JP6129207B2 - 非対称ジアリールアミンフルオレンユニットを含むポリマー - Google Patents
非対称ジアリールアミンフルオレンユニットを含むポリマー Download PDFInfo
- Publication number
- JP6129207B2 JP6129207B2 JP2014551681A JP2014551681A JP6129207B2 JP 6129207 B2 JP6129207 B2 JP 6129207B2 JP 2014551681 A JP2014551681 A JP 2014551681A JP 2014551681 A JP2014551681 A JP 2014551681A JP 6129207 B2 JP6129207 B2 JP 6129207B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- substituted
- group
- formula
- layer
- 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
- 229920000642 polymer Polymers 0.000 title claims description 131
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 230000005525 hole transport Effects 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- -1 sulfonate esters Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000004065 semiconductor Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000005620 boronic acid group Chemical class 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 136
- 239000000463 material Substances 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 230000000052 comparative effect Effects 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 18
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004528 spin coating Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000000732 arylene group Chemical group 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- 125000003107 substituted aryl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000010129 solution processing Methods 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008393 encapsulating agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 229920000412 polyarylene Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 101100451713 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HTL1 gene Proteins 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920000547 conjugated polymer Polymers 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
- 238000001035 drying Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910021397 glassy carbon Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 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
- 229910052740 iodine Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-O tritert-butylphosphanium Chemical compound CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-O 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- WVIZUQMODASULQ-UHFFFAOYSA-N 2,7-dibromo-9-(3,5-dihexylphenyl)-9-octylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1(CCCCCCCC)C1=CC(CCCCCC)=CC(CCCCCC)=C1 WVIZUQMODASULQ-UHFFFAOYSA-N 0.000 description 1
- BKIDJIYDGSCJCR-UHFFFAOYSA-N 2-methylpropan-2-amine;perchloric acid Chemical compound CC(C)(C)[NH3+].[O-]Cl(=O)(=O)=O BKIDJIYDGSCJCR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 235000019502 Orange oil Nutrition 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
