JP2013538190A - 金属錯体 - Google Patents
金属錯体 Download PDFInfo
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- JP2013538190A JP2013538190A JP2013519972A JP2013519972A JP2013538190A JP 2013538190 A JP2013538190 A JP 2013538190A JP 2013519972 A JP2013519972 A JP 2013519972A JP 2013519972 A JP2013519972 A JP 2013519972A JP 2013538190 A JP2013538190 A JP 2013538190A
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- 150000004696 coordination complex Chemical class 0.000 title abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 112
- 229910052751 metal Inorganic materials 0.000 claims abstract description 67
- 239000002184 metal Substances 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 239000000126 substance Substances 0.000 claims abstract description 6
- 239000003446 ligand Substances 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 77
- -1 NR 8 Inorganic materials 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 239000000243 solution Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 11
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003384 small molecules Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 238000007639 printing Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- 239000003574 free electron Substances 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000879 imine group Chemical group 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 239000010408 film Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000002921 oxetanes Chemical class 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 229910000074 antimony hydride Inorganic materials 0.000 claims description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 239000010410 layer Substances 0.000 description 90
- 150000003254 radicals Chemical group 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000463 material Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000011159 matrix material Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 229920006037 cross link polymer Polymers 0.000 description 7
- 239000000412 dendrimer Substances 0.000 description 7
- 229920000736 dendritic polymer Polymers 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000005259 triarylamine group Chemical group 0.000 description 7
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 238000007740 vapor deposition Methods 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- 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 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000010948 rhodium Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 3
- IGEOJLLSRMEXLW-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-bis(3-phenylphenyl)-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 IGEOJLLSRMEXLW-UHFFFAOYSA-N 0.000 description 3
- VKIJXFIYBAYHOE-UHFFFAOYSA-N 2-phenylethenylboronic acid Chemical compound OB(O)C=CC1=CC=CC=C1 VKIJXFIYBAYHOE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- OJOSABWCUVCSTQ-UHFFFAOYSA-N cyclohepta-2,4,6-trienylium Chemical compound C1=CC=C[CH+]=C[CH]1 OJOSABWCUVCSTQ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
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- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- PMZLFYBZWYRRAZ-UHFFFAOYSA-N tricyclohexylarsane Chemical compound C1CCCCC1[As](C1CCCCC1)C1CCCCC1 PMZLFYBZWYRRAZ-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- QZBJYTDDWVXFDF-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)arsane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[As](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QZBJYTDDWVXFDF-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- YSPBORFVJLIOMX-UHFFFAOYSA-N tritert-butylarsane Chemical compound CC(C)(C)[As](C(C)(C)C)C(C)(C)C YSPBORFVJLIOMX-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical compound CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(2)電極(金属または無機であることが多いが、また有機またはポリマー伝導性材料を含む)、
(3)電荷注入層(複数可)または中間層(複数可)(たとえば、電極の不均一さの均等化のため(「平坦化層」)、伝導性のドープしたポリマーを含むことが多い)、
(4)少なくとも1種のエミッターおよび少なくとも1種のマトリックス材料、またはエミッターとしておよびマトリックス材料として同時に作用する材料を通常含む発光層、
(5)任意にさらなる電荷輸送、電荷注入または電荷遮断層、
(6)対電極((2)で言及したような材料)、
(7)カプセル封入。
Mは、金属であり、
Xは、出現する毎に、同じくまたは異なって、CおよびNからなる群から選択され、ここでの全てのXは一緒になって、14個のπ電子系を表し、
R1〜R7は、出現する毎に、同じくまたは異なって、重合可能な基PGまたはH、D、F、Cl、Br、I、N(R8)2、CN、NO2、Si(R8)3、B(OR8)2、C(=O)R8、P(=O)(R8)2、S(=O)R8、S(=O)2R8、OSO2R8、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40個のC原子を有するアルケニル、アルキニルもしくはイミン基、または3〜40個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルコキシ基であり、ここで、上記のアルキル、アルコキシ、チオアルコキシ、アルケニル、アルキニルおよびイミン基は、各々、1個以上のラジカルR8で置換されていてもよく、ここで、1個以上の隣接していないCH2基は、R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、C=NR8、P(=O)(R8)、SO、SO2、NR8、O、SまたはCONR8によって置きかえられていてもよく、ここで、1個以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2、または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1個以上のラジカルR8で置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1個以上のラジカルR8で置換されていてもよい)、または5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基(これらは、1個以上のラジカルR8で置換されていてもよい)、または10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基(これらは、1個以上のラジカルR8で置換されていてもよい)によって置きかえられていてもよく、ここでのR1およびR2ならびに/またはR2およびR3ならびに/またはR4およびR5ならびに/またはR5およびR6ならびに/またはR6およびR7はまた、単環式または多環式の脂肪族、芳香族および/またはベンゾ縮合環系を互いに形成してもよく、さらに、R3およびR4は、各場合において単環式または多環式の、脂肪族環系を互いに形成してもよく、
ただし、R1、R2、R3、R4、R5、R6またはR7は、このラジカルR1、R2、R3、R4、R5、R6またはR7が結合している基Xが、飽和原子価を有する窒素原子である場合、自由電子対を表し、
R8は、出現する毎に、同じくまたは異なって、H、D、F、Cl、Br、I、N(R9)2、CN、NO2、Si(R9)3、B(OR9)2、C(=O)R9、P(=O)(R9)2、S(=O)R9、S(=O)2R9、OSO2R9、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40個のC原子を有するアルケニルもしくはアルキニル基、または3〜40個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルコキシ基(これらの各々は、1個以上のラジカルR9で置換されていてもよい)であり、ここで、1個以上の隣接していないCH2基は、R9C=CR9、C≡C、Si(R9)2、Ge(R9)2、Sn(R9)2、C=O、C=S、C=Se、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、SまたはCONR9によって置きかえられていてもよく、ここで、1個以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2、または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1個以上のラジカルR9で置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1個以上のラジカルR9で置換されていてもよい)、または5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基(これらは、1個以上のラジカルR8で置換されていてもよい)、または10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基(これらは、1個以上のラジカルR9で置換されていてもよい)によって置きかえられていてもよく、ここでの2個以上の隣接しているラジカルR8は、単環式または多環式の脂肪族または芳香族環系を互いに形成してもよく、
R9は、出現する毎に、同じくまたは異なって、H、D、F、CN、または1〜20個のC原子を有する脂肪族、芳香族および/もしくはヘテロ芳香族炭化水素ラジカルであり、ここでさらに、1個以上のH原子は、DまたはFによって置きかえられていてもよく、ここでの2個以上の置換基R9はまた、単環式または多環式の脂肪族または芳香族環系を互いに形成してもよく、
PGは、重合可能な基であり、ただし、重合可能な基は、Cl、Br、IおよびB(OR8)2から選択されず、さらにただし、重合可能な基PGとしてのラジカルR1〜R7の1個以上が、アルケニルまたはアルキニル基から選択される場合、これは3〜40個のC原子を有する末端アルケニルまたはアルキニル基であり、ここで、個々のCH2基または個々のH原子はまた、R1〜R7の場合において言及した基によって置きかえられていてもよく、さらにただし、重合可能な基PGとしてのラジカルR1〜R7の1個以上が、基Si(R8)3から選択される場合、R8は、Clまたは1〜40個のC原子を有するアルコキシ基の何れかを表し、
L’は、同じくまたは異なって、出現する毎に、任意の所望の共配位子であり、
nは、1、2または3であり、
mは、0、1、2、3または4であり、
ここでの複数の配位子Lはまた、互いに連結していてもよく、またはLは、単結合または任意の所望の架橋Vを介してL’に連結していてもよく、したがって三座、四座、五座または六座の配位子系を形成し、
ラジカルR1〜R7の少なくとも1個および/または配位子L’上の少なくとも1個のラジカルは、重合可能な基PGを表すことを特徴とする]。
X1は、同じくまたは異なって、出現する毎に、CまたはNであり、ただし、少なくとも1個の基X1は、Nを表す]。
Yは、同じくまたは異なって、出現する毎に、CR8またはNであり、ただし、最大で2つの記号Yは、Nを表し、
X2は、同じくまたは異なって、出現する毎に、CまたはNであり、ただし、正確に2つの記号X2は、Nを表し、残りの記号X2は、Cを表す]。
2〜40個のC原子を有し、好ましくは2〜10個のC原子を有するアルケニルまたはアルキニル基(ここでさらに、個々のCH2基および/または個々のH原子は、R1〜R7の場合における上記の基によって置きかえられていてもよい)が適している。基R1〜R7の1個以上が、重合可能なアルケニルまたはアルキニル基として選択される場合、これらは、3〜40個のC原子を有し、好ましくは3〜10個のC原子を有するアルケニル基(末端二重結合を有する)、または3〜40個のC原子を有し、好ましくは3〜10個のC原子を有するアルキニル基(末端三重結合を有する)である。末端アルケニルまたはアルキニル基中の個々のCH2基はまた、ここでR1〜R7の場合における上記の基によって置きかえられていてもよい。
さらなる適切なクラスの重合可能な基は、開環によってカチオン的に重合するオキセタンおよびオキシランである。したがってたとえば、下記の基が適しており、ここで、錯体への連結は、これらの基の各々において、Rによって示され、これらの基は、各々、1個以上のラジカルR8で置換されていてもよい。
このクラスの重合可能な基において、適切な基は、たとえば、1,3−双極性付加反応を受けるものである。ここで、反応は、2つの相補的基の間に起こる(たとえば、アジドと末端アルケニルまたはアルキニル基との反応)。したがって、式(1)の化合物は、このタイプの反応を受けることができる少なくとも2個の基を有さなくてはならない。次いで、重合は、下記の一般スキームに従って進行し、ここで、Rは一般に、金属錯体を表し、*は、ポリマーにおける連結を示し、さらなるコモノマーをまた当然ながら用いてもよい。
さらに、互いに重縮合反応を受ける基は、重合可能な基のクラスとして適している。特に、アミンまたはアルコールと反応するカルボン酸誘導体は、ここで適している。適切なカルボン酸誘導体は、たとえば、カルボン酸、カルボン酸エステルまたはカルボン酸塩化物である。さらなる適切な反応物は、たとえば、ジチオール、ジオキシラン、塩化ジスルフリルまたはジイソシアネートである。したがって、たとえば、下記の基が適しており、ここで、金属錯体を、これらの基の各々において、Rによって示す。
さらに、シラン基Si(R8)3は、重合可能な基のクラスとして適しており、ここで、少なくとも2個の基R8、好ましくは3個の基R8の全ては、Clまたは1〜20個のC原子を有するアルコキシ基を表す。この基は、水の存在下で反応し、ポリシロキサンが得られる。2個または3個のこのような基R8がシラン基において結合しているかによって、そこから発生するポリマーは、線状ポリマーまたは架橋ポリマーである。
群2:電子注入および/または電子輸送特性を有する単位;
群3:電気リン光を示す単位;
群4:一重項から三重項状態への転移を改善する単位;
群5:生成したポリマーの発光色に影響を与える単位;
群6:ポリマー骨格として典型的には使用する単位;
群7:生成したポリマーのフィルム形態および/またはレオロジー特性に影響を与える単位。
下記の合成は、他に示さない限り、保護ガス雰囲気下にて乾燥溶媒中で行う。金属錯体を、光を排除してさらに処理する。溶媒および試薬は、たとえば、Sigma−ALDRICHまたはABCRから購入することができる。配位子L1からL7の合成は、まだ出願公開されていない出願EP10006208.2に記載されている。ナフト[1’,2’:4,5]イミダゾ[1,2−a]ピリジン、[239−25−8]、L9は、G.Morganら、J.Chem.Soc.、1057、1939によって調製する。
1000mlのo−キシレン中の81.8g(500mmol)の1−クロロイソキノリン[19493−44−8]、120.7g(520mmol)の2−ブロモ−3−メトキシメトキシフェニル−アミン、172.8g(1250mmol)の炭酸カリウム、200gのガラスビーズ(直径3mm)、2.6g(10mmol)のトリフェニルホスフィンおよび449mg(2mmol)の酢酸パラジウム(II)の激しく撹拌した混合物を、1−クロロイソキノリンが消費されるまで16時間加熱還流させる。冷却後、シリカゲル床を通して混合物を濾過し、1000mlのTHFですすぎ、濾液を蒸発乾固させる。残渣を500mlのTHFに溶解し、50mlの塩酸(0.1N)を加え、混合物を60℃で6時間撹拌する。冷却後、THFを真空中で除去し、残渣をエタノールから3回再結晶させる。収量:63.1g(269mmol)、54%。純度:99.5%(HPLC)。
バリアントA:
ステップ1:
10mmolのナトリウムビスアセチルアセトナトジクロロイリデート(bisacetylacetonatodichloroiridate)(III)[770720−50−8]および24mmolの配位子Lの混合物を、50mlのガラス製アンプルに真空中(10-3ミリバール)で溶融する。アンプルを示された時間について示された温度で加熱し、その間に磁気撹拌機を活用して溶融した混合物を撹拌する。冷却後(注:アンプルは通常加圧下である!)、アンプルを開け、シンターケーキを100mlのジクロロメタン中で100gのガラスビーズ(直径3mm)と共に3時間撹拌し、工程において機械的に消化する。微細懸濁液をガラスビーズからデカントし、固体を吸引によって濾過し、真空中で乾燥させる。
このようにして得た式[Ir(L)2Cl]2の粗クロロ架橋二量体を、300mlのアセトンに懸濁させ、4.4g(20mmol)の銀(I)トリフルオロアセテート[2966−50−9]を懸濁液に加え、混合物を2時間加熱還流させる。冷却後、塩化銀沈殿物を濾過し(P4)、4.8g(22mmol)の6−(4−ビニルフェニル)−2,4−ヘキサンジオン[59990−76−0]、CL1、または3.3g(22mmol)の5−ビニル−2−ピリジンカルボン酸[45946−64−3]、CL2、または5.9g(22mmol)の3−[(4−ブロモフェニル)メチル]−2,4−ペンタンジオン[204927−96−8]、CL3、または4.1g(22mmol)の2,2,6,6−テトラメチル−3,5−ヘプタンジオン[1118−71−4]、CL4、および10mlのトリエチルアミンを濾液に加え、混合物を室温で20時間撹拌する。真空中でのアセトンの除去後、残渣を200mlのジクロロメタンに溶解し、約10cmの長さの酸化アルミニウムカラム(酸化アルミニウム、ベーシック、活性グレード1)を通して濾過する。濾液を蒸発させた後、残渣を、純度>99.5%、好ましくは99.9%超(HPLC)に達するまで、ジクロロメタンと共に酸化アルミニウム(酸化アルミニウム、ベーシック、活性グレード1)上でクロマトグラフにかける。
4.1)重合可能な基としてのスチリル基についての一般の重合手順
モノマーを、20mlのトルエン中の表1に示す組成物に1mol/lの濃度で80℃にて保護ガス下で溶解する。64mgのAlBNを続いて加え、混合物を80℃でさらに2時間撹拌する。反応溶液を室温に冷却し、ポリマーを、100mlのメタノール中での沈殿によって得る(パスツールピペットを使用してゆっくり)。沈殿物を吸引によって濾過し、続いてトルエンに再溶解し、メタノールに再び沈殿させ、吸引によって濾過する。ポリマーを、真空乾燥キャビネット中で乾燥させる。この重合手順を、ポリマーP1からP9について使用する。
モノマーを、20mlのトルエン中の表1に示す組成物に1mol/lの濃度で室温にて保護ガス下で溶解する。31mgのトロピリウムヘキサクロロアンチモネートを続いて加え、混合物を40℃でさらに5時間撹拌する。反応溶液を室温に冷却し、ポリマーを、100mlのメタノール中での沈殿によって得る(パスツールピペットを使用してゆっくり)。沈殿物を吸引によって濾過し、続いてトルエンに再溶解し、メタノールに再び沈殿させ、吸引によって濾過する。ポリマーを真空乾燥キャビネット中で乾燥させる。この重合手順を、ポリマーP10からP13について使用する。
ポリマー有機発光ダイオード(PLED)の生産は、文献(たとえば、WO2004/037887)において既に多数記載されてきた。本発明を例示として説明するために、PLEDは、表2からのポリマーP1からP11でスピンコーティングすることによって生産される。
Claims (17)
- 式(2)または式(3)の部分M(L)nを含有する式(1)の化合物
M(L)n(L’)m 式(1)
Mは、金属であり、
Xは、出現する毎に、同じくまたは異なって、CおよびNからなる群から選択され、ここでの全てのXは一緒になって、14個のπ電子系を表し、
R1〜R7は、出現する毎に、同じくまたは異なって、重合可能な基PGまたはH、D、F、Cl、Br、I、N(R8)2、CN、NO2、Si(R8)3、B(OR8)2、C(=O)R8、P(=O)(R8)2、S(=O)R8、S(=O)2R8、OSO2R8、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40個のC原子を有するアルケニル、アルキニルもしくはイミン基、または3〜40個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルコキシ基であり、ここで、上記のアルキル、アルコキシ、チオアルコキシ、アルケニル、アルキニルおよびイミン基は、各々、1個以上のラジカルR8で置換されていてもよく、ここで、1個以上の隣接していないCH2基は、R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、C=NR8、P(=O)(R8)、SO、SO2、NR8、O、SまたはCONR8によって置きかえられていてもよく、ここで、1個以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2、または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1個以上のラジカルR8で置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1個以上のラジカルR8で置換されていてもよい)、または5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基(これらは、1個以上のラジカルR8で置換されていてもよい)、または10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基(これらは、1個以上のラジカルR8で置換されていてもよい)によって置きかえられていてもよく、ここでのR1およびR2ならびに/またはR2およびR3ならびに/またはR4およびR5ならびに/またはR5およびR6ならびに/またはR6およびR7はまた、単環式または多環式の脂肪族、芳香族および/またはベンゾ縮合環系を互いに形成してもよく、さらに、R3およびR4は、各場合において単環式または多環式の、脂肪族環系を互いに形成してもよく、
ただし、R1、R2、R3、R4、R5、R6またはR7は、このラジカルR1、R2、R3、R4、R5、R6またはR7が結合している前記基Xが、飽和原子価を有する窒素原子である場合、自由電子対を表し、
R8は、出現する毎に、同じくまたは異なって、H、D、F、Cl、Br、I、N(R9)2、CN、NO2、Si(R9)3、B(OR9)2、C(=O)R9、P(=O)(R9)2、S(=O)R9、S(=O)2R9、OSO2R9、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40個のC原子を有するアルケニルもしくはアルキニル基、または3〜40個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルコキシ基(これらの各々は、1個以上のラジカルR9で置換されていてもよい)であり、ここで、1個以上の隣接していないCH2基は、R9C=CR9、C≡C、Si(R9)2、Ge(R9)2、Sn(R9)2、C=O、C=S、C=Se、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、SまたはCONR9によって置きかえられていてもよく、ここで、1個以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2、または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1個以上のラジカルR9で置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1個以上のラジカルR9で置換されていてもよい)、または5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基(これらは、1個以上のラジカルR8で置換されていてもよい)、または10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基(これらは、1個以上のラジカルR9で置換されていてもよい)によって置きかえられていてもよく、ここでの2個以上の隣接しているラジカルR8は、単環式または多環式の脂肪族または芳香族環系を互いに形成してもよく、
R9は、出現する毎に、同じくまたは異なって、H、D、F、CN、または1〜20個のC原子を有する脂肪族、芳香族および/もしくはヘテロ芳香族炭化水素ラジカルであり、ここでさらに、1個以上のH原子は、DまたはFによって置きかえられていてもよく、ここでの2個以上の置換基R9はまた、単環式または多環式の脂肪族または芳香族環系を互いに形成してもよく、
PGは、重合可能な基であり、ただし、前記重合可能な基は、Cl、Br、IおよびB(OR8)2から選択されず、さらにただし、重合可能な基PGとしての前記ラジカルR1〜R7の1個以上が、アルケニルまたはアルキニル基から選択される場合、これは3〜40個のC原子を有する末端アルケニルまたはアルキニル基であり、ここで、個々のCH2基または個々のH原子はまた、R1〜R7の場合における上記の基によって置きかえられていてもよく、さらにただし、重合可能な基PGとしての前記ラジカルR1〜R7の1個以上が、基Si(R8)3から選択される場合、R8は、Clまたは1〜40個のC原子を有するアルコキシ基の何れかを表し、
L’は、同じくまたは異なって、出現する毎に、共配位子であり、
nは、1、2または3であり、
mは、0、1、2、3または4であり、
ここでの複数の配位子Lはまた、互いに連結していてもよく、またはLは、単結合または架橋Vを介してL’に連結していてもよく、したがって三座、四座、五座または六座の配位子系を形成し、
前記ラジカルR1〜R7の少なくとも1個および/または前記配位子L’上の少なくとも1個のラジカルは、重合可能な基PGを表すことを特徴とする]。 - L’が、一酸化炭素、一酸化窒素、シアン化アルキル、シアン化アリール、イソシアン化アルキル、イソシアン化アリール、アミン、ホスフィン、アルシン、スチビン、窒素含有ヘテロ環、カルベン、ヒドリド、ジューテリド、ハライドF-、Cl-、Br-およびI-、アルキルアセチリド、アリールアセチリド、シアニド、シアネート、イソシアネート、チオシアネート、イソチオシアネート、脂肪族または芳香族アルコラート、脂肪族または芳香族チオアルコラート、アミド、カルボキシレート、アリール基、O2-、S2-、カーバイド、ニトレン、N3-、ジアミン、イミン、ジイミン、ジホスフィン、1,3−ジケトネート、3−ケトエステルに由来する3−ケトネート、アミノカルボン酸に由来するカルボキシレート、サリチルイミネート、ジアルコラート、ジチオレート、窒素含有ヘテロ環のボレート、ならびに金属と共に、少なくとも1つの金属−炭素結合を有する環状金属化5員環または6員環を形成する配位子からなる群から選択されることを特徴とする、請求項1〜6の何れか1項に記載の化合物。
- 前記重合可能な基PGが、2〜40個のC原子を有するアルケニルまたはアルキニル基(ここで、前記基R1〜R7の1個以上が、重合可能なアルケニルまたはアルキニル基として選択される場合、これらは、末端二重または三重結合を有する3〜40個のC原子を有するアルケニルまたはアルキニル基である)、オキセタン、オキシラン、多重環化付加を受ける基、カルボン酸誘導体、アミン、アルコール、シラン基Si(R8)3(ここで、少なくとも2個の基R8は、Clまたは1〜20個のC原子を有するアルコキシ基を表す)から選択されることを特徴とする、請求項1〜7の何れか1項に記載の化合物。
- 1個、2個または3個の重合可能な基PGを有することを特徴とする、請求項1〜8の何れか1項に記載の化合物。
- ポリマーの調製のための、請求項1〜9の何れか1項に記載の化合物の使用。
- 重合反応が、前記重合可能な基PGを介して起こる、請求項1〜9の何れか1項に記載の化合物、および任意にさらなるモノマーの重合によって得られるポリマー。
- 正孔注入および/または正孔輸送特性を有する単位、電子注入および/または電子輸送特性を有する単位、電気リン光を示す単位、一重項状態から三重項状態への転移を改善させる単位、生成したポリマーの発光色に影響を与える単位、骨格として使用される単位、ならびにポリマーのフィルム形態および/またはレオロジー特性に影響を与える単位から選択されるさらなる構造単位が存在することを特徴とする、請求項11に記載のポリマー。
- 請求項1〜9の何れか1項に記載の1種以上の化合物、および/または請求項11または12に記載の1種以上のポリマーを含む配合物。
- 電子デバイスにおける、請求項11または12に記載のポリマーの使用。
- 少なくとも1つの層において請求項11または12に記載の少なくとも1種のポリマーを含む、有機エレクトロルミネッセンスデバイス(OLED、PLED)、有機集積回路(O−IC)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機太陽電池(O−SC)、有機光学検波器、有機光受容体、有機電場消光デバイス(O−FQD)、発光電気化学セル(LEC)または有機レーザーダイオード(O−レーザー)からなる群から好ましくは選択される電子デバイス。
- 請求項11または12に記載のポリマーが、純粋な物質として、または1種以上のさらなるポリマーもしくは低分子量化合物との混合物中で、発光層において用いられることを特徴とする、請求項15に記載の有機エレクトロルミネッセンスデバイス。
- 請求項15または16に記載の電子デバイスの生産方法であって、請求項1〜9の何れか1項に記載の化合物を、任意にさらなるモノマーと一緒に、層として適用し、前記電子デバイスの前記層において重合および/または架橋させること、または請求項1〜9の何れか1項に記載の化合物を、任意にさらなるモノマーと一緒に、重合し、このポリマーを、層として溶液からまたは印刷工程によって適用することを特徴とする、方法。
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DE112011102372A5 (de) | 2013-04-25 |
DE102010027316A1 (de) | 2012-01-19 |
US9382253B2 (en) | 2016-07-05 |
JP5868972B2 (ja) | 2016-02-24 |
US20130112921A1 (en) | 2013-05-09 |
KR20130095258A (ko) | 2013-08-27 |
WO2012007087A1 (de) | 2012-01-19 |
CN102985433B (zh) | 2016-06-15 |
CN102985433A (zh) | 2013-03-20 |
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