JP5636288B2 - 白色発光材料 - Google Patents
白色発光材料 Download PDFInfo
- Publication number
- JP5636288B2 JP5636288B2 JP2010543564A JP2010543564A JP5636288B2 JP 5636288 B2 JP5636288 B2 JP 5636288B2 JP 2010543564 A JP2010543564 A JP 2010543564A JP 2010543564 A JP2010543564 A JP 2010543564A JP 5636288 B2 JP5636288 B2 JP 5636288B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- light emitting
- group
- polymer chain
- repeat unit
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000463 material Substances 0.000 title claims description 61
- 229920000642 polymer Polymers 0.000 claims description 134
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000003086 colorant Substances 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 108010043121 Green Fluorescent Proteins Proteins 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 46
- 239000003446 ligand Substances 0.000 description 19
- 125000001072 heteroaryl group Chemical group 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 238000010129 solution processing Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002503 iridium Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- -1 poly (arylene vinylenes Chemical class 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001194 electroluminescence spectrum Methods 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000412 polyarylene Polymers 0.000 description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical class C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- PJHPFAFEJNBIDC-UHFFFAOYSA-N 1-(4-bromophenyl)piperazine Chemical compound C1=CC(Br)=CC=C1N1CCNCC1 PJHPFAFEJNBIDC-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- SCXBFXGVOQYURB-UHFFFAOYSA-N 2-phenyl-1h-isoquinoline Chemical class C1=CC2=CC=CC=C2CN1C1=CC=CC=C1 SCXBFXGVOQYURB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910015711 MoOx Inorganic materials 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019897 RuOx Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
− フルオレン繰り返し単位のホモポリマー、例えば、9,9−ジアルキルフルオレン−2,7−ジイルのホモポリマーなどは、電子輸送を提供するために利用することができる。
− トリアリールアミン繰り返し単位を含むコポリマー、特に、式2で示す繰り返し単位を含むコポリマーは、正孔輸送を提供するために利用することができ:
これらのポリマーの好ましい調製方法は、例えば、WO00/53656に記載されるSuzuki重合、および例えば、T.Yamamoto,“Electrically Conducting And Thermally Stable π−Conjugated Poly(arylene)s Prepared by Organometallic Processes”,Progress in Polymer Science,1993,17,1153−1205に記載されるYamamoto重合である。これらの重合技術は両方とも、金属錯体触媒の金属原子がアリール基とモノマーの脱離基との間に挿入される「金属挿入」によって行われる。Yamamoto重合の場合は、ニッケル錯体触媒が使用され、Suzuki重合の場合は、パラジウム錯体触媒が使用される。
単一のポリマーまたは複数のポリマーを溶液から堆積させて、層5を形成することができる。ポリアリーレン、特にポリフルオレンに適切な溶媒としては、トルエンやキシレンなどのモノまたはポリ−アルキルベンゼンが挙げられる。特に好ましい溶液堆積技術は、スピンコーティングおよびインクジェット印刷である。
ML1 qL2 rL3 s
22
式中、Mは金属であり、L1、L2、およびL3の各々は、配位基であり、qは、整数であり、rおよびsは、それぞれ独立に、0または整数であり、和(a.q)+(b.r)+(c.s)は、Mにおいて利用可能な配位部位(coordination site)の数に等しく、aは、L1の配位部位の数であり、bは、L2の配位部位の数であり、cは、L3の配位部位の数である。
− セリウム、サマリウム、ユウロピウム、テルビウム、ジスプロシウム、ツリウム、エルビウム、およびネオジムなどのランタニド金属;ならびに
− d−ブロック金属、特に、2列および3列のもの、すなわち、元素39〜48および72〜80、特に、ルテニウム、ロジウム、パラジウム、レニウム、オスミウム、イリジウム、白金、および金。
Claims (25)
