JP6306720B2 - フラーレン誘導体及びフラーレン誘導体を含む有機電子素子 - Google Patents
フラーレン誘導体及びフラーレン誘導体を含む有機電子素子 Download PDFInfo
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- JP6306720B2 JP6306720B2 JP2016545353A JP2016545353A JP6306720B2 JP 6306720 B2 JP6306720 B2 JP 6306720B2 JP 2016545353 A JP2016545353 A JP 2016545353A JP 2016545353 A JP2016545353 A JP 2016545353A JP 6306720 B2 JP6306720 B2 JP 6306720B2
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- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/152—Fullerenes
- C01B32/156—After-treatment
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/152—Fullerenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/38—Alcohols containing six-membered aromatic rings and other rings and having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C07C43/168—Unsaturated ethers containing six-membered aromatic rings containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Description
nは、1ないし5の整数であり、
nが2以上の場合、括弧内の構造は同一であるか異なっており、
Cnは、C60ないしC120のフラーレンであり、
R1ないしR6は、互いに同一であるか異なっており、それぞれ独立して、水素;ハロゲン基;ニトロ基;シアノ基;カルボン酸基;ヒドロキシ基;置換もしくは非置換のカルボニル基;スルホ基(−SO3H);置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエステル基;置換もしくは非置換のチオエステル基;置換もしくは非置換のアミド基;置換もしくは非置換のエーテル基;置換もしくは非置換のスルホン基(−SO2−);置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールアルキル基;置換もしくは非置換のヘテロアリールアルキル基;置換もしくは非置換のアリール基;又は置換もしくは非置換の複素環基であるか、隣接する置換基は、互いに結合して、置換もしくは非置換の炭化水素環;又は置換もしくは非置換の複素環を形成し、
R1ないしR6のうち少なくとも一つは、
oは、1ないし3の整数であり、oが2以上の整数の場合、2以上のLは互いに同一であるか異なっており、
Lは、置換もしくは非置換のアルキレンであり、
Rは、水素;カルボン酸基;置換もしくは非置換のカルボニル基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエステル基;置換もしくは非置換のチオエステル基;置換もしくは非置換のアミド基;置換もしくは非置換のスルホン基(−SO2−);置換もしくは非置換のアリールアルキル基;置換もしくは非置換のアリール基;又は置換もしくは非置換の複素環基である。
上記有機物層のうち1層以上は、上記フラーレン誘導体を含むものである有機電子素子を提供する。
本明細書の一実施態様に係るフラーレン誘導体は、
R、Cn、n、o、L及びR1ないしR6の定義は、上記化学式1で定義した通りである。
Cn、n、o、L及びR1ないしR6の定義は、上記化学式1で定義した通りであり、
R7及びR8は、互いに同一であるか異なっており、それぞれ独立して、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエーテル基;置換もしくは非置換のスルホニル基;置換もしくは非置換のアリールアルキル基;置換もしくは非置換の環状ケトン;置換もしくは非置換のアリール基;又は置換もしくは非置換の複素環基である。
nの定義は、上記化学式1で定義した通りである。
Rmは、水素、置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;N、O、S原子のうち1つ以上を含む置換もしくは非置換の芳香族又は脂肪族の複素環基、又は置換もしくは非置換のアリール基である。
上記製造例1−1−1ないし製造例1−1−9の有機太陽電池の光電変換特性を100mW/cm2(AM 1.5)の条件で測定し、下記表1にその結果を示す。
上記製造例1−1−1で製造した化合物とP3HTを1:0.7でクロロベンゼン(Chlorobenzene, CB)に溶かして複合溶液(composit solution)を製造した。このとき、濃度は2.0wt%に調節し、有機太陽電池はITO/PEDOT:PSS/光活性層/Alの構造にした。ITOがコーティングされたガラス基板は、蒸留水、アセトン、2−プロパノールを用いて超音波洗浄し、ITOの表面を10分間オゾン処理した後、45nmの厚さでPEDOT:PSS(baytrom P)をスピンコートして、120℃で10分間熱処理した。光活性層のコーティングのためには、化合物−P3HT複合溶液を0.45μmPPシリンジフィルター(syringe filter)で濾過した後にスピンコートして、3×10−8torrの真空下で熱蒸発器(thermal evaporator)を用いて200nmの厚さでAlを蒸着して、有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−2で製造した化学式1−1−2を使用し、P3HTと上記フラーレン誘導体の割合を 1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−3で製造した化学式1−1−3を使用し、P3HTと上記フラーレン誘導体の割合を 1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−4で製造した化学式1−1−4を使用し、P3HTと上記フラーレン誘導体の割合を 1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−5で製造した化学式1−1−5を使用し、P3HTと上記フラーレン誘導体の割合を1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−6で製造した化学式1−1−6を使用し、P3HTと上記フラーレン誘導体の割合を 1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−7で製造した化学式1−1−7を使用し、P3HTと上記フラーレン誘導体の割合を1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−8で製造した化学式1−1−8を使用し、P3HTと上記化学式1−1−8の化合物の割合を1:0.7で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、化学式1−1−1の代わりに製造例1−1−9で製造した化学式1−1−9を使用し、P3HTと上記フラーレン誘導体の割合を1:1で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
実施例1において、下記化学式1−2−1で表される高分子と化学式1−1−1を1:0.7で製造したことを除いては、実施例1−1と同一の方法で有機太陽電池を製造した。
P3HTとPC61BM を1:0.7で1,2−ジクロロベンゼン(1,2-dichlorobenzene, DCB)に溶かして、複合溶液(composit solution)を製造した。このとき、濃度は1.0〜2.0wt%に調節し、有機太陽電池はITO/PEDOT:PSS/光活性層/LiF/Alの構造にした。ITOがコーティングされたガラス基板は、蒸留水、アセトン、2−プロパノールを用いて超音波洗浄し、ITOの表面を10分間オゾン処理した後、45nmの厚さでPEDOT:PSS(baytrom P)をスピンコートして、120℃で10分間熱処理した。光活性層のコーティングのためには、化合物−PCBM複合溶液を0.45μmPPシリンジフィルター(syringe filter)で濾過した後にスピンコートして、120℃で5分間熱処理し、3×10−8torrの真空下で熱蒸発器(thermal evaporator)を用いてLiFを7Å蒸着した後、200nmの厚さでAlを蒸着して、有機太陽電池を製造した。
102:第1電極
103:正孔輸送層
104:光活性層
105:第2電極
Claims (18)
- 下記化学式1で表されるフラーレン誘導体:
nは、1ないし5の整数であり、
nが2以上の場合、括弧内の構造は同一であるか異なっており、
Cnは、C60ないしC120のフラーレンであり、
R1ないしR6のうち一つの基は、
R1ないしR6のうち前記一つの基以外の基は、互いに同一であるか異なっており、それぞれ独立して、水素;ハロゲン基;ニトロ基;シアノ基;カルボン酸基;ヒドロキシ基;置換のカルボニル基;スルホ基(−SO3H);置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエステル基;置換もしくは非置換のチオエステル基;置換もしくは非置換のアミド基;置換もしくは非置換のエーテル基;置換のスルホン基(−SO2−);置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールアルキル基;置換もしくは非置換のヘテロアリールアルキル基;置換もしくは非置換のアリール基;又は置換もしくは非置換の複素環基であるか、隣接する置換基は、互いに結合して、置換もしくは非置換の炭化水素環;又は置換もしくは非置換の複素環を形成し、
oは、1ないし3の整数であり、oが2以上の整数の場合、2以上のLは互いに同一であるか異なっており、
Lは、置換もしくは非置換のアルキレンであり、
Rは、水素;カルボン酸基;置換のカルボニル基;非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエステル基;置換もしくは非置換のチオエステル基;置換もしくは非置換のアミド基;置換のスルホン基(−SO2−);置換もしくは非置換のアリールアルキル基;又は置換もしくは非置換の複素環基であり、
前記置換もしくは非置換とは、ハロゲン基;ニトロ基;シアノ基;ヒドロキシ基;カルボニル基;スルホ基;アルキル基;アリル基;アルコキシ基;シクロアルキル基;アルケニル基;エーテル基;スルホン基;スルホキシ基;アリールアルキル基;アリール基;複素環基からなる群より選択された1以上の置換基で置換されているか、もしくは置換されておらず、または上記例示された置換基のうち2以上の置換基が連結された置換基で置換されているか、もしくは置換されていないことを意味する。 - 前記化学式1で表されるフラーレン誘導体は、下記化学式2又は3で表されるものである請求項1に記載のフラーレン誘導体:
R、Cn、n、o、L及びR1ないしR6の定義は、前記化学式1で定義した通りである。 - 前記化学式1で表されるフラーレン誘導体は、下記化学式2−1又は化学式3−1で表されるものである請求項1に記載のフラーレン誘導体:
Cn、n、o、L及びR1ないしR6の定義は、前記化学式1で定義した通りであり、
R7及びR8は、互いに同一であるか異なっており、それぞれ独立して、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のエーテル基;置換のスルホニル基;置換もしくは非置換のアリールアルキル基;置換もしくは非置換の環状ケトン;置換もしくは非置換のアリール基;又は置換もしくは非置換の複素環基である。 - Rは、水素;置換もしくは非置換のアルキル基;又は置換のカルボニル基である請求項1に記載のフラーレン誘導体。
- R7及びR8は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアリール基;置換もしくは非置換の環状ケトン;又は置換もしくは非置換の複素環基である請求項3に記載のフラーレン誘導体。
- 化学式1で表されるフラーレン誘導体は、下記化学式1−1−1ないし1−1−31のうちいずれか一つで表されるものである請求項1に記載のフラーレン誘導体:
nの定義は、前記化学式1で定義した通りである。 - 第1電極;前記第1電極と対向して備えられる第2電極;及び前記第1電極と前記第2電極との間に備えられる1層以上の有機物層を含む有機電子素子であって、
前記有機物層のうち1層以上は、請求項1ないし請求項6のいずれか一項に記載のフラーレン誘導体を含むものである有機電子素子。 - 前記有機電子素子は、有機発光素子;有機太陽電池;及び有機トランジスタからなる群より選択されるものである請求項7に記載の有機電子素子。
- 前記有機電子素子は、第1電極;前記第1電極と対向して備えられる第2電極;及び前記第1電極と前記第2電極との間に備えられる1層以上の有機物層を含む有機太陽電池であって、前記有機物層のうち1層以上が、前記フラーレン誘導体を含む請求項7に記載の有機電子素子。
- 前記有機物層は、光活性層を含み、
前記光活性層は、n型有機物層及びp型有機物層を含む二層薄膜(bilayer)構造であり、
前記n型有機物層は、前記フラーレン誘導体を含むものである請求項9に記載の有機電子素子。 - 前記有機物層は、光活性層を含み、
前記光活性層は、電子供与体物質及び電子受容体物質を含み、
前記電子受容体物質は、前記フラーレン誘導体を含むものである請求項9に記載の有機電子素子。 - 前記有機電子素子は、前記電子供与体物質と前記電子受容体物質がバルクヘテロ接合(BHJ)を構成するものである請求項11に記載の有機電子素子。
- 前記有機物層は、光活性層;及び前記光活性層と前記第1電極又は前記第2電極との間に備えられた有機物層を含み、
前記光活性層と前記第1電極又は前記第2電極との間に備えられた有機物層は、前記フラーレン誘導体を含むものである請求項7に記載の有機電子素子。 - 前記光活性層と前記第1電極又は前記第2電極との間に備えられた有機物層に含まれたフラーレン誘導体は、電子伝達物質である請求項13に記載の有機電子素子。
- 前記光活性層と前記第1電極又は前記第2電極との間に備えられた有機物層は、金属酸化物(metal oxide)層を含み、
前記金属酸化物層と光活性層との間に有機物層を備え、
前記有機物層は、前記フラーレン誘導体を含むものである請求項13に記載の有機電子素子。 - 前記光活性層と前記第1電極又は前記第2電極との間に備えられた有機物層に含まれたフラーレン誘導体は、電子注入物質である請求項13に記載の有機電子素子。
- 前記有機電子素子は、ノーマル(normal)構造であり、
前記有機物層は、光活性層;及び前記光活性層と前記第2電極との間に備えられた有機物層を含み、
前記光活性層と第2電極との間に備えられた有機物層は、前記フラーレン誘導体を含み、
前記第1電極は、アノード電極であり、前記第2電極は、カソード電極である請求項9に記載の有機電子素子。 - 前記有機電子素子は、逆(inverted)構造であり、
前記有機物層は、光活性層;及び前記光活性層と前記第2電極との間に備えられた有機物層を含み、
前記光活性層と第2電極との間に備えられた有機物層は、前記フラーレン誘導体を含み、
前記第1電極は、アノード電極であり、前記第2電極は、カソード電極である請求項9に記載の有機電子素子。
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