JP7182971B2 - 有機化合物、有機発光素子、表示装置、撮像装置、電子機器及び移動体 - Google Patents
有機化合物、有機発光素子、表示装置、撮像装置、電子機器及び移動体 Download PDFInfo
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- JP7182971B2 JP7182971B2 JP2018177521A JP2018177521A JP7182971B2 JP 7182971 B2 JP7182971 B2 JP 7182971B2 JP 2018177521 A JP2018177521 A JP 2018177521A JP 2018177521 A JP2018177521 A JP 2018177521A JP 7182971 B2 JP7182971 B2 JP 7182971B2
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Images
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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Description
(a)アセナフテンキノン誘導体(D1)
(b)ジベンジルケトン誘導体(D2)
(c)ナフタレン誘導体(D3)
(d)フルオランテン誘導体(D4)
ここで上記(a)乃至(d)に示される化合物に適宜置換基を設けることにより、式(1)中のR1乃至R22が所望の置換基である有機化合物を合成することができる。
(1)基本骨格自体の発光波長が色純度の高い赤色領域にある
(2)HOMOエネルギーが低く、化合物自体の化学安定性が高い
(3)非対称構造であるため結晶性が低い
本発明者らは、一般式(1)で表される有機化合物を発明するにあたり、基本骨格それ自体に注目した。基本骨格自体により生じる発光が長波長な赤色であることで、置換基を設けることによる色の調整を最小限に抑制することができる。縮環構造以外に置換基を設ける場合は、その置換位置や置換基の種類によって安定性を損ねる場合がある。一般式(1)で表される有機化合物は、基本骨格自体により生じる発光が長波長な発光なので、置換基による波長の調整は最小限となる。そのため、有機化合物自体の安定性が高いことにつながるからである。なお、本明細書においては、長波長な赤色であることを、色純度が高い赤色とも呼ぶ。
本発明者らは、所望の発光波長領域を有する材料を創出する際に、分子のHOMOエネルギーに着目した。発光波長領域が長波長であることは、すなわちバンドギャップが狭いことを意味する。バンドギャップを狭くするには、HOMOエネルギーを高くすることや、LUMOエネルギーを低くすることが必要である。ここで、HOMOエネルギーが高いとは真空準位に近いことを意味し、HOMOエネルギーが低いとは真空準位から遠いことを意味する。LUMOエネルギーに関しても同様である。
基本骨格自体の発光波長が赤色の有機化合物は、共役長が長い化合物である。共役長が長い化合物は、分子平面性が高い傾向があるため、分子間相互作用により結晶化しやすい。有機化合物が結晶化した場合、昇華性が低下する、濃度消光を招くなど、有機化合物単体としての性質が変化してしまうので好ましくない。
(4)R9及びR10の少なくともいずれかに置換基を有する
(5)基本骨格を覆うような置換基を有する
一般式(1)で表される有機化合物は、R9及びR10の少なくともいずれかに置換基を設けることで分子間の重なりを抑制することができる。分子間の重なりを抑制することで結晶性をさらに抑制できる。結晶性を抑制すれば、前述の通り、濃度消光の抑制や昇華性の向上につながる。
結晶化をさらに改善する手段として、本発明者らは、基本骨格を覆うような置換基を設けることを試みた。基本骨格を覆う置換基とは、分子同士のπ共役平面を遮蔽するような置換基と言い換えることができる。
有機発光素子は、基板の上に、陽極、有機化合物層、陰極を形成して設けられる。陰極の上には、保護層、カラーフィルタ等を設けてよい。カラーフィルタを設ける場合は、平坦化層を設けてよい。
本発明の一実施形態に係る有機発光素子は、表示装置や照明装置の構成部材として用いることができる。他にも、電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライト、白色光源にカラーフィルタを有する発光装置等の用途がある。
100mlのナスフラスコに、以下に示す試薬、溶媒を仕込んだ。
化合物E1:2.00g(7.66mmol)
化合物E2:1.97g(8.04mmol)
エタノール:40ml
次に、85%水酸化ナトリウム556mg(8.43mmol)をエタノール10mlに溶解させた溶液を室温で滴下した。滴下終了後、窒素気流下で40℃に加熱しこの温度(40℃)で4時間攪拌を行った。反応終了後、水を加え、ろ過し、これを水及びメタノールで分散洗浄を行うことにより、濃緑色の化合物E3を3.20g(収率:89%)得た。
100mlのナスフラスコに、以下に示す試薬、溶媒を仕込んだ。
化合物E3:3.00g(6.39mmol)
化合物E4:1.44g(7.67mmol)
亜硝酸イソアミル:1.02ml(7.67mmol)
トルエン:50ml
次に、反応溶液を、窒素気流下で105℃に加熱しこの温度(105℃)で2時間攪拌を行った。さらに、化合物E4を480mg(2.56mmol)、亜硝酸イソアミルを0.34ml(2.56mmol)を加え、2時間撹拌した。反応終了後、トルエンと水で抽出を行った後、濃縮し、これをシリカゲルカラムクロマトグラフィー(ヘプタン:トルエン=4:1)にて精製後、ヘプタン/エタノールで分散洗浄を行うことにより、黄色化合物E5を1.81g(収率:50%)得た。
100mlのナスフラスコに、以下に示す試薬、溶媒を仕込んだ。
化合物E5:1.00g(1.76mmol)
化合物E6:607mg(1.85mmol)
Pd(PPh3)4:61mg(0.053mmol)
炭酸セシウム:2.29g(7.04mmol)
トルエン:18ml
エタノール:9ml
水:9ml
次に、反応溶液を、窒素気流下で90℃に加熱しこの温度(90℃)で4時間攪拌を行った。反応終了後、トルエンと水で抽出を行った後、濃縮し、これをシリカゲルカラムクロマトグラフィー(ヘプタン:クロロホルム=4:1)にて精製後、ヘプタン/エタノールで分散洗浄を行うことにより、黄色の化合物E8を1.07g(収率:88%)得た。
50mlのナスフラスコに、以下に示す試薬、溶媒を仕込んだ。
化合物E7:1.00g(1.45mmol)
Pd(dba)2:173mg(0.44mmol)
P(Cy)3(トリシクロヘキシルフォスフィン):252mg(0.90mmol)
DBU(ジアザビシクロウンデセン):0.87ml(5.80mmol)
DMAc:25ml
次に、反応溶液を、窒素気流下で170℃に加熱しこの温度(170℃)で5時間攪拌を行った。反応終了後、メタノールを加えて結晶を析出させた後に結晶をろ別し、水、メタノール、エタノール、ヘプタンで順次分散洗浄を行った。次に、得られた黄色結晶をシリカゲルカラムクロマトグラフィー(ヘプタン:クロロホルム=4:1)にて精製後、ヘプタン/エタノールで分散洗浄を行うことにより、黄色の化合物E8を947mg(収率:78%)得た。
20mlのナスフラスコに、以下に示す試薬、溶媒を仕込んだ。
化合物E8:300mg(0.460mmol)
t-BuOK:2.06g(18.4mmol)
DBU(ジアザビシクロウンデセン):5.50ml(36.8mmol)
ジエチレングリコールジメチルエーテル:18ml
次に、反応溶液を、窒素気流下で180℃に加熱しこの温度(180℃)で10時間攪拌を行った。反応終了後、水を加えて結晶を析出させた後に結晶をろ別し、水、メタノール、エタノール、ヘプタンで順次分散洗浄を行った。次に、得られた濃紫色固体を130℃のクロロベンゼンに溶解させ、そこにアルミナを加え加熱吸着処理を行った。これを熱時ろ過、濃縮を行い、アセトン/ヘプタンで分散洗浄を行うことにより、濃紫色の例示化合物A2を251mg(収率:84%)得た。
実測値:m/z=651 計算値:C52H26=651
以下の表6に示す例示化合物について、実施例1の原料E1、E2、E7を原料1、原料2、原料3に変えた他は実施例1と同様にして例示化合物を合成した。また、実施例1と同様にして測定した質量分析結果の実測値:m/zを示す。
本実施例では、表7に示す構成として、基板上に、陽極、正孔注入層(HIL)、正孔輸送層(HTL)、電子ブロッキング層(EBL)、発光層(EML)、正孔ブロッキング層(HBL)、電子輸送層(ETL)、電子注入層(EIL)、陰極が順次形成されたボトムエミッション型構造の有機EL素子を作製した。
ホスト:ゲスト=99.7:0.3
である。
実施例17において、表8に示される化合物に適宜変更する以外は、実施例17と同様の方法により有機発光素子を作製した。得られた素子について実施例17と同様に素子の特性を測定・評価した。測定の結果を表8に示す。
本実施例では、表9に示す構成として、基板上に陽極、正孔注入層(HIL)、正孔輸送層(HTL)、電子ブロッキング層(EBL)、第一発光層(1st EML)、第二発光層(2nd EML)、正孔ブロッキング層(HBL)、電子輸送層(ETL)、電子注入層(EIL)、陰極が順次形成されたトップエミッション型構造の有機EL素子を作製した。
第一ホスト:第一ゲスト:第三ゲスト=96.7:0.3:3.0
である。
第二ホスト:第二ゲスト=99.4:0.6
である。
Ag:Mg=1:1
である。
実施例において、表10に示される化合物に適宜変更する以外は、実施例29と同様の方法により有機発光素子を作製した。得られた素子について実施例29と同様に素子の特性を測定・評価した。測定の結果を表10に示す。
11 基板
12 防湿膜
13 ゲート電極
14 ゲート絶縁膜
15 半導体層
16 ドレイン電極
17 ソース電極
18 TFT
19 絶縁膜
20 コンタクトホール
21 陽極
22 有機化合物層
23 陰極
24 第一保護層
25 第二保護層
1000 表示装置
1001 上部カバー
1002 フレキシブルプリント回路
1003 タッチパネル
1004 フレキシブルプリント回路
1005 表示パネル
1006 フレーム
1007 回路基板
1008 バッテリー
1009 下部カバー
1100 撮像装置
1101 ビューファインダ
1102 背面ディスプレイ
1103 操作部
1104 筐体
1200 携帯機器
1201 表示部
1202 操作部
1203 筐体
1300 表示装置
1301 額縁
1302 表示部
1303 土台
1310 表示装置
1311 第一表示部
1312 第二表示部
1313 筐体
1314 屈曲点
1500 自動車
1501 テールランプ
1502 窓
1503 車体
Claims (18)
- 一般式(1)におけるR 9 及びR 10 の少なくとも1つが、水素原子以外の置換基であることを特徴とする請求項1に記載の有機化合物。
- 一般式(1)におけるR9及びR10の少なくとも1つが、前記アリール基であることを特徴とする請求項2に記載の有機化合物。
- 前記アリール基がフェニル基またはナフチル基であることを特徴とする請求項3に記載の有機化合物。
- 前記アリール基がフェニル基であり、前記フェニル基はオルト位に置換基を有することを特徴とする請求項4に記載の有機化合物。
- 前記フェニル基のオルト位に設けられた前記置換基は、ハロゲン原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、シアノ基のいずれかであることを特徴とする請求項5に記載の有機化合物。
- 前記フェニル基のオルト位に設けられた前記置換基が、ハロゲン原子、炭素原子数1乃至10のアルキル基、炭素原子数6乃至18のアリール基のいずれかであることを特徴とする請求項5または6に記載の有機化合物。
- 前記フェニル基のオルト位に設けられた前記置換基が、フッ素原子、メチル基、イソプロピル基、ターシャリブチル基、フェニル基のいずれかであることを特徴とする請求項5乃至7のいずれか一項に記載の有機化合物。
- 陽極と陰極と、
前記陽極と前記陰極との間に配置されている有機化合物層と、を有する有機発光素子であって、
前記有機化合物層は、請求項1乃至8のいずれか一項に記載の有機化合物を有することを特徴とする有機発光素子。 - 前記有機化合物層の少なくとも一層が、発光層であることを特徴とする請求項9に記載の有機発光素子。
- 前記発光層とは別の発光層をさらに有し、前記別の発光層は前記発光層が発する発光色とは異なる色を発光することを特徴とする請求項9または10に記載の有機発光素子。
- 白色発光することを特徴とする請求項9乃至11のいずれか一項に記載の有機発光素子。
- 複数の画素を有し、前記複数の画素の少なくとも一つが、請求項9乃至12のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続されたトランジスタと、を有することを特徴とする表示装置。
- 前記画素の光出射側に、RGBがデルタ配列されたカラーフィルタを有することを特徴とする請求項13に記載の表示装置。
- 複数のレンズを有する光学部と、前記光学部を通過した光を受光する撮像素子と、画像を表示する表示部と、を有し、
前記表示部は、前記撮像素子が撮像した画像を表示する表示部であり、前記表示部は請求項9乃至12のいずれか一項に記載の有機発光素子を有することを特徴とする撮像装置。 - 請求項9乃至12のいずれか一項に記載の有機発光素子を有する表示部と、前記表示部が設けられた筐体と、前記筐体に設けられ、外部と通信する通信部と、を有することを特徴とする電子機器。
- 請求項9乃至12のいずれか一項に記載の有機発光素子を有する光源と、前記光源が発した光を拡散させる光拡散部または前記光源が発した光を透過する光学フィルムと、を有することを特徴とする照明装置。
- 機体と、前記機体に設けられている灯具を有した移動体であって、
前記移動体は、自動車、船舶、航空機、またはドローンであって、
前記灯具は、請求項9乃至12のいずれか一項に記載の有機発光素子を有することを特徴とする移動体。
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