JP2011074393A - 共役ポリマー - Google Patents
共役ポリマー Download PDFInfo
- Publication number
- JP2011074393A JP2011074393A JP2010277240A JP2010277240A JP2011074393A JP 2011074393 A JP2011074393 A JP 2011074393A JP 2010277240 A JP2010277240 A JP 2010277240A JP 2010277240 A JP2010277240 A JP 2010277240A JP 2011074393 A JP2011074393 A JP 2011074393A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- group
- monomer
- boronic acid
- mmol
- 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
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- 229920000642 polymer Polymers 0.000 title claims abstract description 84
- 239000000178 monomer Substances 0.000 claims description 52
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 14
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 11
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229920000547 conjugated polymer Polymers 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 150000004982 aromatic amines Chemical group 0.000 claims description 4
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910000085 borane Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 claims description 2
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- FGGAOQTXQHKQOW-UHFFFAOYSA-N n,n-diphenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 FGGAOQTXQHKQOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002954 polymerization reaction product Substances 0.000 claims description 2
- 125000006617 triphenylamine group Chemical group 0.000 claims 1
- 125000005264 aryl amine group Chemical group 0.000 abstract description 2
- 238000005401 electroluminescence Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000010410 layer Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
- -1 diboronic acid ester Chemical class 0.000 description 16
- 238000000576 coating method Methods 0.000 description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000004820 halides Chemical group 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
- 229920006254 polymer film Polymers 0.000 description 8
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 0 CCI(c(cc1C2(*)*)ccc1-c1c2cc(C(C)C)cc1)IC(C)(C)C Chemical compound CCI(c(cc1C2(*)*)ccc1-c1c2cc(C(C)C)cc1)IC(C)(C)C 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 125000005621 boronate group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VYCFLFGSEQTJGJ-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)-9h-fluorene Chemical compound C1=CC(OC)=CC=C1C1=CC=C2C3=CC=CC=C3CC2=C1C1=CC=C(OC)C=C1 VYCFLFGSEQTJGJ-UHFFFAOYSA-N 0.000 description 1
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N 2,7-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C3C2=C1 CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 1
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- BYDIWLYAWBNCAQ-UHFFFAOYSA-N 9,9-bis(4-methoxyphenyl)fluorene Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BYDIWLYAWBNCAQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- KESRRRLHHXXBRW-UHFFFAOYSA-N C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 Chemical compound C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 KESRRRLHHXXBRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102100029133 DNA damage-induced apoptosis suppressor protein Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000918646 Homo sapiens DNA damage-induced apoptosis suppressor protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- FJWADHMGHSBPOE-UHFFFAOYSA-N O1BOCC1C1=CC=CC=C1 Chemical compound O1BOCC1C1=CC=CC=C1 FJWADHMGHSBPOE-UHFFFAOYSA-N 0.000 description 1
- WAPVCEORUWWEBY-UHFFFAOYSA-N OBOS(C(C=C1)=CC=C1Br)(=O)=O Chemical compound OBOS(C(C=C1)=CC=C1Br)(=O)=O WAPVCEORUWWEBY-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000002739 cryptand Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000003097 hole (electron) Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- NXBOCOGLWBJRQC-UHFFFAOYSA-N methyl 3-[4-[4-(4-bromo-n-(3-methoxycarbonylphenyl)anilino)phenyl]-n-(4-bromophenyl)anilino]benzoate Chemical compound COC(=O)C1=CC=CC(N(C=2C=CC(Br)=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(Br)=CC=2)C=2C=C(C=CC=2)C(=O)OC)=C1 NXBOCOGLWBJRQC-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000002245 particle Substances 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 150000004655 tetrazenes Chemical class 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- 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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- Polymers & Plastics (AREA)
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Description
(a) ポリマーが少なくとも1パーセントの溶液を形成する有機溶媒、
(b) pKa が9〜13であって、濃度が少なくとも0.1Nである、無機塩基の水溶液、
(c) 触媒量のパラジウム錯体、及び
(d) 反応混合物中のボロン酸、ボロン酸エステル、及びボラン基のモル数を基準として少なくとも0.01モルパーセントの相間移動触媒
を含む反応混合物中において、
(i) ボロン酸、C1-C6ボロン酸エステル、C1-C6ボラン、及びこれらの組合せより選ばれる2つの反応性基を有するモノマーを芳香族ジハロゲン化物官能性モノマーと、又は(ii)1つの反応性ボロン酸、ボロン酸エステル、又はボラン基と1つの反応性ハロゲン化物官能性基を有するモノマーを互いに、対応する共役ポリマーが形成するに十分な反応条件において接触させることを含み、これらのモノマーは重合反応生成物が共役不飽和内部基を有するように選択されることを特徴とする方法により製造される。
R2は独立に、C1-C20ヒドロカルビル、C1-C20ヒドロカルビルオキシ、C1-C20チオエーテル、C1-C20ヒドロカルビルカルボニルオキシ、又はシアノであり、
R3は独立に、C1-C20ヒドロカルビル、ジ(C1-C20アルキル)アミノ、C1-C20ヒドロカルビルオキシもしくはC1-C20ヒドロカルビルで置換したC1-C20ヒドロカルビル、又はトリ(C1-C10アルキル)シロキシであり、
aは独立に0又は1であり、
Zは独立に、ボロン誘導体基である)
本発明のELデバイスは、6 Cd/Aほどのルミナンス効率で、50ボルト以下の電圧を加えた際に発光する。
