonomers, CM, include, for example, another triarylamine-containing monomer containing one or more chain polymerizable moieties, arylenes (including substituted or unsubstituted para- or meta-phenylene) with one or more chain polymerizable moieties, derivatized carbazole comonomers (such as N-vinyl carbazole), carbonate comonomers, urethane-linked comonomers, thioether-linked comonomers, ester-linked comonomers, imide- and amide-linked comonomers, substituted or unsubstituted styrene comonomers, (meth)acrylate comonomers of, for example, C1-C12 alcohols, diene comonomers such as, for example, butadiene, isoprene and 1,3 cyclohexadiene, and other chain-polymerizable comonomers.
- Typically the comonomer is copolymerized with the triarylamine-containing monomer unit. However, in some instances, the comonomer can be coupled to the triarylamine-containing monomer unit prior to polymerization. Such a polymer might not be considered a copolymer, but rather a homopolymer with the coupled triarylamine-containing unit/comonomer unit as the basic monomer unit of the polymer. One example is illustrated as Formula 35.
- It will be understood that the pendent groups can also extend from backbone moieties other than the ethylene moieties illustrated in Formulas 33 and 34. Examples of other backbone units from which the triarylamine pendent groups can extend include, for example, alkylene (such as propylene, butylenes, isoprene, or 1,3-cyclohexadiene), silane, arylenes (including substituted or unsubstituted para- or meta-phenylene), derivatized carbazole monomers (as illustrated in Formulas 29 and 32), carbonate monomers, urethane-linked monomers, thioethers-linked monomers, ester-linked monomers, imide- and amide-linked monomers, substituted and unsubstituted styrene monomers, and (meth)acrylate monomers. The triarylamine may not be directly attached to the backbone, but may be separated from the backbone by a spacer group such as, for example, an alkylene group (e.g., methylene or ethylene), alkenylene (e.g., —(CH═CH)n—, n=1-6), alkynylene (e.g., —(C≡C)n—, n=1-6), arylene, an alkyl ether (e.g., —CH2—O—) group, or any combination of these groups.
-
- where each R3, R4, R5, R6, and R7 is independently H, alkyl, aryl, alkoxy, aryloxy, arylthio, alkylthio, halo, or —NRaRb, where Ra and Rb are aryl or alkyl. Each aryl or alkyl portion of any of these substituents can be substituted or unsubstituted. In some embodiments, one or more of the following conditions applies: all of the R3, R4, and R5 substituents are the same; all of the R3 substituents are the same; all of the R4 substituents are the same; all of the R5 substituents are the same; all of the R7 substituents are the same; or all of the R3 substituents and all of the R4 substituents are the same, but R3 and R4 are different. For example, R3, R5, R6, and R7 can be H and R4 can be methyl in any of Formulas 36-38.
- Unless otherwise indicated, the term “alkyl” includes both straight-chained, branched, and cyclic alkyl groups and includes both unsubstituted and substituted alkyl groups. Unless otherwise indicated, the alkyl groups are typically C1-C20. Examples of “alkyl” as used herein include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, isobutyl, and isopropyl, and the like.
- Unless otherwise indicated, the term “aryl” refers to monovalent unsaturated aromatic carbocyclic radicals having one to fifteen rings, such as phenyl or bipheynyl, or multiple fused rings, such as naphthyl or anthryl, or combinations thereof. Examples of aryl as used herein include, but are not limited to, phenyl, 2-naphthyl, 1-naphthyl, biphenyl, 2-hydroxyphenyl, 2-aminophenyl, 2-methoxyphenyl and the like.
- Unless otherwise indicated, the term “arylene” refers to divalent unsaturated aromatic carbocyclic radicals having one to fifteen rings, such as phenylene, or multiple fused rings, such as fluorene, naphthylene or anthrylene, or combinations thereof. Examples of “arylene” as used herein include, but are not limited to, benzene-1,2-diyl, benzene-1,3-diyl, benzene-1,4-diyl, naphthalene-1,8-diyl, anthracene-1,4-diyl, fluorene, phenylenevinylene, phenylenedivinylene, and the like.
- Unless otherwise indicated, the term “alkoxy” refers to the functional group —OR where R is a substituted or unsubstituted alkyl group. Unless otherwise indicated, the alkyl group is typically C1-C20. Examples of “alkoxy” as used herein include, but are not limited to, methoxy, ethoxy, n-propoxy, and 1-methylethoxy, and the like.
- Unless otherwise indicated, the term “aryloxy” refers to the functional group —OAr where Ar is a substituted or unsubstituted aryl group. Examples of “aryloxy” as used herein include, but are not limited to, phenyloxy, naphthyloxy, and the like.
- Suitable substituents for substituted alkyl, aryl, and arylene groups include, but are not limited to, alkyl, alkylene, aryl, arylene, heteroaryl, heteroarylene, alkenyl, alkenylene, —NRR′, F, Cl, Br, I, —OR, —SR, cyano, nitro, —COOH, and —COO-alkyl where R and R′ are independently hydrogen, alkyl, or aryl.
- Unless otherwise indicated, the term “halo” includes fluoro, chloro, bromo, and iodo.
- Unless otherwise indicated, the term “polymer” includes homopolymers and copolymers including block copolymers and random copolymers.
- In addition to the triarylamine material, the buffer layer also includes an electron acceptor material to improve electron transport. Preferably, such compounds have relatively high electron affinity and relatively low energy of the lowest unoccupied molecular orbital (LUMO). Suitable electron acceptor materials include electron deficient compounds such as, for example, tetracyanoquinodimethane and derivatives, thiopyranylidines, polynitrofluorenones, tetracyanoethylene (TCNE), chloranil, and other compounds commonly used as electron acceptors in charge transfer materials and electrophotography. Specific examples of electron acceptor materials include tetracyanoquinodimethane (TCNQ) (Formula 39), tetrafluoro-tetracyanoquinodimethane (F4-TCNQ) (Formula 40), tetracyanoethylene, chloranil, 2-(4-(1-methylethyl)phenyl-6-phenyl-4H-thiopyran-4-ylidene)-propanedinitrile-1,1-dioxyide (PTYPD) (Formula 41), and 2,4,7-trinitrofluorenone (Formula 42).
- Preferably, the electron acceptor material is soluble in one or more organic solvents, more preferably, one or more organic solvents in which the triarylamine material is also soluble. Typically, the electron donor material is present in the buffer layer in the range of 0.5 to 20 wt. % of the triarylamine material. In some embodiments, the electron donor material is present in the buffer layer in the range of 1 to 5 wt. % of the triarylamine material.
- The buffer layer optionally includes a polymeric binder. The polymeric binder can include inert or electroactive polymers or combinations thereof. Suitable polymers for the polymeric binder include, for example, polystyrene, poly(N-vinyl carbazole), polyfluorenes, poly(para-phenylenes), poly(phenylenevinylenes), polycarbonates, polyimides, polyolefins, polyacrylates, polymethacrylates (for example, poly(methylmethacrylate)), polyethers, polysulfones, polyether ketones, and copolymers or mixtures thereof. If the triarylamine material includes a triarylamine-containing polymer, that polymer can act as or in cooperation with a polymeric binder, if desired. If used, the polymeric binder is typically provided in the range of 20 to 150 wt. %, preferably 70 to 120 wt. %, of the triarylamine material.
- In some embodiments, the polymeric binder can be photochemically or thermally crosslinked with itself or with other components in the buffer layer. Accordingly, a thermochemical or photochemical crosslinking agent, such as, for example, 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone, can optionally be included in the buffer layer. Crosslinking can be desirable for one or more purposes, such as decreasing the migration of buffer layer components out of the buffer layer, decreasing the migration of other materials into the buffer layer, increasing thermal stability, increasing mechanical stability, increasing morphological stability, increasing buffer layer stability, and increasing layer integrity, particularly during further solution processing. Crosslinking the buffer layer can also facilitate manufacture of a device by providing a buffer layer upon which other layers can be solution coated or cast with substantially less concern about dissolving the buffer layer.
- The buffer layer can optionally include a color converting material. This material can be a luminescent or non-luminescent organic, organometallic, or inorganic compound or combinations thereof. The color converting material changes the color of electroluminescence from an emitting layer by selective absorption of light or by absorption of light and re-emission of the light in a different spectral range. Suitable materials include, for example, dyes, pigments, and nanoparticles. Examples of suitable non-luminescent and luminescent dyes include: azo dyes (e.g. C.I. Direct Green 26 and others), anthraquinone dyes (e.g. C.I. Reactive Blue 4 and others), indigoid dyes (e.g. Tyrian Purple and others), triphenylmethane-based dyes (e.g. Eosin and others), coumarin dyes (e.g. Coumarin 6 and others), metal porphyrins (e.g. platinum [II] octaethylporphyrin and others), cyclometalated transition metal complexes (e.g. iridium tris(2-phenylpyridine) and others), and other dyes including those discussed in H. Zollinger, Color Chemistry, 1991, VCH Publishers: New York, andThe Chemistry and Application of Dyes, Ed. By D. R. Waring and G. Halls, 1990, Plenum Press: New York, both of which are incorporated herein by reference. Examples of nanoparticles suitable for color conversion can be found in M. Bruchez et al., Science 281, 2013 (1998), incorporated herein by reference. The color converting material can be polymeric with color converting moieties in the backbone, on pendant chains, or both. The color converting material, if used, is typically included in the buffer layer in an amount in the range of 0.1 to 100 wt. %, preferably 0.1 to 10 wt. %, of the triarylamine material.
- The buffer layer can also optionally include scattering material, such as small particles, nanocrystals, or clusters. Examples of suitable materials include clays, oxides, metals, and glasses. Specific examples of suitable materials include titania, alumina and silica powders having a mean particle size of approximately 0.05 to 0.2 microns, and added to the buffer layer composition in a concentration of from 0.1 to 20% by weight, and preferably from about 1-5% by weight.
- The
buffer layer 254 is formed by solution coating the material of the buffer layer onto thesubstrate 250. After formation of thebuffer layer 254, additional layers, such as thehole transport layer 260 oremission layer 256, can be formed on the buffer layer by a variety of techniques including, for example, solution coating, physical or chemical vapor deposition, and thermal transfer, including light-induced thermal transfer as described below. - An organic solvent is used to make the solution for the buffer layer. Examples of suitable organic solvents include carbon tetrachloride, toluene, chloroform, 1,2-dichloroethane, 1,2-dichlorobenzene, tetrahydrofuran, pyridine, and the like. The remaining materials of the buffer layer are typically dispersible or, preferably, soluble in the organic solvent.
- In some conventional device formation methods, layers are formed using solutions of components in water. A drawback of these methods is that some of the device materials are degraded in the presence of water or irreversible physical changes may occur leading to device degradation. Thus, if a layer is formed using a water solution, the water generally must be completely removed. On the other hand according to the invention, organic solvents can be chosen that are easier to remove or do not degrade materials in the device or both.
- In other conventional device formation methods, the materials of a layer are disposed by vapor deposition. A number of materials are difficult to accurately and consistently deposit by vapor deposition methods. Included in these materials are a variety of polymers and ionic compounds. Thus, it can be difficult to deposit materials such as a polymeric binder and cross-linking agent using vapor deposition techniques. In addition, the consistency and uniformity of a vapor deposited composition becomes increasingly difficult when the composition contains multiple components. On the other hand according to the invention, forming a buffer layer by solution coating can facilitate the use of materials such as polymeric binders, polymeric triarylamine materials, crosslinking agents, dyes, pigments, scattering particles, and so on. In addition, the coating technique permits the use of multi-component systems when all of the components are soluble or dispersible in the solvent.
- As an alternative to solution coating the buffer layer material directly onto the substrate or depositing the buffer layer material using ink jet techniques, the buffer layer material can be coated onto a donor sheet and then transferred by techniques such as thermal transfer to the substrate. This can be particularly useful for patterning the buffer layer onto the substrate. For example, the buffer layer material can be selectively transferred from the donor sheet to the substrate according to a pattern by selective application of, for example, light or heat to the donor sheet. This can be useful, for example, to pattern individual buffer layers with a different color converting materials (or lack of color converting material) onto the substrate. Thus, a full-color display could be formed using, for example, three different buffer layers with three different color converting materials (or two different color converting materials and the third buffer layer lacking a color converting material). Other methods of selectively patterning color converting materials in buffer layer(s) include, for example, thermal diffusion of the color converting material, inkjet transfer of the buffer material with (or without) color converting materials onto the substrate, and selective photobleaching.
- Suitable thermal transfer methods for transferring a buffer layer or other device layers to the substrate or onto a previously-formed buffer layer include, for example, thermal head transfer methods and light-induced thermal transfer methods. The presence of the buffer layer on the substrate can, at least in some instances, facilitate the transfer of other layers to the substrate by these methods. Materials, layers, or other structures can be selectively transferred from the transfer layer of a donor sheet to a receptor substrate by placing the transfer layer of the donor element adjacent to the receptor and selectively heating the donor element. For example, the donor element can be selectively heated by irradiating the donor element with imaging radiation that can be absorbed by light-to-heat converter material disposed in the donor, often in a separate light-to-heat conversion (LTHC) layer, and converted into heat. Examples of such methods, donor elements and receptors, as well as articles and devices that can be formed using thermal transfer, can be found in U.S. Pat. Nos. 5,521,035, 5,691,098, 5,693,446, 5,695,907, 5,710,097, 5,725,989, 5,747,217, 5,766,827, 5,863,860, 5,897,727, 5,976,698, 5,981,136, 5,998,085, 6,057,067, 6,099,994, 6,114,088, 6,140,009, 6,190,826, 6,194,119, 6,221,543, 6,214,520, 6,221,553, 6,228,543, 6,228,555, 6,242,152, 6,270,934, and 6,270,944 and PCT Patent Applications Publication Nos. WO 00/69649 and WO 01/39986 and U.S. patent application Ser. Nos. 09/662,845, 09/662,980, 09/844,100, and 09/931,598, all of which are incorporated herein by reference. The donor can be exposed to imaging radiation through the donor substrate, through the receptor, or both. The radiation can include one or more wavelengths, including visible light, infrared radiation, or ultraviolet radiation, for example from a laser, lamp, or other radiation source.
- Other selective heating methods can also be employed, such as using a thermal print head or using a thermal hot stamp (e.g., a patterned thermal hot stamp such as a heated silicone stamp that has a relief pattern that can be used to selectively heat a donor). Thermal print heads or other heating elements may be particularly suited for making lower resolution patterns of material or for patterning elements whose placement need not be precisely controlled.
- Material from the transfer layer can be selectively transferred to a receptor in this manner to imagewise form patterns of the transferred material on the receptor. In many instances, thermal transfer using light from, for example, a lamp or laser, to patternwise expose the donor can be advantageous because of the accuracy and precision that can often be achieved. The size and shape of the transferred pattern (e.g., a line, circle, square, or other shape) can be controlled by, for example, selecting the size of the light beam, the exposure pattern of the light beam, the duration of directed beam contact with the donor sheet, or the materials of the donor sheet. The transferred pattern can also be controlled by irradiating the donor element through a mask.
