JP4432313B2 - Tetraphenylmethane derivative and light emitting device including the same - Google Patents
Tetraphenylmethane derivative and light emitting device including the same Download PDFInfo
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- JP4432313B2 JP4432313B2 JP2002297030A JP2002297030A JP4432313B2 JP 4432313 B2 JP4432313 B2 JP 4432313B2 JP 2002297030 A JP2002297030 A JP 2002297030A JP 2002297030 A JP2002297030 A JP 2002297030A JP 4432313 B2 JP4432313 B2 JP 4432313B2
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- derivatives
- light emitting
- electron transport
- tetraphenylmethane
- Prior art date
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- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical class C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 title claims description 27
- 239000000463 material Substances 0.000 claims description 74
- -1 benzoquinolinyl group Chemical group 0.000 claims description 29
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000005412 pyrazyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 description 29
- 230000032258 transport Effects 0.000 description 28
- 239000010410 layer Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- 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 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000005595 acetylacetonate group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000005013 aryl ether group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229950005228 bromoform Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 125000002346 iodo group Chemical group I* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 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
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000004322 quinolinols Chemical class 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 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 2
- 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 2
- 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 2
- FVLANAMJWVQMQQ-UHFFFAOYSA-N 1-(2'-acetyl-9,9'-spirobi[fluorene]-2-yl)ethanone Chemical compound C12=CC=CC=C2C2=CC=C(C(C)=O)C=C2C21C1=CC=CC=C1C1=CC=C(C(=O)C)C=C12 FVLANAMJWVQMQQ-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- KIIGPNDJMVHUSL-UHFFFAOYSA-N 1-phenyl-2-benzofuran Chemical compound C=12C=CC=CC2=COC=1C1=CC=CC=C1 KIIGPNDJMVHUSL-UHFFFAOYSA-N 0.000 description 2
- ZAMLCNSCTZZXCU-UHFFFAOYSA-N 8-aminoquinoline-7-carbaldehyde Chemical compound C1=CN=C2C(N)=C(C=O)C=CC2=C1 ZAMLCNSCTZZXCU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000004832 aryl thioethers Chemical group 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 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
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 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 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 2
- 150000005255 pyrrolopyridines Chemical class 0.000 description 2
- 150000003377 silicon compounds Chemical group 0.000 description 2
- 150000003967 siloles Chemical class 0.000 description 2
- 125000005401 siloxanyl group Chemical group 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 150000007979 thiazole derivatives Chemical class 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
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 1
- 229920003227 poly(N-vinyl carbazole) Polymers 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
- 229920000548 poly(silane) polymer 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
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 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
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 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
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 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
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 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
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical class C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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および発光素子用材料に関する。
【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(非特許文献1参照。)、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】
フルカラーディスプレイの実現を目指して、発光材料は三原色(RGB)揃うことが求められ、これまでは緑色発光材料の研究が最も進んでおり、次いで青色発光材料が、そして最近では赤色発光材料において最も特性向上が望まれ、鋭意研究がなされている。発光材料には蛍光材料だけでなく、燐光材料なども検討されている。また、電荷輸送材料として、これまでは正孔輸送材料の研究が盛んであったが、最近では電子輸送材料も熱心に検討されている(例えば、特許文献1及び特許文献2参照。)。
【0005】
【非特許文献1】
Appl.Phys.Lett.51(12)21,p.913,1987(914頁)
【0006】
【特許文献1】
特開2000−119644号公報(17頁)
【0007】
【特許文献2】
国際公開第00/03565号パンフレット(特許請求の範囲)
【0008】
【発明が解決しようとする課題】
しかし、従来技術に用いられる発光材料、正孔輸送材料、電子輸送材料は耐久性に劣るものが多かった。長時間の通電による素子からの発熱により結晶化し、素子寿命が短くなってしまうものである。また、上記結晶化を抑制するためにアモルファス性を付与した材料は、昇華性が低いため真空蒸着時に分解や重合などの変性が起こってしまうものが多かった。
【0009】
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、高輝度で色純度が良く、しかも耐久性に優れた発光素子を提供することを目的とするものである。
【0010】
すなわち本発明は、一般式(1)で表されるテトラフェニルメタン誘導体を有する電子輸送材料であり、該電子輸送材料を陽極と陰極の間に存在する電子輸送層として用いた発光素子である。
【0011】
【化2】
【0012】
(ここでR1〜R20は水素である。但し、R1〜R5のうち少なくとも1つ及びR6〜R10のうち少なくとも1つはピリジル基、ビピリジル基、ターピリジル基、クウォーターピリジル基、キノリニル基、ベンゾキノリニル基、フェナントロリン基、アクリジニル基、ナフチリジニル基、ピラジル基、キノキサリニル基、ベンゾキノキサリニル基またはフェナジニル基から選ばれる。)
【0013】
【発明の実施の形態】
本発明において新規な化合物は、下記一般式(1)で表されるテトラフェニルメタン誘導体である。
【0014】
【化3】
【0015】
(ここでR1〜R20は水素、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環構造の中から選ばれる。但し、R1〜R5のうち少なくとも1つ及びR6〜R10のうち少なくとも1つはピリジン環骨格を有する置換基である)。
【0016】
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リル基、チエニル基、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。また、隣接置換基との間に環構造を形成しても構わない。形成される環構造は無置換でも置換されていてもかまわない。
【0017】
ピリジン環骨格を有する置換基とは、ピリジル基を1つ乃至複数含有する置換基や、ピリジン環を含む多環芳香族基を示し、例えば、ピリジル基、ビピリジル基、ターピリジル基、クウォーターピリジル基、キノリニル基、ベンゾキノリニル基、フェナントロリン基、アクリジニル基、ナフチリジニル基などが挙げられ、これらは水素以外の置換基を有していてもよい。
【0018】
また、ピリジン環骨格のかわりに、ピリジン環の4位の炭素原子が窒素原子に置き換わったピラジン環骨格を使用することもできる。このような置換基として、例えば、ピラジル基、キノキサリニル基、ベンゾキノキサリニル基、フェナジニル基などが挙げられ、これらは水素以外の置換基を有していてもよい。
【0019】
上記ピリジン環骨格またはピラジン環骨格を有する置換基は耐熱性の点から、多環芳香族基であることが好ましい。
【0020】
電荷輸送性や薄膜形成性などの機能性を効果的に発現させるために、R1〜R20の少なくとも一つに、機能性置換基を導入することもできる。その例としては、トリフェニルアミン、ジフェニルアミン、カルバゾール、インドール、ジフェニルビニル、フルオレニル、フェナンスリル、アントラニル、ピレニル、ペリレニル、ビフェニル、ターフェニル、クオーターフェニルなどの電荷輸送性置換基や、アルキル基、アルコキシ基、アリールエーテル基などの薄膜形成性置換基が挙げられるが特に限定されるものではない。
【0021】
ピリジン環骨格を有する置換基の数は特に限定されるものではないが、2つ以上4つ以下が好ましく、2つがより好ましい。1つの場合は電荷輸送性が低く機能発現が不十分なことがあり、5つ以上の場合は合成や精製が困難であったり、昇華性が低いために真空蒸着時に分解や重合等の変性が起こってしまうことがある。
【0022】
ピリジン環骨格を有する置換基の位置は特に限定されるものではないが、合成の容易さの観点からR2、R3、R4、R7、R8、R9、R12、R13、R14、R17、R18、R19が好ましく、耐熱性の観点からR3、R8、R13、R18がより好ましい。
【0023】
ピリジン環骨格を有する置換基はテトラフェニルメタン骨格に直接結合していても、テトラフェニルメタン骨格との間に2価の連結基を介していてもよい。この場合の2価の連結基とは特に限定されるものではないが、アルキル基、エーテル基、チオエーテル基、ケトン基、置換あるいは無置換のアミノ基、アミド基、アリール基、複素環基などが挙げられる。合成の容易さや耐熱性の観点から、機能性置換基は直接、または2価の連結基としてアリール基、複素環基を介して結合していることが好ましい。
【0024】
一般式(1)で表される化合物は以下の方法で合成することができるが特に限定されるものではない。
【0025】
テトラフェニルメタン骨格の合成については、参考文献としてAngew.Chem.Int.Ed.Engl.vol.25(1986)No.12の第1098頁や、Tetrahedron Letters,vol.38(1997)の第1487頁などがあげられる。具体的には、無溶媒または酢酸溶媒中、トリフェニルメタノールまたはトリフェニルメチルクロライドを、アニリンまたはアニリン塩酸塩と100℃乃至220℃で反応させ、得られた中間体を常法で処理して単離し、次いでエタノール/硫酸の混合溶媒中、−10℃でイソアミルナイトライトと反応させ、ホスフィン酸を加えて加熱還流し、常法で処理し得ることができる。
【0026】
テトラフェニルメタン骨格へのピリジン環骨格を有する置換基や前述の機能性置換基の導入については、直接でも良いが、まず反応性置換基を導入し、その後該置換基を導入する方法が好ましい。反応性置換基としては、アセチル基、ヨード基、ブロモ基などがあげられるが特に限定されるものではない。
【0027】
アセチル基の導入法としては、一般的かつ簡便なフリーデル・クラフツのアシル化があげられる。参考文献としては、特開平7−278537号公報の第27頁「実施例A.出発化合物(f)2,2’−ジアセチル−9,9’−スピロビフルオレン」やHelvetica Chimica Acta,vol.52(1969)第1210頁「Experimenteller Tell 2,2’−diacetyl−9,9’−spirobifluorene(IV)」などがあげられる。具体的には、テトラフェニルメタンを1,2−ジクロロエタン中で50℃で塩化アセチルと塩化アルミニウムと反応させ、常法で処理し、アセチル基を導入することができる。塩化アセチルと塩化アルミニウムの当量を変えて、1〜4置換体を得ることができる。
【0028】
ヨード基の導入については、参考文献として、前述のTetrahedronLetters,vol.38(1997)の第1487頁などがあげられる。具体的には、テトラフェニルメタンを四塩化炭素中で50℃乃至60℃でヨウ素とビス(トリフルオロアセトキシ)ヨードベンゼンと反応させ、常法で処理し、ヨード基を導入することができる。
【0029】
ブロモ基の導入については、参考文献として、前述のAngew.Chem.Int.Ed.Engl.25(1986)No.12の第1098頁などがあげられる。具体的には、テトラフェニルメタンを室温で臭素と反応させ、常法で処理し、ブロモ基を導入することができる。臭素の当量を変えて、1〜4置換体を得ることができる。
【0030】
反応性置換基を導入した後のテトラフェニルメタン骨格へのピリジン環骨格を有する置換基や機能性置換基の導入については、アセチル基からフェナントロリン基、ベンゾキノリニル基、ナフチリジニル基、ターピリジル基、インドール基の導入、ヨード基、ブロモ基からフェナントロリン基、ビピリジル基、ターピリジル基、ジフェニルアミノ基、カルバゾール基、ジフェニルエチレン基、ポリフェニレン基、n−ブチル基の導入などがあげられるが特に限定されるものではない。
【0031】
フェナントロリン基の導入については、参考文献として、Tetrahedron Letters,vol.40(1999).第7312頁スキームやJ.Org.Chem.1996,61.第3020頁「2−Phenyl−1,10−phenanntoroline」、Tetrahedron Letters,vol.23(1982).第5291頁〜第5294頁などがあげられる。具体的には、テトラフェニルメタンのアセチル体をジオキサン中で60℃で8−アミノ−7−キノリンカルボアルデヒド、水酸化カリウムと反応させ、常法で処理する方法や、テトラフェニルメタンのヨード体またはブロモ体を金属リチウムでリチオ化し、次いで無水フェナントロリンと反応させて、水、二酸化マンガンで処理する方法などで、フェナントロリン基を導入することができる。
【0032】
インドール基の導入については、参考文献として、Tetrahedron Letters,vol.40(1999).第7312頁スキームなどがあげられる。具体的には、テトラフェニルメタンのアセチル体と1−メチル−1−フェニルヒドラジンをエタノール中で加熱環流させ、酢酸を加えてさらに加熱環流させ、常法で処理し、ヒドラジン体を得て、これをポリりん酸中で160℃で加熱し、常法で処理し、インドール基を導入することができる。
【0033】
ジフェニルエチレン基の導入については、参考文献として、SPIE,vol.3797.第317頁「2.1Synthesis EM1」などがあげられる。具体的には、テトラフェニルメタンのブロモ体にジフェニルビニルボロン酸、炭酸ナトリウム、テトラキス(トリフェニルホスフィン)パラジウム触媒を加え、水−トルエン中で100℃で反応させ、常法で処理し、ジフェニルビニル基を導入することができる。同様にポリフェニレンを導入することができる。
【0034】
ジフェニルアミノ基の導入については、参考文献として、SPIE,vol.3797.第317頁「2.1Synthesis HTM1」などがあげられる。具体的には、テトラフェニルメタンのブロモ体に、ジフェニルアミン、t−ブトキシナトリウム、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル、酢酸パラジウムを加え、トルエン中で加熱環流させ、常法で処理し、ジフェニルアミノ基を導入することができる。同様にカルバゾリル基を導入することができる。
【0035】
n−ブチル基の導入については、具体的には、テトラフェニルメタンのブロモ体にTHF中室温でn−ブチルリチウムと反応させ、常法で処理し、n−ブチル基を導入することができる。テトラフェニルメタンのブロモ体からの上述の機能性置換基導入の際に残留する未反応ブロモ基を処理することができ、薄膜形成性にも有利である。
【0036】
上記のテトラフェニルメタン誘導体として、具体的には下記のような構造があげられるが特に限定されるものではない。
【0037】
【化4】
【0038】
【化5】
【0039】
また、本発明は上記一般式(1)で表される電子輸送材料を、陽極と陰極の間に存在する電子輸送層として用いた発光素子である。
【0040】
一般式(1)で表されるテトラフェニルメタン誘導体は立体的な骨格であるため、耐熱性が高く、結晶化を防ぎ、薄膜形成性に優れた化合物である。さらに化学的、電気化学的に安定であり、真空蒸着時に分解や重合などの変性が起こることがなく、極めて耐久性に優れるという特徴を有する。
【0041】
本発明の発光素子において陽極は、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ー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。
【0042】
本発明の発光素子において陰極は、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セシウム、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。
【0043】
本発明の発光素子において発光物質とは、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、そして、4)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)〜3)の多層積層構造の他に4)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、本発明の発光素子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。
【0044】
本発明の発光素子において正孔輸送性材料は、電界を与えられた電極間において陽極からの正孔を効率良く輸送することが必要で、正孔注入効率が高く、注入された正孔を効率良く輸送することが望ましい。そのためにはイオン化ポテンシャルが小さく、しかも正孔移動度が大きく、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。
【0045】
このような条件を満たす物質として、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’−ジアミンや、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)や、ビス(N−アルキルカルバゾール)類などのカルバゾール類、インドール誘導体、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、ポリシランなどがあげられるが特に限定されるものではない。
【0046】
本発明における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。
【0047】
本発明の発光素子において発光材料は、正孔輸送層あるいは直接陽極から受けとった正孔と、電子輸送層あるいは直接陰極から受け取った電子を効率よく再結合させることが必要で、ドーパント材料を含む場合は、再結合のエネルギーをドーパント材料に効率よく移動させることが必要である。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。
【0048】
このような条件を満たす物質として、本発明におけるテトラフェニルメタン誘導体や、以前から発光体として知られていたアントラセン、フェナンスレン、ピレン、ペリレン、クリセ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キノリノール誘導体の金属錯体、ベンズオキサゾール誘導体、スチルベン誘導体、ベンズチアゾール誘導体、チアジアゾール誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、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、キノリノール誘導体と異なる配位子を組み合わせた金属錯体、オキサジアゾール誘導体金属錯体、ベンズアゾール誘導体金属錯体、クマリン誘導体、ピロロピリジン誘導体、ピロロピロール誘導体、シロール誘導体、ペリノン誘導体、チアジアゾロピリジン誘導体、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あげられるが特に限定されるものではない。
【0049】
発光材料に添加するドーパント材料は、ホスト材料からの再結合エネルギーを効率よく受け取ることが必要で、量子収率が高く、しかも濃度消光を起こしにくいことが望ましい。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。
【0050】
このような条件を満たす物質として、本発明におけるテトラフェニルメタン誘導体や、従来から知られている、フェナンスレン、アントラセン、ピレン、テトラセン、ペンタセン、ペリレン、ナフトピレン、ジベンゾピレン、ルブレンなどの縮合環誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、ベンズイミダゾール誘導体、ベンズトリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、チアゾール誘導体、イミダゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラゾリン誘導体、スチルベン誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、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、ジアザインダセン誘導体、フラン誘導体、ベンゾフラン誘導体、フェニルイソベンゾフラン、ジメシチルイソベンゾフラン、ジ(2−メチルフェニル)イソベンゾフラン、ジ(2−トリフルオロメチルフェニル)イソベンゾフラン、フェニルイソベンゾフランなどのイソベンゾフラン誘導体、ジベンゾフラン誘導体、7−ジアルキルアミノクマリン誘導体、7−ピペリジノクマリン誘導体、7−ヒドロキシクマリン誘導体、7−メトキシクマリン誘導体、7−アセトキシクマリン誘導体、3−ベンズチアゾリルクマリン誘導体、3−ベンズイミダゾリルクマリン誘導体、3−ベンズオキサゾリルクマリン誘導体などのクマリン誘導体、ジシアノメチレンピラン誘導体、ジシアノメチレンチオピラン誘導体、ポリメチン誘導体、シアニン誘導体、オキソベンズアンスラセン誘導体、キサンテン誘導体、ローダミン誘導体、フルオレセイン誘導体、ピリリウム誘導体、カルボスチリル誘導体、アクリジン誘導体、オキサジン誘導体、フェニレンオキサイド誘導体、キナクリドン誘導体、キナゾリン誘導体、ピロロピリジン誘導体、フロピリジン誘導体、1,2,5−チアジアゾロピレン誘導体、ピロメテン誘導体、ペリノン誘導体、ピロロピロール誘導体、スクアリリウム誘導体、ビオラントロン誘導体、フェナジン誘導体、アクリドン誘導体、ジアザフラビン誘導体などがあげられるが、特に限定されるものではない。
【0051】
また、ドーパント材料として上記蛍光性(一重項発光)材料だけでなく、燐光性(三重項発光)材料も好ましく用いられる。具体的には、ポルフィリン白金錯体やトリス(2−フェニルピリジル)イリジウム錯体、トリス{2−(2−チオフェニル)ピリジル}イリジウム錯体、トリス{2−(2−ベンゾチオフェニル)ピリジル}イリジウム錯体、トリス(2−フェニルベンゾチアゾール)イリジウム錯体、トリス(2−フェニルベンゾオキサゾール)イリジウム錯体、トリスベンゾキノリンイリジウム錯体、ビス(2−フェニルピリジル)(アセチルアセトナート)イリジウム錯体、ビス{2−(2−チオフェニル)ピリジル}イリジウム錯体、ビス{2−(2−ベンゾチオフェニル)ピリジル}(アセチルアセトナート)イリジウム錯体、ビス(2−フェニルベンゾチアゾール)(アセチルアセトナート)イリジウム錯体、ビス(2−フェニルベンゾオキサゾール)(アセチルアセトナート)イリジウム錯体、ビスベンゾキノリン(アセチルアセトナート)イリジウム錯体などがあげられるが特に限定されるものではない。
【0052】
本発明の発光素子において電子輸送性材料は、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。しかしながら、正孔と電子のバランスを考えた場合に、陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たす場合には、電子輸送能力がそれ程高くなくても、発光効率を向上させる効果は電子輸送能力が高い材料と同等に有する。したがって、本発明における電子輸送層は、正孔の移動を効率よく阻止できる正孔阻止層も同義のものとして含まれる。
【0053】
このような条件を満たす物質として、本発明におけるテトラフェニルメタン誘導体や、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、ナフタレン導体、クマリン誘導体、ピリジン誘導体、キノリン誘導体、キノキサリン誘導体、ベンゾキノリン誘導体、フェナントロリン誘導体、チオフェン誘導体、オキサゾール誘導体、チアゾール誘導体、オキサジアゾール誘導体、トリアゾール誘導体、ベンゾチアゾール誘導体、ベンズオキサゾール誘導体、ベンズイミダゾール誘導体、ジフェニルリンオキサイド誘導体、シロール誘導体、トリフェニルシラン誘導体、アルダジン誘導体、ビススチリル誘導体、ピラジン誘導体などがあげられるが特に限定されるものではない。
【0054】
本発明におけるテトラフェニルメタン誘導体は発光材料と電子輸送性材料のいずれにも用いることができるが、電子輸送能と正孔阻止能が高いため、電子輸送性材料として用いることがより好ましい。
【0055】
以上の正孔輸送層、発光層、電子輸送層に用いられる材料は単独または二種類以上の物質を積層、混合して各層を形成することができるが、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。
【0056】
本発明の発光素子において発光物質の形成方法は、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。
【0057】
本発明において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。
【0058】
本発明における発光素子はマトリクスタイプとして用いるのに適している。本発明においてマトリクスとは、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。
【0059】
本発明における発光素子はセグメントタイプとして用いるのに適している。本発明において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。
【0060】
本発明における発光素子はバックライトとして用いるのに適している。本発明においてバックライトとは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ機器、自動車パネル、表示板、標識などに使用される。特に液晶表示装置、中でも薄型化が課題となっているパソコン用途のバックライトとしては、従来方式のものが蛍光灯や導光板からなっているため薄型化が困難であることを考えると本発明におけるバックライトは、薄型、軽量が特徴になる。
【0061】
【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。
【0062】
実施例1(ETM−1の合成)
テトラフェニルメタン2.5g、塩化アルミニウム2.08g、塩化アセチル1.22mlを1,2−ジクロロエタン100mlに加え、室温で1.5時間、次いで70℃で2時間反応させ、常法で処理しジアセチルテトラフェニルメタン1.03gを得た。1H−NMR(CDCl3,ppm):7.86(d,4H)、7.35(d,4H)、7.24(m,10H)。
【0063】
上述のジアセチルテトラフェニルメタン1.0gをジオキサン中で60℃で8−アミノ−7−キノリンカルボアルデヒド1.06g、水酸化カリウム1.0gと反応させ、常法で処理し、下記式に示すETM−1を1.21g得た。1H−NMR(CDCl3,ppm):9.21(d・d,2H)、8.31−8.19(m,8H)、8.07(d,2H)、7.76(q,4H)、7.62(d・d,2H)、7.50(d,4H)、7.39−7.20(m,10H)。
【0064】
【化6】
【0065】
実施例2(ETM−2の合成)
実施例1の方法で合成したジアセチルテトラフェニルメタン0.767gをジオキサン中で2−アミノニコチンアルデヒド0.51g、水酸化カリウム0.76gと4時間加熱還流させ、常法で処理し、下記式に示すETM−2を0.817g得た。1H−NMR(CDCl3,ppm):9.12(d・d,2H)、8.22(m,8H)、8.00(d,2H)、7.46(m,6H)、7.28(m,10H)。
【0066】
【化7】
【0067】
実施例3(ETM−3の合成)
実施例1の方法で合成したジアセチルテトラフェニルメタン1.0gを1.5%水酸化カリウムメタノール溶液中でピリジン−2−アルデヒド1.87mlと室温で反応させ、ろ過、メタノール洗浄し、褐色粉末を得た。この褐色粉末1.0gをエタノール中で2−ピリダジルピリジニウムヨージド1.12g、アンモニウムアセテート1.7gと4時間加熱還流させ、常法で処理し、下記式に示すETM−3を0.43g得た。1H−NMR(CDCl3,ppm):8.92(d,2H)、8.75(d・d,4H)、8.67(d,2H)、8.52(d,2H)、8.18(d,4H)、8.04(d,2H)、7.85(t,4H)、7.47(d,4H)、7.31(m,14H)。
【0068】
【化8】
【0069】
実施例4
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”(フルウチ化学(株)製)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、まず正孔注入材料として、銅フタロシアニンを20nm、正孔輸送材料として、4,4’−ビス(N−(1−ナフチル)−N−フェニルアミノ)ビフェニルを100nm蒸着した。次に発光材料として、トリスキノリノールアルミニウム錯体(Alq3)を50nmの厚さに積層した。次に電子輸送材料として、前述のETM−1を100nmの厚さに積層した。次にリチウムを0.5nm有機層にドーピングした後、アルミニウムを200nm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。この発光素子からは、発光波長530nm、輝度20000カンデラ/平方メートルの高輝度緑色発光が得られた。この発光素子の耐久性は非常に優れたものであり、1000時間で80%以上の輝度を保持した。
【0070】
また、この発光素子を真空セル内で1mAパルス駆動(Duty比1/60、パルス時の電流値60mA)させたところ、良好な発光が確認された。
【0071】
比較例1
電子輸送材料として2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン(BTCPN)を用いた他は実施例4と全く同様にして発光素子を作製した。この発光素子の耐久性は著しく短く、100時間で輝度が半減した。
【0072】
実施例5
発光材料として、ホスト材料としてトリスキノリノールアルミニウム錯体(Alq3)を、ゲスト材料として4−(ジシアノメチレン)−2−tブチル−6−(1,1,7,7−テトラメチルジュロリジル−9−エニル)−4H−ピラン(DCJTB)をドープ濃度が2%になるように用いた他は実施例4と全く同様にして発光素子を作製した。この発光素子からは、発光波長630nm、輝度10000カンデラ/平方メートルの高輝度赤橙色発光が得られた。この発光素子の耐久性は非常に優れたものであり、1000時間で80%以上の輝度を保持した。
【0073】
実施例6
ホスト材料として、4,4’−ビス(ジフェニルビニル)ビフェニル(DPVBi)を用いた他は実施例4と全く同様にして発光素子を作製した。この発光素子からは、発光波長460nm、輝度10000カンデラ/平方メートルの高輝度青色発光が得られた。
【0074】
比較例2
電子輸送材料としてトリスキノリノールアルミニウム錯体(Alq3)を用いた他は実施例6と全く同様にして発光素子を作製した。この発光素子からは発光材料からの発光に加えて電子輸送材料からの緑色発光が観察され、色純度が著しく悪かった。
【0075】
実施例7
ホスト材料として、1,4−ジケト−2,5−ビス(3,5−ジメチルベンジル)−3,6−ビス(4−メチルフェニル)ピロロ[3,4−c]ピロールを、ゲスト材料として4,4−ジフルオロ−1,3,5,7−テトラフェニル−4−ボラ−3a,4a−ジアザ−インダセンをドープ濃度が1%になるように用いた他は実施例5と全く同様にして発光素子を作製した。この発光素子からは、発光波長610nm、輝度10000カンデラ/平方メートルの高輝度赤色発光が得られた。この発光素子の耐久性は非常に優れたものであり、500時間で60%以上の輝度を保持した。
【0076】
実施例8
電子輸送材料として前述のETM−2を用いた他は実施例7と全く同様にして発光素子を作製した。この発光素子からは、発光波長610nm、輝度9500カンデラ/平方メートルの高輝度赤色発光が得られた。この発光素子の耐久性は非常に優れたものであり、500時間で55%以上の輝度を保持した。
【0077】
実施例9
電子輸送材料として前述のETM−3を用いた他は実施例7と全く同様にして発光素子を作製した。この発光素子からは、発光波長610nm、輝度8000カンデラ/平方メートルの高輝度赤色発光が得られた。この発光素子の耐久性は非常に優れたものであり、500時間で55%以上の輝度を保持した。
【0078】
比較例3
電子輸送材料としてトリスキノリノールアルミニウム錯体(Alq3)を用いた他は実施例7と全く同様にして発光素子を作製した。この発光素子からは発光材料からの赤色発光に加えて電子輸送材料からの緑色発光が観察され、色純度が著しく悪かった。
【0079】
実施例10
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、フォトリソグラフィ法によって300μmピッチ(残り幅270μm)×32本のストライプ状にパターン加工した。ITOストライプの長辺方向片側は外部との電気的接続を容易にするために1.27mmピッチ(開口部幅800μm)まで広げてある。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5×10-4Pa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150nm蒸着し、発光材料としてトリスキノリノールアルミニウム錯体を50nmの厚さに蒸着した。次に電子輸送材料として、前述のETM−1を100nmの厚さに積層した。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。次に厚さ50μmのコバール板にウエットエッチングによって16本の250μmの開口部(残り幅50μm、300μmピッチに相当)を設けたマスクを、真空中でITOストライプに直交するようにマスク交換し、マスクとITO基板が密着するように裏面から磁石で固定した。そしてリチウムを0.5nm有機層にドーピングした後、アルミニウムを200nm蒸着して32×16ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
【0080】
【発明の効果】
本発明は、発光効率が高く、高輝度で色純度が良く、しかも耐久性に優れた発光素子を提供できるものである。[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. The present invention relates to an element and a material for a light emitting 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 C.D. W. Since Tang et al. Have shown that organic laminated thin film elements emit light with high brightness (see Non-Patent Document 1), 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. It is provided sequentially, and is 1000 cd / m with a driving voltage of about 10V. 2 Green light emission was possible. 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]
With the aim of realizing a full-color display, light emitting materials are required to have three primary colors (RGB), so far green light emitting materials have been studied most, followed by blue light emitting materials, and most recently red light emitting materials. Improvement is desired and earnest research has been done. As a light emitting material, not only a fluorescent material but also a phosphorescent material has been studied. In addition, as a charge transport material, research on a hole transport material has been active so far, but recently, an electron transport material has been eagerly studied (see, for example, Patent Document 1 and Patent Document 2).
[0005]
[Non-Patent Document 1]
Appl. Phys. Lett. 51 (12) 21, p. 913, 1987 (914 pages)
[0006]
[Patent Document 1]
JP 2000-119644 A (page 17)
[0007]
[Patent Document 2]
International Publication No. 00/03565 Pamphlet (Claims)
[0008]
[Problems to be solved by the invention]
However, many of the light emitting materials, hole transport materials, and electron transport materials used in the prior art are inferior in durability. Crystallization is caused by heat generation from the element due to energization for a long time, and the element life is shortened. In addition, since the material imparted with the amorphous property to suppress the crystallization has a low sublimation property, many of the materials are subject to modification such as decomposition and polymerization during vacuum deposition.
[0009]
An object of the present invention is to solve the problems of the prior art, and to provide a light emitting device having high luminous efficiency, high luminance, good color purity, and excellent durability.
[0010]
That is, the present invention relates to a tetraphenylmethane derivative represented by the general formula (1). Electron transport material having And the Electron transport material Between the anode and cathode Electron transport layer It is the light emitting element used as.
[0011]
[Chemical formula 2]
[0012]
(Where R 1 ~ R 20 Is hydrogen. However, R 1 ~ R 5 At least one of R and R 6 ~ R 10 At least one of Selected from pyridyl, bipyridyl, terpyridyl, quarterpyridyl, quinolinyl, benzoquinolinyl, phenanthroline, acridinyl, naphthyridinyl, pyrazyl, quinoxalinyl, benzoquinoxalinyl or phenazinyl . )
[0013]
DETAILED DESCRIPTION OF THE INVENTION
The novel compound in the present invention is a tetraphenylmethane derivative represented by the following general formula (1).
[0014]
[Chemical 3]
[0015]
(Where R 1 ~ R 20 Is 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, siloxanyl group, ring structure formed between adjacent substituents Chosen from the inside. However, R 1 ~ R Five At least one of R and R 6 ~ R Ten At least one of them is a substituent having a pyridine ring skeleton).
[0016]
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 furyl group, a thienyl 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. A ring structure may be formed between adjacent substituents. The ring structure formed may be unsubstituted or substituted.
[0017]
The substituent having a pyridine ring skeleton refers to a substituent containing one or more pyridyl groups or a polycyclic aromatic group containing a pyridine ring. For example, a pyridyl group, a bipyridyl group, a terpyridyl group, a quarterpyridyl group, A quinolinyl group, a benzoquinolinyl group, a phenanthroline group, an acridinyl group, a naphthyridinyl group and the like may be mentioned, and these may have a substituent other than hydrogen.
[0018]
Instead of the pyridine ring skeleton, a pyrazine ring skeleton in which the carbon atom at the 4-position of the pyridine ring is replaced with a nitrogen atom can also be used. Examples of such a substituent include a pyrazyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a phenazinyl group, and the like, and these may have a substituent other than hydrogen.
[0019]
The substituent having the pyridine ring skeleton or the pyrazine ring skeleton is preferably a polycyclic aromatic group from the viewpoint of heat resistance.
[0020]
In order to effectively express the functionality such as charge transporting property and thin film forming property, R 1 ~ R 20 A functional substituent can also be introduced into at least one of the above. Examples thereof include triphenylamine, diphenylamine, carbazole, indole, diphenylvinyl, fluorenyl, phenanthryl, anthranyl, pyrenyl, perylenyl, biphenyl, terphenyl, quarterphenyl, and other charge transporting substituents, alkyl groups, alkoxy groups, Although there are thin film forming substituents such as aryl ether groups, it is not particularly limited.
[0021]
The number of substituents having a pyridine ring skeleton is not particularly limited, but is preferably 2 or more and 4 or less, and more preferably 2. In one case, the charge transportability is low and the function expression may be insufficient, and in the case of five or more, synthesis and purification are difficult, or because of low sublimation, modification such as decomposition or polymerization is caused during vacuum deposition. It may happen.
[0022]
The position of the substituent having a pyridine ring skeleton is not particularly limited. 2 , R Three , R Four , R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 R is preferable from the viewpoint of heat resistance. Three , R 8 , R 13 , R 18 Is more preferable.
[0023]
The substituent having a pyridine ring skeleton may be directly bonded to the tetraphenylmethane skeleton, or a divalent linking group may be interposed between the substituent and the tetraphenylmethane skeleton. The divalent linking group in this case is not particularly limited, but includes an alkyl group, an ether group, a thioether group, a ketone group, a substituted or unsubstituted amino group, an amide group, an aryl group, a heterocyclic group, and the like. Can be mentioned. From the viewpoint of ease of synthesis and heat resistance, the functional substituent is preferably bonded directly or via an aryl group or heterocyclic group as a divalent linking group.
[0024]
The compound represented by the general formula (1) can be synthesized by the following method, but is not particularly limited.
[0025]
For the synthesis of the tetraphenylmethane skeleton, reference is made to Angew. Chem. Int. Ed. Engl. vol. 25 (1986) No. 25. 12, page 1098, Tetrahedron Letters, vol. 38 (1997), page 1487, and the like. Specifically, triphenylmethanol or triphenylmethyl chloride is reacted with aniline or aniline hydrochloride at 100 ° C. to 220 ° C. in a solvent-free or acetic acid solvent, and the resulting intermediate is treated by a conventional method. And then reacted with isoamyl nitrite in a mixed solvent of ethanol / sulfuric acid at −10 ° C., added with phosphinic acid, heated to reflux and treated in a conventional manner.
[0026]
The introduction of a substituent having a pyridine ring skeleton into the tetraphenylmethane skeleton or the above-described functional substituent may be direct, but a method of first introducing a reactive substituent and then introducing the substituent is preferred. Examples of the reactive substituent include, but are not particularly limited to, an acetyl group, an iodo group, and a bromo group.
[0027]
Examples of the method for introducing an acetyl group include general and simple acylation of Friedel-Crafts. Examples of references include “Example A. Starting compound (f) 2,2′-diacetyl-9,9′-spirobifluorene” on page 27 of JP-A-7-278537, Helvetica Chimica Acta, vol. 52 (1969), page 1210, “Experimenteller Tell 2,2′-diacetyl-9,9′-spirobifluorene (IV)”. Specifically, tetraphenylmethane can be reacted with acetyl chloride and aluminum chloride in 1,2-dichloroethane at 50 ° C. and treated in a conventional manner to introduce an acetyl group. By changing the equivalent of acetyl chloride and aluminum chloride, 1 to 4 substituents can be obtained.
[0028]
For introduction of an iodo group, reference is made to Tetrahedron Letters, vol. 38 (1997), page 1487, and the like. Specifically, tetraphenylmethane can be reacted with iodine and bis (trifluoroacetoxy) iodobenzene at 50 ° C. to 60 ° C. in carbon tetrachloride and treated in a conventional manner to introduce an iodo group.
[0029]
Regarding the introduction of bromo group, the above-mentioned Angew. Chem. Int. Ed. Engl. 25 (1986) No. 25. 12 page 1098 and the like. Specifically, tetraphenylmethane can be reacted with bromine at room temperature and treated in a conventional manner to introduce a bromo group. By changing the equivalent of bromine, 1 to 4 substituents can be obtained.
[0030]
For the introduction of a substituent having a pyridine ring skeleton or a functional substituent into the tetraphenylmethane skeleton after the introduction of the reactive substituent, from the acetyl group to the phenanthroline group, benzoquinolinyl group, naphthyridinyl group, terpyridyl group, indole group Introduction, iodo group, bromo group to phenanthroline group, bipyridyl group, terpyridyl group, diphenylamino group, carbazole group, diphenylethylene group, polyphenylene group, n-butyl group and the like can be mentioned but are not particularly limited.
[0031]
For introduction of a phenanthroline group, Tetrahedron Letters, vol. 40 (1999). Page 7312 scheme and J.P. Org. Chem. 1996, 61. Page 3020 “2-Phenyl-1,10-phenanthroline”, Tetrahedron Letters, vol. 23 (1982). Page 5291 to page 5294. Specifically, a method of reacting an acetyl form of tetraphenylmethane with 8-amino-7-quinolinecarbaldehyde and potassium hydroxide in dioxane at 60 ° C. and treating by an ordinary method, an iodine form of tetraphenylmethane, A phenanthroline group can be introduced by, for example, a method in which a bromo compound is lithiated with lithium metal and then reacted with anhydrous phenanthroline and treated with water or manganese dioxide.
[0032]
For the introduction of indole groups, reference is made to Tetrahedron Letters, vol. 40 (1999). A 73rd page scheme etc. are mention | raise | lifted. Specifically, the acetylated form of tetraphenylmethane and 1-methyl-1-phenylhydrazine were heated to reflux in ethanol, acetic acid was added and further heated to reflux, and treated in the usual manner to obtain a hydrazine form. Can be heated in polyphosphoric acid at 160 ° C. and treated in a conventional manner to introduce indole groups.
[0033]
For introduction of diphenylethylene group, reference is made to SPIE, vol. 3797. Page 317 "2.1 Synthesis EM1". Specifically, diphenylvinylboronic acid, sodium carbonate, and tetrakis (triphenylphosphine) palladium catalyst are added to the bromo form of tetraphenylmethane, reacted at 100 ° C. in water-toluene, treated in a conventional manner, and diphenylvinyl Groups can be introduced. Similarly, polyphenylene can be introduced.
[0034]
For introduction of the diphenylamino group, reference is made to SPIE, vol. 3797. Page 317 "2.1 Synthesis HTM1". Specifically, diphenylamine, t-butoxy sodium, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, and palladium acetate are added to the bromo form of tetraphenylmethane, and heated to reflux in toluene. The diphenylamino group can be introduced by a conventional method. Similarly, a carbazolyl group can be introduced.
[0035]
Regarding the introduction of the n-butyl group, specifically, the n-butyl group can be introduced by reacting the bromo form of tetraphenylmethane with n-butyllithium in THF at room temperature and treating it in a conventional manner. The unreacted bromo group remaining at the time of introducing the above-mentioned functional substituent from the bromo form of tetraphenylmethane can be treated, which is advantageous for thin film formation.
[0036]
Specific examples of the tetraphenylmethane derivative include the following structures, but are not particularly limited.
[0037]
[Formula 4]
[0038]
[Chemical formula 5]
[0039]
Moreover, this invention is represented by the said General formula (1). Electron transport material Between the anode and cathode Electron transport layer It is the light emitting element used as.
[0040]
Since the tetraphenylmethane derivative represented by the general formula (1) has a three-dimensional skeleton, it has high heat resistance, prevents crystallization, and is excellent in thin film formation. Furthermore, it is chemically and electrochemically stable, has no characteristics such as decomposition or polymerization during vacuum deposition, and has extremely excellent durability.
[0041]
In the light emitting device of the present invention, if the anode is transparent for extracting light, a conductive metal oxide such as tin oxide, indium oxide, indium tin oxide (ITO), or a metal such as gold, silver, or chromium, or iodide Inorganic conductive materials such as copper and copper sulfide, 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, it is better to use alkali-free glass because it is better to have less ions eluted from the glass. 2 Since soda lime glass with a barrier coating such as is commercially available, it 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.
[0042]
In the light emitting device of the present invention, the cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium , Sodium, potassium, calcium, magnesium, etc., but lithium, sodium, potassium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. . 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, cesium, or magnesium (1 nm or less in the thickness gauge display of vacuum deposition). A method using a highly stable electrode can be mentioned as a preferable example, but an inorganic salt such as lithium fluoride can also be used, and the method is not particularly limited thereto. 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.
[0043]
In the light emitting device of the present invention, 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, and 4) Any of the mixed substances may be mixed. That is, as the element structure, in addition to the multilayer laminated structure of the above 1) to 3), only the light emitting material alone or a layer containing the light emitting material and the hole transport material or electron transport material may be provided as in 4). Furthermore, the light-emitting substance in the light-emitting element of 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, and the like that are involved in light emission.
[0044]
In the light emitting device of the present invention, the hole transporting material is required to efficiently transport holes from the anode between electrodes to which an electric field is applied, and the hole injection efficiency is high. It is desirable to transport well. For this purpose, it is required that the ionization potential is low, the hole mobility is high, the stability is high, and the trapping impurities are difficult to be generated during production and use.
[0045]
Examples of substances satisfying such conditions include N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′-diamine, and N, N′-dinaphthyl. -Triphenylamines such as -N, N'-diphenyl-4,4'-diphenyl-1,1'-diamine, carbazoles such as bis (N-allylcarbazole) and bis (N-alkylcarbazole) s, Indole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, oxadiazole derivatives, phthalocyanine derivatives, heterocyclic compounds typified by porphyrin derivatives, in the case of polymers, polycarbonates or styrene derivatives having the above-mentioned monomers in the side chain, polyvinyl Examples thereof include carbazole and polysilane, but are not particularly limited.
[0046]
The light emitting material in the present invention 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.
[0047]
In the light emitting device of the present invention, the light emitting material is required to efficiently recombine the holes received from the hole transport layer or the direct anode and the electrons received from the electron transport layer or the direct cathode, and includes a dopant material. It is necessary to efficiently transfer the recombination energy to the dopant material. Furthermore, it is required to be a substance that is excellent in stability and is unlikely to generate trapping impurities during manufacturing and use.
[0048]
As a substance satisfying such conditions, the tetraphenylmethane derivative in the present invention, condensed ring derivatives such as anthracene, phenanthrene, pyrene, perylene, chrysene, etc., which have been known as light emitters, tris (8-quinolinolato) aluminum are used. Starting metal complexes of quinolinol derivatives, benzoxazole derivatives, stilbene derivatives, benzthiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, oxadiazole derivatives, bisstyrylanthracene derivatives, distyrylbenzene derivatives, etc. Bisstyryl derivatives, metal complexes combining quinolinol derivatives with different ligands, oxadiazole derivative metal complexes, benzazole derivative metal complexes, coumarin derivatives , Pyrrolopyridine derivatives, pyrrolopyrrole derivatives, silole derivatives, perinone derivatives, thiadiazolopyridine derivatives, polymer systems include polyphenylene vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives, but are not particularly limited. Absent.
[0049]
The dopant material added to the light-emitting material needs to efficiently receive recombination energy from the host material, and desirably has a high quantum yield and hardly causes concentration quenching. Furthermore, it is required to be a substance that is excellent in stability and is unlikely to generate trapping impurities during manufacturing and use.
[0050]
Substances satisfying such conditions include tetraphenylmethane derivatives in the present invention, conventionally known condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, and rubrene, benz Oxazole derivatives, benzthiazole derivatives, benzimidazole derivatives, benztriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclo Bisstyryl derivatives such as pentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives, diazaindacene Conductor, furan derivative, benzofuran derivative, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) isobenzofuran, di (2-trifluoromethylphenyl) isobenzofuran, isobenzofuran derivatives such as phenylisobenzofuran, dibenzofuran Derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzthiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives , Coumarin derivatives such as 3-benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzua Thracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazo Lopylene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, diazaflavin derivatives and the like can be mentioned, but are not particularly limited.
[0051]
As the dopant material, not only the fluorescent (singlet light emission) material but also a phosphorescent (triplet light emission) material is preferably used. Specifically, porphyrin platinum complex, tris (2-phenylpyridyl) iridium complex, tris {2- (2-thiophenyl) pyridyl} iridium complex, tris {2- (2-benzothiophenyl) pyridyl} iridium complex, tris (2-phenylbenzothiazole) iridium complex, tris (2-phenylbenzoxazole) iridium complex, trisbenzoquinoline iridium complex, bis (2-phenylpyridyl) (acetylacetonato) iridium complex, bis {2- (2-thiophenyl) ) Pyridyl} iridium complex, bis {2- (2-benzothiophenyl) pyridyl} (acetylacetonato) iridium complex, bis (2-phenylbenzothiazole) (acetylacetonato) iridium complex, bis (2-phenylbenzooxa) Z Le) (acetylacetonato) iridium complex, bis benzoquinoline (acetylacetonate), but such an iridium complex and the like are not particularly limited.
[0052]
In the light-emitting element of the present invention, the electron transporting material needs to efficiently transport electrons from the cathode between electrodes to which an electric field is applied, and has high electron injection efficiency and efficiently transports injected electrons. Is desirable. 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. However, considering the balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is so high. Even if not, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
[0053]
Examples of substances satisfying such conditions include tetraphenylmethane derivatives in the present invention, quinolinol derivative metal complexes represented by 8-hydroxyquinoline aluminum, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene conductors, coumarins. Derivatives, pyridine derivatives, quinoline derivatives, quinoxaline derivatives, benzoquinoline derivatives, phenanthroline derivatives, thiophene derivatives, oxazole derivatives, thiazole derivatives, oxadiazole derivatives, triazole derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, diphenyl phosphorus oxide Derivatives, silole derivatives, triphenylsilane derivatives, aldazine derivatives, bisstyryl derivatives, pyrazine derivatives, etc. It is not limited in particular.
[0054]
The tetraphenylmethane derivative in the present invention can be used for either a light emitting material or an electron transporting material, but is more preferably used as an electron transporting material because of its high electron transporting ability and hole blocking ability.
[0055]
The materials used for the hole transport layer, the light emitting layer, and the electron transport layer can be formed by laminating and mixing two or more kinds of substances, and each layer can be formed by using polyvinyl chloride as a polymer binder, 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 Used by dispersing in solvent-soluble resins such as resins and polyurethane resins, and curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins. Rukoto is also possible.
[0056]
In the light emitting device of the present invention, the method for forming the luminescent material is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, and coating method. It is preferable in terms of characteristics. The thickness of the layer depends on the resistance value of the luminescent material and cannot be limited, but is selected from 1 to 1000 nm.
[0057]
In the present invention, electrical energy mainly refers to a direct current, but a pulse current or an 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.
[0058]
The light-emitting element in the present invention is suitable for use as a matrix type. In the present invention, the matrix refers to a matrix in which pixels for display are arranged in a grid pattern, and a character or image is displayed 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.
[0059]
The light emitting device in the present invention is suitable for use as a segment type. In the present invention, the segment type 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.
[0060]
The light emitting element in the present invention is suitable for use as a backlight. In the present invention, the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for a liquid crystal display device, in particular, a personal computer application for which thinning is an issue, it is difficult to reduce the thickness of the conventional method because it is made of a fluorescent lamp or a light guide plate. The backlight is thin and lightweight.
[0061]
【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.
[0062]
Example 1 (Synthesis of ETM-1)
Add 2.5 g of tetraphenylmethane, 2.08 g of aluminum chloride, and 1.22 ml of acetyl chloride to 100 ml of 1,2-dichloroethane, react at room temperature for 1.5 hours, then at 70 ° C. for 2 hours, treat in the usual manner, and diacetyl. 1.03 g of tetraphenylmethane was obtained. 1 H-NMR (CDCl Three , Ppm): 7.86 (d, 4H), 7.35 (d, 4H), 7.24 (m, 10H).
[0063]
ETM shown in the following formula is obtained by reacting 1.0 g of the above-mentioned diacetyltetraphenylmethane with 1.06 g of 8-amino-7-quinolinecarbaldehyde and 1.0 g of potassium hydroxide in dioxane at 60 ° C. 1.21 g of -1 was obtained. 1 H-NMR (CDCl Three , Ppm): 9.21 (d · d, 2H), 8.31-8.19 (m, 8H), 8.07 (d, 2H), 7.76 (q, 4H), 7.62 ( d · d, 2H), 7.50 (d, 4H), 7.39-7.20 (m, 10H).
[0064]
[Chemical 6]
[0065]
Example 2 (Synthesis of ETM-2)
0.767 g of diacetyltetraphenylmethane synthesized by the method of Example 1 was heated to reflux with 0.51 g of 2-aminonicotinaldehyde and 0.76 g of potassium hydroxide in dioxane for 4 hours and treated in the usual manner. 0.817 g of the indicated ETM-2 was obtained. 1 H-NMR (CDCl Three , Ppm): 9.12 (d · d, 2H), 8.22 (m, 8H), 8.00 (d, 2H), 7.46 (m, 6H), 7.28 (m, 10H) .
[0066]
[Chemical 7]
[0067]
Example 3 (Synthesis of ETM-3)
1.0 g of diacetyltetraphenylmethane synthesized by the method of Example 1 was reacted with 1.87 ml of pyridine-2-aldehyde in a 1.5% potassium hydroxide methanol solution at room temperature, filtered, washed with methanol, Obtained. 1.0 g of this brown powder was heated to reflux with 1.12 g of 2-pyridazylpyridinium iodide and 1.7 g of ammonium acetate in ethanol for 4 hours and treated in a conventional manner. 43 g was obtained. 1 H-NMR (CDCl Three , Ppm): 8.92 (d, 2H), 8.75 (d · d, 4H), 8.67 (d, 2H), 8.52 (d, 2H), 8.18 (d, 4H) 8.04 (d, 2H), 7.85 (t, 4H), 7.47 (d, 4H), 7.31 (m, 14H).
[0068]
[Chemical 8]
[0069]
Example 4
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” (manufactured by Furuuchi Chemical Co., Ltd.) 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 treated with UV-ozone for 1 hour immediately before producing the device, and placed in a vacuum vapor deposition apparatus. The degree of vacuum in the apparatus was 5 × 10 -Five It exhausted until it became Pa or less. By the resistance heating method, first, copper phthalocyanine was deposited to 20 nm as a hole injecting material, and 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited to 100 nm as a hole transporting material. Next, a triskinolinol aluminum complex (Alq3) was laminated to a thickness of 50 nm as a light emitting material. Next, the above-mentioned ETM-1 was laminated to a thickness of 100 nm as an electron transport material. Next, after doping the organic layer with 0.5 nm of lithium, aluminum was deposited to 200 nm to form a cathode, and a 5 × 5 mm square device was produced. The film thickness mentioned here is a display value of a crystal oscillation type film thickness monitor. From this light-emitting element, high-luminance green light emission having an emission wavelength of 530 nm and a luminance of 20,000 candela / square meter was obtained. The durability of this light-emitting element was very excellent, and maintained a luminance of 80% or more in 1000 hours.
[0070]
Further, when this light emitting element was driven in a vacuum cell by 1 mA pulse (Duty ratio 1/60, current value at the time of pulse 60 mA), good light emission was confirmed.
[0071]
Comparative Example 1
A light emitting device was produced in the same manner as in Example 4 except that 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BTCPN) was used as the electron transport material. The durability of this light emitting device was extremely short, and the luminance was reduced by half in 100 hours.
[0072]
Example 5
Trisquinolinol aluminum complex (Alq3) as the host material and 4- (dicyanomethylene) -2-tbutyl-6- (1,1,7,7-tetramethyljulolidyl-9- as the guest material A light emitting device was fabricated in exactly the same manner as in Example 4 except that enyl) -4H-pyran (DCJTB) was used so that the doping concentration was 2%. From this light-emitting element, high-luminance red-orange light emission with an emission wavelength of 630 nm and a luminance of 10,000 candela / square meter was obtained. The durability of this light-emitting element was very excellent, and maintained a luminance of 80% or more in 1000 hours.
[0073]
Example 6
A light emitting device was fabricated in exactly the same manner as in Example 4 except that 4,4′-bis (diphenylvinyl) biphenyl (DPVBi) was used as the host material. From this light-emitting element, high-luminance blue light emission with an emission wavelength of 460 nm and a luminance of 10,000 candela / square meter was obtained.
[0074]
Comparative Example 2
A light emitting device was fabricated in exactly the same manner as in Example 6 except that triskinolinol aluminum complex (Alq3) was used as the electron transporting material. From this light emitting element, green light emission from the electron transport material was observed in addition to light emission from the light emitting material, and the color purity was extremely poor.
[0075]
Example 7
1,4-diketo-2,5-bis (3,5-dimethylbenzyl) -3,6-bis (4-methylphenyl) pyrrolo [3,4-c] pyrrole as the host material and 4 as the guest material , 4-difluoro-1,3,5,7-tetraphenyl-4-bora-3a, 4a-diaza-indacene was used in the same manner as in Example 5 except that the doping concentration was 1%. An element was produced. From this light-emitting element, high-luminance red light emission having an emission wavelength of 610 nm and a luminance of 10,000 candela / square meter was obtained. The durability of this light-emitting element was extremely excellent, and the luminance of 60% or more was maintained in 500 hours.
[0076]
Example 8
A light emitting device was fabricated in exactly the same manner as in Example 7 except that ETM-2 was used as the electron transport material. From this light-emitting element, high-luminance red light emission having an emission wavelength of 610 nm and a luminance of 9500 candela / square meter was obtained. The durability of this light emitting element was very excellent, and the luminance of 55% or more was maintained in 500 hours.
[0077]
Example 9
A light emitting device was fabricated in exactly the same manner as in Example 7 except that ETM-3 was used as the electron transport material. From this light-emitting element, high-luminance red light emission having an emission wavelength of 610 nm and a luminance of 8000 candela / square meter was obtained. The durability of this light emitting element was very excellent, and the luminance of 55% or more was maintained in 500 hours.
[0078]
Comparative Example 3
A light emitting device was fabricated in exactly the same manner as in Example 7 except that triskinolinol aluminum complex (Alq3) was used as the electron transporting material. From this light emitting element, in addition to red light emission from the light emitting material, green light emission from the electron transport material was observed, and the color purity was extremely poor.
[0079]
Example 10
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporation product) on which an ITO transparent conductive film is deposited to 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 stripes by photolithography. Patterned into a shape. One side of the ITO stripe in the long side direction is expanded to a 1.27 mm pitch (opening width 800 μm) in order to facilitate electrical connection with the outside. 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 treated with UV-ozone for 1 hour immediately before producing the device, and placed in a vacuum vapor deposition apparatus. The degree of vacuum in the apparatus was 5 × 10 -Four It exhausted until it became Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl is deposited as a hole transport material by 150 nm by resistance heating, and a triskinolinol aluminum complex is formed as a light emitting material to a thickness of 50 nm. Vapor deposited. Next, the above-mentioned ETM-1 was laminated to a thickness of 100 nm as an electron transport material. The film thickness mentioned here is a display value of a crystal oscillation type film thickness monitor. Next, the mask in which 16 250 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) were formed by wet etching on a 50 μm thick Kovar plate was replaced in a vacuum so as to be orthogonal to the ITO stripe. And it fixed with the magnet from the back so that an ITO board | substrate might closely_contact | adhere. And after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited 200 nm, and the 32x16 dot matrix element was produced. When this element was driven in matrix, characters could be displayed without crosstalk.
[0080]
【The invention's effect】
The present invention can provide a light-emitting element having high luminous efficiency, high luminance, good color purity, and excellent durability.
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JP4561221B2 (en) * | 2003-07-31 | 2010-10-13 | 三菱化学株式会社 | Compound, charge transport material and organic electroluminescence device |
DE10357315A1 (en) * | 2003-12-05 | 2005-07-07 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
JP4351935B2 (en) | 2004-03-10 | 2009-10-28 | 富士フイルム株式会社 | Organic electroluminescence device |
JP4352008B2 (en) * | 2004-03-10 | 2009-10-28 | 富士フイルム株式会社 | Light emitting element |
JP2007084458A (en) * | 2005-09-20 | 2007-04-05 | Chemiprokasei Kaisha Ltd | 1,8-naphthyridine derivative and organic electroluminescent element comprising the same |
JP5176366B2 (en) * | 2006-03-30 | 2013-04-03 | Jnc株式会社 | Novel bipyridine derivative and organic electroluminescent device containing the same |
CN101096357B (en) * | 2006-06-26 | 2012-05-30 | 清华大学 | Tetrabenzene methane derivative and its application |
KR100819761B1 (en) | 2006-09-16 | 2008-04-07 | (주)파인켐 | Tetrakisphenyl Compounds And Organic Elecroluminescence Devices Using The Same |
JP5176343B2 (en) * | 2007-03-07 | 2013-04-03 | Jnc株式会社 | Electron transport material and organic electroluminescent device using the same |
JP2009215190A (en) | 2008-03-07 | 2009-09-24 | Fujifilm Corp | Compound having tetraphenylmethane skeleton |
JP4844585B2 (en) * | 2008-04-14 | 2011-12-28 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
EP2299510A4 (en) | 2008-06-11 | 2012-03-28 | Hodogaya Chemical Co Ltd | Organic electroluminescent element |
US10431748B2 (en) * | 2014-10-30 | 2019-10-01 | Lg Chem, Ltd. | Cyclic compound and organic light-emitting element comprising same |
KR102120517B1 (en) * | 2016-04-28 | 2020-06-08 | 주식회사 엘지화학 | Organic light emitting device |
KR102044057B1 (en) * | 2016-04-28 | 2019-11-12 | 주식회사 엘지화학 | Organic light emitting device |
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