JP4524901B2 - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP4524901B2 JP4524901B2 JP2000320569A JP2000320569A JP4524901B2 JP 4524901 B2 JP4524901 B2 JP 4524901B2 JP 2000320569 A JP2000320569 A JP 2000320569A JP 2000320569 A JP2000320569 A JP 2000320569A JP 4524901 B2 JP4524901 B2 JP 4524901B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- light
- derivatives
- light emitting
- compound
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 21
- 239000002019 doping agent Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 description 61
- 239000010410 layer Substances 0.000 description 34
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000011521 glass Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- -1 diamine compound Chemical class 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000005013 aryl ether group Chemical group 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000004832 aryl thioethers Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000005401 siloxanyl group Chemical group 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MUHOWKDSDKOADC-IYOYZZHUSA-N CC(C)(Cc1c-2cccc1)c1c-2[nH]c(/C(/c2ccccc2)=C(/C(C)=C2C(C)(C)C3)\N=C2c2c3cccc2)c1C Chemical compound CC(C)(Cc1c-2cccc1)c1c-2[nH]c(/C(/c2ccccc2)=C(/C(C)=C2C(C)(C)C3)\N=C2c2c3cccc2)c1C MUHOWKDSDKOADC-IYOYZZHUSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 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
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001893 coumarin derivatives Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005566 electron beam evaporation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 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
- 150000003377 silicon compounds Chemical group 0.000 description 2
- 239000005361 soda-lime glass Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- MCVPLAHRHVRSKV-UHFFFAOYSA-N 1,2-bis[2,3-di(propan-2-yl)phenyl]perylene Chemical group CC(C)C1=CC=CC(C=2C(=C3C=4C=CC=C5C=CC=C(C=45)C=4C=CC=C(C3=4)C=2)C=2C(=C(C(C)C)C=CC=2)C(C)C)=C1C(C)C MCVPLAHRHVRSKV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GHBQLFWTMLRYKN-UHFFFAOYSA-N 9-prop-2-enylcarbazole Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3C2=C1 GHBQLFWTMLRYKN-UHFFFAOYSA-N 0.000 description 1
- 101100410404 Arabidopsis thaliana PUMPKIN gene Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IWYPNMAKHGEFLH-ZIADKAODSA-N C(Cc1c-2cccc1)c1c-2[nH]c(/C(/c2ccccc2)=C(/C=C2CC3)\N=C2c2c3cccc2)c1 Chemical compound C(Cc1c-2cccc1)c1c-2[nH]c(/C(/c2ccccc2)=C(/C=C2CC3)\N=C2c2c3cccc2)c1 IWYPNMAKHGEFLH-ZIADKAODSA-N 0.000 description 1
- YAUJBOGEYOWGOQ-KTMFPKCZSA-N CC1=C(CCc2c3cccc2)C3=N/C1=C(\c1ccc(-c2cc(cccc3)c3[o]2)[nH]1)/c1ccccc1 Chemical compound CC1=C(CCc2c3cccc2)C3=N/C1=C(\c1ccc(-c2cc(cccc3)c3[o]2)[nH]1)/c1ccccc1 YAUJBOGEYOWGOQ-KTMFPKCZSA-N 0.000 description 1
- IEHMPAWHBYCKEQ-RQZHXJHFSA-N CC1=C(CCc2ccccc22)C2=N/C1=C(\c1ccc(-c2ccc[o]2)[nH]1)/c1ccccc1 Chemical compound CC1=C(CCc2ccccc22)C2=N/C1=C(\c1ccc(-c2ccc[o]2)[nH]1)/c1ccccc1 IEHMPAWHBYCKEQ-RQZHXJHFSA-N 0.000 description 1
- RWMAYDANRBAWDN-LLZINOMRSA-N CCc1c(/C(/c2ccccc2)=C(/C(CC)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 Chemical compound CCc1c(/C(/c2ccccc2)=C(/C(CC)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 RWMAYDANRBAWDN-LLZINOMRSA-N 0.000 description 1
- PXRIWZBCECLMGV-NHYZDEDTSA-N COc(cc1)ccc1-c1c(/C=C(/C(c(cc2)ccc2OC)=C2CC3)\N=C2c2c3cccc2)[n](CF)c-2c1CCc1c-2cccc1 Chemical compound COc(cc1)ccc1-c1c(/C=C(/C(c(cc2)ccc2OC)=C2CC3)\N=C2c2c3cccc2)[n](CF)c-2c1CCc1c-2cccc1 PXRIWZBCECLMGV-NHYZDEDTSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SLGMAEQHKHCKQL-OVJIMOTJSA-N Cc1c(/C(/c(cc2)ccc2-c2ccccc2)=C(/C(C)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 Chemical compound Cc1c(/C(/c(cc2)ccc2-c2ccccc2)=C(/C(C)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 SLGMAEQHKHCKQL-OVJIMOTJSA-N 0.000 description 1
- XRHBAINKBLJZJJ-FPODKLOTSA-N Cc1c(/C(/c2cc(C)cc(C)c2)=C(/C(C)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 Chemical compound Cc1c(/C(/c2cc(C)cc(C)c2)=C(/C(C)=C2CC3)\N=C2c2c3cccc2)[nH]c-2c1CCc1c-2cccc1 XRHBAINKBLJZJJ-FPODKLOTSA-N 0.000 description 1
- WXENERWNNKBVKO-OAPYJULQSA-N Cc1c(/C(/c2cc3ccccc3cc2)=C2\N=C3c4ccccc4CCC3=C2C)[nH]c-2c1CCc1ccccc-21 Chemical compound Cc1c(/C(/c2cc3ccccc3cc2)=C2\N=C3c4ccccc4CCC3=C2C)[nH]c-2c1CCc1ccccc-21 WXENERWNNKBVKO-OAPYJULQSA-N 0.000 description 1
- LDGYRBIYQNDTBP-YJKCNMNRSA-N Cc1c(/C(/c2ccc(C)cc2)=C(/C(C)=C2CC3)\N=C2c2c3cc(C)cc2)[nH]c-2c1CCc1cc(C)ccc-21 Chemical compound Cc1c(/C(/c2ccc(C)cc2)=C(/C(C)=C2CC3)\N=C2c2c3cc(C)cc2)[nH]c-2c1CCc1cc(C)ccc-21 LDGYRBIYQNDTBP-YJKCNMNRSA-N 0.000 description 1
- KLDHKYRQVDMDIF-OVJIMOTJSA-N Cc1c(/C(/c2ccccc2)=C(/C(C)=C2C3)\N=C2c2cccc4cccc3c24)[nH]c-2c1Cc1c3c-2cccc3ccc1 Chemical compound Cc1c(/C(/c2ccccc2)=C(/C(C)=C2C3)\N=C2c2cccc4cccc3c24)[nH]c-2c1Cc1c3c-2cccc3ccc1 KLDHKYRQVDMDIF-OVJIMOTJSA-N 0.000 description 1
- AHMVBYFERDVJPN-BZZOAKBMSA-N Cc1c(/C(/c2ccccc2)=C(/C(C)=C2N3)\N=C2c(cccc2)c2C3=O)[nH]c(-c2ccccc22)c1NC2=O Chemical compound Cc1c(/C(/c2ccccc2)=C(/C(C)=C2N3)\N=C2c(cccc2)c2C3=O)[nH]c(-c2ccccc22)c1NC2=O AHMVBYFERDVJPN-BZZOAKBMSA-N 0.000 description 1
- ZYHBNMRAQXVRJU-BZZOAKBMSA-N Cc1c(/C(/c2ccccc2)=C(/C(C)=C2O3)\N=C2c(cccc2)c2C3=O)[nH]c(-c2c3cccc2)c1OC3=O Chemical compound Cc1c(/C(/c2ccccc2)=C(/C(C)=C2O3)\N=C2c(cccc2)c2C3=O)[nH]c(-c2c3cccc2)c1OC3=O ZYHBNMRAQXVRJU-BZZOAKBMSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KWHWFTSHDPJOTG-UHFFFAOYSA-N Deazaflavin Chemical class C1=CC=C2C=C(C(=O)NC(=O)N3)C3=NC2=C1 KWHWFTSHDPJOTG-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機、光信号発生器などの分野に利用可能な発光素子に関するものである。
【０００２】
【従来の技術】
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機積層薄膜発光素子の研究が近年活発に行われている。この素子は、薄型、低駆動電圧下での高輝度発光、蛍光材料を選ぶことによる多色発光が特徴であり注目を集めている。
【０００３】
この研究はコダック社のＣ．Ｗ．Ｔａｎｇらが有機積層薄膜素子が高輝度に発光することを示して以来（Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１（１２）２１，ｐ．９１３，１９８７）、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機積層薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層である８−ヒドロキシキノリンアルミニウム、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ2の緑色発光が可能であった。現在の有機積層薄膜発光素子は、上記の素子構成要素の他に電子輸送層を設けているものなど構成を変えているものもあるが、基本的にはコダック社の構成を踏襲している。
【０００４】
多色発光の中でも赤色発光は、有用なる発光色として研究が進められている。従来、ビス（ジイソプロピルフェニル）ペリレンなどのペリレン系、ペリノン系、ポルフィリン系、Ｅｕ錯体（Ｃｈｅｍ．Ｌｅｔｔ．，１２６７（１９９１））などが赤色発光材料として知られている。
【０００５】
また、赤色発光を得る手法として、ホスト材料の中に微量の赤色蛍光材料をドーパントとして混入させる方法も検討されている。ホスト材料としては、トリス（８−キノリノラト）アルミニウム錯体、ビス（１０−ベンゾキノリノラト）ベリリウム錯体、ジアリールブタジエン誘導体、スチルベン誘導体、ベンズオキサゾール誘導体、ベンゾチアゾール誘導体などがあげられ、その中にドーパントとして４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピラン、金属フタロシアニン（ＭｇＰｃ、ＡｌＰｃＣｌなど）化合物、スクアリリウム化合物、ビオラントロン化合物を存在させることによって赤色発光を取り出していた。
【０００６】
また発光材料、特にドーパント材料として、高輝度発光を示す化合物のピロメテン化合物が知られている（特開平９−１１８８８０号公報）。また、ピロメテン骨格に芳香環等を導入することにより、赤色発光を示すことも知られている（特開２０００−２０８２６５号公報）。
【０００７】
【発明が解決しようとする課題】
従来技術に用いられる発光材料（ホスト材料、ドーパント材料）には、発光効率が低く消費電力が高いものや、化合物の耐久性が低く素子寿命の短いものが多かった。また、フルカラーディスプレイに必要な三原色の内、緑色発光においては高性能の発光材料が見い出されているが、青色や赤色、特に赤色においては十分な特性、とりわけ高輝度、高色純度の両方を満たす発光材料は得られていない。本発明は、かかる従来技術の問題を解決し、発光効率が高く、色純度に優れた赤色発光素子を提供することを目的とするものである。
【０００８】
【課題を解決するための手段】
すなわち本発明は、陽極と陰極の間に発光物質が存在し、電気エネルギーにより発光する素子であって、該素子が一般式（３）で表されるピロメテン化合物もしくはその金属錯体を発光層にドーパント材料として含むことを特徴とする発光素子である。
【０００９】
【化２】
（ここで、Ｒ ２３ 〜Ｒ ４０ はそれぞれ同じでも異なっていてもよく、水素、アルキル基の中から選ばれる。Ｒ ４１ はアリール基である。Ｒ ４２およびＲ４３はフッ素である。）
【００１１】
【発明の実施の形態】
本発明において陽極は、光を取り出すために透明であれば酸化錫、酸化インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロール、ポリアニリンなどの導電性ポリマなど特に限定されるものでないが、ＩＴＯガラスやネサガラスを用いることが特に望ましい。透明電極の抵抗は素子の発光に十分な電流が供給できればよいので限定されないが、素子の消費電力の観点からは低抵抗であることが望ましい。例えば３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。また、ガラス基板はソーダライムガラス、無アルカリガラスなどが用いられ、また厚みも機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用できる。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法、化学反応法など特に制限を受けるものではない。
【００１２】
陰極は、電子を本有機物層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、カルシウム、マグネシウムなどがあげられるが、電子注入効率をあげて素子特性を向上させるためにはリチウム、ナトリウム、カリウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかし、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができるが、フッ化リチウムのような無機塩の使用も可能であることから特にこれらに限定されるものではない。更に電極保護のために白金、金、銀、銅、鉄、錫、アルミニウム、インジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニア、窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子などを積層することが好ましい例として挙げられる。これらの電極の作製法も抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティング、コーティングなど導通を取ることができれば特に制限されない。
【００１３】
発光物質とは、１）正孔輸送層／発光層、２）正孔輸送層／発光層／電子輸送層、３）発光層／電子輸送層、４）正孔輸送層／発光層／正孔阻止層、５）正孔輸送層／発光層／正孔阻止層／電子輸送層、６）発光層／正孔阻止層／電子輸送層そして、７）以上の組合わせ物質を一層に混合した形態のいずれであってもよい。即ち、素子構成としては、上記１）〜６）の多層積層構造の他に７）のように発光材料単独または発光材料と正孔輸送材料や電子輸送材料を含む層を一層設けるだけでもよい。さらに、本発明における発光物質は自ら発光するもの、その発光を助けるもののいずれにも該当し、発光に関与している化合物、層などを指すものである。
【００１４】
正孔輸送層は正孔輸送性物質単独または二種類以上の物質を積層、混合するか正孔輸送性物質と高分子結着剤の混合物により形成され、正孔輸送性物質としてはＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミン、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミンなどのトリフェニルアミン類、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）類、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、オキサジアゾール誘導体やフタロシアニン誘導体、ポルフィリン誘導体に代表される複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリビニルカルバゾール、ポリシランなどが好ましいが、素子作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。
【００１５】
発光材料はホスト材料のみでも、ホスト材料とドーパント材料の組み合わせでも、いずれであってもよい。また、ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーパント材料は積層されていても、分散されていても、いずれであってもよい。
【００１６】
従来、ピロメテン化合物は発光材料、特にドーパント材料として、高輝度発光を示すことは知られており、また、ピロメテン骨格に芳香環等を導入することにより、赤色発光を示すことも知られている。しかし、発光輝度・色度ともに満足する赤色発光は得られていない。そこで本発明のピロメテン化合物は、赤色発光を得るためにピロメテン骨格に導入した芳香環（一般式（１）のＡｒ1およびＡｒ2）を、化学結合によりピロメテン骨格と連結し固定している。これにより、ピロメテン化合物の蛍光量子収率が向上し、かつ、発光スペクトルの半値幅が狭くなり、高輝度・高色純度の赤色発光を得ることを可能にしたものである。ピロメテン化合物としては、下記一般式（１）の化合物もしくはその金属錯体があげられる。
【００１７】
【化３】
ここで、Ｒ1〜Ｒ3はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される芳香族、脂肪族、あるいは複素環の縮合環の中から選ばれる。Ｘ1およびＸ2はそれぞれ同じでも異なっていてもよく、単結合、置換あるいは無置換のアルキレン結合、エーテル結合、スルフィド結合、置換あるいは無置換のアミノ結合、置換あるいは無置換のアミド結合、エステル結合、カルボニル結合の中から選ばれる。またＡｒ1およびＡｒ2は置換あるいは無置換のアリール基を表す。
【００１９】
これらの置換基の内、アルキル基とは例えばメチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルキル基とは例えばシクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アラルキル基とは例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、脂肪族炭化水素と芳香族炭化水素はいずれも無置換でも置換されていてもかまわない。また、アルケニル基とは例えばビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルケニル基とは例えばシクロペンテニル基、シクロペンタジエニル基、シクロヘキセン基などの二重結合を含む不飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルキニル基とは例えばアセチレニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルコキシ基とは例えばメトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。また、アルキルチオ基とはアルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリールエーテル基とは例えばフェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。また、アリールチオエーテル基とはアリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリール基とは例えばフェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、複素環基とは例えばフラニル基、チオフェニル基、オキサゾリル基、ピリジル基、キノリニル基、カルバゾリル基などの炭素以外の原子を有する環状構造基を示し、これは無置換でも置換されていてもかまわない。ハロゲンとはフッ素、塩素、臭素、ヨウ素を示す。ハロアルカン、ハロアルケン、ハロアルキンとは例えばトリフルオロメチル基などの、前述のアルキル基、アルケニル基、アルキニル基の一部あるいは全部が、前述のハロゲンで置換されたものを示し、残りの部分は無置換でも置換されていてもかまわない。アルデヒド基、カルボニル基、エステル基、カルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環などで置換されたものも含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環は無置換でも置換されていてもかまわない。シリル基とは例えばトリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。シロキサニル基とは例えばトリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。隣接置換基との間に形成される縮合環および脂肪族環とは、Ｒ1とＲ2、Ｒ2とＲ3、Ｒ1とＸ1、Ｒ3とＸ2の部位で共役または非共役の縮合環を形成するものである。そしてこれら縮合環は環内構造に窒素、酸素、硫黄原子を含んでいてもよいし、さらに別の環と縮合してもよい。
【００２０】
また、金属に配位する時には、ピロメテン化合物単独でも混合配位子でも特に限定はされない。混合配位子の場合の第２の配位子としては、アルコキシ、フェノキシ、ハロゲン、アルキル、アリルその他縮合環炭化水素、複素環化合物、または酸素原子を介して結合された芳香環または複素環化合物などを導入することが可能である。
【００２１】
本発明のリガンドに配位できる金属は、特に限定されるものではないが、通常用いられる元素の一例として、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金などを挙げることができる。
【００２２】
また、合成の容易さや化合物の熱的安定性を考えると、ピロメテン化合物としては下記一般式（２）の化合物であることが望ましい。
【００２３】
【化４】
ここで、Ｒ4〜Ｒ22はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される芳香族、脂肪族、あるいは複素環の縮合環の中から選ばれる。これらの置換基については上記一般式（１）の説明と同様である。
【００２５】
【化５】
【化７】
ここで、Ｒ23〜Ｒ41は一般式（２）のＲ4〜Ｒ22の選択肢と同じものから選ばれ、それぞれ同じでも異なっていてもよい。Ｒ42およびＲ43は同じでも異なっていてもよく、ハロゲン、水素、アルキル、アリール、複素環基から選ばれる。またあげられた置換基については、上記一般式（１）の説明と同様である。
【００２８】
さらに材料の入手しやすさや、合成の容易さを考えると上記一般式（３）のＲ42およびＲ43はフッ素であることが望ましい。上記のようなピロメテン化合物として具体的には以下のような化合物があげられる。
【００２９】
【化６】
【化７】
【化８】
【化９】
【化１０】
【化１１】
【化１２】
ドーピング量は、多すぎると濃度消光現象が起きるため、ホスト物質に対して１０重量％以下で用いることが好ましく、更に好ましくは２重量％以下である。ドーピング方法としては、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。また、ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーパント材料は積層されていても、分散されていても、いずれであってもよい。さらに、ピロメテン化合物は、極めて微量でも発光することから微量のピロメテン化合物をホスト材料にサンドイッチ状に挟んで使用することも可能である。この場合、一層でも二層以上ホスト材料と積層しても良い。 発光材料に添加するドーパント材料は、前記ピロメテン化合物一種のみに限る必要はなく、複数のピロメテン化合物を混合して用いたり、既知のドーパント材料の一種類以上をピロメテン化合物と混合して用いてもよい。具体的には従来から知られている、ビス（ジイソプロピルフェニル）ペリレンテトラカルボン酸イミドなどのナフタルイミド誘導体、ペリノン誘導体、アセチルアセトンやベンゾイルアセトンとフェナントロリンなどを配位子とするＥｕ錯体などの希土類錯体、４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピランやその類縁体、マグネシウムフタロシアニン、アルミニウムクロロフタロシアニンなどの金属フタロシアニン誘導体、ローダミン化合物、デアザフラビン誘導体、オキサジン化合物などを共存させることができるが特にこれらに限定されるものではない。
【００３７】
ホスト材料としては特に限定されるものではないが、以前から発光体として知られていたアントラセンやピレンなどの縮合環誘導体、トリス（８−キノリノラト）アルミニウムを始めとする金属キレート化オキシノイド化合物、ビススチリルアントラセン誘導体やジスチリルベンゼン誘導体などのビススチリル誘導体、テトラフェニルブタジエン誘導体、クマリン誘導体、オキサジアゾール誘導体、ピロロピリジン誘導体、ペリノン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、チアジアゾロピリジン誘導体、ピロロピロール誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、そして、ポリチオフェン誘導体などが使用できる。
【００３８】
本発明における電子輸送性材料としては、電界を与えられた電極間において陰極からの電子を効率良く輸送することが必要で、電子注入効率が高く、注入された電子を効率良く輸送することが望ましい。そのためには電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。このような条件を満たす物質として、８−ヒドロキシキノリンアルミニウムに代表されるキノリノール誘導体金属錯体、トロポロン金属錯体、フラボノール金属錯体、ペリレン誘導体、ペリノン誘導体、ナフタレン、クマリン誘導体、オキサジアゾール誘導体、アルダジン誘導体、ビススチリル誘導体、ピラジン誘導体、フェナントロリン誘導体などがあるが特に限定されるものではない。これらの電子輸送材料は単独でも用いられるが、異なる電子輸送材料と積層または混合して使用しても構わない。 正孔阻止層とは、電界を与えられた電極間において陽極からの正孔が陰極からの電子と再結合することなく移動するのを防止するための層であり、各層を構成する材料の種類によっては、この層を挿入することにより正孔と電子の再結合確率が増加し、発光効率の向上が望める場合がある。したがって、正孔阻止性材料としては正孔輸送性材料よりも最高占有分子軌道レベルがエネルギー的に低く、隣接する層を構成する材料とエキサイプレックスを生成しにくいことが望まれる。
具体的にはフェナントロリン誘導体やトリアゾール誘導体などが挙げられるが、素子作製に必要な薄膜を形成し、陽極からの正孔の移動を効率よく阻止できる化合物であれば特に限定されるものではない。
【００３９】
以上の正孔輸送層、発光層、電子輸送層、正孔阻止層は単独または二種類以上の材料を積層、混合するか、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ（Ｎ−ビニルカルバゾール）、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルフォン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリサルフォン、ポリアミド、エチルセルロース、酢酸ビニル、ＡＢＳ樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
【００４０】
発光を司る物質の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されるものではないが、通常は、抵抗加熱蒸着、電子ビーム蒸着が特性面で好ましい。層の厚みは、発光を司る物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。
【００４１】
電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力、寿命を考慮するとできるだけ低いエネルギーで最大の輝度が得られるようにするべきである。
【００４２】
本発明におけるマトリクスとは、表示のための画素が格子状に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状、サイズは用途によって決まる。例えばパソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられるし、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリックスのどちらでもよい。線順次駆動の方が構造が簡単であるという利点があるが、動作特性を考慮した場合、アクティブマトリックスの方が優れる場合があるので、これも用途によって使い分けることが必要である。
【００４３】
本発明におけるセグメントタイプとは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示、自動車のパネル表示などがあげられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。
【００４４】
【実施例】
以下、実施例および比較例をあげて本発明を説明するが、本発明はこれらの例によって限定されるものではない。以下に述べるピーク波長とは発光中心波長に値する主ピークの波長であり、半値幅とはピーク全体において発光中心波長の高さの半分のところのスペクトル幅である。
【００４５】
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、エッチングを行った。得られた基板をアセトン、”セミコクリン５６”で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０-5Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを５０ｎｍ蒸着した。次にホスト材料としてトリス（５，７−ジフェニル−８−キノリノラート）アルミニウム（III）、ドーパンド材料として下記に示すＤＰＴ１を用いて、ドーパント濃度が１ｗｔ％になるように１５ｎｍの厚さに共蒸着し、ホスト材料を３５ｎｍの厚さに積層した。次にリチウムを０．５ｎｍ、銀を１５０ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は水晶発振式膜厚モニター表示値である。この発光素子からの発光スペクトルは、ピーク波長が６４０ｎｍ、スペクトル半値幅が３０ｎｍであり、最高輝度は３８００ｃｄ／Ａの赤色発光が得られた。
【００４６】
【化１３】
実施例２
ドーパント材料に下記に示すＤＰＴ２を用いた以外は実施例１と全く同様にして作製した。この発光素子からの発光スペクトルは、ピーク波長が６４５ｎｍ、スペクトル半値幅が２８ｎｍであり、最高輝度は３５００ｃｄ／Ａの赤色発光が得られた。
【００４８】
【化１４】
比較例１
ドーパント材料に下記に示すＤＰＴ３を用いた以外は実施例１と全く同様にして作製した。この発光素子からの発光スペクトルは、ピーク波長が６２０ｎｍ、スペクトル半値幅が４５ｎｍであり、最高輝度は２７００ｃｄ／Ａの赤色発光が得られたのみであった。
【００５０】
【化１５】
【発明の効果】
以上のように、本発明により改良したピロメテン化合物を発光材料として用いることにより、高輝度・高色純度の赤色発光素子を得ることができた。[0001]
BACKGROUND OF THE INVENTION
The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.
[0002]
[Prior art]
In recent years, research on an organic laminated thin film light emitting device in which light is emitted when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes has been actively conducted. This element is attracting attention because it is thin, has high luminance emission under a low driving voltage, and multicolor emission by selecting a fluorescent material.
[0003]
This study was conducted by Kodak C.I. W. Since Tang et al. Have shown that organic laminated thin-film elements emit light with high brightness (Appl. Phys. Lett. 51 (12) 21, p. 913, 1987), many research institutions have studied. A typical structure of an organic laminated thin film light emitting device presented by a research group of Kodak Company is a hole transporting diamine compound on an ITO glass substrate, 8-hydroxyquinoline aluminum as a light emitting layer, and Mg: Ag as a cathode. They were sequentially provided, and a green light emission of 1000 cd / m 2 was possible with a driving voltage of about 10V. Some organic multilayer thin film light emitting elements have different configurations such as those provided with an electron transport layer in addition to the above-described element constituent elements, but basically follow the configuration of Kodak Company.
[0004]
Among multicolor light emission, red light emission has been studied as a useful light emission color. Conventionally, perylene series such as bis (diisopropylphenyl) perylene, perinone series, porphyrin series, Eu complex (Chem. Lett., 1267 (1991)) and the like are known as red light emitting materials.
[0005]
As a method for obtaining red light emission, a method of mixing a small amount of a red fluorescent material as a dopant in a host material has been studied. Examples of the host material include tris (8-quinolinolato) aluminum complex, bis (10-benzoquinolinolato) beryllium complex, diarylbutadiene derivative, stilbene derivative, benzoxazole derivative, benzothiazole derivative, and the like. Red light emission is extracted by the presence of 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran, metal phthalocyanine (MgPc, AlPcCl, etc.) compounds, squarylium compounds, and violanthrone compounds. It was.
[0006]
Further, as a light-emitting material, particularly a dopant material, a pyromethene compound which is a compound exhibiting high-luminance light emission is known (Japanese Patent Laid-Open No. 9-118880). It is also known that red light is emitted by introducing an aromatic ring or the like into the pyromethene skeleton (Japanese Patent Laid-Open No. 2000-208265).
[0007]
[Problems to be solved by the invention]
Many of the light emitting materials (host materials and dopant materials) used in the prior art have low light emission efficiency and high power consumption, and low compound durability and short device lifetime. In addition, among the three primary colors required for full-color displays, high-performance light-emitting materials have been found for green light emission. However, blue and red, especially red, have sufficient characteristics, especially high brightness and high color purity. A luminescent material has not been obtained. The object of the present invention is to solve the problems of the prior art and to provide a red light emitting device having high luminous efficiency and excellent color purity.
[0008]
[Means for Solving the Problems]
That is, the present invention relates to an element in which a luminescent substance is present between an anode and a cathode and emits light by electric energy, and the element has a pyromethene compound represented by the general formula ( 3 ) or a metal complex thereof as a dopant in a light emitting layer. A light-emitting element including the material .
[0009]
[Chemical 2]
(Here, R 23 to R 40 may be the same or different and are selected from hydrogen and an alkyl group. R 41 is an aryl group. R 42 and R 43 are fluorine .)
[0011]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, if the anode is transparent for extracting light, a conductive metal oxide such as tin oxide, indium oxide and indium tin oxide (ITO), or a metal such as gold, silver and chromium, copper iodide, sulfide Inorganic conductive materials such as copper and conductive polymers such as polythiophene, polypyrrole, and polyaniline are not particularly limited, but it is particularly desirable to use ITO glass or Nesa glass. The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10 Ω / □, it is particularly desirable to use a low resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm. Further, soda lime glass, non-alkali glass or the like is used for the glass substrate, and the thickness of the glass substrate only needs to be sufficient to maintain the mechanical strength, so 0.5 mm or more is sufficient. As for the glass material, alkali-free glass is preferred because it is better that ions eluted from the glass are less, but soda-lime glass with a barrier coat such as SiO 2 is also commercially available and can be used. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, or a chemical reaction method.
[0012]
The cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but is generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium. Magnesium and the like can be mentioned, but lithium, sodium, potassium, calcium, magnesium or alloys containing these low work function metals are effective for improving the device characteristics by increasing the electron injection efficiency. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness gauge display) to be stable. Although a method using a high electrode can be mentioned as a preferred example, it is not particularly limited to these because an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum, indium, or alloys using these metals, and inorganic substances such as silica, titania, silicon nitride, polyvinyl alcohol, vinyl chloride, Preferred examples include laminating hydrocarbon polymers. The method for producing these electrodes is not particularly limited as long as conduction can be achieved such as resistance heating, electron beam, sputtering, ion plating, and coating.
[0013]
The light-emitting substance is 1) hole transport layer / light-emitting layer, 2) hole transport layer / light-emitting layer / electron transport layer, 3) light-emitting layer / electron transport layer, 4) hole transport layer / light-emitting layer / hole Blocking layer, 5) Hole transport layer / light emitting layer / hole blocking layer / electron transport layer, 6) Light emitting layer / hole blocking layer / electron transport layer, and 7) Form in which one or more of the above combination materials are mixed Any of these may be used. That is, as the element structure, in addition to the multilayer laminated structure of 1) to 6) above, only a single layer including a light emitting material alone or a layer containing a light emitting material and a hole transport material or an electron transport material may be provided. Furthermore, the luminescent substance in the present invention corresponds to both a substance that emits light by itself and a substance that assists the light emission, and refers to a compound, a layer, or the like that is involved in light emission.
[0014]
The hole transport layer is formed by laminating and mixing a hole transport material alone or two or more kinds of materials, or a mixture of a hole transport material and a polymer binder. '-Diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-diphenyl-4,4'- Triphenylamines such as diphenyl-1,1′-diamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) s, pyrazoline derivatives, stilbene compounds, hydrazone compounds, oxadiazole derivatives and phthalocyanine derivatives , Heterocyclic compounds typified by porphyrin derivatives, in polymer systems, polycarbonates or styrene derivatives, polyvinylcarbazole, Although the run and the like are preferable, and forming a thin film required for device fabrication, and can inject holes from the anode, and is not particularly limited as long as it is a further compound capable of transporting holes.
[0015]
The light emitting material may be either a host material alone or a combination of a host material and a dopant material. Further, the dopant material may be included in the entire host material, or may be included partially. The dopant material may be either laminated or dispersed.
[0016]
Conventionally, it is known that a pyromethene compound exhibits high-luminance light emission as a light-emitting material, particularly a dopant material, and it is also known that red light emission is exhibited by introducing an aromatic ring or the like into a pyromethene skeleton. However, red light emission satisfying both emission luminance and chromaticity has not been obtained. Therefore, in the pyromethene compound of the present invention, the aromatic ring (Ar 1 and Ar 2 in the general formula (1)) introduced into the pyromethene skeleton in order to obtain red light emission is linked and fixed to the pyromethene skeleton by a chemical bond. As a result, the fluorescence quantum yield of the pyromethene compound is improved, the half-value width of the emission spectrum is narrowed, and red emission with high luminance and high color purity can be obtained. Examples of the pyromethene compound include a compound of the following general formula (1) or a metal complex thereof.
[0017]
[Chemical 3]
Here, R 1 to R 3 may be the same as or different from each other, and are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group. , Aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group , A siloxanyl group, and an aromatic, aliphatic, or heterocyclic condensed ring formed between adjacent substituents. X 1 and X 2 may be the same or different from each other, and are a single bond, substituted or unsubstituted alkylene bond, ether bond, sulfide bond, substituted or unsubstituted amino bond, substituted or unsubstituted amide bond, or ester bond. , Selected from carbonyl bonds. Ar 1 and Ar 2 represent a substituted or unsubstituted aryl group.
[0019]
Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. The aralkyl group is an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. It doesn't matter. The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. . The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom. The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group, which may be unsubstituted or substituted. The heterocyclic group is a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, or a carbazolyl group, which may be unsubstituted or substituted. Absent. Halogen is fluorine, chlorine, bromine or iodine. Haloalkane, haloalkene, haloalkyne means, for example, a part or all of the above-mentioned alkyl group, alkenyl group, alkynyl group such as trifluoromethyl group substituted with the above-mentioned halogen, and the remaining part may be unsubstituted It may be replaced. Aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, etc. The cyclic hydrocarbon, aromatic hydrocarbon and heterocyclic ring may be unsubstituted or substituted. A silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. The condensed ring and aliphatic ring formed between adjacent substituents are conjugated or non-conjugated at the sites of R 1 and R 2 , R 2 and R 3 , R 1 and X 1 , R 3 and X 2 . It forms a condensed ring. These condensed rings may contain a nitrogen, oxygen or sulfur atom in the ring structure, or may be condensed with another ring.
[0020]
Further, when coordinated to a metal, there is no particular limitation on the pyromethene compound alone or a mixed ligand. As the second ligand in the case of a mixed ligand, alkoxy, phenoxy, halogen, alkyl, allyl and other condensed ring hydrocarbons, heterocyclic compounds, or aromatic rings or heterocyclic compounds bonded through an oxygen atom Etc. can be introduced.
[0021]
The metal that can be coordinated to the ligand of the present invention is not particularly limited. Examples of commonly used elements include boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum. be able to.
[0022]
Further, considering the ease of synthesis and the thermal stability of the compound, the pyromethene compound is preferably a compound of the following general formula (2).
[0023]
[Formula 4]
Here, R 4 to R 22 may be the same as or different from each other, and are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group. , Aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group , A siloxanyl group, and an aromatic, aliphatic, or heterocyclic condensed ring formed between adjacent substituents. These substituents are the same as described in the general formula (1).
[0025]
[Chemical formula 5]
[Chemical 7]
Here, R 23 to R 41 are selected from the same options as R 4 to R 22 in the general formula (2), and may be the same or different. R 42 and R 43 may be the same or different and are selected from halogen, hydrogen, alkyl, aryl, and a heterocyclic group. The above-mentioned substituents are the same as described in the general formula (1).
[0028]
Further, considering the availability of materials and the ease of synthesis, R 42 and R 43 in the general formula (3) are preferably fluorine. Specific examples of the above-mentioned pyromethene compound include the following compounds.
[0029]
[Chemical 6]
[Chemical 7]
[Chemical 8]
[Chemical 9]
[Chemical Formula 10]
Embedded image
Embedded image
If the doping amount is too large, a concentration quenching phenomenon occurs, so that it is preferably used in an amount of 10% by weight or less, more preferably 2% by weight or less based on the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. Further, the dopant material may be included in the entire host material, or may be included partially. The dopant material may be either laminated or dispersed. Furthermore, since the pyromethene compound emits light even in a very small amount, it is also possible to use a very small amount of the pyromethene compound sandwiched between the host materials. In this case, one or more layers may be laminated with the host material. The dopant material added to the light emitting material need not be limited to only one pyromethene compound, and a plurality of pyromethene compounds may be mixed and used, or one or more kinds of known dopant materials may be mixed with a pyromethene compound. . Specifically, conventionally known rare earth complexes such as naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, oxazine compounds, etc. However, the present invention is not particularly limited thereto.
[0037]
Although it does not specifically limit as a host material, Metal chelating oxinoid compounds, such as fused ring derivatives, such as anthracene and pyrene, tris (8- quinolinolato) aluminum which were known as a light emitter for a long time, bisstyryl Bisstyryl derivatives such as anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, pyrrolopyrrole derivatives In the polymer system, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polythiophene derivatives, and the like can be used.
[0038]
As the electron transporting material in the present invention, it is necessary to efficiently transport electrons from the cathode between electrodes to which an electric field is applied, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. . For this purpose, it is required that the material has a high electron affinity, a high electron mobility, excellent stability, and a substance that does not easily generate trapping impurities during manufacturing and use. As substances satisfying such conditions, quinolinol derivative metal complexes represented by 8-hydroxyquinoline aluminum, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene, coumarin derivatives, oxadiazole derivatives, aldazine derivatives, Although there are bisstyryl derivatives, pyrazine derivatives, phenanthroline derivatives, etc., there is no particular limitation. These electron transport materials are used alone, but may be laminated or mixed with different electron transport materials. The hole blocking layer is a layer for preventing the holes from the anode from moving between the electrodes to which an electric field is applied without recombining with the electrons from the cathode, and the kind of material constituting each layer. Depending on the case, insertion of this layer may increase the probability of recombination of holes and electrons, and may improve the light emission efficiency. Therefore, it is desirable that the hole-occluding material has a lower maximum occupied molecular orbital level than the hole-transporting material in terms of energy, and it is difficult to generate an exciplex with the material constituting the adjacent layer.
Specific examples include a phenanthroline derivative and a triazole derivative. However, the compound is not particularly limited as long as it is a compound that forms a thin film necessary for device fabrication and can efficiently block the movement of holes from the anode.
[0039]
The above hole transport layer, light-emitting layer, electron transport layer, and hole blocking layer may be a single material or a laminate of two or more materials, mixed, or polymer binders such as polyvinyl chloride, polycarbonate, polystyrene, poly (N -Vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane resin, etc. It can also be used by being dispersed in a soluble resin, a curable resin such as a phenol resin, a xylene resin, a petroleum resin, a urea resin, a melamine resin, an unsaturated polyester resin, an alkyd resin, an epoxy resin, or a silicone resin.
[0040]
The formation method of the substance responsible for light emission is not particularly limited, such as resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, coating method, etc., but resistance heating evaporation and electron beam evaporation are usually preferable in terms of characteristics. . The thickness of the layer is not limited because it depends on the resistance value of the substance responsible for light emission, but is selected from 1 to 1000 nm.
[0041]
Electrical energy mainly refers to direct current, but pulsed current or alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance should be obtained with the lowest possible energy in consideration of the power consumption and lifetime of the element.
[0042]
The matrix in the present invention refers to a matrix in which pixels for display are arranged in a lattice pattern, and displays characters and images by a set of pixels. The shape and size of the pixel are determined by the application. For example, a rectangular pixel with a side of 300 μm or less is normally used for displaying images and characters on a personal computer, monitor, television, etc. In a large display such as a display panel, a pixel with a side of mm order is used. . In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
[0043]
The segment type in the present invention means that a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation status display of an audio device or an electromagnetic cooker, the panel display of an automobile, etc. The matrix display and the segment display may coexist in the same panel.
[0044]
【Example】
EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples. The peak wavelength described below is the wavelength of the main peak deserving the emission center wavelength, and the half width is the spectrum width at half the height of the emission center wavelength in the entire peak.
[0045]
Example 1
A glass substrate on which an ITO transparent conductive film was deposited to a thickness of 150 nm (Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) was cut into 30 × 40 mm and etched. The obtained substrate was ultrasonically washed with acetone and “Semicocrine 56” for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −5 Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 50 nm. Next, tris (5,7-diphenyl-8-quinolinolato) aluminum (III) as a host material and DPT1 shown below as a dopant material were co-evaporated to a thickness of 15 nm so that the dopant concentration was 1 wt%. The host material was laminated to a thickness of 35 nm. Next, lithium was deposited to 0.5 nm and silver was deposited to 150 nm to prepare a cathode having a 5 × 5 mm square. The film thickness mentioned here is a display value of a crystal oscillation type film thickness monitor. The light emission spectrum from this light emitting element was a red light emission having a peak wavelength of 640 nm, a spectrum half width of 30 nm, and a maximum luminance of 3800 cd / A.
[0046]
Embedded image
Example 2
It was produced in the same manner as in Example 1 except that DPT2 shown below was used as the dopant material. The light emission spectrum from this light emitting element was a red light emission having a peak wavelength of 645 nm, a spectrum half width of 28 nm, and a maximum luminance of 3500 cd / A.
[0048]
Embedded image
Comparative Example 1
It was produced in the same manner as in Example 1 except that DPT3 shown below was used as the dopant material. The emission spectrum from this light-emitting element had a peak wavelength of 620 nm, a spectral half width of 45 nm, and a maximum luminance of 2700 cd / A red light emission only.
[0050]
Embedded image
【The invention's effect】
As described above, by using the pyromethene compound improved according to the present invention as a light emitting material, a red light emitting device having high luminance and high color purity could be obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000320569A JP4524901B2 (en) | 2000-10-20 | 2000-10-20 | Light emitting element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000320569A JP4524901B2 (en) | 2000-10-20 | 2000-10-20 | Light emitting element |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002134275A JP2002134275A (en) | 2002-05-10 |
| JP2002134275A5 JP2002134275A5 (en) | 2007-11-22 |
| JP4524901B2 true JP4524901B2 (en) | 2010-08-18 |
Family
ID=18798834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000320569A Expired - Fee Related JP4524901B2 (en) | 2000-10-20 | 2000-10-20 | Light emitting element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4524901B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2022794B1 (en) * | 2006-04-28 | 2017-08-23 | Keio University | Fluorescent compound and labeling agent comprising the same |
| KR20120005793A (en) * | 2010-07-09 | 2012-01-17 | 삼성모바일디스플레이주식회사 | Display device |
| US20210336145A1 (en) * | 2018-08-27 | 2021-10-28 | Toray Industries, Inc. | Pyrromethene boron complex, light emitting element using same, display device, lighting device, color conversion composition, color conversion film, color conversion substrate, light source unit and display |
| WO2020184369A1 (en) | 2019-03-11 | 2020-09-17 | 東レ株式会社 | Pyrromethene metal complex, pyrromethene compound, light-emitting element material, light-emitting element, display device, and illumination device |
| WO2024075649A1 (en) * | 2022-10-07 | 2024-04-11 | 東レ株式会社 | Pyrromethene boron complex, color conversion composition, color conversion sheet, color conversion substrate, light source unit, display device, and lighting device |
-
2000
- 2000-10-20 JP JP2000320569A patent/JP4524901B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002134275A (en) | 2002-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4876333B2 (en) | Light emitting element | |
| JP4876311B2 (en) | Light emitting element | |
| KR101540637B1 (en) | Light-emitting device | |
| JP2002015871A (en) | Luminescent element | |
| JP2002063988A (en) | Light emitting element | |
| JP2000208265A (en) | Light emitting element | |
| JP2006073581A (en) | Light emitting device and material therefor | |
| JP4052010B2 (en) | Light emitting device material and light emitting device using the same | |
| JP2007208165A (en) | Light emitting element | |
| JP4000893B2 (en) | Pyromethene metal complex, light emitting device material and light emitting device using the same | |
| JP2003151773A (en) | Light emitting element | |
| JP4085574B2 (en) | Light emitting element | |
| JP4729776B2 (en) | Light emitting element | |
| JP2001307884A (en) | Electoluminiscent element | |
| JP2001291590A (en) | Light emitting element | |
| JP2006245172A (en) | Light emitting element | |
| JP2001250689A (en) | Light emission element | |
| JP4613411B2 (en) | Light emitting element | |
| JP4710268B2 (en) | Pyromethene compound, light emitting device material and light emitting device using the same | |
| JP2005154534A (en) | Light emitting device material and light emitting device using the same | |
| JP4524901B2 (en) | Light emitting element | |
| JP2002008866A (en) | Light element | |
| JP2006310538A (en) | Light-emitting element | |
| JP4061969B2 (en) | Light emitting element | |
| JP2001223082A (en) | Light emitting element |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071003 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071003 |
|
| 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: 20100511 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100524 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130611 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130611 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130611 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140611 Year of fee payment: 4 |
|
| LAPS | Cancellation because of no payment of annual fees |