JP2019001754A - 化合物、化合物の製造方法及びグラフェンナノリボンの製造方法 - Google Patents
化合物、化合物の製造方法及びグラフェンナノリボンの製造方法 Download PDFInfo
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- JP2019001754A JP2019001754A JP2017118618A JP2017118618A JP2019001754A JP 2019001754 A JP2019001754 A JP 2019001754A JP 2017118618 A JP2017118618 A JP 2017118618A JP 2017118618 A JP2017118618 A JP 2017118618A JP 2019001754 A JP2019001754 A JP 2019001754A
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- 229910021389 graphene Inorganic materials 0.000 title claims abstract description 118
- 239000002074 nanoribbon Substances 0.000 title claims abstract description 118
- 150000001875 compounds Chemical class 0.000 title claims abstract description 73
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims abstract description 14
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005382 boronyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000002243 precursor Substances 0.000 abstract description 64
- 229920000642 polymer Polymers 0.000 abstract description 49
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- YXLIKDGPYMCPCT-UHFFFAOYSA-N 1-bromo-2,3,4,5-tetrafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1Br YXLIKDGPYMCPCT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical class C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- MUJNAWXXOJRNGK-UHFFFAOYSA-N n-[3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propyl]cyclohexanamine Chemical compound C1=2CCCCC=2C2=CC(C)=CC=C2N1CCCNC1CCCCC1 MUJNAWXXOJRNGK-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
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- 239000002094 self assembled monolayer Substances 0.000 description 2
- 239000013545 self-assembled monolayer Substances 0.000 description 2
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- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- 238000003775 Density Functional Theory Methods 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/04—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of carbon-silicon compounds, carbon or silicon
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- 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
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- 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
- C01B32/182—Graphene
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- C01B32/186—Preparation by chemical vapour deposition [CVD]
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/30—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by a Diels-Alder synthesis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
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- B82Y40/00—Manufacture or treatment of nanostructures
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- C01B2204/00—Structure or properties of graphene
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Abstract
Description
また、一観点によれば、上記のような化合物の製造方法、及び上記のような化合物を用いたグラフェンナノリボンの製造方法が提供される。
図1はグラフェンナノリボンの第1の合成例について説明する図、図2はグラフェンナノリボンの第2の合成例について説明する図である。
まず、図1に示す第1の例では、得られる7ACGNR120のバンドギャップが比較的大きく、半導体装置への適用を考えた場合、良好な電極接合を形成することが必ずしも容易でない、或いは使用可能な電極材料の種類が限定されるといった課題がある。
グラフェンナノリボンの前駆体として用いる化合物は、式(2)に示すような構造を有する。
まず、式(3)に示すような化合物、及び式(4)に示すような化合物を準備する。
得られた式(5)の化合物のアミノ基(NH2基)を脱離基Xに変換し、式(6)に示すような化合物を得る。
上記のようなグラフェンナノリボンの前駆体の合成例を図3に示す。
図3には、式(3)に相当する化合物10として、2,6−ジヨード−4−ニトロアニリン(2,6-diiodo-4-nitroaniline)を用い、式(4)に相当する化合物20として、2−ビフェニルボロン酸(2-biphenyl-boronic acid)を用いる例を示している。化合物10は、式(3)のXがI原子である構造を有する。化合物20は、式(4)のRがH原子、ZがB(OH)2基である構造を有する。
更に、このようにして得られた化合物40と、式(7)に相当する化合物50(式(7)のXがBr原子、ZがB(OH)2基)とを、鈴木カップリングによりカップリングする。これにより、式(8)に相当する化合物60(式(8)のXがBr原子、RがH原子)を得る。
続いて、上記のような前駆体を用いたグラフェンナノリボンの合成について説明する。
図4はグラフェンナノリボン合成ルートの一例を示す図である。
図4には、グラフェンナノリボンの前駆体としてDBSP70(図3)を用いる例を示している。DBSP70を用いた合成では、まず、DBSP70が、加熱された触媒金属基板上に真空蒸着される。触媒金属基板としては、金(Au)、銀(Ag)、銅(Cu)等の(111)面のほか、(110)面や(100)面、更には(788)面等の高指数面も用いられる。ここでは、Au(111)面を例にして説明する。超高真空中で清浄化されたAu(111)面が、200℃〜300℃程度に保持され、DBSP70が真空蒸着される。この時の蒸着量は、1分子層程度になるように調節することが望ましい。Au(111)面上では、吸着したDBSP70群がウルマン反応によって重合される。これにより、図4に示すようなポリマー鎖80が合成される。
ここでは、上記図3及び図4に示したDBSP70とそれを用いて合成される、上記図4に示したポリマー鎖80及び9ACGNR90を例にする。また、これとの比較には、上記図1に示したDBBA100とそれを用いて合成されるポリマー鎖110及び7ACGNR120、並びに上記図2に示したDBTP200とそれを用いて合成されるポリマー鎖210及び9ACGNR220を用いる。
図5(A)には、DBSP70を用いて合成される9ACGNR90を示し、図5(B)には、そのバンド構造を密度汎関数法で見積もった結果を示している。比較のため、図6(A)には、DBBA100を用いて合成される7ACGNR120を示し、図6(B)には、そのバンド構造を密度汎関数法で見積もった結果を示している。
図7〜図9は前駆体から合成される分子間の相互作用について説明する図である。
ここでは、前駆体としてDBSP70を用いることで得られる効果を説明したが、式(2)で表される各種化合物を用いた場合にも、上記同様の効果を得ることが可能である。
図10及び図11は前駆体及びグラフェンナノリボンの合成ルートの別例について説明する図である。
図12は前駆体合成ルートの別例について説明する図である。図12(A)には、前駆体合成ルートの第1の例を示し、図12(B)には、前駆体合成ルートの第2の例を示している。
次に、第2の実施の形態について説明する。
図13は半導体装置の第1の例を示す図である。図13には、半導体装置の要部断面図を模式的に図示している。
図14に示す半導体装置600は、トップゲート型FETの一例である。半導体装置600は、支持基板610、グラフェンナノリボン620、電極630a、電極630b、ゲート絶縁膜640及びゲート電極650を有する。
図15に示す半導体装置700は、ショットキーバリアダイオードの一例である。半導体装置700は、支持基板710、グラフェンナノリボン720、電極730及び電極740を有する。
図16に示す半導体装置800は、積層型太陽電池の一例である。半導体装置800は、下部電極810、グラフェンナノリボン820、キャリア輸送層830及び上部電極840を有する。
上記第2の実施の形態で述べたような半導体装置500,600,700,800等は、各種電子装置(電子機器とも称する)に搭載することができる。例えば、コンピュータ(パーソナルコンピュータ、スーパーコンピュータ、サーバ等)、スマートフォン、携帯電話、タブレット端末、センサ、カメラ、オーディオ機器、測定装置、検査装置、製造装置といった、各種電子装置に用いることができる。
図17に示すように、例えば、上記図13に示したような半導体装置500が、各種電子装置900に搭載(内蔵)される。上記のように半導体装置500では、グラフェンナノリボン530の高いキャリア移動度を活かした、高速のFETが実現される。そのような半導体装置500を搭載した、高性能の電子装置900が実現される。
70 DBSP
80,110,210 ポリマー鎖
81 側鎖
90,90a,90b,220 9ACGNR
100 DBBA
120 7ACGNR
200 DBTP
500,600,700,800 半導体装置
510,650 ゲート電極
520,640 ゲート絶縁膜
530,620,720,820 グラフェンナノリボン
540a,540b,630a,630b,730,740 電極
610,710 支持基板
810 下部電極
830 キャリア輸送層
840 上部電極
900 電子装置
D ポリマー伸張方向
Eg1,Eg2 バンドギャップ
Claims (5)
- 下記一般式(1)で表されることを特徴とする化合物。
- 前記Xは、相互に独立して、臭素原子、塩素原子又はヨウ素原子であることを特徴とする請求項1に記載の化合物。
- 下記一般式(2)で表される第1化合物と、下記一般式(3)で表される第2化合物とをカップリングし、アミノ基を脱離基に変換して、第3化合物を合成する工程と、
前記第3化合物と、下記一般式(4)で表される第4化合物とをカップリングし、ニトロ基を脱離基に変換して、下記一般式(5)で表される第5化合物を合成する工程と
を含むことを特徴とする化合物の製造方法。
- 前記第5化合物を形成する工程後、前記第5化合物の誘導体を形成する工程を含むことを特徴とする請求項3に記載の化合物の製造方法。
- 下記一般式(6)で表される化合物群の重合及び芳香環化により、下記一般式(7)で表されるグラフェンナノリボンを合成する工程を含むことを特徴とするグラフェンナノリボンの製造方法。
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