JP2009057445A - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- JP2009057445A JP2009057445A JP2007225260A JP2007225260A JP2009057445A JP 2009057445 A JP2009057445 A JP 2009057445A JP 2007225260 A JP2007225260 A JP 2007225260A JP 2007225260 A JP2007225260 A JP 2007225260A JP 2009057445 A JP2009057445 A JP 2009057445A
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- light
- light emitting
- derivatives
- aryl
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- 239000000463 material Substances 0.000 title claims abstract description 115
- -1 chrysene compound Chemical class 0.000 claims abstract description 40
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000002019 doping agent Substances 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000005013 aryl ether group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000000101 thioether group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 28
- 230000032258 transport Effects 0.000 description 28
- 239000000758 substrate Substances 0.000 description 15
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
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- 239000002184 metal Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 125000001931 aliphatic group Chemical group 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
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- 238000006862 quantum yield reaction Methods 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- 150000004832 aryl thioethers Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000005578 chrysene group Chemical group 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 150000005041 phenanthrolines Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
- 238000000746 purification 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- KXMKGOPUYUWQHC-UHFFFAOYSA-N 2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C=4C=CC=C(C=4)C=4N=C5C6=NC=CC=C6C=CC5=CC=4)=CC=C3C=CC2=C1 KXMKGOPUYUWQHC-UHFFFAOYSA-N 0.000 description 2
- RULVBMDEPWAFIN-UHFFFAOYSA-N 6,12-dibromochrysene Chemical compound C1=CC=C2C(Br)=CC3=C(C=CC=C4)C4=C(Br)C=C3C2=C1 RULVBMDEPWAFIN-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
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- 150000004982 aromatic amines Chemical class 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
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- 150000001907 coumarones Chemical class 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 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
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- 229910017053 inorganic salt Inorganic materials 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 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 2
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
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- 238000001771 vacuum deposition Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
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- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
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Abstract
Description
アプライド フィジクス レターズ(Applied Physics Letters)、(米国)、1987年、51巻、12号、913−915頁
また、本発明は、少なくとも陽極、陰極および発光層を有し、該陽極と該陰極の間に該発光層が存在し、該発光層が電気エネルギーにより発光する発光素子であって、該発光層が一般式(1)で表されるクリセン化合物を含有する発光素子である。
クリセン1.2g、N−ブロモスクシンイミド2.2gとジメチルホルムアミド52mlの混合溶液を窒素気流下、室温で11時間撹拌した。溶液に水50mlを注入し、析出物をろ過した。ろ別した固体を水50ml、メタノール50mlでそれぞれ洗浄した後、真空乾燥して、6,12−ジブロモクリセン1.4gを乳白色粉末として得た。
1H−NMR(CDCl3(d=ppm)):7.27-7.44(m, 6H), 7.68-7.84(m, 8H), 8.61-8.65(m, 2H), 8.96(m, 2H), 9.16(s, 2H)。
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に切断し、ITO導電膜をフォトリソグラフィー法によりパターン加工して、発光部分および電極引き出し部分を作製した。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。素子を作製する直前にこの基板を1時間UV−オゾン処理し、さらに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10nm、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50nm蒸着した。次に、発光材料として、ホスト材料として下記式に示すH−1を、またドーパント材料として化合物[29]をドープ濃度が2%になるように35nmの厚さに蒸着した。次に、電子輸送材料として、下記式に示すE−1を20nmの厚さに積層した。以上で形成した有機層上に、フッ化リチウムを0.5nmの厚さに蒸着した後、アルミニウムを1000nm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の表示値である。この発光素子を10mA/cm2で直流駆動したところ、発光効率3.3lm/Wの高効率発光と、C.I.E色度座標で(0.15,0.16)と高色純度の青色発光が得られた。
ドーパント材料として下記式に示すD−1を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、1.6lm/Wの発光効率と、C.I.E色度座標で(0.15,0.18)の青色発光が得られた。
ドーパント材料として下記式に示すD−2を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、3.3lm/Wの発光効率と、C.I.E色度座標で(0.18,0.38)の青緑色発光が得られた。
ドーパント材料として下記式に示すD−3を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率1.8lm/Wの発光効率と、C.I.E色度座標で(0.15,0.15)と高色純度の青色発光が得られた。
ドーパント材料として下記式に示すD−4を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率1.7lm/Wの発光効率と、C.I.E色度座標で(0.15,0.20)の青色発光が得られた。
ホスト材料として下記式に示すH−2を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率3.5lm/Wの発光効率と、C.I.E色度座標で(0.15,0.16)と高色純度の青色発光が得られた。
ホスト材料としてH−2、ドーパント材料として化合物[29]、電子輸送材料としてE−2を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率2.4lm/Wの発光効率と、C.I.E色度座標で(0.15,0.16)と高色純度の青色発光が得られた。
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に切断し、フォトリソグラフィー法によって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”(商品名、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5×10−4Pa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−(1−ナフチル)−N−フェニルアミノ)ビフェニルを150nm蒸着した。次に、ホスト材料としてH−1を、またドーパント材料として化合物[29]をドープ濃度が2%になるように35nmの厚さに蒸着した。次に、電子輸送材料としてE−1を20nm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。そしてフッ化リチウムを0.5nm蒸着した後、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。
Claims (6)
- 一般式(1)で表されるクリセン化合物を含有することを特徴とする発光素子材料。
- Xが酸素原子であることを特徴とする請求項1記載の発光素子材料。
- R2またはR8のうち少なくとも1つが二環式ベンゾへテロ環との連結に用いられることを特徴とする請求項1記載の発光素子材料。
- 陽極と陰極の間に少なくとも発光層が存在し、電気エネルギーにより発光する発光素子であって、発光素子が請求項1〜3のいずれか記載の発光素子材料を含有することを特徴とする発光素子。
- 発光層がホスト材料とドーパント材料を有し、一般式(1)で表される発光素子材料がドーパント材料であることを特徴とする請求項4記載の発光素子。
- 発光層と陰極の間に少なくとも電子輸送層が存在し、電子輸送層が、電子受容性窒素を含み、さらに炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成されるヘテロアリール環構造を有する化合物を含有することを特徴とする請求項4記載の発光素子。
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JP2011046616A (ja) * | 2009-08-25 | 2011-03-10 | Canon Inc | 複素環化合物及びこれを用いた有機発光素子 |
CN104710397A (zh) * | 2013-12-12 | 2015-06-17 | 三星显示有限公司 | 基于胺的化合物以及包含该化合物的有机发光装置 |
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JPH05109485A (ja) * | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
JP2001291590A (ja) * | 2000-04-05 | 2001-10-19 | Toray Ind Inc | 発光素子 |
JP2003142263A (ja) * | 2001-10-30 | 2003-05-16 | Matsushita Electric Ind Co Ltd | 発光素子およびこれを用いた装置 |
US20080122344A1 (en) * | 2006-11-24 | 2008-05-29 | Samsung Electronics Co., Ltd. | Organic light emitting compound and organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
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JPH05109485A (ja) * | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
JP2001291590A (ja) * | 2000-04-05 | 2001-10-19 | Toray Ind Inc | 発光素子 |
JP4590678B2 (ja) * | 2000-04-05 | 2010-12-01 | 東レ株式会社 | 発光素子 |
JP2003142263A (ja) * | 2001-10-30 | 2003-05-16 | Matsushita Electric Ind Co Ltd | 発光素子およびこれを用いた装置 |
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JP2011046616A (ja) * | 2009-08-25 | 2011-03-10 | Canon Inc | 複素環化合物及びこれを用いた有機発光素子 |
US8877354B2 (en) | 2009-08-25 | 2014-11-04 | Canon Kabushiki Kaisha | Heterocyclic compound and organic light-emitting device using the same |
CN104710397A (zh) * | 2013-12-12 | 2015-06-17 | 三星显示有限公司 | 基于胺的化合物以及包含该化合物的有机发光装置 |
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