対数粘度数はすべて、0.5g/dLのTHF溶液中で25℃において測定した。用いたモノマーの式を以下に示す。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、15.8g、29.49mmol)、2,7-ジブロモ-9,9-ジ-n-オクチルフルオレン(16.18g、29.49mmol、モノマー(2)、R=n-オクチル)、のトルエン(130mL)中の混合物に窒素下においてAliquat 336(1.5g、3.7mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.18g、0.15mmol)、及び2Mの炭酸ナトリウム水溶液(50mL、100mmol)を加えた。この混合物を激しく攪拌し、穏やかに2時間還流して加熱し、粘稠な混合物が観察された。さらに50mLのトルエンを加え、さらに15時間反応を続けた。次いで60mLのトルエンをこの粘稠な反応混合物に加え、さらに9時間加熱、攪拌を続けた。この最後において、2gのフェニルエチレンボロネートを加え、次いで15時間加熱し、1gのブロモベンゼンを加え、5時間加熱することによってポリマーをキャップした。この反応混合物を約60℃に冷却し、3Lのメタノールと300mLの脱イオン水の攪拌溶液にゆっくり加えた。濾過によって繊維状のポリマーを集め、メタノール(500mL)、脱イオン水(200mL)、及びメタノール(800mL)で連続して洗浄し、次いで真空オーブン内で60℃において10時間乾燥させた。ポリマーの重量は23gであった(収率100パーセント)。このポリマーの対数粘度数は1.50dL/gであった。ポリスチレン標準に対するゲル浸透クロマトグラフィーによる分子量測定では、148,000g/moleのMw及び47,980g/moleのMnを示した。このポリマーのスペクトル特性は以下の構造と一致した。
Aliquat 336を用いず、スケールを1/3にして実施例1の実験を繰り返した。60時間還流後に単離されたポリマーの極限粘度数は0.22dL/gであった。ポリスチレン標準に対するゲル浸透クロマトグラフィーによる分子量測定では、約13,000g/moleのMw及び約9,000g/moleのMnを示した。
9,9-ジ-n- オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、5.77g、10.87mmol)、4,7-ジブロモ-2,1,3-ベンゾチアジアゾール(3.20g、10.87mmol、モノマー(3))のトルエン(50mL)中の混合物に窒素下においてAliquat 336(1.1g、2.7mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.056g、0.045mmol)、及び2Mの炭酸ナトリウム水溶液(17mL、34mmol) を加えた。この混合物を激しく攪拌し、16時間還流して加熱した。フェニルボロネートとブロモベンゼンで末端キャップした後、黄色の繊維状の粒子としてコポリマーを単離した(5.7g、収率100パーセント)。このポリマーの対数粘度数は0.94dL/gであった。このポリマーのスペクトル特性は以下の構造と一致した。
Aliquat 336を用いずに、実施例2の実験を繰り返した。生成物の極限粘度数は0.14dL/gであった。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、3.20g、6.03mmol)、1,4-ジブロモナフタレン(モノマー(4)、1.725g、6.03mmol)のトルエン(40mL)中の混合物に窒素下においてテトラキス(トリフェニルホスフィン)パラジウム(0.12g、0.1mmol)、及び2Mの炭酸ナトリウム水溶液(12mL、24mmol)を加えた。この混合物を激しく攪拌し、16時間還流して加熱した。少量(0.05mL)を取り出し、10mLのメタノールに加えた。繊維状のポリマーの沈澱は観察されなかった。次いでこの反応混合物に1.0gのAliquat 336を加え、攪拌しさらに1時間加熱した。上記のように少量を取り出し、メタノールに加えると、オフホワイト色の繊維状のポリマーが沈澱した。さらに15時間後、メタノール中で沈澱させることによりポリマーを単離した(3.1g、収率100パーセント)。このポリマーの対数粘度数は0.39dL/gであった。このポリマーのスペクトル特性は以下の構造と一致した。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、6.40g、12.0mmol)、5,5'- ジブロモ-2,2'-バイチオフェン(モノマー(5)、4.00g、12.0mmol)のトルエン(80mL)中の混合物に窒素下においてテトラキス(トリフェニルホスフィン)パラジウム(0.18g、0.156mmol)、Aliquat 336(1.0g)、及び2Mの炭酸ナトリウム水溶液(24mL、48mmol)を加えた。この混合物を激しく攪拌し、24時間還流して加熱した。粘稠な反応混合物をアセトン(500mL)に注ぎ、繊維状の黄色のポリマーを沈澱させた。このポリマーを濾過によって集め、アセトンで洗浄し、真空オーブンにおいて60℃で一晩乾燥させた。このポリマーの対数粘度数は1.84dL/gであった。このポリマーのスペクトル特性は以下の構造と一致した。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、16.15g、30.9mmol)、N,N'-ジ(4-ブロモフェニル)-N,N'-ジ(3-カルボメトキシフェニル)ベンジジン(モノマー(6)、23.70g、30.0mmol)のトルエン(225mL)中の混合物に窒素下においてテトラキス(トリフェニルホスフィン)パラジウム(0.035g、0.03mmol)、Aliquat 336(2.6g)、及び2Mの炭酸ナトリウム水溶液(60mL、120mmol)を加えた。この混合物を激しく攪拌し、24時間還流して加熱した。通常の単離法によって、対数粘度数が1.40dL/gである繊維状のポリマーを得た。このポリマーのスペクトル特性は以下の構造と一致した。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(27.42g、51.2mmol)、2,7-ジブロモ-9,9-ジオクチルフルオレン(27.43g、50mmol)のトルエン(450mL)中の混合物に窒素下において、相間移動触媒であるAliquat 336(1.4g、3.4mmol)、テトラキス(トリフェニルホスフィン)パラジウム(38mg、0.032mmol)、及び2Mの炭酸ナトリウム水溶液(80mL、160mmol)を加えた。