JP2007194241A - Light emitting device - Google Patents
Light emitting device Download PDFInfo
- Publication number
- JP2007194241A JP2007194241A JP2006008308A JP2006008308A JP2007194241A JP 2007194241 A JP2007194241 A JP 2007194241A JP 2006008308 A JP2006008308 A JP 2006008308A JP 2006008308 A JP2006008308 A JP 2006008308A JP 2007194241 A JP2007194241 A JP 2007194241A
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- JP
- Japan
- Prior art keywords
- group
- chain
- aryl
- light emitting
- derivatives
- 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.)
- Withdrawn
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- 239000000463 material Substances 0.000 claims abstract description 92
- 150000001875 compounds Chemical class 0.000 claims description 26
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- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000002019 doping agent Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 13
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 125000005013 aryl ether group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
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- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- 229920000123 polythiophene Polymers 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
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- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
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- KXMKGOPUYUWQHC-UHFFFAOYSA-N 2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C=4C=CC=C(C=4)C=4N=C5C6=NC=CC=C6C=CC5=CC=4)=CC=C3C=CC2=C1 KXMKGOPUYUWQHC-UHFFFAOYSA-N 0.000 description 2
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- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機および光信号発生器などの分野に利用可能な発光素子に関する。 The present invention is an element that can convert electrical energy into light, and can be used in fields such as display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, and optical signal generators. It relates to an element.
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機薄膜発光素子の研究が、近年活発に行われている。この発光素子は、薄型でかつ低駆動電圧下での高輝度発光と、発光材料を選ぶことによる多色発光が特徴であり、注目を集めている。 In recent years, research on organic thin-film light-emitting devices that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes has been actively conducted. This light-emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a light-emitting material.
この研究は、イーストマンコダック社のＣ．Ｗ．Ｔａｎｇらによって有機薄膜素子が高輝度に発光することが示されて以来、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に、正孔輸送性のジアミン化合物、発光層であるトリス（８−キノリノラート）アルミニウム（III）、そして陰極としてＭｇ：Ａｇ（合金）を順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ２の緑色発光が可能であった（非特許文献１参照）。 This study was conducted by Eastman Kodak's C.I. W. Since Tang et al. Have shown that organic thin film elements emit light with high brightness, many research institutions have studied. A typical structure of the organic thin-film light-emitting device presented by the Kodak research group is a hole-transporting diamine compound, a light-emitting layer of tris (8-quinolinolato) aluminum (III), and a cathode. As a result, Mg: Ag (alloy) was sequentially provided, and green light emission of 1000 cd / m 2 was possible with a driving voltage of about 10 V (see Non-Patent Document 1).
有機薄膜発光素子は、発光層に種々の蛍光材料を用いることにより、多様な発光色を得ることが可能であることから、ディスプレイなどへの実用化研究が盛んである。また、最近では、蛍光材料の代わりにリン光材料を利用した高効率化の検討も精力的になされており、発光効率が著しく改善されることが開示されている（非特許文献２参照）。 Since organic thin-film light-emitting elements can obtain various luminescent colors by using various fluorescent materials for the light-emitting layer, practical application research to displays and the like is active. In addition, recently, studies have been vigorously made to improve efficiency by using a phosphorescent material instead of a fluorescent material, and it has been disclosed that luminous efficiency is remarkably improved (see Non-Patent Document 2).
有機薄膜発光素子における課題として、素子の駆動電圧を下げ、かつ耐久性を高めることがある。例えば、リン光材料を利用した発光素子では、発光効率は高いものの、駆動電圧は高く、耐久性も不十分なものが多い。特に青色発光素子に関しては、発光材料が蛍光材料かリン光材料かに関わらず、低駆動電圧であり、かつ耐久性が優れた信頼性の高い素子を提供する青色発光材料は少ない。例えば青色ホスト材料として、スチリル誘導体（特許文献１参照）やアントラセン誘導体（特許文献２参照）を用いる技術が開示されている。また、カルバゾール誘導体を発光材料に用いた発光素子が報告されているが、いずれも低駆動電圧と耐久性の両立が不十分であった（特許文献３〜５参照）。
上述のように、従来の有機薄膜発光素子では、駆動電圧が低く、かつ耐久性に優れた発光素子が提供されていなかった。そこで本発明は、従来技術の問題を解決し、駆動電圧が低く、かつ耐久性に優れた発光素子を提供することを目的とする。 As described above, a conventional organic thin film light emitting device has not been provided with a light emitting device having a low driving voltage and excellent durability. Accordingly, an object of the present invention is to solve the problems of the prior art, and to provide a light-emitting element having a low driving voltage and excellent durability.
本発明は、陽極と陰極の間に少なくとも発光層が存在し、電気エネルギーにより発光する素子であって、発光層がホスト材料とドーパント材料を有し、ホスト材料が一般式（１）で表されるカルバゾール骨格を有する化合物からなり、ドーパント材料が蛍光材料であることを特徴とする発光素子である。 The present invention is an element in which at least a light emitting layer exists between an anode and a cathode and emits light by electric energy, the light emitting layer has a host material and a dopant material, and the host material is represented by the general formula (1). A light-emitting element characterized in that the dopant material is a fluorescent material.
Ｒ１〜Ｒ８はそれぞれ、水素、アルキル基、シクロアルキル基、アラルキル基、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、複素環基、エステル基、カルバモイル基、アミノ基、シリル基、シロキサニル基、あるいは隣接する置換基との間の環構造の中から選ばれる。但し、Ｒ１〜Ｒ４の少なくとも１つは連結基Ｙであり、Ｙは単結合、アルキル鎖、アルキレン鎖、シクロアルキル鎖、アリール鎖、アミノ鎖、複素環鎖、シリル鎖、エーテル鎖、あるいはチオエーテル鎖のいずれかより単独または組み合わせたものより選ばれる。Ｒ９は水素、アルキル基、アリール基から選ばれる。ｎは２以上の自然数である。 R 1 to R 8 are each hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group , An ester group, a carbamoyl group, an amino group, a silyl group, a siloxanyl group, or a ring structure between adjacent substituents. However, at least one of R 1 to R 4 is a linking group Y, and Y is a single bond, an alkyl chain, an alkylene chain, a cycloalkyl chain, an aryl chain, an amino chain, a heterocyclic chain, a silyl chain, an ether chain, or It is selected from those singly or in combination from any of the thioether chains. R 9 is selected from hydrogen, an alkyl group, and an aryl group. n is a natural number of 2 or more.
本発明は、低い駆動電圧と優れた耐久性を有する発光素子が得られる。 According to the present invention, a light emitting element having a low driving voltage and excellent durability can be obtained.
本発明で用いられる陽極は、正孔を有機層に効率よく注入できる材料であれば特に限定されないが、比較的仕事関数の大きい材料を用いるのが好ましく、例えば、酸化錫、酸化インジウム、酸化亜鉛インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロールおよびポリアニリンなどの導電性ポリマーなどが挙げられる。これらの電極材料は、単独で用いてもよいが、複数の材料を積層または混合して用いてもよい。 The anode used in the present invention is not particularly limited as long as it can efficiently inject holes into the organic layer. However, it is preferable to use a material having a relatively large work function, for example, tin oxide, indium oxide, zinc oxide. Conductive metal oxides such as indium and indium tin oxide (ITO), metals such as gold, silver and chromium, inorganic conductive materials such as copper iodide and copper sulfide, conductive polymers such as polythiophene, polypyrrole and polyaniline, etc. Is mentioned. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
陽極の抵抗は、発光素子の発光に十分な電流が供給できればよく、発光素子の消費電力の点からは低抵抗であることが望ましい。例えば、３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、１００Ω／□以下の低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。 The resistance of the anode is not limited as long as a current sufficient for light emission of the light emitting element can be supplied, and is preferably low from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less will function as a device electrode, but since it is now possible to supply a substrate of about 10Ω / □, use a low-resistance product of 100Ω / □ or less. Is particularly desirable. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.
また、発光素子の機械的強度を保つために、発光素子を基板上に形成することが好ましい。基板は、ソーダガラスや無アルカリガラスなどのガラス基板が好適に用いられる。ガラス基板の厚みは、機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ２などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することもできる。さらに、陽極が安定に機能するのであれば、基板はガラスである必要はなく、例えば、プラスチック基板上に陽極を形成しても良い。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法および化学反応法など特に制限を受けるものではない。 In order to maintain the mechanical strength of the light emitting element, the light emitting element is preferably formed over a substrate. As the substrate, a glass substrate such as soda glass or non-alkali glass is preferably used. As the thickness of the glass substrate, it is sufficient that the thickness is sufficient to maintain the mechanical strength. The glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but soda lime glass with a barrier coat such as SiO 2 is also available on the market. it can. Furthermore, if the anode functions stably, the substrate does not have to be glass. For example, the anode may be formed on a plastic substrate. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.
本発明で用いられる陰極に用いられる材料は、電子を有機層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、セシウム、カルシウムおよびマグネシウムならびにこれらの合金などが挙げられる。電子注入効率をあげて素子特性を向上させるためには、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかしながら、これらの低仕事関数金属は、一般に大気中で不安定であることが多いため、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を得る方法が好ましい例として挙げることができる。また、フッ化リチウムのような無機塩の使用も可能である。更に、電極保護のために白金、金、銀、銅、鉄、錫、アルミニウムおよびインジウムなどの金属、またはこれら金属を用いた合金、シリカ、チタニアおよび窒化ケイ素などの無機物、ポリビニルアルコール、ポリ塩化ビニル、炭化水素系高分子化合物などの有機高分子化合物を積層することが、好ましい例として挙げられる。これらの電極の作製法は、抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティングおよびコーティングなど、導通を取ることができれば特に制限されない。 The material used for the cathode used in the present invention is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but is generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium. Lithium, sodium, potassium, cesium, calcium and magnesium, and alloys thereof. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, since these low work function metals are generally unstable in the atmosphere, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less on a vacuum deposition film thickness meter) and stable. A preferred example is a method for obtaining a high electrode. Also, an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, polyvinyl chloride Lamination of organic polymer compounds such as hydrocarbon polymer compounds is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.
本発明の発光素子は、少なくとも発光層が存在し、発光層がホスト材料とドーパント材料を有し、ホスト材料として一般式（１）で表されるカルバゾール骨格を有する化合物を含む。 The light-emitting element of the present invention includes at least a light-emitting layer, the light-emitting layer includes a host material and a dopant material, and includes a compound having a carbazole skeleton represented by the general formula (1) as the host material.
Ｒ１〜Ｒ８はそれぞれ、水素、アルキル基、シクロアルキル基、アラルキル基、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、複素環基、エステル基、カルバモイル基、アミノ基、シリル基、シロキサニル基、あるいは隣接する置換基との間の環構造の中から選ばれる。但し、Ｒ１〜Ｒ４の少なくとも１つは連結基Ｙであり、Ｙは単結合、アルキル鎖、アルキレン鎖、シクロアルキル鎖、アリール鎖、アミノ鎖、複素環鎖、シリル鎖、エーテル鎖、あるいはチオエーテル鎖のいずれかより単独または組み合わせたものより選ばれる。Ｒ９は水素、アルキル基、アリール基から選ばれる。ｎは２以上の自然数である。 R 1 to R 8 are each hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group , An ester group, a carbamoyl group, an amino group, a silyl group, a siloxanyl group, or a ring structure between adjacent substituents. However, at least one of R 1 to R 4 is a linking group Y, and Y is a single bond, an alkyl chain, an alkylene chain, a cycloalkyl chain, an aryl chain, an amino chain, a heterocyclic chain, a silyl chain, an ether chain, or It is selected from those singly or in combination from any of the thioether chains. R 9 is selected from hydrogen, an alkyl group, and an aryl group. n is a natural number of 2 or more.
