JP2022502829A - 粒状材料を製造するための方法 - Google Patents
粒状材料を製造するための方法 Download PDFInfo
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- JP2022502829A JP2022502829A JP2021540918A JP2021540918A JP2022502829A JP 2022502829 A JP2022502829 A JP 2022502829A JP 2021540918 A JP2021540918 A JP 2021540918A JP 2021540918 A JP2021540918 A JP 2021540918A JP 2022502829 A JP2022502829 A JP 2022502829A
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- 239000008187 granular material Substances 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 39
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 40
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- 238000002347 injection Methods 0.000 claims description 18
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- 230000004927 fusion Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ABCGFHPGHXSVKI-UHFFFAOYSA-O meso-tetrakis(n-methyl-4-pyridyl)porphine(4+) Chemical compound C1=C[N+](C)=CC=C1C(C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(=N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 ABCGFHPGHXSVKI-UHFFFAOYSA-O 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 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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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 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
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
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- 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
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
-
- 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
- B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
- B01J2/02—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by dividing the liquid material into drops, e.g. by spraying, and solidifying the drops
- B01J2/04—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by dividing the liquid material into drops, e.g. by spraying, and solidifying the drops in a gaseous medium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
Description
A)電子デバイスの機能層の製造に使用できる機能材料の溶融物を用意する工程;
B)A)において得られた溶融物を下降管に移送する工程;
C)工程B)において下降管に移送された溶融物を冷却して粒状材料を得る工程
を含む方法を提供する。
HOMO(eV)=((HEh*27.212)−0.9899)/1.1206LUMO(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こととする。
1.本発明の粒状材料は、高度に環境に優しく、特に労働安全性が高いという点で注目に値する。
適用容器(10)において、290℃および500mbarでM−1を溶融させた。溶融物はノズル(14)を介して下降管(16)に流入する。ノズル(14)は、0.3mmの直径を有する。長さ2.5mの下降管(16)は、335mbarの圧力のヘリウムで満たされている。下降管(16)は、1.0mの長さにわたり液体窒素で冷却される冷却ジャケットを備えている。粒状材料は、収集容器(19)に収集される。
Claims (15)
- 電子デバイスの機能層の製造に使用できる少なくとも1種の機能材料(FM)を含む粒状材料を製造するための方法であって、
A)電子デバイスの機能層の製造に使用できる機能材料の溶融物を、適用容器中に用意する工程;
B)A)において得られた前記溶融物を下降管に移送する工程;
C)工程B)において前記下降管に移送された前記溶融物を冷却して粒状材料を得る工程
を含む、方法。 - 電子デバイスの機能層の製造に使用できる前記機能材料(FM)が、蛍光発光体、リン光発光体、TADF(熱活性化型遅延蛍光)を呈する発光体、ホスト材料、電子輸送材料、励起子阻止材料、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、電子阻止材料、正孔阻止材料および/または液晶特性を有する材料からなる群から選択されることを特徴とする、請求項1に記載の方法。
- 電子デバイスの機能層の製造に使用できる前記機能材料(FM)が、50℃を超える温度で分解することなく溶融可能であることを特徴とする、請求項1または2に記載の方法。
- 電子デバイスの機能層の製造に使用できる前記機能材料(FM)が、処理温度で溶融状態で、10時間の保存期間にわたり0.1重量%以下の分解を呈することを特徴とする、請求項3に記載の方法。
- 前記工程B)において前記溶融物を下降管に移送する圧力が、前記下降管内の圧力よりも高く、前記適用容器内の圧力が少なくとも150mbar、好ましくは400〜700mbarの範囲であり、前記下降管内の圧力が少なくとも75mbar、好ましくは250〜500mbarであることを特徴とする、先行する請求項の何れか1項に記載の方法。
- 工程B)において前記下降管に移送された前記溶融物が、工程C)において不活性ガスで冷却されることを特徴とする、請求項1〜5の何れか1項に記載の方法。
- 前記不活性ガスが、0℃以下、好ましくは−200〜−70℃の範囲の温度を有することを特徴とする、請求項6に記載の方法。
- 工程B)において前記下降管に移送された前記溶融物が、工程C)において少なくとも50cmの下降高さにわたり、好ましくは100〜800cmの範囲の下降高さにわたり冷却されることを特徴とする、請求項1〜7の何れか1項に記載の方法。
- 前記下降管内に100〜750mbarの範囲、好ましくは250〜500mbarの範囲の絶対圧力が存在することを特徴とする、請求項1〜8の何れか1項に記載の方法。
- 工程B)において前記溶融物がノズルを通して前記下降管に移送されることを特徴とする、請求項1〜9の何れか1項に記載の方法。
- 前記ノズルが、0.7mm以下の直径、好ましくは0.1〜0.5mmの範囲の直径、より好ましくは0.2〜0.3mmの範囲の直径を有することを特徴とする、請求項10に記載の方法。
- 電子デバイスの機能層の製造に使用できる前記機能材料(FM)が、フェニル、フルオレン、インデノフルオレン、スピロビフルオレン、カルバゾール、インデノカルバゾール、インドロカルバゾール、スピロカルバゾール、ピリミジン、トリアジン、ラクタム、トリアリールアミン、ジベンゾフラン、ジベンゾチエン、イミダゾール、ベンゾイミダゾール、ベンゾオキサゾール、ベンゾチアゾール、5−アリールフェナントリジン−6−オン、9,10−デヒドロフェナントレン、フルオランテン、アントラセン、ベンゾアントラセン、フルオラデンからなる群から選択されることを特徴とする、請求項1〜11の何れか1項に記載の方法。
- 請求項1〜12の何れか1項に記載の方法により得ることができる粒状材料。
- 電子デバイスの製造のための請求項13に記載の粒状材料の使用。
- 前記粒状材料が蒸発デバイスに移送されることを特徴とする、請求項14に記載の使用。
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PCT/EP2019/075445 WO2020064582A1 (de) | 2018-09-24 | 2019-09-23 | Verfahren zur herstellung von granulat |
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Also Published As
Publication number | Publication date |
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EP3857621A1 (de) | 2021-08-04 |
CN112740432A (zh) | 2021-04-30 |
KR20210056432A (ko) | 2021-05-18 |
WO2020064582A1 (de) | 2020-04-02 |
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