- Transfer layers can also be transferred from donor sheets without selectively transferring the transfer layer. For example, a transfer layer can be formed on a donor substrate that, in essence, acts as a temporary liner that can be released after the transfer layer is contacted to a receptor substrate, typically with the application of heat or pressure. Such a method, referred to as lamination transfer, can be used to transfer the entire transfer layer, or a large portion thereof, to the receptor.
- A donor sheet for light-induced thermal transfer can include, for example, a donor substrate, an optional underlayer, an optional light-to-heat conversion (LTHC) layer, an optional interlayer, and a transfer layer. The donor substrate can be a polymer film or any other suitable, preferably transparent, substrate. The donor substrate is also typically selected from materials that remain stable despite heating of one or more layers of the donor. However, the inclusion of an underlayer between the substrate and an LTHC layer can be used to insulate the substrate from heat generated in the LTHC layer during imaging.
- The underlayer can include materials that impart desired mechanical or thermal properties to the donor element. For example, the underlayer can include materials that exhibit a low value for the mathematical product of specific heat and density or low thermal conductivity relative to the donor substrate. Such an underlayer may be used to increase heat flow to the transfer layer, for example to improve the imaging sensitivity of the donor. The underlayer can also include materials for their mechanical properties or for adhesion between the substrate and the LTHC.
- An LTHC layer can be included in donor sheets of the present invention to couple irradiation energy into the donor sheet. The LTHC layer preferably includes a radiation absorber that absorbs incident radiation (e.g., laser light) and converts at least a portion of the incident radiation into heat to enable transfer of the transfer layer from the donor sheet to the receptor.
- An optional interlayer can be disposed between the LTHC layer and transfer layer. The interlayer can be used, for example, to minimize damage and contamination of the transferred portion of the transfer layer and may also reduce distortion in the transferred portion of the transfer layer. The interlayer can also influence the adhesion of the transfer layer to the rest of the donor sheet. Typically, the interlayer has high thermal resistance. Preferably, the interlayer does not distort or chemically decompose under the imaging conditions, particularly to an extent that renders the transferred image non-functional. The interlayer typically remains in contact with the LTHC layer during the transfer process and is not substantially transferred with the transfer layer.
- The interlayer can provide a number of benefits, if desired. The interlayer can be a barrier against the transfer of material from the light-to-heat conversion layer. It can also modulate the temperature attained in the transfer layer so that thermally unstable materials can be transferred. For example, the interlayer can act as a thermal diffuser to control the temperature at the interface between the interlayer and the transfer layer relative to the temperature attained in the LTHC layer. This can improve the quality (i.e., surface roughness, edge roughness, etc.) of the transferred layer. The presence of an interlayer can also result in improved plastic memory in the transferred material.
- The thermal transfer layer includes the buffer material to form the buffer layer, if desired, or appropriate materials to form other layers depending on the desired thermal transfer. For example, other layers of the device, such as the hole transport layer or the emission layer, can be transferred onto the substrate or onto the buffer layer or other layers disposed on the substrate by these methods. Such transfer can be sequential using multiple donor sheets or, in some embodiments, multiple layers can be transferred using a single donor sheet with the transfer layer having individual sublayers.
- The present invention contemplates light emitting OEL displays and devices. In one embodiment, OEL displays can be made that emit light and that have adjacent devices that can emit light having different color. For example, FIG. 5 shows an
OEL display 300 that includes a plurality ofOEL devices 310 disposed on asubstrate 320.Adjacent devices 310 can be made to emit different colors of light. - The separation shown between
devices 310 is for illustrative purposes only. Adjacent devices may be separated, in contact, overlapping, etc., or different combinations of these in more than one direction on the display substrate. For example, a pattern of parallel striped transparent conductive anodes can be formed on the substrate followed by a striped pattern of a hole transport material and a striped repeating pattern of red, green, and blue light emitting LEP layers, followed by a striped pattern of cathodes, the cathode stripes oriented perpendicular to the anode stripes. Such a construction may be suitable for forming passive matrix displays. In other embodiments, transparent conductive anode pads can be provided in a two-dimensional pattern on the substrate and associated with addressing electronics such as one or more transistors, capacitors, etc., such as are suitable for making active matrix displays. Other layers, including the light emitting layer(s) can then be coated or deposited as a single layer or can be patterned (e.g., parallel stripes, two-dimensional pattern commensurate with the anodes, etc.) over the anodes or electronic devices. Any other suitable construction is also contemplated by the present invention. - In one embodiment,
display 300 can be a multiple color display. As such, it may be desirable to position optional polarizer 330 between the light emitting devices and a viewer, for example to enhance the contrast of the display. In exemplary embodiments, each of thedevices 310 emits light. There are many displays and devices constructions covered by the general construction illustrated in FIG. 3. Some of those constructions are discussed as follows. - OEL backlights can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like. Applications include white or single color large area single pixel lamps, for example where an emissive material is provided by thermal stamp transfer, lamination transfer, resistive head thermal printing, or the like; white or single color large area single electrode pair lamps that have a large number of closely spaced emissive layers patterned by laser induced thermal transfer; and tunable color multiple electrode large area lamps.
- Low resolution OEL displays can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like. Applications include graphic indicator lamps (e.g., icons); segmented alphanumeric displays (e.g., appliance time indicators); small monochrome passive or active matrix displays; small monochrome passive or active matrix displays plus graphic indicator lamps as part of an integrated display (e.g., cell phone displays); large area pixel display tiles (e.g., a plurality of modules, or tiles, each having a relatively small number of pixels), such as may be suitable for outdoor display used; and security display applications.
- High resolution OEL displays can include emissive layers. Constructions can include bare or circuitized substrates, anodes, cathodes, hole transport layers, electron transport layers, hole injection layers, electron injection layers, emissive layers, color changing layers, and other layers and materials suitable in OEL devices. Constructions can also include polarizers, diffusers, light guides, lenses, light control films, brightness enhancement films, and the like. Applications include active or passive matrix multicolor or full color displays; active or passive matrix multicolor or full color displays plus segmented or graphic indicator lamps (e.g., laser induced transfer of high resolution devices plus thermal hot stamp of icons on the same substrate); and security display applications.
- All chemicals are available from Aldrich Chemical Co., Milwaukee, Wis., unless otherwise indicated.
- Preparation of ITO Substrates
- For Examples 1-13, ITO substrates were prepared as follows: ITO (indium tin oxide) glass substrates (Applied Films Corporation, CO; ca. 25 Ω/sq.) were rinsed in acetone (Aldrich Chemical Company), dried with nitrogen, and rubbed with TX1010 Vectra Sealed-Border Wipers (ITW Texwipe, Upper Saddle River, N.J.) soaked in methanol (Aldrich Chemical Company, Milwaukee, Wis.), after which they were subjected to oxygen plasma treatment for four minutes at 200 mT (about 27 Pa) base oxygen pressure and output power of 50 W in Technics Micro Reactive Ion Etcher, Series 80 (K&M Company, CA). The OLED's described below were generally 1 to 1.5 cm2 in size.
- This Example describes the formation of OLEDs having a solution-processed hole-injecting buffer layer incorporating 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA) as a triarylamine material, polystyrene (PS) as an electrically inert polymer binder, and tetrafluoro-tetracyanoquinodimethane (F4-TCNQ) or tetracyanoquinodimethane (TCNQ) as an electron accepting dopant material.
- The OLED is prepared by vapor depositing, onto an ITO substrate with a buffer layer, 20 nm of N,N′-bis(naphthan-2-yl)-N,N′-bis(phenyl)benzidine (NPD, H. W. Sands Corp., Jupiter, Fla.), followed by 30 nm of aluminum tris(8-hydroxyquinolate) (AlQ, H. W. Sands Corp, Jupiter, Fla.) doped with ca. 1 wt. % of green-emitting Coumarin 545T (C545T, Eastman Kodak Co., Rochester, N.Y.), and followed by 20 nm of AlQ. The OLED was capped with a cathode composed of ca. 0.7 nm of lithium fluoride (LiF, Alfa Aesar Co., Ward Hill, Mass.) and 200 nm of aluminum (Al, Alfa Aesar Co., Ward Hill, Mass.). In this OLED construction, the NPD layer acts as a hole-transport layer and electron-blocking layer, the layer of AlQ doped with C545T (AlQ:C545T) acts as a light emitting layer, and the layer of AlQ acts as an electron injection and transport layer. These OLED constructions are further referred to as “/NPD/AlQ:C545T/AlQ/LiF/Al”.
- All organic and cathode layers except the buffer layers were fabricated in a standard vacuum-deposition procedure at a base vacuum of ca. 10−7 to 10−5 torr (about 10−5 to 10−3 Pa) with evaporation rates of 0.05-0.2 nm/s for organic materials, 0.05 nm/s for LiF, and 1.5-2 nm/s for Al.
- In Comparative Example 1, polypyrrole (PPY, Aldrich Chemical Co.) was used as a control hole-injecting buffer layer for purposes of comparison of the OLED behavior of the devices deposited onto PPY and onto doped triarylamine-based buffer layers. PPY was spun-coat from its water suspension after filtering the suspension through 0.2 μm Nylon microfilters, followed by annealing under nitrogen gas flow at 110° C. for ca. 15 min.
- In Examples 1-4, OLEDs with buffer layers containing MTDATA, PS, and TCNQ were prepared and their performance evaluated along with that of the control PPY-based OLEDs. MTDATA, PS, and TCNQ were purchased from H W Sands Corp. (Jupiter, Fla.), Polysciences Inc. (Eppelheim, Germany), and TCI America (Portland, Oreg.), respectively. The buffer layers were spun-coat from their ca. 1.5 wt. % solutions in toluene at the spin-rate of 2000 RPM (about 33 s−1) to form ca. 90 nm thick films on the ITO coated substrates. The device structures are glass-ITO/buffer layer/NPD/AlQ:C545T/AlQ/LiF/Al. The buffers layers for the Examples are:
- Comparative Example 1: PPY
- Example. 1: 31 wt. % PS, 62 wt. % MTDATA, and 7 wt. % TCNQ
- Example 2: 47 wt. % PS, 46 wt. % MTDATA, and 7 wt. % TCNQ
- Example 3: 62 wt. % PS, 31 wt. % MTDATA, and 7 wt. % TCNQ
- No short-circuiting was observed in any of the studied electroluminescent lamps. For Examples 1-3, the OLEDs showed high operational efficiency and low operational voltages, with operational voltages decreasing with increasing triarylamine concentration.
- High bandgap hole-transporting poly(N-vinylcarbazole) (PVK, Polymer Source Inc., Dorval, Quebec) having relatively high oxidation potential (ca. 1V vs. SCE) and low hole mobility (ca. 10−6−10−5 cm2/V*s (about 10−10−10−9 m2/V s)) was used as an electroactive binder in the following buffer compositions: a) 60 wt. % PVK and 40 wt. % MTDATA, and b) 56 wt. % PVK, 37 wt. % MTDATA, and 7 wt. % F4-TCNQ. These buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s−1) to form ca. 90 nm thick films on the ITO coated substrates.
- OLED devices were made as described above for Comparative Example 1 and Examples 1-3, except that the buffer layers corresponded to:
- Example 5: 60 wt. % PVK and 40 wt. % MTDATA
- Example 6: 56 wt. % PVK, 37 wt. % MTDATA, and 7 wt. % F4-TCNQ
- No short-circuiting was observed in any of the studied electroluminescent lamps. Luminance-voltage-current density screening of the OLEDs indicated that high efficiencies can be obtained in the composition including triarylamine-based buffers along with low operational voltages. Doping the PVK:MTDATA blend with F4-TCNQ significantly lowered the operational voltage of the OLEDs. Operational lifetime studies on the triarylamine-based compositions, in which the OLEDs were driven at a constant current of ca. 1.8 mA/cm2 (about 18 A/m2) under inert atmosphere, show that projected operation lifetimes of these OLEDs extend into 103-104 hours range at an initial luminance of several hundred Cd/m2.
- In this Example, doped triarylamine buffer layers based on copolymers incorporating triarylamine moieties as a functionality pendant to a polyolefin backbone were incorporated into OLEDs.
- A block co-polymer of styrene with diphenylaminostyrene (PS-pDPAS), having approximately 6:1 molar ratio of the monomers was synthesized and screened as a triarylamine-containing polymer.
- All materials are available from Aldrich Chemical Co., Milwaukee, Wis., with the exception of p-diphenylaminostyrene, and as where noted. This monomer was synthesized by a preparation similar to that described by G. N. Tew, M. U. Pralle, and S. I. Stupp inAngew. Chem. Int. Ed., 2000, 39, 517, incorporated herein by reference.
- Synthesis of p-diphenylaminostyrene
- To a mixture of 4-(diphenylamino)benzaldehyde (20.06 g, 73 mmol, Fluka Chemical Co., Milwaukee, Wis.), methyltriphenyl phosphonium bromide (26.22 g, 73 mmol) and dry tetrahydrofuran (450 mL) under nitrogen was added a IM solution of potassium t-butoxide in tetrahydrofuran (80 mL, 80 mmol) over 5 minutes. The mixture was stirred for 17 hours at room temperature. Water (400 mL) was added and the tetrahydrofuran was removed under reduced pressure. The mixture was extracted with ether, and the combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude solid was purified by column chromatography on silica gel using a 50/50 mixture of methylene chloride and hexane to give a yellow solid that was further recrystallized once from hexane (15.37 g, 78%).
- Synthesis of Block Co-Polymer of Styrene With Diphenylaminostyrene (PS-pDPAS)
- A round-bottom glass reactor was baked out under vacuum at 200° C. for 2 hours, then allowed to cool. The reactor was filled with dry nitrogen. Subsequently, 71.8 g of cyclohexane and 4.4 mL of tetrahydrofuran (THF) were added to the reactor by syringe. The THF was distilled from sodium/benzophenone solution under nitrogen prior to use, in order to scavenge water and oxygen. The cyclohexane was dried by passage through activated basic alumina, followed by sparging with nitrogen gas for 30 minutes prior to use. After addition of the solvents, the reaction flask was cooled to 3° C. in an ice water bath, after which 0.02 mL of styrene was added to the reactor. The styrene had previously been passed through activated basic alumina to remove inhibitors and water, and sparged with nitrogen gas to remove oxygen. A solution of s-butyllithium in cyclohexane (0.4 mL, 1.3 mol/L) was subsequently added to the reactor. The solution immediately turned orange, characteristic of the formation of polystyryl anion. After stirring at 3° C. for 2 hours, a solution of p-diphenylaminostyrene (1.61 g) in cyclohexane (20 mL) was added to the reactor by cannula. This solution had previously been degassed by repeatedly freezing it with liquid nitrogen and exposing it to vacuum. The solution was stirred overnight while warming to room temperature. The reaction was then terminated by addition of methanol, precipitated into a mixture of methanol and isopropanol, and dried under in a vacuum oven overnight, yielding 3.2 g of polymer. The resulting PS-pDPAS block polymer contained 74.1 mol % styrene and 25.9 mol % p-diphenylaminostyrene, based on13C NMR. The molecular weight of the block copolymer was 7700 g/mol, based on gel permeation chromatography in THF against polystyrene standards.
