JP2017525151A5 - - Google Patents

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JP2017525151A5
JP2017525151A5 JP2017502694A JP2017502694A JP2017525151A5 JP 2017525151 A5 JP2017525151 A5 JP 2017525151A5 JP 2017502694 A JP2017502694 A JP 2017502694A JP 2017502694 A JP2017502694 A JP 2017502694A JP 2017525151 A5 JP2017525151 A5 JP 2017525151A5
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lumo
homo
energy gap
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Priority claimed from PCT/US2014/062351 external-priority patent/WO2015061772A1/en
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アノードおよびカソードを含む、重なり関係にある二つの電極と、
当該二つの電極の間に配置され、ドナー−アクセプタヘテロ接合を形成する少なくとも一つのドナー材料および少なくとも一つのアクセプタ材料を含む光活性領域（ここで、前記少なくとも一つのアクセプタ材料は、最低空軌道エネルギー準位（ＬＵＭＯＡｃｃ）および最高被占軌道エネルギー準位（ＨＯＭＯＡｃｃ）を有する）と、
前記カソードと前記少なくとも一つのアクセプタ材料との間に配置される励起子阻止電子フィルタ（ここで、当該電子フィルタは、少なくとも一つのカソード側の広エネルギーギャップ材料および少なくとも一つの電子伝導材料を含む混合物を含む）と、
を含み、
前記少なくとも一つのカソード側の広エネルギーギャップ材料は、
・前記ＬＵＭＯＡｃｃ以下である最低空軌道エネルギー準位（ＬＵＭＯＣＳ−ＷＧ）と、
・前記ＨＯＭＯＡｃｃ以上である、または前記ＨＯＭＯＡｃｃより０．３ｅＶの範囲内で小さい最高被占軌道エネルギー準位（ＨＯＭＯＣＳ−ＷＧ）と、
・ＨＯＭＯＡｃｃ−ＬＵＭＯＡｃｃのエネルギーギャップより広いＨＯＭＯＣＳ−ＷＧ−ＬＵＭＯＣＳ−ＷＧのエネルギーギャップと、
・８５℃以上のガラス転移温度と、
を有し、
前記少なくとも一つの電子伝導材料は、前記ＬＵＭＯ Ａｃｃ 以上である、または前記ＬＵＭＯ Ａｃｃ より０．２ｅＶの範囲内で小さい最低空軌道エネルギー準位（ＬＵＭＯ ＥＣ ）を有する有機感光性光電子デバイス。 Two electrodes in an overlapping relationship, including an anode and a cathode;
A photoactive region disposed between the two electrodes and comprising at least one donor material and at least one acceptor material forming a donor-acceptor heterojunction, wherein the at least one acceptor material has a minimum free orbital energy and level (LUMO Acc) and highest occupied molecular orbital energy level that have a (HOMO Acc)),
An exciton blocking electronic filter disposed between the cathode and the at least one acceptor material, wherein the electronic filter comprises at least one cathode-side wide energy gap material and at least one electron conducting material Including)
Including
The at least one cathode side wide energy gap material comprises:
The lowest orbital energy level (LUMO CS-WG ) that is less than or equal to the LUMO Acc ;
A maximum occupied orbit energy level (HOMO CS-WG ) that is equal to or higher than the HOMO Acc or smaller than the HOMO Acc within a range of 0.3 eV;
-HOMO CS-WG - LUMO CS-WG energy gap wider than HOMO Acc -LUMO Acc energy gap ;
And the glass transition temperature · 85 ℃ or more,
I have a,
The at least one electron-conducting material, an organic photosensitive optoelectronic device having said at LUMO Acc or more, or less lowest unoccupied molecular orbital energy level in the range of 0.2eV than the LUMO Acc (LUMO EC). 前記少なくとも一つのカソード側の広エネルギーギャップ材料は、３，３’，５，５’−テトラ［（ｍ−ピリジル）−フェン−３−イル］ビフェニル（ＢＰ４ｍＰｙ）、２，２’，２”−（１，３，５−ベンジントリイル）−トリス（１−フェニル−１−Ｈ−ベンズイミダゾール）（ＴＰＢｉ）、ビス（２−メチル−８−キノリノレート）−４−（フェニルフェノラト）アルミニウム（ＢＡｌｑ）、トリス（８−ヒドロキシ−キノリナト）アルミニウム（Ａｌｑ３）、トリス（２，４，６−トリメチル−３−（ピリジン−３−イル）フェニル）ボラン（３ＴＰＹＭＢ）、４，４０−（１，３−フェニレン）ビス（２，６−ジ−トリルピリジン−３，５−ジカルボニトリル）（ｍ−ＭＰｙＣＮ）、４，４０−（１，３−フェニレン）ビス（２，６−ジ（ビフェニル−４−イル）ピリジン−３，５−ジカルボニトリル）（ｍ−ＰｈＰｙＣＮ）、４，４０−（１，３−フェニレン）ビス（２，６−ジフェニルピリジン−３，５−ジカルボニトリル）（ｍ−ＰｙＣＮ）、６，６０−（１，４−フェニレン）ビス（２−フェニル−４−ｐ−トリルニコチノニトリル）（ｐ−ＰＰｔＮＮ）、４，４０−（１，４−フェニレン）ビス（２−フェニル−６−ｐ−トリルニコチノニトリル）（ｐ−ＰＰｔＮＴ）、およびそれらの誘導体から選択される材料を含む請求項１に記載のデバイス。   The at least one cathode-side wide energy gap material is 3,3 ′, 5,5′-tetra [(m-pyridyl) -phen-3-yl] biphenyl (BP4mPy), 2,2 ′, 2 ″ — (1,3,5-Benzinetriyl) -tris (1-phenyl-1-H-benzimidazole) (TPBi), bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq ), Tris (8-hydroxy-quinolinato) aluminum (Alq3), tris (2,4,6-trimethyl-3- (pyridin-3-yl) phenyl) borane (3TPYMB), 4,40- (1,3- Phenylene) bis (2,6-di-tolylpyridine-3,5-dicarbonitrile) (m-MPyCN), 4,40- (1,3-phenylene) bis (2, -Di (biphenyl-4-yl) pyridine-3,5-dicarbonitrile) (m-PhPyCN), 4,40- (1,3-phenylene) bis (2,6-diphenylpyridine-3,5-di (Carbonitrile) (m-PyCN), 6,60- (1,4-phenylene) bis (2-phenyl-4-p-tolylnicotinonitrile) (p-PPtNN), 4,40- (1,4- The device of claim 1 comprising a material selected from phenylene) bis (2-phenyl-6-p-tolylnicotinonitrile) (p-PPtNT), and derivatives thereof. 前記広エネルギーギャップ材料は、８５〜２００℃の間のガラス転移温度を有する請求項１に記載のデバイス。   The device of claim 1, wherein the wide energy gap material has a glass transition temperature between 85-200 ° C. 前記広エネルギーギャップ材料は、１００〜１６５℃の間のガラス転移温度を有する請求項１に記載のデバイス。   The device of claim 1, wherein the wide energy gap material has a glass transition temperature between 100-165 ° C. 前記ＨＯＭＯＣＳ−ＷＧは、前記ＨＯＭＯＡｃｃより大きく、前記ＬＵＭＯＣＳ−ＷＧは、前記ＬＵＭＯＡｃｃより小さい請求項１に記載のデバイス。 The device according to claim 1, wherein the HOMO CS-WG is larger than the HOMO Acc , and the LUMO CS-WG is smaller than the LUMO Acc . 前記ＬＵＭＯＥＣは、前記ＬＵＭＯＡｃｃと等しい請求項１に記載のデバイス。 The device of claim 1, wherein the LUMO EC is equal to the LUMO Acc . 前記ＬＵＭＯＥＣは、前記ＬＵＭＯＡｃｃより大きい請求項１に記載のデバイス。 The device of claim 1, wherein the LUMO EC is greater than the LUMO Acc . 前記ＬＵＭＯＣＳ−ＷＧは、前記ＬＵＭＯＥＣより小さい請求項１に記載のデバイス。 The device of claim 1, wherein the LUMO CS-WG is smaller than the LUMO EC . 前記少なくとも一つのアクセプタ材料は、サブフタロシアニン、サブナフタロシアニン、ジピリン錯体、ＢＯＤＩＰＹ錯体、ペリレン、ナフタレン、フラーレン、官能基化フラーレン誘導体、およびそれらの誘導体から選択される材料を含む請求項１に記載のデバイス。   The said at least one acceptor material comprises a material selected from subphthalocyanine, subnaphthalocyanine, dipyrine complex, BODIPY complex, perylene, naphthalene, fullerene, functionalized fullerene derivatives, and derivatives thereof. device. 前記少なくとも一つのアクセプタ材料は、フラーレンおよび官能基化フラーレン誘導体から選択される材料を含む請求項９に記載のデバイス。 The device of claim 9, wherein the at least one acceptor material comprises a material selected from fullerenes and functionalized fullerene derivatives . 前記少なくとも一つの電子伝導材料は、サブフタロシアニン、サブナフタロシアニン、ジピリン錯体、ＢＯＤＩＰＹ錯体、ペリレン、ナフタレン、フラーレン、官能基化フラーレン誘導体、およびそれらの誘導体から選択される材料を含む請求項１に記載のデバイス。   The said at least one electron conducting material comprises a material selected from subphthalocyanine, subnaphthalocyanine, dipyrine complex, BODIPY complex, perylene, naphthalene, fullerene, functionalized fullerene derivatives, and derivatives thereof. Devices. 前記少なくとも一つのアクセプタ材料および前記少なくとも一つの電子伝導材料は、同一の材料を含む請求項１に記載のデバイス。   The device of claim 1, wherein the at least one acceptor material and the at least one electron conducting material comprise the same material. アノードおよびカソードを含む、重なり関係にある二つの電極と、
当該二つの電極の間に配置され、ドナー−アクセプタヘテロ接合を形成する少なくとも一つのドナー材料および少なくとも一つのアクセプタ材料を含む光活性領域（ここで、前記少なくとも一つのドナー材料は、最低空軌道エネルギー準位（ＬＵＭＯＤｏｎ）および最高被占軌道エネルギー準位（ＨＯＭＯＤｏｎ）を有する）と、
前記アノードと前記少なくとも一つのドナー材料との間に配置される励起子阻止正孔フィルタ（ここで、当該正孔フィルタは、少なくとも一つのアノード側の広エネルギーギャップ材料および少なくとも一つの正孔伝導材料を含む混合物を含む）と、
を含み、
前記少なくとも一つのアノード側の広エネルギーギャップ材料は、
・前記ＨＯＭＯＤｏｎ以上である最高被占軌道エネルギー準位（ＨＯＭＯＡＳ−ＷＧ）と、
・前記ＬＵＭＯＤｏｎ以下である、または前記ＬＵＭＯＤｏｎより０．３ｅＶの範囲内で大きい最低空軌道エネルギー準位（ＬＵＭＯＡＳ−ＷＧ）と、
・ＨＯＭＯＤｏｎ−ＬＵＭＯＤｏｎのエネルギーギャップより広いＨＯＭＯＡＳ−ＷＧ−ＬＵＭＯＡＳ−ＷＧのエネルギーギャップと、
・８５℃以上のガラス転移温度と、
を有する有機感光性光電子デバイス。 Two electrodes in an overlapping relationship, including an anode and a cathode;
At least one donor material disposed between the two electrodes and forming a donor-acceptor heterojunction and a photoactive region comprising at least one acceptor material, wherein the at least one donor material has a minimum free orbital energy The level (LUMO Don ) and the highest occupied orbit energy level (HOMO Don ));
An exciton blocking hole filter disposed between the anode and the at least one donor material, wherein the hole filter comprises at least one anode-side wide energy gap material and at least one hole conducting material; Including a mixture)
Including
The at least one anode side wide energy gap material comprises:
The highest occupied orbit energy level (HOMO AS-WG ) that is equal to or higher than the HOMO Don ;
A lowest orbital energy level (LUMO AS-WG ) that is less than or equal to the LUMO Don or greater than the LUMO Don within a range of 0.3 eV;
-HOMO AS-WG - LUMO AS-WG energy gap wider than HOMO Don -LUMO Don energy gap ,
And the glass transition temperature · 85 ℃ or more,
An organic photosensitive optoelectronic device. 前記少なくとも一つのアノード側の広エネルギーギャップ材料は、３，３’，５，５’−テトラ［（ｍ−ピリジル）−フェン−３−イル］ビフェニル（ＢＰ４ｍＰｙ）、２，２’，２”−（１，３，５−ベンジントリイル）−トリス（１−フェニル−１−Ｈ−ベンズイミダゾール）（ＴＰＢｉ）、ビス（２−メチル−８−キノリノレート）−４−（フェニルフェノラト）アルミニウム（ＢＡｌｑ）、トリス（８−ヒドロキシ−キノリナト）アルミニウム（Ａｌｑ３）、トリス（２，４，６−トリメチル−３−（ピリジン−３−イル）フェニル）ボラン（３ＴＰＹＭＢ）、４，４０−（１，３−フェニレン）ビス（２，６−ジ−トリルピリジン−３，５−ジカルボニトリル）（ｍ−ＭＰｙＣＮ）、４，４０−（１，３−フェニレン）ビス（２，６−ジ（ビフェニル−４−イル）ピリジン−３，５−ジカルボニトリル）（ｍ−ＰｈＰｙＣＮ）、４，４０−（１，３−フェニレン）ビス（２，６−ジフェニルピリジン−３，５−ジカルボニトリル）（ｍ−ＰｙＣＮ）、６，６０−（１，４−フェニレン）ビス（２−フェニル−４−ｐ−トリルニコチノニトリル）（ｐ−ＰＰｔＮＮ）、４，４０−（１，４−フェニレン）ビス（２−フェニル−６−ｐ−トリルニコチノニトリル）（ｐ−ＰＰｔＮＴ）、およびそれらの誘導体から選択される材料を含む請求項１３に記載のデバイス。 The at least one anode- side wide energy gap material is 3,3 ′, 5,5′-tetra [(m-pyridyl) -phen-3-yl] biphenyl (BP4mPy), 2,2 ′, 2 ″ — (1,3,5-Benzinetriyl) -tris (1-phenyl-1-H-benzimidazole) (TPBi), bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq ), Tris (8-hydroxy-quinolinato) aluminum (Alq3), tris (2,4,6-trimethyl-3- (pyridin-3-yl) phenyl) borane (3TPYMB), 4,40- (1,3- Phenylene) bis (2,6-di-tolylpyridine-3,5-dicarbonitrile) (m-MPyCN), 4,40- (1,3-phenylene) bis (2,6- (Biphenyl-4-yl) pyridine-3,5-dicarbonitrile) (m-PhPyCN), 4,40- (1,3-phenylene) bis (2,6-diphenylpyridine-3,5-dicarbonitrile) ) (M-PyCN), 6,60- (1,4-phenylene) bis (2-phenyl-4-p-tolylnicotinonitrile) (p-PPtNN), 4,40- (1,4-phenylene) 14. The device of claim 13, comprising a material selected from bis (2-phenyl-6-p-tolylnicotinonitrile) (p-PPtNT), and derivatives thereof. 前記広エネルギーギャップ材料は、８５〜２００℃の間のガラス転移温度を有する請求項１３に記載のデバイス。   The device of claim 13, wherein the wide energy gap material has a glass transition temperature between 85-200 ° C. 前記ＨＯＭＯＡＳ−ＷＧは、前記ＨＯＭＯＤｏｎより大きく、前記ＬＵＭＯＡＳ−ＷＧは、前記ＬＵＭＯＤｏｎより小さい請求項１３に記載のデバイス。 14. The device of claim 13, wherein the HOMO AS-WG is larger than the HOMO Don and the LUMO AS-WG is smaller than the LUMO Don . 前記ＨＯＭＯＨＣは、前記ＨＯＭＯＤｏｎ以下である請求項１３に記載のデバイス。 The device of claim 13, wherein the HOMO HC is less than or equal to the HOMO Don . 前記ＨＯＭＯＡＳ−ＷＧは、前記ＨＯＭＯＨＣより大きい請求項１３に記載のデバイス。 The device of claim 13, wherein the HOMO AS-WG is larger than the HOMO HC . 前記少なくとも一つのドナー材料は、フタロシアニン、サブフタロシアニン、ナフタロシアニン、メロシアニン色素、ホウ素ジピロメテン（ＢＯＤＩＰＹ）色素、チオフェン、低バンドギャップポリマー、ポリアセン、ジインデノペリレン（ＤＩＰ）、スクアライン（ＳＱ）色素、テトラフェニルジベンゾペリフランテン（ＤＢＰ）、およびそれらの誘導体から選択される材料を含む請求項１３に記載のデバイス。   The at least one donor material is phthalocyanine, subphthalocyanine, naphthalocyanine, merocyanine dye, boron dipyrromethene (BODIPY) dye, thiophene, low band gap polymer, polyacene, diindenoperylene (DIP), squaraine (SQ) dye, 14. The device of claim 13, comprising a material selected from tetraphenyl dibenzoperifuranthene (DBP) and derivatives thereof. 前記少なくとも一つの正孔伝導材料は、フタロシアニン、サブフタロシアニン、ナフタロシアニン、メロシアニン色素、ホウ素ジピロメテン（ＢＯＤＩＰＹ）色素、チオフェン、低バンドギャップポリマー、ポリアセン、ジインデノペリレン（ＤＩＰ）、スクアライン（ＳＱ）色素、テトラフェニルジベンゾペリフランテン（ＤＢＰ）、およびそれらの誘導体から選択される材料を含む請求項１３に記載のデバイス。   The at least one hole conducting material includes phthalocyanine, subphthalocyanine, naphthalocyanine, merocyanine dye, boron dipyrromethene (BODIPY) dye, thiophene, low band gap polymer, polyacene, diindenoperylene (DIP), squaraine (SQ). 14. The device of claim 13, comprising a material selected from dyes, tetraphenyl dibenzoperifuranthene (DBP), and derivatives thereof. 前記混合物は、前記少なくとも一つのカソード側の広エネルギーギャップ材料および前記少なくとも一つの電子伝導材料を、体積比で１０：１〜１：１０となる範囲の比率で含む請求項１に記載のデバイス。The device of claim 1, wherein the mixture comprises the at least one cathode-side wide energy gap material and the at least one electron conducting material in a volume ratio of 10: 1 to 1:10. 前記混合物は、前記少なくとも一つのカソード側の広エネルギーギャップ材料および前記少なくとも一つの電子伝導材料を、体積比で２：１〜１：２となる範囲の比率で含む請求項１に記載のデバイス。The device of claim 1, wherein the mixture comprises the at least one cathode-side wide energy gap material and the at least one electron conducting material in a volume ratio of 2: 1 to 1: 2. 前記励起子阻止電子フィルタと前記カソードとの間に配置される少なくとも一つのキャップ層をさらに含む請求項１に記載のデバイス。The device of claim 1, further comprising at least one cap layer disposed between the exciton blocking electron filter and the cathode. 前記少なくとも一つのキャップ層および前記少なくとも一つのカソード側の広エネルギーギャップ材料は、同一の材料を含む請求項２３に記載のデバイス。24. The device of claim 23, wherein the at least one cap layer and the at least one cathode-side wide energy gap material comprise the same material. 前記少なくとも一つの電子伝導材料は、フラーレンおよび官能基化フラーレン誘導体から選択される材料を含む請求項１に記載のデバイス。The device of claim 1, wherein the at least one electron conducting material comprises a material selected from fullerenes and functionalized fullerene derivatives. 前記少なくとも一つの電子伝導材料は、ＣThe at least one electron conductive material is C ６０60 およびＣAnd C ７０70 から選択される材料を含む請求項２５に記載のデバイス。26. The device of claim 25, comprising a material selected from: 前記少なくとも一つのアクセプタ材料は、ＣThe at least one acceptor material is C ６０60 およびＣAnd C ７０70 から選択される材料を含む請求項２６に記載のデバイス。27. The device of claim 26, comprising a material selected from: 前記少なくとも一つのカソード側の広エネルギーギャップ材料は、ＢＰ４ｍＰｙ、ＴＰＢｉ、ＢＡｌｑ、Ａｌｑ３および３ＴＰＹＭＢから選択される材料を含む請求項２６に記載のデバイス。27. The device of claim 26, wherein the at least one cathode-side wide energy gap material comprises a material selected from BP4mPy, TPBi, BAlq, Alq3, and 3TPYMB. 前記励起子阻止電子フィルタと前記カソードとの間に配置される少なくとも一つのキャップ層をさらに含み、前記少なくとも一つのキャップ層および前記少なくとも一つのカソード側の広エネルギーギャップ材料は、同一の材料を含む請求項２８に記載のデバイス。And further including at least one cap layer disposed between the exciton blocking electron filter and the cathode, wherein the at least one cap layer and the at least one cathode-side wide energy gap material include the same material. 30. The device of claim 28. 前記少なくとも一つのカソード側の広エネルギーギャップ材料は、ＴＰＢｉを含む請求項２７に記載のデバイス。28. The device of claim 27, wherein the at least one cathode side wide energy gap material comprises TPBi. 前記励起子阻止電子フィルタと前記カソードとの間に配置される少なくとも一つのキャップ層をさらに含み、前記少なくとも一つのキャップ層は、ＴＰＢｉを含む請求項３０に記載のデバイス。32. The device of claim 30, further comprising at least one cap layer disposed between the exciton blocking electron filter and the cathode, wherein the at least one cap layer comprises TPBi. 前記少なくとも一つのドナー材料は、テトラフェニルジベンゾペリフランテン（ＤＢＰ）を含む請求項３１に記載のデバイス。32. The device of claim 31, wherein the at least one donor material comprises tetraphenyl dibenzoperifuranthene (DBP). 前記少なくとも一つのカソード側の広エネルギーギャップ材料は、ＴＰＢｉを含む請求項１に記載のデバイス。The device of claim 1, wherein the at least one cathode-side wide energy gap material comprises TPBi.
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