JP2015524161A - 電子輸送層において使用するためのイオン性有機化合物を含む配合物 - Google Patents
電子輸送層において使用するためのイオン性有機化合物を含む配合物 Download PDFInfo
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- JP2015524161A JP2015524161A JP2015510668A JP2015510668A JP2015524161A JP 2015524161 A JP2015524161 A JP 2015524161A JP 2015510668 A JP2015510668 A JP 2015510668A JP 2015510668 A JP2015510668 A JP 2015510668A JP 2015524161 A JP2015524161 A JP 2015524161A
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- KBEVZHAXWGOKCP-UHFFFAOYSA-N zinc oxygen(2-) tin(4+) Chemical compound [O--].[O--].[O--].[Zn++].[Sn+4] KBEVZHAXWGOKCP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明は、有機電子(OE)デバイスの、より特定的に有機薄膜太陽電池(OPV)デバイスにおける電子輸送層または電子採集層において使用するためのイオン性有機化合物を含む配合物、かかる配合物の使用を通じて含むかまたは作成される電子輸送層、ならびにかかる配合物または電子輸送層を含むOEおよびOPVデバイスに関する。
緩衝層とも称される界面層についての関心は、電子デバイス、例えば有機発光ダイオード(OLED)、有機薄膜太陽電池(OPV)および電界効果トランジスタ(OFET)において過去数年にわたって相当に上昇した。太陽電池中に組み込まれると、定義により光活性フィルムと電極の1つとの間に包囲されたこれらの界面材料は、デバイスの性能および寿命における改善をもたらす。
1)活性層内の光吸収および励起子生成、通常電子供与および/電子受容(D/A)有機化合物のブレンドからなるBHJ(バルクヘテロ接合)、
2)D/A物理的界面への励起子移動、続いて自由電荷担体中へのそれらの解離
3)受容体(供与体)ドメイン内の自由な電子(正孔)拡散、
4)BHJからカソード(アノード)への電子(正孔)の抽出。
1)それらの抽出を増強するカソード(アノード)での電子(正孔)エネルギー障壁を変化させる、
2)異なる符号の担体間の再結合を低減させるのを補助する選択的なエネルギー障壁を提供する、
3)デバイスの極性を変化させる、
4)BHJのための機械的/化学的保護層またはシード層として、
5)光学的スペーサーとして作用するBHJ全体にわたって入射光子束を再分配する。
1)伝導層、
2)半導電層、
3)双極子層。
本発明は有機塩を含む配合物であって、有機塩が第1のイオン性物質および第2の対イオン性物質を含み、
− 第1の、および第2の物質が共に小分子であり、ならびに
− 第1の物質が、
− 単一の荷電した部分または複数の荷電した部分を含む荷電した有機核、
および、
− 任意に、荷電した有機核に付着した1つまたは2つ以上の置換基、
前記置換基の少なくとも1つが、荷電した有機核の荷電した部分と
符号において反対であるか、または同符号の電荷を有する荷電した
部分を含む、
を含む有機物質であり、ならびに
− 第2の物質が有機、無機または有機金属物質であり、ならびに
− 第1の物質の正味電荷が第2の物質の正味電荷に対して符号に
おいて反対である
ことを特徴とする、前記配合物に関する。
好ましくは、溶媒を、極性溶媒から、非常に好ましくは水、アルコールおよび極性非アルコール系有機溶媒、または前述のものの組み合わせから選択する。
別の好ましい態様において、有機塩は、イオン液体である。
本発明はさらに、層の製造方法であって、本明細書中に記載した配合物を基板上に堆積させ、溶媒を除去し、任意に層を室温より高い温度で乾燥するステップを含む、前記方法に関する。