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005577 anthracene 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229920001400 block copolymer Polymers 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 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
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- 238000012966 insertion method Methods 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 Substances 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible 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
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3245—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and oxygen as heteroatoms
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/411—Suzuki reactions
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
-
- 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
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
アノード/ホール注入層/発光層/カソード
アノード/ホール輸送層/発光層/カソード
アノード/ホール注入層/ホール輸送層/発光層/カソード
アノード/ホール注入層/ホール輸送層/発光層/電子輸送層/カソード。
3mm直径のガラス状炭素作用電極
Ag/AgCl/ノーリーク参照電極
Ptワイヤ補助電極
アセトニトリル中0.1Mのテトラブチルアンモニウムヘキサフルオロホスフェート
LUMO=4.8−フェロセン(ピークツーピーク最大平均)+オンセット
サンプル:3000rpmでスピンされたトルエン中5mg/mLの1滴のLUMO(還元)測定:
良好な可逆性還元事象は、通常、200mV/sおよびスイッチング電位−2.5Vにおいて測定される厚いフィルムに関して観察される。還元事象は、10サイクルにわたって測定および比較されるべきであり、通常の測定は、3番目のサイクルで行われる。オンセットは、還元事象の最も急勾配の部分の最良適合線と基線との交点におけるものである。
*−(Sp)w−XL
(VI)
式中、Spは、スペーサー基、例えば実施例C1−10アルキルを表し;wは0または1であり;XLは、架橋性基を表し;*は、架橋性基のポリマーへの結合点を表す。
−置換または非置換アルキル(C1−20アルキルであってもよい)、ここで1つ以上の非隣接C原子は、置換されていてもよいアリールまたはヘテロアリール、O、S、置換されたN、C=Oまたは−COO−で置き換えられていてもよく、1つ以上のH原子は、Fで置き換えられていてもよい;
−置換若しくは非置換アリールまたはヘテロアリール基、或いは線状もしくは分岐鎖のアリールまたはヘテロアリール、ここでこれらの各々は、独立に置換されていてもよく、例えば式−(Ar4)rの基であり、式中、Ar4は、各出現において独立に、置換または非置換アリールまたはヘテロアリールであり、rは少なくとも1である(1、2または3であってもよい);
−フルオレンユニットに直接結合した、またはスペーサー基、例えば二重結合を含む基、例えばビニルまたはアクリレート基、またはベンゾシクロブタン基によってそれらから間隔をあけて配置された架橋性基、例えば上記で記載されるような式(VI)の架橋性基。
アルキル、例えばC1−20アルキル、ここで、1つ以上の非隣接C原子は、O、S、置換されたN、C=Oまたは−COO−で置き換えられていてもよく、アルキル基の1つ以上のH原子は、Fで置き換えられていてもよく、または1つ以上の基R7で置換されていてもよいアリールまたはヘテロアリールで置き換えられていてもよい、
1つ以上の基R7で置換されていてもよいアリールまたはヘテロアリール、
NR8 2、OR8、SR8、ならびに
フッ素、ニトロおよびシアノ;
式中、各R7は、独立に、アルキル、例えばC1−20アルキルであり、ここで1つ以上の非隣接C原子は、O、S、置換されたN、C=Oまたは−COO−で置き換えられていてもよく、アルキル基の1つ以上のH原子は、FまたはDで置き換えられていてもよく;各R8は、独立に、アルキル、例えばC1−20アルキル、および1つ以上のアルキル基で置換されていてもよいアリールまたはヘテロアリール、例えば非置換または1つ以上のC1−20アルキル基で置換されるフェニルからなる群から選択される。
上記で記載されるような式(I)の繰り返しユニットを含む共役ポリマー、例えばホモポリマーまたはコポリマーの調製の好ましい方法は、「金属挿入」を含み、ここでこの金属錯体触媒の金属原子は、アリールまたはヘテロアリール基とモノマーの脱離基との間に挿入される。例示的な金属挿入方法は、例えば国際公開第00/53656号に記載されるようなSuzuki重合、および例えばT.Yamamoto,「Electrically Conducting And Thermally Stable pi−Conjugated Poly(arylene)s Prepared by Organometallic Processes」,Progress in Polymer Science 1993,17,1153−1205に記載されるようなYamamoto重合である。Yamamoto重合の場合、ニッケル錯体触媒が使用される;Suzuki重合の場合、パラジウム錯体触媒が使用される。
OLEDの発光層に使用するために好適な発光材料としては、小分子、ポリマー性およびデンドリマー性材料並びにそれらの組成物が挙げられる。好適な発光ポリマーとしては、共役ポリマー、例えば置換または非置換ポリ(アリーレンビニレン)、例えばポリ(p−フェニレンビニレン)および置換または非置換ポリアリーレン、例えば:ポリフルオレン、特に2,7−連結9,9ジアルキルポリフルオレンまたは2,7−連結9,9ジアリールポリフルオレン;ポリスピロフルオレン、特に2,7−連結ポリ−9,9−スピロフルオレン;ポリインデノフルオレン、特に2,7−連結ポリインデノフルオレン;ポリフェニレン、特にアルキルまたはアルコキシ置換ポリ−1,4−フェニレンが挙げられる。かかるポリマーは、例えばAdv.Mater.2000 12(23)1737−1750およびこの文献の参照文献に開示される。上記で記載されるような式(I)の繰り返しユニットを含むポリマーは、発光材料として、または蛍光もしくはりん光ドーパントのためのホストとして、OLEDの発光層に提供されてもよい。
