JP2008523636A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008523636A5 JP2008523636A5 JP2007546164A JP2007546164A JP2008523636A5 JP 2008523636 A5 JP2008523636 A5 JP 2008523636A5 JP 2007546164 A JP2007546164 A JP 2007546164A JP 2007546164 A JP2007546164 A JP 2007546164A JP 2008523636 A5 JP2008523636 A5 JP 2008523636A5
- Authority
- JP
- Japan
- Prior art keywords
- host
- charge transport
- polymer
- metal complex
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 claims description 128
- 229920000642 polymer Polymers 0.000 claims description 82
- 150000004696 coordination complex Chemical class 0.000 claims description 51
- 229910052751 metal Inorganic materials 0.000 claims description 33
- 239000002184 metal Substances 0.000 claims description 33
- 239000000178 monomer Substances 0.000 claims description 27
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 18
- 238000005191 phase separation Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 238000000137 annealing Methods 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003446 ligand Substances 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000547 conjugated polymer Polymers 0.000 description 8
- 230000021615 conjugation Effects 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000010129 solution processing Methods 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Chemical group 0.000 description 7
- 239000001301 oxygen Chemical group 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- 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
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- -1 phenylene, phenylene vinylene Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 230000005258 radioactive decay Effects 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- AZOAOCNEXRBLOT-UHFFFAOYSA-N 3,9-dibromo-5,7-dihydrobenzo[d][2]benzoxepine Chemical compound C1OCC2=CC(Br)=CC=C2C2=CC=C(Br)C=C12 AZOAOCNEXRBLOT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical class [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical class [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241001229889 Metis Species 0.000 description 1
- 235000002779 Morchella esculenta Nutrition 0.000 description 1
- 240000002769 Morchella esculenta Species 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
- 241000233805 Phoenix Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920000291 Poly(9,9-dioctylfluorene) Polymers 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
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl 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
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000005620 boronic acid group Chemical group 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
- 239000002775 capsule Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 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
- 230000005281 excited state Effects 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation 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
- 229910052740 iodine Chemical class 0.000 description 1
- 239000011630 iodine Chemical class 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 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
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000387 optically detected magnetic resonance Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 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
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 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
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0427266.2A GB0427266D0 (en) | 2004-12-13 | 2004-12-13 | Phosphorescent OLED |
| GB0427266.2 | 2004-12-13 | ||
| PCT/GB2005/004768 WO2006064194A1 (en) | 2004-12-13 | 2005-12-12 | Phosphorescent oled |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008523636A JP2008523636A (ja) | 2008-07-03 |
| JP2008523636A5 true JP2008523636A5 (https=) | 2010-10-14 |
| JP5183212B2 JP5183212B2 (ja) | 2013-04-17 |
Family
ID=34073629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007546164A Expired - Fee Related JP5183212B2 (ja) | 2004-12-13 | 2005-12-12 | 燐光性ｏｌｅｄ |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8063554B2 (https=) |
| JP (1) | JP5183212B2 (https=) |
| DE (1) | DE112005003006B4 (https=) |
| GB (2) | GB0427266D0 (https=) |
| WO (1) | WO2006064194A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003019696A2 (en) * | 2001-08-25 | 2003-03-06 | Cambridge Display Technology Limited | Electroluminescent device |
| GB201122316D0 (en) * | 2011-12-23 | 2012-02-01 | Cambridge Display Tech Ltd | Polymer, polymer composition and organic light-emitting device |
| KR101921896B1 (ko) * | 2011-12-12 | 2018-11-26 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
| CN104093689A (zh) | 2012-01-31 | 2014-10-08 | 剑桥显示技术有限公司 | 聚合物 |
| GB2508409B (en) * | 2012-11-30 | 2015-11-25 | Cambridge Display Tech Ltd | Organic light-emitting composition, device and method |
| US8530685B1 (en) | 2012-07-30 | 2013-09-10 | General Electric Company | Monodentate gold ethynyl complexes |
| GB2508191B (en) * | 2012-11-23 | 2015-10-07 | Cambridge Display Tech Ltd | Organic light emissive device |
| JP6130757B2 (ja) * | 2013-09-04 | 2017-05-17 | 本田技研工業株式会社 | 光電変換材料及びその製造方法と、それを用いた有機薄膜太陽電池 |
| KR102384224B1 (ko) | 2014-12-30 | 2022-04-08 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
| US10026898B2 (en) * | 2015-02-18 | 2018-07-17 | Purdue Research Foundation | Methods and compositions for enhancing processability and charge transport of polymer semiconductors and devices made therefrom |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5723873A (en) | 1994-03-03 | 1998-03-03 | Yang; Yang | Bilayer composite electrodes for diodes |
| SE506019C2 (sv) * | 1994-05-17 | 1997-11-03 | Forskarpatent I Linkoeping Ab | Ljuskälla av konjugerade polymerer med spänningsstyrd färg samt metod för tillverkning av ljuskällan |
| DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
| CN1229415C (zh) | 1995-07-28 | 2005-11-30 | 陶氏环球技术公司 | 2,7－芳基－9－取代的芴和9－取代的芴的低聚物和聚合物 |
| US5798170A (en) | 1996-02-29 | 1998-08-25 | Uniax Corporation | Long operating life for polymer light-emitting diodes |
| JP3724589B2 (ja) | 1996-07-29 | 2005-12-07 | ケンブリッジ ディスプレイ テクノロジー リミテッド | エレクトロルミネセンス素子 |
| ATE247372T1 (de) | 1996-09-04 | 2003-08-15 | Cambridge Display Tech Ltd | Lichtemittierende organische vorrichtungen mit verbesserter kathode |
| 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 |
| US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| 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 |
| WO2000053656A1 (en) | 1999-03-05 | 2000-09-14 | Cambridge Display Technology Limited | Polymer preparation |
| GB2348316A (en) | 1999-03-26 | 2000-09-27 | Cambridge Display Tech Ltd | Organic opto-electronic device |
| CN1385053A (zh) | 1999-09-03 | 2002-12-11 | 优尼爱克斯公司 | 有机电子器件的封装 |
| US6413645B1 (en) | 2000-04-20 | 2002-07-02 | Battelle Memorial Institute | Ultrabarrier substrates |
| US8206838B2 (en) * | 2000-06-12 | 2012-06-26 | Sumitomo Chemical Co., Ltd. | Polymer matrix electroluminescent materials and devices |
| EP1175128B1 (en) * | 2000-07-17 | 2010-09-22 | FUJIFILM Corporation | Light emitting element and azole compound |
| US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| JP4454130B2 (ja) | 2000-09-25 | 2010-04-21 | 京セラ株式会社 | 有機エレクトロルミネッセンス素子 |
| WO2002026856A1 (en) | 2000-09-26 | 2002-04-04 | Cambridge Display Technology Limited | Twisted polymers, uses thereof and processes for the preparation of statistical copolymers |
| AU2002222565A1 (en) | 2000-11-30 | 2002-06-11 | Canon Kabushiki Kaisha | Luminescent element and display |
| CN1285601C (zh) | 2000-11-30 | 2006-11-22 | 佳能株式会社 | 发光器件和显示器 |
| 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 |
| SG2009086778A (en) * | 2000-12-28 | 2016-11-29 | Semiconductor Energy Lab Co Ltd | Luminescent device |
| CA2438745C (en) | 2001-02-20 | 2010-11-30 | Isis Innovation Limited | Metal-containing dendrimers |
| DE10109027A1 (de) | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| AU2002306698A1 (en) * | 2001-03-14 | 2002-09-24 | The Trustees Of Princeton University | Materials and devices for blue phosphorescence based organic light emitting diodes |
| SG92833A1 (en) | 2001-03-27 | 2002-11-19 | Sumitomo Chemical Co | Polymeric light emitting substance and polymer light emitting device using the same |
| SK12082003A3 (sk) | 2001-04-05 | 2004-09-08 | Sankyo Company Limited | Benzamidínové deriváty |
| GB0109295D0 (en) * | 2001-04-12 | 2001-05-30 | Univ Cambridge Tech | Optoelectronic devices and a method for producing the same |
| CN100582195C (zh) * | 2001-04-13 | 2010-01-20 | 株式会社半导体能源研究所 | 有机发光元件和采用所述元件的发光装置 |
| KR20030024690A (ko) | 2001-04-17 | 2003-03-26 | 코닌클리케 필립스 일렉트로닉스 엔.브이. | 저 황산염 및 고 금속 이온 함량을 갖는 전도성 투명중합체 층을 포함하는 ｌｅｄ |
| US7199515B2 (en) * | 2001-06-01 | 2007-04-03 | Semiconductor Energy Laboratory Co., Ltd. | Organic light emitting element and light emitting device using the element |
| MY128940A (en) | 2001-07-10 | 2007-03-30 | Dow Global Technologies Inc | Electroactive polymers and devices made therefrom |
| 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 |
| TWI267545B (en) * | 2003-06-17 | 2006-12-01 | Univ Tsinghua | Electroluminescent conjugated polymers containing phosphorescent moieties and the application thereof in LED |
| JP2005158520A (ja) * | 2003-11-26 | 2005-06-16 | Kyocera Corp | 有機電界発光素子 |
-
2004
- 2004-12-13 GB GBGB0427266.2A patent/GB0427266D0/en not_active Ceased
-
2005
- 2005-12-12 WO PCT/GB2005/004768 patent/WO2006064194A1/en not_active Ceased
- 2005-12-12 US US11/721,321 patent/US8063554B2/en not_active Expired - Fee Related
- 2005-12-12 DE DE112005003006.7T patent/DE112005003006B4/de not_active Expired - Fee Related
- 2005-12-12 JP JP2007546164A patent/JP5183212B2/ja not_active Expired - Fee Related
- 2005-12-12 GB GB0710097A patent/GB2434695B/en not_active Expired - Fee Related
-
2011
- 2011-11-15 US US13/297,157 patent/US9172052B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5981926B2 (ja) | ポリマーおよび有機発光素子 | |
| JP5557197B2 (ja) | 青色発光材料 | |
| JP5721438B2 (ja) | 発光デバイスおよびそのための材料 | |
| JP5847805B2 (ja) | 有機発光ポリマー及びデバイス | |
| JP5636288B2 (ja) | 白色発光材料 | |
| US9172052B2 (en) | Phosphorescent OLED | |
| KR101579339B1 (ko) | 유기 전기발광 소자 및 이의 제조 방법 | |
| JP5371442B2 (ja) | アリールアミンポリマー | |
| JP5732042B2 (ja) | 有機発光材料および素子 | |
| JP2009520864A5 (https=) | ||
| JP4966203B2 (ja) | 発光装置 | |
| JP2009525605A (ja) | 燐光有機発光装置 | |
| JP2009525605A5 (https=) | ||
| JP2008525957A5 (https=) | ||
| JP2008523636A5 (https=) | ||
| CN102395615B (zh) | 单体、聚合方法及聚合物 | |
| KR101395530B1 (ko) | 광-전기적 중합체 및 디바이스 | |
| JP2009525606A (ja) | 有機発光装置 | |
| KR20140066643A (ko) | 유기 발광 소자 | |
| JP2009535795A5 (https=) | ||
| 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 | |
| GB2470145A (en) | Phosphorescent material | |
| HK1154263A (en) | Pulsed driven light emissive device and composition therefor | |
| HK1158677A (en) | Blue-light emitting material |