JP2010222331A - Luminescent layer compound and organic electroluminescent device - Google Patents
Luminescent layer compound and organic electroluminescent device Download PDFInfo
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Abstract
【課題】 発光波長が長波長シフトしたホスト材料として用いることができる発光層化合物を提供する。
【解決手段】 一般式（１）
【化１】
（式中、Ｒ３およびＲ６の少なくとも１つはