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WO2003022857A1 - Complexe de terres rares, materiau photofonctionnel et dispositif electroluminescent employant chacun ce complexe - Google Patents

Complexe de terres rares, materiau photofonctionnel et dispositif electroluminescent employant chacun ce complexe Download PDF

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Publication number
WO2003022857A1
WO2003022857A1 PCT/JP2002/009073 JP0209073W WO03022857A1 WO 2003022857 A1 WO2003022857 A1 WO 2003022857A1 JP 0209073 W JP0209073 W JP 0209073W WO 03022857 A1 WO03022857 A1 WO 03022857A1
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WO
WIPO (PCT)
Prior art keywords
group
rare earth
complex
earth complex
same
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Application number
PCT/JP2002/009073
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English (en)
Japanese (ja)
Inventor
Yasuchika Hasegawa
Shozo Yanagida
Yuji Wada
Junichi Shimada
Yoichi Kawakami
Shigeo Fujita
Original Assignee
Kansai Technology Licensing Organization Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kansai Technology Licensing Organization Co., Ltd. filed Critical Kansai Technology Licensing Organization Co., Ltd.
Publication of WO2003022857A1 publication Critical patent/WO2003022857A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5345—Complexes or chelates of phosphine-oxides or thioxides with metallic compounds or metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium

Definitions

  • the present invention relates to a rare earth complex having useful optical properties, and an optical functional material and a light emitting device using the same.
  • neodymium-containing glass has been put into practical use as an electronic device for laser beams.
  • their production and processing are difficult and their production costs are high, so their applications are limited.
  • JP 64-26583 as a polymer composition having a luminescent, Chiofen and CF having 3 as a substituent / 3 - resin composition containing Anmoniumu salt of diketone ZEu complexes have been disclosed .
  • Japanese Patent Application No. 10-238973 discloses a resin composition containing a deuterated / 3-diketone ZEu complex or a sulfonate ZEu complex having CF 3 as a substituent as a luminescent polymer composition. ing.
  • composition having more excellent absorption / emission properties.Now, the composition itself and an optical functional material using the composition, It provides a light emitting device by combining it with an LED or a semiconductor laser. Disclosure of the invention
  • the composition according to the present invention is a rare earth complex represented by the general formula (II) in FIG.
  • Ln represents a rare earth atom
  • nl represents 2 or 3.
  • n2 represents 1 or 2.
  • n3 represents 1, 2, 3 or 4.
  • X is identical or different hydrogen atom, a deuterium atom, a halogen atom (F, C l. Br, I), Ci ⁇ C 2.
  • Y represents the same or different C, to (; 2 ; a hydroxyl group, a nitro group, an amino group, a sulfonyl group, a cyano group, a silyl group, a phosphonic acid group, a diazo group, and a mercapto group; and Z represents a hydrogen atom or Indicates a deuterium atom.
  • Aromatic groups such as phenyl, naphthyl, biphenyl, etc., and perfluorophenyl, perfluoronaphthyl, perfluorobiphenyl, perchlorophenyl, perchloronaphthyl, perchlorobiphenyl Perhalogenated aromatic groups such as;
  • a heteroaromatic group such as a pyridyl group and a perhalogenated heteroaromatic group such as a perfluoropyridyl group;
  • Aralkyl groups such as benzyl group and phenethyl group and perhalogenated aralkyl groups such as perfluorobenzoyl group;
  • the groups represented by X and Y (, to (: 2.) include, if necessary, a deuterium atom, a halogen atom (F. Cl. Br, I), a hydroxyl group, a nitro group, an amino group, a sulfonyl group, a cyano group. group, a silyl group, a phosphonic acid group, Jiazo group, and may also be substituted with a substituent such as a mercapto group, ( ⁇ ⁇ (;. 2 between the C-C single bond at any position of the base
  • An ether, ester, or ketone structure may be formed by interposing one or more of -0-, -C00-, and -CO-.
  • the rare earth complex of the general formula (II) in which X and Y are alkenyl groups may be polymerized with an olefin such as ethylene or propylene and a halogenated olefin, if necessary, to obtain a polymer rare earth complex.
  • an olefin such as ethylene or propylene and a halogenated olefin, if necessary, to obtain a polymer rare earth complex.
  • the above-mentioned compounds can be used as Y.
  • An alkyl group having 1 to 4 carbon atoms, a perhalogenated alkyl group, an aromatic group, a perhalogenated aromatic group, a heteroaromatic group, and a perhalogenated heteroaromatic group are preferable, and among them, a perfluoroalkyl group is preferable.
  • Most preferred are an aromatic group and a heteroaromatic group.
  • rare earth element represented by Ln examples include lanthanum series elements such as La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and Lu. Nd, Eu, Tb and Yb are mentioned. nl is 2 or 3, preferably 3.
  • n2 is 1 or 2, preferably 2.
  • n3 is any of 1 to 4, preferably 3.
  • a complex of the general formula (I) according to claim 1 (where Z is a deuterium atom D) is obtained by subjecting the complex represented by the general formula (II) to a deuteration reaction with a deuterating agent.
  • a deuterating agent used is a protic compound containing deuterium, specifically, deuterated alcohols such as deuterated water, deuterated methanol and deuterated methanol, hydrogen deuterium chloride, deuterated alkali, etc. Is mentioned.
  • a base agent or an additive such as trimethylamine or triethylamine may be added to promote the reaction.
  • the deuterium substitution reaction is obtained by mixing the complex represented by the general formula (II) and a deuterating agent, but an aprotic solvent may be added during the reaction.
  • the aprotic solvent include ketone solvents such as acetone and methyl ethyl ketone, ether solvents such as getyl ether and tetrahydrofuran, halogen solvents such as chloroform and methylene chloride, DMS0 and DMF.
  • a solvent in which the general formula (11) is soluble is preferable.
  • the amount of the deuterating agent to be used is, for example, about 1 to 100 parts by weight, preferably 1 to 20 parts by weight, based on the total amount of the complex represented by the general formula (II) (1 part by weight). Parts.
  • the method of mixing is not particularly limited, and may be 0.1 to 100 hours, preferably 0.1 to 100 ° C., preferably at a temperature of 30 ° C. to 100 ° C., with stirring as necessary. Mix for 1-20 hours.
  • the deuterating agent and the solvent are distilled off to obtain the complex represented by the general formula (I). Further, if necessary, it can be further purified by a method such as recrystallization, column chromatography, or sublimation.
  • the rare earth complex represented by the general formula (I) and the general formula (II) can be prepared.
  • the rare earth complex having the above-mentioned useful light-absorbing and light-emitting properties in a transparent solid carrier, it can be used for various optical functional materials such as a light-emitting auxiliary and an optical lens.
  • the crystal of the rare earth complex itself is also used as an optical functional material. be able to.
  • a transparent solid support containing a crystal of the rare earth complex or a rare earth complex is combined with a light emitting diode or a semiconductor laser that emits excitation light corresponding to the ff transition of the central ion of the rare earth complex or the absorption of the ligand.
  • the light-emitting device can be used as a light-emitting device with high luminous efficiency.
  • a transparent solid carrier a transparent polymer matrix, transparent glass, or the like can be used.
  • Transparent polymer matrices include polymethyl methacrylate, fluorinated polymethacrylate, polyacrylate, fluorinated polyacrylate, polystyrene, polyolefin such as polyethylene, polypropylene, polybutene, fluorinated polyolefin, polyvinyl ether, fluorinated polyvinyl ether, and polyacetic acid.
  • Examples include vinyl, polyvinyl chloride, and their copolymers, cellulose, polyacetal, polyester, polycarbonate, epoxy resin, polyamide resin, polyimide resin, polyurethane, naphion, petroleum resin, rosin, and silicone resin.
  • a polar solvent can be included at the same time in order to enhance the transparency.
  • the polar solvent for example, DMS0-d 6 rare earth complex and a transparent solid support containing the same of the present invention which may be used (dimethyl sulfoxide) is high conversion efficiency of light, LED or new by a combination of a semiconductor laser It is useful as a light emitting device, and can be applied to general lighting devices, signal devices, display devices, and the like.
  • the rare-earth complex of the present invention can change the emission wavelength by changing the structure of the ligand and / or the kind of the rare-earth atom, and can obtain color development of an arbitrary wavelength.
  • FIG. 1 is a general formula of a rare earth complex according to the present invention.
  • FIG. 2 is a comparison table of the emission characteristics of the rare earth complex of the example of the present invention and the rare earth complex of the comparative compound.
  • FIG. 3 is a graph of a light emitting spectrum of a rare earth complex of a working example of the present invention and a rare earth complex of a comparative compound.
  • FIG. 4 is a graph of an excitation spectrum of a rare earth complex which is an example of the present invention.
  • Fig. 5 A graph showing the results of measuring the spectrum of transmitted light by placing sample A over an InGaN blue LED with a central emission wavelength of 465 nm.
  • Fig. 6 Graph showing the results of measuring the spectrum of transmitted light by placing sample A over an InGaN purple LED with a central emission wavelength of 405 nm.
  • Fig. 7 Graph showing the results of measuring the spectrum of transmitted light by placing sample A over a white LED with an InGaN blue LED covered with a YAG phosphor.
  • the target complex (Eu (hfa-H) 3 (TPPO) 2 ) was obtained by recrystallization with a mixed solvent of toluene and hexane.
  • the deuteration reaction of the complex obtained in Example 2 was performed according to a known literature (Hasegawa, Y .; Murakoshi, K .; Wada, Y .; Yanagida, S .; Kim, J .; Nakashima, N .; Yamanaka, TJ Phys. Chem. 1996, 100, 10201.).
  • the resulting powder was sufficiently dried to obtain the desired complex (Eu (hfa-D) 3 (TPP0) 2 ).
  • Polymers containing the complex obtained in Example 3 were obtained from publicly known literature (Hasegawa, Y .; Sogabe, K .; Wada, Y .; Kitamura, T .; Nakashima, N .; Yanagida, S. Chem. Lett. 1999, 35.).
  • Fig. 2 shows the emission characteristics of the 1 ⁇ polymer (B) containing
  • PMMA polymers containing rare earth complexes described in the literature Hasegawa, Y .; Sogabe, K .; Wada, Y .; Kitamura, T .; Nakashima, N .; Yanagida, S. Chem. Lett. 1999) , 35.
  • the emission characteristics of (C, D) are shown in the same graph. From FIG.
  • the transparent solid support ( ⁇ , ⁇ ) containing the complex of the present invention is the one described in the literature (relation A containing Eu (hfa-D) 3 (D 20 ) 2) (C, D It can be seen that the light emission quantum yield is dramatically improved compared to ().
  • FIG. 3 shows a graph of the emission spectrum of each sample.
  • the spectrum intensity on the vertical axis was normalized with the emission intensity at 590 nm as 1.
  • Excitation wavelength is the central ion of the complex It is 465 nm corresponding to the ff transition of Eu 3+ .
  • Sample A PMMA containing Eu (hfa-D) 3 (TPP0) 2
  • TPP0 TPP0
  • the peak intensity ratio of each sample is different. This shows that the color rendering of light emission can be adjusted within a certain range by appropriately designing the selection of ligands and the presence / absence (more or less) of additives.
  • FIG. 3 shows that the color rendering of light emission can be adjusted within a certain range by appropriately designing the selection of ligands and the presence / absence (more or less) of additives.
  • FIG. 3 shows an excitation spectrum of an example sample A (PMMA containing Eu (hfa-D) 3 (TPP0) 2).
  • sample A PMMA containing Eu (hfa-D) 3 (TPP0) 2.
  • TPP0 TPP0
  • 465 nm is due to the f-f transition of the central ion Eu 3+ as described above, and the broad absorption band from 370 to 450 nm is due to many overlapping f-f transitions or ligands. Seem.
  • Figure 5 shows a sample A (PMMA containing Eu (hfa-D) 3 (TPPO) 2 ) over an InGaN blue LED and the spectrum of the transmitted light measured.
  • InGaN-LED is obtained by adjusting the component variable X so that the center of the emission wavelength is 465 nm, and has an emission peak in the range of 450 to 500 nm, in which the rare-earth complex Eu (hfa -D) 3 (TPPO) 2 A sharp absorption peak occurs due to the ff transition of the central ion Eu.
  • a large emission peak appears at 615 nm, and small emission peaks appear near 591 nm and 700 nm. As shown in Fig. 2, these have high luminous efficiency of about 70%.
  • Figure 6 shows the emission wavelength of the sample A (PMA including Eu (hfa-D) 3 (TPP0) 2) adjusted by adjusting the component variable X of the InGaN-LED to fall within the broad excitation light range of 370 to 450 nm. Is the result of performing the same measurement with 405 nm. In this case as well, a large peak appears around 615 nm, and small peaks appear around 591 nm and 700 nm.
  • Figure 7 shows a similar measurement with a sample A (PMMA containing Eu (hfa-D) 3 (TPP0) 2) over a conventional white LED (InGaN blue LED covered with YAG phosphor). This is the result of performing. An absorption peak due to the ff transition of Eu "is clearly observed at 465 nm. As a result, a large emission peak appears around 615 nm. As is clear from this figure, the light emitting device manufactured in this manner. Is close to the ideal white color, supplementing the red component lacking in conventional white LEDs. A white light source having high color rendering properties is obtained. This can be used as a useful light source in fields where color discrimination or color rendering is particularly required, such as surgery and product displays.
  • the rare earth complex according to the present invention has such light absorption characteristics, it can be usefully used as a highly efficient wavelength conversion optical functional material by combining an LED or a semiconductor laser as its excitation light source.
  • a broad absorption band of 370 to 450 nm as shown in FIG. 4 is considered to have a great effect when combined with a broadband light emitter such as EL.
  • the usefulness of such a wavelength-converting optical functional material and a light-emitting device obtained by combining it with an LED or a semiconductor laser is discussed in detail in the above-mentioned earlier application (Japanese Patent Application No. 2001-135116).
  • the rare earth complex according to the present invention and the optical functional material that is a transparent solid carrier containing the same, and furthermore, the light emitting device obtained by combining it with an LED, a semiconductor laser, and other light emitters have the same industrial utility to society. To provide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
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Abstract

La présente invention concerne un complexe de terres rares destiné à des matériaux photofonctionnels, représenté par la formule générale de la figure (I). Dans cette formule, Ln est un atome de terre rare, n1 vaut 2 ou 3, n2 vaut 1 ou 2, et n3 vaut 1, 2, 3, ou 4. Les X, qui sont identiques ou différents, sont chacun hydrogène, deutérium, halogéno, groupe en C1-C20, hydroxy, nitro, amino, sulfonyle, cyano, silyle, phosphono, diazo, ou mercapto. Les Y, qui sont identiques ou différents, sont chacun groupe en C1-C20, hydroxy, nitro, amino, sulfonyle, cyano, silyle, phosphono, diazo, ou mercapto. Enfin, Z est hydrogène ou deutérium. L'invention concerne également un matériau photofonctionnel comprenant un support solide transparent renfermant un complexe de terres rares. L'invention concerne enfin un dispositif électroluminescent comprenant une combinaison réunissant le matériau photofonctionnel et une diode électroluminescente ou un laser semi-conducteur.
PCT/JP2002/009073 2001-09-07 2002-09-05 Complexe de terres rares, materiau photofonctionnel et dispositif electroluminescent employant chacun ce complexe WO2003022857A1 (fr)

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JP2001272547A JP3668966B2 (ja) 2001-09-07 2001-09-07 希土類錯体並びにそれを用いた光機能材料及び発光装置
JP2001-272547 2001-09-07

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Cited By (2)

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EP1659128A1 (fr) * 2003-08-26 2006-05-24 Dainippon Ink And Chemicals, Inc. Complexe des terres rares optiquement actif a emission de lumiere polarisee circulaire
CN105061481A (zh) * 2015-08-26 2015-11-18 重庆理工大学 三元铽配合物单体和其与三元铽配合物单体-mma共聚物发光材料的制备方法

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JP3811142B2 (ja) 2003-06-24 2006-08-16 株式会社東芝 希土類錯体を用いたｌｅｄ素子及び発光媒体
EP1717290A1 (fr) * 2004-02-06 2006-11-02 Mitsubishi Chemical Corporation Dispositif luminescent et dispositif d'eclairage l'utilisant, unite d'affichage d'images
JP5010915B2 (ja) * 2004-04-20 2012-08-29 九州電力株式会社 有機電界発光素子およびその製造方法
JP4731485B2 (ja) 2004-07-05 2011-07-27 株式会社Ｋｒｉ 有機無機複合体
WO2006046607A1 (fr) * 2004-10-29 2006-05-04 Fujifilm Corporation Élément électroluminescent de type à dispersion
US7350933B2 (en) * 2005-05-23 2008-04-01 Avago Technologies Ecbu Ip Pte Ltd Phosphor converted light source
US7839072B2 (en) 2006-05-24 2010-11-23 Citizen Electronics Co., Ltd. Translucent laminate sheet and light-emitting device using the translucent laminate sheet
WO2008111293A1 (fr) * 2007-03-09 2008-09-18 National University Corporation NARA Institute of Science and Technology Complexe des terres rares et son utilisation
JP4992021B2 (ja) * 2007-04-04 2012-08-08 国立大学法人大阪大学 強発光性希土類錯体
JP2008297250A (ja) 2007-05-31 2008-12-11 Toshiba Corp 蛍光性希土類錯体、ならびにそれを用いた発光素子、セキュリティー媒体、および照明装置
WO2010032395A1 (fr) * 2008-09-19 2010-03-25 国立大学法人奈良先端科学技術大学院大学 Nanocristaux de complexe de terre rare et leurs applications
JP2012082135A (ja) * 2009-01-30 2012-04-26 Central Techno Corp 発光マニキュア
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JP5737719B2 (ja) 2009-07-29 2015-06-17 国立大学法人 奈良先端科学技術大学院大学 希土類錯体及びその利用
TWI453161B (zh) * 2009-11-11 2014-09-21 Univ Nat Chunghsing 具親水性之經修飾ii-vi族量子點及其製法
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JP6378010B2 (ja) * 2013-09-04 2018-08-22 国立大学法人北海道大学 希土類錯体ポリマーとその製造方法、及びプラスチック成形体
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US10399999B2 (en) 2015-03-09 2019-09-03 National University Corporation Hokkaido University Polymer complex and production process therefor
JP6513605B2 (ja) * 2016-06-21 2019-05-15 セントラルテクノ株式会社 三次元印刷のためのフィラメント
JP7217621B2 (ja) * 2017-11-27 2023-02-03 東ソー株式会社 ユウロピウム錯体及びその用途
WO2019103155A1 (fr) 2017-11-27 2019-05-31 東ソー株式会社 Complexe d'europium
JP2023123882A (ja) * 2020-07-10 2023-09-06 国立大学法人北海道大学 発光材料、発光インク、発光体及び発光デバイス
KR20240029044A (ko) 2021-07-05 2024-03-05 도소 가부시키가이샤 희토류 착체
KR102705443B1 (ko) * 2023-09-25 2024-09-11 주식회사 에스켐 신규한 중수소화 테트라-치환된 다이포스페이트-삼불화붕소계 화합물 및 이의 제조방법

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EP1659128A1 (fr) * 2003-08-26 2006-05-24 Dainippon Ink And Chemicals, Inc. Complexe des terres rares optiquement actif a emission de lumiere polarisee circulaire
EP1659128A4 (fr) * 2003-08-26 2006-11-15 Dainippon Ink & Chemicals Complexe des terres rares optiquement actif a emission de lumiere polarisee circulaire
CN105061481A (zh) * 2015-08-26 2015-11-18 重庆理工大学 三元铽配合物单体和其与三元铽配合物单体-mma共聚物发光材料的制备方法

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