上記のデバイスのコンポーネントは、限定されずに、半導体フィルム、電荷注入層、電荷輸送層、中間層、平坦化層、帯電防止フィルム、高分子電解質膜(PEM)、レーザー材料、伝導性基板および伝導性パターンを含む。
本明細書中で使用する用語「ポリマー」は、高い相対分子量の分子を意味するものと理解され、その構造は、本質的に、実際に、または概念的に、低い相対分子量の分子から誘導される単位の複数の繰り返しを含む (Pure Appl. Chem., 1996, 68, 2291)。用語「オリゴマー」は、中間の相対分子量の分子を意味するものと理解され、その構造は、本質的に、実際に、または概念的に、より低い相対分子量の分子から誘導される少数の複数の単位を含む(Pure Appl. Chem., 1996, 68, 2291)。本明細書中本発明で使用する好ましい意味において、ポリマーは、>1つ、つまり少なくとも2つの繰り返し単位、好ましくは≧5つの繰り返し単位を有する化合物を意味するものと理解され、オリゴマーは、>1つかつ<10個、好ましくは<5つの繰り返し単位を有する化合物を意味するものと理解されるだろう。
第1の物質は、有機荷電核を含み、それは、例えばN複素環式部分、例えばピロリジニウム、チアゾリウム、オキサゾリウム、トリアゾリウムもしくはカルバゾリウムであるか、またはスルホニウム、グアニジニウム、ホスホニウムもしくはアンモニウム部分を含む。
− 1〜20個のC原子を有し、任意に部分的に、しかしヘテロ原子に対してα位においてではなくフッ素化され得、かつまた炭素原子間の任意の位置において酸素または/および硫黄原子を含むことができる、直鎖状または分枝状アルキル、あるいは
− 5〜7個のC原子を有し、1〜6個のC原子を有するアルキル基によって置換されていてもよく、かつここで置換基R1’、R2’、R3’および/またはR4’は、一緒にまた環系を形成してもよく、かつ反応性化合物の場合において、置換基R1’〜R4’の1つまたは2つ以上はまた、好ましくは2〜12個のC原子を有し、重合性であるかまたは架橋可能な官能基に結合するアルキレンスペーサー基Spを示してもよい、飽和の、部分的に、または完全に不飽和のシクロアルキル。
有機塩がILまたはPILである場合において、それは、好ましくは、溶媒(単数または複数)に、0.0001vol%〜10vol%、より好ましくは0.001vol%〜2.0vol%の濃度で溶解する。
− 配合物を基板上に堆積させる、
− 溶媒を例えば蒸発によって、好ましくは熱および/または減圧下で除去する、
− 任意に層を室温より高い温度で乾燥する
を含むプロセスによって形成することができる。
ETL層は、約30ミクロン未満であり得る。様々な電子デバイス適用のために、厚さは、厚さ約1ミクロン未満であり得る。層を、前述の溶液コーティングまたは印刷手法のいずれかによって例えば電子デバイスの部分上に堆積させてもよい。
− 配合物を、基板上に、スピンコーティングまたは他の印刷手法、例えばスロットダイコーティング、インクジェット印刷、スプレー、ドクターブレードによって、優先的にはスピンコーティングまたはドクターブレーディングによって加工する、
− 配合物を、10℃〜90℃の温度で、好ましくは室温で加工する、
− 配合物を、10℃〜120℃の温度で、好ましくは室温で加工する、
− 配合物から形成した層は、室温〜200℃の温度で、および/またはUV露光によって架橋する、
− 配合物から形成した層を、電極、ETL、HTL、BHJ、プラスチック基板、ガラス基板、伝導層または半導体層から選択される、好ましくはOPVデバイス中のBHJまたは金属酸化物半導体層、逆転OPVデバイス中の伝導層またはETLから選択される基板上に提供する、
− ETLによって、アルミニウムカソードとBHJとの間のETLを有しない対照のデバイスと比較して、BHJおよびアルミニウム電極を含むOPVデバイスの改善された性能、好ましくはVOCおよび/またはFFの増加がもたらされる、
OPVデバイスは、例えば文献から知られている任意のタイプであり得る(例えばWaldauf et al., Appl. Phys. Lett., 2006, 89, 233517を参照)。
− 任意に基板、
− アノードとして作用する、好ましくは金属酸化物、例えばITOを含む高い仕事関数の電極、
− 好ましくは金属、例えばアルミニウムを含み、カソードとして作用する、低い仕事関数の電極、
ここで電極の少なくとも1つ、好ましくはアノードは、可視光線に対して透明である。
− 任意に基板、
− 例えばITOを含み、カソードとして作用する、高い仕事関数の金属または金属酸化物電極、
− 本発明の配合物を含むかまたはそれから形成される、ETL層、
− 高い仕事関数の金属、例えば銀を含み、アノードとして作用する、電極、
ここで電極の少なくとも1つ、好ましくはカソードは、可視光線に対して透明である。
p型半導体は、例えば共役有機ポリマーである。
この明細書の記載および特許請求の範囲の全体にわたって、語「含む(comprise)」および「含む(contain)」ならびに当該語の変化形、例えば「含む(comprising)」および「含む(comprises)」は、「含むがそれらには限定されない」を意味し、他の構成成分を除外することを意図しない(かつ除外しない)。
(「C」と称した例は比較例である。)
以下の層順序を有するOPVデバイスを、以下に記載するように製造した:ガラス基板/ITO電極/HTL/BHJ/ETL/Al電極
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、塩S1、S2もしくはS3に基づいたETLを使用した、またはETLを使用しないデバイスの平均的なパラメーターを、表1に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、塩S3に基づいたETLを使用した(例9)、またはETLを有しない(例7C)、または溶媒によって洗浄したのみである(例8C)デバイスの平均的なパラメーターを、表2に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、塩1および水とイソプロパノールとの種々の組み合わせに基づいたETLを使用した、またはETLを有しない(例10C)デバイスの平均的なパラメーターを、表3に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、種々の濃度での塩1に基づいたETLを使用した、またはETLを有しない(例16)デバイスの平均的なパラメーターを、表4に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、塩S1(例25)もしくはカルシウム(例23C)に基づいたETLを使用した、またはETLを有しない(例24C)デバイスの平均的なパラメーターを、表5に要約する。
構造{ガラス/ITO/BHJ/ETL/Al}を有し、塩1に基づいたETLおよびBHJにおける種々の電子供与ポリマーを使用したデバイスの平均的なパラメーターを、表6に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、0.5vol%のイオン液体IL1および99.5vol%のメタノールを含む配合物から得られたETLを使用した(例35)、またはETLを有しない(例34C)デバイスの平均的なパラメーターを、表7に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、0.018vol%のイオン液体IL1および99.982vol%のイソプロパノールを含む配合物から得られたETLを使用した(例37)、またはETLを有しない(例36C)デバイスの平均的なパラメーターを、表8に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、イオン液体IL1およびイソプロパノールを種々の容積比において含む配合物から得られたETLを使用した(例39〜41)、またはETLを有しない(例38C)デバイスの平均的なパラメーターを、表9に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Al}を有し、0.18vol%のイオン液体IL1および99.82vol%のイソプロパノールもしくはメタノールのいずれかを含む配合物から得られたETLを使用した(例43〜44)、またはETLを有しない(例42C)デバイスの平均的なパラメーターを、表10に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Ag/Al}を有し、塩S1に基づいたETLを使用した(例46)、またはETLを有しない(例45C)デバイスの平均的なパラメーターを、表11に要約する。
構造{ガラス/ITO/BHJ(LisiconOPVポリマーP1:PCBM)/ETL/Ag/Al}を有し、イオン液体IL2、もしくはイオン液体IL3、もしくはイオン液体IL3、もしくはイオン液体IL4、もしくはイオン液体IL5、もしくはイオン液体IL6、もしくはイオン液体IL7、もしくはイオン液体IL8に基づいたETLを使用した、またはETLを有しない(例47C)デバイスの平均的なパラメーターを、表12に要約する。
Claims (28)
- 有機塩を含む配合物であって、有機塩が第1のイオン性物質および第2の対イオン性物質を含み、
− 第1の、および第2の物質が小分子であり、ならびに
− 第1の物質が、
− 単一の荷電した部分または複数の荷電した部分を含む荷電した有機核、
および、
− 任意に、荷電した有機核に付着した1つまたは2つ以上の置換基、
前記置換基の少なくとも1つが、荷電した有機核の荷電した部分と
符号において反対であるか、または同符号の電荷を有する荷電した
部分を含む、
を含む有機物質であり、ならびに
− 第2の物質が有機、無機または有機金属物質であり、ならびに
− 第1の物質の正味電荷が第2の物質の正味電荷に対して符号に
おいて反対である
ことを特徴とする、前記配合物。 - さらに1種または2種以上の溶媒を含む、請求項1に記載の配合物。
- 溶媒が水、アルコールおよび極性非アルコール系有機溶媒または前述のものの組み合わせから選択される、請求項2に記載の配合物。
- 溶媒がイソプロパノール、エタノール、水およびイソプロパノールの組み合わせ、または水およびエタノールの組み合わせから選択される、請求項3に記載の配合物。
- 第1の物質がイミダゾリウム、ジアルキルイミダゾリウム、トリアルキルイミダゾリウム、ジアルキルピロリジニウム、モノまたはジアルキルピリジニウム、トリアルキルスルホニウム、カルバゾリウム、インドリウム、ピペリジニウム、モルホリニウム、ピリミジニウム、ピリダジニウム、ピラジニウム、ピラゾリウム、ピロリニウム、ピリミジニウム、ピラジニウム、チアゾリウム、オキサゾリウム、トリアゾリウム、トリアジニウム、グアニジニウム、ウラニウム、アンモニウム、スルホニウム、ホスホニウムからなる群から選択された部分を含む、請求項1〜4のいずれか一項に記載の配合物。
- 第2の物質がハロゲン化物、ホウ酸塩、イミド、硝酸塩、リン酸塩、スルホン酸塩、硫酸塩、コハク酸塩、ナフテネート、カルボン酸塩またはO−複素環式部分を含む、請求項1〜5のいずれか一項に記載の配合物。
- 第2の物質がイミダゾリウム、ジアルキルイミダゾリウム、トリアルキルイミダゾリウム、ジアルキルピロリジニウム、モノまたはジアルキルピリジニウム、トリアルキルスルホニウム、カルバゾリウム、インドリウム、ピペリジニウム、モルホリニウム、ピリミジニウム、ピリダジニウム、ピラジニウム、ピラゾリウム、ピロリニウム、ピリミジニウム、ピラジニウム、チアゾリウム、オキサゾリウム、トリアゾリウム、トリアジニウム、グアニジニウム、ウラニウム、アンモニウム、スルホニウム、ホスホニウムおよび周期表の1族のカチオン、好ましくはH+、Na+またはK+からなる群から選択された部分を含む、請求項1〜6のいずれか一項に記載の配合物。
- 第1の物質が有機両性イオン性化合物を含み、第2の物質が有機または無機対イオンを含む、請求項1〜7のいずれか一項に記載の配合物。
- 第1の物質が好ましくはシアニン染料、メロシアニン染料、スクアリリウム染料またはポリメチン染料から選択された両性イオン性染料を含む、請求項8に記載の配合物。
- 溶媒中の塩の濃度が0.001mg/ml〜30mg/mlである、請求項1〜9のいずれか一項に記載の配合物。
- 有機塩がイオン液体(IL)または重合性イオン液体(PIL)である、請求項1〜9のいずれか一項に記載の配合物。
- 溶媒中の塩の濃度が0.0001〜10vol%である、請求項11に記載の配合物。
- 請求項1〜12のいずれか一項に記載の配合物の使用を通じて含むかまたは作成される層。
- 有機電子デバイス中の電子輸送層(ETL)である、請求項13に記載の層。
- 請求項13または14に記載の層の製造方法であって、請求項1〜12のいずれか一項に記載の配合物を基板上に堆積させ、溶媒を除去するステップを含む、前記方法。
- 配合物をスピンコーティングまたは印刷、好ましくはスロットダイコーティング、インクジェット印刷、スプレーまたはドクターブレーディングにより堆積させる、請求項15に記載の方法。
- 配合物を空気、N2の雰囲気または水圧の下で加工する、請求項15または16に記載の方法。
- 配合物を10℃〜120℃の温度で、好ましくは室温で堆積させる、請求項15〜17のいずれか一項に記載の方法。
- 層を室温〜200℃、好ましくは室温〜60℃の温度で乾燥する、請求項15〜18のいずれか一項に記載の方法。
- 層を、電極、ETL、HTL、BHJ、プラスチック基板、ガラス基板、伝導層または半導体層から選択された、好ましくはOPVデバイス中のBHJまたは金属酸化物半導体層、逆転OPVデバイス中の伝導層またはETLから選択された基板上で形成する、請求項15〜19のいずれか一項に記載の方法。
- 請求項1〜12のいずれか一項に記載の配合物または請求項13もしくは14に記載の層の、有機電子デバイス中の電子輸送層(ETL)としての使用。
- 請求項1〜12のいずれか一項に記載の配合物または請求項13もしくは14に記載の層の、光学的、電気光学的、電子的、エレクトロルミネセントもしくはフォトルミネセントデバイス中の、またはかかるデバイスのコンポーネント中の、またはかかるデバイスもしくはコンポーネントを含むアセンブリ中のETLとしての使用。
- 請求項1〜12のいずれか一項に記載の配合物または請求項13もしくは14に記載の層を含む、光学的、電気光学的、電子的、エレクトロルミネセントもしくはフォトルミネセントデバイス、またはそれらのコンポーネント、またはそれを含むアセンブリ。
- 有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、有機薄膜太陽電池デバイス(OPV)、有機太陽電池、レーザーダイオード、ショットキーダイオード、フォトダイオード、光伝導体、光検出器、メモリスタ、変換器、光相互接続、発光電気化学的セル、光トランジスタ、トンネル接合、スピンバルブデバイスから選択される、請求項23に記載の光学的、電気光学的、電子的、エレクトロルミネセントまたはフォトルミネセントデバイス。
- OFET、バルクヘテロ接合(BHJ)OPVデバイスまたは逆転BHJ OPVデバイスである、請求項23または24に記載のデバイス。
- アルミニウム、金、銀、カルシウム、マグネシウムまたはバリウムのカソードを含むBHJ OPVデバイスまたは逆転BHJ OPVデバイスである、請求項25に記載のデバイス。
- 半導体フィルム、電荷注入層、電荷輸送層、中間層、平坦化層、帯電防止フィルム、高分子電解質膜(PEM)、レーザー材料、伝導性基板および伝導性パターンから選択される、請求項23に記載のコンポーネント。
- 集積回路(IC)、無線自動識別(RFID)タグまたはそれらを含むセキュリティマーキングもしくはセキュリティデバイス、フラットパネルディスプレイまたはそのバックライト、電子写真装置、電子写真記録装置、フォトスイッチ、有機記憶装置、センサーデバイス、バイオセンサーおよびバイオチップから選択される、請求項23に記載のアセンブリ。
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JP2020024404A (ja) * | 2018-07-31 | 2020-02-13 | キヤノン株式会社 | 電子写真用部材、プロセスカートリッジおよび電子写真画像形成装置 |
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TW201402779A (zh) | 2014-01-16 |
EP2847807A1 (en) | 2015-03-18 |
JP6502248B2 (ja) | 2019-04-17 |
WO2013167224A1 (en) | 2013-11-14 |
CN104272485A (zh) | 2015-01-07 |
KR20150017730A (ko) | 2015-02-17 |
EP2847807B1 (en) | 2019-11-27 |
CN104272485B (zh) | 2018-11-16 |
US20150105560A1 (en) | 2015-04-16 |
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