JP6165782B2 - 有機半導体組成物 - Google Patents
有機半導体組成物 Download PDFInfo
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- JP6165782B2 JP6165782B2 JP2014558215A JP2014558215A JP6165782B2 JP 6165782 B2 JP6165782 B2 JP 6165782B2 JP 2014558215 A JP2014558215 A JP 2014558215A JP 2014558215 A JP2014558215 A JP 2014558215A JP 6165782 B2 JP6165782 B2 JP 6165782B2
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- 239000000203 mixture Substances 0.000 title claims description 144
- 239000004065 semiconductor Substances 0.000 title claims description 92
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- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000011230 binding agent Substances 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 11
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- FWSPXZXVNVQHIF-UHFFFAOYSA-N triethyl(ethynyl)silane Chemical group CC[Si](CC)(CC)C#C FWSPXZXVNVQHIF-UHFFFAOYSA-N 0.000 description 1
- TVAVCYUNZIELEP-UHFFFAOYSA-N triethyl-[2-[1,4,8,11-tetramethyl-13-(2-triethylsilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC(C)=C2C=C3C(C#C[Si](CC)(CC)CC)=C(C=C4C(C(C)=CC=C4C)=C4)C4=C(C#C[Si](CC)(CC)CC)C3=CC2=C1C TVAVCYUNZIELEP-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Description
半導体組成物を提供することを追求する。
本発明の多環芳香族炭化水素コポリマー(以下PAHC)は、式(A)を有する少なくとも1つのヘテロアセンモノマー単位と、式(B)を有する少なくとも1つのトリアリールアミンモノマー単位との混合物を含む。
R’’’は、H、随意にフッ素化されC1〜C20を有するアルキル基、または随意にフッ素化されC2〜C30、好ましくはC5〜C20を有するアリール基を表し、
R’’’’は、Hであるか、またはC1〜C10を有する環状、直鎖状、もしくは分枝状のアルキル基であり、好ましくはHであり、
kは、0または1であり、
lは、0または1であり、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、およびR14の各々は、同一でも異なっていてもよく、独立して、水素;分枝もしくは非分枝の置換もしくは非置換C1−C40アルキル基;分枝もしくは非分枝の置換もしくは非置換C2−C40アルケニル基;分枝もしくは非分枝の置換もしくは非置換C2−C40アルキニル基;随意に置換されたC3−C40シクロアルキル基;随意に置換されたC6−C40アリール基;随意に置換されたC1−C40複素環基;随意に置換されたC1−C40ヘテロアリール基;随意に置換されたC1−C40アルコキシ基;随意に置換されたC6−C40アリールオキシ基;随意に置換されたC7−C40アルキルアリールオキシ基;随意に置換されたC2−C40アルコキシカルボニル基;随意に置換されたC7−C40アリールオキシカルボニル基;シアノ基(−CN);カルバモイル基(−C(=O)NR15R16);カルボニル基(−C(=O)−R17);カルボキシル基(−CO2R18);シアネート基(−OCN);イソシアノ基(−NC);イソシアネート基(−NCO);チオシアネート基(−SCN)もしくはチオイソシアネート基(−NCS);随意に置換されたアミノ基;ヒドロキシ基;ニトロ基;CF3基;ハロ基(Cl、Br、F、I);−SR19;−SO3H;−SO2R20;−SF5;随意に置換されたシリル基;SiH2R22基で置換されたC2−C10アルキニル基、SiHR22R23基で置換されたC2−C10アルキニル、または−Si(R22)x(R23)y(R24)z基で置換されたC2−C10アルキニルを表し;
各R22基は、分枝または非分枝の置換または非置換C1−C10アルキル基、分枝または非分枝の置換または非置換C2−C10アルキニル基、置換または非置換C2−C20シクロアルキル基、置換または非置換C2−C10アルケニル基、および置換または非置換C6−C20シクロアルキルアルキレン基からなる群より独立して選ばれ;
各R23基は、分枝または非分枝の置換または非置換C1−C10アルキル基、分枝または非分枝の置換または非置換C2−C10アルキニル基、置換または非置換C2−C10アルケニル基、置換または非置換C2−C20シクロアルキル基、および置換または非置換C6−C20シクロアルキルアルキレン基からなる群より独立して選ばれ;
R24は、水素、分枝または非分枝の置換または非置換C2−C10アルキニル基、置換または非置換C2−C20シクロアルキル基、置換または非置換C6−C20シクロアルキルアルキレン基、置換C5−C20アリール基、置換または非置換C6−C20アリールアルキレン基、アセチル基、ならびに環中にO、N、S、およびSeのうち少なくとも1つを含む置換または非置換C3−C20複素環からなる群より独立して選ばれ;
x=1または2であり;y=1または2であり;z=0または1であり;(x+y+z)=3であり;
R15、R16、R18、R19、およびR20の各々は、独立して、Hを表すか、または1つ以上のヘテロ原子を随意に含む随意に置換されたC1−C40カルビル基もしくはヒドロカルビル基を表し;
R17は、ハロゲン原子もしくはHを表すか、または、1つ以上のヘテロ原子を随意に含む随意に置換されたC1−C40カルビル基もしくはC1−C40ヒドロカルビル基を表し;
R1、R2、R3、R4、R8、R9、R10、およびR11のうちの少なくとも2つは、式(A)または(B)を有する別のモノマー単位との間の−*で表される結合であり;Ar1、Ar2、およびAr3は、同一でも異なっていてもよく、その各々は、異なる繰り返し単位に存在する場合は独立して、随意に置換されたC6−40芳香族基(単環または多環)を表し、好ましくは、Ar1、Ar2、およびAr3のうちの少なくとも1つは、少なくとも1つの極性基または極性化性の基(polarising group)で置換され、モノマー基(B)に関して、−*は、式(A)または(B)を有する別のモノマー単位との結合を表し;
好ましくは、R2=R10であり、R2とR10は、H、F、Cl、Br、I、CN、随意にフッ素化または全フッ素置換され1〜20個、好ましくは1〜8個の炭素原子を有する直鎖状または分枝状のアルキル、随意にフッ素化または全フッ素置換され1〜20個、好ましくは1〜8個の炭素原子を有する直鎖状または分枝状のアルコキシ、随意にフッ素化または全フッ素置換され6〜30個の炭素原子を有するアリールを表し、好ましくはC6F5またはCO2R’’’を表し;
R’’’は、H、随意にフッ素化されたC1〜C20アルキル基、または随意にフッ素化されたC6〜C30アリール基を表し、好ましくは、随意にフッ素化されたC6〜C20アリール基を表す。
