JP2010061824A - Color converting composition - Google Patents
Color converting composition Download PDFInfo
- Publication number
- JP2010061824A JP2010061824A JP2008223145A JP2008223145A JP2010061824A JP 2010061824 A JP2010061824 A JP 2010061824A JP 2008223145 A JP2008223145 A JP 2008223145A JP 2008223145 A JP2008223145 A JP 2008223145A JP 2010061824 A JP2010061824 A JP 2010061824A
- Authority
- JP
- Japan
- Prior art keywords
- group
- light
- color conversion
- aryl
- conversion composition
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 41
- 230000031700 light absorption Effects 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003518 tetracenes Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005013 aryl ether group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
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- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
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- 239000011230 binding agent Substances 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
本発明は、発光体からの発光をより長波長な光に変換する色変換組成物であって、ディスプレイ、照明、インテリア、標識、看板などの分野に利用可能な色変換組成物に関する。 The present invention relates to a color conversion composition that converts light emitted from a light emitter into light having a longer wavelength, and relates to a color conversion composition that can be used in the fields of displays, lighting, interiors, signs, signs, and the like.
色変換組方式によるマルチカラー化技術は有機ＥＬディスプレイなどへの応用が盛んに検討されている（非特許文献１）。色変換とは、発光体からの発光をより長波長な光へと変換することであり、たとえば青色発光を緑色や赤色発光へと変換することを表す。この色変換方式により、単色光源（例えば青色）から、青、緑、赤色の３原色が得られ、フルカラーディスプレイの作製が可能になる。 The application of multi-color technology using a color conversion set method to an organic EL display or the like has been actively studied (Non-Patent Document 1). The color conversion is to convert light emitted from the light emitter into light having a longer wavelength, for example, to convert blue light emission into green or red light emission. By this color conversion method, three primary colors of blue, green, and red are obtained from a single color light source (for example, blue), and a full color display can be manufactured.
発光体からの発光をより効率的に色変換するためには、高い色変換効率を有する色変換組成物を用いることが重要である。色変換組成物としては、これまでアリーレンビニレン骨格を繰り返し単位として有するポリマー（特許文献１）、シクロアルキルアルカン基を有するローダミン蛍光色素を分散した樹脂（特許文献２）、ナフトキノン誘導体をバインダー材料に分散したもの（特許文献３）、メタクリル酸メチル供重合体とクマリンあるいはローダミン色素、アクリレートからなるもの（特許文献４）が開示されている。
しかしながら従来の技術では、色変換効率および得られる発光色の色純度が充分では無かった。本発明は前記の課題を解決し、より高色変換効率・高色純度な色変換組成物を得ることを目的とする。 However, with the conventional technology, the color conversion efficiency and the color purity of the light emission color obtained are not sufficient. An object of the present invention is to solve the above problems and to obtain a color conversion composition having higher color conversion efficiency and higher color purity.
すなわち本発明は、発光体からの発光をより長波長な光に変換する色変換組成物であって、少なくとも一般式（１）で表されるピロメテン骨格を有する化合物もしくはその金属錯体と、４００ｎｍ〜６００ｎｍ領域に光吸収の長波長端を有する光吸収性化合物を含有することを特徴とする色変換組成物。 That is, the present invention is a color conversion composition that converts light emitted from a luminescent material into light having a longer wavelength, and at least a compound having a pyromethene skeleton represented by the general formula (1) or a metal complex thereof, A color conversion composition comprising a light-absorbing compound having a long wavelength end of light absorption in a 600 nm region.
（ここで、Ｒ１〜Ｒ７はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。Ｘは炭素原子または窒素原子であるが、窒素原子の場合には上記Ｒ７は存在しない。金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛および白金から選ばれる少なくとも一種である。） (Wherein R 1 to R 7 may be the same as or different from each other, hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether) Group, arylthioether group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents X is a carbon atom or a nitrogen atom, but in the case of a nitrogen atom, R 7 does not exist.The metal of the metal complex is boron, beryllium, magnesium, chromium, iron, (At least one selected from cobalt, nickel, copper, zinc and platinum.)
本発明によれば高色変換効率かつ高色純度な色変換組成物が得られる。 According to the present invention, a color conversion composition having high color conversion efficiency and high color purity can be obtained.
本発明の色変換組成物は、発光体からの発光をより長波長な光に変換する色変換組成物であって、少なくとも一般式（１）で表されるピロメテン骨格を有する化合物もしくはその金属錯体と、４００ｎｍ〜６００ｎｍ領域に光吸収の長波長端を有する光吸収性化合物を含有する。 The color conversion composition of the present invention is a color conversion composition that converts light emitted from a luminescent material into light having a longer wavelength, and is a compound having a pyromethene skeleton represented by general formula (1) or a metal complex thereof And the light absorptive compound which has the long wavelength end of light absorption in 400 nm-600 nm area | region is contained.
Ｒ１〜Ｒ７はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。Ｘは炭素原子または窒素原子であるが、窒素原子の場合には上記Ｒ７は存在しない。金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛および白金から選ばれる少なくとも一種である。 R 1 to R 7 may be the same or different from each other, and may be hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether. Ring structure formed between a group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents Chosen from. X is a carbon atom or a nitrogen atom. In the case of a nitrogen atom, R 7 does not exist. The metal of the metal complex is at least one selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum.
これらの置換基のうち、アルキル基とは、例えば、メチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、無置換でも置換されていてもかまわない。置換されている場合の置換基には特に制限は無く、例えば、アルキル基、アリール基、ヘテロアリール基等を挙げることができる。この点は、以下の記載にも共通する。また、アルキル基の炭素数は特に限定されないが、入手の容易性やコストの点から、１〜２０の範囲が好ましい。 Of these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and may be unsubstituted or substituted. There is no restriction | limiting in particular in the substituent in the case of being substituted, For example, an alkyl group, an aryl group, heteroaryl group etc. can be mentioned. This point is common to the following description. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 to 20 from the viewpoint of availability and cost.
また、シクロアルキル基とは、例えば、シクロプロピル基、シクロヘキシル基、ノルボルニル基、アダマンチル基などの飽和脂環式炭化水素基を示し、無置換でも置換されていてもかまわない。シクロアルキル基の炭素数は特に限定されないが、３〜２０の範囲が好ましい。 The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group, and may be unsubstituted or substituted. Although carbon number of a cycloalkyl group is not specifically limited, The range of 3-20 is preferable.
また、複素環基とは、例えば、ピラン環、ピペリジン環、環状アミドなどの炭素以外の原子を環内に有する脂肪族環からなる基を示し、無置換でも置換されていてもかまわない。複素環基の炭素数は特に限定されないが、２〜２０の範囲が好ましい。 The heterocyclic group refers to a group consisting of an aliphatic ring having atoms other than carbon, such as a pyran ring, piperidine ring, and cyclic amide, in the ring, and may be unsubstituted or substituted. Although carbon number of a heterocyclic group is not specifically limited, The range of 2-20 is preferable.
また、アルケニル基とは、例えば、ビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。アルケニル基の炭素数は特に限定されないが、２〜２０の範囲が好ましい。 Moreover, an alkenyl group shows the unsaturated aliphatic hydrocarbon group containing double bonds, such as a vinyl group, an allyl group, and a butadienyl group, for example, and this may be unsubstituted or substituted. Although carbon number of an alkenyl group is not specifically limited, The range of 2-20 is preferable.
また、シクロアルケニル基とは、例えば、シクロペンテニル基、シクロペンタジエニル基、シクロヘキセニル基などの二重結合を含む不飽和脂環式炭化水素基を示し、無置換でも置換されていてもかまわない。シクロアルケニル基の炭素数は特に限定されないが、３〜２０の範囲が好ましい。 The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may be unsubstituted or substituted. Absent. Although carbon number of a cycloalkenyl group is not specifically limited, The range of 3-20 is preferable.
また、アルキニル基とは、例えば、エチニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。アルキニル基の炭素数は特に限定されないが、２〜２０の範囲が好ましい。 The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may be unsubstituted or substituted. The number of carbon atoms of the alkynyl group is not particularly limited, but a range of 2 to 20 is preferable.
また、アルコキシ基とは、例えば、メトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。アルコキシ基の炭素数は特に限定されないが、１〜２０の範囲が好ましい。 The alkoxy group refers to, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an alkoxy group is not specifically limited, The range of 1-20 is preferable.
また、アルキルチオ基とは、アルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。 The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
また、アリールエーテル基とは、例えば、フェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。アリールエーテル基の炭素数は特に限定されないが、６〜４０の範囲が好ましい。 The aryl ether group refers to, for example, an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an aryl ether group is not specifically limited, The range of 6-40 is preferable.
また、アリールチオエーテル基とは、アリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。 The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom.
また、アリール基とは、例えば、フェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示す。アリール基は、無置換でも置換されていてもかまわない。アリール基の炭素数は特に限定されないが、６〜４０の範囲が好ましい。 Moreover, an aryl group shows aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group, for example. The aryl group may be unsubstituted or substituted. Although carbon number of an aryl group is not specifically limited, The range of 6-40 is preferable.
また、ヘテロアリール基とは、例えば、フラニル基、チオフェニル基、オキサゾリル基、ピリジル基、キノリニル基などの炭素以外の原子を環内に有する芳香族基を示し、無置換でも置換されていてもかまわない。ヘテロアリール基の炭素数は、２〜３０の範囲が好ましい。 The heteroaryl group refers to an aromatic group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, or a quinolinyl group, which may be unsubstituted or substituted. Absent. The carbon number of the heteroaryl group is preferably in the range of 2-30.
ハロゲンとは、フッ素、塩素、臭素およびヨウ素から選ばれた原子を示す。 Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.
カルボキシル基、カルバモイル基およびアミノ基は、さらに該置換基の水素が置換されていても置換されていなくてもよい。置換基としては、例えばアルキル基、シクロアルキル基、アリール基、ヘテロアリール基などが挙げられ、これらの置換基がさらに置換されていてもよい。 The carboxyl group, carbamoyl group and amino group may or may not be further substituted with hydrogen in the substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.
カルボニル基、オキシカルボニル基およびホスフィンオキサイド基におけるピロメテン骨格との結合手以外の結合手は、アルキル基、シクロアルキル基、アリール基およびヘテロアリール基から選ばれる置換基が結合している。 A substituent selected from an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group is bonded to a bond other than the bond to the pyromethene skeleton in the carbonyl group, oxycarbonyl group, and phosphine oxide group.
シリル基とは、例えば、トリメチルシリル基などのケイ素原子への結合を有する官能基を示し、無置換でも置換されていてもかまわない。シリル基の炭素数は特に限定されないが、３以上２０以下の範囲が好ましい。また、ケイ素数は、１以上６以下の範囲が好ましい。 The silyl group refers to, for example, a functional group having a bond to a silicon atom such as a trimethylsilyl group, and may be unsubstituted or substituted. Although carbon number of a silyl group is not specifically limited, The range of 3-20 is preferable. The silicon number is preferably in the range of 1 to 6.
隣接基との間に形成される環構造とは、前記一般式（１）で説明すると、Ｒ１〜Ｒ６の中から選ばれる任意の隣接２置換基（例えばＲ１とＲ２）が互いに結合して、共役または非共役の環構造を形成するものである。これら環構造は環内構造に窒素、酸素および硫黄原子から選ばれた原子を含んでいてもよいし、さらに別の環と縮合していてもよい。これら環構造を構成する原子が炭素原子と水素原子のみであると、優れた耐熱性が得られるため好ましい。 When the ring structure formed between adjacent groups is described in the general formula (1), any two adjacent substituents selected from R 1 to R 6 (for example, R 1 and R 2 ) are mutually bonded. They are bonded to form a conjugated or non-conjugated ring structure. These ring structures may contain an atom selected from nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring. It is preferable that the atoms constituting these ring structures are only carbon atoms and hydrogen atoms because excellent heat resistance can be obtained.
上述の一般式（１）で示したピロメテン骨格を有する化合物もしくはその金属錯体のなかでも、より高い蛍光量子収率が得られることから、下記一般式（２）に示す金属錯体がより好ましい。 Among the compounds having a pyromethene skeleton represented by the above general formula (1) or a metal complex thereof, a metal complex represented by the following general formula (2) is more preferable because a higher fluorescence quantum yield is obtained.
Ｒ３０〜Ｒ３６はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。Ｒ３７およびＲ３８は同じでも異なっていてもよく、ハロゲン、水素、アルキル、アリールおよび複素環基から選ばれる。Ｘは炭素原子または窒素原子であるが、窒素原子の場合には上記Ｒ３６は存在しない。なおこれらの置換基の説明は上述したものと同じである。 R 30 to R 36 may be the same as or different from each other, and hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether Ring structure formed between a group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents Chosen from. R 37 and R 38 may be the same or different and are selected from halogen, hydrogen, alkyl, aryl and heterocyclic groups. X is a carbon atom or a nitrogen atom, but in the case of a nitrogen atom, R 36 does not exist. The explanation of these substituents is the same as described above.
上記のような一般式（２）で表されるピロメテン金属錯体としては、特に限定はされないが以下の具体例を挙げることができる。 Although it does not specifically limit as a pyromethene metal complex represented by the above General formula (2), The following specific examples can be given.
本発明における色変換組成物は、上記ピロメテン骨格を有する化合物もしくはその金属錯体に加えて、光吸収性化合物を含有する。光吸収性化合物は、光源からの光エネルギー吸収し、ピロメテン骨格を有する化合物もしくはその金属錯体にエネルギー移動せしめる役割を担う。ピロメテン骨格を有する化合物もしくはその金属錯体は光吸収性化合物から移動されたエネルギーにより発光する。ピロメテン骨格を有する化合物もしくはその金属錯体の高い発光能力を効率的に発現せしめるために、光吸収性化合物は、４００ｎｍ〜６００ｎｍ領域に光吸収の長波長端を有することが必要である。さらに可視領域における発光を効率的に得るためには、４００〜５６０ｎｍ領域に光吸収の長波長端を有することが望ましい。ここで光吸収の長波長端とは、３００ｎｍ〜８００ｎｍの近紫外領域〜可視光領域における光吸収スペクトルの長波長端を言う。測定する方法としては、石英ガラス上に１０ｎｍ〜１００ｎｍ程度の厚さに膜を形成した後に、大気中雰囲気にて、紫外線可視光分光光度計を用いて簡単に測定することができる。 The color conversion composition in the present invention contains a light-absorbing compound in addition to the compound having a pyromethene skeleton or a metal complex thereof. The light-absorbing compound plays a role of absorbing light energy from a light source and transferring energy to a compound having a pyromethene skeleton or a metal complex thereof. A compound having a pyromethene skeleton or a metal complex thereof emits light by energy transferred from the light-absorbing compound. In order to efficiently express the high light-emitting ability of a compound having a pyromethene skeleton or a metal complex thereof, the light-absorbing compound needs to have a long wavelength end of light absorption in the 400 nm to 600 nm region. Furthermore, in order to efficiently obtain light emission in the visible region, it is desirable to have a long wavelength end of light absorption in the 400 to 560 nm region. Here, the long wavelength end of light absorption refers to the long wavelength end of the light absorption spectrum in the near ultraviolet region to visible light region of 300 nm to 800 nm. As a measuring method, after forming a film with a thickness of about 10 nm to 100 nm on quartz glass, it can be easily measured using an ultraviolet visible light spectrophotometer in the atmosphere.
光吸収性化合物の具体例としては、（ポリ）チオフェン誘導体、アルミキノリン錯体等の金属錯体、芳香族アミン、カルバゾール誘導体、フェナントロリン誘導体、縮合多環化合物などを好適に用いることができるが、ピロメテン骨格を有する化合物もしくはその金属錯体とのエネルギー移動の相性の観点から、特に縮合多環化合物であることが好ましい。縮合多環化合物とは、縮合多環を含む有機化合物であり、縮合多環とは、２つ以上の単環がそれぞれの環の辺を互いに縮合してできる多環のことであり、ペンタレン、インデン、ナフタレン、アズレン、ヘプタレン、ビフェニレン、ａｓ―インダセン、ｓ−インダセン、アセナフチレン、フルオレン、フェナレン、フェナンスレン、アントラセン、フルオランテン、アセフェンスレン、アセアントリレン、トリフェニレン、ピレン、クリセン、ナフタセン、プレイアデン、ピセン、ペリレン、ペンタフェン、ペンタセン、テトラフェニレン、ヘキサフェンなどがあげられる。縮合環数は特に制限は無いが、４環以上であるとき、色変換組成物の熱的安定性が高くなり好ましい。中でも、ナフタセン誘導体及びピレン誘導体がピロメテン骨格を有する化合物もしくはその金属錯体との相性に優れる。 ここで本発明において用いる一般式（３）で表されるナフタセン誘導体について詳細に説明する。 Specific examples of the light absorbing compound include (poly) thiophene derivatives, metal complexes such as aluminum quinoline complexes, aromatic amines, carbazole derivatives, phenanthroline derivatives, condensed polycyclic compounds, and the like. From the viewpoint of compatibility of energy transfer with a compound having a hydrogen atom or a metal complex thereof, a condensed polycyclic compound is particularly preferable. The condensed polycyclic compound is an organic compound containing a condensed polycyclic ring, and the condensed polycyclic ring is a polycyclic ring formed by condensing two or more monocycles with each other, and pentalene, Indene, naphthalene, azulene, heptalene, biphenylene, as-indacene, s-indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acefenthrene, acanthrylene, triphenylene, pyrene, chrysene, naphthacene, preaden, picene Perylene, pentaphen, pentacene, tetraphenylene, hexaphen and the like. The number of condensed rings is not particularly limited, but is preferably 4 or more because the thermal stability of the color conversion composition is increased. Among these, naphthacene derivatives and pyrene derivatives are excellent in compatibility with a compound having a pyromethene skeleton or a metal complex thereof. Here, the naphthacene derivative represented by the general formula (3) used in the present invention will be described in detail.
Ｒ８〜Ｒ１９はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。これらの置換基の説明は上述したものと同じである。 R 8 to R 19 may be the same or different and are each hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether Ring structure formed between a group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents Chosen from. The explanation of these substituents is the same as described above.
一般式（３）で表されるナフタセン誘導体のなかでも、安定な薄膜形成の観点から、特にＲ８〜Ｒ１９のうち少なくとも一つがアリール基であることが好ましい。これにより色変換組成物の熱的安定性を向上させることができる。さらに、光吸収性化合物とピロメテン骨格を有する化合物もしくはその金属錯体との相互作用の低減観点からはＲ８〜Ｒ１９のうち少なくとも二つがアリール基であることが好ましい。相互作用の低減により、色変換効率がより向上する。この場合、Ｒ１２とＲ１３、Ｒ１２とＲ１９、Ｒ１２とＲ１８、Ｒ１２とＲ１３とＲ１８、あるいはＲ１２とＲ１３とＲ１８とＲ１９のいずれかの組み合わせ位置へのアリール基導入が好ましい。なかでも、合成の容易さから下記一般式（５）で表されるナフタセン誘導体が好適に用いられる。 Among the naphthacene derivatives represented by the general formula (3), at least one of R 8 to R 19 is particularly preferably an aryl group from the viewpoint of forming a stable thin film. Thereby, the thermal stability of the color conversion composition can be improved. Furthermore, from the viewpoint of reducing the interaction between the light-absorbing compound and the compound having a pyromethene skeleton or a metal complex thereof, at least two of R 8 to R 19 are preferably aryl groups. By reducing the interaction, the color conversion efficiency is further improved. In this case, R 12 and R 13 , R 12 and R 19 , R 12 and R 18 , R 12 and R 13 and R 18 , or R 12 and R 13 , R 18 and R 19 are combined into any combination position. Aryl group introduction is preferred. Of these, a naphthacene derivative represented by the following general formula (5) is preferably used because of ease of synthesis.
ここでＲ３９〜Ｒ５８は、それぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。 Here, R 39 to R 58 may be the same as or different from each other, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group. , Arylthioether group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents Selected from ring structures.
このようなアリール基を有するナフタセン誘導体としては具体例として以下を示すが、これらに限定されない。 Specific examples of such naphthacene derivatives having an aryl group are shown below, but are not limited thereto.
上記一般式（５）の中でも、ナフタセン誘導体の分子構造が嵩高くなり、分子間相互作用が低減されているものが、薄膜形成能にさらに優れ、高色変換効率かつ高い熱的安定性が得られることから、より好適に用いられる。嵩高い分子構造を有するものとしては、Ｒ４３〜Ｒ４７およびＲ５４〜Ｒ５８のうち少なくとも一つがアリール基であるか、隣接置換基との間で共役環構造を有する誘導体が挙げられる。さらにＲ４３〜Ｒ４７のうちの２カ所以上もしくはＲ５４〜Ｒ５８のうちの２カ所以上がアリール基から選ばれることが嵩高い分子構造の点でより好ましい。また、Ｒ４３、Ｒ４７、Ｒ５４およびＲ５８のうち少なくとも一つが水素以外の置換基から選ばれる場合、あるいはＲ４３とＲ４４、Ｒ４６とＲ４７、Ｒ５４とＲ５５およびＲ５７とＲ５８のうちの少なくとも１カ所で環構造を形成する場合も、ナフタセン骨格に導入したアリール基がナフタセン骨格に対し捻れた関係となり、嵩高い分子構造となるので、好ましい例として挙げることができる。 Among the above general formulas (5), the molecular structure of the naphthacene derivative is bulky and the intermolecular interaction is reduced, which is further excellent in thin film forming ability, high color conversion efficiency and high thermal stability. Therefore, it is used more suitably. Examples of those having a bulky molecular structure include derivatives in which at least one of R 43 to R 47 and R 54 to R 58 is an aryl group or has a conjugated ring structure with an adjacent substituent. Furthermore, it is more preferable in terms of the bulky molecular structure that two or more of R 43 to R 47 or two or more of R 54 to R 58 are selected from an aryl group. Further, when at least one of R 43 , R 47 , R 54 and R 58 is selected from substituents other than hydrogen, or R 43 and R 44 , R 46 and R 47 , R 54 and R 55 and R 57 In the case where a ring structure is formed in at least one of R 58 , the aryl group introduced into the naphthacene skeleton is twisted with respect to the naphthacene skeleton, resulting in a bulky molecular structure.
また、Ｒ４３〜Ｒ４７に導入される置換基とＲ５４〜Ｒ５８に導入される置換基が異なり、分子構造が非対称になったものも、嵩高い分子構造を有するものと同様の効果が得られるので好ましい。 In addition, the substituent introduced into R 43 to R 47 and the substituent introduced into R 54 to R 58 are different and the molecular structure is asymmetrical, but the same effect as that having a bulky molecular structure can be obtained. Since it is obtained, it is preferable.
さらに、上記誘導体においては、構造異性体が存在しない誘導体が、発光特性の再現性の観点で好ましい。ここでいう構造異性体とは、たとえばナフタセン骨格に対しねじれの関係にある置換基を二つ導入した際に、導入置換基がナフタセン骨格平面に対し、シスおよびトランスの関係を取りうることを指す。具体例を挙げると、以下のようなシス体およびトランス体構造を取り得る。 Furthermore, in the above derivatives, derivatives having no structural isomer are preferable from the viewpoint of reproducibility of the light emission characteristics. The structural isomer here means that, for example, when two substituents having a twisted relationship with respect to the naphthacene skeleton are introduced, the introduced substituent can have a cis and trans relationship with the naphthacene skeleton plane. . As specific examples, the following cis- and trans-isomer structures can be taken.
シス体およびトランス体が共存すると、それらの比率により素子の発光特性の変化が起こり、発光特性の再現性が低下しうる。これを防ぐためには、ナフタセン誘導体を十分に精製して、一つの構造異性体のみを含むようにするなど、複雑な製造工程が必要になる。さらに、いったん精製した後でも、異性化によって、構造異性体の比率が変化しうる。以上のように、構造異性体が存在する誘導体は、製造コストが高くなりがちであり、また、発光特性の再現性が低下しうるので好ましくない。 When the cis form and the trans form coexist, the light emission characteristics of the device change depending on their ratio, and the reproducibility of the light emission characteristics may be reduced. In order to prevent this, a complicated production process such as sufficiently purifying the naphthacene derivative to contain only one structural isomer is required. Furthermore, even after purification, the ratio of structural isomers can be changed by isomerization. As described above, a derivative in which a structural isomer exists is not preferable because the production cost tends to be high and the reproducibility of the light emission characteristics can be lowered.
このような構造異性体が存在しないナフタセン誘導体としては、置換基が、結合軸に対して対称な置換基であるナフタセン誘導体が上げられる。具体的には、上記の例のうち、化合物［９４］〜［９６］、［１００］〜［１０８］などが上げられる。 Examples of the naphthacene derivative in which such a structural isomer does not exist include a naphthacene derivative in which the substituent is a symmetric substituent with respect to the bond axis. Specifically, among the above examples, compounds [94] to [96], [100] to [108] and the like are listed.
ここで本発明において用いる一般式（４）で表されるピレン誘導体について詳細に説明する。 Here, the pyrene derivative represented by the general formula (4) used in the present invention will be described in detail.
Ｒ２０〜Ｒ２９はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基、ならびに隣接置換基との間に形成される環構造の中から選ばれる。これらの置換基の説明は上述したものと同じである。 R 20 to R 29 may be the same as or different from each other, and hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether Ring structure formed between a group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, silyl group, phosphine oxide group, and adjacent substituents Chosen from. The explanation of these substituents is the same as described above.
一般式（４）の中でもピレン誘導体の分子構造が嵩高くなり、分子間相互作用が低減されているものが、薄膜形成能にさらに優れ、高色変換効率かつ高い熱的安定性が得られることから、より好適に用いられる。嵩高い分子構造を有するものとしては、特に限定されないが、具体的には以下のような例が挙げられる。 Among the general formulas (4), the molecular structure of the pyrene derivative is bulky and the intermolecular interaction is reduced, which further improves the thin film forming ability, provides high color conversion efficiency and high thermal stability. Therefore, it is more preferably used. Although it does not specifically limit as what has a bulky molecular structure, Specifically, the following examples are mentioned.
本発明における色変換組成物は、少なくともピロメテン骨格を有する化合物もしくはその金属錯体および光吸収性化合物を含有することを特徴としているが、その製造方法としては、抵抗加熱式蒸着法などの真空蒸着法、レーザー転写法などの乾式プロセスや、適当な溶媒や低粘度樹脂成分に上記材料を混合した後に、スピンコート法やインクジェット法、印刷法などの湿式プロセスを用いるなど、公知の技術を適宜用いることができる。真空蒸着法やレーザー転写法を用いる際には、上記材料を複数の蒸着源から同時に蒸着する方法や、あらかじめ混合しておいた上記材料を１つの蒸着源から蒸着する方法などいずれの方法を用いることができる。 The color conversion composition in the present invention is characterized by containing at least a compound having a pyromethene skeleton or a metal complex thereof and a light-absorbing compound, and the production method thereof is a vacuum deposition method such as a resistance heating deposition method. , Using a known technique such as a dry process such as a laser transfer method or a wet process such as a spin coating method, an ink jet method, or a printing method after mixing the above materials with an appropriate solvent or low viscosity resin component. Can do. When using a vacuum evaporation method or a laser transfer method, any method such as a method of simultaneously evaporating the material from a plurality of evaporation sources or a method of evaporating the material mixed in advance from one evaporation source is used. be able to.
本発明における色変換組成物は、ピロメテン骨格を有する化合物もしくはその金属錯体と光吸収性化合物以外に、必要に応じてその他の材料を適宜添加することができる。例えば、光吸収性化合物からピロメテン骨格を有する化合物もしくはその金属錯体へのエネルギー移動効率を更に高めるために、ルブレンなどのアシストドーパントを添加したり、ピロメテン骨格を有する化合物もしくはその金属錯体からの発光色以外の発光色を加味したい場合はクマリン系色素，ペリレン系色素，フタロシアニン系色素，スチルベン系色素，シアニン系色素，ポリフェニレン系色素，ローダミン系色素などの蛍光材料を添加することができる。また、色変換組成物の熱的特性や形状安定性を向上させるために、バインダー樹脂を加えることができる。バインダー樹脂としては、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、ポリ塩化ビニル樹脂、メラミン樹脂、フェノール樹脂、アルキド樹脂、エポキシ樹脂、ポリウレタン樹脂、ポリエステル樹脂、マレイン酸樹脂、ポリアミド樹脂のオリゴマーまたはポリマー、ポリメチルメタクリレート、ポリアクリレート、ポリカーボネート、ポリビニルアルコール、ポリビニルピロリドン、ヒドロキシエチルセルロース、カルボキシメチルセルロース樹脂、芳香族スルホンアミド樹脂、尿素樹脂、ベンゾグアナミン樹脂、ビリジルビニル樹脂等などの公知材料を用いることができる。 In addition to the compound having a pyromethene skeleton or a metal complex thereof and a light-absorbing compound, other materials can be appropriately added to the color conversion composition in the present invention as necessary. For example, in order to further increase the energy transfer efficiency from a light-absorbing compound to a compound having a pyromethene skeleton or a metal complex thereof, an assist dopant such as rubrene is added, or a light emission color from a compound having a pyromethene skeleton or a metal complex thereof. When it is desired to add a light emission color other than the above, fluorescent materials such as coumarin dyes, perylene dyes, phthalocyanine dyes, stilbene dyes, cyanine dyes, polyphenylene dyes, rhodamine dyes can be added. In addition, a binder resin can be added in order to improve the thermal properties and shape stability of the color conversion composition. Examples of the binder resin include photo-curable resist materials having reactive vinyl groups such as acrylic acid, methacrylic acid, polyvinyl cinnamate, and ring rubber, polyvinyl chloride resin, melamine resin, phenol resin, and alkyd resin. , Epoxy resin, polyurethane resin, polyester resin, maleic acid resin, polyamide resin oligomer or polymer, polymethyl methacrylate, polyacrylate, polycarbonate, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxyethyl cellulose, carboxymethyl cellulose resin, aromatic sulfonamide resin, urea Known materials such as resin, benzoguanamine resin, and biridyl vinyl resin can be used.
ピロメテン骨格を有する化合物もしくはその金属錯体と光吸収性化合物の混合比は、ピロメテン骨格を有する化合物もしくはその金属錯体を光吸収性化合物に対して、０．１重量％から１０重量％の範囲で混合させることがエネルギー移動効率の観点で望ましいが、０．３重量％から５重量％の範囲にある時、さらに高い効率が得られる。混合比が小さすぎる時はピロメテン骨格を有する化合物もしくはその金属錯体が光吸収性化合物からのエネルギーを受けきれなくなり、混合比が大きすぎる時はピロメテン骨格を有する化合物もしくはその金属錯体が濃度消光を起こし発光特性が小さくなる。 The mixing ratio of the compound having a pyromethene skeleton or a metal complex thereof and the light absorbing compound is such that the compound having the pyromethene skeleton or the metal complex thereof is mixed in the range of 0.1 wt% to 10 wt% with respect to the light absorbing compound. Although it is desirable from the viewpoint of energy transfer efficiency, higher efficiency is obtained when it is in the range of 0.3 wt% to 5 wt%. When the mixing ratio is too small, the compound having a pyromethene skeleton or its metal complex cannot receive the energy from the light-absorbing compound, and when the mixing ratio is too large, the compound having the pyromethene skeleton or its metal complex causes concentration quenching. Luminous characteristics are reduced.
色変換組成物の厚さは、混合する材料の種類や混合比により最適値が異なるため一概には言えないが、１０ｎｍから１００μｍの範囲にあることが望ましい。より好ましくは、１００ｎｍ〜１０μｍの範囲にある時、発光体からの発光の吸収と色変換組成物からの発光の比率（エネルギー変換効率）が最も高くなるため、好ましい。 The thickness of the color conversion composition varies depending on the type of material to be mixed and the mixing ratio, and thus cannot be generally specified. However, the thickness is preferably in the range of 10 nm to 100 μm. More preferably, when the thickness is in the range of 100 nm to 10 μm, the ratio of absorption of light emitted from the light emitter to light emitted from the color conversion composition (energy conversion efficiency) is the highest.
発光体の種類は、光吸収性化合物が吸収可能な波長領域に発光を示す発光体であればいずれの発光体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ＥＬなどの蛍光性光源、発光ダイオードなどの半導体素子、白熱光源、あるいは太陽光などいずれの発光体でも原理的には利用可能であるが、特には有機ＥＬ素子が好適な発光体である。有機ＥＬ素子は、薄型・軽量な面光源であると言う特徴を持つため、本発明の色変換組成物と組み合わせる時、携帯可能なディスプレイを作製することが可能になると言う点で、最も好適な発光体であると言える。 As the type of the illuminant, any illuminant that can emit light in a wavelength region that can be absorbed by the light-absorbing compound can be used. For example, any light emitter such as a hot cathode tube, a cold cathode tube, a fluorescent light source such as inorganic EL, a semiconductor element such as a light emitting diode, an incandescent light source, or sunlight can be used in principle. An EL element is a suitable light emitter. Since the organic EL element has a feature that it is a thin and light surface light source, it is most suitable in that it can be used to produce a portable display when combined with the color conversion composition of the present invention. It can be said that it is a light emitter.
以下、実施例をあげて本発明を説明するが、本発明はこれらの実施例によって限定されるものではない。なお、下記の各実施例にある化合物の番号は上記に記載した化合物の番号を指すものである。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited by these Examples. In addition, the number of the compound in each following Example points out the number of the compound described above.
実施例１
色変換組成物の調整
石英基板（２０ｍｍ×２０ｍｍ×０．７ｍｍ厚）を “セミコクリン（登録商標）５６”（フルウチ化学（株）製）で１５分間超音波洗浄してから、超純水で洗浄した。次いでＵＶ−オゾン洗浄機にて３０分間ドライ洗浄をしてから、真空蒸着機内に設置して装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱式蒸着法によって、光吸収性化合物として光吸収の長波長端が４９６ｎｍのピレン誘導体［１５７］と、ピロメテン骨格を有する金属錯体として[２１]を、異なる蒸着源から共蒸着法により混合膜を作製し、色変換組成物とした。この時、光吸収性化合物に対してピロメテン骨格を有する金属錯体を、膜厚モニター値で、１ｗｔ％になるように、蒸着レートを調節した。
Example 1
Preparation of color conversion composition A quartz substrate (20 mm × 20 mm × 0.7 mm thickness) was ultrasonically cleaned with “Semicocrine (registered trademark) 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water. did. Next, after dry-cleaning for 30 minutes with a UV-ozone cleaner, it was placed in a vacuum deposition machine and evacuated until the degree of vacuum in the apparatus was 5 × 10 −4 Pa or less. By a resistance heating vapor deposition method, a pyrene derivative [157] having a light absorption long wavelength end of 496 nm as a light absorbing compound and [21] as a metal complex having a pyromethene skeleton are mixed from different vapor deposition sources by a co-evaporation method. Was prepared as a color conversion composition. At this time, the deposition rate was adjusted so that the metal complex having a pyromethene skeleton with respect to the light-absorbing compound would be 1 wt% in terms of the film thickness monitor value.
色変換組成物の変換効率の評価
上記によって得られた色変換組成物の光透過率をＵＶ分光光度計（Ｕ−３０１０、日立製作所）によって測定した。このうち、波長４５０ｎｍにおける光透過率（Ｔ１）は、３４（％）であった。次に、同色変換組成物を波長４５０ｎｍにて光励起する際の発光スペクトルを分光蛍光光度計（Ｆ−２５００、日立製作所）によって測定した。その結果、発光スペクトルはピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また、同発光スペクトルの面積値（発光エネルギーに相当：Ｅ１）は、１０１９７６（無次元数）であった。すなわち、すべての光が色変換組成物に吸収（透過率＝０％）される際の発光エネルギー（計算値）Ｅ０は、Ｅ０＝Ｅ１／（１００−Ｔ１）×１００、となり、この場合は、１５４５０９となる。
Evaluation of Conversion Efficiency of Color Conversion Composition The light transmittance of the color conversion composition obtained as described above was measured with a UV spectrophotometer (U-3010, Hitachi, Ltd.). Among these, the light transmittance (T1) at a wavelength of 450 nm was 34 (%). Next, the emission spectrum when the same color conversion composition was photoexcited at a wavelength of 450 nm was measured with a spectrofluorometer (F-2500, Hitachi, Ltd.). As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The area value of the emission spectrum (corresponding to emission energy: E1) was 101976 (dimensionless number). That is, the emission energy (calculated value) E0 when all the light is absorbed by the color conversion composition (transmittance = 0%) is E0 = E1 / (100−T1) × 100. In this case, 154509.
以下、本実施例１の色変換効率（上記Ｅ０＝１５４５０９の時）を１．０とする場合の、種々の材料の組み合わせで測定した色変換効率の値を相対比較した。本評価方法によれば、様々な光透過率を有する光変換組成物の色変換効率を相対評価（比較）することができる。 Hereinafter, when the color conversion efficiency of Example 1 (when E0 = 154509) is set to 1.0, the values of color conversion efficiency measured with various combinations of materials were compared. According to this evaluation method, the color conversion efficiency of the light conversion composition having various light transmittances can be relatively evaluated (compared).
実施例２
ピロメテン骨格を有する金属錯体として[３７]を用いる以外は実施例１と同様の方法によって評価を実施した。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は１．０であった。
Example 2
Evaluation was performed in the same manner as in Example 1 except that [37] was used as the metal complex having a pyromethene skeleton. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 1.0.
実施例３
光吸収性化合物として光吸収の長波長端が４５２ｎｍのピレン誘導体［１５８］を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長４００ｎｍの値を使用し、波長４００ｎｍの励起光にて色変換組成物を発光させた。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．８５であった。
Example 3
Evaluation was performed in the same manner as in Example 1 except that a pyrene derivative [158] having a long wavelength end of light absorption of 452 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 400 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 400 nm. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.85.
実施例４
光吸収性化合物として光吸収の長波長端が５２５ｎｍのナフタセン誘導体［９７］を用いる以外は実施例１と同様の方法によって評価を実施した。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．９２であった。
実施例５
光吸収性化合物として光吸収の長波長端が５２５ｎｍのナフタセン誘導体［106］を用いる以外は実施例１と同様の方法によって評価を実施した。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．９５であった。
Example 4
Evaluation was performed in the same manner as in Example 1 except that a naphthacene derivative [97] having a light absorption long wavelength end of 525 nm was used as the light absorbing compound. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.92.
Example 5
Evaluation was performed in the same manner as in Example 1 except that a naphthacene derivative [106] having a long wavelength end of light absorption of 525 nm was used as the light absorbing compound. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.95.
実施例６
光吸収性化合物として光吸収の長波長端が４２３ｎｍの下記化学構造式（Ｃ−１）で示されるアントラセン誘導体を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長４００ｎｍの値を使用し、波長４００ｎｍの励起光にて色変換組成物を発光させた。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．７３であった。
Example 6
Evaluation was performed in the same manner as in Example 1 except that an anthracene derivative represented by the following chemical structural formula (C-1) having a light absorption long wavelength end of 423 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 400 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 400 nm. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.73.
実施例７
光吸収性化合物として光吸収の長波長端が５４８ｎｍの下記化学構造式（Ｃ−２）で示されるチオフェン誘導体を用いる以外は実施例１と同様の方法によって評価を実施した。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．６４であった。
Example 7
Evaluation was performed in the same manner as in Example 1 except that a thiophene derivative represented by the following chemical structural formula (C-2) having a long wavelength end of light absorption of 548 nm was used as the light absorbing compound. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.64.
実施例８
光吸収性化合物として光吸収の長波長端が４３４ｎｍの下記化学構造式（Ｃ−３）で示されるアルミキノリン錯体を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長４００ｎｍの値を使用し、波長４００ｎｍの励起光にて色変換組成物を発光させた。その結果、発光スペクトルは、ピロメテン骨格を有する金属錯体に由来するきれいな赤色発光スペクトルを示した。また色変換効率（実施例１に対する相対値）は０．７７であった。
Example 8
Evaluation was performed in the same manner as in Example 1 except that an aluminum quinoline complex represented by the following chemical structural formula (C-3) having a long wavelength end of light absorption of 434 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 400 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 400 nm. As a result, the emission spectrum showed a clean red emission spectrum derived from a metal complex having a pyromethene skeleton. The color conversion efficiency (relative to Example 1) was 0.77.
比較例１
光吸収性化合物として光吸収の長波長端が３６６ｎｍの下記化学構造式（Ｃ−４）で示されるカルバゾール誘導体を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長３３０ｎｍの値を使用し、波長３３０ｎｍの励起光にて色変換組成物を発光させた。その結果、また発光スペクトルはピロメテン骨格を有する金属錯体に由来する赤色発光と、光吸収性化合物有する化合物に由来する近紫外発光が観測された。このように光吸収性化合物からピロメテン骨格を有する金属錯体へのエネルギー移動が充分に起こらず、色変換効率（実施例１に対する相対値）も０．１１と充分な値が得られなかった。
Comparative Example 1
Evaluation was performed in the same manner as in Example 1 except that a carbazole derivative represented by the following chemical structural formula (C-4) having a light absorption long wavelength end of 366 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 330 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 330 nm. As a result, in the emission spectrum, red emission derived from a metal complex having a pyromethene skeleton and near ultraviolet emission derived from a compound having a light absorbing compound were observed. Thus, the energy transfer from the light absorbing compound to the metal complex having a pyromethene skeleton did not occur sufficiently, and the color conversion efficiency (relative value with respect to Example 1) was also not sufficient as 0.11.
比較例２
光吸収性化合物として光吸収の長波長端が３７７ｎｍの下記化学構造式（Ｃ−５）で示されるフェナントロリン誘導体を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長３３０ｎｍの値を使用し、波長３３０ｎｍの励起光にて色変換組成物を発光させた。その結果、また発光スペクトルはピロメテン骨格を有する金属錯体に由来する赤色発光と、光吸収性化合物有する化合物に由来する近紫外発光が観測された。このように光吸収性化合物からピロメテン骨格を有する金属錯体へのエネルギー移動が充分に起こらず、色変換効率（実施例１に対する相対値）も０．１４と充分な値が得られなかった。
Comparative Example 2
Evaluation was performed in the same manner as in Example 1 except that a phenanthroline derivative represented by the following chemical structural formula (C-5) having a light absorption long wavelength end of 377 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 330 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 330 nm. As a result, in the emission spectrum, red emission derived from a metal complex having a pyromethene skeleton and near ultraviolet emission derived from a compound having a light absorbing compound were observed. Thus, the energy transfer from the light absorbing compound to the metal complex having a pyromethene skeleton did not occur sufficiently, and the color conversion efficiency (relative value with respect to Example 1) was 0.14, which was not a sufficient value.
比較例３
光吸収性化合物として光吸収の長波長端が７８０ｎｍの下記化学構造式（Ｃ−６）で示される銅フタロシアニン錯体を用いる以外は実施例１と同様の方法によって評価を実施した。ただし光透過率は波長６００ｎｍの値を使用し、波長６００ｎｍの励起光にて色変換組成物を発光させた。その結果、色変換組成物からの発光は観測されなかった。（色変換効率は０であった。）
Comparative Example 3
Evaluation was performed in the same manner as in Example 1 except that a copper phthalocyanine complex represented by the following chemical structural formula (C-6) having a long wavelength end of light absorption of 780 nm was used as the light absorbing compound. However, the light transmittance was a value having a wavelength of 600 nm, and the color conversion composition was caused to emit light with excitation light having a wavelength of 600 nm. As a result, no luminescence from the color conversion composition was observed. (The color conversion efficiency was 0.)
比較例４
光吸収性化合物として光吸収の長波長端が４９６ｎｍのピレン誘導体［１５７］と、下記化学構造式（Ｃ−７）で示される化合物を用いる以外は実施例１と同様の方法によって評価を実施した。その結果、また発光スペクトルは化合物（Ｃ−７）に由来する赤色発光は観測されたが、色変換効率（実施例１に対する相対値）は０．２９と充分な値が得られなかった。
Comparative Example 4
Evaluation was performed in the same manner as in Example 1 except that a pyrene derivative [157] having a long wavelength end of light absorption of 496 nm and a compound represented by the following chemical structural formula (C-7) were used as the light-absorbing compound. . As a result, although red emission derived from the compound (C-7) was observed in the emission spectrum, the color conversion efficiency (relative value to Example 1) was 0.29, which was not a sufficient value.
Claims (7)
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