本発明に用いるカルバゾール骨格を有する化合物の本旨とするところは、カルバゾール骨格を分子中に複数個有する点である。さらに、複数のカルバゾール骨格がＲ１〜Ｒ４の少なくとも一箇所に存在する連結基を介して連結されることにより、正孔輸送能を発現しやすい電子構造となり、陽極側からの正孔注入・輸送が円滑に行われ、低駆動電圧化が可能となる。正孔輸送能を示す一つの指標としてイオン化ポテンシャルがあるが、本発明のカルバゾール骨格を有する化合物のイオン化ポテンシャルは、好ましくは６．０ｅＶ以下である。なお、イオン化ポテンシャルの絶対値は測定方法により異なる場合があるが、本発明のイオン化ポテンシャルは、大気雰囲気型紫外線光電子分析装置（ＡＣ−１、理研機器（株）製）を用いて、ＩＴＯガラス基板上に３０ｎｍ〜１００ｎｍの厚さに蒸着した薄膜を測定した値である。 The main point of the compound having a carbazole skeleton used in the present invention is that it has a plurality of carbazole skeletons in the molecule. Furthermore, by connecting a plurality of carbazole skeletons via a linking group present in at least one of R 1 to R 4, an electronic structure that easily develops a hole transport capability is obtained, and hole injection from the anode side Transportation is carried out smoothly, and a low drive voltage can be achieved. An ionization potential is one index showing the hole transporting ability, and the ionization potential of the compound having a carbazole skeleton of the present invention is preferably 6.0 eV or less. Although the absolute value of the ionization potential may vary depending on the measurement method, the ionization potential of the present invention is an ITO glass substrate using an atmospheric-type ultraviolet photoelectron analyzer (AC-1, manufactured by Riken Kikai Co., Ltd.). It is the value which measured the thin film vapor-deposited on the thickness of 30 nm-100 nm on the top.
置換基Ｒ１〜Ｒ８は本発明の効果に照らしてカルバゾール骨格上の水素とそれに等価の特性を有する置換基を列挙したものである。すなわち、例えば水素、アルキル基、シクロアルキル基、アラルキル基、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、複素環基、エステル基、カルバモイル基、アミノ基、シリル基、シロキサニル基、あるいは隣接する置換基との間の環構造が挙げられる。 In view of the effects of the present invention, the substituents R 1 to R 8 are a list of hydrogen on the carbazole skeleton and substituents having properties equivalent thereto. That is, for example, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group, ester group, carbamoyl And a ring structure between a group, an amino group, a silyl group, a siloxanyl group, or an adjacent substituent.
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、これは無置換でも置換されていてもかまわない。また、シクロアルキル基とは例えばシクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アラルキル基とは例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、脂肪族炭化水素と芳香族炭化水素はいずれも無置換でも置換されていてもかまわない。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。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、シクロヘキセン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、これは無置換でも置換されていてもかまわない。また、アルキニル基とは例えばアセチレ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。 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, which may be unsubstituted or substituted. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. The aralkyl group is an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. It doesn't matter. The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. . The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted.
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。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。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。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。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し、これは無置換でも置換されていてもかまわない。また、複素環基とは例えばフリル基、チエニル基、オキサゾリル基、ピリジル基、キノリル基、カルバゾリル基などの炭素以外の原子を有する環状構造基を示し、これは無置換でも置換されていてもかまわない。ハロゲンとはフッ素、塩素、臭素、ヨウ素を示す。 The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. 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. The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. 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. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group, which may be unsubstituted or substituted. The heterocyclic group is a cyclic structural group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, or a carbazolyl group, which may be unsubstituted or substituted. Absent. Halogen is fluorine, chlorine, bromine or iodine.
エステル基、カルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環などで置換されたものも含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環は無置換でも置換されていてもかまわない。シリル基とは例えばトリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。シロキサニル基とは例えばトリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。また、隣接置換基との間に環構造を形成しても構わない。形成される環構造は無置換でも置換されていてもかまわない。 Ester groups, carbamoyl groups, and amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, etc., and aliphatic hydrocarbons, alicyclic hydrocarbons, aromatics The group hydrocarbon and heterocycle may be unsubstituted or substituted. A silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. A ring structure may be formed between adjacent substituents. The ring structure formed may be unsubstituted or substituted.
複数のカルバゾール骨格を連結する連結基Ｙとしては、同じくカルバゾール骨格が有する正孔輸送能を阻害しないものが好ましく、単結合、アルキル鎖、アルキレン鎖、シクロアルキル鎖、アリール鎖、アミノ鎖、複素環鎖、シリル鎖、エーテル鎖、あるいはチオエーテル鎖のいずれかより単独または組み合わせたものより選ばれる。これらの連結基についての説明は上述と同様である。 As the linking group Y for linking a plurality of carbazole skeletons, those which do not inhibit the hole transport ability of the carbazole skeleton are preferable, and single bonds, alkyl chains, alkylene chains, cycloalkyl chains, aryl chains, amino chains, heterocyclic rings A chain, a silyl chain, an ether chain, or a thioether chain is used alone or in combination. The explanation for these linking groups is the same as described above.
上述した置換基Ｒ１〜Ｒ８および連結基Ｙの中でも、熱的・化学的安定性が高いことから、置換基Ｒ１〜Ｒ８としては、水素、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基、隣接する置換基との間の環構造が、また連結基Ｙとしては、単結合、アルキレン鎖、アリール鎖、アミノ鎖、あるいは複素環鎖のいずれかより単独または組み合わせたものより選ばれるのが好ましい。連結基Ｙについては、分子が剛直となり耐熱性が一層優れることから単結合のものが特に好ましい。 Among the substituents R 1 to R 8 and the linking group Y described above, since the thermal and chemical stability is high, the substituents R 1 to R 8 include hydrogen, an alkyl group, an alkoxy group, an aryl group, a complex A ring group, an amino group, a ring structure between adjacent substituents, and the linking group Y is a single bond, an alkylene chain, an aryl chain, an amino chain, or a heterocyclic chain, alone or in combination It is preferable to be selected. The linking group Y is particularly preferably a single bond since the molecule is rigid and the heat resistance is further improved.
更に、合成、精製の容易さから、本発明においては、特に、一般式（２）で表されるカルバゾール骨格を有する化合物が好適に用いられる。 Further, in the present invention, a compound having a carbazole skeleton represented by the general formula (2) is preferably used because of ease of synthesis and purification.
Ｒ１０〜Ｒ２３はそれぞれ、水素、アルキル基、シクロアルキル基、アラルキル基、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、複素環基、エステル基、カルバモイル基、アミノ基、シリル基、シロキサニル基、あるいは隣接する置換基との間の環構造の中から選ばれる。Ｒ２４およびＲ２５はそれぞれ、水素、アルキル基、アリール基より選ばれる。 R 10 to R 23 are each hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group , An ester group, a carbamoyl group, an amino group, a silyl group, a siloxanyl group, or a ring structure between adjacent substituents. R 24 and R 25 are each selected from hydrogen, an alkyl group, and an aryl group.
上記カルバゾール骨格を有する化合物として、具体的には下記のような構造が挙げられる。 Specific examples of the compound having the carbazole skeleton include the following structures.
発光材料のホスト材料はカルバゾール骨格を有する化合物一種のみ、もしくは、複数のカルバゾール骨格を有する化合物を混合して用いてもよく、さらには、カルバゾール骨格を有する化合物と既知のホスト材料の一種類以上と混合して用いてもよい。 As the host material of the light emitting material, only one kind of compound having a carbazole skeleton or a mixture of compounds having a plurality of carbazole skeletons may be used. Further, a compound having a carbazole skeleton and one or more kinds of known host materials may be used. You may mix and use.
ホスト材料としては特に限定されるものではないが、以前から発光体として知られていたアントラセン、フェナンスレン、ピレン、ペリレン、クリセンなどの縮合環誘導体、トリス（８−キノリノラート）アルミニウムを始めとするキノリノール誘導体の金属錯体、ベンズオキサゾール誘導体、スチルベン誘導体、ベンズチアゾール誘導体、チアジアゾール誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、ビススチリルアントラセン誘導体やジスチリルベンゼン誘導体などのビススチリル誘導体、ビス（Ｎ−カルバゾリル）ビフェニルなどのカルバゾール誘導体、トリアゾール誘導体、フェナントロリン誘導体、トリフェニルアミン誘導体、キノリノール誘導体と異なる配位子を組み合わせた金属錯体、オキサジアゾール誘導体金属錯体、ベンズアゾール誘導体金属錯体、クマリン誘導体、ピロロピリジン誘導体、ペリノン誘導体、チアジアゾロピリジン誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、そして、ポリチオフェン誘導体などが使用できる。 The host material is not particularly limited, but condensed ring derivatives such as anthracene, phenanthrene, pyrene, perylene, chrysene, etc., and quinolinol derivatives such as tris (8-quinolinolato) aluminum, which have been known as light emitters for a long time. Metal complexes, benzoxazole derivatives, stilbene derivatives, benzthiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, oxadiazole derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, bis Different from carbazole derivatives such as (N-carbazolyl) biphenyl, triazole derivatives, phenanthroline derivatives, triphenylamine derivatives, quinolinol derivatives Metal complexes combining ligands, oxadiazole derivative metal complexes, benzazole derivative metal complexes, coumarin derivatives, pyrrolopyridine derivatives, perinone derivatives, thiadiazolopyridine derivatives, in polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, and Polythiophene derivatives and the like can be used.
本発明の発光層には、さらにドーパント材料として蛍光材料が含まれる。蛍光材料としては、特に限定されないが、ナフタレン、アントラセン、フェナンスレン、ピレン、トリフェニレン、ペリレン、フルオレン、インデンなどのアリール環を有する化合物やその誘導体（例えば２−（ベンゾチアゾール−２−イル）−９，１０−ジフェニルアントラセンや５，６，１１，１２−テトラフェニルナフタセンなど）、フラン、ピロール、チオフェン、シロール、９−シラフルオレン、９，９’−スピロビシラフルオレン、ベンゾチオフェン、ベンゾフラン、インドール、ジベンゾチオフェン、ジベンゾフラン、イミダゾピリジン、フェナントロリン、ピラジン、ナフチリジン、キノキサリン、ピロロピリジン、チオキサンテンなどのヘテロアリール環を有する化合物やその誘導体、ジスチリルベンゼン誘導体、４，４’−ビス（２−（４−ジフェニルアミノフェニル）エテニル）ビフェニル、４，４’−ビス（Ｎ−（スチルベン−４−イル）−Ｎ−フェニルアミノ）スチルベンなどのアミノスチリル誘導体、芳香族アセチレン誘導体、テトラフェニルブタジエン誘導体、スチルベン誘導体、アルダジン誘導体、ピロメテン誘導体、ジケトピロロ［３，４−ｃ］ピロール誘導体、２，３，５，６−１Ｈ，４Ｈ−テトラヒドロ−９−（２’−ベンゾチアゾリル）キノリジノ［９，９ａ，１−ｇｈ］クマリンなどのクマリン誘導体、イミダゾール、チアゾール、チアジアゾール、カルバゾール、オキサゾール、オキサジアゾール、トリアゾールなどのアゾール誘導体およびその金属錯体およびＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミンに代表される芳香族アミン誘導体などが挙げられる。 The light emitting layer of the present invention further contains a fluorescent material as a dopant material. The fluorescent material is not particularly limited, but is a compound having an aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene or a derivative thereof (for example, 2- (benzothiazol-2-yl) -9, 10-diphenylanthracene, 5,6,11,12-tetraphenylnaphthacene, etc.), furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9′-spirobisilafluorene, benzothiophene, benzofuran, indole, Compounds having heteroaryl rings such as dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene and their derivatives, distyrylbenzene derivatives, 4,4 Aminostyryl derivatives such as -bis (2- (4-diphenylaminophenyl) ethenyl) biphenyl, 4,4'-bis (N- (stilben-4-yl) -N-phenylamino) stilbene, aromatic acetylene derivatives, Tetraphenylbutadiene derivative, stilbene derivative, aldazine derivative, pyromethene derivative, diketopyrrolo [3,4-c] pyrrole derivative, 2,3,5,6-1H, 4H-tetrahydro-9- (2′-benzothiazolyl) quinolidino [9 , 9a, 1-gh] coumarin derivatives such as coumarin, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and metal complexes thereof, and N, N′-diphenyl-N, N′-di (3-Methylphenyl) -4,4 - an aromatic amine derivative typified by diphenyl 1,1'-diamine.
本発明において、発光層は単一層、複数層のどちらでもよく、いずれもホスト材料およびドーパント材料を主成分とする発光材料により形成される。発光材料はホスト材料とドーパント材料との混合物であっても、ホスト材料単独であっても、いずれでもよい。すなわち、本発明の発光素子では、各発光層において、ホスト材料もしくはドーパント材料のみが発光してもよいし、ホスト材料とドーパント材料がともに発光してもよい。ホスト材料とドーパント材料は、それぞれ一種類であっても、複数の組み合わせであっても、いずれでもよい。ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれでもよい。ドーパント材料は積層されていても、分散されていても、いずれでもよい。ドーパント材料の量は、多すぎると濃度消光現象が起きるため、ホスト材料に対して２０重量％以下で用いることが好ましく、さらに好ましくは１０重量％以下である。ドーピング方法は、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。 In the present invention, the light emitting layer may be either a single layer or a plurality of layers, both of which are formed of a light emitting material mainly composed of a host material and a dopant material. The light emitting material may be a mixture of a host material and a dopant material, or may be a host material alone. That is, in the light emitting element of the present invention, only the host material or the dopant material may emit light in each light emitting layer, or both the host material and the dopant material may emit light. Each of the host material and the dopant material may be one kind or a plurality of combinations. The dopant material may be included in the entire host material or may be partially included. The dopant material may be laminated or dispersed. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that it is preferably used at 20% by weight or less, more preferably 10% by weight or less with respect to the host material. The doping method can be formed by a co-evaporation method with a host material, but may be pre-mixed with the host material and then simultaneously deposited.
本発明の発光素子を構成する層は、発光層のみからなる構成の他に、１）正孔輸送層／発光層／電子輸送層および、２）発光層／電子輸送層、３）正孔輸送層／発光層などの積層構造を有しても良い。また、上記各層は、それぞれ単一層、複数層のいずれでもよい。正孔輸送層および電子輸送層が複数層を有する場合、電極に接する側の層をそれぞれ正孔注入層および電子注入層と呼ぶことがあるが、以下の説明では正孔注入材料は正孔輸送材料に、電子注入材料は電子輸送材料にそれぞれ含まれる。 The layer constituting the light emitting device of the present invention is composed of only the light emitting layer, 1) hole transport layer / light emitting layer / electron transport layer, 2) light emitting layer / electron transport layer, and 3) hole transport. It may have a laminated structure such as a layer / light emitting layer. Each of the layers may be a single layer or a plurality of layers. When the hole transport layer and the electron transport layer have a plurality of layers, the layers in contact with the electrodes may be referred to as a hole injection layer and an electron injection layer, respectively. In the material, the electron injection material is included in the electron transport material.
正孔輸送層は、正孔輸送材料の一種または二種以上を積層または混合する方法、もしくは、正孔輸送材料と高分子結着剤の混合物を用いる方法により形成される。また、正孔輸送材料に塩化鉄（III）のような無機塩を添加して正孔輸送層を形成してもよい。正孔輸送材料は、発光素子の作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されない。例えば、４，４’−ビス（Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ）ビフェニル、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニル、４，４’，４”−トリス（３−メチルフェニル（フェニル）アミノ）トリフェニルアミンなどのトリフェニルアミン誘導体、カルバゾール誘導体、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、ベンゾフラン誘導体やチオフェン誘導体、オキサジアゾール誘導体、フタロシアニン誘導体、ポルフィリン誘導体などの複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリチオフェン、ポリアニリン、ポリフルオレン、ポリビニルカルバゾールおよびポリシランなどが好ましい。 The hole transport layer is formed by a method of laminating or mixing one or more hole transport materials or a method using a mixture of a hole transport material and a polymer binder. Alternatively, the hole transport layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole transport material. The hole transport material is not particularly limited as long as it is a compound that forms a thin film necessary for manufacturing a light emitting element, can inject holes from the anode, and can further transport holes. For example, 4,4′-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl, 4,4 Triphenylamine derivatives such as', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine, carbazole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives In the polymer system, polycarbonates and styrene derivatives, polythiophene, polyaniline, polyfluorene, polyvinyl carbazole, polysilane, and the like having the above monomer in the side chain are preferable.
本発明の発光層に含まれるカルバゾール骨格を有する化合物も正孔輸送能を有することから、正孔輸送材料として用いてもよい。 Since the compound having a carbazole skeleton contained in the light emitting layer of the present invention also has a hole transport ability, it may be used as a hole transport material.
本発明において、電子輸送層とは、陰極から電子が注入され、さらに電子を輸送する層である。電子輸送層には、電子注入効率が高く、注入された電子を効率良く輸送することが望まれる。そのため電子輸送層は、電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質で構成されることが望ましい。しかしながら、正孔と電子の輸送バランスを考えた場合に、電子輸送層が陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たすならば、電子輸送能力がそれ程高くない材料で構成されていても、発光効率を向上させる効果は電子輸送能力が高い材料で構成されている場合と同等となる。したがって、本発明における電子輸送層には、正孔の移動を効率よく阻止できる正孔阻止層も同義のものとして含まれる。 In the present invention, the electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons. The electron transport layer has high electron injection efficiency, and it is desired to efficiently transport injected electrons. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity, a high electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use. However, considering the transport balance between holes and electrons, if the electron transport layer mainly plays a role of effectively preventing the holes from the anode from recombining and flowing to the cathode side, the electron transport Even if it is made of a material that does not have a high capability, the effect of improving the luminous efficiency is equivalent to that of a material that has a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
電子輸送層に用いられる電子輸送材料は、特に限定されないが、ナフタレン、アントラセンなどの縮合アリール環を有する化合物やその誘導体、４，４’−ビス（ジフェニルエテニル）ビフェニルに代表されるスチリル系芳香環誘導体、ペリレン誘導体、ペリノン誘導体、クマリン誘導体、ナフタルイミド誘導体、アントラキノンやジフェノキノンなどのキノン誘導体、リンオキサイド誘導体、カルバゾール誘導体およびインドール誘導体、トリス（８−キノリノラート）アルミニウム（III）などのキノリノール錯体やヒドロキシフェニルオキサゾール錯体などのヒドロキシアゾール錯体、アゾメチン錯体、トロポロン金属錯体およびフラボノール金属錯体、電子受容性窒素を有するヘテロアリール環を有する化合物などが挙げられる。 The electron transport material used for the electron transport layer is not particularly limited, but is a compound having a condensed aryl ring such as naphthalene or anthracene or a derivative thereof, or a styryl-based fragrance represented by 4,4′-bis (diphenylethenyl) biphenyl. Ring derivatives, perylene derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III) and hydroxy Examples thereof include hydroxyazole complexes such as phenyloxazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes, and compounds having a heteroaryl ring having electron-accepting nitrogen.
