JP5557197B2 - 青色発光材料 - Google Patents
青色発光材料 Download PDFInfo
- Publication number
- JP5557197B2 JP5557197B2 JP2011520584A JP2011520584A JP5557197B2 JP 5557197 B2 JP5557197 B2 JP 5557197B2 JP 2011520584 A JP2011520584 A JP 2011520584A JP 2011520584 A JP2011520584 A JP 2011520584A JP 5557197 B2 JP5557197 B2 JP 5557197B2
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- perylene
- polymer
- formula
- group
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title description 60
- 229920000642 polymer Polymers 0.000 claims description 76
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 64
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 56
- 229920000547 conjugated polymer Polymers 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 125000006850 spacer group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000007641 inkjet printing Methods 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005620 boronic acid group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010129 solution processing Methods 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- 230000032258 transport Effects 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- -1 Poly (p-phenylene) Polymers 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 239000003446 ligand Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000003107 substituted aryl group Chemical group 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000008393 encapsulating agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 229960002796 polystyrene sulfonate Drugs 0.000 description 3
- 239000011970 polystyrene sulfonate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 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
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 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 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- ACUNTFHQSSSGDQ-UHFFFAOYSA-N B(O)O.B(O)O.B(O)O.B(O)O.C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 Chemical class B(O)O.B(O)O.B(O)O.B(O)O.C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 ACUNTFHQSSSGDQ-UHFFFAOYSA-N 0.000 description 1
- PSKBTLRFPUEDLH-UHFFFAOYSA-N B(O)O.B(O)O.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34 Chemical compound B(O)O.B(O)O.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34 PSKBTLRFPUEDLH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- 229920000265 Polyparaphenylene Polymers 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
- 229920002125 Sokalan® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZGDJMMPBPMJJBR-UHFFFAOYSA-N bis(1H-indol-2-yl)diazene Chemical compound c1c(N=Nc2cc3ccccc3[nH]2)[nH]c2ccccc12 ZGDJMMPBPMJJBR-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 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
- 150000004777 chromones Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 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
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229920000736 dendritic polymer Polymers 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
- 238000005516 engineering process Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 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
- 230000001815 facial effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 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
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-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
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 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
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Luminescent Compositions (AREA)
- Led Device Packages (AREA)
- Led Devices (AREA)
Description
(i)負電荷キャリアを輸送し、第1のLUMO準位及び第1のHOMO準位によって規定される第1のバンドギャップを有する、第1の領域;及び
(ii)正電荷キャリアを輸送し、第2のLUMO準位及び第2のHOMO準位によって規定される第2のバンドギャップを有する、第2の領域;及び
(iii)正電荷及び負電荷のキャリアを受け入れ結合させて光を発生させ、第3のLUMO準位及び第3のHOMO準位によって規定される第3のバンドギャップを有する、第3の領域。
ここで、各領域は1種又は複数種のモノマーを含み、有機ポリマー中のモノマーの量及び配置は、ポリマーにおける第1、第2、及び第3のバンドギャップが互いにはっきりと異なるように選択される。ペリレンには言及していない。
− フルオレン繰り返し単位のホモポリマー(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)を、電子輸送を提供するために利用してもよい。
− トリアリールアミン繰り返し単位、特に繰り返し単位7:
ML1 qL2 rL3 s
26
を含む金属錯体が挙げられ、式中、Mは金属であり;L1、L2、及びL3の各々は配位基であり;qは整数であり;r及びsはそれぞれ独立に0又は整数であり;(a.q)+(b.r)+(c.s)の和はMにおいて利用可能な配位部位の数に等しく、ここでaはL1における配位部位の数であり、bはL2における配位部位の数であり、cはL3における配位部位の数である。
− ランタニド金属、例えばセリウム、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、及びネオジムなど;及び
− dブロック金属、特に2列(row)及び3列のもの、すなわち元素番号39〜48及び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、及び金
が挙げられる。
WO00/53656のスズキ法に従って、式6のフルオレン単位(0.94当量)、US2005/209422の実施例P1に記載のタイプの、式7のアミン繰り返し単位(0.06当量)、及び実施例3のモノマーから得られる主鎖のペリレン繰り返し単位(0.0025当量)を反応させてMr 925,000及びMp 884,000を有するポリマーを生成させることにより、ポリマーを調製した。
WO00/53656のスズキ法に従って、式6のフルオレン単位(0.94当量)、US2005/209422の実施例P1に記載のタイプの、式7のアミン繰り返し単位(0.06当量)、及び実施例5のモノマーから得られる側鎖のペリレン繰り返し単位(0.0025当量)を反応させてMr 1,087,000及びMp 997,000を有するポリマーを生成させることにより、ポリマーを調製した。
WO00/5366のスズキ法に従って、式6のフルオレン単位(0.94当量)、US2005/209422の実施例P1に記載のタイプの、式7のアミン繰り返し単位(0.06当量)、及び実施例4の材料から得られるエンドキャップ基を反応させてMr 520,000及びMp 443,000を有するポリマーを生成させることにより、ポリマーを調製した。
WO00/5366のスズキ法に従って、式6のフルオレン単位(0.94当量)及び式7のアミン繰り返し単位(0.06当量)を反応させてMr 1,280,000及びMp 1,100,00,を有するポリマーを生成させることにより、ポリマーを調製した。これを実施例1のペリレン化合物と混合した。
実施例1の化合物の代わりに実施例2の化合物を使用したことを除いて、組成物例1の通りに組成物を調製した。
結果から、比較ポリマーと比較して、本発明による材料でT90が向上していることが理解できる。T70も、1つの事例以外はすべて向上している。したがって減衰曲線は初期の段階でより平坦である。このことは差違のある劣化に関して有益であるが、これは結果として、フルカラーデバイスにおいて青色の輝度が赤及び緑と比較して必要なレベルであるように青色の駆動条件を調整する必要性が低いからである。
Claims (26)
- 共役ポリマーであって、
青色発光性ペリレンが、
2、5、8、又は11位において、共役ポリマーの主鎖に側鎖として共有結合しているか、共役ポリマーの主鎖の末端基として共有結合しており、あるいは、
2、5、8、及び11位のうち任意の2つの組み合わせを介して連結された繰り返し単位として共役ポリマーの主鎖において提供されている、
共役ポリマー。 - 共役ポリマーが電子輸送繰り返し単位及び/又は正孔輸送繰り返し単位を含む、請求項1に記載の発光ポリマー。
- ペリレンがスペーサー基を介して共役ポリマーの骨格に結合している、請求項3又は4に記載の発光ポリマー。
- スペーサー基がフェニルである、請求項5に記載の発光ポリマー。
- スペーサー基がアルキルである、請求項5に記載の発光ポリマー。
- 共役ポリマーが、式IV〜VIIIのうちの1つを有する繰り返し単位を5mol%まで含有する、請求項8又は9に記載の発光ポリマー。
- スペーサー基がフェニルである、請求項11に記載の発光ポリマー。
- スペーサー基がフェニルである、請求項13に記載の発光ポリマー。
- スズキ重合又はヤマモト重合を用い、それによってモノマーが重合され、各モノマーが少なくとも2つの反応性基を有する、請求項1から14のいずれか一項に記載の発光ポリマーを作製する方法。
- 反応性基が、ボロン酸又はボロン酸エステルなどのホウ素誘導体基、ハロゲン、トシラート、メシラート、及びトリフラートから選択される、請求項15に記載の方法。
- アノード、カソード、及び、アノードとカソードの間にある、請求項1から14のいずれか一項に記載の発光ポリマーを含むエレクトロルミネッセンス層とを含む、有機発光デバイス(OLED)。
- アノードからエレクトロルミネッセンス層への正孔注入を補助するための導電性正孔注入層を、アノード及びエレクトロルミネッセンス層の間に含む、請求項17に記載のOLED。
- 溶液処理によって、請求項1から14のいずれか一項に記載の発光ポリマーを溶液から堆積させてOLEDの層を形成するステップを含む、請求項17又は18に記載のOLEDを作製する方法。