できる。簡単にするため、トリフェニルアミンモノマーとカップリングし、ビス(トリアルキル)シリルで置換されたペンタセンを表示している(さらなる置換は表示していない。当業者であれば、どうすればこれを上記構造に一般化できるかを理解している)。カップリング反応は、好ましくは、山本型カップリング(塩化ニッケル、亜鉛、2,2’−ビピリジル、トリフェニルホスフィン、およびジメチルアセトアミドを使用)であるが、鈴木カップリングも可能である。ただし、この場合、得られる半導体ポリマーからボロン酸エステル(boronic ester)を除去することが好ましい。
それぞれ水素添加および/または加水分解により置換される)。
X’は、ハロゲン原子または環状ホウ酸エステル基(cyclic borate group)であり;
Z’は、ハロゲン原子である。
び/またはLR 8889(登録商標)として提供)(すべてBASF社から入手可能)
、トリアクリル酸トリメチロールプロパン、トリアクリル酸プロポキシル酸グリセロール(glycerol propoxylate triacrylate)、ペンタアクリル酸ジペンタエリトリトール、ヘキサアクリル酸ジペンタエリトリトール、エトキシ化テトラアクリル酸ペンタエリトリトール(サートマー社からSR494(登録商標)として提供)、ならびにこれらの混合物および組み合わせが挙げられる。本発明の組成物に反応性希釈剤を添加する場合は、所望される任意の量または有効量の反応性希釈剤が添加され、一実施形態では、少なくとも約1重量パーセントの担体、少なくとも約35重量パーセントの担体、約98重量パーセント以下の担体、約75重量パーセント以下の担体が添加されるが、希釈剤の量はこれらの範囲の外にあってよい。
1重量%未満含有し、より好ましくは実質的にまったく含有しない。好適な一実施形態では、誘電率の測定は、国際公開第2004/102690号で開示されている方法、または本明細書に開示される方法を用いて行い、好ましくは、本明細書に開示される方法を用いて行う。
以下、(A)として上記で定義したヘテロアセンモノマー単位の好ましい特性をいくつか挙げる。
R6とR13は、トリアルキルシリルエチニル基、−C≡C−SiR22R23R24であり、ここでR22、R23、およびR24は、独立してC1−C4アルキルまたはC2−C4アルケニルを表し;
R1、R4、R8、およびR11は、水素;分枝もしくは非分枝の非置換C1−C4アルキル基;C1−C6アルコキシ基;およびC6−C12アリールオキシ基からなる群より独立して選ばれ;
ただし、R2/R3とR9/R10の各ペアのうち少なくとも1つは、式(A)、(A1)、または(B)を有する別のモノマー単位との−*で表される結合であり;
kとlは、独立して0または1であり、好ましくは、kとlの両方とも0である。
いる方法を、本発明で使用するヘテロアセン化合物の合成に使用することができる。本発明のPAHCの高誘電率類似体は、国際公開第2012/160383号および国際公開第2012/164282号に従って作製することができる。
以下、(B)として上記で定義したトリアリールアミンモノマー単位の好ましい特性をいくつか挙げる。
指す)。好ましくは、Ar1、Ar2、およびAr3のうちの少なくとも1つは、1つ、2つ、3つ、または4つ、より好ましくは1つ、2つ、または3つ、より好ましくは1つまたは2つ、好ましくは1つの極性基またはより極性化性の基で置換される。
ばれ、Ar1、Ar2、およびAr3のうちの少なくとも1つは、同一の1つまたは2つの極性基またはより極性化性の基で置換される。
本発明の第1の態様による有機半導体組成物は、コポリマー組成物を含み、この組成物の1000Hz時の誘電率は、1.5超であり、より好ましくは3.4超、さらにより好ましくは1.5〜6.5、さらにより好ましくは3〜6.5、より好ましくは3.0〜5.0、さらにより好ましくは3.4〜4.5である。
ば、組成物中に界面活性剤が存在する場合、この界面活性剤は、好ましくは組成物総重量に対して0超〜約1.0重量%の量で存在し、より典型的には約0.001〜約0.5重量%の量で存在する。
Appl. Phys., 1994, Volume 75, page 7954および国際公開第2005/055248号に開示されている手法を用いて行ってよく、好ましくは国際公開第2005/055248号に記載の手法を用いて行う。
本発明の有機半導体組成物を様々な基板に堆積させて、有機半導体層を形成することができる。
(i)本発明の有機半導体組成物と、溶媒とを混合して、半導体層配合物を形成すること。
(ii)上記配合物を基板に堆積させること。および
(iii)随意に溶媒を除去して、有機半導体層を形成すること。
定することができる。このASTM方法に記載の通り、種々の溶媒に材料を添加する。
キシレン、m−キシレン、p−キシレン、メシチレン、ブロモメシチレン、アニソール、ブロモアニソール、ブロモベンゼン、テトラリン、o−キシレン、1,4−ジオキサン、メチルエチルケトン、γ−ブチロラクトン、シクロヘキサノン、モルホリン、N−メチルピロリドン、酢酸エチル、酢酸n−ブチル、ジメチルホルムアミド、ジメチルアセトアミド、デカリン、これらのうちの2つ以上の混合物が挙げられるが、これらに限定されない。好ましくは、塩素化溶媒は一切使用しない。
わち時間的制約なしに)完全に自力で蒸発させてもよく、蒸発速度を制御する目的で条件を管理してもよい。パッキング不良を最少化する目的で、堆積層を覆うことにより蒸発速度を低下させながら溶媒を蒸発させてよい。このような条件から、比較的結晶化度の高い半導体層を得ることができる。
加えて、本発明は、本発明の有機半導体組成物を含む電子デバイスを提供する。本発明の組成物を、例えば半導体層または半導体膜の形態で使用してよい。加えて、本発明は、好ましくは、本発明の有機半導体層を含む電子デバイスを提供する。
一般
本発明で使用するヘテロアセンモノマーに関して、1つの異性体が表示されているが、本発明は、純粋なシス異性体、純粋なトランス異性体、およびシス異性体とトランス異性体の混合物に適用される。
上の置換基が結合しているアルキニル基であって、この1つ以上の置換基の各々は、炭素と水素を除く1つ以上の原子を単独で含有する(例えばF等のハロゲン)か、炭素原子と組み合わせて含有し(例えばシアノ基)、かつ/または水素原子と組み合わせて含有する(例えばヒドロキシル基、カルボン酸基、シリル基)一価部分を含む、アルキニル基をいう。
ポリマー結合剤の粘度を低下させ、1000〜2000rpmのスピン速度範囲でスピンコーティングしたときに1ミクロン未満の厚さの膜が得られるようにするため、ポリマー結合剤をテトラリンで希釈した。ITOがコーティングされた洗浄済みの1×1インチのガラス基板上に、ポリマー結合剤溶液を500rpmで10秒間スピンコーティングし、続いて1500rpmで30秒間スピンコーティングした。
浸し、超音波浴(水温65℃超)に入れて脱イオン水で洗浄し、脱イオン水に浸し、超音波浴(水温65℃超)に入れて再度、脱イオン水で洗浄し、イソプロピルアルコールに浸し、超音波浴(水温65℃超)に入れて、スピン乾燥させた。
3030表面形状測定器(ニューヨーク州プレーンビューのVeecoから入手可能)
を用いて3か所の厚さを測定し、平均値を求めた。続いて、この値を用いてポリマー結合剤の誘電率を算出した。
ョンを用いて静電容量を測定した。ITO背面電極と外部プローブ電極間の電気接触を改善するため、導電性の銀ペーストを塗布した。外部環境の影響を確実に最小化するため、測定試料を金属板上の金属ボックスに入れた。
C=ε×εo×(A/d)
シャドウマスクを用いた熱蒸着プロセス、またはフォトリソグラフィにより、基板(ガラス基板またはPEN等のポリマー基板)にAuソースドレイン電極をパターニングする(Auを堆積させる前に、CrまたはTiの接着層を基板に堆積させる)。O2プラズマ洗浄プロセスを用いて、Au電極を随意に洗浄してもよい。次に、結合剤中の有機半導体溶液をスピンコーティングにより塗布する(試料を溶液で満たしてから、基板を500rmpで5秒間、さらに1500rpmで1分間回転させる)。次に、コーティングした基板をホットステージ上で風乾する。次に、誘電体材料(例えばFC−43に溶解した3重量%のPTFE−AF1600、シグマアルドリッチ カタログ番号469610)をス
ピンコーティングにより基板に塗布した(試料を満たしてから、500rpmで5秒間、さらに1500rpmで30秒間回転させる)。次に、基板をホットステージ上で風乾した(100℃で1分間)。次に、シャドウマスクを用いた蒸発により、ゲート電極(Au)をチャンネル領域上で画定する。
ションを設置することにより、結合剤に関するOTFTの移動度を特性評価する。ソースドレイン電圧(VDS)を−2V(線形)または−40V(飽和)に設定し、ゲート電圧(VG)を+20Vから−60Vまで走査する。ドレイン電流を測定し、相互コンダクタンスから移動度を算出する。
生成物(1)を得た(17.58g、72%)。1H NMR(CDCl3,600MH
z)7.24(1H,d,J=5.2Hz),7.10(1H,d,J=5.2Hz),6.36(1H,s),6.05(1H,s),4.15−4.08(4H,m)4.0
2−3.98(4H,m)
8.76mL、96.9mmol、1.3当量)を滴下添加して、溶液を1時間撹拌した。次に、N−ブロモスクシンイミド(アルドリッチB81255、16.11g、90.5mmol、1.2当量)を15分かけて何回かに分けて添加した。次に、反応混合物を撹拌しながら一晩置いて、室温まで温めた。次に水(200mL)をゆっくり添加した。次に、混合物をジエチルエーテル(2×250mL)で抽出し、抽出物を水(3×500mL)で洗浄した。有機抽出物をMgSO4上で乾燥させ、ろ過し、真空中で濃縮して、淡黄色の油(14.59g)を得た。この生成物を3MのHCl(131mL)に添加し、1時間、加熱還流した。混合物を室温まで冷ましてから、ジエチルエーテル(3×750mL)で抽出した。合わせた有機抽出物をMgSO4上で乾燥させ、ろ過し、真空中で濃縮して、茶色の半固形物(7.38g)を得た。次に、この生成物をドライカラムクロマトグラフィー(勾配溶出:ヘプタン;10%−50% EtOAc:ヘプタン)で精製
して、黄色の固体状の生成物(2)を得た(1.93g、12%)。1H NMR(CD
Cl3,300MHz)10.38(1H,s),10.26(1H,s),7.60(1H,s)
50℃まで加熱し、1時間撹拌した。次に、反応混合物を10℃未満まで冷却し、ろ過により固形物を回収した。ろ過ケークをメタノール(50mL)と水(50mL)で洗浄して、暗赤色の固形物(1.94g)を得た。次に、この固形物をフラッシュカラムクロマトグラフィー(勾配溶出:ヘプタン;10%−50% DCM:ヘプタン)で精製して、
赤色の結晶性固体(1.31g)を得た。この生成物をさらにフラッシュカラムクロマトグラフィー(勾配溶出:ヘプタン;10%−50% DCM:ヘプタン)で精製して、赤
色の結晶性固体(1.05g)を得た。次に、この生成物をMeOH(50mL)中でスラリー状にし、ろ過により固形物を回収した。次に生成物(4)を真空オーブン中で乾燥させた(0.89g、1.23mmol、37%)。1H NMR(300MHz,CD
Cl3)8.96−8.93(8H,m),7.47−7.45(4H,m),1.27−1.20(36H,m),0.95−0.86(24H,m) MS(ASAP)m/
z725(M+,100%)
z,CDCl3)7.25−6.88(13H,m),2.35(3H,s),2.02(3H,s)
10181852、2.5Mヘキサン溶液、22.3mL、55.7mmol、2.4
当量)を滴下添加した後、反応混合物を1時間撹拌した。2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン(シグマアルドリッチ417149、11.22g、60.3mmol、2.6当量)を滴下添加した。次に、反応混合物を一晩置いて室温まで温めた。水(60mL)を添加し、混合物を20分間撹拌した。次に、混合物をジクロロメタン(3×60mL)で抽出した。合わせた有機抽出物をMgSO4上で乾燥させ、ろ過し、真空中で濃縮して、黄色の発泡体(11.27g)を得た。次に、この生成物をドライカラムクロマトグラフィー(勾配溶出5%−10% EtOA
c:ヘプタン)で精製して、無色の固形物(6.65g)を得た。この固形物をMeCN/THFから再結晶化させて、無色の結晶性固体状の生成物(7)を得た(6.14g、11.7mmol、50%)。1H NMR(500MHz,CDCl3)7.63(4
H,d,J=8.3Hz),7.06−6.99(3H,m),6.96(4H,d,J=8.3Hz),2.34(3H,s),1.96(3H,s),1.32(24H,s)MS(ASAP)m/z 525(M+,100%)
2,8−ジブロモ−5,11−ビス(トリエチルシリルエチニル)アントラ[2,3−b:6,7−b’]ジチオフェン/2,8−ジブロモ−5,11−ビス(トリエチルシリルエチニル)アントラ[2,3−b:7,6−b’]ジチオフェン(4)(0.37g、0.49mmol、0.5当量)、N,N−ビス(4−ブロモフェニル)−2,4−ジメチルフェニルアミン(6)(0.21g、0.49mmol、0.5当量)、N,N−ビス[4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル]−2,4−ジメチルフェニルアミン(7)(0.52g、0.98mmol、1.0当量)、テトラキス(トリフェニルホスフィン)パラジウム(0)(Acros
12065360、0.034g、0.03mmol、0.03当量)、2M K2CO
3(2.9mL、5.88mmol、6当量)、およびトルエン(42mL)中のAliquat(登録商標)336(シグマアルドリッチ205613、6滴)の混合物を、窒素流を30分間溶液に通すことにより脱ガスした。次に、混合物を加熱環流した。1時間後、HPLCによりオリゴマーの存在を確認した。反応混合物を静置して50℃まで冷ました。反応混合物を撹拌しながらMeOH(135mL)に注いだ。30分後、沈降した
固形物をブフナー漏斗を用いて吸引ろ過して、赤茶色の固形物(0.79g)を得た。ドライカラムクロマトグラフィー(溶出液:THF)により、この固形物を精製した。生成物を含有する画分を真空中で濃縮して、赤茶色の固形物(0.63g)を得た。フラッシュカラムクロマトグラフィー(溶出液:THF)により、再度この固形物を精製した。生成物を含有する画分を真空中で濃縮して、赤茶色の固形物(0.63g)を得た。この固形物をTHF(20mL)に溶かし、メタノール(60mL)に注いだ。沈殿した固形物を、ブフナー漏斗を用いた吸引ろ過により回収した。次に、得られた固形物を真空オーブン内で乾燥させて、赤茶色の粉末状の生成物(0.48g)を得た(75% トリアリー
ルアミン:25% TIPS ADT)。この生成物の特性は次のように評価された:GPC Mn=4669ダルトン、Nav=14。
販の2,4−ジメチルポリトリアリールアミン(ハイフォースリサーチ社の2,4−ジメチルポリトリアリールアミンポリマーのコードはPE3)を我々の誘電率試験で測定したところ、結合剤PE3の誘電率は2.98であった。)
TES−アントラセンジチオフェン−2,4−ジメチルトリアリールアミンのコポリマーであるPAHC(1)と、ポリアセン1(1,4,8,11−テトラメチル−6,13−ビス(トリエチルシリルエチニル)ペンタセン)(重量比70:30)を、1,2,3,4−テトラヒドロナフタレン中で全固形物1.7重量%で溶解させた。これを、上記の方法に従ってOTFTの有機半導体層としてコーティングした。この配合物をパターニング済みAuソース/ドレイン電極(イソプロピルアルコール中の10mMペンタフルオロベンゼンチオール溶液で処理された50nm厚Au)にスピンコーティングした(500rpmで5秒、次いで1500rpmで60秒)。上部にフルオロポリマー誘電体Cytop(Asahi Chemical Co.)をスピンコーティングした(500rpmで5秒、次いで1500rpmで20秒)。最後に、シャドウマスク蒸発によりAuゲート電極を堆積させた。
Claims (21)
- 下記の式(A)を有する少なくとも1つのヘテロアセンモノマー単位(A)と、下記の式(B)を有する少なくとも1つのモノマー単位(B)との混合物を含む、多環芳香族炭化水素コポリマー(PAHC)であって、
前記式(A)中、kとlは、独立して0または1であり;Y 1 =Y 2 =Sであり;R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 は表1に示したケース1〜6より選ばれ;ただし、R 2 及びR 3 とR 9 及びR 10 のペアのうち一方は、別のモノマー単位との−*で表される結合であり;
前記ヘテロアセンモノマー単位(A)は、純粋なシス異性体もしくは純粋なトランス異性体、またはシス異性体とトランス異性体の混合物であってよく;
前記モノマー単位(B)は表2より選ばれる、PAHC。
- 前記コポリマー中のすべてのモノマー単位(A)および(B)の総計に対して、少なくとも20〜40%のモノマー(A)と、少なくとも60〜80%のモノマー(B)とを含む、請求項1に記載のPAHC。
- k=0かつl=0である、請求項1または2に記載のPAHC。
- 前記コポリマーの数平均分子量(Mn)が500〜100,000である、請求項1〜3のいずれかに記載のPAHC。
- 前記コポリマーは、1000Hz時の誘電率が1.5超である、請求項1〜4のいずれかに記載のPAHC。
- 前記コポリマーは1000Hz時の誘電率が3.4〜8.0の半導体コポリマーである、請求項5に記載のPAHC。
- モノマー単位(B)において、C 1 〜C 6 アルコキシ基がメトキシ基またはエトキシ基である、請求項1〜6のいずれかに記載のPAHC。
- モノマー単位(B)において、C 1 〜C 6 アルコキシ基の全てがメトキシ基またはエトキシ基である、請求項1〜6のいずれかに記載のPAHC。
- 下記の1つ以上のモノマー(C)、(D)、(D’)、および/または(E)をさらに含む、請求項1〜8のいずれかに記載のPAHC。
ルキル基;分枝もしくは非分枝の置換もしくは非置換C 2 −C 40 アルケニル基;分枝もし
くは非分枝の置換もしくは非置換C 2 −C 40 アルキニル基;随意に置換されたC 3 −C 40 シクロアルキル基;随意に置換されたC 6 −C 40 アリール基;随意に置換されたC 1 −C 40 複素環基;随意に置換されたC 1 −C 40 ヘテロアリール基;随意に置換されたC 1 −C 40 アルコキシ基;随意に置換されたC 6 −C 40 アリールオキシ基;随意に置換されたC 7 −C 40 アルキルアリールオキシ基;随意に置換されたC 2 −C 40 アルコキシカルボニル基;随意に
置換されたC 7 −C 40 アリールオキシカルボニル基;シアノ基(−CN);カルバモイル
基(−C(=O)NR 15 R 16 );カルボニル基(−C(=O)−R 17 );カルボキシル基(−CO 2 R 18 );シアネート基(−OCN);イソシアノ基(−NC);イソシアネー
ト基(−NCO);チオシアネート基(−SCN)もしくはチオイソシアネート基(−NCS);随意に置換されたアミノ基;ヒドロキシ基;ニトロ基;CF 3 基;ハロ基(Cl
、Br、F、I);−SR 19 ;−SO 3 H;−SO 2 R 20 ;−SF 5 ;随意に置換されたシ
リル基;−SiH 2 R 22 基で置換されたC 2 −C 10 アルキニル基、−SiHR 22 R 23 基で置換されたC 2 −C 10 アルキニル、または−Si(R 22 ) x (R 23 ) y (R 24 ) z 基で置換されたC 2 −C 10 アルキニル部分を表し;
各R 22 基は、分枝または非分枝の置換または非置換C 1 −C 10 アルキル基、分枝または
非分枝の置換または非置換C 2 −C 10 アルキニル基、置換または非置換C 2 −C 20 シクロアルキル基、置換または非置換C 2 −C 10 アルケニル基、および置換または非置換C 6 −C 20 シクロアルキルアルキレン基からなる群より独立して選ばれ;
各R 23 基は、分枝または非分枝の置換または非置換C 1 −C 10 アルキル基、分枝または
非分枝の置換または非置換C 2 −C 10 アルキニル基、置換または非置換C 2 −C 10 アルケニル基、置換または非置換C 2 −C 20 シクロアルキル基、および置換または非置換C 6 −C 20 シクロアルキルアルキレン基からなる群より独立して選ばれ;
R 24 は、水素、分枝または非分枝の置換または非置換C 2 −C 10 アルキニル基、置換ま
たは非置換C 2 −C 20 シクロアルキル基、置換または非置換C 6 −C 20 シクロアルキルアルキレン基、置換C 5 −C 20 アリール基、置換または非置換C 6 −C 20 アリールアルキレン基、アセチル基、ならびに環中にO、N、S、およびSeのうち少なくとも1つを含む置換または非置換C 3 −C 20 複素環からなる群より独立して選ばれ;
x=1または2であり;y=1または2であり;z=0または1であり;(x+y+z)=3であり;
R 15 、R 16 、R 18 、R 19 、およびR 20 の各々は、独立して、Hを表すか、または1つ以上のヘテロ原子を随意に含む随意に置換されたC 1 −C 40 カルビル基もしくはヒドロカル
ビル基を表し;
R 17 は、ハロゲン原子もしくはHを表すか、または、1つ以上のヘテロ原子を随意に含む随意に置換されたC 1 −C 40 カルビル基もしくはC 1 −C 40 ヒドロカルビル基を表し;
n’=1〜3である。) - 前記コポリマー中の全モノマー単位の総重量に対して、モノマー(A)は少なくとも20重量%の量で存在し、モノマー(B)は少なくとも60重量%の量で存在し、残り部分はモノマー(C)、(D)、(D’)、および/または(E)で構成される、請求項9に記載のPAHC。
- 請求項1〜10のいずれかに記載のPAHCと、ポリアセン小分子と、を含む有機半導体組成物であって、該PAHCの1000Hz時の誘電率は3.4〜8.0である、有機半導体組成物。
- 請求項1〜10のいずれかに記載のPAHCと、ポリアセン小分子と、を含む有機半導体組成物であって、該PAHCの1000Hz時の誘電率は3.4〜4.5である、有機半導体組成物。
- 請求項1〜10のいずれかに記載の多環芳香族炭化水素コポリマー(PAHC)を含み、1000Hz時の誘電率が3〜6.5である、有機半導体組成物。
- 1000Hz時の誘電率が3.4〜8である有機結合剤を含む、請求項13に記載の有機半導体組成物。
- 少なくとも0.5cm 2 V −1 s −1 の電荷移動度値を有する、請求項11〜14のいずれかに記載の有機半導体組成物。
- 2〜5.0cm 2 V −1 s −1 の電荷移動度値を有する、請求項15に記載の有機半導体組成物。
- 請求項1〜16のいずれかに記載のPAHCまたは有機半導体組成物を含む、有機半導体層。
- 請求項1〜17のいずれかに記載のPAHC、有機半導体組成物、または半導体層を含
む、電子デバイス。 - 有機薄膜トランジスタ(OTFT)、有機発光ダイオード(OLED)、光検出器、有機光起電力(OPV)電池、センサー、レーザー、記憶素子、および論理回路から選ばれる、請求項18に記載の電子デバイス。
- 請求項1〜16のいずれかに記載のPAHCまたは有機半導体組成物を含む、インク。
- 請求項1に記載の多環芳香族炭化水素コポリマー(PAHC)の製造方法であって、下記の構造(A’)から選ばれる少なくとも1つのヘテロアセンモノマーと、アリールアミンモノマー(B’)とを含有する組成物を共重合させることを含む、製造方法。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、およびR14の各々は、請求項1と同じであり;
kとlは、独立して0または1であり;
R ’a 、R ’b 、R ’c 、R ’d 、R ’e の各々は、請求項1と同じであり;
X’は、ハロゲン原子または環状ホウ酸エステル基(cyclic borate group)であり;
Z’は、ハロゲン原子である。)
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