- OLED Preparation
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Example 7: PS-pDPAS
- Example 8: 93 wt. % PS-pDPAS and 7 wt. % F4-TCNQ
- These buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s−1) to form ca. 90 nm thick films on the ITO coated substrates.
- No short-circuiting was observed in any of the studied electroluminescent lamps. Luminance-voltage-current density screening of the OLEDs indicated that high efficiencies and low operational voltages were obtained. Doping PS-pDPAS with F4-TCNQ significantly lowered the operational voltage of the OLEDs.
- Buffer Layers Containing Conjugated Copolymers With Triarylamine Moieties in the Backbone
- This describes the preparation and characterization of an OLED with doped co-polymer based triarylamine hole injecting buffer layers. The buffer layers include PEDT (poly(3,4-ethylenedioxythiophene) available as CH8000 from Bayer A G, Leverkusen, Germany), undoped poly{(9-phenyl-9H-carbazole-3,6-diyl)[N,N′-bis(phenyl-4-yl)-N,N′-bis(4-butylphenyl)benzene-1,4-diamine]} (Cz-triarylamine), and Cz-triarylamine doped with F4-TCNQ. An advantage of using Cz-triarylamine as a triarylamine-containing co-polymer for hole injecting buffer layers lies in the presence of phenylenediamine linkages, which typically cause lower ionization potential (higher energy of the highest occupied molecular orbital). This provides favorable conditions for increased conductivity due to doping with electron acceptors (e.g. F4-TCNQ).
- 3,6-Dibromo-9-phenylcarbazole was made according to M. Park, J. R. Buck, C. J. Rizzo, J. Carmelo. Tetrahedron 119, 54 (42), 12707-12714, incorporated herein by reference. N,N′-bis(4-bromophenyl)-N,N′-bis(4-butylphenyl)benzene-1,4-diamine can be obtained in two steps from 1,4-phenylenediamine as reported in Raymond et al., Polymer Preprints 2001, 42(2), 587-588, incorporated herein by reference. Tricaprylylmethylammonium chloride is available from Aldrich Chemical Company under the trade name Aliquat® 336. All other materials were obtained from Aldrich Chemical Company.
- Preparation of 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
- A 2L flask was charged with 600 mL dry THF and 3,6-dibrimo-9-phenylcarbazole (60 g, 0.15 mole). This was cooled to −78° C. with an acetone-dry ice bath. n-Butyllithium (138 mL of a 2.5M solution in hexanes, 0.34 mole) was added drop-wise via syringe. The reaction was stirred for 20 minutes and then warmed to −50° C. The temperature was reduced to −78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (64 g, 0.34 mole) added via syringe at such a rate as to maintain the temperature below −60° C. The reaction was maintained at −78° C. for two hours and then poured into an aqueous solution of ammonium acetate (90 g in 2100 mL water). The layers were phase separated and the aqueous phase extracted with methyl tert-butyl ether (2×200 mL). The combined organic phase and extracts were washed with brine (2×200 mL) and dried over magnesium sulfate. Concentration and re-crystallization of the solid obtained form acetone gave pure 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12 g, 16% yield).
- Preparation of Poly{(9-phenyl-9H-carbazole-3,6-diyl)[N,N′-bis(phenyl-4-yl)-N,N′-bis(4-butylphenyl)benzene-1,4-diamine)]} (Cz-triarylamine—Formula 32 Above)
- In a 50 mL round bottomed flask fitted with a rubber septum and reflux condenser were introduced 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (0.79 g, 1.59 mmole, 5 equivalents), N,N′-bis(4-bromophenyl)-N,N′-bis(4-butylphenyl)benzene-1,4-diamine (0.65 g, 0.952 mmol, 3 equivalents), Aliquat® 336 (0.16 g, 0.405 mmole, 1.28 equivalents), 2M sodium carbonate solution (5.4 mL, 10.8 mmol, 34 equivalents) and 20 mL toluene. This was purged with a stream of nitrogen for 30 min. Under a nitrogen purge, tetrakistriphenylphosphine palladium (0) (10 mg, 0.0.0068 mmole, 0.02 equivalents) was added. The reaction mixture was then refluxed for 16 hrs. A solution of 0.5 g bromobenzene in 5 mL purged toluene was added followed by and a further charge of tetrakistriphenylphosphine paladium (0) (10 mg) and refluxing then continued for a further 16 hrs.
- The reaction was then cooled to room temperature and 30 mL water added. The organic layer was separated and washed with water followed by brine. Precipitation into methanol, filtration and vacuum drying of the solid thus obtained gave 0.62 g of the required hole transport polymer. Molecular weight determination by gel permeation chromatography versus polystyrene standards gave Mw 2.39×103, Mn 1.49×103 and polydispersity of 1.67
- OLED Preparation
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Comparative Example 2: PEDT
- Example 9: Cz-triarylamine
- Example 10: 93 wt. % Cz-triarylamine and 7 wt. % F4-TCNQ.
- These buffer layers were spun-coat from their ca. 1.5% wt. solutions in toluene at the spin-rate of 2000 RPM (about 33 s−1) to form ca. 90 nm thick films on the ITO coated substrates.
- No short-circuiting was observed in any of the studied electroluminescent lamps. Devices with both doped and undoped Cz-triarylamine-based buffer layer showed high external quantum efficiencies. Devices with undoped Cz-triarylamine buffer layer showed noticeably higher operational voltages than those made on PEDT. Upon doping Cz-triarylamine with F4-TCNQ, operational voltages decreased to the level of those observed for PEDT-based LEDs. This indicates that Cz-triarylamine possesses an ionization potential which is low enough for efficient F4-TCNQ doping to increase conductivity in the hole-injecting buffer layer.
- Preliminary operation stability studies on devices incorporating Cz-triarylamine buffer layer carried out in the constant current continuous sweep regime at current density levels of ca. 1.8 mA/cm2 (luminance of 100-150 Cd/m2) suggest that Cz-triarylamine-based buffer layers can be used to achieve improved operational lifetime in OLEDs.
- This Example describes the fabrication of hole-injecting solution-processed buffer layers based on doped triarylamines blended with electroactive polymer binder and blended with color-converting organic dye material in order to tune electroluminescence energy and CIE color coordinates of the OLEDs incorporating such buffer layers.
- Three solutions consisting of a) 30 mg poly(vinyl carbazole) (PVK, Aldrich Chemical Co.), 20 mg MTDATA (H. W. Sands Corp., Jupiter, Fla.), 2 mg F4-TCNQ (TCI America, Portland, Oreg.), 3.7 ml CHCl3, b) 30 mg PVK, 20 mg MTDATA, 2 mg F4-TCNQ, 75 mg 1,4-bis(2-methyl-6-ethyl anilino) anthraquinone (Dye), 3.7 ml CHCl3 and, c) 30 mg PVK, 20 mg MTDATA, 2 mg F4-TCNQ, 117 mg 1,4-bis(2-methyl-6-ethyl anilino) anthraquinone (Dye), 3.7 ml CHCl3 were prepared. The Dye can be prepared according to U.S. Pat. No. 5,639,896, incorporated herein by reference and is available as “Amaplast Blue RFC” supplied by “American Aniline Products”, N.Y., N.Y., a unit of Koppers Co., Pittsburgh, Pa. Each solution was then spun coat onto cleaned ITO substrates at 3000 R.P.M. for 30 s. A vapor deposited small-molecule OLED with NPD (20 nm, 0.2 nm/s), AlQ (50 nm, 0.1 nm/s), LiF (0.7 nm, 0.05 nm/s), Al (200 nm, 2 nm/s) was sequentially deposited on top in a standard vacuum deposition procedure at 10-6 torr (about 10-4 Pa) as described in Comparative Example 1 and Examples 1-3.
- OLEDs were formed as described in the Comparative Example 1 and Examples 1-3 except that the buffer layers were as follows:
- Example 11: Solution a) corresponding to 58 wt. % PVK, 38 wt. % MTDATA and 4 wt. % F4-TCNQ
- Example 12: Solution b) corresponding to 24 wt. % PVK, 16 wt. % MTDATA, 2 wt. % F4-TCNQ, and 58 wt. % Dye
- Example 13: Solution c) corresponding to 18 wt. % PVK, 12 wt. % MTDATA, 1 wt. % F4-TCNQ, and 69 wt. % Dye.
- Devices containing the dye in the buffer layer exhibit a clear change in the electroluminescence spectrum and the corresponding C.I.E coordinates due to selective absorption of the AlQ emission by the dye. CIE color coordinates for two hole-injecting buffer layer compositions containing the studied dye material in different concentrations as well as those for the control device are shown in Table I.
TABLE I Color Coordinate Shift Sample CIE (x) CIE (y) Example 11 0.34 0.55 Example 12 0.20 0.56 Example 13 0.17 0.57 - Preparation of a Donor Sheet Without a Transfer Layer
- A thermal transfer donor sheet was prepared in the following manner:
- An LTHC solution, given in Table II, was coated onto a 0.1 mm thick polyethylene terephthalate (PET) film substrate (M7 from Teijin, Osaka, Japan). Coating was performed using a Yasui Seiki Lab Coater, Model CAG-150, using a microgravure roll with 150 helical cells per inch. The LTHC coating was in-line dried at 80° C. and cured under ultraviolet (UV) radiation.
TABLE II LTHC Coating Solution Parts by Component Trade Designation Weight carbon black pigment Raven 760 Ultra(1) 3.55 polyvinyl butyral resin Butvar B-98(2) 0.63 acrylic resin Joncryl 67(3) 1.90 Dispersant Disperbyk 161(4) 0.32 Surfactant FC-430(5) 0.09 epoxy novolac acrylate Ebecryl 629(6) 12.09 acrylic resin Elvacite 2669(7) 8.06 2-benzyl-2-(dimethylamino)-1-(4- Irgacure 369(8) 0.82 (morpholinyl)phenyl)butanone 1-hydroxycyclohexyl phenyl ketone Irgacure 184(8) 0.12 2-butanone 45.31 1,2-propanediol monomethyl ether 27.19 acetate - Next, an interlayer solution, given in Table III, was coated onto the cured LTHC layer by a rotogravure coating method using the Yasui Seiki lab coater, Model CAG-150, with a microgravure roll having 180 helical cells per lineal inch. This coating was in-line dried at 60° C. and cured under ultraviolet (UV) radiation.
TABLE III Interlayer Coating Solution PARTS BY COMPONENT WEIGHT SR 351 HP (trimethylolpropane triacrylate 14.85 ester, available from Sartomer, Exton, PA) Butvar B-98 0.93 Joncryl 67 2.78 Irgacure 369 1.25 Irgacure 184 0.19 2-butanone 48.00 1-methoxy-2-propanol 32.00 - Preparation of Solutions for Receptor
- The following solutions were prepared and used in the preparation of layers on the receptor substrate:
- MTDATA: (4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine) (OSA 3939, H. W. Sands Corp., Jupiter, Fla.) 1.0% (w/w) in toluene was filtered and dispensed through a Whatman Puradisc™ 0.45 μm Polypropylene (PP) syringe filter.
- PVK: Poly(9-vinylcarbazole) (Aldrich Chemical Co., Milwaukee, Wis.) 1.0% (w/w) in toluene was filtered and dispensed through a Whatman Puradisc™ 0.45 μm Polypropylene (PP) syringe filter.
- F4-TCNQ: Tetrafluorotetracyanoquinodimethane (Tokyo Kasei Kogyo Co., Tokyo, Japan) 0.25% (w/w) in toluene was filtered and dispensed through a Whatman Puradisc™ 0.45 μm Polypropylene (PP) syringe filter.
- MTDATA/F4-TCNQ: 98/2 w/w% mixture of MTDATA/F4-TCNQ.
- MTDATA/PVK: 65/35 w/w% mixture of MTDATA/PVK
- MTDATA/PVK/F4-TCNO: 64/35/1 w/w/w% mixture of MTDATA/PVK/F4-TCNQ
- Preparation of Receptors
- Receptors were formed as follows: ITO(indium tin oxide) glass (Delta Technologies, Stillwater, Minn., less than 100 Ω/square, 1.1 mm thick) was processed using photolithography to provide a patterned ITO structure capable of making an electroluminescent device. The substrate was ultrasonically cleaned in a hot, 3% solution of Deconex 12NS (Borer Chemie A G, Zuchwil Switzerland). The substrates were then placed in the Plasma Science plasma treater for surface treatment under the following conditions:
Time: 2 minutes Power: 500 watt (165 W/cm2) Oxygen Flow: 100 sccm - Immediately after plasma treatment, a solution of material was applied to the surface of the ITO according to Table IV below.
TABLE IV Preparation of receptors Spin Film Receptor Receptor Coating speed thickness number Solution Composition (RPM) (nm) 1 MTDATA Neat 1000 40 2 MTDATA/F4- 98/2 w/w % 1000 40 TCNQ 3 MTDATA/PVK 65/35 w/w % 1000 40 4 MTDATA/PVK/F4- 64/35/1 w/w/w % 1000 40 TCNQ - Preparation of Solutions for Transfer Layer
- The following solutions were prepared:
- Covion Super Yellow: Covion PPV polymer PDY 132 “Super Yellow” (75 mg) from Covion Organic Semiconductors GmbH, Frankfurt, Germany was weighed out into an amber vial with a PTFE cap. To this was added 9.925 g of toluene (HPLC grade obtained from Aldrich Chemical, Milwaukee, Wis.). The solution was stirred over night. The solution was filtered through a 5 μm Millipore Millex syringe filter.
- Polystyrene: Polystyrene (250 mg) from Aldrich Chemical, Milwaukee, Wis. (Mw=2,430) was dissolved in 9.75 g of toluene (HPLC grade obtained from Aldrich Chemical, Milwaukee, Wis.). The solution was filtered through a 0.45 μm polypropylene (PP) syringe filter.
- Preparation of Transfer Layers on Donor Sheet and Transfer of Transfer Layers.
- Transfer layers were formed on the donor sheets using a 33/67 w/w% blend of the solutions of Covion Super Yellow and polystyrene from the previous section. To obtain the blends, the above-described solutions were mixed at the appropriate ratios and the resulting blend solutions were stirred for 20 min at room temperature.
