JP4522862B2 - キノキサリン誘導体、有機半導体素子および電界発光素子 - Google Patents
キノキサリン誘導体、有機半導体素子および電界発光素子 Download PDFInfo
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- JP4522862B2 JP4522862B2 JP2004551194A JP2004551194A JP4522862B2 JP 4522862 B2 JP4522862 B2 JP 4522862B2 JP 2004551194 A JP2004551194 A JP 2004551194A JP 2004551194 A JP2004551194 A JP 2004551194A JP 4522862 B2 JP4522862 B2 JP 4522862B2
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- Prior art keywords
- quinoxaline derivative
- electroluminescent
- ring
- layer
- benzene ring
- 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.)
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- 239000004065 semiconductor Substances 0.000 title claims description 15
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims description 11
- 239000000463 material Substances 0.000 claims description 126
- 239000000126 substance Substances 0.000 claims description 45
- 230000000903 blocking effect Effects 0.000 claims description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 150000003252 quinoxalines Chemical class 0.000 description 106
- 230000015572 biosynthetic process Effects 0.000 description 53
- 238000003786 synthesis reaction Methods 0.000 description 53
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 239000010408 film Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000004985 diamines Chemical class 0.000 description 23
- 125000005594 diketone group Chemical group 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 19
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 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 9
- 239000000758 substrate Substances 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- RYGCQYVLYYFUHJ-UHFFFAOYSA-N 2,3-bis(furan-2-yl)phenanthro[9,10-b]pyrazine Chemical compound C1=COC(C=2C(=NC3=C4C=CC=CC4=C4C=CC=CC4=C3N=2)C=2OC=CC=2)=C1 RYGCQYVLYYFUHJ-UHFFFAOYSA-N 0.000 description 7
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- 125000003545 alkoxy group Chemical group 0.000 description 5
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- 150000002894 organic compounds Chemical class 0.000 description 5
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- 230000000052 comparative effect Effects 0.000 description 4
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- DYHJTAONEPZTCO-UHFFFAOYSA-N 1,2-dihydrophenanthrene Chemical compound C1=CC=CC2=C(C=CCC3)C3=CC=C21 DYHJTAONEPZTCO-UHFFFAOYSA-N 0.000 description 3
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 3
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- 238000002425 crystallisation Methods 0.000 description 3
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- 238000001308 synthesis method Methods 0.000 description 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 2
- WMAXWOOEPJQXEB-UHFFFAOYSA-N 2-phenyl-5-(4-phenylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 WMAXWOOEPJQXEB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
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- 239000013078 crystal Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
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- 239000011368 organic material Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- DTZWGKCFKSJGPK-VOTSOKGWSA-N (e)-2-(2-methyl-6-(2-(1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4h-pyran-4-ylidene)malononitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 DTZWGKCFKSJGPK-VOTSOKGWSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- FZYKBLSPMPIYKD-UHFFFAOYSA-N 5-(4-phenylphenyl)-1h-1,2,4-triazole Chemical compound C1=NNC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 FZYKBLSPMPIYKD-UHFFFAOYSA-N 0.000 description 1
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- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 1
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Description
したがって、電子輸送性材料の中でも、良好なホールブロッキング性を有する上に膜質が良く、結晶化しにくいホールブロッキング性材料が望まれている。
(1)一般式[C−1]で表されるキノキサリン誘導体。
(2)一般式[C−2]で表されるキノキサリン誘導体。
(3)一般式[C−3]で表されるキノキサリン誘導体。
(4)一般式[C−4]で表されるキノキサリン誘導体。
(5)一般式[C−5]で表されるキノキサリン誘導体。
(6)(1)乃至(5)のいずれか一において、
一般式[C−6]で表される前記複素環残基を含むキノキサリン誘導体。
[C−7]で示した合成例について詳細に説明する。
化学式[C−8]に示すジケトンおよび化学式[C−9]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−10]に示す。
化学式[C−11]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−13]に示す。
化学式[C−14]に示すジケトンおよび化学式[C−15]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−16]に示す。
化学式[C−17]に示すジケトンおよび化学式[C−9]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−18]に示す。
化学式[C−19]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−20]に示す。
化学式[C−21]に示すジケトンおよび化学式[C−15]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−22]に示す。
化学式[C−23]に示すジケトンおよび化学式[C−9]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−24]に示す。
化学式[C−25]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−26]に示す。
化学式[C−27]に示すジケトンおよび化学式[C−15]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−28]に示す。
化学式[C−29]に示すジケトンおよび化学式[C−9]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−30]に示す。
化学式[C−31]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−32]に示す。
化学式[C−33]に示すジケトンおよび化学式[C−15]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−34]に示す。
化学式[C−35]に示すジケトンおよび化学式[C−9]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−36]に示す。
化学式[C−37]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−38]に示す。
化学式[C−39]に示すジケトンおよび化学式[C−40]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−41]に示す。
化学式[C−42]に示すジケトンおよび化学式[C−40]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−43]に示す。
化学式[C−44]に示すジケトンおよび化学式[C−40]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−45]に示す。
化学式[C−46]に示すジケトンおよび化学式[C−40]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−47]に示す。
化学式[C−48]に示すジケトンおよび化学式[C−12]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−49]に示す。
化学式[C−50]に示すジケトンおよび化学式[C−15]に示すジアミンを用いた以外は合成例1と同様にして反応を行った。得られたキノキサリン誘導体を化学式[C−51]に示す。
これに対して、実施例5で測定した素子構造とは異なり、キノキサリン誘導体からなる電子輸送層を有しない構造の電界発光素子(ITO/Cu−Pc(20nm)/α−NPD(30nm)/Alq3(30nm)/CaF(1nm)/Alの素子特性について測定した。その結果を図5〜8のプロット1に示す。図5における輝度−電流特性においては、プロット1に示すように電流密度が100mA/cm2の場合において、4000cd/m2程度の輝度が得られた。この結果は、実施例5における素子構造の場合と大差なかった。
さらに、実施例5で測定した素子構造において、電子輸送層に本発明のキノキサリン誘導体ではなく従来からブロッキング性の材料として用いられているバソキュプロイン(以下、BCPと示す)を用いて作製した電界発光素子(ITO/Cu−Pc(20nm)/α−NPD(30nm)/Alq3(30nm)/BCP(20nm)/CaF(1nm)/Alの素子特性について測定した。その結果を図5〜8のプロット2に示す。図5における輝度−電流特性においては、プロット2に示すように電流密度が100mA/cm2の場合において、4000cd/m2程度の輝度が得られた。この結果は、実施例5における素子構造の場合と大差なかった。
キノキサリン誘導体の薄膜の代わりにBCPの薄膜を成膜したこと以外は実施例6と同様にサンプルを作製した。その結果、図10Bに示すように時間の経過に伴いBCPの薄膜は結晶化した。
Claims (10)
- 下記一般式で表されるキノキサリン誘導体。
- 下記一般式で表されるキノキサリン誘導体を用いた有機半導体素子。
- 請求項2において、
前記キノキサリン誘導体を電子輸送性材料として用いたことを特徴とする有機半導体素子。 - 請求項2において、
前記キノキサリン誘導体をホールブロッキング性材料として用いたことを特徴とする有機半導体素子。 - 第1の電極と第2の電極の間に形成された電界発光層の一部に下記一般式で表されるキノキサリン誘導体を用いたことを特徴とする電界発光素子。
- 請求項5において、
前記キノキサリン誘導体を電子輸送性材料として用いたことを特徴とする電界発光素子。 - 請求項5において、
前記キノキサリン誘導体をホールブロッキング性材料として用いたことを特徴とする電界発光素子。 - 請求項5において、
前記キノキサリン誘導体を発光層のゲスト材料として用いたことを特徴とする電界発光素子。 - 下記一般式で表されるキノキサリン誘導体およびゲスト材料を含む発光層を有することを特徴とする電界発光素子。
- 請求項9において、
前記ゲスト材料は、燐光性物質であることを特徴とする電界発光素子。
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2006073992A (ja) * | 2004-05-20 | 2006-03-16 | Semiconductor Energy Lab Co Ltd | 発光素子および発光装置 |
JP2009298794A (ja) * | 2004-05-20 | 2009-12-24 | Semiconductor Energy Lab Co Ltd | 有機金属錯体、発光装置、照明器具、および電子機器 |
US8853680B2 (en) | 2011-03-30 | 2014-10-07 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
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WO2005054261A1 (ja) | 2003-12-02 | 2005-06-16 | Semiconductor Energy Laboratory Co., Ltd. | 有機金属錯体およびそれを用いた発光素子 |
JP4637651B2 (ja) * | 2004-06-03 | 2011-02-23 | 三井化学株式会社 | アミン化合物、および該アミン化合物を含有する有機電界発光素子 |
US7554260B2 (en) | 2004-07-09 | 2009-06-30 | Semiconductor Energy Laboratory Co., Ltd. | Display device provided with a conductive film connection between a wiring component and a metal electrode film |
WO2006059486A1 (ja) * | 2004-12-02 | 2006-06-08 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタ材料、有機薄膜トランジスタ、電界効果トランジスタ、スイッチング素子、有機半導体材料及び有機半導体膜 |
WO2006062144A1 (en) * | 2004-12-07 | 2006-06-15 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element and light-emittng device using the same |
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US20060214151A1 (en) * | 2005-03-24 | 2006-09-28 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and laser apparatus using the light-emitting element |
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Also Published As
Publication number | Publication date |
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WO2004043937A1 (ja) | 2004-05-27 |
JPWO2004043937A1 (ja) | 2006-03-09 |
JP5127872B2 (ja) | 2013-01-23 |
US7355340B2 (en) | 2008-04-08 |
US20050003232A1 (en) | 2005-01-06 |
JP2010168396A (ja) | 2010-08-05 |
AU2003275704A1 (en) | 2004-06-03 |
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