- 溶液処理法がスピンコーティング又はインクジェット印刷である、請求項19に記載の方法。
- 請求項17又は18に記載のOLEDを含む光源。
- 光源がフルカラーディスプレイである、請求項21に記載の光源。
- R1が任意に置換されているフェニルであり、R5'が任意に置換されている1,4−フェニレンを表す、請求項23に記載のモノマー。
- 各Xが独立に、ハロゲン、ボロン酸、ボロン酸エステル、スルホン酸及びスルホン酸エステルから成る群から選択される、請求項23又は24に記載のモノマー。
- Xが臭素である、請求項25に記載のモノマー。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0814161.6A GB0814161D0 (en) | 2008-08-01 | 2008-08-01 | Blue-light emitting material |
GB0814161.6 | 2008-08-01 | ||
PCT/GB2009/001874 WO2010013006A2 (en) | 2008-08-01 | 2009-07-30 | Blue-light emitting material |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011529976A JP2011529976A (ja) | 2011-12-15 |
JP5557197B2 true JP5557197B2 (ja) | 2014-07-23 |
Family
ID=39767425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011520584A Active JP5557197B2 (ja) | 2008-08-01 | 2009-07-30 | 青色発光材料 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8604464B2 (ja) |
EP (1) | EP2326695B1 (ja) |
JP (1) | JP5557197B2 (ja) |
KR (1) | KR20110047216A (ja) |
CN (1) | CN102137912A (ja) |
GB (1) | GB0814161D0 (ja) |
TW (1) | TWI461508B (ja) |
WO (1) | WO2010013006A2 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0906554D0 (en) | 2009-04-16 | 2009-05-20 | Cambridge Display Tech Ltd | Organic electroluminescent device |
GB2471062B (en) * | 2009-04-16 | 2012-10-31 | Cambridge Display Tech Ltd | Organic light-emitting materials and devices |
GB2484253B (en) | 2010-05-14 | 2013-09-11 | Cambridge Display Tech Ltd | Organic light-emitting composition and device |
GB2495250A (en) * | 2010-06-25 | 2013-04-03 | Cambridge Display Tech Ltd | Organic light-emitting composition comprising anthranthene derivatives and device and method using the same |
GB2485001A (en) * | 2010-10-19 | 2012-05-02 | Cambridge Display Tech Ltd | OLEDs |
TW201241036A (en) * | 2010-11-15 | 2012-10-16 | Sumitomo Chemical Co | High-polymer compound and method for producing the same |
DE102014004224A1 (de) | 2014-03-25 | 2015-10-01 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Arylboranverbindung, deren Verfahren zum Herstellen und deren Verwendung |
EP3439061B1 (en) | 2016-03-29 | 2021-07-21 | Sumitomo Chemical Company, Limited | Light-emitting element |
US11225602B2 (en) | 2016-06-24 | 2022-01-18 | Sumitomo Chemical Company, Limited | Light emitting device |
KR20180114349A (ko) | 2017-04-10 | 2018-10-18 | 국보미 | 학생 카드 인식을 활용한 친환경 전기 자전거 운행 시스템 |
CN110846020A (zh) * | 2018-07-20 | 2020-02-28 | 宁波凯丽安科技股份有限公司 | 一种采用互补色原理材料的光致变色染料 |
WO2020053150A1 (en) * | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Family Cites Families (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5150006A (en) * | 1991-08-01 | 1992-09-22 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (II) |
US5432014A (en) * | 1991-11-28 | 1995-07-11 | Sanyo Electric Co., Ltd. | Organic electroluminescent element and a method for producing the same |
US5723873A (en) * | 1994-03-03 | 1998-03-03 | Yang; Yang | Bilayer composite electrodes for diodes |
DE69526614T2 (de) * | 1994-09-12 | 2002-09-19 | Motorola, Inc. | Lichtemittierende Vorrichtungen die Organometallische Komplexe enthalten. |
DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
