JP6030302B2 - フェニルピリジン単位を含む化合物 - Google Patents
フェニルピリジン単位を含む化合物 Download PDFInfo
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- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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Description
R1は各々独立にC1〜C20脂肪族基、C3〜C20芳香族基又はC3〜C20脂環式基であり、
R2は各々独立にC1〜C20脂肪族基、C3〜C20芳香族基又はC3〜C20脂環式基であり、
aは各々独立に0〜4の範囲内の整数であり、
bは各々独立に0〜3の範囲内の整数であり、
Ar1は直接結合或いはヘテロアリール、アリール、アルキル又はシクロアルキルであり、
Ar2はヘテロアリール、アリール、アルキル又はシクロアルキルであり、
cは0、1又は2であり、
nは2〜4の範囲内の整数である。
本明細書中で使用する「芳香族基」という用語は、1以上の芳香族原子団を含む原子価1以上の原子配列をいう。1以上の芳香族原子団を含む原子価1以上の原子配列は、窒素、硫黄、セレン、ケイ素及び酸素のようなヘテロ原子を含んでいてもよく、或いは炭素及び水素のみから構成されていてもよい。本明細書中で使用する「芳香族基」という用語は、特に限定されないが、フェニル基、ピリジル基、フラニル基、チエニル基、ナフチル基、フェニレン基及びビフェニル基を包含する。上述の通り、芳香族基は1以上の芳香族原子団を含む。芳香族原子団は常に4n+2(式中、「n」は1以上の整数である。)の「非局在化」電子を有する環状構造であり、フェニル基(n=1)、チエニル基(n=1)、フラニル基(n=1)、ナフチル基(n=2)、アズレニル基(n=2)及びアントラセニル基(n=3)で例示される。芳香族基はまた、非芳香族成分を含んでいてもよい。例えば、ベンジル基はフェニル環(芳香族原子団)及びメチレン基(非芳香族成分)からなる芳香族基である。同様に、テトラヒドロナフチル基は芳香族原子団(C6H3)が非芳香族成分−(CH2)4−に縮合してなる芳香族基である。便宜上、本明細書中での「芳香族基」という用語は、アルキル基、アルケニル基、アルキニル基、ハロアルキル基、ハロ芳香族基、共役ジエニル基、アルコール基、エーテル基、アルデヒド基、ケトン基、カルボン酸基、アシル基(例えば、エステルやアミドのようなカルボン酸誘導体)、アミン基、ニトロ基などの広範囲の官能基を有する芳香族基を包含するものと定義される。例えば、4−メチルフェニル基はメチル基を含むC7芳香族基であり、メチル基がアルキル基である官能基である。同様に、2−ニトロフェニル基はニトロ基を含むC6芳香族基であり、ニトロ基が官能基である。芳香族基は、4−トリフルオロメチルフェニル、ヘキサフルオロイソプロピリデンビス(4−フェン−1−イルオキシ)(即ち、−OPhC(CF3)2PhO−)、4−クロロメチルフェン−1−イル、3−トリフルオロビニル−2−チエニル、3−トリクロロメチルフェン−1−イル(即ち、3−CCl3Ph−)、4−(3−ブロモプロプ−1−イル)フェン−1−イル(即ち、4−BrCH2CH2CH2Ph−)などのハロゲン化芳香族基を包含する。芳香族基のさらに他の例には、4−アリルオキシフェン−1−オキシ、4−アミノフェン−1−イル(即ち、4−H2NPh−)、3−アミノカルボニルフェン−1−イル(即ち、NH2COPh−)、4−ベンゾイルフェン−1−イル、ジシアノメチリデンビス(4−フェン−1−イルオキシ)(即ち、−OPhC(CN)2PhO−)、3−メチルフェン−1−イル、メチレンビス(4−フェン−1−イルオキシ)(即ち、−OPhCH2PhO−)、2−エチルフェン−1−イル、フェニルエテニル、3−ホルミル−2−チエニル、2−ヘキシル−5−フラニル、ヘキサメチレン−1,6−ビス(4−フェン−1−イルオキシ)(即ち、−OPh(CH2)6PhO−)、4−ヒドロキシメチルフェン−1−イル(即ち、4−HOCH2Ph−)、4−メルカプトメチルフェン−1−イル(即ち、4−HSCH2Ph−)、4−メチルチオフェン−1−イル(即ち、4−CH3SPh−)、3−メトキシフェン−1−イル、2−メトキシカルボニルフェン−1−イルオキシ(例えば、メチルサリチル)、2−ニトロメチルフェン−1−イル(即ち、2−NO2CH2Ph)、3−トリメチルシリルフェン−1−イル、4−t−ブチルジメチルシリルフェン−1−イル、4−ビニルフェン−1−イル、ビニリデンビス(フェニル)などがある。「C3〜C10芳香族基」という用語は、3以上で10以下の炭素原子を含む芳香族基を包含する。芳香族基1−イミダゾリル(C3H2N2−)はC3芳香族基を代表する。ベンジル基(C7H7−)はC7芳香族基を代表する。
凝縮器、窒素入口及びゴム隔壁を備えた火炎乾燥三つ口丸底フラスコに、化合物25(2.70g、5.00mmol)、ピナコレートジボラン(3.81g、15.0mmol)、乾燥KOAc(1.47g、15.0mmol)及びシクロヘキシルホスフィンリガンド(103mg、0.250mmol)を添加した。次いで、フラスコを大気から防護した状態に置き、無水THF(20mL)及びジオキサン(5mL)を仕込み、撹拌溶液を通してN2をパージすることで溶液を脱気した。15分後、反応混合物にPd(OAc)2(23.0mg、0.100mmol)を仕込み、混合物を12時間還流加熱した。この時間が経過した後、反応混合物を室温(RT)に冷却し、セライトで濾過した。濾過ケークをEtOAcで洗浄し、濾液を濃縮乾固した。残留物を、EtOAc溶離剤を用いてSiO2でクロマトグラフィー処理した。収量は2.65g、90%であった。1H NMR(400MHz,CD2Cl2,25℃)δ 1.39(s,12H)、7.41(m,2H)、7.52(t,1H)、7.63(m,4H)、7.82(m,4H)、7.92(s,3H);7.96(m,2H)、8.00(m,2H)、8.13(s,1H)、8.60(m,2H)、8.94(d,2H)。ピナコールホウ酸エステルは、希H2SO4及びMeOHの混合物中でエステルを加熱することで対応ボロン酸に転化できる。酸をNaHCO3で中和した後、濃縮乾固して得られる固体をH2O中に懸濁し、濾過し、H2Oで洗浄し、乾燥する。
凝縮器、栓及び窒素入口を備えた三つ口丸底フラスコ内において、H2O(50mL)及びジオキサン(50mL)のパージした混合物に、Na2CO3(10.6g、100mmol)、1,3,5−(3−ブロモフェニル)ベンゼン(10.9g、20.0mmol)及び3−ピリジルボロン酸(5.41g、44.0mmol)を添加した。N2で15分間パージした後、Pd(PPh3)4(0.924g、0.800mmol)を添加し、混合物を穏やかな還流下で24時間加熱した。反応混合物を室温(RT)に冷却し、CH2Cl2(100mL)で希釈し、飽和NaHCO3を含む分液漏斗に移し、反応フラスコをCH2Cl2及びH2Oですすいだ。有機層を除去し、水層をCH2Cl2(100mL)で抽出し、Na2SO4上で乾燥し、濃縮乾固して泡状物を得た。粗生成物をSiO2によるクロマトグラフィーにかけ、EtOAcで溶出することで精製した。SiO2上での分離後に2種の生成物を集めた。収量は、化合物25が4.55g、42%であり、化合物35が2.41g、22%であった。1H NMR−化合物25(400MHz,CD2Cl2,25℃)δ 7.40(m,3H)、7.55(m,1H)、7.65(m,5H)、7.78(m,2H)、7.88(d,2H)、7.94(m,4H)、7.98(m,2H)、8.60(dd,2H)、8.93(d,2H);1H NMR−化合物35(400MHz,CD2Cl2,25℃)δ 7.40(m,3H)、7.55(m,2H)、7.65(m,4H)、7.77(m,2H)、7.89(m,5H)、7.99(m,1H)、8.61(dd,1H)、8.93(d,1H)。
Na2CO3(4.24g)を含むTHF(20mL)/H2O(20mL)の溶液を窒素でパージした。この溶液に、ボロン酸エステル化合物29(2.60g、4.43mmol)、3,5−ジブロモピリジン(473mg、2.00mmol)、次いでPd(PPh3)4(204mg、0.177mmol)を添加した。反応物を窒素の不活性雰囲気下に置き、12時間還流加熱した。混合物をRTに冷却し、層を分離した。有機層をNaHCO3(1×100mL)で洗浄し、Na2SO4上で乾燥し、濃縮乾固した。濾過ケークを5%MeOH/CH2Cl2で洗浄し、濾液を濃縮乾固して泡状物を得た。粗物質をSiO2でクロマトグラフィー処理し、5%MeOH/CH2Cl2で溶出することで、生成物を白色泡状物として得た。収量は1.56g、78%であった。1H NMR(400MHz,CD2Cl2,25℃)δ 7.39(m,4H)、7.64(m,10H)、7.76(m,8H)、7.98(m,14H)、8.04(t,2H)、8.25(t,1H)、8.58(m,4H)、8.93(m,6H)。
Claims (1)
- 次式の化合物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US12/125,296 | 2008-05-22 | ||
US12/125,296 US8062768B2 (en) | 2008-05-22 | 2008-05-22 | Compound comprising phenyl pyridine units |
US12/258,880 US8039125B2 (en) | 2008-05-22 | 2008-10-27 | Compound comprising phenyl pyridine units |
US12/258,880 | 2008-10-27 | ||
PCT/US2009/041525 WO2009142870A1 (en) | 2008-05-22 | 2009-04-23 | Compound comprising phenyl pyridine units |
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JP2011523644A JP2011523644A (ja) | 2011-08-18 |
JP6030302B2 true JP6030302B2 (ja) | 2016-11-24 |
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JP2011510539A Active JP6030302B2 (ja) | 2008-05-22 | 2009-04-23 | フェニルピリジン単位を含む化合物 |
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US (1) | US8039125B2 (ja) |
EP (1) | EP2307368B1 (ja) |
JP (1) | JP6030302B2 (ja) |
KR (2) | KR101704044B1 (ja) |
CN (1) | CN102036958B (ja) |
TW (1) | TWI475007B (ja) |
WO (1) | WO2009142870A1 (ja) |
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US8039125B2 (en) * | 2008-05-22 | 2011-10-18 | General Electric Company | Compound comprising phenyl pyridine units |
US8062768B2 (en) * | 2008-05-22 | 2011-11-22 | General Electric Company | Compound comprising phenyl pyridine units |
US7989476B2 (en) * | 2009-01-08 | 2011-08-02 | General Electric Company | Electron-transporting materials and processes for making the same |
US8691399B2 (en) | 2009-01-08 | 2014-04-08 | General Electric Company | Electron-transporting materials and processes for making the same |
US8178682B2 (en) * | 2009-06-26 | 2012-05-15 | General Electric Company | Process for making organic compounds and the organic compounds made therefrom |
KR101288566B1 (ko) | 2009-12-16 | 2013-07-22 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101508424B1 (ko) * | 2012-07-13 | 2015-04-07 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 |
JP6764671B2 (ja) * | 2015-04-14 | 2020-10-07 | 株式会社半導体エネルギー研究所 | 複素環化合物、発光素子、発光装置、電子機器、および照明装置 |
US20190153154A1 (en) * | 2015-08-20 | 2019-05-23 | Auckland Uniservices Limited | Polymers of intrinsic microporosity (pims) containing locked spirobisindane structures and methods of synthesis of pims polymers |
JP6563303B2 (ja) * | 2015-10-16 | 2019-08-21 | 株式会社東芝 | 光電変換素子及び撮像装置 |
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