ML1 qL2 rL3 s
(X)
式中、Mは金属であり;L1、L2およびL3のそれぞれは、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;(a.q)+(b.r)+(c.s)の合計は、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。
ホール輸送層は、アノードと発光層との間に提供されてもよい。同様に、電子輸送層が、カソードと発光層との間に提供されてもよい。
伝導性の有機または無機材料から形成されてもよい伝導性ホール注入層は、図1に示されるようなアノード2と発光層3との間に提供されて、アノードから半導体性ポリマーの層へのホール注入を補助してもよい。ドープされた有機ホール注入材料の例としては、置換されていてもよいドープされたポリ(エチレンジオキシチオフェン)(PEDT)、特に欧州特許第0901176号明細書および同第0947123号明細書に開示されるような電荷平衡化ポリ酸、例えばポリスチレンスルホネート(PSS)でドープされたPEDT、ポリアクリル酸またはフッ素化スルホン酸、例えばNafion(登録商標);米国特許第5723873号明細書および米国特許第5798170号明細書に開示されるようなポリアニリン;および置換されていてもよいポリチオフェンまたはポリ(チエノチオフェン)が挙げられる。伝導性無機材料の例としては、遷移金属酸化物、例えばJournal of Physics D:Applied Physics(1996),29(11),2750−2753に開示されるようなVOx、MoOxおよびRuOxが挙げられる。
カソードは、電子を、発光層に注入させる仕事関数を有する材料から選択される。カソードと発光材料との間の不利な相互作用の可能性のような他の要因が、カソードの選択に影響する。カソードは、アルミニウム層のような単一材料からなってもよい。別の方法としてそれは、複数の金属を含んでいてもよく、例えば低仕事関数材料および高仕事関数材料の二層、例えば国際公開第98/10621号に開示されるようなカルシウムおよびアルミニウム;国際公開第98/57381号、Appl.Phys.Lett.2002,81(4),634および国際公開第02/84759号に開示されるような元素状バリウム;または電子注入を補助するために金属化合物、特にアルカリまたはアルカリ土類金属の酸化物またはフッ化物の薄層、例えば国際公開第00/48258号に開示されるようなフッ化リチウム;Appl.Phys.Lett.2001,79(5),2001に開示されるようなフッ化バリウム;および酸化バリウムを含んでいてもよい。効率の良い電子のデバイスへの注入を得るために、カソードは、好ましくは3.5eV未満、より好ましくは3.2eV未満、最も好ましくは3eV未満の仕事関数を有する。金属の仕事関数は、例えばMichaelson,J.Appl.Phys.48(11),4729,1977に見出されることができる。
有機光電子デバイスは、湿分および酸素に対して感受性の傾向がある。従って、基板は、好ましくは湿分および酸素のデバイスへの侵入を防止するために良好なバリア特性を有する。基板は、一般にガラスであるが、特にデバイスの可撓性が所望される場合には代替基板が使用されてもよい。例えば、基板は、1つ以上のプラスチック層、例えば代替プラスチックおよび誘電体バリア層の基板、または薄いガラスおよびプラスチックのラミネートを含んでいてもよい。
溶液加工処理のためのポリマー組成物を形成するのに好適な溶媒としては、一般的な有機溶媒が挙げられ、モノ−またはポリ−アルキルベンゼン、例えばトルエンおよびキシレン等が挙げられる。
比較モノマー1をモノマー実施例1の代わりに使用した以外、ポリマー実施例3に記載される通りに、ポリマーを調製した。
比較モノマー2をモノマー実施例1の代わりに使用した以外、ポリマー実施例3に記載される通りに、ポリマーを調製した。
以下の構造を有するデバイスを形成した:
ITO/HIL/HTL/EL/カソード
ここで、ITOはインジウムスズオキシドアノードであり、HILはホール注入層であり、HTLはホール輸送層であり、ELは発光層である。
デバイスを一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、ポリマー実施例1をスピンコーティングし、且つ、架橋することによって形成した。
デバイスを、一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、比較ポリマー1をスピンコーティングし、且つ、架橋することによって形成した。
デバイスを、一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、ポリマー実施例2をスピンコーティングし、且つ、架橋することによって形成した。
デバイスを、一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、比較ポリマー2をスピンコーティングし、且つ、架橋することによって形成した。
発光層が存在せず、カソードが上記デバイス実施例に比べて電子の注入が低下したアルミニウムである以外、ポリマー実施例1およびポリマー実施例2を用いる一般的なデバイス製作プロセスにおいて記載されるようにデバイスを作製した。
デバイスは、一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、ポリマー実施例3をスピンコーティングし、且つ、架橋することによって形成した。
比較ポリマー3Aをポリマー実施例3の代わりに使用した以外、デバイス実施例3に記載される通りにデバイスを作製した。
比較ポリマー3Bをポリマー実施例3の代わりに使用した以外、デバイス実施例3に記載されるようにデバイスを作製した。
デバイスは、一般的なデバイス製作プロセスに従って作製したが、ここでこのホール輸送層は、発光層が、30重量%の緑色りん光エミッタ1と混合したポリマーホストシステムのスピンコーティングによって形成された以外は、ポリマー実施例3をスピンコーティングし、且つ、架橋することによって形成した:
比較ポリマー3Aをポリマー実施例3の代わりに使用した以外、デバイス実施例4に記載される通りに、デバイスを作製した。
比較ポリマー3Bをポリマー実施例3の代わりに使用した以外、デバイス実施例4に記載される通りに、デバイスを作製した。
以下の構造を有するデバイスを形成した:
ITO/HIL/HTL/EL/カソード
ここでITOはインジウムスズオキシドアノードであり、HILはホール注入層であり、HTLはホール輸送層であり、ELは発光層である。
Claims (19)
- R2が、置換若しくは非置換の分岐、線状または環式アルキル基であり、ここで1つ以上の非隣接C原子がO、S、NR5、C=Oまたは−COO−で置き換えられていてもよく、1つ以上のH原子がFまたはDで置き換えられていてもよく、R5はHまたは置換基である、請求項1に記載のポリマー。
- R1が、基−(Ar3)yによってフルオレンユニットに結合し、ここでAr3は、各出現において置換若しくは非置換の芳香族またはヘテロ芳香族基であり;yは少なくとも1であり;yが2より大きい場合、−(Ar3)yは、線状または分岐鎖のAr3基を形成する、請求項1または2に記載のポリマー。
- Ar3が、各出現において置換または非置換フェニルである、請求項1〜3のいずれか1項に記載のポリマー。
- Ar3は、F;CN;NO2;NR5 2;架橋性基;およびC1−20アルキルから選択される1つ以上の置換基で置換され、ここで1つ以上の非隣接C原子は、置換または非置換のアリールまたはヘテロアリール、O、S、NR5、C=Oまたは−COO−で置き換えられていてもよく、1つ以上のH原子は、FまたはDで置き換えられていてもよく、R5はHまたは置換基である、請求項3または4に記載のポリマー。
- 各nが独立に1〜3であり、
各mが独立に1〜3である、請求項1から5のいずれか一項に記載のポリマー。 - 各Ar1およびAr2が独立に、非置換または置換フェニルである、請求項1から6のいずれか一項に記載のポリマー。
- 少なくとも1つのAr2は、F;CN;NO2;NR5 2;架橋性基;C1−20アルキル基から選択される1つ以上の置換基で置換され、ここで1つ以上の非隣接C原子は、置換または非置換のアリールまたはヘテロアリール、O、S、NR5、C=Oまたは−COO−で置き換えられていてもよく、1つ以上のH原子は、FまたはDで置き換えられていてもよく、R5はHまたは置換基である、請求項1から7のいずれか一項に記載のポリマー。
- Ar2−N結合に対してオルトである少なくとも1つの(Ar2)mの少なくとも1つの位置が置換されている、請求項1から8のいずれか一項に記載のポリマー。
- 前記ポリマーの、式(I)の前記繰り返しユニットおよび/または1つ以上の共繰り返しユニットが、少なくとも1つの架橋性基で置換されている、請求項1から11のいずれか一項に記載のポリマー。
- 請求項1から12のいずれか一項に記載のポリマーを含む半導体層を具備する有機電子デバイス。
- アノードとカソードとの間に半導体層を具備する有機発光デバイスである、請求項13に記載の有機電子デバイス。
- 前記半導体層が、アノードと発光層との間のホール輸送層である、請求項14に記載の有機電子デバイス。
- 請求項1から12のいずれか一項に記載のポリマーと、少なくとも1つの溶媒とを含む、配合物。
- 請求項17に記載のモノマーを重合する工程を含む、請求項1から12のいずれか一項に記載のポリマーを形成する方法。
- 前記重合が、金属触媒の存在下で行われる、請求項18に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB1200619.3A GB201200619D0 (en) | 2012-01-16 | 2012-01-16 | Polymer |
GB1200619.3 | 2012-01-16 | ||
GB1208610.4 | 2012-05-16 | ||
GB201208610A GB201208610D0 (en) | 2012-01-16 | 2012-05-16 | Monomers, polymers and organic electronic devices |
PCT/GB2013/050088 WO2013108022A1 (en) | 2012-01-16 | 2013-01-16 | Polymer comprising an unsymmetric diarylaminofluoren unit |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015503671A JP2015503671A (ja) | 2015-02-02 |
JP2015503671A5 JP2015503671A5 (ja) | 2016-03-03 |
JP6129207B2 true JP6129207B2 (ja) | 2017-05-17 |
Family
ID=45814024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014551681A Active JP6129207B2 (ja) | 2012-01-16 | 2013-01-16 | 非対称ジアリールアミンフルオレンユニットを含むポリマー |
Country Status (8)
Country | Link |
---|---|
US (3) | US9859499B2 (ja) |
EP (1) | EP2804927B1 (ja) |
JP (1) | JP6129207B2 (ja) |
KR (1) | KR102013007B1 (ja) |
CN (1) | CN104053747B (ja) |
GB (3) | GB201200619D0 (ja) |
TW (1) | TWI591095B (ja) |
WO (2) | WO2013108023A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11917899B2 (en) | 2020-03-05 | 2024-02-27 | Samsung Electronics Co., Ltd. | Arylamine-fluorene alternating copolymer, electroluminescence device material, and electroluminescence device using the polymer |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2687304B1 (en) * | 2011-03-17 | 2019-01-23 | Sumitomo Chemical Company Limited | Metal complex compositions and mixture thereof |
GB201200619D0 (en) * | 2012-01-16 | 2012-02-29 | Cambridge Display Tech Ltd | Polymer |
EP2875092B1 (de) * | 2012-07-23 | 2017-02-15 | Merck Patent GmbH | Verbindungen und organische elektrolumineszierende vorrichtungen |
GB201320881D0 (en) | 2013-11-26 | 2014-01-08 | Cambridge Display Tech Ltd | Organic light-emitting device and method |
GB2524747B (en) * | 2014-03-31 | 2017-03-01 | Cambridge Display Tech Ltd | Amine/fluorene copolymers and organic electronic devices comprising said copolymers |
EP3162467B1 (en) | 2014-06-30 | 2019-03-27 | NIPPON STEEL Chemical & Material Co., Ltd. | Nickel particle composition, bonding material, and bonding method in which said material is used |
GB2530748A (en) * | 2014-09-30 | 2016-04-06 | Cambridge Display Tech Ltd | Organic Light Emitting Device |
CN109196679B (zh) | 2015-12-01 | 2021-06-08 | 株式会社半导体能源研究所 | 发光元件、发光装置、电子设备及照明装置 |
KR102673970B1 (ko) * | 2016-10-13 | 2024-06-11 | 삼성디스플레이 주식회사 | 유기발광 표시장치 그 제조방법 |
GB2573338A (en) | 2018-05-04 | 2019-11-06 | Sumitomo Chemical Co | Device |
GB2581141A (en) | 2019-01-31 | 2020-08-12 | Sumitomo Chemical Co | Light-emitting composition |
KR102562219B1 (ko) * | 2019-02-18 | 2023-07-31 | 주식회사 엘지화학 | 신규한 고분자 및 이를 포함하는 유기 발광 소자 |
WO2024071042A1 (ja) * | 2022-09-30 | 2024-04-04 | 保土谷化学工業株式会社 | 化合物、正孔輸送材料、および該化合物を用いた光電変換素子 |
Family Cites Families (72)
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 |
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 Ltd | Elektrolumineszierende anordnungen mit elektrodenschutz |
CN1108730C (zh) | 1996-09-04 | 2003-05-14 | 剑桥显示技术有限公司 | 改进阴极的有机光发射器件 |
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 |
US6517957B1 (en) | 1997-05-19 | 2003-02-11 | Canon Kabushiki Kaisha | Organic compound and electroluminescent device using the same |
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 |
JP3821562B2 (ja) | 1997-12-18 | 2006-09-13 | 三井化学株式会社 | 有機電界発光素子 |
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 |
JP4505146B2 (ja) | 1999-02-04 | 2010-07-21 | ダウ グローバル テクノロジーズ インコーポレイティド | フルオレンコポリマーおよびそれから作られる素子 |
GB9903251D0 (en) | 1999-02-12 | 1999-04-07 | Cambridge Display Tech Ltd | Opto-electric devices |
EP1165648B1 (en) | 1999-03-05 | 2007-08-15 | Cambridge Display Technology Limited | Polymer preparation |
GB2348316A (en) | 1999-03-26 | 2000-09-27 | Cambridge Display Tech Ltd | Organic opto-electronic device |
JP4115056B2 (ja) | 1999-12-13 | 2008-07-09 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
JP4220644B2 (ja) | 2000-02-14 | 2009-02-04 | 三井化学株式会社 | アミン化合物および該化合物を含有する有機電界発光素子 |
JP2002040686A (ja) | 2000-07-24 | 2002-02-06 | Canon Inc | 電子写真感光体、該電子写真感光体を有するプロセスカートリッジおよび電子写真装置 |
US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
EP1348711B1 (en) | 2000-11-30 | 2018-06-13 | Canon Kabushiki Kaisha | Luminescent element and display |
EP1349435B8 (en) | 2000-11-30 | 2018-09-19 | Canon Kabushiki Kaisha | Luminescent element and display |
GB0031634D0 (en) | 2000-12-23 | 2001-02-07 | Johnson Matthey Plc | Organic materials |
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 |
US7592074B2 (en) | 2001-02-20 | 2009-09-22 | 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 |
AU2002246336B2 (en) | 2001-04-05 | 2005-05-19 | Sankyo Company, Limited | Benzamidine derivative |
EP1382075A1 (en) | 2001-04-17 | 2004-01-21 | 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 |
GB0111549D0 (en) * | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
JP2004067970A (ja) * | 2002-08-09 | 2004-03-04 | Tosoh Corp | 新規トリアリールアミンポリマー、その製造方法及びその用途 |
KR101014837B1 (ko) * | 2002-08-09 | 2011-02-15 | 도소 가부시키가이샤 | 신규 트리아릴아민폴리머, 그 제조방법 및 그 용도 |
TWI280973B (en) * | 2002-08-28 | 2007-05-11 | Sumitomo Chemical Co | Polymer compound and polymer light-emitting device using the same |
JP2004212959A (ja) | 2002-12-17 | 2004-07-29 | Canon Inc | 電子写真感光体、電子写真装置及びプロセスカートリッジ |
JP4032180B2 (ja) * | 2003-02-06 | 2008-01-16 | 東ソー株式会社 | 新規トリアリールアミンポリマー、その製造方法及びその用途 |
JP2005062301A (ja) * | 2003-08-08 | 2005-03-10 | Canon Inc | 電子写真感光体 |
US7651746B2 (en) * | 2003-11-14 | 2010-01-26 | Sumitomo Chemical Company, Limited | Halogenated bisdiarylaminopolycyclic aromatic compounds and polymers thereof |
TWI365218B (en) * | 2003-11-17 | 2012-06-01 | Sumitomo Chemical Co | Conjugated oligomers or polymers based on crosslinkable arylamine compounds |
JP2005169781A (ja) | 2003-12-10 | 2005-06-30 | Mitsui Chemicals Inc | 光記録媒体 |
JP2005208110A (ja) * | 2004-01-20 | 2005-08-04 | Canon Inc | 電子写真感光体、プロセスカートリッジおよび電子写真装置 |
DE102004020299A1 (de) * | 2004-04-26 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
US20090261711A1 (en) * | 2005-09-15 | 2009-10-22 | Idemitsu Kosan Co., Ltd. | Asymmetric fluorene derivative and organic electroluminescent element containing the same |
WO2007058368A1 (ja) * | 2005-11-18 | 2007-05-24 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
GB0526393D0 (en) * | 2005-12-23 | 2006-02-08 | Cdt Oxford Ltd | Light emissive device |
JP2007220772A (ja) * | 2006-02-15 | 2007-08-30 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス用高分子化合物及びその製造方法 |
KR101411789B1 (ko) * | 2006-09-25 | 2014-06-24 | 스미또모 가가꾸 가부시키가이샤 | 고분자 화합물 및 그것을 이용한 고분자 발광 소자 |
JP5281801B2 (ja) * | 2007-02-01 | 2013-09-04 | 住友化学株式会社 | ブロック共重合体および高分子発光素子 |
JP5281800B2 (ja) | 2007-02-01 | 2013-09-04 | 住友化学株式会社 | ブロック共重合体並びにそれを用いた組成物、液状組成物、発光性薄膜及び高分子発光素子 |
TW200902592A (en) | 2007-03-29 | 2009-01-16 | Mitsui Chemicals Inc | Polymers containing sulfo group and intermediate thereof, and organic electroluminescent element containing the polymer |
WO2008126393A1 (ja) * | 2007-04-04 | 2008-10-23 | Mitsui Chemicals, Inc. | スルホ基含有高分子化合物とその中間体、および該化合物を含有する有機電界発光素子 |