- 脱離基を有するモノマーを金属触媒を用いて重合させ、得られたポリマーをモノブロミド燐光性エミッタエンドキャッピング基を使用してエンドキャップするステップを含む、発光ポリマー鎖と少なくとも1個の発光エンドキャッピング基とを有するポリマーを含む白色発光材料を作製する方法。
- 前記材料が、発光ポリマー鎖と少なくとも1個の発光エンドキャッピング基とを有する前記ポリマーからなる、請求項1に記載の方法。
- 前記ポリマーが、2、3、または4個以上の、各々が異なる色を発光する様々な発光単位を含み、発光単位は、ポリマー鎖中の繰り返し単位、または少なくとも1個のエンドキャッピング基である、請求項1または2に記載の方法。
- 前記少なくとも1個のエンドキャッピング基が、炭素−金属結合を含有する、請求項1から3のいずれかに記載の方法。
- 前記金属が、Pt、Pd、Os、An、Ru、Re、およびIrからなる群から選択される、請求項4に記載の方法。
- 前記金属が、Irである、請求項4に記載の方法。
- 前記発光ポリマー鎖が、少なくとも1種の蛍光性繰り返し単位を含む、請求項1から6のいずれか一項に記載の方法。
- 前記蛍光性繰り返し単位が、青色繰り返し単位である、請求項7に記載の方法。
- 前記青色繰り返し単位が、アミン基を含む、請求項8に記載の方法。
- 前記発光ポリマー鎖が、緑色蛍光性繰り返し単位をさらに含む、請求項8または9のいずれか一項に記載の方法。
- 前記ポリマーが、赤色および黄色の燐光性エンドキャッピング基からなる群から選択されるエンドキャッピング基を有する、請求項1に記載の方法。
- 前記発光ポリマー鎖が、少なくとも1個の非発光繰り返し単位をさらに含有する、請求項1から11のいずれか一項に記載の方法。
- ポリマーフィードからのモノマーを重合して発光ポリマー鎖を形成し、少なくとも1種のエンドキャッピング剤を使用して前記ポリマー鎖をエンドキャップするステップを含み、ここで、前記少なくとも1種のエンドキャッピング剤が、重合の最初または最中に前記ポリマーフィードに添加される、発光ポリマー鎖と少なくとも1個の発光エンドキャッピング基とを有するポリマーを含む白色発光材料を作製する方法。
- 前記材料が、発光ポリマー鎖と少なくとも1個の発光エンドキャッピング基とを有する前記ポリマーからなる、請求項13に記載の方法。
- 前記ポリマーが、2、3、または4個以上の、各々が異なる色を発光する様々な発光単位を含み、発光単位は、ポリマー鎖中の繰り返し単位、またはエンドキャッピング基である、請求項13または14に記載の方法。
- 前記少なくとも1個の発光エンドキャッピング基が、燐光性エンドキャッピング基である、請求項13から15のいずれか一項に記載の方法。
- 前記燐光性エンドキャッピング基が、炭素−金属結合を含有する、請求項16に記載の方法。
- 前記金属が、Pt、Pd、Os、An、Ru、Re、およびIrからなる群から選択される、請求項17に記載の方法。
- 前記金属が、Irである、請求項17に記載の方法。
- 前記発光ポリマー鎖が、少なくとも1種の蛍光性繰り返し単位を含む、請求項13から19のいずれか一項に記載の方法。
- 前記蛍光性繰り返し単位が、青色繰り返し単位である、請求項20に記載の方法。
- 前記青色繰り返し単位が、アミン基を含む、請求項21に記載の方法。
- 前記発光ポリマー鎖が、緑色蛍光性繰り返し単位をさらに含む、請求項21または22のいずれか一項に記載の方法。
- 前記ポリマーが、赤色および黄色の燐光性エンドキャッピング基からなる群から選択されるエンドキャッピング基を有する、請求項13に記載の方法。
- 前記発光ポリマー鎖が、少なくとも1個の非発光繰り返し単位をさらに含有する、請求項13から24のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0801227A GB2456788B (en) | 2008-01-23 | 2008-01-23 | White light emitting material |
GB0801227.0 | 2008-01-23 | ||
PCT/GB2009/000182 WO2009093033A1 (en) | 2008-01-23 | 2009-01-22 | White light emitting material |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011512424A JP2011512424A (ja) | 2011-04-21 |
JP5636288B2 true JP5636288B2 (ja) | 2014-12-03 |
Family
ID=39166234
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010543564A Expired - Fee Related JP5636288B2 (ja) | 2008-01-23 | 2009-01-22 | 白色発光材料 |
Country Status (8)
Country | Link |
---|---|
US (2) | US20100320454A1 (ja) |
JP (1) | JP5636288B2 (ja) |
KR (1) | KR101599567B1 (ja) |
CN (2) | CN101965751A (ja) |
DE (1) | DE112009000181B4 (ja) |
GB (1) | GB2456788B (ja) |
TW (1) | TWI547542B (ja) |
WO (1) | WO2009093033A1 (ja) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT11607U1 (de) | 2009-08-25 | 2011-01-15 | Zumtobel Lighting Gmbh | Lichtemittierende vorrichtung |
US9142782B2 (en) | 2010-06-25 | 2015-09-22 | Cambridge Display Technology, Ltd. | Organic light-emitting material, device and method |
CN103228698A (zh) * | 2010-07-12 | 2013-07-31 | 韦克森林大学 | 共轭聚合物系统及其应用 |
GB2485001A (en) * | 2010-10-19 | 2012-05-02 | Cambridge Display Tech Ltd | OLEDs |
DE102010055901A1 (de) * | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
GB201105582D0 (en) * | 2011-04-01 | 2011-05-18 | Cambridge Display Tech Ltd | Organic light-emitting device and method |
JP2012222013A (ja) * | 2011-04-05 | 2012-11-12 | Panasonic Corp | 有機薄膜及びこれを発光層に含む有機エレクトロルミネッセンス素子 |
GB201107905D0 (en) | 2011-05-12 | 2011-06-22 | Cambridge Display Tech Ltd | Light-emitting material, composition and device |
GB201107917D0 (en) * | 2011-05-12 | 2011-06-22 | Cambridge Display Tech Ltd | Organic light emitting material and device |
AU2012281140A1 (en) | 2011-07-12 | 2014-01-30 | Wake Forest University | Optoelectronic devices and applications thereof |
EP2835839B1 (en) | 2012-04-06 | 2017-11-08 | Sumitomo Chemical Company, Limited | Organic electroluminescence element and method for manufacturing same |
US9705100B2 (en) | 2012-04-06 | 2017-07-11 | Sumitomo Chemical Company, Limietd | Organic electroluminescent element and method for manufacturing the same |
GB201411621D0 (en) * | 2014-06-30 | 2014-08-13 | Cambridge Display Tech Ltd | Organic transistor |
CN105061777B (zh) * | 2015-09-17 | 2017-06-16 | 太原理工大学 | 一种三基色超支化白光共轭聚合物及其应用 |
GB2588120B (en) * | 2019-10-08 | 2023-11-29 | Sumitomo Chemical Co | Light-emitting composition |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5723873A (en) | 1994-03-03 | 1998-03-03 | Yang; Yang | Bilayer composite electrodes for diodes |
DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
WO1997005184A1 (en) | 1995-07-28 | 1997-02-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
US5798170A (en) * | 1996-02-29 | 1998-08-25 | Uniax Corporation | Long operating life for polymer light-emitting diodes |
CN1130956C (zh) | 1996-07-29 | 2003-12-10 | 剑桥显示技术有限公司 | 具有电极保护的场致发光元件 |
US6255774B1 (en) | 1996-09-04 | 2001-07-03 | Cambridge Display Technology, Ltd. | Multilayer cathode for organic light-emitting device |
JP3899566B2 (ja) | 1996-11-25 | 2007-03-28 | セイコーエプソン株式会社 | 有機el表示装置の製造方法 |
US6452218B1 (en) | 1997-06-10 | 2002-09-17 | Uniax Corporation | Ultra-thin alkaline earth metals as stable electron-injecting electrodes for polymer light emitting diodes |
GB9718393D0 (en) | 1997-08-29 | 1997-11-05 | Cambridge Display Tech Ltd | Electroluminescent Device |
GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
GB2335884A (en) | 1998-04-02 | 1999-10-06 | Cambridge Display Tech Ltd | Flexible substrates for electronic or optoelectronic devices |
US6268695B1 (en) | 1998-12-16 | 2001-07-31 | Battelle Memorial Institute | Environmental barrier material for organic light emitting device and method of making |
GB9903251D0 (en) | 1999-02-12 | 1999-04-07 | Cambridge Display Tech Ltd | Opto-electric devices |
ATE370176T1 (de) | 1999-03-05 | 2007-09-15 | Cambridge Display Tech Ltd | Polymerherstellung |
GB2348316A (en) | 1999-03-26 | 2000-09-27 | Cambridge Display Tech Ltd | Organic opto-electronic device |
WO2001019142A1 (en) | 1999-09-03 | 2001-03-15 | Uniax Corporation | Encapsulation of organic electronic devices |
US6413645B1 (en) | 2000-04-20 | 2002-07-02 | Battelle Memorial Institute | Ultrabarrier substrates |
WO2001082749A2 (en) * | 2000-05-01 | 2001-11-08 | Accuride International, Inc. | Self-closing slide and mechanism for a self-closing slide |
US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
CN100505376C (zh) * | 2000-11-30 | 2009-06-24 | 佳能株式会社 | 发光器件和显示装置 |
WO2002044189A1 (fr) * | 2000-11-30 | 2002-06-06 | Canon Kabushiki Kaisha | Element luminescent et afficheur |
US6693295B2 (en) | 2000-12-25 | 2004-02-17 | Fuji Photo Film Co., Ltd. | Indole derivative, material for light-emitting device and light-emitting device using the same |
DE60239730D1 (de) | 2001-02-20 | 2011-05-26 | Isis Innovation | Metall enthaltende dendrimere |
DE10109027A1 (de) | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
SG92833A1 (en) | 2001-03-27 | 2002-11-19 | Sumitomo Chemical Co | Polymeric light emitting substance and polymer light emitting device using the same |
WO2002081448A1 (fr) * | 2001-04-05 | 2002-10-17 | Sankyo Company, Limited | Derive benzamidine |
WO2002084759A1 (en) | 2001-04-17 | 2002-10-24 | Koninklijke Philips Electronics N.V. | Led comprising a conductive transparent polymer layer with low sulfate and high metal ion content |
JP2002324679A (ja) | 2001-04-26 | 2002-11-08 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
US7250226B2 (en) * | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
JP4574936B2 (ja) * | 2001-08-31 | 2010-11-04 | 日本放送協会 | 燐光発光性化合物及び燐光発光性組成物 |
GB0209652D0 (en) | 2002-04-26 | 2002-06-05 | Univ Cambridge Tech | Solution-processable phosphorescent materials |
JP4417836B2 (ja) * | 2002-06-04 | 2010-02-17 | ハー・ツェー・シュタルク・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 燐光性および発光共役ポリマー、並びに電界発光アセンブリへのその使用方法 |
KR20050016502A (ko) * | 2002-06-04 | 2005-02-21 | 하.체. 스타르크 게엠베하 | 인광 및 발광 공액 중합체 및 전계발광 어셈블리에서의그의 용도 |
US6984461B2 (en) * | 2002-06-21 | 2006-01-10 | Samsung Sdi Co., Ltd. | Blue electroluminescent polymer and organic-electroluminescent device using the same |
US7192657B2 (en) * | 2003-04-15 | 2007-03-20 | 3M Innovative Properties Company | Ethynyl containing electron transport dyes and compositions |
GB0311234D0 (en) | 2003-05-16 | 2003-06-18 | Isis Innovation | Organic phosphorescent material and organic optoelectronic device |
DE10343606A1 (de) * | 2003-09-20 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Weiß emittierende Copolymere, deren Darstellung und Verwendung |
CN100363458C (zh) * | 2004-03-29 | 2008-01-23 | 中国科学院长春应用化学研究所 | 白色电致发光高分子材料及其制备方法 |
GB2440934B (en) * | 2006-04-28 | 2009-12-16 | Cdt Oxford Ltd | Opto-electrical polymers and devices |
US7691292B2 (en) * | 2006-07-28 | 2010-04-06 | General Electric Company | Organic iridium compositions and their use in electronic devices |
GB2442724B (en) * | 2006-10-10 | 2009-10-21 | Cdt Oxford Ltd | Light emissive device |
CN100441609C (zh) * | 2006-10-13 | 2008-12-10 | 华南理工大学 | 一种白光共轭聚合物及其制备方法和应用 |
-
2008
- 2008-01-23 GB GB0801227A patent/GB2456788B/en not_active Expired - Fee Related
-
2009
- 2009-01-22 JP JP2010543564A patent/JP5636288B2/ja not_active Expired - Fee Related
- 2009-01-22 CN CN2009801081658A patent/CN101965751A/zh active Pending
- 2009-01-22 KR KR1020107018656A patent/KR101599567B1/ko active IP Right Grant
- 2009-01-22 TW TW098102674A patent/TWI547542B/zh not_active IP Right Cessation
- 2009-01-22 CN CN201210455129.2A patent/CN102984840B/zh not_active Expired - Fee Related
- 2009-01-22 US US12/864,430 patent/US20100320454A1/en not_active Abandoned
- 2009-01-22 WO PCT/GB2009/000182 patent/WO2009093033A1/en active Application Filing
- 2009-01-22 DE DE112009000181.5T patent/DE112009000181B4/de not_active Expired - Fee Related
-
2013
- 2013-03-18 US US13/846,844 patent/US9136494B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
GB2456788A (en) | 2009-07-29 |
CN102984840B (zh) | 2015-12-02 |
TWI547542B (zh) | 2016-09-01 |
JP2011512424A (ja) | 2011-04-21 |
US20130237680A1 (en) | 2013-09-12 |
CN102984840A (zh) | 2013-03-20 |
KR101599567B1 (ko) | 2016-03-03 |
KR20100106592A (ko) | 2010-10-01 |
CN101965751A (zh) | 2011-02-02 |
DE112009000181T5 (de) | 2011-02-24 |
GB0801227D0 (en) | 2008-02-27 |
US20100320454A1 (en) | 2010-12-23 |
TW200940680A (en) | 2009-10-01 |
WO2009093033A1 (en) | 2009-07-30 |
US9136494B2 (en) | 2015-09-15 |
DE112009000181B4 (de) | 2021-03-18 |
GB2456788B (en) | 2011-03-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5636288B2 (ja) | 白色発光材料 | |
JP5981926B2 (ja) | ポリマーおよび有機発光素子 | |
US7944139B2 (en) | Light emitting device | |
TWI595074B (zh) | 有機發光裝置及方法 | |
JP5721438B2 (ja) | 発光デバイスおよびそのための材料 | |
JP4966203B2 (ja) | 発光装置 | |
WO2013005031A1 (en) | Organic light emitting device and method | |
JP5557197B2 (ja) | 青色発光材料 | |
KR101632087B1 (ko) | 유기발광소자 | |
JP6225120B2 (ja) | ポリマー | |
JP2013528232A (ja) | 有機発光ポリマー及びデバイス | |
JP2008525957A5 (ja) | ||
KR20120013385A (ko) | 유기 전기발광 소자 및 이의 제조 방법 | |
JP5732042B2 (ja) | 有機発光材料および素子 | |
JP2009525605A (ja) | 燐光有機発光装置 | |
CN101385158B (zh) | 光发射器件 | |
JP2009525605A5 (ja) | ||
JP2011510509A (ja) | パルス駆動発光デバイスおよびそのための組成物 | |
JP5732041B2 (ja) | モノマー、重合法およびポリマー | |
JP5274448B2 (ja) | 光電気ポリマー及び装置 | |
JP2014112674A (ja) | 有機発光デバイス | |
JP2009535795A5 (ja) | ||
JP2011529975A (ja) | 有機発光材料および素子 | |
WO2015044656A1 (en) | Polymer and organic light emitting device |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20111101 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20111104 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20111101 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130822 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130827 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131126 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140304 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140320 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20140703 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20140825 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20140826 |
|
TRDD | Decision of grant or rejection written | ||
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20140828 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141014 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141020 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5636288 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |