JP7359151B2 - ピロメテンホウ素錯体、色変換組成物、色変換フィルム、光源ユニット、ディスプレイおよび照明装置 - Google Patents
ピロメテンホウ素錯体、色変換組成物、色変換フィルム、光源ユニット、ディスプレイおよび照明装置 Download PDFInfo
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Images
Classifications
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V9/00—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters
- F21V9/40—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters with provision for controlling spectral properties, e.g. colour, or intensity
- F21V9/45—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters with provision for controlling spectral properties, e.g. colour, or intensity by adjustment of photoluminescent elements
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
- H01L33/502—Wavelength conversion materials
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Description
本発明の実施形態に係るピロメテンホウ素錯体について詳細に説明する。本発明の実施形態に係るピロメテンホウ素錯体は、色変換組成物や色変換フィルムなどを構成する色変換材料である。詳細には、このピロメテンホウ素錯体は、下記の一般式(1)で表される、分子量が1000以上の化合物である。かつ、このピロメテンホウ素錯体において、一般式(1)におけるR1~R6のうち少なくとも2つは、後述する一般式(2)で表される基である。以下、本実施形態に係るピロメテンホウ素錯体としての「一般式(1)で表される、分子量が1000以上の化合物」は、「一般式(1)で表される化合物」と略記する場合がある。まず、一般式(1)で表される化合物に着目して、本実施形態に係るピロメテンホウ素錯体を詳細に説明する。
本発明の実施形態に係る色変換組成物について詳細に説明する。本発明の実施形態に係る色変換組成物は、光源等の発光体からの入射光を、その入射光よりも長波長の光に変換するものであって、上述した一般式(1)で表される化合物(ピロメテンホウ素錯体)およびバインダー樹脂を含むことが好ましい。
バインダー樹脂は、連続相を形成するものであり、成型加工性、透明性、耐熱性等に優れる材料であればよい。バインダー樹脂の例としては、例えば、アクリル酸系、メタクリル酸系、ポリケイ皮酸ビニル系、環ゴム系等の反応性ビニル基を有する光硬化型レジスト材料、エポキシ樹脂、シリコーン樹脂(シリコーンゴム、シリコーンゲル等のオルガノポリシロキサン硬化物(架橋物)を含む)、ウレア樹脂、フッ素樹脂、ポリカーボネート樹脂、アクリル樹脂、ウレタン樹脂、メラミン樹脂、ポリビニル樹脂、ポリアミド樹脂、フェノール樹脂、ポリビニルアルコール樹脂、セルロース樹脂、脂肪族エステル樹脂、芳香族エステル樹脂、脂肪族ポリオレフィン樹脂、芳香族ポリオレフィン樹脂等の公知のものが挙げられる。また、バインダー樹脂としては、これらの共重合樹脂を用いても構わない。これらの樹脂を適宜設計することで、本発明の実施形態に係る色変換組成物および色変換フィルムに有用なバインダー樹脂が得られる。これらの樹脂の中でも、フィルム化のプロセスが容易であることから、熱可塑性樹脂がさらに好ましい。熱硬化性樹脂の中でも、透明性、耐熱性等の観点から、エポキシ樹脂、シリコーン樹脂、アクリル樹脂、エステル樹脂、オレフィン樹脂またはこれらの混合物を好適に用いることができる。また、耐久性の観点から特に好ましい熱可塑性樹脂は、アクリル樹脂、エステル樹脂、シクロオレフィン樹脂である。
本発明の実施形態に係る色変換組成物は、上述した一般式(1)で表される化合物およびバインダー樹脂以外に、光安定化剤、酸化防止剤、加工および熱安定化剤、紫外線吸収剤等の耐光性安定化剤、シリコーン微粒子およびシランカップリング剤等、その他の成分(添加剤)を含有してもよい。
本発明の実施形態に係る色変換組成物は、溶剤を含んでいてもよい。溶剤は、流動状態の樹脂の粘度を調整でき、発光物質の発光および耐久性に過度な影響を与えないものであれば、特に限定されない。このような溶媒として、例えば、トルエン、メチルエチルケトン、メチルイソブチルケトン、ヘキサン、アセトン、テルピネオール、テキサノール、メチルセルソルブ、ブチルカルビトール、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテルアセテート等が挙げられる。これらの溶剤を2種類以上混合して使用することも可能である。これらの溶剤の中で特にトルエンは、一般式(1)で表される化合物の劣化に影響を与えず、乾燥後の残存溶媒が少ない点で好適に用いられる。
以下に、本発明の実施形態に係る色変換組成物の製造方法の一例を説明する。この製造方法では、前述した一般式(1)で表される化合物、バインダー樹脂、溶剤等を所定量混合する。上記の成分を所定の組成になるよう混合した後、ホモジナイザー、自公転型攪拌機、3本ローラー、ボールミル、遊星式ボールミル、ビーズミル等の撹拌・混練機で均質に混合分散することで、色変換組成物が得られる。混合分散後、もしくは混合分散の過程で、真空もしくは減圧条件下で脱泡することも好ましく行われる。また、ある特定の成分を事前に混合することや、エージング等の処理をしても構わない。エバポレーターによって溶剤を除去して所望の固形分濃度にすることも可能である。
本発明において、色変換フィルムは、上述した色変換組成物、またはそれを硬化した硬化物からなる層を含んでいれば、その構成に限定はない。色変換組成物の硬化物は、色変換組成物を硬化することによって得られる層(色変換組成物の硬化物からなる層)として色変換フィルムに含まれることが好ましい。色変換フィルムの代表的な構造例として、例えば、以下の四つが挙げられる。
基材層(例えば図2~4に示す基材層10)としては、特に制限無く公知の金属、フィルム、ガラス、セラミック、紙等を使用することができる。具体的には、基材層として、アルミニウム(アルミニウム合金も含む)、亜鉛、銅、鉄等の金属板や箔、セルロースアセテート、ポリエチレンテレフタレート(PET)、ポリエチレン、ポリエステル、ポリアミド、ポリイミド、ポリフェニレンサルファイド、ポリスチレン、ポリプロピレン、ポリカーボネート、ポリビニルアセタール、アラミド、シリコーン、ポリオレフィン、熱可塑性フッ素樹脂、テトラフルオロエチレンとエチレンとの共重合体(ETFE)等のプラスチックのフィルム、α-ポリオレフィン樹脂、ポリカプロラクトン樹脂、アクリル樹脂、シリコーン樹脂およびこれらとエチレンとの共重合樹脂からなるプラスチックのフィルム、前記プラスチックがラミネートされた紙、または前記プラスチックによりコーティングされた紙、前記金属がラミネートまたは蒸着された紙、前記金属がラミネートまたは蒸着されたプラスチックフィルム等が挙げられる。また、基材層が金属板である場合、その表面にクロム系やニッケル系等のメッキ処理やセラミック処理が施されていてもよい。
つぎに、本発明の実施形態に係る色変換フィルムの色変換層の製造方法の一例を説明する。この色変換層の製造方法では、上述した方法で作製した色変換組成物を、基材層やバリアフィルム等の下地上に塗布し、乾燥させる。このようにして、色変換層(例えば図1~4に示す色変換層11)が形成される。塗布は、リバースロールコーター、ブレードコーター、スリットダイコーター、ダイレクトグラビアコーター、オフセットグラビアコーター、キスコーター、ナチュラルロールコーター、エアーナイフコーター、ロールブレードコーター、リバースロールブレードコーター、トゥーストリームコーター、ロッドコーター、ワイヤーバーコーター、アプリケーター、ディップコーター、カーテンコーター、スピンコーター、ナイフコーター等により、行うことができる。色変換層の膜厚均一性を得るためには、スリットダイコーターで塗布することが好ましい。
バリアフィルム(例えば図4に示すバリアフィルム12)は、色変換層に対してガスバリア性を向上する場合等において適宜用いられる。このバリアフィルムとしては、例えば、酸化ケイ素、酸化アルミニウム、酸化チタン、酸化タンタル、酸化亜鉛、酸化スズ、酸化インジウム、酸化イットリウム、酸化マグネシウム等の無機酸化物や、窒化ケイ素、窒化アルミニウム、窒化チタン、炭化窒化ケイ素等の無機窒化物、またはこれらの混合物、またはこれらに他の元素を添加した金属酸化物薄膜や金属窒化物薄膜、あるいはポリ塩化ビニリデン、アクリル系樹脂、シリコン系樹脂、メラミン系樹脂、ウレタン系樹脂、フッ素系樹脂、酢酸ビニルのケン化物等のポリビニルアルコール系樹脂等の各種樹脂から成る膜を挙げることができる。また、水分に対してバリア機能を有するバリアフィルムとしては、例えば、ポリエチレン、ポリプロピレン、ナイロン、ポリ塩化ビニリデン、塩化ビニリデンと塩化ビニルとの共重合物、塩化ビニリデンとアクリロニトリルとの共重合物、フッ素系樹脂、酢酸ビニルのケン化物等のポリビニルアルコール系樹脂等の各種樹脂から成る膜を挙げることができる。
励起光の種類は、一般式(1)で表される化合物等の混合する発光物質が吸収可能な波長領域に発光を示すものであれば、いずれの励起光でも用いることができる。例えば、熱陰極管や冷陰極管、無機エレクトロルミネッセンス(EL)等の蛍光性光源、有機EL素子光源、LED光源、白熱光源、あるいは太陽光等、いずれの励起光でも原理的には利用可能である。特に、LED光源からの光が好適な励起光である。ディスプレイや照明用途では、青色光の色純度を高められる点で、430nm~500nmの波長範囲の励起光を持つ青色LED光源からの光が、さらに好適な励起光である。
本発明の実施形態に係る光源ユニットは、少なくとも光源および上述の色変換フィルムを備える構成である。本発明の実施形態に係る光源ユニットに含まれる光源は、上述の励起光の発生源となるものである。光源と色変換フィルムとの配置方法については特に限定されず、光源と色変換フィルムとを密着させた構成を取ってもよいし、光源と色変換フィルムとを離したリモートフォスファー形式を取ってもよい。また、光源ユニットは、色純度を高める目的で、さらにカラーフィルターを備える構成を取ってもよい。
本発明の実施形態に係るディスプレイは、少なくとも、上述した色変換フィルムを備える。例えば、液晶ディスプレイ等のディスプレイには、バックライトユニットとして、上述した光源および色変換フィルム等を有する光源ユニットが用いられる。また、本発明の実施形態に係る照明装置は、少なくとも、上述した色変換フィルムを備える。例えば、この照明装置は、光源ユニットとしての青色LED光源と、この青色LED光源からの青色光をこれよりも長波長の光に変換する色変換フィルムとを組み合わせて、白色光を発光するように構成される。
本発明の実施形態において、発光素子は、陽極および陰極と、これら陽極と陰極との間に介在する有機層と、を備える。この発光素子の有機層は、電気エネルギーによって発光する。本発明の実施形態に係るピロメテンホウ素錯体は、この発光素子において、いずれの層に用いられてもよいが、高い蛍光量子収率を有しているため、この発光素子の発光層に用いることが好ましい。特に、当該ピロメテンホウ素錯体は、優れた蛍光量子収率を有していることから、上記発光層のドーパント材料として用いることが好ましい。
化合物の1H-NMRは、超伝導FTNMR EX-270(日本電子社製)を用い、重クロロホルム溶液にて測定を行った。
化合物の蛍光スペクトルは、F-2500形分光蛍光光度計(日立製作所社製)を用い、化合物をトルエンに1×10-6mol/Lの濃度で溶解させ、波長460nmで励起させた際の蛍光スペクトルを測定した。
化合物の発光量子収率は、絶対PL量子収率測定装置(Quantaurus-QY、浜松ホトニクス社製)を用い、化合物をトルエンに1×10-6mol/Lの濃度で溶解させ、波長460nmで励起させた際の発光量子収率を測定した。
以下に、本発明における合成例1の化合物G-23の合成方法について説明する。化合物G-23の合成方法では、3,5-ジブロモベンズアルデヒド(3.0g)、4-メトキシカルボニルフェニルボロン酸(5.3g)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.4g)、および炭酸カリウム(2.0g)をフラスコに入れ、窒素置換した。これに、脱気したトルエン(30mL)および脱気した水(10mL)を加え、4時間還流した。その後、反応溶液を室温まで冷却し、有機層を、分液した後に飽和食塩水で洗浄した。この有機層を硫酸マグネシウムで乾燥し、ろ過後、溶媒を留去した。得られた反応生成物をシリカゲルクロマトグラフィーにより精製し、3,5-ビス(4-メトキシカルボニルフェニル)ベンズアルデヒド(3.5g)を白色固体として得た。
1H-NMR(CDCl3,ppm):7.95-7.78(m,11H)、7.63-7.48(m,22H)、4.72(s,6H)、2.58(s,6H)、1.50(s,6H)
本発明の実施例1は、上述した実施形態に係るピロメテンホウ素錯体を発光材料(色変換材料)として用いた場合の実施例である。この実施例1では、バインダー樹脂としてアクリル樹脂を用い、このアクリル樹脂の100重量部に対して、発光材料として化合物G-1を0.25重量部、溶剤としてトルエンを400重量部、混合した。その後、これらの混合物を、遊星式撹拌・脱泡装置“マゼルスターKK-400”(クラボウ社製)を用いて300rpmで20分間撹拌・脱泡し、これにより、色変換組成物を得た。
本発明の実施例2~36および本発明に対する比較例1~6では、発光材料として後述の表1-1~1-3に記載した化合物(化合物G-2~G-36、G-101~G-106)を適宜用いたこと以外は、実施例1と同様にして、色変換フィルムを作製して評価した。実施例2~36、比較例1~6の発光材料および評価結果は、表1-1~1-3に示す。ただし、表中の量子収率(相対値)は、ピーク波長における量子収率であり、実施例1と同様に、比較例1における強度を1.00としたときの相対値である。また、光耐久性は、長時間であればあるほど好ましく、具体的には800時間以上であることが好ましい。
10 基材層
11 色変換層
12 バリアフィルム
Claims (8)
- 下記の一般式(3)で表される、分子量が1000以上の化合物であり、
前記一般式(3)におけるR1~R6のうち少なくとも2つは、下記の一般式(2)で表される基である、
ことを特徴とするピロメテンホウ素錯体。
- 前記一般式(3)において、R8およびR9のうち少なくとも1つはシアノ基である、
ことを特徴とする請求項1に記載のピロメテンホウ素錯体。 - 前記一般式(3)で表される化合物は、励起光を用いることによりピーク波長が500nm以上580nm未満の領域に観測される発光を呈する、
ことを特徴とする請求項1または2に記載のピロメテンホウ素錯体。 - 入射光を、その入射光よりも長波長の光に変換する色変換組成物であって、
請求項1~3のいずれか一つに記載のピロメテンホウ素錯体と、
バインダー樹脂と、
を含むことを特徴とする色変換組成物。 - 請求項4に記載の色変換組成物またはその硬化物からなる層を含む、
ことを特徴とする色変換フィルム。 - 光源と、
請求項5に記載の色変換フィルムと、
を備えることを特徴とする光源ユニット。 - 請求項5に記載の色変換フィルムを備える、
ことを特徴とするディスプレイ。 - 請求項5に記載の色変換フィルムを備える、
ことを特徴とする照明装置。
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