- The transfer layers were disposed on the donor sheets by spinning (Headway Research spincoater) the blend solution at about 2000-2500 rpm for 30 s to yield a film thickness of approximately 100 nm.
- The donor sheets coated with Covion Super Yellow/polystyrene were brought into contact with each of the receptor substrates prepared in an above section. Next, the donor sheets were imaged using two single-mode Nd:YAG lasers. Scanning was performed using a system of linear galvanometers, with the combined laser beams focused onto the image plane using an f-theta scan lens as part of a near-telecentric configuration. The laser energy density was 0.4 to 0.8 J/cm2. The laser spot size, measured at the 1/e2 intensity, was 30 micrometers by 350 micrometers. The linear laser spot velocity was adjustable between 10 and 30 meters per second, measured at the image plane. The laser spot was dithered perpendicular to the major displacement direction with about a 100 nm amplitude. The transfer layers were transferred as lines onto the receptor substrates, and the intended width of the lines was about 100 nm.
- The transfer layers were successfully transferred in a series of lines that were in overlying registry with the ITO stripes on the receptor substrates, resulting in good imaging transfer.
- Preparation of OEL Devices
- Electroluminescent devices were prepared by depositing calcium/silver cathodes on top of the LEP (Covion Super Yellow/PS) transferred in the above section. Approximately 40 nm of calcium was vapor deposited at a rate of 0.11 nm/s onto the LEP, followed by approximately 400 nm of silver at a rate of 0.5 nm/s. In all cases, diode behavior and yellow light emission was observed.
- The present invention should not be considered limited to the particular examples described above, but rather should be understood to cover all aspects of the invention as fairly set out in the attached claims. Various modifications, equivalent processes, as well as numerous structures to which the present invention may be applicable will be readily apparent to those of skill in the art to which the present invention is directed upon review of the instant specification.
Claims (29)
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/183,717 US20040004433A1 (en) | 2002-06-26 | 2002-06-26 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
AT03777517T ATE358336T1 (en) | 2002-06-26 | 2003-05-07 | BUFFER LAYERS FOR ORGANIC ELECTROLUMINESCENCE DEVICES AND METHOD FOR THE PRODUCTION AND USE THEREOF |
KR1020047021123A KR101011428B1 (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
CNA2008101440501A CN101325247A (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
AU2003286999A AU2003286999A1 (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
JP2004532564A JP2005531915A (en) | 2002-06-26 | 2003-05-07 | Buffer layer for organic electroluminescent devices, and methods of manufacture and use |
PCT/US2003/014466 WO2004021463A2 (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
EP03777517A EP1518281B8 (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
CN038150581A CN1666356A (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
DE60312861T DE60312861T2 (en) | 2002-06-26 | 2003-05-07 | BUFFER LAYERS FOR ORGANIC ELECTROLUMINESCENZING DEVICES AND METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
MXPA04012432A MXPA04012432A (en) | 2002-06-26 | 2003-05-07 | Buffer layers for organic electroluminescent devices and methods of manufacture and use. |
TW092115415A TW200402248A (en) | 2002-06-26 | 2003-06-06 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
MYPI20032162A MY135888A (en) | 2002-06-26 | 2003-06-10 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US11/118,574 US7166010B2 (en) | 2002-06-26 | 2005-04-29 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US11/609,066 US20070079927A1 (en) | 2002-06-26 | 2006-12-11 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US13/773,533 US20130164875A1 (en) | 2002-06-26 | 2013-02-21 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/183,717 US20040004433A1 (en) | 2002-06-26 | 2002-06-26 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/118,574 Division US7166010B2 (en) | 2002-06-26 | 2005-04-29 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
Publications (1)
Publication Number | Publication Date |
---|---|
US20040004433A1 true US20040004433A1 (en) | 2004-01-08 |
Family
ID=29999217
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/183,717 Abandoned US20040004433A1 (en) | 2002-06-26 | 2002-06-26 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US11/118,574 Expired - Lifetime US7166010B2 (en) | 2002-06-26 | 2005-04-29 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US11/609,066 Abandoned US20070079927A1 (en) | 2002-06-26 | 2006-12-11 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US13/773,533 Abandoned US20130164875A1 (en) | 2002-06-26 | 2013-02-21 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/118,574 Expired - Lifetime US7166010B2 (en) | 2002-06-26 | 2005-04-29 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US11/609,066 Abandoned US20070079927A1 (en) | 2002-06-26 | 2006-12-11 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US13/773,533 Abandoned US20130164875A1 (en) | 2002-06-26 | 2013-02-21 | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
Country Status (12)
Country | Link |
---|---|
US (4) | US20040004433A1 (en) |
EP (1) | EP1518281B8 (en) |
JP (1) | JP2005531915A (en) |
KR (1) | KR101011428B1 (en) |
CN (2) | CN1666356A (en) |
AT (1) | ATE358336T1 (en) |
AU (1) | AU2003286999A1 (en) |
DE (1) | DE60312861T2 (en) |
MX (1) | MXPA04012432A (en) |
MY (1) | MY135888A (en) |
TW (1) | TW200402248A (en) |
WO (1) | WO2004021463A2 (en) |
Cited By (87)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020060654A1 (en) * | 2000-11-23 | 2002-05-23 | Lg.Philips Lcd Co., Ltd. | Electroluminescence display device |
US20040085015A1 (en) * | 2002-11-06 | 2004-05-06 | Lg.Philips Lcd Co., Ltd. | Oraganic electro-luminescent device having polymer emission layer and method for fabricating the same |
US20040109955A1 (en) * | 2002-08-28 | 2004-06-10 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US20040146744A1 (en) * | 2002-07-31 | 2004-07-29 | Satoshi Seo | Material for an electroluminescence element and electroluminescence element using the same |
US20040183066A1 (en) * | 2003-03-18 | 2004-09-23 | Eastman Kodak Company | P-type materials and mixtures for electronic devices |
US20050082523A1 (en) * | 2003-06-26 | 2005-04-21 | Blanchet-Fincher Graciela B. | Methods for forming patterns on a filled dielectric material on substrates |
US20050184287A1 (en) * | 2004-02-20 | 2005-08-25 | Norman Herron | Cross-linkable polymers and electronic devices made with such polymers |
US20050191776A1 (en) * | 2002-06-26 | 2005-09-01 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20050282307A1 (en) * | 2004-06-21 | 2005-12-22 | Daniels John J | Particulate for organic and inorganic light active devices and methods for fabricating the same |
US20060022590A1 (en) * | 2004-08-02 | 2006-02-02 | Xerox Corporation | OLEDs having inorganic material containing anode capping layer |
US20060022585A1 (en) * | 2004-08-02 | 2006-02-02 | Xerox Corporation | OLEDs having improved luminance stability |
US20060087225A1 (en) * | 2004-10-22 | 2006-04-27 | Eastman Kodak Company | White OLEDs with a color-compensated electroluminescent unit |
US20060099448A1 (en) * | 2003-04-28 | 2006-05-11 | Zheng-Hong Lu | Top light-emitting devices with fullerene layer |
US20060102893A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compoounds |
US20060103299A1 (en) * | 2004-11-15 | 2006-05-18 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode & method of making the same |
US20060102911A1 (en) * | 2004-11-17 | 2006-05-18 | Seoung-Yoon Ryu | Organic light emitting display and method of fabricating the same |
US20060105199A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Electroluminescent devices containing trans-1,2-bis(acenyl)ethylene compounds |
WO2006080553A1 (en) * | 2005-01-31 | 2006-08-03 | Semiconductor Energy Laboratory Co., Ltd. | Hole-injecting material, material for light-emitting element, light-emitting element, organic compound, monomer, and monomer mixture |
US20060182993A1 (en) * | 2004-08-10 | 2006-08-17 | Mitsubishi Chemical Corporation | Compositions for organic electroluminescent device and organic electroluminescent device |
JP2006237592A (en) * | 2005-01-31 | 2006-09-07 | Semiconductor Energy Lab Co Ltd | Hole-injecting material, light emitting device material, light emitting device, organic compound, monomer and monomer mixture |
US20060228974A1 (en) * | 2005-03-31 | 2006-10-12 | Theiss Steven D | Methods of making displays |
US20060251919A1 (en) * | 2005-05-04 | 2006-11-09 | Xerox Corporation | Organic light emitting devices |
US20060263593A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Display devices with light absorbing metal nonoparticle layers |
US20060263628A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Display device with metal-organic mixed layer anodes |
US20060263629A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Intermediate electrodes for stacked OLEDs |
US20060261731A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Stacked oled structure |
US20060284533A1 (en) * | 2005-06-21 | 2006-12-21 | Au Optronics Corp. | Organic electroluminescent device |
EP1753047A2 (en) * | 2005-08-08 | 2007-02-14 | Osram Opto Semiconductors GmbH | Solution processed crosslinkable hole injection and hole transport polymers for oleds |
US20070054151A1 (en) * | 2005-09-08 | 2007-03-08 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US20070128465A1 (en) * | 2005-12-05 | 2007-06-07 | General Electric Company | Transparent electrode for organic electronic devices |
US20070126347A1 (en) * | 2005-12-01 | 2007-06-07 | Eastman Kodak Company | OLEDS with improved efficiency |
WO2007087954A1 (en) * | 2006-02-03 | 2007-08-09 | Tridonicatco Optoelectronics Gmbh | Light emitting device with a non-activated luminescent material |
US20070216292A1 (en) * | 2004-12-06 | 2007-09-20 | Satoshi Seo | Composite Material Including organic Compound And Inorganic Compound Light-Emitting Element And Light-Emitting Device Using The Composite Compound, And Manufacturing Method Of The Light-Emitting Element |
US20070241665A1 (en) * | 2006-04-12 | 2007-10-18 | Matsushita Electric Industrial Co., Ltd. | Organic electroluminescent element, and manufacturing method thereof, as well as display device and exposure apparatus using the same |
US20070275624A1 (en) * | 2005-12-14 | 2007-11-29 | Fuji Electric Holdings Co., Ltd. | Method of the manufacturing an organic EL display |
US20080003455A1 (en) * | 2004-12-08 | 2008-01-03 | Fuji Electric Holdings Co., Ltd. | Organic El Device |
US20080071049A1 (en) * | 2006-08-24 | 2008-03-20 | Radu Nora S | Hole transport polymers |
US20080160348A1 (en) * | 2006-12-29 | 2008-07-03 | Eric Maurice Smith | Benzofluorenes for luminescent applications |
US20080160789A1 (en) * | 2002-12-19 | 2008-07-03 | 3M Innovative Properties Company | Laser patterning of encapsulated organic light emitting diodes |
US20080254306A1 (en) * | 2007-04-10 | 2008-10-16 | Yong-Tak Kim | Method of manufacturing organic light-emitting device and organic light-emitting device manufactured using the method |
US20080297040A1 (en) * | 2007-06-01 | 2008-12-04 | Weishi Wu | Charge transport materials for luminescent applications |
US20090001878A1 (en) * | 2007-04-03 | 2009-01-01 | Tsinghua University | Organic electroluminescent device |
US20090015757A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode lighting devices |
US20090015142A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode display devices |
US20090051277A1 (en) * | 2007-08-21 | 2009-02-26 | Katsumi Inoue | Organic electroluminescent display |
US20090072714A1 (en) * | 2005-03-23 | 2009-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Composite Material, Material for Light-Emitting Element, Light-Emitting Element, Light-Emitting Device and Electronic Device |
US20100110551A1 (en) * | 2008-10-31 | 2010-05-06 | 3M Innovative Properties Company | Light extraction film with high index backfill layer and passivation layer |
US20100150513A1 (en) * | 2008-12-17 | 2010-06-17 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
US20100187513A1 (en) * | 2008-04-23 | 2010-07-29 | Panasonic Corporation | Organic electroluminescence element |
US20100187506A1 (en) * | 2008-12-01 | 2010-07-29 | Park Kyung-Ho | Electroactive materials |
US20100187507A1 (en) * | 2008-12-04 | 2010-07-29 | Park Kyung-Ho | Electroactive materials |
US20100187518A1 (en) * | 2007-07-12 | 2010-07-29 | Sumitomo Chemical Company, Limited | Method of producing organic light emitting device |
US7777407B2 (en) | 2005-05-04 | 2010-08-17 | Lg Display Co., Ltd. | Organic light emitting devices comprising a doped triazine electron transport layer |
US20100213825A1 (en) * | 2008-12-01 | 2010-08-26 | Park Kyung-Ho | Electroactive materials |
US7795806B2 (en) | 2005-05-20 | 2010-09-14 | Lg Display Co., Ltd. | Reduced reflectance display devices containing a thin-layer metal-organic mixed layer (MOML) |
US20100252819A1 (en) * | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
WO2010115767A1 (en) | 2009-04-08 | 2010-10-14 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
US20110037056A1 (en) * | 2008-12-12 | 2011-02-17 | E. I. Du Pont De Nemours And Company | Photoactive composition and electronic device made with the composition |
US20110095273A1 (en) * | 2009-09-29 | 2011-04-28 | E. I. Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
US20110253985A1 (en) * | 2009-10-19 | 2011-10-20 | E. I. Du Pont De Nemours And Company | Triarylamine compounds for electronic applications |
US20110253986A1 (en) * | 2009-10-19 | 2011-10-20 | E. I. Du Pont De Nemours And Company | Triarylamine compounds for electronic applications |
US8053973B2 (en) | 2005-02-15 | 2011-11-08 | Pioneer Corporation | Film forming composition and organic electroluminescent device |
WO2012041849A1 (en) | 2010-09-29 | 2012-04-05 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
US8236990B2 (en) | 2004-03-31 | 2012-08-07 | E I Du Pont De Nemours And Company | Triarylamine compounds, compositions and uses therefor |
WO2012175530A1 (en) | 2011-06-22 | 2012-12-27 | Basf Se | Diketopyrrolopyrrole oligomers for use in organic semiconductor devices |
US8343381B1 (en) * | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
US20130048973A1 (en) * | 2010-04-06 | 2013-02-28 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Organic Light-Emitting Diode Comprising At Least Two Electroluminescent Layers |
WO2013030325A1 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
WO2013022792A3 (en) * | 2011-08-08 | 2013-05-02 | Quarkstar Llc | Method and apparatus for coupling light-emitting elements with light-converting material |
US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
US8652655B2 (en) | 2007-11-19 | 2014-02-18 | E I Du Pont De Nemours And Company | Electroactive materials |
US20140114040A1 (en) * | 2011-05-26 | 2014-04-24 | Peakdale Molecular Limited | Semiconductor compounds |
US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
WO2016028906A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
WO2016028902A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Compositions containing benzocyclobutene substituted carbazoles, and electronic devices containing the same |
US9293716B2 (en) | 2010-12-20 | 2016-03-22 | Ei Du Pont De Nemours And Company | Compositions for electronic applications |
US9318715B2 (en) * | 2014-05-21 | 2016-04-19 | E I Du Point De Nemours And Company | Hole transport composition without luminance quenching |
US9431145B2 (en) | 2011-05-26 | 2016-08-30 | Neudrive Limited | Transistors and methods for making them |
US20160301022A1 (en) * | 2013-07-03 | 2016-10-13 | Corning Precision Materials Co., Ltd. | Substrate for photoelectric device and photoelectric device comprising same |
US9496506B2 (en) | 2009-10-29 | 2016-11-15 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
US9701899B2 (en) | 2006-03-07 | 2017-07-11 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
US9815996B2 (en) | 2007-06-25 | 2017-11-14 | Samsung Electronics Co., Ltd. | Compositions and methods including depositing nanomaterial |
US9874674B2 (en) | 2006-03-07 | 2018-01-23 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
US9929325B2 (en) | 2012-06-05 | 2018-03-27 | Samsung Electronics Co., Ltd. | Lighting device including quantum dots |
US10193075B2 (en) | 2014-03-14 | 2019-01-29 | Nissan Chemical Industries, Ltd. | Aniline derivative and use thereof |
US10256410B2 (en) | 2014-08-21 | 2019-04-09 | Dow Global Technologies Llc | Compositions comprising oxygen substituted benzocyclobutenes and dienophiles, and electronic devices containing the same |
Families Citing this family (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI302563B (en) * | 2002-09-24 | 2008-11-01 | Du Pont | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
US7317047B2 (en) * | 2002-09-24 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
ATE404609T1 (en) * | 2002-09-24 | 2008-08-15 | Du Pont | WATER DISPERSIBLE POLYTHIOPHENES PRODUCED USING COLLOIDS BASED ON POLYMERIC ACIDS |
WO2004029133A1 (en) * | 2002-09-24 | 2004-04-08 | E.I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
KR100991112B1 (en) * | 2002-12-19 | 2010-11-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Light-emitting device and method for manufacturing same |
US7390438B2 (en) * | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
KR100657891B1 (en) * | 2003-07-19 | 2006-12-14 | 삼성전자주식회사 | Semiconductor nanocrystal and method for preparing the same |
JP4300176B2 (en) * | 2003-11-13 | 2009-07-22 | ローム株式会社 | Organic electroluminescent device |
JP4378186B2 (en) * | 2004-02-06 | 2009-12-02 | キヤノン株式会社 | Organic EL element array |
US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
US8147962B2 (en) | 2004-04-13 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Conductive polymer composites |
KR100699993B1 (en) * | 2004-08-30 | 2007-03-26 | 삼성에스디아이 주식회사 | Method of laser induced thermal imaging |
KR20070085321A (en) * | 2004-10-12 | 2007-08-27 | 코닌클리즈케 필립스 일렉트로닉스 엔.브이. | Electroluminescent light source |
JP2006190995A (en) * | 2004-12-06 | 2006-07-20 | Semiconductor Energy Lab Co Ltd | Composite material comprising organic compound and inorganic compound, light emitting element and light emitting device employing the composite material as well as manufacturing method of the light emitting element |
JP2006216858A (en) * | 2005-02-04 | 2006-08-17 | Institute Of Physical & Chemical Research | Organic el element |
JP5134210B2 (en) * | 2005-05-17 | 2013-01-30 | 住友化学株式会社 | Polymer composition for organic electroluminescence |
US9297092B2 (en) | 2005-06-05 | 2016-03-29 | Qd Vision, Inc. | Compositions, optical component, system including an optical component, devices, and other products |
US8718437B2 (en) * | 2006-03-07 | 2014-05-06 | Qd Vision, Inc. | Compositions, optical component, system including an optical component, devices, and other products |
WO2009002512A1 (en) * | 2007-06-25 | 2008-12-31 | Qd Vision, Inc. | Compositions, optical component, system including an optical component, devices, and other products |
WO2007002740A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
CN101208369B (en) | 2005-06-28 | 2013-03-27 | E.I.内穆尔杜邦公司 | High work function transparent conductors |
GB0526185D0 (en) | 2005-12-22 | 2006-02-01 | Cambridge Display Tech Ltd | Electronic device |
US8216680B2 (en) | 2006-02-03 | 2012-07-10 | E I Du Pont De Nemours And Company | Transparent composite conductors having high work function |
US8849087B2 (en) | 2006-03-07 | 2014-09-30 | Qd Vision, Inc. | Compositions, optical component, system including an optical component, devices, and other products |
US9951438B2 (en) | 2006-03-07 | 2018-04-24 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
EP2041478B1 (en) * | 2006-03-07 | 2014-08-06 | QD Vision, Inc. | An article including semiconductor nanocrystals |
KR100777099B1 (en) * | 2006-03-08 | 2007-11-19 | 한국전자통신연구원 | High efficiency organic light emitting diodes and manufacturing method |
US20080061686A1 (en) * | 2006-03-22 | 2008-03-13 | Jie Liu | Phosphorescent light-emitting materials and methods of preparing |
DE102006013834A1 (en) * | 2006-03-23 | 2007-09-27 | Tesa Ag | Electroluminescent PSAs |
WO2007117698A2 (en) | 2006-04-07 | 2007-10-18 | Qd Vision, Inc. | Composition including material, methods of depositing material, articles including same and systems for depositing material |
KR101279315B1 (en) * | 2006-04-18 | 2013-06-26 | 이 아이 듀폰 디 네모아 앤드 캄파니 | High energy-potential bilayer compositions |
US8974918B2 (en) * | 2006-07-04 | 2015-03-10 | Semiconductor Energy Laboratory Co., Ltd. | Display device and electronic device |
US20080240479A1 (en) * | 2006-10-03 | 2008-10-02 | Sonic Innovations, Inc. | Hydrophobic and oleophobic coating and method for preparing the same |
US8846161B2 (en) * | 2006-10-03 | 2014-09-30 | Brigham Young University | Hydrophobic coating and method |
KR101270169B1 (en) * | 2006-11-13 | 2013-05-31 | 삼성전자주식회사 | Organic light emitting devices |
US8153029B2 (en) * | 2006-12-28 | 2012-04-10 | E.I. Du Pont De Nemours And Company | Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof |
US8062553B2 (en) * | 2006-12-28 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Compositions of polyaniline made with perfuoropolymeric acid which are heat-enhanced and electronic devices made therewith |
US20080191172A1 (en) * | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
US8836212B2 (en) * | 2007-01-11 | 2014-09-16 | Qd Vision, Inc. | Light emissive printed article printed with quantum dot ink |
US8003980B2 (en) * | 2007-01-30 | 2011-08-23 | Hewlett-Packard Development Company, L.P. | Layered electro-organic devices with crosslinked polymer and methods of preparing the same |
JP4450006B2 (en) * | 2007-04-02 | 2010-04-14 | ソニー株式会社 | Substrate for transfer and method for producing organic electroluminescent device |
US8241526B2 (en) | 2007-05-18 | 2012-08-14 | E I Du Pont De Nemours And Company | Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives |
JP4949149B2 (en) * | 2007-07-18 | 2012-06-06 | 富士フイルム株式会社 | Light emitting element |
WO2009014707A2 (en) | 2007-07-23 | 2009-01-29 | Qd Vision, Inc. | Quantum dot light enhancement substrate and lighting device including same |
US8128249B2 (en) * | 2007-08-28 | 2012-03-06 | Qd Vision, Inc. | Apparatus for selectively backlighting a material |
KR20100114052A (en) * | 2007-12-27 | 2010-10-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Buffer bilayers for electronic devices |
WO2009137053A1 (en) | 2008-05-06 | 2009-11-12 | Qd Vision, Inc. | Optical components, systems including an optical component, and devices |
US9207385B2 (en) | 2008-05-06 | 2015-12-08 | Qd Vision, Inc. | Lighting systems and devices including same |
WO2009151515A1 (en) | 2008-05-06 | 2009-12-17 | Qd Vision, Inc. | Solid state lighting devices including quantum confined semiconductor nanoparticles |
JP5644063B2 (en) * | 2008-05-07 | 2014-12-24 | 三菱化学株式会社 | Composition for organic electroluminescence device, polymer film, organic electroluminescence device, organic EL display and organic EL lighting |
US8216685B2 (en) * | 2008-05-16 | 2012-07-10 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
GB2462433B (en) * | 2008-08-05 | 2012-11-07 | Cambridge Display Tech Ltd | An organic electroluminescent device |
CN102273320B (en) * | 2008-11-13 | 2014-12-03 | 株式会社Lg化学 | Low voltage-driven organic electroluminescence device, and manufacturing method thereof |
EP2356168B1 (en) * | 2008-11-18 | 2015-05-27 | Solvay USA Inc. | Aminobenzene compositions and related devices and methods |
TWI393283B (en) * | 2008-12-04 | 2013-04-11 | Univ Nat Chiao Tung | Organic optoelectronic component |
US8461758B2 (en) * | 2008-12-19 | 2013-06-11 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
US8766239B2 (en) | 2008-12-27 | 2014-07-01 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
US8785913B2 (en) | 2008-12-27 | 2014-07-22 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
JP2010212354A (en) * | 2009-03-09 | 2010-09-24 | Mitsubishi Chemicals Corp | Composition for organic electroluminescent element and manufacturing method thereof, organic electroluminescent element, organic el display, and organic el illumination |
JP2012520381A (en) | 2009-03-12 | 2012-09-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Conductive polymer composition for coating applications |
JP2010225653A (en) * | 2009-03-19 | 2010-10-07 | Mitsubishi Chemicals Corp | Composition for charge transportation film, organic electroluminescent element, organic el display, and organic el illumination |
EP2421918B1 (en) | 2009-04-21 | 2020-08-26 | LG Chem, Ltd. | Electrically conductive polymer compositions and films made therefrom |
US8945427B2 (en) | 2009-04-24 | 2015-02-03 | E I Du Pont De Nemours And Company | Electrically conductive polymer compositions and films made therefrom |
EP2449561A2 (en) * | 2009-06-30 | 2012-05-09 | Plextronics, Inc. | Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same |
KR101174289B1 (en) | 2009-07-30 | 2012-08-14 | 엘지디스플레이 주식회사 | Organic Light Emitting Display Device |
EP2467371A2 (en) | 2009-09-04 | 2012-06-27 | Plextronics, Inc. | Organic electronic devices and polymers, including photovoltaic cells and diketone-based polymers |
US8120134B2 (en) * | 2009-10-15 | 2012-02-21 | Micron Technology, Inc. | High-performance diode device structure and materials used for the same |
EP2495287B1 (en) * | 2009-10-27 | 2018-05-16 | Samsung Electronics Co., Ltd. | Composition for anode buffer layers, high-molecular compound for anode buffer layers, organic electroluminescent element, process for production of same, and use thereof |
DE102010006280A1 (en) * | 2010-01-30 | 2011-08-04 | Merck Patent GmbH, 64293 | color conversion |
DE102010033777A1 (en) * | 2010-08-09 | 2012-02-09 | Merck Patent Gmbh | Polymers with carbazole structural units |
US20120049168A1 (en) * | 2010-08-31 | 2012-03-01 | Universal Display Corporation | Cross-Linked Charge Transport Layer Containing an Additive Compound |
EP2692747B1 (en) | 2011-03-28 | 2018-09-19 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
CN104247073B (en) * | 2012-04-16 | 2017-07-18 | 日本放送协会 | Organic electroluminescent device and its manufacture method |
WO2014073683A1 (en) * | 2012-11-12 | 2014-05-15 | 三菱化学株式会社 | Organic electroluminescent element and method for manufacturing same |
WO2014089066A1 (en) * | 2012-12-03 | 2014-06-12 | The University Of Akron | An organic polymer photo device with broadband response and increased photo-responsitivity |
WO2015194359A1 (en) | 2014-06-20 | 2015-12-23 | コニカミノルタ株式会社 | Electroluminescent element design method, electroluminescent element manufactured using such design method, and electroluminescent element manufacturing method using such design method |
MX2017001147A (en) * | 2014-07-25 | 2017-07-13 | Avery Dennison Corp | Two-in-one translucent and colored film. |
CN105870353B (en) * | 2016-04-14 | 2018-04-27 | 京东方科技集团股份有限公司 | Organic electroluminescence device and preparation method thereof, display device |
EP3358638A4 (en) * | 2016-06-15 | 2019-01-16 | Kolon Industries, Inc. | Organic solar cell and method for manufacturing same |
TWI662730B (en) * | 2018-03-09 | 2019-06-11 | 謙華科技股份有限公司 | Thermal transfer film for preparing organic light emitting diode and preparation method thereof |
US20230276647A1 (en) * | 2020-07-30 | 2023-08-31 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device, light-emitting apparatus, light-emitting module, electronic device, and lighting device |
Citations (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5158829A (en) * | 1988-05-27 | 1992-10-27 | Ciba-Geigy Corporation | Electroactive ultra-thin layers |
US5247226A (en) * | 1991-04-19 | 1993-09-21 | Mitsubishi Kasei Corporation | Organic electroluminescent device |
US5281489A (en) * | 1990-03-16 | 1994-01-25 | Asashi Kasei Kogyo Kabushiki Kaisha | Electroluminescent element |
US5284779A (en) * | 1989-11-24 | 1994-02-08 | Semiconductor Energy Laboratory Co., Ltd. | Method of forming organic charge-transfer thin films |
US5521035A (en) * | 1994-07-11 | 1996-05-28 | Minnesota Mining And Manufacturing Company | Methods for preparing color filter elements using laser induced transfer of colorants with associated liquid crystal display device |
US5559400A (en) * | 1993-11-15 | 1996-09-24 | Hitachi, Ltd. | Variable wavelength luminescent device and control method therefor |
US5621131A (en) * | 1994-10-14 | 1997-04-15 | Hoechst Aktiengesellschaft | Conjugated polymers having spiro centers and their use as electroluminescence materials |
US5639896A (en) * | 1995-05-10 | 1997-06-17 | Bayer Aktiengesellschaft | Process for the preparation of N,N'-disubstituted 1,4-diaminoanthraquinones |
US5691098A (en) * | 1996-04-03 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Laser-Induced mass transfer imaging materials utilizing diazo compounds |
US5693446A (en) * | 1996-04-17 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Polarizing mass transfer donor element and method of transferring a polarizing mass transfer layer |
US5695907A (en) * | 1996-03-14 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Laser addressable thermal transfer imaging element and method |
US5708130A (en) * | 1995-07-28 | 1998-01-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
US5710097A (en) * | 1996-06-27 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Process and materials for imagewise placement of uniform spacers in flat panel displays |
US5725989A (en) * | 1996-04-15 | 1998-03-10 | Chang; Jeffrey C. | Laser addressable thermal transfer imaging element with an interlayer |
US5728801A (en) * | 1996-08-13 | 1998-03-17 | The Dow Chemical Company | Poly (arylamines) and films thereof |
US5747217A (en) * | 1996-04-03 | 1998-05-05 | Minnesota Mining And Manufacturing Company | Laser-induced mass transfer imaging materials and methods utilizing colorless sublimable compounds |
US5766827A (en) * | 1995-03-16 | 1998-06-16 | Minnesota Mining And Manufacturing Co. | Process of imaging black metal thermally imageable transparency elements |
US5840217A (en) * | 1994-04-07 | 1998-11-24 | Hoechst Aktiengesellschaft | Spiro compounds and their use as electroluminescence materials |
US5858562A (en) * | 1994-10-13 | 1999-01-12 | Nec Corporation | Organic thin film electroluminescent device |
US5863860A (en) * | 1995-01-26 | 1999-01-26 | Minnesota Mining And Manufacturing Company | Thermal transfer imaging |
US5869350A (en) * | 1991-02-27 | 1999-02-09 | The Regents Of The University Of California | Fabrication of visible light emitting diodes soluble semiconducting polymers |
US5897727A (en) * | 1996-09-20 | 1999-04-27 | Minnesota Mining And Manufacturing Company | Method for assembling layers with a transfer process using a crosslinkable adhesive layer |
US5900327A (en) * | 1996-03-04 | 1999-05-04 | Uniax Corporation | Polyfluorenes as materials for photoluminescence and electroluminescence |
US5929194A (en) * | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
US5998045A (en) * | 1997-07-03 | 1999-12-07 | International Business Machines Corporation | Polymeric light-emitting device |
US5998085A (en) * | 1996-07-23 | 1999-12-07 | 3M Innovative Properties | Process for preparing high resolution emissive arrays and corresponding articles |
US6030715A (en) * | 1997-10-09 | 2000-02-29 | The University Of Southern California | Azlactone-related dopants in the emissive layer of an OLED |
US6057048A (en) * | 1998-10-01 | 2000-05-02 | Xerox Corporation | Electroluminescent (EL) devices |
US6057067A (en) * | 1994-07-11 | 2000-05-02 | 3M Innovative Properties Company | Method for preparing integral black matrix/color filter elements |
US6121727A (en) * | 1997-04-04 | 2000-09-19 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
US6140009A (en) * | 1999-01-15 | 2000-10-31 | 3M Innovative Properties Company | Thermal transfer element for forming multilayer devices |
US6150043A (en) * | 1998-04-10 | 2000-11-21 | The Trustees Of Princeton University | OLEDs containing thermally stable glassy organic hole transporting materials |
US6169163B1 (en) * | 1995-07-28 | 2001-01-02 | The Dow Chemical Company | Fluorene-containing polymers and compounds useful in the preparation thereof |
US6221543B1 (en) * | 1999-05-14 | 2001-04-24 | 3M Innovatives Properties | Process for making active substrates for color displays |
US6228555B1 (en) * | 1999-12-28 | 2001-05-08 | 3M Innovative Properties Company | Thermal mass transfer donor element |
US6228543B1 (en) * | 1999-09-09 | 2001-05-08 | 3M Innovative Properties Company | Thermal transfer with a plasticizer-containing transfer layer |
US6242115B1 (en) * | 1997-09-08 | 2001-06-05 | The University Of Southern California | OLEDs containing thermally stable asymmetric charge carrier materials |
US6242152B1 (en) * | 2000-05-03 | 2001-06-05 | 3M Innovative Properties | Thermal transfer of crosslinked materials from a donor to a receptor |
US6294273B1 (en) * | 1998-06-09 | 2001-09-25 | Bayer Aktiengesellschaft | Electroluminescent assemblies containing N-alkyl-2,2′-imino-bis-(8-hydroxy-quinoline)-metal complexes |
US6566807B1 (en) * | 1998-12-28 | 2003-05-20 | Sharp Kabushiki Kaisha | Organic electroluminescent element and production method thereof |
US6573650B2 (en) * | 2000-02-23 | 2003-06-03 | Dai Nippon Printing Co., Ltd. | Electroluminescent device and process for producing the same |
US6690109B2 (en) * | 2001-08-13 | 2004-02-10 | Victor Company Of Japan, Ltd. | Organic electroluminescence element and manufacturing method thereof |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3016896B2 (en) * | 1991-04-08 | 2000-03-06 | パイオニア株式会社 | Organic electroluminescence device |
US5294870A (en) * | 1991-12-30 | 1994-03-15 | Eastman Kodak Company | Organic electroluminescent multicolor image display device |
JPH06215874A (en) * | 1993-01-20 | 1994-08-05 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
US5558904A (en) * | 1994-07-08 | 1996-09-24 | Xerox Corporation | Electroluminescent devices containing a conjugated polymer obtained via halogen precursor route chemistry |
TW293172B (en) * | 1994-12-09 | 1996-12-11 | At & T Corp | |
US5707745A (en) * | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
JP2931229B2 (en) * | 1995-02-13 | 1999-08-09 | 出光興産株式会社 | Organic electroluminescence device |
JP3334408B2 (en) * | 1995-03-01 | 2002-10-15 | 三菱化学株式会社 | Organic electroluminescent device and method of manufacturing the same |
JP3412076B2 (en) * | 1995-03-08 | 2003-06-03 | 株式会社リコー | Organic EL device |
EP0863931A2 (en) | 1995-12-01 | 1998-09-16 | Ciba SC Holding AG | Poly(9,9'-spiro-bisfluorenes), the production and use of same |
WO1997033193A2 (en) | 1996-02-23 | 1997-09-12 | The Dow Chemical Company | Cross-linkable or chain extendable polyarylpolyamines and films thereof |
US5705285A (en) * | 1996-09-03 | 1998-01-06 | Motorola, Inc. | Multicolored organic electroluminescent display |
GB9711237D0 (en) | 1997-06-02 | 1997-07-23 | Isis Innovation | Organomettallic Complexes |
US6592933B2 (en) * | 1997-10-15 | 2003-07-15 | Toray Industries, Inc. | Process for manufacturing organic electroluminescent device |
KR100610126B1 (en) | 1998-02-04 | 2006-08-09 | 메르크 파텐트 게엠베하 | Use of spiro compounds as laser dyes |
WO2000017911A1 (en) | 1998-09-24 | 2000-03-30 | Fed Corporation | Active matrix organic light emitting diode with doped organic layer having increased thickness |
GB9820805D0 (en) | 1998-09-25 | 1998-11-18 | Isis Innovation | Divalent lanthanide metal complexes |
JP2000195673A (en) | 1998-12-25 | 2000-07-14 | Sanyo Electric Co Ltd | Organic electroluminescent element and luminous element |
EP1144197B1 (en) * | 1999-01-15 | 2003-06-11 | 3M Innovative Properties Company | Thermal Transfer Method. |
US6461775B1 (en) | 1999-05-14 | 2002-10-08 | 3M Innovative Properties Company | Thermal transfer of a black matrix containing carbon black |
US6611096B1 (en) * | 1999-09-03 | 2003-08-26 | 3M Innovative Properties Company | Organic electronic devices having conducting self-doped polymer buffer layers |
US6521324B1 (en) | 1999-11-30 | 2003-02-18 | 3M Innovative Properties Company | Thermal transfer of microstructured layers |
JP2001250685A (en) * | 2000-03-07 | 2001-09-14 | Pioneer Electronic Corp | Light emission element and its manufacturing method |
US6485844B1 (en) | 2000-04-04 | 2002-11-26 | Honeywell International, Inc. | Thermal barrier coating having a thin, high strength bond coat |
US20020036291A1 (en) * | 2000-06-20 | 2002-03-28 | Parker Ian D. | Multilayer structures as stable hole-injecting electrodes for use in high efficiency organic electronic devices |
US20020031602A1 (en) * | 2000-06-20 | 2002-03-14 | Chi Zhang | Thermal treatment of solution-processed organic electroactive layer in organic electronic device |
JP2002083691A (en) * | 2000-09-06 | 2002-03-22 | Sharp Corp | Active matrix driven organic led display unit and its manufacturing method |
US6358664B1 (en) | 2000-09-15 | 2002-03-19 | 3M Innovative Properties Company | Electronically active primer layers for thermal patterning of materials for electronic devices |
US6855384B1 (en) * | 2000-09-15 | 2005-02-15 | 3M Innovative Properties Company | Selective thermal transfer of light emitting polymer blends |
US6485884B2 (en) * | 2001-04-27 | 2002-11-26 | 3M Innovative Properties Company | Method for patterning oriented materials for organic electronic displays and devices |
JP2002343564A (en) * | 2001-05-18 | 2002-11-29 | Sharp Corp | Transfer film and manufacturing method of organic electroluminescence element using the same |
US6699597B2 (en) * | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
EP1289015B1 (en) * | 2001-08-28 | 2012-05-23 | Konica Corporation | Multicolor light emission apparatus and manufacturing method thereof |
US6759146B2 (en) * | 2001-11-08 | 2004-07-06 | Xerox Corporation | Organic devices |
US7241512B2 (en) * | 2002-04-19 | 2007-07-10 | 3M Innovative Properties Company | Electroluminescent materials and methods of manufacture and use |
US20040004433A1 (en) * | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US7094902B2 (en) * | 2002-09-25 | 2006-08-22 | 3M Innovative Properties Company | Electroactive polymers |
-
2002
- 2002-06-26 US US10/183,717 patent/US20040004433A1/en not_active Abandoned
-
2003
- 2003-05-07 AU AU2003286999A patent/AU2003286999A1/en not_active Abandoned
- 2003-05-07 AT AT03777517T patent/ATE358336T1/en not_active IP Right Cessation
- 2003-05-07 CN CN038150581A patent/CN1666356A/en active Pending
- 2003-05-07 WO PCT/US2003/014466 patent/WO2004021463A2/en active IP Right Grant
- 2003-05-07 JP JP2004532564A patent/JP2005531915A/en active Pending
- 2003-05-07 CN CNA2008101440501A patent/CN101325247A/en active Pending
- 2003-05-07 EP EP03777517A patent/EP1518281B8/en not_active Expired - Lifetime
- 2003-05-07 MX MXPA04012432A patent/MXPA04012432A/en active IP Right Grant
- 2003-05-07 KR KR1020047021123A patent/KR101011428B1/en active IP Right Grant
- 2003-05-07 DE DE60312861T patent/DE60312861T2/en not_active Expired - Fee Related
- 2003-06-06 TW TW092115415A patent/TW200402248A/en unknown
- 2003-06-10 MY MYPI20032162A patent/MY135888A/en unknown
-
2005
- 2005-04-29 US US11/118,574 patent/US7166010B2/en not_active Expired - Lifetime
-
2006
- 2006-12-11 US US11/609,066 patent/US20070079927A1/en not_active Abandoned
-
2013
- 2013-02-21 US US13/773,533 patent/US20130164875A1/en not_active Abandoned
Patent Citations (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5158829A (en) * | 1988-05-27 | 1992-10-27 | Ciba-Geigy Corporation | Electroactive ultra-thin layers |
US5284779A (en) * | 1989-11-24 | 1994-02-08 | Semiconductor Energy Laboratory Co., Ltd. | Method of forming organic charge-transfer thin films |
US5281489A (en) * | 1990-03-16 | 1994-01-25 | Asashi Kasei Kogyo Kabushiki Kaisha | Electroluminescent element |
US5869350A (en) * | 1991-02-27 | 1999-02-09 | The Regents Of The University Of California | Fabrication of visible light emitting diodes soluble semiconducting polymers |
US5247226A (en) * | 1991-04-19 | 1993-09-21 | Mitsubishi Kasei Corporation | Organic electroluminescent device |
US5559400A (en) * | 1993-11-15 | 1996-09-24 | Hitachi, Ltd. | Variable wavelength luminescent device and control method therefor |
US5840217A (en) * | 1994-04-07 | 1998-11-24 | Hoechst Aktiengesellschaft | Spiro compounds and their use as electroluminescence materials |
US5521035A (en) * | 1994-07-11 | 1996-05-28 | Minnesota Mining And Manufacturing Company | Methods for preparing color filter elements using laser induced transfer of colorants with associated liquid crystal display device |
US6057067A (en) * | 1994-07-11 | 2000-05-02 | 3M Innovative Properties Company | Method for preparing integral black matrix/color filter elements |
US5858562A (en) * | 1994-10-13 | 1999-01-12 | Nec Corporation | Organic thin film electroluminescent device |
US5621131A (en) * | 1994-10-14 | 1997-04-15 | Hoechst Aktiengesellschaft | Conjugated polymers having spiro centers and their use as electroluminescence materials |
US5863860A (en) * | 1995-01-26 | 1999-01-26 | Minnesota Mining And Manufacturing Company | Thermal transfer imaging |
US5766827A (en) * | 1995-03-16 | 1998-06-16 | Minnesota Mining And Manufacturing Co. | Process of imaging black metal thermally imageable transparency elements |
US5639896A (en) * | 1995-05-10 | 1997-06-17 | Bayer Aktiengesellschaft | Process for the preparation of N,N'-disubstituted 1,4-diaminoanthraquinones |
US6169163B1 (en) * | 1995-07-28 | 2001-01-02 | The Dow Chemical Company | Fluorene-containing polymers and compounds useful in the preparation thereof |
US5708130A (en) * | 1995-07-28 | 1998-01-13 | 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 |
US5900327A (en) * | 1996-03-04 | 1999-05-04 | Uniax Corporation | Polyfluorenes as materials for photoluminescence and electroluminescence |
US5695907A (en) * | 1996-03-14 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Laser addressable thermal transfer imaging element and method |
US5747217A (en) * | 1996-04-03 | 1998-05-05 | Minnesota Mining And Manufacturing Company | Laser-induced mass transfer imaging materials and methods utilizing colorless sublimable compounds |
US5691098A (en) * | 1996-04-03 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Laser-Induced mass transfer imaging materials utilizing diazo compounds |
US5981136A (en) * | 1996-04-15 | 1999-11-09 | 3M Innovative Properties Company | Laser addressable thermal transfer imaging element with an interlayer |
US5725989A (en) * | 1996-04-15 | 1998-03-10 | Chang; Jeffrey C. | Laser addressable thermal transfer imaging element with an interlayer |
US6270934B1 (en) * | 1996-04-15 | 2001-08-07 | 3M Innovative Properties Company | Laser addressable thermal transfer imaging element with an interlayer |
US6099994A (en) * | 1996-04-15 | 2000-08-08 | 3M Innovative Properties Company | Laser addressable thermal transfer imaging element with an interlayer |
US6190826B1 (en) * | 1996-04-15 | 2001-02-20 | 3M Innovative Properties Company | Laser addressable thermal transfer imaging element with an interlayer |
