JP2019505986A - 非芳香族環を含むケトンを含む調合物 - Google Patents
非芳香族環を含むケトンを含む調合物 Download PDFInfo
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- JP2019505986A JP2019505986A JP2018530159A JP2018530159A JP2019505986A JP 2019505986 A JP2019505986 A JP 2019505986A JP 2018530159 A JP2018530159 A JP 2018530159A JP 2018530159 A JP2018530159 A JP 2018530159A JP 2019505986 A JP2019505986 A JP 2019505986A
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
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- 239000002096 quantum dot Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 238000013341 scale-up Methods 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
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- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
有機発光素子(OLED)は、長い間、真空堆積プロセスにより製造されてきた。インクジェット印刷等の他の技術が、費用節約とスケールアップの可能性等の利点の故に、最近全面的に研究されてきた。多層印刷における主な挑戦の一つは、良好な素子性能と相まって、基板上へのインクの均質な堆積を得るための関連するパラメータを同定し調整することである。特に、材料の溶解度、溶媒の物理的パラメータ(表面張力、粘度、沸点等)、印刷技術、加工条件(大気、窒素、温度等)と乾燥パラメータが、画素パターンとその結果の素子性能に劇的に影響し得る特徴である。
これらの特徴の中でも、溶媒の選択が重要である。例として、US2010/0200841は、有機発光ダイオードにおける活性層を形成するためのインク組成物を記載している。組成物は、少なくとも一つの芳香族ケトンを含むケトン系溶媒系を含む。US 2011/0220886 A1は、脂肪族環もしくは芳香族環とアントラセン誘導体を有する溶媒を含む有機エレクトロルミッセンス材料組成物を記載している。例として、インデンもしくはインダンが、有機エレクトロルミッセンス材料組成物における溶媒として使用された。
多くの溶媒が、インクジェット印刷のために有機電子素子において提案されてきた。しかしながら、堆積と乾燥プロセスの期間中に役割を果たす多くの重要なパラメータの数が、溶媒の選択を極めて挑戦的なものにしている。さらなる挑戦は、先行技術の溶媒は、溶液調製のために多くの努力が必要とされるように、極めてゆっくりと機能性化合物を溶解することである。このように、インクジェット印刷による堆積のために使用される半導体等の有機機能性材料を含む調合物は、未だ改善される必要がある。本発明の一つの目的は、制御された堆積が、良好な層特性と性能を有する有機半導体層を形成することを可能とする有機半導体材料の調合物を提供することである。本発明のさらなる目的は、インクジェット印刷法に使用される時の基板上へのインク液滴の均一な適用を可能とし、それにより良好な層特性と性能を付与する有機半導体の調合物を提供することである。本発明の別の目的は、インクジェット印刷による堆積を使用する場合に、均一な膜形成を実現するために、有機半導体材料を迅速に溶解し、適切な粘度、表面張力と沸点を有する溶媒を提供することである。
本発明の上記目的は、少なくとも一つの有機機能性材料と少なくとも一つのケトン溶媒とを含み、前記ケトン溶媒は、一般式(I)によるケトンを含むことを特徴とする調合物により解決される:
R1およびR2は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくは分岐あるいは環式アルキル基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR3-、-CONR3-、-C=O-、-C=S-、-(C=NR3)-、-P(=O)(R3)-、-C(=O)O-、-C(=O)NR3-、-HC=CH-、-R3C=CR3-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上のR3基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であって;複数の置換基R3は、同じ環上もしくは2種の異なる環上の何れかで、順に一緒になって、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してよく;
R3は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR4-、-CONR4-、-C=O-、-C=S-、-(C=NR4)-、-P(=O)(R4)-、-C(=O)O-、-C(=O)NR4-、-HC=CH-、-R4C=CR4-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
R4は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
ただし、残基R1およびR2の少なくとも一つは、非芳香族環を含む。
本発明者は、OLED調合物のための溶媒として、非芳香族環を含むケトンの使用が、効率的なインク堆積を可能とし、良好な層特性と極めて良好な性能を有する機能性材料の均一でよく制御された有機層を形成することを驚くべきことに見出した。さらに、調合物の調製のために使用される本溶媒は、迅速で簡単な方法で機能性材料を溶解する。さらに、本発明による調合物における機能性材料の溶解度は、驚く程高い。
本発明は、少なくとも一つの有機機能性材料と少なくとも一つのケトン溶媒とを含み、前記ケトン溶媒は、一般式(I)によるケトンを含むことを特徴とする調合物に関する:
R1およびR2は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくは分岐あるいは環式アルキル基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR3-、-CONR3-、-C=O-、-C=S-、-(C=NR3)-、-P(=O)(R3)-、-C(=O)O-、-C(=O)NR3-、-HC=CH-、-R3C=CR3-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上のR3基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であって;複数の置換基R3は、同じ環上もしくは2種の異なる環上の何れかで、順に一緒になって、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してよく;
R3は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR4-、-CONR4-、-C=O-、-C=S-、-(C=NR4)-、-P(=O)(R4)-、-C(=O)O-、-C(=O)NR4-、-HC=CH-、-R4C=CR4-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
R4は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
ただし、残基R1およびR2の少なくとも一つは、非芳香族環を含む。
好ましい1態様では、一般式(I)によるケトン化合物のR1および/またはR2に含まれる非芳香族環は、環式炭化水素残基もしくはハロゲン化環式炭化水素残基、好ましくは、飽和環式炭化水素残基である。好ましくは、一般式(I)によるケトン化合物のR1およびR2に含まれる非芳香族環は、ハロゲン以外の如何なるヘテロ原子も含まない。
HOMO(eV)=((HEh*27.212)−0.9899)/1.1206
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
本出願の目的のために、これらの値は、材料夫々のHOMOおよびLUMOエネルギー準位とみなすべきである。
DCyは、出現毎に同一であるか異なり、それを介して環式の基が金属に結合する、少なくとも一つのドナー原子、好ましくは、窒素、カルベンの形態の炭素もしくは燐を含む環式の基であり、順に一以上の置換基Raを有してよく、基DCyとCCyは、共有結合を介して互いに結合し、
CCyは、出現毎に同一であるか異なり、それを介して環式の基が金属に結合する炭素原子を含む環式の基であり、順に一以上の置換基Raを有してよく、
Aは、出現毎に同一であるか異なり、モノアニオン性二座キレートリガンド、好ましくは、ジケトネートリガンドであり、
Raは、出現毎に同一であるか異なり、F、Cl、Br、I、NO2、CN、1〜20個の炭素原子を有する直鎖、分岐あるいは環式アルキルもしくはアルコキシ基(1以上の隣接しないCH2基は、-O-、-S-、-NRb、-CONRb、-CO-O-、-C=O-、-CH=CH-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、Fで置き代えられてよい。)、または、1以上のRc基により置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;および複数の置換基R18は、同じ環上もしくは異なる環上の何れかで、順に一緒に、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく;
Rbは、出現毎に同一であるか異なり、1〜20個の炭素原子を有する直鎖、分岐あるいは環式アルキルもしくはアルコキシ基(1以上の隣接しないCH2基は、-O-、-S-、-CO-O-、-C=O-、-CH=CH-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、Fで置き代えられてよい。)、または、1以上のRc基により置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり、
Rcは、出現毎に同一であるか異なり、1〜20個の炭素原子を有する直鎖、分岐あるいは環式アルキルもしくはアルコキシ基(1以上の隣接しないCH2基は、-O-、-S-、-CO-O-、-C=O-、-CH=CH-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、Fで置き代えられてよい。)である。
4514 A1)、金属錯体/ポリシラン化合物およびチオフェン、ベンゾチオフェンおよびジベンゾチオフェン誘導体を含む。
群1:正孔注入および/または正孔輸送特性を生成することができる構造要素;
群2:電子注入および/または電子輸送特性を生成することができる構造要素;
群3:群1および群2に関して記載される特性を組み合わせた構造要素;
群4:発光特性、特に、燐光発光基を有する構造要素;
群5:いわゆる一重項状態から三重項状態への遷移を改善する構造要素;
群6:得られたポリマーのモルホロジーまた発光色に作用する構造要素;
群7:典型的には骨組として使用される構造要素。
Ar1は、各場合に、相異なる反復単位に対して、同一であるか異なり、単結合または随意に置換されてよいモノ環式あるいはポリ環式のアリール基であり;
Ar2は、各場合に、相異なる反復単位に対して、同一であるか異なり、随意に置換されてよいモノ環式あるいはポリ環式のアリール基であり;
Ar3は、各場合に、相異なる反復単位に対して、同一であるか異なり、随意に置換されてよいモノ環式あるいはポリ環式のアリール基であり;
mは、1,2または3である。
Raは、出現毎に同一であるか異なり、H、置換もしくは非置換芳香族もしくは複素環式芳香族基、アルキル、シクロアルキル、アルコキシ、アラルキル、アリールオキシ、アリールチオ、アルコキシカルボニル、シリルもしくはカルボキシル基、ハロゲン原子、シアノ基、ニトロ基またはヒドロキシ基であり;
rは、0、1、2、3または4であり、および
sは、0、1、2、3、4または5である。
T1およびT2は、チオフェン、セレノフェン、チエノ[2,3-b]チオフェン、チエノ[3,2-b]チオフェン、ジチエノチオフェン、ピロールおよびアニリンから独立して選択され、ここで、これらの基は1以上の基Rbにより置換されてよく;
Rbは、ハロゲン、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X、-C(=O)R0、NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF3、随意に置換されてよく、1以上のヘテロ原子を随意に含んでよい1〜40個の炭素原子を有する随意に置換されたシリル、カルビルもしくはヒドロカルビル基から出現毎に独立して選ばれ;
R0およびR00は、夫々独立して、H、随意に置換されてよく、1以上のヘテロ原子を随意に含んでよい1〜40個の炭素原子を有する随意に置換されたカルビルもしくはヒドロカルビル基であり;
Ar7およびAr8は、互いに独立して、随意に置換されてよく、隣接するチオフェンもしくはセレノフェン基の一つもしくは両方の2,3-位で随意に結合してよいモノ環式あるいはポリ環式のアリールもしくはヘテロアリール基であり;
cおよびeは、互いに独立して、0、1、2、3または4であり、ここで、1<c+e≦6であり;
dおよびfは、互いに独立して、0、1、2、3または4である。
A、BおよびB'は、夫々、相異なる反復単位に対して、同一であるか異なり、-CRcRd-、-NRc-、-PRc-、-O-、-S-、-SO-、-SO2-、-CO-、-CS-、-CSe-、-P(=O)Rc-、-P(=S)Rc-および-SiRcRd-から好ましくは選ばれる2価基であり;
RcおよびRdは、出現毎に同一であるか異なり、H、ハロゲン、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X、-C(=O)R0、-NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF3、随意に置換されてよく、1以上のヘテロ原子を含んでよい1〜40個の炭素原子を有する随意に置換されたシリル、カルビルもしくはヒドロカビル基であり;ここで、基RcおよびRdは、それらが結合するフルオレン基と共にスピロ基を随意に形成してよく;
Xは、ハロゲンであり;
R0およびR00は、夫々、独立して、H、随意に置換されてよく、1以上のヘテロ原子を含んでよい1〜40個の炭素原子を有する随意に置換されたカルビルもしくはヒドロカビル基であり;
gは、各場合に、独立して、0または1であり、hは、各場合に、独立して、0または1であり、ここで、副単位中のgとhの合計は、好ましくは、1であり;
mは、1以上の整数であり;
Ar1およびAr2は、互いに独立して、随意に置換されてよく、インデノフルオレン基の7,8-位もしくは8,9-位で随意に結合してよいモノ環式あるいはポリ環式のアリールもしくはヘテロアリール基であり;
aおよびbは、互いに独立して、0または1である。
Lは、H、ハロゲンまたは随意にフッ素化された1〜12個のC原子を有する直鎖もしくは分岐アルキルもしくはアルコキシ基であり、好ましくは、H、F、メチル、i-プロピル、t-ブチル、n-ペントキシまたはトリフルオロメチルであり、および、
L'は、は随意にフッ素化された1〜12個のC原子を有する直鎖もしくは分岐アルキルもしくはアルコキシ基であり、好ましくは、n-オクチルまたはn-オクチルオキシである。
本発明は、さらに、ケトン溶媒、随意のさらなる溶媒と少なくとも一つの有機機能性材料とを混合することによる、電子素子の機能層の製造のために用いることができる本発明による調合物の製造方法に関する。
1.本発明による調合物を使用して得ることができる電子素子は、通常の方法を使用して得られる電子と比べて、極めて高い安定性と極めて長い寿命を呈する。
2.本発明による調合物を使用して得ることができる電子素子は、高い効率、特別に高い輝度効率と高い外部量子効率を呈する。
3.本発明による調合物は、通常の方法を使用して加工することができ、それにより、費用優位性を実現することもできる。
4.本発明による調合物を用いる有機機能性材料は、如何なる特別な制約を受けることなく、本発明のプロセスを包括的に用いることを可能とする。
5.本発明の調合物を使用して得ることができる層は、特に、層の均一性に関して、優れた品質を示す。
6.本発明による調合物は、通常の方法を使用して極めて迅速に簡単な方法で加工することができ、それにより、費用優位性を実現することもできる。
7.有機機能性材料は、本発明による調合物のいて、改善された溶解度を示す。
製造プロセスの説明
事前に構造化されたITOとバンク材料とで被覆したガラス基板を、イソプロパノールでの超音波処理と、その後の脱イオン水での超音波処理を用いて洗浄し、次いでエアガンを使用して乾燥させ、その後、2時間、230℃で、ホットプレート上でアニールする。
例1
インクジェット印刷されたOLED素子を、発光層用の溶媒としてジシクロヘキシルケトンを使用して、印刷層と共に調製する。画素化したOLED素子の構造は、ガラス/ITO/HIL(40nm)/HTM(20nm)/EML(60nm)/HBL(10nm)/ETL(40nm)/Alであり、これによりバンクを基板上に事前に製造し、画素化した素子を形成する。この場合、緑色発光材料を20mg/ml濃度でジシクロヘキシルケトンに溶解した。
インクジェット印刷されたOLED素子を、発光層用の溶媒として3-フェノキシトルエンを使用して、印刷層と共に調製する。画素化したOLED素子の構造は、ガラス/ITO/HIL(30nm)/HTM(20nm)/EML(60nm)/HBL(10nm)/ETL(40nm)/Alであり、これによりバンクを基板上に事前に製造し、画素化した素子を形成する。この場合、緑色発光材料を20mg/ml濃度で3-フェノキシトルエンに溶解した。
Claims (18)
- 少なくとも一つの有機機能性材料と少なくとも一つのケトン溶媒とを含み、前記ケトン溶媒は、一般式(I)によるケトンを含むことを特徴とする調合物:
R1およびR2は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくは分岐あるいは環式アルキル基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR3-、-CONR3-、-C=O-、-C=S-、-(C=NR3)-、-P(=O)(R3)-、-C(=O)O-、-C(=O)NR3-、-HC=CH-、-R3C=CR3-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上のR3基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であって;複数の置換基R3は、同じ環上もしくは2種の異なる環上の何れかで、順に一緒になって、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してよく;
R3は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の隣接しないCH2基は、-O-、-S-、-NR4-、-CONR4-、-C=O-、-C=S-、-(C=NR4)-、-P(=O)(R4)-、-C(=O)O-、-C(=O)NR4-、-HC=CH-、-R4C=CR4-もしくは-C≡C-で置き代えられてよく、また、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
R4は、出現毎に、同一であるか異なり、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または1以上の非芳香族R4基で置換されてよい4〜14個の炭素原子を有するアリールもしくはヘテロアリール基であり;
ただし、残基R1およびR2の少なくとも一つは、非芳香族環を含む。 - R1および/またはR2に含まれる非芳香族環は、環式炭化水素残基もしくはハロゲン化環式炭化水素残基、好ましくは、飽和環式炭化水素残基であることを特徴とする、請求項1記載の調合物。
- 残基R1およびR2は、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成しないことを特徴とする、請求項1または2記載の調合物。
- R1および/またはR2に含まれる非芳香族環は、モノ環式であることを特徴とする、請求項1〜3何れか1項記載の調合物。
- 残基R1および/またはR2は、置換基R3および/またはR4の炭素原子を含め、4、5、6、7、8、9、10、11、12、13、14もしくは15個の炭素原子を含むことを特徴とする、請求項1〜4何れか1項記載の調合物。
- 両残基R1およびR2は、非芳香族環を含むことを特徴とする、請求項1〜5何れか1項記載の調合物。
- 残基R1およびR2の一つは、直鎖もしくは分岐炭化水素残基またはハロゲン化直鎖もしくは分岐炭化水素残基、好ましくは、飽和直鎖炭化水素残基であることを特徴とする、請求項1〜6何れか1項記載の調合物。
- 残基R1および/またはR2は、2個以下の、好ましくは、1個以下の、より好ましくは、0個の置換基R4を含むことを特徴とする、請求項1〜7何れか1項記載の調合物。
- 式(I)で言及された置換基R3は、直鎖もしくは分岐炭化水素残基またはハロゲン化直鎖もしくは分岐炭化水素残基、好ましくは、飽和直鎖炭化水素残基であることを特徴とする、請求項1〜7何れか1項記載の調合物。
- 式(I)によるケトンは、100〜400℃の範囲、好ましくは、150〜350℃の沸点を有することを特徴とする、請求項1〜9何れか1項記載の調合物。
- 式(I)によるケトンは、25℃以下、より好ましくは、10℃以下の融点を有することを特徴とする、請求項1〜10何れか1項記載の調合物。
- ケトン溶媒は、第二の溶媒を含む混合物であり、第二の溶媒は、請求項1記載の一般式(I)のケトンとは異なることを特徴とする、請求項1〜11何れか1項記載の調合物。
- 第二の溶媒は、アルコール、アルデヒド、ケトン、エーテル、エステル、ジ-C1−2-アルキルホルムアミド等のアミド、硫黄化合物、ニトロ化合物、炭化水素、ハロゲン化炭化水素(たとえば、塩素化炭化水素)、芳香族もしくは複素環式芳香族炭化水素、ハロゲン化芳香族もしくは複素環式芳香族炭化水素および/または(環式)シロキサンより成る群から選ばれることを特徴とする、請求項12記載の調合物。
- 少なくとも一つの有機機能性材料が、有機伝導体、有機半導体、有機蛍光化合物、有機燐光化合物、有機光吸収化合物、有機光感応性化合物、有機光増感剤および遷移金属、希土類、ランタニドおよびアクチニドの有機金属錯体等の他の有機光活性化合物より成る群から選ばれることを特徴とする、請求項1〜13何れか1項記載の調合物。
- 少なくとも一つの有機機能性材料が、蛍光エミッター、燐光エミッター、ホスト材料、マトリックス材料、励起子ブロック材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、n−ドーパント、p−ドーパント、ワイドバンドギャップ材料、電子ブロック材料および正孔ブロック材料より成る群から選ばれることを特徴とする、請求項14記載の調合物。
- 電子素子の機能層の製造のために用いることができる、ケトン溶媒、随意のさらなる溶媒と有機機能性材料とが混合される、請求項1〜15何れか1項記載の調合物の製造方法。
- エレクトロルミッセンス素子の少なくとも一つの層は、請求項1〜15何れか1項記載の調合物が、基板上に適用され、好ましくは、印刷され、引き続き乾燥されることで調製される、エレクトロルミッセンス素子の製造方法。
- 請求項17記載の方法により得ることができる少なくとも一つの層を含むことを特徴とする電子素子。
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JP2008156636A (ja) * | 1999-04-06 | 2008-07-10 | Cambridge Display Technol Ltd | ポリマーのドーピング方法 |
JP2007106990A (ja) * | 2005-09-14 | 2007-04-26 | Sumitomo Chemical Co Ltd | 高分子化合物、発光材料及び発光素子 |
JP2009135053A (ja) * | 2007-11-30 | 2009-06-18 | Sumitomo Chemical Co Ltd | 電子デバイス、表示装置および電子デバイスの製造方法 |
JP2013534865A (ja) * | 2010-07-01 | 2013-09-09 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 色及び/又は効果を付与する複層塗装系の製造方法、その際に色を形成する被覆組成物がピンホール数を低下させるためにケトンを含有する |
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CN108368361A (zh) | 2018-08-03 |
WO2017097391A8 (en) | 2017-09-08 |
KR20180090362A (ko) | 2018-08-10 |
TW201736531A (zh) | 2017-10-16 |
WO2017097391A1 (en) | 2017-06-15 |
EP3387077A1 (en) | 2018-10-17 |
TWI787160B (zh) | 2022-12-21 |
US11005042B2 (en) | 2021-05-11 |
JP7106451B2 (ja) | 2022-07-26 |
EP3387077B1 (en) | 2023-10-18 |
JP2022037020A (ja) | 2022-03-08 |
US20200266349A1 (en) | 2020-08-20 |
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