JP6508700B2 - 縮合多環芳香族骨格を有するポリマー及びそれを用いた発光素子及び電極 - Google Patents
縮合多環芳香族骨格を有するポリマー及びそれを用いた発光素子及び電極 Download PDFInfo
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- JP6508700B2 JP6508700B2 JP2014219812A JP2014219812A JP6508700B2 JP 6508700 B2 JP6508700 B2 JP 6508700B2 JP 2014219812 A JP2014219812 A JP 2014219812A JP 2014219812 A JP2014219812 A JP 2014219812A JP 6508700 B2 JP6508700 B2 JP 6508700B2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Power Engineering (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Electroluminescent Light Sources (AREA)
Description
[1]本発明は、フルオレン単位と、下記式(1)、(2)、(3)、(4)、(5)及び(6)の何れかで表される単位とを含む、縮合多環芳香族骨格を有するポリマーを提供する。
[2]本発明は、下記式(7)で表される繰り返し単位を有し、該繰返し単位の数が1〜2000の交互共重合体であることを特徴とする前記[1]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[3]本発明は、R11、R12、R21、R22、R31、R32、R41、R42が、フッ素原子及び塩素原子の少なくとも何れかであることを特徴とする前記[1]又は[2]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[4]本発明は、a+b+c+d=3の整数であることを特徴とする前記[3]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[5]本発明は、R11、R12、R21、R22、R31、R32、R41、R42が、フッ素原子であることを特徴とする前記[3]又は[4]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[6]本発明は、R1、R2、R3、R4、R5、R6、R7、R8、R51、R52、R53、R54、R55、R56、R57、R58が、互いに独立して水素原子、メチル基、核置換基を有していてもよいアリール基であることを特徴とする前記[5]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[7]本発明は、R1、R2、R3、R4、R5、R6、R7、R8、R51、R52、R53、R54、R55、R56、R57、R58が、何れも水素原子であることを特徴とする前記[6]に記載の縮合多環芳香族骨格を有するポリマーを提供する。
[8]本発明は、前記[1]〜[7]の何れか一項に記載の縮合多環芳香族骨格を有するポリマーを発光層の発光材料として含む発光素子を提供する。
[9]本発明は、前記[1]〜[7]の何れか一項に記載の縮合多環芳香族骨格を有するポリマーを活物質層の電極活物質として含む電極を提供する。
[10]本発明は、二次電池、電気二重層又は電気化学キャパシタにおける1対の電極の一方として使用されることを特徴とする前記[9]に記載の電極を提供する。
上記式(7)で表される繰返し単位に含まれるフルオレン骨格を有し、本発明の共重合体のモノマー成分として使用する化合物としては、例えば、ジアルキルフルオレンのボロン酸エステルを使用することができる。フルオレン骨格に結合したアルキル基としては、例えばオクチル基やヘキシル基等の他に、上記式(7)におけるA1、A2と同じ官能基が挙げられる。下記に、一例としてジオクチルフルオレンのボロン酸エステルの化学構造を示すが、本発明の共重合体の合成においては、この化合物に限定されるものではない。
上記一般式(1)で表されるフェナントレン骨格を有し、本発明の共重合体のモノマー成分となる化合物は、例えば、図2に示す反応の模式図に従って合成することができる。図2には、反応経路1(実線で囲む部分)、反応経路2a(点線で囲む部分)及び反応経路2b(一点鎖線で囲む部分)の3つの反応経路を示している。
次に、上記一般式(3)、(4)、(5)及び(6)で表されるフェナントロリン骨格を有し、本発明の共重合体のモノマー成分となる少なくとも1つの化合物の例の合成方法を説明する。
次に、本発明の共重合体を用いて作製する有機発光素子について説明する。作製する有機発光素子は、陽極と陰極との間に一層若しくは多層の有機薄膜を積層した素子である。有機発光素子が一層の場合、陽極と陰極との間に発光層が設けられる。前記発光層は発光材料を含有し、さらに発光材料、陽極から注入した正孔若しくは陰極から注入した電子を発光材料まで輸送する目的で、正孔輸送材料又は電子輸送材料を含有する。ここで使用する発光素子は、発光性能に加えて、正孔輸送能及び電子輸送能の少なくとも何れかの性能を単一の材料で有する場合や、それぞれの特性を有する化合物の混合で使用する場合に有用である。本発明の共重合体は、発光材料として使用される。
(1−1)陽極/正孔輸送層/発光層/陰極
(1−2)陽極/発光層/電子輸送層/陰極
(1−3)陽極/正孔輸送層/発光層/電子輸送層/陰極
(1−4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(1−5)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(1−6)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
二次電池としては、平均作動電圧が4V程度と高く、エネルギー密度を高くすることができるリチウムイオン二次電池等の電極材料として使用が期待できる。リチウムイオン二次電池は、リチウムイオンを吸蔵、放出する炭素材料を負極とし、コバルト酸リチウム(LiCoO3)等のリチウム層状化合物を正極とし、電解液として六フッ化リン酸リチウム等のリチウム塩をエチレンカーボネートやプロピレンカーボネート等の有機溶媒に溶解させた液を使用している。正極材としては、LiCoO3の他にも、NiCo系、NiCoMn系、NiMn系等が検討されている。また、陰極材として、窒化物、合金系、究極の負極材であるリチウム金属等の様々な材料が提案されている。
電気二重層キャパシタは、活性炭等の分極性電極を正負電極とし、電極表面と電解液の界面に生じる電気二重層を静電容量として利用するものである。電気二重層キャパシタは、出力密度が高く、急速充放電が可能である。また、充放電に伴った電解質イオンが電解液内を移動して電極界面に吸脱着するだけであり、電池のように電気化学反応を伴わないため、充放電を繰り返しても容量変化が少ない。
電気化学キャパシタは、電解液として、第4級アンモニウム塩又は第4級ホスホニウム塩を溶質とした非水系電解液が使用される。この、電気化学キャパシタにおいて、本発明の共重合体は正極として使用し、負極として酸化還元反応特性を有するポリアセチレン、ポリアセン、ポリフェニレン、ポリフルオレン等の従来の導電性高分子を電極活物質とした電極を使用することができる。この構成の電気化学キャパシタは、本発明の共重合体が従来の導電性高分子と比べて容量が増加するだけでなく、p−ドーピングの酸化還元電位が高い状態で作動するため、作動電圧が高く、高容量で高エネルギー密度を有することができる。
例示化合物番号8−1の化合物及びそれをモノマーとして使用する共重合体の合成
まず、例示化合物番号8−1の化合物を得るために、その前駆体を合成した。
1H−NMR(CDCl3)δ[ppm]=7.60(m, 2H), 7.55 (brs, 2H), 7.26−7.25(m, 4H)
19F−NMR(CDCl3)δ[ppm]=−131.6(m, 2F), −110.5(t, J=4.8Hz, 4F)
1H−NMR(CDCl3)δ[ppm]=8.49(d, J=9.0Hz, 2H)8.42(d, J=2.0Hz, 2H)、7.91(dd, J=9.0, 2.0Hz, 2H)
19F−NMR(CDCl3)δ[ppm]=−128.9(m, 2F), −105.8(t, J=4.1Hz, 4F)
1H−NMR(CDCl3)δ[ppm]=8.93−7.40(12H), 2.25−1.83(4H),1.17−0.99(20H) 0.86−0.62(10H)
19F−NMR(CDCl3)δ[ppm]=−128.9(2F), −105.4(4F)
例示化合物番号9−1の化合物及びそれをモノマーとして使用する共重合体の合成
まず、例示化合物番号9−1の化合物を得るために、その前駆体を合成した。
1H−NMR(CDCl3)δ[ppm]=7.53(m, 4H), 7.22 (m, 4H)
19F−NMR(CDCl3)δ[ppm]=−131.6(m, 2F), −110.5(t, J=4.8Hz, 4F)
1H−NMR(CDCl3)δ[ppm]=8.71(d, J=1.8Hz, 2H)8.15(d, J=8.6Hz, 2H)、7.83(dd, J=8.6, 1.8Hz, 2H)
19F−NMR(CDCl3)δ[ppm]=−128.8(m, 2F), −105.6(t, J=4.0Hz, 4F)
1H−NMR(CDCl3)δ[ppm]=8.47−7.80(12H), 2.23−2.04(4H), 1.17−0.88(20H), 0.86−0.51(10H)
19F−NMR(CDCl3)δ[ppm]=−128.6(2F), −105.4(4F)
例示化合物番号10−1、11−1、12−1の化合物の合成
例示化合物番号10−1、11−1、12−1の化合物の合成を以下の手順で行った。
1H−NMR(CDCl3)δ[ppm]=8.74−7.71(10H), 2.34−2.20(4H), 1.19−0.81(20H), 0.77−0.57(10H)
19F−NMR(CDCl3)δ[ppm]=−128.4(2F), −104.8(4F)
Claims (10)
- フルオレン単位と、下記式(1)、(2)、(3)、(4)、(5)及び(6)の何れかで表される単位とを含む、縮合多環芳香族骨格を有するポリマー。
- R11、R12、R21、R22、R31、R32、R41、R42が、フッ素原子及び塩素原子の少なくとも何れかであることを特徴とする請求項1又は2に記載の縮合多環芳香族骨格を有するポリマー。
- a+b+c+d=3の整数であることを特徴とする請求項3に記載の縮合多環芳香族骨格を有するポリマー。
- R11、R12、R21、R22、R31、R32、R41、R42が、フッ素原子であることを特徴とする請求項3又は4に記載の縮合多環芳香族骨格を有するポリマー。
- R1、R2、R3、R4、R5、R6、R7、R8、R51、R52、R53、R54、R55、R56、R57、R58が、互いに独立して水素原子、メチル基、核置換基を有していてもよいアリール基であることを特徴とする請求項5に記載の縮合多環芳香族骨格を有するポリマー。
- R1、R2、R3、R4、R5、R6、R7、R8、R51、R52、R53、R54、R55、R56、R57、R58が、何れも水素原子であることを特徴とする請求項6に記載の縮合多環芳香族骨格を有するポリマー。
- 請求項1〜7の何れか一項に記載の縮合多環芳香族骨格を有するポリマーを発光層の発光材料として含む発光素子。
- 請求項1〜7の何れか一項に記載の縮合多環芳香族骨格を有するポリマーを活物質層の電極活物質として含む電極。
- 二次電池、電気二重層又は電気化学キャパシタにおける1対の電極の一方として使用されることを特徴とする請求項9に記載の電極。
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