US5693446A (en) * | 1996-04-17 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Polarizing mass transfer donor element and method of transferring a polarizing mass transfer layer |
US5976698A (en) * | 1996-06-27 | 1999-11-02 | 3M Innovative Properties Company | Process and materials for imagewise placement of uniform spacers in flat panel displays |
US5710097A (en) * | 1996-06-27 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Process and materials for imagewise placement of uniform spacers in flat panel displays |
US5998085A (en) * | 1996-07-23 | 1999-12-07 | 3M Innovative Properties | Process for preparing high resolution emissive arrays and corresponding articles |
US5728801A (en) * | 1996-08-13 | 1998-03-17 | The Dow Chemical Company | Poly (arylamines) and films thereof |
US5897727A (en) * | 1996-09-20 | 1999-04-27 | Minnesota Mining And Manufacturing Company | Method for assembling layers with a transfer process using a crosslinkable adhesive layer |
US6121727A (en) * | 1997-04-04 | 2000-09-19 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
US5998045A (en) * | 1997-07-03 | 1999-12-07 | International Business Machines Corporation | Polymeric light-emitting device |
US6242115B1 (en) * | 1997-09-08 | 2001-06-05 | The University Of Southern California | OLEDs containing thermally stable asymmetric charge carrier materials |
US6030715A (en) * | 1997-10-09 | 2000-02-29 | The University Of Southern California | Azlactone-related dopants in the emissive layer of an OLED |
US6150043A (en) * | 1998-04-10 | 2000-11-21 | The Trustees Of Princeton University | OLEDs containing thermally stable glassy organic hole transporting materials |
US6294273B1 (en) * | 1998-06-09 | 2001-09-25 | Bayer Aktiengesellschaft | Electroluminescent assemblies containing N-alkyl-2,2′-imino-bis-(8-hydroxy-quinoline)-metal complexes |
US6057048A (en) * | 1998-10-01 | 2000-05-02 | Xerox Corporation | Electroluminescent (EL) devices |
US6566807B1 (en) * | 1998-12-28 | 2003-05-20 | Sharp Kabushiki Kaisha | Organic electroluminescent element and production method thereof |
US6221553B1 (en) * | 1999-01-15 | 2001-04-24 | 3M Innovative Properties Company | Thermal transfer element for forming multilayer devices |
US6214520B1 (en) * | 1999-01-15 | 2001-04-10 | 3M Innovative Properties Company | Thermal transfer element for forming multilayer devices |
US6194119B1 (en) * | 1999-01-15 | 2001-02-27 | 3M Innovative Properties Company | Thermal transfer element and process for forming organic electroluminescent devices |
US6270944B1 (en) * | 1999-01-15 | 2001-08-07 | 3M Innovative Properties Company | Thermal transfer element for forming multilayers devices |
US6140009A (en) * | 1999-01-15 | 2000-10-31 | 3M Innovative Properties Company | Thermal transfer element for forming multilayer devices |
US6221543B1 (en) * | 1999-05-14 | 2001-04-24 | 3M Innovatives Properties | Process for making active substrates for color displays |
US6228543B1 (en) * | 1999-09-09 | 2001-05-08 | 3M Innovative Properties Company | Thermal transfer with a plasticizer-containing transfer layer |
US6228555B1 (en) * | 1999-12-28 | 2001-05-08 | 3M Innovative Properties Company | Thermal mass transfer donor element |
US6573650B2 (en) * | 2000-02-23 | 2003-06-03 | Dai Nippon Printing Co., Ltd. | Electroluminescent device and process for producing the same |
US6242152B1 (en) * | 2000-05-03 | 2001-06-05 | 3M Innovative Properties | Thermal transfer of crosslinked materials from a donor to a receptor |
US6690109B2 (en) * | 2001-08-13 | 2004-02-10 | Victor Company Of Japan, Ltd. | Organic electroluminescence element and manufacturing method thereof |
Cited By (178)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6867756B2 (en) * | 2000-11-23 | 2005-03-15 | Lg. Philips Lcd Co., Ltd. | Electroluminescence display device |
US20020060654A1 (en) * | 2000-11-23 | 2002-05-23 | Lg.Philips Lcd Co., Ltd. | Electroluminescence display device |
US20070079927A1 (en) * | 2002-06-26 | 2007-04-12 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20050191776A1 (en) * | 2002-06-26 | 2005-09-01 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US7166010B2 (en) | 2002-06-26 | 2007-01-23 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20040146744A1 (en) * | 2002-07-31 | 2004-07-29 | Satoshi Seo | Material for an electroluminescence element and electroluminescence element using the same |
US20080012482A1 (en) * | 2002-07-31 | 2008-01-17 | Semiconductor Energy Laboratory Co., Ltd. | Material For An Electroluminescence Element And Electroluminescence Element Using The Same |
US8519092B2 (en) | 2002-08-28 | 2013-08-27 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US20040109955A1 (en) * | 2002-08-28 | 2004-06-10 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US20100133997A1 (en) * | 2002-08-28 | 2010-06-03 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US7772360B2 (en) * | 2002-08-28 | 2010-08-10 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US8263735B2 (en) | 2002-08-28 | 2012-09-11 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
US7321195B2 (en) * | 2002-11-06 | 2008-01-22 | Lg.Philips Lcd Co., Ltd. | Organic electro-luminescent device having polymer emission layer |
US20040085015A1 (en) * | 2002-11-06 | 2004-05-06 | Lg.Philips Lcd Co., Ltd. | Oraganic electro-luminescent device having polymer emission layer and method for fabricating the same |
US8173453B2 (en) | 2002-12-19 | 2012-05-08 | 3M Innovative Properties Company | Laser patterning of encapsulated organic light emitting diodes |
US20080160789A1 (en) * | 2002-12-19 | 2008-07-03 | 3M Innovative Properties Company | Laser patterning of encapsulated organic light emitting diodes |
US6869699B2 (en) * | 2003-03-18 | 2005-03-22 | Eastman Kodak Company | P-type materials and mixtures for electronic devices |
US20040183066A1 (en) * | 2003-03-18 | 2004-09-23 | Eastman Kodak Company | P-type materials and mixtures for electronic devices |
US20060099448A1 (en) * | 2003-04-28 | 2006-05-11 | Zheng-Hong Lu | Top light-emitting devices with fullerene layer |
US20050082523A1 (en) * | 2003-06-26 | 2005-04-21 | Blanchet-Fincher Graciela B. | Methods for forming patterns on a filled dielectric material on substrates |
US7259443B2 (en) * | 2003-06-26 | 2007-08-21 | E.I. Du Pont De Nemours And Company | Methods for forming patterns on a filled dielectric material on substrates |
US20080096135A1 (en) * | 2003-06-26 | 2008-04-24 | Blanchet-Fincher Graciela B | Methods for forming patterns of a filled dielectric material on substrates |
US8716697B2 (en) | 2004-02-20 | 2014-05-06 | E I Du Pont De Nemours And Company | Electronic devices made with crosslinkable compounds and copolymers |
US20080132622A1 (en) * | 2004-02-20 | 2008-06-05 | Norman Herron | Electronic devices made with crosslinkable compounds and copolymers |
US7365230B2 (en) | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
US20050184287A1 (en) * | 2004-02-20 | 2005-08-25 | Norman Herron | Cross-linkable polymers and electronic devices made with such polymers |
US8236990B2 (en) | 2004-03-31 | 2012-08-07 | E I Du Pont De Nemours And Company | Triarylamine compounds, compositions and uses therefor |
US20050282307A1 (en) * | 2004-06-21 | 2005-12-22 | Daniels John J | Particulate for organic and inorganic light active devices and methods for fabricating the same |
US20060022585A1 (en) * | 2004-08-02 | 2006-02-02 | Xerox Corporation | OLEDs having improved luminance stability |
EP1624503A3 (en) * | 2004-08-02 | 2007-11-14 | LG. Philips LCD Co., Ltd. | OLEDs having improved luminance stability |
EP1624503A2 (en) | 2004-08-02 | 2006-02-08 | LG. Philips LCD Co., Ltd. | OLEDs having improved luminance stability |
US7449831B2 (en) | 2004-08-02 | 2008-11-11 | Lg Display Co., Ltd. | OLEDs having inorganic material containing anode capping layer |
US20060022590A1 (en) * | 2004-08-02 | 2006-02-02 | Xerox Corporation | OLEDs having inorganic material containing anode capping layer |
EP3057152A1 (en) | 2004-08-02 | 2016-08-17 | LG Display Co., Ltd. | Oleds having inorganic material containing anode capping layer |
US7449830B2 (en) | 2004-08-02 | 2008-11-11 | Lg Display Co., Ltd. | OLEDs having improved luminance stability |
US20060182993A1 (en) * | 2004-08-10 | 2006-08-17 | Mitsubishi Chemical Corporation | Compositions for organic electroluminescent device and organic electroluminescent device |
US20090309070A1 (en) * | 2004-08-10 | 2009-12-17 | Mitsubishi Chemical Corporation | Compositions for organic electroluminescent device and organic electroluminescent device |
US7560862B2 (en) * | 2004-10-22 | 2009-07-14 | Eastman Kodak Company | White OLEDs with a color-compensated electroluminescent unit |
US20060087225A1 (en) * | 2004-10-22 | 2006-04-27 | Eastman Kodak Company | White OLEDs with a color-compensated electroluminescent unit |
US8339026B2 (en) | 2004-11-15 | 2012-12-25 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode and method of making the same |
US7923911B2 (en) | 2004-11-15 | 2011-04-12 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode and method of making the same |
US20110159610A1 (en) * | 2004-11-15 | 2011-06-30 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode and method of making the same |
US20090134790A1 (en) * | 2004-11-15 | 2009-05-28 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode & method of making the same |
US20060103299A1 (en) * | 2004-11-15 | 2006-05-18 | The Hong Kong University Of Science And Technology | Polycrystalline silicon as an electrode for a light emitting diode & method of making the same |
US7659543B2 (en) * | 2004-11-17 | 2010-02-09 | Samsung Mobile Display Co., Ltd. | Organic light emitting display and method of fabricating the same |
US20060102911A1 (en) * | 2004-11-17 | 2006-05-18 | Seoung-Yoon Ryu | Organic light emitting display and method of fabricating the same |
US7315042B2 (en) | 2004-11-18 | 2008-01-01 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compounds |
US20060102893A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compoounds |
US20060105199A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Electroluminescent devices containing trans-1,2-bis(acenyl)ethylene compounds |
US20070216292A1 (en) * | 2004-12-06 | 2007-09-20 | Satoshi Seo | Composite Material Including organic Compound And Inorganic Compound Light-Emitting Element And Light-Emitting Device Using The Composite Compound, And Manufacturing Method Of The Light-Emitting Element |
US20080003455A1 (en) * | 2004-12-08 | 2008-01-03 | Fuji Electric Holdings Co., Ltd. | Organic El Device |
US20080154005A1 (en) * | 2005-01-31 | 2008-06-26 | Semiconductor Energy Laboratory Co., Ltd. | Hole-Injecting Material, Material for Light-Emitting Element, Light-Emitting Element, Organic Compound, Monomer, and Monomer Mixture |
WO2006080553A1 (en) * | 2005-01-31 | 2006-08-03 | Semiconductor Energy Laboratory Co., Ltd. | Hole-injecting material, material for light-emitting element, light-emitting element, organic compound, monomer, and monomer mixture |
JP2006237592A (en) * | 2005-01-31 | 2006-09-07 | Semiconductor Energy Lab Co Ltd | Hole-injecting material, light emitting device material, light emitting device, organic compound, monomer and monomer mixture |
KR101288586B1 (en) * | 2005-01-31 | 2013-07-22 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Hole-injecting material, material for light-emitting element, light-emitting element, organic compound, monomer, and monomer mixture |
US8053973B2 (en) | 2005-02-15 | 2011-11-08 | Pioneer Corporation | Film forming composition and organic electroluminescent device |
US20090072714A1 (en) * | 2005-03-23 | 2009-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Composite Material, Material for Light-Emitting Element, Light-Emitting Element, Light-Emitting Device and Electronic Device |
US8986854B2 (en) | 2005-03-23 | 2015-03-24 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, material for light-emitting element, light-emitting element, light-emitting device and electronic device |
US7977865B2 (en) | 2005-03-23 | 2011-07-12 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, material for light-emitting element, light-emitting element, light-emitting device and electronic device |
US20110227051A1 (en) * | 2005-03-23 | 2011-09-22 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, material for light-emitting element, light-emitting element, light-emitting device and electronic device |
US7645478B2 (en) | 2005-03-31 | 2010-01-12 | 3M Innovative Properties Company | Methods of making displays |
US20060228974A1 (en) * | 2005-03-31 | 2006-10-12 | Theiss Steven D | Methods of making displays |
US20060251919A1 (en) * | 2005-05-04 | 2006-11-09 | Xerox Corporation | Organic light emitting devices |
US7777407B2 (en) | 2005-05-04 | 2010-08-17 | Lg Display Co., Ltd. | Organic light emitting devices comprising a doped triazine electron transport layer |
US8487527B2 (en) | 2005-05-04 | 2013-07-16 | Lg Display Co., Ltd. | Organic light emitting devices |
US20060261731A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Stacked oled structure |
US7795806B2 (en) | 2005-05-20 | 2010-09-14 | Lg Display Co., Ltd. | Reduced reflectance display devices containing a thin-layer metal-organic mixed layer (MOML) |
US20060263629A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Intermediate electrodes for stacked OLEDs |
US20060263628A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Display device with metal-organic mixed layer anodes |
US7728517B2 (en) | 2005-05-20 | 2010-06-01 | Lg Display Co., Ltd. | Intermediate electrodes for stacked OLEDs |
US20060263593A1 (en) * | 2005-05-20 | 2006-11-23 | Xerox Corporation | Display devices with light absorbing metal nonoparticle layers |
US7811679B2 (en) | 2005-05-20 | 2010-10-12 | Lg Display Co., Ltd. | Display devices with light absorbing metal nanoparticle layers |
US7750561B2 (en) | 2005-05-20 | 2010-07-06 | Lg Display Co., Ltd. | Stacked OLED structure |
US7943244B2 (en) | 2005-05-20 | 2011-05-17 | Lg Display Co., Ltd. | Display device with metal-organic mixed layer anodes |
US20060284533A1 (en) * | 2005-06-21 | 2006-12-21 | Au Optronics Corp. | Organic electroluminescent device |
US7812359B2 (en) * | 2005-06-21 | 2010-10-12 | Au Optronics Corp. | Organic electroluminescent device |
EP1753047A3 (en) * | 2005-08-08 | 2011-01-26 | OSRAM Opto Semiconductors GmbH | Solution processed crosslinkable hole injection and hole transport polymers for oleds |
EP1753047A2 (en) * | 2005-08-08 | 2007-02-14 | Osram Opto Semiconductors GmbH | Solution processed crosslinkable hole injection and hole transport polymers for oleds |
EP1923929A4 (en) * | 2005-09-08 | 2010-09-29 | Idemitsu Kosan Co | Organic electroluminescence device |
US20070054151A1 (en) * | 2005-09-08 | 2007-03-08 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US8039121B2 (en) | 2005-09-08 | 2011-10-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
JP4909900B2 (en) * | 2005-09-08 | 2012-04-04 | 出光興産株式会社 | Organic electroluminescence device |
EP1923929A1 (en) * | 2005-09-08 | 2008-05-21 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US8377575B2 (en) | 2005-09-08 | 2013-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US20070126347A1 (en) * | 2005-12-01 | 2007-06-07 | Eastman Kodak Company | OLEDS with improved efficiency |
WO2007067407A3 (en) * | 2005-12-05 | 2007-11-22 | Gen Electric | A transparent electrode for organic electronic devices |
US20070128465A1 (en) * | 2005-12-05 | 2007-06-07 | General Electric Company | Transparent electrode for organic electronic devices |
TWI481088B (en) * | 2005-12-05 | 2015-04-11 | Gen Electric | A transparent electrode for organic electronic devices |
WO2007067407A2 (en) * | 2005-12-05 | 2007-06-14 | General Electric Company | A transparent electrode for organic electronic devices |
US20070275624A1 (en) * | 2005-12-14 | 2007-11-29 | Fuji Electric Holdings Co., Ltd. | Method of the manufacturing an organic EL display |
US7855393B2 (en) | 2006-02-03 | 2010-12-21 | Tridonic Optoelectronics Gmbh | Light emitting device with a non-activated luminescent material |
US20090294788A1 (en) * | 2006-02-03 | 2009-12-03 | Tridonic Optoelectronics Gmbh | Light emitting device with a non-activated luminescent material |
WO2007087954A1 (en) * | 2006-02-03 | 2007-08-09 | Tridonicatco Optoelectronics Gmbh | Light emitting device with a non-activated luminescent material |
US9701899B2 (en) | 2006-03-07 | 2017-07-11 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
US10633582B2 (en) | 2006-03-07 | 2020-04-28 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, and other products |
US10393940B2 (en) | 2006-03-07 | 2019-08-27 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
US9874674B2 (en) | 2006-03-07 | 2018-01-23 | Samsung Electronics Co., Ltd. | Compositions, optical component, system including an optical component, devices, and other products |
US20070241665A1 (en) * | 2006-04-12 | 2007-10-18 | Matsushita Electric Industrial Co., Ltd. | Organic electroluminescent element, and manufacturing method thereof, as well as display device and exposure apparatus using the same |
US20080071049A1 (en) * | 2006-08-24 | 2008-03-20 | Radu Nora S | Hole transport polymers |
US8487055B2 (en) | 2006-08-24 | 2013-07-16 | E I Du Pont De Nemours And Company | Hole transport polymers |
US8242223B2 (en) | 2006-08-24 | 2012-08-14 | E I Du Pont De Nemours And Company | Hole transport polymers |
US8465848B2 (en) | 2006-12-29 | 2013-06-18 | E I Du Pont De Nemours And Company | Benzofluorenes for luminescent applications |
US20080160348A1 (en) * | 2006-12-29 | 2008-07-03 | Eric Maurice Smith | Benzofluorenes for luminescent applications |
US20090001878A1 (en) * | 2007-04-03 | 2009-01-01 | Tsinghua University | Organic electroluminescent device |
US20080254306A1 (en) * | 2007-04-10 | 2008-10-16 | Yong-Tak Kim | Method of manufacturing organic light-emitting device and organic light-emitting device manufactured using the method |
US8241762B2 (en) | 2007-06-01 | 2012-08-14 | E I Du Pont De Nemours And Company | Charge transport materials for luminescent applications |
US20080297040A1 (en) * | 2007-06-01 | 2008-12-04 | Weishi Wu | Charge transport materials for luminescent applications |
US8460802B2 (en) | 2007-06-01 | 2013-06-11 | E I Du Pont De Nemours And Company | Charge transport materials for luminescent applications |
US9815996B2 (en) | 2007-06-25 | 2017-11-14 | Samsung Electronics Co., Ltd. | Compositions and methods including depositing nanomaterial |
US11866598B2 (en) | 2007-06-25 | 2024-01-09 | Samsung Electronics Co., Ltd. | Compositions and methods including depositing nanomaterial |
US11472979B2 (en) | 2007-06-25 | 2022-10-18 | Samsung Electronics Co., Ltd. | Compositions and methods including depositing nanomaterial |
US11214701B2 (en) | 2007-06-25 | 2022-01-04 | Samsung Electronics Co., Ltd. | Compositions and methods including depositing nanomaterial |
US20100187518A1 (en) * | 2007-07-12 | 2010-07-29 | Sumitomo Chemical Company, Limited | Method of producing organic light emitting device |
US20090015757A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode lighting devices |
US8298032B2 (en) | 2007-07-13 | 2012-10-30 | 3M Innovative Properties Company | Methods for providing light extraction films on organic light emitting diode devices |
US20090015142A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode display devices |
US20110229992A1 (en) * | 2007-07-13 | 2011-09-22 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode lighting devices |
US8179034B2 (en) | 2007-07-13 | 2012-05-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode display and lighting devices |
US8008853B2 (en) * | 2007-08-21 | 2011-08-30 | Fujifilm Corporation | Organic electroluminescent display |
US20090051277A1 (en) * | 2007-08-21 | 2009-02-26 | Katsumi Inoue | Organic electroluminescent display |
US8652655B2 (en) | 2007-11-19 | 2014-02-18 | E I Du Pont De Nemours And Company | Electroactive materials |
US8889269B2 (en) | 2007-11-19 | 2014-11-18 | E I Du Pont De Nemours And Company | Electroactive materials |
US20100187513A1 (en) * | 2008-04-23 | 2010-07-29 | Panasonic Corporation | Organic electroluminescence element |
US8178870B2 (en) | 2008-04-23 | 2012-05-15 | Panasonic Corporation | Organic electroluminescence element |
US8343381B1 (en) * | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
US9574084B2 (en) | 2008-05-16 | 2017-02-21 | E I Du Pont De Nemours And Company | Hole transport composition |
US20100110551A1 (en) * | 2008-10-31 | 2010-05-06 | 3M Innovative Properties Company | Light extraction film with high index backfill layer and passivation layer |
US8551624B2 (en) | 2008-12-01 | 2013-10-08 | E I Du Pont De Nemours And Company | Electroactive materials |
US20100213825A1 (en) * | 2008-12-01 | 2010-08-26 | Park Kyung-Ho | Electroactive materials |
US20100187506A1 (en) * | 2008-12-01 | 2010-07-29 | Park Kyung-Ho | Electroactive materials |
US9099653B2 (en) | 2008-12-01 | 2015-08-04 | E I Du Pont De Nemours And Company | Electroactive materials |
US8420232B2 (en) | 2008-12-04 | 2013-04-16 | E I Du Pont De Nemours And Company | Binaphthyl-arylamine polymers |
US20100187507A1 (en) * | 2008-12-04 | 2010-07-29 | Park Kyung-Ho | Electroactive materials |
US20110037056A1 (en) * | 2008-12-12 | 2011-02-17 | E. I. Du Pont De Nemours And Company | Photoactive composition and electronic device made with the composition |
US8249409B2 (en) | 2008-12-17 | 2012-08-21 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
US7957621B2 (en) | 2008-12-17 | 2011-06-07 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
US20110200293A1 (en) * | 2008-12-17 | 2011-08-18 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
US20100150513A1 (en) * | 2008-12-17 | 2010-06-17 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
US8890131B2 (en) | 2009-02-27 | 2014-11-18 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
US20100252819A1 (en) * | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
US8497495B2 (en) | 2009-04-03 | 2013-07-30 | E I Du Pont De Nemours And Company | Electroactive materials |
WO2010115767A1 (en) | 2009-04-08 | 2010-10-14 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
US9067942B2 (en) | 2009-04-08 | 2015-06-30 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
US20110095273A1 (en) * | 2009-09-29 | 2011-04-28 | E. I. Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
US8431245B2 (en) | 2009-09-29 | 2013-04-30 | E. I. Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
US8937300B2 (en) * | 2009-10-19 | 2015-01-20 | E I Du Pont De Nemours And Company | Triarylamine compounds for use in organic light-emitting diodes |
US8648333B2 (en) * | 2009-10-19 | 2014-02-11 | E I Du Pont De Nemours And Company | Triarylamine compounds for use in organic light-emitting diodes |
US20110253985A1 (en) * | 2009-10-19 | 2011-10-20 | E. I. Du Pont De Nemours And Company | Triarylamine compounds for electronic applications |
US20110253986A1 (en) * | 2009-10-19 | 2011-10-20 | E. I. Du Pont De Nemours And Company | Triarylamine compounds for electronic applications |
US9496506B2 (en) | 2009-10-29 | 2016-11-15 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
US20130048973A1 (en) * | 2010-04-06 | 2013-02-28 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Organic Light-Emitting Diode Comprising At Least Two Electroluminescent Layers |
US8735879B2 (en) * | 2010-04-06 | 2014-05-27 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Organic light-emitting diode comprising at least two electroluminescent layers |
WO2012041849A1 (en) | 2010-09-29 | 2012-04-05 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
US9293716B2 (en) | 2010-12-20 | 2016-03-22 | Ei Du Pont De Nemours And Company | Compositions for electronic applications |
US9431145B2 (en) | 2011-05-26 | 2016-08-30 | Neudrive Limited | Transistors and methods for making them |
US9406886B2 (en) * | 2011-05-26 | 2016-08-02 | Neudrive Limited | Semiconductor compounds |
US20140114040A1 (en) * | 2011-05-26 | 2014-04-24 | Peakdale Molecular Limited | Semiconductor compounds |
US10121970B2 (en) | 2011-05-26 | 2018-11-06 | Wuhan Xinqu Chuangrou Optoelectronics Technology Co., Ltd. | Transistors and methods for making them |
WO2012175530A1 (en) | 2011-06-22 | 2012-12-27 | Basf Se | Diketopyrrolopyrrole oligomers for use in organic semiconductor devices |
WO2013022792A3 (en) * | 2011-08-08 | 2013-05-02 | Quarkstar Llc | Method and apparatus for coupling light-emitting elements with light-converting material |
US10707435B2 (en) | 2011-08-08 | 2020-07-07 | Quarkstar Llc | Method and apparatus for coupling light-emitting elements with light-converting material |
US9034674B2 (en) | 2011-08-08 | 2015-05-19 | Quarkstar Llc | Method and apparatus for coupling light-emitting elements with light-converting material |
WO2013030325A1 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
US9209412B2 (en) | 2011-09-02 | 2015-12-08 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
US9929325B2 (en) | 2012-06-05 | 2018-03-27 | Samsung Electronics Co., Ltd. | Lighting device including quantum dots |
US20160301022A1 (en) * | 2013-07-03 | 2016-10-13 | Corning Precision Materials Co., Ltd. | Substrate for photoelectric device and photoelectric device comprising same |
US9960373B2 (en) * | 2013-07-03 | 2018-05-01 | Corning Precision Materials Co., Ltd. | Substrate for photoelectric device and photoelectric device comprising same |
US10193075B2 (en) | 2014-03-14 | 2019-01-29 | Nissan Chemical Industries, Ltd. | Aniline derivative and use thereof |
US9318715B2 (en) * | 2014-05-21 | 2016-04-19 | E I Du Point De Nemours And Company | Hole transport composition without luminance quenching |
WO2016028906A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
US10297755B2 (en) | 2014-08-21 | 2019-05-21 | Dow Global Technologies Llc | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
US10256410B2 (en) | 2014-08-21 | 2019-04-09 | Dow Global Technologies Llc | Compositions comprising oxygen substituted benzocyclobutenes and dienophiles, and electronic devices containing the same |
EP3413370A1 (en) | 2014-08-21 | 2018-12-12 | Dow Global Technologies Llc | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
US9793485B2 (en) | 2014-08-21 | 2017-10-17 | Dow Global Technologies Llc | Benzocyclobutenes derived compositions, and electronic devices containing the same |
WO2016028902A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Compositions containing benzocyclobutene substituted carbazoles, and electronic devices containing the same |
Also Published As
Publication number | Publication date |
---|---|
US20070079927A1 (en) | 2007-04-12 |
CN101325247A (en) | 2008-12-17 |
EP1518281A2 (en) | 2005-03-30 |
US7166010B2 (en) | 2007-01-23 |
TW200402248A (en) | 2004-02-01 |
CN1666356A (en) | 2005-09-07 |
KR101011428B1 (en) | 2011-01-28 |
EP1518281B8 (en) | 2007-09-12 |
JP2005531915A (en) | 2005-10-20 |
EP1518281B1 (en) | 2007-03-28 |
WO2004021463A3 (en) | 2004-07-29 |
MY135888A (en) | 2008-07-31 |
WO2004021463A2 (en) | 2004-03-11 |
AU2003286999A8 (en) | 2004-03-19 |
US20050191776A1 (en) | 2005-09-01 |
MXPA04012432A (en) | 2005-04-19 |
DE60312861D1 (en) | 2007-05-10 |
US20130164875A1 (en) | 2013-06-27 |
AU2003286999A1 (en) | 2004-03-19 |
KR20050019791A (en) | 2005-03-03 |
ATE358336T1 (en) | 2007-04-15 |
DE60312861T2 (en) | 2008-01-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7166010B2 (en) | Buffer layers for organic electroluminescent devices and methods of manufacture and use | |
US6699597B2 (en) | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein | |
US6555840B1 (en) | Charge-transport structures | |
US20030224205A1 (en) | Electroluminescent materials and methods of manufacture and use | |
US20040062947A1 (en) | Organic electroluminescent compositions | |
US20080054794A1 (en) | Organic Electroluminescence Device, Image Display Apparatus and Lighting Apparatus Including the Same, Charge Transport Material and Charge Transport Layer Forming Ink Including the Same | |
US20060008577A1 (en) | Method and materials for patterning of a polymerizable, amorphous matrix with electrically active material disposed therein | |
US20050147849A1 (en) | Thermal transfer of light-emitting dendrimers | |
JP2008525578A (en) | Hole transport layer for organic electroluminescent devices | |
JP2014165261A (en) | Organic light-emitting display device and manufacturing method therefor |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: 3M INNOVATIVE PROPERTIES COMPANY, MINNESOTA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LAMANSKY, SERGEY A.;NIRMAL, MANOJ;MCCORMICK, FRED B.;AND OTHERS;REEL/FRAME:013072/0388 Effective date: 20020626 |
|
AS | Assignment |
Owner name: 3M INNOVATIVE PROPERTIES COMPANY, MINNESOTA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LAMANSKY, SERGEY;NIRMAL, MANOJ;MCCORMICK, FRED B.;AND OTHERS;REEL/FRAME:013479/0083 Effective date: 20020626 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |