JP6980682B2 - 少なくとも1種の有機半導体を含む配合物を含む容器 - Google Patents
少なくとも1種の有機半導体を含む配合物を含む容器 Download PDFInfo
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- JP6980682B2 JP6980682B2 JP2018548763A JP2018548763A JP6980682B2 JP 6980682 B2 JP6980682 B2 JP 6980682B2 JP 2018548763 A JP2018548763 A JP 2018548763A JP 2018548763 A JP2018548763 A JP 2018548763A JP 6980682 B2 JP6980682 B2 JP 6980682B2
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
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- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
- B41J2/17503—Ink cartridges
- B41J2/17513—Inner structure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/478—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a layer of composite material comprising interpenetrating or embedded materials, e.g. TiO2 particles in a polymer matrix
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Description
HOMO(eV)=((HEh*27.212)−0.9899)/1.1206
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
本願の文脈において、これらの値を、材料のHOMOおよびLUMOエネルギー準位とみなすべきである。
の化合物から選択される。
グループ1:正孔注入および/または正孔輸送特性を生み出すことができる構造要素;
グループ2:電子注入および/または電子輸送特性を生み出すことができる構造要素;
グループ3:グループ1および2に関して詳述する特性を組み合わせた構造要素;
グループ4:発光特性、とりわけ、リン光基を有する構造要素;
グループ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;
グループ6:結果として得られるポリマーの形態または発光色に影響する構造要素;
グループ7:典型的には骨格として使用される構造要素
ここで、構造要素は、異なる機能を更に有してもよく、そのため、明確な割り当ては、適切ではない可能性がある。例えば、グループ1の構造要素が同様に骨格として機能してもよい。
Ar1は、異なる反復単位に対して場合毎に同一であるか異なっており、単結合、または任意に置換されていてもよい単環式もしくは多環式アリール基であり;
Ar2は、異なる反復単位に対して場合毎に同一であるか異なっており、任意に置換されていてもよい単環式または多環式アリール基であり;
Ar3は、異なる反復単位に対して場合毎に同一であるか異なっており、任意に置換されていてもよい単環式または多環式アリール基であり;
mは、1、2または3である)
の反復単位の少なくとも1つを含む、正孔輸送または正孔注入特性を有するポリマーがとりわけ好ましい。
Raは、それぞれの事例において同一であるか異なっており、H、置換もしくは無置換芳香族もしくはヘテロ芳香族基、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、またはヒドロキシル基であり;
rは、0、1、2、3または4であり、
sは、0、1、2、3、4または5である)
の単位からなる群から選択される式HTP−1の反復単位が特に好ましい。
T1およびT2は、チオフェン、セレノフェン、チエノ[2,3b]チオフェン、チエノ[3,2b]チオフェン、ジチエノチオフェン、ピロール、アニリンから独立して選択され、ここで、これらの基は、1つ以上のRbラジカルによって置換されていてもよく;
Rbは、それぞれの事例において同一であるか異なっており、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、−SF5、任意に置換されていてもよくかつ任意に1つ以上のヘテロ原子を含んでもよい、1〜40個の炭素原子を有する任意に置換されていてもよいシリル、カルビルまたはヒドロカルビル基から選択され;
R0およびR00は、それぞれ独立して、H、または任意に置換されていてもよくかつ任意に1つ以上のヘテロ原子を含んでもよい、1〜40個の炭素原子を有する任意に置換されていてもよい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、独立して、任意に置換されていてもよくかつ任意に隣接するチオフェンまたはセレノフェン基の一方または両方の2,3位に結合していてもよい、単環式または多環式アリールまたはヘテロアリール基であり;
cおよびeは、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、独立して0、1、2、3または4である)
の反復単位の少なくとも1つを含む、正孔輸送または正孔注入特性を有するポリマーがとりわけ好ましい。
A、B、およびB’はそれぞれ、異なる反復単位に対して同一であるか異なっており、好ましくは、−CRcRd−、−NRc−、−PRc−、−O−、−S−、−SO−、−SO2−、−CO−、−CS−、−CSe−、−P(=O)Rc−、−P(=S)Rc−および−SiRcRd−から選択される二価基であり;
RcおよびRdは、それぞれの事例において同一であるか異なっており、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、−SF5、任意に置換されていてもよくかつ任意に1つ以上のヘテロ原子を含む、1〜40個の炭素原子を有する任意に置換されていてもよいシリル、カルビルまたはヒドロカルビル基から選択され、ここで、RcおよびRd基は、それらが結合しているフルオレンラジカルと共にスピロ基を任意に形成することができ;
Xは、ハロゲンであり;
R0およびR00は、それぞれ独立に、H、または任意に置換されていてもよくかつ任意に1つ以上のヘテロ原子を含む、1〜40個の炭素原子を有する任意に置換されていてもよいカルビルもしくはヒドロカルビル基であり;
gは、いずれの場合も独立して0または1であり、hは、いずれの場合も独立して0または1であり、ここで、いずれのサブユニット内の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、独立して、任意に置換されていてもよくかつ任意にインデノフルオレン基の7,8位または8,9位に結合していてもよい単環式または多環式アリールまたはヘテロアリール基であり;
aおよびbは、独立して0または1である)
により例示される。
の単位からなる群から選択される式PB−1の反復単位が特に好ましい。
Lは、H、ハロゲン、または1〜12個の炭素原子を有する任意にフッ素化されていてもよい、直鎖状もしくは分枝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;
L’は、1〜12個の炭素原子を有する任意にフッ素化されていてもよい、直鎖状または分枝アルキルまた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)
の単位からなる群から選択される式PB−1の反復単位が特に好ましい。
1.本発明の容器を用いて得ることができる電子デバイスは、従来の印刷カートリッジを用いて得られる電子デバイスと比較して、非常に高い安定性と、非常に長い寿命と、優れた品質とを呈し、その特性は、長期間の容器の保存または輸送後であっても達成することができる。
2.本発明の容器は、従来のプリンタに適用し、従来のプリンタで処理することができ、こうしたことでもコスト的な利点を実現することができる。
3.本発明の容器は、非常に微細に構造化された電子デバイスの製造にも使用できる配合物の、安全で信頼性の高い輸送を可能にする。
4.本発明の容器は、公知の機械で安価に製造することができ、改造が必要だとしても、わずかな改造しか必要としない。
OLED材料の印刷用に改変したプリンタカートリッジ:
OLEDコンポーネントの印刷のため、インクジェット法を使用する。所望のコンポーネントの個々の層の印刷のため、Dimatixが市販する工業用インクジェットプリンタを使用する。インクは、業界標準プリンタカートリッジを使用して供給する。使用するカートリッジは、プリンタインクを含有する多層フィルムパウチが中に埋め込まれた外側プラスチック容器からなる。多層フィルムパウチは、15マイクロメートルの薄アルミニウム層が施された厚さが100マイクロメートルの内側ポリエチレンフィルム、層厚が40マイクロメートルの外側PETフィルム、およびフィルムを結合するための中間層からなる。フィルムパウチ内のバルブを使用してインクを導入し、プリンタの操作のために抜き出すことができる。業界標準として利用可能なプリンタカートリッジは、水系印刷用インクの利用のために最適化されており、したがって、OLEDコンポーネント製造用の有機溶媒に溶解させた高感度材料の品質を保証するには不適切である。
有機電子機器および有機ソーラーセルにおけるインク用に改変された貯留容器:
有機電子機器またはソーラーセルのコンポーネントの製造においては、Nowpakブランド(Entegris)の容器が定着している。容器は、PTFE製のインライナフィルムパウチを備えた金属フラスコである。こうしたフラスコを本発明に従い、吸収材が金属フラスコの内側壁とPTFEフィルムパウチの間の内部空間に導入されるように改変する。吸収材の量は、容器の内容物の約1重量%とすべきである。吸収材は、グローブボックス内の乾燥雰囲気中、市販の乾燥シリカゲルとカルシウム粉末を10:1の比で激しく混合することにより製造する。製造直後、こうして製造された吸収材を乾燥雰囲気下で改変すべきフラスコの金属壁とインライナパウチの間の内部空間に導入する。本例において、容量が1000mlのフラスコ(Entegrisが販売するNowpakブランドのフラスコ)を使用した。
有機機能性インクおよびOLEDインクの印刷用供給容器
大型製造プラントで使用するため、インク供給用として、容器容積が1〜200リットル、更にはそれより大きいステンレス鋼容器が使用された。一例として、30リットルステンレス鋼容器を使用した。容器は、容器にネジ式に取り付けるシール付きの蓋を有する。本例では、この蓋は、安全弁および任意に測定装置だけでなく、ステンレス鋼パイプが装着された、それぞれ直径が10mmの2つのパイプリードスルーを備えている。一方のパイプは容器の底面のすぐ上まで到達しており、容器から液体を抜き出すのに役立つ。第2のパイプは、蓋のすぐ下で途切れており、容器の充填を可能とする。この2本のパイプはそれぞれ、蓋の上側でバルブでシールされており、標準的な充填または抜取装置に取り付けることができる接続器を備えている。本発明によれば、吸収材は、この供給容器に導入される。例3a)において、吸収材は、多孔質PTFEパウチ内に導入される。パウチに使用されるPTFEの最大細孔サイズは、100nmとすべきである。パウチは乾燥雰囲気中において吸収材で充填され、シールされ、供給容器の洗浄および乾燥後、乾燥状態の容器に挿入され、その後、充填および抜取パイプと共に容器の蓋がマウントされる。その後、インクが導入され、そのため吸収材を含むパウチと直接接触し、吸収材の多孔性のために吸収材に浸透することもできる。したがって、吸収材は、導入される印刷用インクと直接接触することになる。
Claims (19)
- 少なくとも1種の有機半導体を含む印刷用インクを含むインク貯留容器であって、前記印刷用インクが少なくとも1種の吸収材に接触していることを特徴とする、インク貯留容器。
- 前記吸収材が、酸素、水、二酸化炭素および/または水酸化物イオンと結合することができる、またはこれらの物質と反応することができることを特徴とする、請求項1に記載のインク貯留容器。
- 前記吸収材が、アルカリ金属もしくはアルカリ土類金属、またはそれらの酸化物;酸化アルミニウム、酸化チタンもしくは酸化ジルコニウム、酸化ケイ素、ゼオライト、シリカゲル、またはアルミノシリケート;遷移金属、またはそれらの酸化物、ならびにそれらの材料の組合せ、混合物または合金から選択されることを特徴とする、請求項1または2に記載のインク貯留容器。
- 前記吸収材が、フィルム、粉末、粒子径が1μm〜5mmの範囲の粒状材料、および/または成形体の形態を取ることを特徴とする、請求項1〜3何れか一項に記載のインク貯留容器。
- 前記吸収材が多孔質または微粒子であることを特徴とする、請求項1〜4何れか一項に記載のインク貯留容器。
- 前記吸収材が、前記印刷用インクと直接接触していることを特徴とする、請求項1〜5何れか一項に記載のインク貯留容器。
- 前記吸収材が、ポリマーフィルムに埋め込まれていることを特徴とする、請求項1〜5何れかに記載のインク貯留容器。
- 前記吸収材が中に存在するパウチ、容器、またはシェルを前記ポリマーフィルムを形成するように、前記ポリマーフィルムが前記吸収材を取り囲んでいることを特徴とする、請求項7に記載のインク貯留容器。
- 前記ポリマーフィルムが、ポリマー材料と吸収材が混合物の状態で存在しかつ前記吸収材が前記ポリマーフィルムに均一に分散するように、前記吸収材を含有することを特徴とする、請求項7に記載のインク貯留容器。
- 前記ポリマーフィルムが、拡散測定により計測した、酸素、水、二酸化炭素および/または水酸化物イオンに対する透過性が少なくとも0.001g/(m2d)(グラム毎平方メートル・日)であることを特徴とする、請求項7〜9何れか一項に記載のインク貯留容器。
- 吸収材対ポリマーフィルムの重量比が、500:1〜1:500の範囲であることを特徴とする、請求項7〜10何れか一項に記載のインク貯留容器。
- 前記インク貯留容器がプリンタカートリッジであることを特徴とする、請求項1〜10何れか一項に記載のインク貯留容器。
- 前記プリンタカートリッジが、前記少なくとも1種の有機半導体を含む印刷用インクが中に存在するインナーパウチが中に導入されているハウジングを有することを特徴とする、請求項12に記載のインク貯留容器。
- 前記インナーパウチが、酸素、水、二酸化炭素および/または水酸化物イオンが不透過の多層フィルムから形成されていることを特徴とする、請求項13に記載のインク貯留容器。
- 吸収材を含む層が前記インナーパウチの内表面の一部に少なくとも施されている、および/または前記吸収材が前記インナーパウチの内層に導入されていることを特徴とする、請求項12〜14何れか一項に記載のインク貯留容器。
- 前記プリンタカートリッジがバルブを有し、前記吸収材が前記バルブの近くに固定され、前記バルブに接着したポリマーフィルム、パウチ、容器またはシェルに導入されていることを特徴とする、請求項12〜15何れか一項に記載のインク貯留容器。
- 前記有機半導体が、ホスト材料、マトリクス材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、電子ブロック材料、および正孔ブロック材料から選択されることを特徴とする、請求項1〜16何れか一項に記載のインク貯留容器。
- 請求項1〜17何れか一項に記載のインク貯留容器の製造方法であって、少なくとも1種の有機半導体を含み、少なくとも1種の吸収材と接触させた印刷用インクをインク貯留容器に充填することを特徴とする、方法。
- 電子デバイスの製造のための請求項1〜17に記載のインク貯留容器の使用。
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Application Number | Priority Date | Filing Date | Title |
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DE102016003104.2A DE102016003104A1 (de) | 2016-03-15 | 2016-03-15 | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
DE102016003104.2 | 2016-03-15 | ||
PCT/EP2017/055641 WO2017157783A1 (de) | 2016-03-15 | 2017-03-10 | Behälter umfassend eine formulierung enthaltend mindestens einen organischen halbleiter |
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JP2019511426A JP2019511426A (ja) | 2019-04-25 |
JP6980682B2 true JP6980682B2 (ja) | 2021-12-15 |
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DE102016003104A1 (de) | 2017-09-21 |
CN108778756A (zh) | 2018-11-09 |
EP3429859B1 (de) | 2021-07-07 |
KR102380828B1 (ko) | 2022-03-30 |
JP2019511426A (ja) | 2019-04-25 |
TWI787176B (zh) | 2022-12-21 |
TW201801785A (zh) | 2018-01-16 |
US20190084309A1 (en) | 2019-03-21 |
CN108778756B (zh) | 2021-03-02 |
EP3429859A1 (de) | 2019-01-23 |
KR20180121988A (ko) | 2018-11-09 |
US10668733B2 (en) | 2020-06-02 |
WO2017157783A1 (de) | 2017-09-21 |
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