JP3865406B2 (ja) | 1995-07-28 | 2007-01-10 | 住友化学株式会社 | 2,7−アリール−9−置換フルオレン及び9−置換フルオレンオリゴマー及びポリマー |
US5798170A (en) * | 1996-02-29 | 1998-08-25 | Uniax Corporation | Long operating life for polymer light-emitting diodes |
DE69710781T2 (de) | 1996-07-29 | 2002-10-31 | Cambridge Display Tech | Elektrolumineszierende anordnungen mit elektrodenschutz |
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 |
KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
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 |
GB2340304A (en) | 1998-08-21 | 2000-02-16 | Cambridge Display Tech Ltd | Organic light emitters |
US6268695B1 (en) | 1998-12-16 | 2001-07-31 | Battelle Memorial Institute | Environmental barrier material for organic light emitting device and method of making |
CA2360644A1 (en) * | 1999-02-04 | 2000-08-10 | The Dow Chemical Company | Fluorene copolymers and devices made therefrom |
GB9903251D0 (en) | 1999-02-12 | 1999-04-07 | Cambridge Display Tech Ltd | Opto-electric devices |
CN1165563C (zh) | 1999-03-05 | 2004-09-08 | 剑桥显示技术有限公司 | 聚合物制备 |
GB2348316A (en) | 1999-03-26 | 2000-09-27 | Cambridge Display Tech Ltd | Organic opto-electronic device |
CA2381230A1 (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 |
AU1540001A (en) | 1999-12-09 | 2001-06-18 | Cambridge Display Technology Limited | Fluorene-perylene copolymers and uses thereof |
GB0004541D0 (en) | 2000-02-25 | 2000-04-19 | Cambridge Display Tech Ltd | Luminescent polymer |
US6286695B1 (en) * | 2000-04-11 | 2001-09-11 | Killick Industries Llc | Engine lifting and positioning assembly |
US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
EP1325054B1 (en) | 2000-09-26 | 2006-07-19 | Cambridge Display Technology Limited | Twisted polymers, uses thereof and processes for the preparation of statistical copolymers |
IL154960A0 (en) | 2000-10-10 | 2003-10-31 | Du Pont | Polymers having attached luminescent metal complexes and devices made with sych polymers |
EP1349435B8 (en) * | 2000-11-30 | 2018-09-19 | Canon Kabushiki Kaisha | Luminescent element and display |
KR100825182B1 (ko) | 2000-11-30 | 2008-04-24 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
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 |
WO2002066552A1 (en) | 2001-02-20 | 2002-08-29 | Isis Innovation Limited | Metal-containing dendrimers |
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 |
CN1610666A (zh) | 2001-04-05 | 2005-04-27 | 三共株式会社 | 苄脒衍生物 |
CN100353580C (zh) | 2001-04-17 | 2007-12-05 | 皇家菲利浦电子有限公司 | 有机发光二极管 |
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 |
GB0111549D0 (en) | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
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 |
US7238435B2 (en) * | 2001-09-04 | 2007-07-03 | Canon Kabushiki Kaisha | Polymeric compound and organic luminescence device |
CN1325600C (zh) * | 2002-05-10 | 2007-07-11 | 剑桥显示技术有限公司 | 聚合物及其制备和用途 |
AU2003240832A1 (en) | 2002-05-31 | 2003-12-19 | E.I. Du Pont De Nemours And Company | Copolymers having tunable energy levels and color of emission |
DE10249723A1 (de) * | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
DE10337077A1 (de) * | 2003-08-12 | 2005-03-10 | Covion Organic Semiconductors | Konjugierte Copolymere, deren Darstellung und Verwendung |