この混合物を攪拌し、穏やかに20時間還流して加熱すると、粘稠な反応混合物が観察された。1gのブロモベンゼンを加え、5時間攪拌、加熱を続けた。この反応混合物を約50℃に冷却し、3.5Lのメタノールと200mの1NのHCl水溶液の激しく攪拌した混合物にゆっくり加えた。濾過によってポリマー繊維を集め、メタノール(1L)、脱イオン水(500mL)、及びメタノール(1L)で連続して洗浄し、真空オーブンにおいて60℃で16時間乾燥させた。このポリマーの重量は39gであった(収率100パーセント)。このポリマーの対数粘度数は1.65dL/gであった(THF、25℃、0.5g/dL)。このポリマーのトルエン溶液をシリカゲルのカラムに通し、4Lのメタノールから再沈澱させることにより、このポリマーを精製した。精製したポリマーの重量は37gであった(収率95パーセント)。
9,9-ジ-n-オクチルフルオレン-2,7-ジ(エチレンボロネート)(モノマー(1)、R=n-オクチル、3.26g、6.15mmol)、2,7-ジブロモ-9,9-ジ(4-メトキシフェニル)フルオレン(モノマー(2)、R=4-メトキシフェニル、3.22g、6.00mmol)のトルエン(60mL)中の混合物にAliquat 336(0.8g)、テトラキス(トリフェニルホスフィン)パラジウム(13.8mg、0.012mmol、0.2モルパーセント)、及び2Mの炭酸ナトリウム水溶液(14mL、28mmol)を加えた。この混合物を激しく攪拌し、22時間穏やかに還流して加熱すると、粘稠な反応混合物が観察された。この最後において、1gのブロモベンゼンを加え、5時間加熱することにより、このポリマーをキャップした。この反応混合物を約60℃に冷却し、2Lのメタノールと200mLの脱イオン水の攪拌した溶液にゆっくり加えた。濾過によって繊維状のポリマーを集め、メタノール(200mL)、脱イオン水(100mL)、及びメタノール(200mL)で連続して洗浄した。次いで真空オーブンにおいて60℃で10時間乾燥させた。このポリマーの重量は4.1gであった(収率99パーセント)。このポリマーの対数粘度数は1.2dL/gであった。このポリマーのスペクトル特性は以下の構造と一致した。
Claims (8)
- 前記3級アリールアミンがトリフェニルアミン、N,N'-ジフェニルベンジジン、N,N'-ジフェニル-1,4-フェニレンジアミン、又はジフェニルナフチルアミンである、請求項1記載のポリマー。
- (a) ポリマーが少なくとも1パーセントの溶液を形成する有機溶媒、
(b) pKa が9〜13であって、濃度が少なくとも0.1Nである、無機塩基の水溶液、
(c) 触媒量のパラジウム錯体、及び
(d) 反応混合物中のボロン酸、ボロン酸エステル、及びボラン基のモル数を基準として少なくとも0.01モルパーセントの相間移動触媒
を含む反応混合物中において、
(i) ボロン酸、C1-C6ボロン酸エステル、C1-C6ボラン、及びこれらの組合せより選ばれる2つの反応性基を有するモノマーを芳香族ジハロゲン化物官能性モノマーと、又は(ii)1つの反応性ボロン酸、ボロン酸エステル、又はボラン基と1つの反応性ハロゲン化物官能性基を有するモノマーを互いに、対応する共役ポリマーが形成するに十分な反応条件において接触させることを含み、これらのモノマーは重合反応生成物が共役不飽和内部基を有するように選択されることを特徴とする方法により製造される、請求項1〜3のいずれか1項に記載のポリマー。 - 末端アリール基を有する、請求項1〜4のいずれか1項に記載のポリマー。
- 前記アリール基がベンゼンである、請求項5記載のポリマー。
- 請求項1〜6のいずれか1項に記載のポリマーを含むフィルム。
- 請求項1〜6のいずれか1項に記載のポリマーを含む有機エレクトロルミネッセンスデバイス。
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Also Published As
Publication number | Publication date |
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JP2009001807A (ja) | 2009-01-08 |
EP1025142A1 (en) | 2000-08-09 |
KR20010031366A (ko) | 2001-04-16 |
DE69811703D1 (de) | 2003-04-03 |
EP1025142B1 (en) | 2003-02-26 |
JP2010001494A (ja) | 2010-01-07 |
JP2009132924A (ja) | 2009-06-18 |
JP2001520289A (ja) | 2001-10-30 |
JP4616371B2 (ja) | 2011-01-19 |
TW412544B (en) | 2000-11-21 |
CN1231515C (zh) | 2005-12-14 |
WO1999020675A1 (en) | 1999-04-29 |
JP4390385B2 (ja) | 2009-12-24 |
JP5068365B2 (ja) | 2012-11-07 |
JP2010090393A (ja) | 2010-04-22 |
ATE233288T1 (de) | 2003-03-15 |
JP4616384B2 (ja) | 2011-01-19 |
KR100604625B1 (ko) | 2006-07-28 |
DE69811703T2 (de) | 2003-10-16 |
US5777070A (en) | 1998-07-07 |
JP4850292B2 (ja) | 2012-01-11 |
CN1276806A (zh) | 2000-12-13 |
CA2305137A1 (en) | 1999-04-29 |
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