本発明における電子受容性窒素とは、隣接原子との間に多重結合を形成している窒素原子を表す。窒素原子が高い電子陰性度を有することから、該多重結合は電子受容的な性質を有する。それゆえ、電子受容性窒素を含むヘテロアリール環は、高い電子親和性を有する。電子受容性窒素を含むヘテロアリール環は、例えば、ピリジン環、ピラジン環、ピリミジン環、キノリン環、キノキサリン環、ナフチリジン環、ピリミドピリミジン環、ベンゾキノリン環、フェナントロリン環、イミダゾール環、オキサゾール環、オキサジアゾール環、トリアゾール環、チアゾール環、チアジアゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、ベンズイミダゾール環、フェナンスロイミダゾール環などが挙げられる。 The electron-accepting nitrogen in the present invention represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron accepting property. Therefore, heteroaryl rings containing electron-accepting nitrogen have a high electron affinity. Heteroaryl rings containing electron-accepting nitrogen include, for example, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxalate ring, Examples include a diazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.
また、本発明の電子受容性窒素を含むヘテロアリール環構造を有する化合物は、炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成されることが好ましい。これらの元素で構成された電子受容性窒素を含むヘテロアリール環構造を有する化合物は、高い電子輸送能を有し、駆動電圧を著しく低減できる。 The compound having a heteroaryl ring structure containing electron-accepting nitrogen of the present invention is preferably composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon and phosphorus. A compound having a heteroaryl ring structure containing electron-accepting nitrogen composed of these elements has a high electron transporting ability and can significantly reduce a driving voltage.
電子受容性窒素を含み、炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成されるヘテロアリール環構造を有する化合物としては、例えば、ベンズイミダゾール誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラジン誘導体、フェナントロリン誘導体、キノキサリン誘導体、キノリン誘導体、ベンゾキノリン誘導体、ビピリジンやターピリジンなどのオリゴピリジン誘導体、キノキサリン誘導体およびナフチリジン誘導体などが好ましい化合物として挙げられる。中でも、トリス（Ｎ−フェニルベンズイミダゾール−２−イル）ベンゼンなどのイミダゾール誘導体、１，３−ビス［（４−ｔｅｒｔ−ブチルフェニル）１，３，４−オキサジアゾリル］フェニレンなどのオキサジアゾール誘導体、Ｎ−ナフチル−２，５−ジフェニル−１，３，４−トリアゾールなどのトリアゾール誘導体、バソクプロインや１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンなどのフェナントロリン誘導体、２，２’−ビス（ベンゾ［ｈ］キノリン−２−イル）−９，９’−スピロビフルオレンなどのベンゾキノリン誘導体、２，５−ビス（６’−（２’，２”−ビピリジル））−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン誘導体、１，３−ビス（４’−（２，２’：６’２”−ターピリジニル））ベンゼンなどのターピリジン誘導体、ビス（１−ナフチル）−４−（１，８−ナフチリジン−２−イル）フェニルホスフィンオキサイドなどのナフチリジン誘導体が、電子輸送能の点から好ましく用いられる。さらに、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼン、２，７−ビス（１，１０−フェナントロリン−９−イル）ナフタレン、１，３−ビス（２−フェニル−１，１０−フェナントロリン−９−イル）ベンゼンなどのフェナントロリン二量体、および２，５−ビス（６’−（２’，２”−ビピリジル））−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン二量体は、本発明の一般式（１）で表されるピレン化合物と組み合わせた際の耐久性向上効果が著しく高く、特に好ましい例として挙げられる。 Examples of compounds having a heteroaryl ring structure containing an electron-accepting nitrogen and composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus include benzimidazole derivatives, benzoxazole derivatives, and benzthiazoles. Preferred examples include derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives, and naphthyridine derivatives. . Among them, imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene, oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene, Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 ′ A benzoquinoline derivative such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1, Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, 1,3-bis (4 ′-(2,2 ′: 6′2 ″ -ta Terpyridine derivatives such as pyridinyl)) benzene, naphthyridine derivatives such as bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferably used from the viewpoint of electron transporting capability. Furthermore, 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,7-bis (1,10-phenanthroline-9-yl) naphthalene, 1,3-bis (2-phenyl-1, Phenanthroline dimers such as 10-phenanthroline-9-yl) benzene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, etc. This bipyridine dimer has a significantly high durability improving effect when combined with the pyrene compound represented by the general formula (1) of the present invention, and is particularly preferable.
上記電子輸送材料は単独でも用いられるが、上記電子輸送材料の２種以上を混合して用いたり、その他の電子輸送材料の一種以上を上記の電子輸送材料に混合して用いても構わない。また、アルカリ金属やアルカリ土類金属などの金属と混合して用いることも可能である。電子輸送層のイオン化ポテンシャルは、特に限定されないが、好ましくは５．８ｅＶ以上８．０ｅＶ以下であり、より好ましくは６．０ｅＶ以上７．５ｅＶ以下である。 The electron transport material may be used alone, but two or more of the electron transport materials may be mixed and used, or one or more of the other electron transport materials may be mixed with the electron transport material. It is also possible to use a mixture with a metal such as an alkali metal or an alkaline earth metal. The ionization potential of the electron transport layer is not particularly limited, but is preferably 5.8 eV or more and 8.0 eV or less, and more preferably 6.0 eV or more and 7.5 eV or less.
発光素子を構成する上記各層の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されないが、通常は、素子特性の点から抵抗加熱蒸着または電子ビーム蒸着が好ましい。 The method of forming each layer constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, etc., but resistance heating vapor deposition or electron beam vapor deposition is usually used in terms of element characteristics. preferable.
層の厚みは、発光物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。発光層、電子輸送層、正孔輸送層の膜厚はそれぞれ、好ましくは１ｎｍ以上２００ｎｍ以下であり、さらに好ましくは５ｎｍ以上１００ｎｍ以下である。 The thickness of the layer depends on the resistance value of the luminescent material and cannot be limited, but is selected from 1 to 1000 nm. The film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.
本発明の発光素子は、電気エネルギーを光に変換できる機能を有する。ここで電気エネルギーとしては主に直流電流が使用されるが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力や寿命を考慮すると、できるだけ低いエネルギーで最大の輝度が得られるよう選ばれるべきである。 The light-emitting element of the present invention has a function of converting electrical energy into light. Here, a direct current is mainly used as the electric energy, but a pulse current or an alternating current can also be used. The current value and voltage value are not particularly limited, but should be selected so that the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the device.
本発明の発光素子は、例えば、マトリクスおよび／またはセグメント方式で表示するディスプレイとして好適に用いられる。 The light emitting device of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.
マトリクス方式とは、表示のための画素が格子状やモザイク状など二次元的に配置され、画素の集合で文字や画像を表示する。画素の形状やサイズは用途によって決まる。例えば、パソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられ、また、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法は、線順次駆動方法やアクティブマトリクスのどちらでもよい。線順次駆動はその構造が簡単であるが、動作特性を考慮した場合、アクティブマトリクスの方が優れる場合があるので、これも用途によって使い分けることが必要である。 In the matrix method, pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and a character or an image is displayed by a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. Although the structure of the line sequential drive is simple, the active matrix may be superior in consideration of the operation characteristics, and it is necessary to use it depending on the application.
本発明におけるセグメント方式とは、予め決められた情報を表示するようにパターンを形成し、このパターンの配置によって決められた領域を発光させる方式である。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示および自動車のパネル表示などが挙げられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。 The segment system in the present invention is a system in which a pattern is formed so as to display predetermined information and an area determined by the arrangement of the pattern is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.
本発明の発光素子は、各種機器等のバックライトとしても好ましく用いられる。バックライトは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ装置、自動車パネル、表示板および標識などに使用される。特に、液晶表示装置、中でも薄型化が検討されているパソコン用途のバックライトに本発明の発光素子は好ましく用いられ、従来のものより薄型で軽量なバックライトを提供できる。 The light emitting device of the present invention is also preferably used as a backlight for various devices. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, the light-emitting element of the present invention is preferably used for a backlight for a liquid crystal display device, particularly a personal computer for which a reduction in thickness is being considered, and a backlight that is thinner and lighter than conventional ones can be provided.
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ない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited by these Examples.
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断し、ＩＴＯ導電膜をフォトリソグラフィ法によりパターン加工して、発光部分および電極引き出し部分を作製した。得られた基板をアセトン、“セミコクリン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。続いて、イソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。素子を作製する直前にこの基板を１時間ＵＶ−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が５×１０−５Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを１０ｎｍ、正孔輸送材料として、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルを５０ｎｍ蒸着した。次に、発光材料として、ホスト材料として、化合物[３]を、またドーパント材料として４，４‘−ビス［４−（ジ−ｐ−トリルアミノ）スチリル］ビフェニルをドープ濃度が５ｗｔ％になるように３５ｎｍの厚さに蒸着した。次に、電子輸送材料として、トリス（８−キノリノラート）アルミニウム（Ａｌｑ３）を２０ｎｍの厚さに積層した。以上で形成した有機層上に、リチウムを０．５ｎｍの厚さに蒸着した後、アルミニウムを１０００ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。この発光素子を直流駆動したところ青色発光が得られ、３００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は８．１Ｖであり、輝度半減時間は１８００時間であった。
Example 1
A glass substrate (15 Ω / □, manufactured by Asahi Glass Co., Ltd., electron beam evaporation product) on which an ITO transparent conductive film is deposited to 150 nm is cut to 30 × 40 mm, and the ITO conductive film is patterned by a photolithography method to produce a light emitting portion. And the electrode extraction part was produced. The obtained substrate was ultrasonically cleaned with acetone, “Semicocrine 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes and dried. Immediately before the device was fabricated, this substrate was subjected to UV-ozone treatment for 1 hour, further placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −5 Pa or less. By the resistance heating method, first, copper phthalocyanine was deposited as a hole injecting material at 10 nm, and 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited as a hole transporting material at 50 nm. Next, the compound [3] is used as the light emitting material, the host material, and 4,4′-bis [4- (di-p-tolylamino) styryl] biphenyl as the dopant material so that the doping concentration is 5 wt%. Vapor deposited to a thickness of 35 nm. Next, tris (8-quinolinolato) aluminum (Alq3) was laminated to a thickness of 20 nm as an electron transport material. On the organic layer formed as described above, lithium was vapor-deposited to a thickness of 0.5 nm, and then aluminum was vapor-deposited to a thickness of 1000 nm to form a 5 × 5 mm square device. The film thickness referred to here is a display value of a crystal oscillation type film thickness monitor. When this light-emitting element was driven by direct current, blue light emission was obtained, and the driving voltage for obtaining a light emission luminance of 300 cd / m 2 was 8.1 V, and the luminance half time was 1800 hours.
実施例２
ホスト材料として化合物［９］を用いた以外は、実施例１と同様にして発光素子を作製した。この発光素子を直流駆動したところ青色発光が得られ、３００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は８．４Ｖであり、輝度半減時間は２０００時間であった。
Example 2
A light emitting device was produced in the same manner as in Example 1 except that the compound [9] was used as the host material. When this light emitting element was driven by direct current, blue light emission was obtained, and the driving voltage for obtaining the light emission luminance of 300 cd / m 2 was 8.4 V, and the luminance half time was 2000 hours.
実施例３
ホスト材料として化合物［２１］を用いた以外は、実施例１と同様にして発光素子を作製した。この発光素子を直流駆動したところ青色発光が得られ、３００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は７．９Ｖであり、輝度半減時間は２５００時間であった。
Example 3
A light emitting device was produced in the same manner as in Example 1 except that the compound [21] was used as the host material. When this light emitting element was driven by direct current, blue light emission was obtained, and the driving voltage for obtaining the light emission luminance of 300 cd / m 2 was 7.9 V, and the luminance half time was 2500 hours.
比較例１
ホスト材料として４，４’−ビス（Ｎ−カルバゾリル）ビフェニルを用いた以外は、実施例１と同様にして発光素子を作製した。この発光素子を直流駆動したところ青色発光が得られ、３００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は１０．３Ｖであり、輝度半減時間は５００時間であった。
Comparative Example 1
A light-emitting element was fabricated in the same manner as in Example 1 except that 4,4′-bis (N-carbazolyl) biphenyl was used as the host material. When this light emitting element was driven by a direct current, blue light emission was obtained, the driving voltage for obtaining the light emission luminance of 300 cd / m 2 was 10.3 V, and the luminance half time was 500 hours.
実施例４
ドーパント材料として２，５，８，１１−テトラ−ｔｅｒｔ−ブチルペリレンをドープ濃度が１ｗｔ％となるように用いた以外は、実施例３と同様にして発光素子を作製した。この発光素子を直流駆動したところ青色発光が得られ、２００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は７．９Ｖであり、輝度半減時間は２５００時間であった。
Example 4
A light emitting device was produced in the same manner as in Example 3 except that 2,5,8,11-tetra-tert-butylperylene was used as the dopant material so that the doping concentration was 1 wt%. When this light emitting element was driven by a direct current, blue light emission was obtained, the driving voltage for obtaining a light emission luminance of 200 cd / m 2 was 7.9 V, and the luminance half time was 2500 hours.
実施例５
電子輸送材料として下記式で表されるＥ−１を用いた以外は、実施例３と同様にして発光素子を作製した。この発光素子を直流駆動したところ青色発光が得られ、３００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は６．４Ｖであり、輝度半減時間は２５００時間であった。
Example 5
A light emitting device was produced in the same manner as in Example 3 except that E-1 represented by the following formula was used as the electron transport material. When this light emitting device was driven by a direct current, blue light emission was obtained, the driving voltage for obtaining a light emission luminance of 300 cd / m 2 was 6.4 V, and the luminance half time was 2500 hours.
実施例６
ドーパント材料として下記式で表されるＤ−１を用いた以外は実施例５と同様にして発光素子を作製した。この発光素子を直流駆動したところ緑色発光が得られ、５００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は６．０Ｖであり、輝度半減時間は３０００時間であった。
Example 6
A light emitting device was produced in the same manner as in Example 5 except that D-1 represented by the following formula was used as the dopant material. When this light emitting element was driven by a direct current, green light emission was obtained, the driving voltage for obtaining the light emission luminance of 500 cd / m 2 was 6.0 V, and the luminance half time was 3000 hours.
比較例２
ホスト材料として４，４’−ビス（Ｎ−カルバゾリル）ビフェニルを用いた以外は、実施例６と同様にして発光素子を作製した。この発光素子を直流駆動したところ緑色発光が得られ、５００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は７．６Ｖであり、輝度半減時間は４００時間であった。
Comparative Example 2
A light emitting device was fabricated in the same manner as in Example 6 except that 4,4′-bis (N-carbazolyl) biphenyl was used as the host material. When this light emitting device was DC-driven, green light emission was obtained, the driving voltage for obtaining the light emission luminance of 500 cd / m 2 was 7.6 V, and the luminance half time was 400 hours.
実施例７
ドーパント材料として下記式で表されるＤ−２をドープ濃度が２ｗｔ％になるように用いた以外は実施例５と同様にして発光素子を作製した。この発光素子を直流駆動したところ赤色発光が得られ、４００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は７．０Ｖであり、輝度半減時間は３３００時間であった。
Example 7
A light emitting device was produced in the same manner as in Example 5 except that D-2 represented by the following formula was used as a dopant material so that the doping concentration was 2 wt%. When this light emitting element was driven by a direct current, red light emission was obtained. The driving voltage for obtaining the light emission luminance of 400 cd / m 2 was 7.0 V, and the luminance half time was 3300 hours.
比較例３
ドーパント材料としてビス｛２−（２−ベンゾチオフェニル）ピリジル｝（アセチルアセトナート）イリジウム錯体をドープ濃度が８ｗｔ％になるように用いた以外は実施例５と同様にして発光素子を作製した。この発光素子を直流駆動したところ赤色発光が得られ、４００ｃｄ／ｍ２の発光輝度を得る際の駆動電圧は８．０Ｖであり、輝度半減時間は２０００時間であった。
Comparative Example 3
A light emitting device was fabricated in the same manner as in Example 5 except that bis {2- (2-benzothiophenyl) pyridyl} (acetylacetonato) iridium complex was used as a dopant material so that the doping concentration was 8 wt%. When this light emitting element was DC-driven, red light emission was obtained, and the driving voltage for obtaining the light emission luminance of 400 cd / m 2 was 8.0 V, and the luminance half time was 2000 hours.
実施例８
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断し、ＩＴＯ導電膜をフォトリソグラフィ法によって３００μｍピッチ（残り幅２７０μｍ）×３２本のストライプ状にパターン加工した。ＩＴＯストライプの長辺方向片側は外部との電気的接続を容易にするために１．２７ｍｍピッチ（開口部幅８００μｍ）まで広げてある。得られた基板をアセトン、“セミコクリン５６”（フルウチ化学（株）製）で各々１５分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを１５０ｎｍ蒸着した。次に、ホスト材料として化合物[２１]を、またドーパント材料として２，５，８，１１−テトラ−ｔｅｒｔ−ブチルペリレンをドープ濃度が１ｗｔ％になるように３５ｎｍの厚さに蒸着した。次に、電子輸送材料として、Ｅ−１を２０ｎｍの厚さに積層した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。次に、厚さ５０μｍのコバール板にウエットエッチングによって１６本の２５０μｍ開口部（残り幅５０μｍ、３００μｍピッチに相当）を設けたマスクを、真空中でＩＴＯストライプに直交するようにマスク交換し、マスクとＩＴＯ基板が密着するように裏面から磁石で固定した。そしてリチウムを０．５ｎｍ有機層にドーピングした後、アルミニウムを２００ｎｍ蒸着して３２×１６ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
Example 8
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) on which an ITO transparent conductive film is deposited to 150 nm is cut to 30 × 40 mm, and the ITO conductive film is 300 μm pitch (remaining width 270 μm) by photolithography. The pattern was processed into x32 stripes. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was ultrasonically washed with acetone and “Semicocrine 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes and dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, further placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 150 nm. Next, Compound [21] as a host material and 2,5,8,11-tetra-tert-butylperylene as a dopant material were vapor-deposited to a thickness of 35 nm so that the doping concentration was 1 wt%. Next, E-1 was laminated to a thickness of 20 nm as an electron transport material. The film thickness referred to here is a display value of a crystal oscillation type film thickness monitor. Next, the mask provided with 16 250 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) by wet etching on a 50 μm thick Kovar plate was replaced in a vacuum so as to be orthogonal to the ITO stripe. And it fixed with the magnet from the back so that an ITO board | substrate might contact | adhere. And after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited 200 nm, and the 32 * 16 dot matrix element was produced. When this element was driven in matrix, characters could be displayed without crosstalk.
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| KR20230122568A (en) | 2022-02-14 | 2023-08-22 | 호도가야 가가쿠 고교 가부시키가이샤 | Material to be used in photoelectric conversion element, and organic thin film |
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