KR101141465B1 (ko) * | 2003-09-20 | 2012-05-07 | 메르크 파텐트 게엠베하 | 공액 중합체, 그의 제조 및 그의 용도 |
DE10343606A1 (de) | 2003-09-20 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Weiß emittierende Copolymere, deren Darstellung und Verwendung |
JP2005158520A (ja) | 2003-11-26 | 2005-06-16 | Kyocera Corp | 有機電界発光素子 |
WO2005085176A1 (ja) * | 2004-03-09 | 2005-09-15 | Nissan Chemical Industries, Ltd. | π共役系芳香環含有化合物及び有機エレクトロルミネッセンス素子 |
GB0526393D0 (en) | 2005-12-23 | 2006-02-08 | Cdt Oxford Ltd | Light emissive device |
JP5424622B2 (ja) | 2008-12-01 | 2014-02-26 | キヤノン株式会社 | ペリレン化合物及びこれを用いた有機発光素子 |
GB2471062B (en) * | 2009-04-16 | 2012-10-31 | Cambridge Display Tech Ltd | Organic light-emitting materials and devices |
-
2008
- 2008-08-01 GB GBGB0814161.6A patent/GB0814161D0/en not_active Ceased
-
2009
- 2009-07-30 KR KR1020117004889A patent/KR20110047216A/ko not_active Application Discontinuation
- 2009-07-30 CN CN2009801337575A patent/CN102137912A/zh active Pending
- 2009-07-30 US US13/056,108 patent/US8604464B2/en active Active
- 2009-07-30 JP JP2011520584A patent/JP5557197B2/ja active Active
- 2009-07-30 EP EP09784823.8A patent/EP2326695B1/en not_active Not-in-force
- 2009-07-30 WO PCT/GB2009/001874 patent/WO2010013006A2/en active Application Filing
- 2009-07-31 TW TW098125952A patent/TWI461508B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
US20110186828A1 (en) | 2011-08-04 |
CN102137912A (zh) | 2011-07-27 |
TWI461508B (zh) | 2014-11-21 |
KR20110047216A (ko) | 2011-05-06 |
US8604464B2 (en) | 2013-12-10 |
WO2010013006A3 (en) | 2010-09-23 |
JP2011529976A (ja) | 2011-12-15 |
TW201022402A (en) | 2010-06-16 |
WO2010013006A2 (en) | 2010-02-04 |
EP2326695B1 (en) | 2015-02-25 |
EP2326695A2 (en) | 2011-06-01 |
GB0814161D0 (en) | 2008-09-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5557197B2 (ja) | 青色発光材料 | |
JP5981926B2 (ja) | ポリマーおよび有機発光素子 | |
JP5371442B2 (ja) | アリールアミンポリマー | |
JP5847805B2 (ja) | 有機発光ポリマー及びデバイス | |
JP5721438B2 (ja) | 発光デバイスおよびそのための材料 | |
KR101599567B1 (ko) | 백색 발광 재료 | |
JP4966203B2 (ja) | 発光装置 | |
JP2009521118A (ja) | 電子装置 | |
JP5183212B2 (ja) | 燐光性oled | |
JP2009520864A5 (ja) | ||
JP2008525957A5 (ja) | ||
JP5732042B2 (ja) | 有機発光材料および素子 | |
JP2008523636A5 (ja) | ||
JP5732041B2 (ja) | モノマー、重合法およびポリマー | |
KR101395530B1 (ko) | 광-전기적 중합체 및 디바이스 | |
JP2009525606A (ja) | 有機発光装置 | |
JP5789251B2 (ja) | モノマー、ポリマー、およびその製造方法 | |
JP2009535795A5 (ja) | ||
JP2011529975A (ja) | 有機発光材料および素子 | |
JP2012524140A (ja) | ポリマーおよび重合方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20111101 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20111101 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120615 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130626 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130723 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131016 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140430 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20140526 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140526 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5557197 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20140617 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |