JP2004204238A - 有機電界発光デバイス - Google Patents
有機電界発光デバイス Download PDFInfo
- Publication number
- JP2004204238A JP2004204238A JP2003428297A JP2003428297A JP2004204238A JP 2004204238 A JP2004204238 A JP 2004204238A JP 2003428297 A JP2003428297 A JP 2003428297A JP 2003428297 A JP2003428297 A JP 2003428297A JP 2004204238 A JP2004204238 A JP 2004204238A
- Authority
- JP
- Japan
- Prior art keywords
- electroluminescent device
- organic electroluminescent
- light emitting
- phenyl
- emitting layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000126 substance Substances 0.000 claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 239000002019 doping agent Substances 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- -1 methylnaphthyl Chemical group 0.000 claims description 30
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 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 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000005023 xylyl group Chemical group 0.000 claims description 3
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 0 *c(cc1)c(cc2)c3c1ccc1c3c2ccc1* Chemical compound *c(cc1)c(cc2)c3c1ccc1c3c2ccc1* 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JWNYMTIPXIPLLP-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound BrC1=CC=C2C=CC3=C(C=CC4=CC=C1C2=C34)Br.BrC3=CC=C4C=CC2=C(C=CC1=CC=C3C4=C21)Br JWNYMTIPXIPLLP-UHFFFAOYSA-N 0.000 description 3
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 210000003739 neck Anatomy 0.000 description 3
- OCHXGVHPQUXRPZ-UHFFFAOYSA-N 1-n,6-n-bis(4-tert-butylphenyl)-1-n,6-n-dipyridin-2-ylpyrene-1,6-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC(=CC=1)C(C)(C)C)C=1N=CC=CC=1)C1=CC=CC=N1 OCHXGVHPQUXRPZ-UHFFFAOYSA-N 0.000 description 2
- MVYXURQVMDWUTH-UHFFFAOYSA-N BrC1=CC=C(C=C1)[Si](C)(C)C.BrC1=CC=C(C=C1)[Si](C)(C)C Chemical compound BrC1=CC=C(C=C1)[Si](C)(C)C.BrC1=CC=C(C=C1)[Si](C)(C)C MVYXURQVMDWUTH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JLJKMPGBYBVUDH-UHFFFAOYSA-N n-(4-tert-butylphenyl)pyridin-2-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC=N1 JLJKMPGBYBVUDH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 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
- UKTSSJJZFVGTCG-UHFFFAOYSA-N (4-bromophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C(Br)C=C1 UKTSSJJZFVGTCG-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- MRQIUQOCJLNMNV-UHFFFAOYSA-N 1,7-dibromopyrene Chemical compound C1=CC(Br)=C2C=CC3=CC(Br)=CC4=CC=C1C2=C43 MRQIUQOCJLNMNV-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound 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 1
- WTEJYGDMCOWSLV-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetraphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WTEJYGDMCOWSLV-UHFFFAOYSA-N 0.000 description 1
- BOXPMFPBOOGIEV-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1.BrC1=CC=CC=N1 BOXPMFPBOOGIEV-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- GVBNIHLZQAXTKT-UHFFFAOYSA-N 4-tert-butyl-n-(4-trimethylsilylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C([Si](C)(C)C)C=C1 GVBNIHLZQAXTKT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WZDONLDYPJNNSZ-UHFFFAOYSA-N Bc1ccc(cc2)c3c1ccc1ccc(B)c2c31 Chemical compound Bc1ccc(cc2)c3c1ccc1ccc(B)c2c31 WZDONLDYPJNNSZ-UHFFFAOYSA-N 0.000 description 1
- GSGLXWSBQRWSLA-UHFFFAOYSA-N BrC1=CC=C2C=CC3=CC=C(C4=CC=C1C2=C34)Br.BrC3=CC=C4C=CC2=CC=C(C1=CC=C3C4=C21)Br Chemical compound BrC1=CC=C2C=CC3=CC=C(C4=CC=C1C2=C34)Br.BrC3=CC=C4C=CC2=CC=C(C1=CC=C3C4=C21)Br GSGLXWSBQRWSLA-UHFFFAOYSA-N 0.000 description 1
- CQTBMEKTYQLIOZ-UHFFFAOYSA-N C(C)(C)(C)C1=C(C=CC=C1)C1(CC=C(C=C1)N)[Si](C)(C)C Chemical compound C(C)(C)(C)C1=C(C=CC=C1)C1(CC=C(C=C1)N)[Si](C)(C)C CQTBMEKTYQLIOZ-UHFFFAOYSA-N 0.000 description 1
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- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- XVNGEPFGKAOTSF-UHFFFAOYSA-N c(cc1)ccc1N(c1cc2ccccc2cc1)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c1cc(cccc2)c2cc1 Chemical compound c(cc1)ccc1N(c1cc2ccccc2cc1)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c1cc(cccc2)c2cc1 XVNGEPFGKAOTSF-UHFFFAOYSA-N 0.000 description 1
- VHTUUGBNJKLUNJ-UHFFFAOYSA-N c(cc1)ccc1N(c1cccc2c1cccc2)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c1c(cccc2)c2ccc1 Chemical compound c(cc1)ccc1N(c1cccc2c1cccc2)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c1c(cccc2)c2ccc1 VHTUUGBNJKLUNJ-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
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Abstract
Description
最近、ディスプレイの大型化に伴い空間占有の少ない平面ディスプレイの要求が増大している。かかる平面ディスプレイの一つに、有機発光ダイオード(organic light emitting diode: OLED)とも呼ばれる有機電界発光デバイスがあるが、その技術は著しく発展しつつあり、既に様々な製品が発表されている。
有機電界発光デバイスは、プラスチックのようなフレキシブルな透明基板上にもデバイスを形成できるだけでなく、プラズマディスプレイパネルや無機電界発光(EL)ディスプレイに比べて低電圧(10V以下)で駆動可能である。
従来の青色発光物質は、発光時に長波長の光が現れ、色純度と発光効率が落ちるだけでなく、ドーピング濃度が高いほど色純度と発光効率がより低下するという問題があった。
本発明は上記のような問題を解決するためのもので、青色の色純度と発光効率に優れた有機電界発光デバイスを提供することが目的である。
化学式1
化学式2
B1 - X - B2
ここで、前記Xはナフタリン(naphthalene),アントラセン(anthracene), フェナントレン(phenanthrene), ピレン(pyrene), ペリレン(perylene)、及びキノリン(quinoline)のグループから選択される何れかであり、前記B1, B2のうち少なくとも一方はアリル(aryl), アルキルアリル(alkylaryl), アルコキシアリル(alkoxyaryl),アリルアミノアリル(arylaminoaryl), アルキルアミノアリル(alkylaminoaryl), 及びアリルアリル(arylallyl) グループから選択される。
本発明は基板上に形成される第1、第2電極の間に発光層が形成され、発光層は複数の物質で形成され、下記の化学式1をドーパントに使用する青色発光物質からなる。
化学式1
化学式2
B1 - X - B2
ここで、Xはナフタリン(naphthalene), アントラセン(anthracene), フェナントレン(phenanthrene), ピレン(pyrene), ペリレン(perylene), 及びキノリン(quinoline)のグループから選択される何れかであり、前記B1, B2のうち少なくとも一方は、アリル(aryl),アルキルアリル(alkylaryl), アルコキシアリル(alkoxyaryl), アリルアミノアリル(arylaminoaryl), アルキルアミノアリル(alkylaminoaryl), 及びアリルアリル(arylallyl) などのグループから選択できる。
特に、A1, A2のうち少なくとも一方は置換された、或いは未置換のフェニル(phenyl), バイフェニル(biphenyl), ピリジル(pyridyl), ナフチル(naphthyl), キノリル(quinolyl), イソキノリル(isoquinolyl), フルオレニル(fluorenyl), テルフェニル(terphenyl),メチル(methyl), エチル(ethyl), プロピル(propyl), イソプロピル(i-propyl), t-ブチル(t-buthyl)から選択できる。
例えば、A1, A2の置換基は、メチル(methyl), エチル(ethyl), プロピル(propyl), イソプロピル(i-propyl), t-ブチル(t-butyl), シクロヘキシル(cyclohexyl), メトキシ(methoxy), エトキシ(ethoxy), プロポキシ(propoxy), ブトキシ(butoxy), ジメチルアミノ(dimethylamino), トリメチルシリル(trimethylsilyl), フッ素, 塩素, フェノキシ(phenoxy), トリルオキシ(tolyloxy), ジメチルアミノ(dimethylamino), ジエチルアミノ(diethylamino), ジフェニルアミノ(diphenylamino), トリフェニルシリル(triphenylsilyl)から選択できる。
(1) 1,6-Dibromopyreneの合成
次いで、底の丸いフラスコに設置されたドロッピングファンネル(dropping funnel)に Br2(17.38g, 0.108mol)とCCl4(50mL)を入れた後、これを底の丸いフラスコで4時間ゆっくり滴下させる。そして、その溶液にN2を注入し、発生するHBrを除去する。
このようなドロッピング過程が終わると、約1時間その溶液をN2気流下で攪拌させた後、生成された沈殿物をフィルタリングする。
そして、沈殿物をトルエンを使用して再結晶させると、1,6-ダイブロモピレン(1,6-Dibromopyrene)の緑色の固体(6.05g, 34%)と、1,8-ダイブロモピレン(1,8-Dibromopyrene)(5g, 28%)の白色の固体とが得られる。
そして、反応終結時に2首の底の丸いフラスコを常温で冷却し、反応溶媒のトルエン40mLを減圧蒸留して除去する。
そして、反応終結時に、水とダイエチルエテル(diethylether)を使用して結果物を抽出し、MgSO4を使用して結果物から水を除去する。
そして、反応終結時に、底の丸いフラスコを冷却し、反応溶液のトルエンを除去する。
そして、反応終結時に、底の丸いフラスコを冷却し、反応溶媒のトルエンを除去した後、水とメチレンクロライドを使用して結果物を抽出する。
この固体でトルエンを約50%程度除去した後、メタノール(70mL)を添加してフィルタリングする。
ITO基板(glass)の発光面積が3mm×3mmの大きさとなるようにパタニングした後洗浄した。
次に、基板を真空チャンバーに装着した後、基本圧力が1×10-6torrとなるようにした後に、有機物をITO上にCuPC(200Å), NPB(500Å), 発光層(300Å), Alq3(200Å), LiF(5Å), Al(1000Å)の順序で成膜した。
この際、発光層の第1HOSTとして下記式の物質を使用し、ホストと不純物との混合比を1:0.01にした。
前記S-26の化学式を有するドーパントを使用して約1mAの電流を流した時、輝度は約3.2cd/Aを得、この際、CIE (Commision Internationale de L'Eclairage)はx=0.146, y=0.205であった。
前記S-28の化学式を有するドーパントを使用して約1mAの電流を流した時、輝度は約3.4cd/Aを得、この際、CIEはx=0.15, y=0.196であった。
ITO基板の発光面積が3mm×3mmの大きさとなるようにパタニングした後、洗浄した。
基板を真空チャンバーに装着した後、基本圧力が1×10-6torrとなるようにした後に、有機物をITO上にCuPC(200Å), NPB(300Å), 発光層(host-1:200Å), Alq3(400Å), LiF(5Å), Al(1000Å)の順序で成膜した。この際、約1mAの電流を流した時、輝度は約1.8cd/Aを現し、CIEはx=0.194, y=0.297を現した。
Claims (10)
- 前記化学式1の物質のwt. %は前記発光層の総重量のうち0.1 - 49.9 wt. %である請求項1記載の有機電界発光デバイス。
- 前記化学式1の物質と共に発光層を形成する物質は、下記化学式2の構造からなる請求項1記載の有機電界発光デバイス。
化学式2
B1 - X - B2
ここで、前記Xはナフタリン(naphthalene),アントラセン(anthracene), フェナントレン(phenanthrene), ピレン(pyrene), ペリレン(perylene)、及びキノリン(quinoline)のグループから選択される何れかであり、前記B1, B2のうち少なくとも一方はアリル(aryl), アルキルアリル(alkylaryl), アルコキシアリル(alkoxyaryl),アリルアミノアリル(arylaminoaryl), 及びアルキルアミノアリル(alkylaminoaryl)のグループから選択される。 - 前記B1, B2のうち何れか一方は、フェニル(phenyl),バイフェニル(biphenyl), ピリジル(pyridyl), ナフチル(naphthyl), トリチルフェニル(tritylphenyl), バイフェニルレニル(biphenylenyl), アントリル(anthryl), フェナントリル(phenanthryl), ピレニル(pyrenyl), ペリレニル(perylenyl), キノリル(quinolyl), イソキノリル(isoquinolyl), フルオレニル(fluorenyl), テルフェニル(terphenyl), トリル(tolyl), ザイリル(xylyl), メチルナフチル (methylnaphthyl), 及び水素の中から選択される請求項3記載の有機電界発光デバイス。
- 前記A1, A2のうち少なくとも一方は、置換された、或いは未置換のフェニル(phenyl), バイフェニル(biphenyl), ピリジル(pyridyl), ナフチル(naphthyl), キノリル(quinolyl), イソキノリル(isoquinolyl), フルオレニル(fluorenyl), テルフェニル(terphenyl), メチル(methyl), エチル(ethyl), プロピル(propyl), イソプロピル(i-propyl), t-ブチル(t-buthyl)から選択される請求項1記載の有機電界発光デバイス。
- 前記置換されたA1, A2のそれぞれの置換基は、少なくとも一つ以上であり、アルキル(alkyl), アルコキシ(alkoxy), アルキルアミノ(alkylamino), アルキルシリル(alkylsilyl), ハロゲン(halogen), アリル(aryl), アリルオキシ(aryloxy), アリルアミノ(arylamino), アリルシリル(arylsilyl)基、及び水素の中から選択される請求項1記載の有機電界発光デバイス。
- 前記置換基は、メチル(methyl), エチル(ethyl), プロピル(propyl), イソプロピル(i-propyl), t-ブチル(t-butyl), サイクロヘキシル(cyclohexyl), メトキシ(methoxy), エトキシ(ethoxy), プロポキシ(propoxy), ブトキシ(butoxy), ジメチルアミノ(dimethylamino), トリメチルシリル(trimethylsilyl), フッ素, 塩素, フェノキシ(phenoxy), トリルオキシ(tolyloxy), ジメチルアミノ(dimethylamino), ジエチルアミノ(diethylamino), ジフェニルアミノ(diphenylamino), トリフェニルシリル(triphenylsilyl)から選択される何れかである請求項7記載の有機電界発光デバイス。
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Publication number | Publication date |
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JP4778384B2 (ja) | 2011-09-21 |
US20100155714A1 (en) | 2010-06-24 |
US20040137270A1 (en) | 2004-07-15 |
JP3926791B2 (ja) | 2007-06-06 |
CN1535089A (zh) | 2004-10-06 |
EP1437395B2 (en) | 2015-08-26 |
EP1437395A2 (en) | 2004-07-14 |
US7700201B2 (en) | 2010-04-20 |
EP1437395B1 (en) | 2011-12-14 |
EP1437395A3 (en) | 2005-08-31 |
CN100481574C (zh) | 2009-04-22 |
JP2007027779A (ja) | 2007-02-01 |
US8436344B2 (en) | 2013-05-07 |
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