JP6552802B2 - 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP6552802B2 JP6552802B2 JP2014214447A JP2014214447A JP6552802B2 JP 6552802 B2 JP6552802 B2 JP 6552802B2 JP 2014214447 A JP2014214447 A JP 2014214447A JP 2014214447 A JP2014214447 A JP 2014214447A JP 6552802 B2 JP6552802 B2 JP 6552802B2
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- 239000000463 material Substances 0.000 title claims description 72
- 238000005401 electroluminescence Methods 0.000 title claims description 30
- -1 silylene group Chemical group 0.000 claims description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004431 deuterium atom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 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 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
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- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
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- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
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- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- GQCUGWCIKIYVOY-UHFFFAOYSA-M lithium;quinoline-8-carboxylate Chemical compound [Li+].C1=CN=C2C(C(=O)[O-])=CC=CC2=C1 GQCUGWCIKIYVOY-UHFFFAOYSA-M 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 239000008096 xylene 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
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Description
式(1)中、Xは酸素原子、硫黄原子、CR12R13、SiR14R15又はNR16であり、R1〜R16は置換若しくは無置換の環形成炭素数6以上30以下のアリール基、置換若しくは無置換の環形成炭素数1以上30以下のヘテロアリール基、炭素数1以上15以下のアルキル基、シリル基、ハロゲン原子、水素原子又は重水素原子であり、Lは単結合、置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基及び置換若しくは無置換の環形成炭素数1以上30以下のヘテロアリーレン基又はシリレン基であり、Arは置換若しくは無置換の環形成炭素数6以上30以下のアリール基、置換若しくは無置換の環形成炭素数1以上30以下のヘテロアリール基である。
本発明に係る有機エレクトロルミネッセンス素子用材料を用いた有機エレクトロルミネッセンス素子について説明する。図1は、本発明の一実施形態に係る有機エレクトロルミネッセンス素子100を示す模式図である。有機エレクトロルミネッセンス素子100は、例えば、基板102、陽極104、正孔注入層106、正孔輸送層108、発光層110、電子輸送層112、電子注入層114及び陰極116を備える。一実施形態において、本発明に係る有機エレクトロルミネッセンス素子用材料は、有機エレクトロルミネッセンス素子の発光層と陽極との間に配置された積層膜の何れか一層に用いることができる。
上述した本発明に係る有機エレクトロルミネッセンス素子用材料は、例えば、以下のように合成することができる。例えば、実施例化合物7を以下の反応により合成することができる。まず、中間体として、化合物Aを以下のように合成した。
Claims (5)
- 下記一般式(1)で表されることを特徴とする有機エレクトロルミネッセンス素子用材料。
[式(1)中、Xは酸素原子、硫黄原子、CR12R13、SiR14R15又はNR16であり、R1〜R16は置換若しくは無置換の環形成炭素数6以上30以下のアリール基、置換若しくは無置換の環形成炭素数1以上30以下のヘテロアリール基、炭素数1以上15以下のアルキル基、シリル基、ハロゲン原子、水素原子又は重水素原子であり、Lは単結合、置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基及び置換若しくは無置換の環形成炭素数1以上30以下のヘテロアリーレン基又はシリレン基であり、Arは置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換のビフェニル基、置換若しくは無置換のターフェニル基、置換若しくは無置換のフェナントリル基、置換若しくは無置換のジベンゾチオフェニル基、置換若しくは無置換のピリジル基である。] - 前記式(1)中、R2がフェニル基であり、下記一般式(2)で表されることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子用材料。
- 前記式(1)中、R1及びR3が水素原子又は重水素原子であり、R2がフェニル基であり、R5がNとの単結合を形成し、下記一般式(3)で表されることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子用材料。
- 隣接した複数のR1〜R16は結合し、飽和若しくは不飽和の環を形成する請求項1乃至3の何れか一に記載の有機エレクトロルミネッセンス素子用材料。
- 請求項1乃至4の何れか一に記載の有機エレクトロルミネッセンス素子用材料を発光層と陽極との間に配置される積層膜の一つの膜中に含むことを特徴とする有機エレクトロルミネッセンス素子。
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JP2014214447A JP6552802B2 (ja) | 2014-10-21 | 2014-10-21 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
KR1020150076226A KR102363932B1 (ko) | 2014-10-21 | 2015-05-29 | 유기 일렉트로루미네센스 소자용 재료 및 이를 포함하는 유기 일렉트로루미네센스 소자 |
US14/857,706 US10586927B2 (en) | 2014-10-21 | 2015-09-17 | Organic electroluminescent material and organic electroluminescent device including the same |
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US11832513B2 (en) | 2017-11-23 | 2023-11-28 | Merck Patent Gmbh | Materials for electronic devices |
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JPWO2012090806A1 (ja) * | 2010-12-27 | 2014-06-05 | 東レ株式会社 | 発光素子材料および発光素子 |
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JP6570834B2 (ja) | 2011-12-12 | 2019-09-04 | メルク パテント ゲーエムベーハー | 電子素子のための化合物 |
KR101918953B1 (ko) * | 2012-03-06 | 2018-11-16 | 삼성디스플레이 주식회사 | 아민계 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 유기 발광 장치 |
JP2014049539A (ja) * | 2012-08-30 | 2014-03-17 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP6194645B2 (ja) | 2012-09-27 | 2017-09-13 | 東ソー株式会社 | アミン化合物及びその用途 |
KR20160045019A (ko) * | 2014-10-14 | 2016-04-26 | 주식회사 동진쎄미켐 | 신규한 화합물 및 이를 포함하는 유기발광소자 |
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