US20100140601A1 (en) * | 2007-05-23 | 2010-06-10 | Sumitomo Chemical Company, Limited | Polymer compound and method for producing the same, and light-emitting material, liquid composition, thin film, polymer light-emitting device, surface light source, display device, organic transistor and solar cell, each using the polymer compound |
JP2009016739A (ja) | 2007-07-09 | 2009-01-22 | Canon Inc | 有機発光素子及びその製造方法 |
US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
KR100940938B1 (ko) * | 2007-12-04 | 2010-02-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
EP2233508A4 (en) | 2007-12-11 | 2012-01-04 | Idemitsu Kosan Co | POLYMER COMPOUND AND ORGANIC ELECTROLUMINESCENT ELEMENT THEREWITH |
WO2009084548A1 (ja) | 2007-12-28 | 2009-07-09 | Idemitsu Kosan Co., Ltd. | 高分子化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
US8692234B2 (en) | 2008-04-02 | 2014-04-08 | Mitsubishi Chemical Corporation | Polymer compound, net-like polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescence element, organic electroluminescence element, organic EL display, and organic EL lighting |
JP5625271B2 (ja) * | 2008-07-29 | 2014-11-19 | 住友化学株式会社 | 高分子化合物及びそれを用いた発光素子 |
JP5417763B2 (ja) | 2008-08-08 | 2014-02-19 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用化合物 |
KR20110057078A (ko) * | 2009-11-23 | 2011-05-31 | 에스에프씨 주식회사 | 헤테로아릴아민 화합물 및 이를 포함하는 유기전계발광소자 |
JP2011151116A (ja) * | 2010-01-20 | 2011-08-04 | Canon Inc | 有機発光素子 |
CN102725325B (zh) * | 2010-01-28 | 2015-05-06 | 住友化学株式会社 | 高分子化合物及使用其而得到的发光元件 |
JP5505123B2 (ja) * | 2010-06-22 | 2014-05-28 | 東ソー株式会社 | 新規トリアリールアミンポリマー、その製造方法およびその用途 |
JP5883639B2 (ja) * | 2010-12-21 | 2016-03-15 | 住友化学株式会社 | 炭素クラスター構造を有する高分子化合物及びそれを用いた有機デバイス |
GB201200619D0 (en) * | 2012-01-16 | 2012-02-29 | Cambridge Display Tech Ltd | Polymer |
US9267003B2 (en) * | 2012-01-30 | 2016-02-23 | Sumitomo Chemical Company, Limited | Polymer compound, composition, and light-emitting device using the same |
GB201223369D0 (en) * | 2012-12-24 | 2013-02-06 | Cambridge Display Tech Ltd | Polymer and device |
EP2832761B1 (en) * | 2012-03-27 | 2020-11-18 | Sumitomo Chemical Company, Limited | Polymer compound and light emitting element using same |
GB201207866D0 (en) * | 2012-05-04 | 2012-06-20 | Cambridge Display Tech Ltd | Organic light emitting device and method |
GB201223283D0 (en) * | 2012-12-21 | 2013-02-06 | Cambridge Display Tech Ltd | Polymer and organic electronic device |
-
2012
- 2012-01-16 GB GBGB1200619.3A patent/GB201200619D0/en not_active Ceased
- 2012-05-16 GB GB201208610A patent/GB201208610D0/en not_active Ceased
-
2013
- 2013-01-16 KR KR1020147022389A patent/KR102013007B1/ko active IP Right Grant
- 2013-01-16 WO PCT/GB2013/050089 patent/WO2013108023A1/en active Application Filing
- 2013-01-16 CN CN201380005584.5A patent/CN104053747B/zh active Active
- 2013-01-16 WO PCT/GB2013/050088 patent/WO2013108022A1/en active Application Filing
- 2013-01-16 EP EP13703118.3A patent/EP2804927B1/en not_active Not-in-force
- 2013-01-16 US US14/372,529 patent/US9859499B2/en active Active
- 2013-01-16 JP JP2014551681A patent/JP6129207B2/ja active Active
- 2013-01-16 US US14/372,534 patent/US10396287B2/en active Active
- 2013-01-16 TW TW102101678A patent/TWI591095B/zh not_active IP Right Cessation
- 2013-01-16 GB GB1411212.2A patent/GB2513034B/en not_active Expired - Fee Related
-
2017
- 2017-11-21 US US15/819,811 patent/US10580992B2/en active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11917899B2 (en) | 2020-03-05 | 2024-02-27 | Samsung Electronics Co., Ltd. | Arylamine-fluorene alternating copolymer, electroluminescence device material, and electroluminescence device using the polymer |
Also Published As
Publication number | Publication date |
---|---|
US20140353652A1 (en) | 2014-12-04 |
EP2804927A1 (en) | 2014-11-26 |
KR102013007B1 (ko) | 2019-08-21 |
KR20140124770A (ko) | 2014-10-27 |
GB2513034A (en) | 2014-10-15 |
WO2013108023A1 (en) | 2013-07-25 |
GB2513034B (en) | 2020-03-11 |
GB201208610D0 (en) | 2012-06-27 |
GB201200619D0 (en) | 2012-02-29 |
US20150060798A1 (en) | 2015-03-05 |
US10396287B2 (en) | 2019-08-27 |
TWI591095B (zh) | 2017-07-11 |
US10580992B2 (en) | 2020-03-03 |
CN104053747B (zh) | 2016-11-16 |
US20180097183A1 (en) | 2018-04-05 |
GB201411212D0 (en) | 2014-08-06 |
TW201335231A (zh) | 2013-09-01 |
JP2015503671A (ja) | 2015-02-02 |
CN104053747A (zh) | 2014-09-17 |
EP2804927B1 (en) | 2016-08-31 |
WO2013108022A1 (en) | 2013-07-25 |
US9859499B2 (en) | 2018-01-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6129207B2 (ja) | 非対称ジアリールアミンフルオレンユニットを含むポリマー | |
JP6401711B2 (ja) | ポリマーおよびデバイス | |
JP6232052B2 (ja) | 有機発光デバイスおよび方法 | |
EP2794813B1 (en) | Light emitting composition and device | |
JP6225120B2 (ja) | ポリマー | |
WO2013005029A1 (en) | Organic light emitting composition, device and method | |
KR20120013385A (ko) | 유기 전기발광 소자 및 이의 제조 방법 | |
KR20180005203A (ko) | 발광 화합물 | |
WO2012153083A1 (en) | Light emitting material, composition and device | |
WO2013064814A1 (en) | Light emitting composition and device | |
US10290810B2 (en) | Polymer and organic electronic device | |
JP2017535070A (ja) | 有機発光デバイス | |
EP3227934B1 (en) | Organic light-emitting device | |
JP2014112674A (ja) | 有機発光デバイス | |
WO2016051144A1 (en) | Organic light emitting device | |
WO2015044656A1 (en) | Polymer and organic light emitting device |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160114 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160114 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20161026 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20161101 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20170126 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170202 |
|
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: 20170314 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170411 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6129207 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 |
|
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 |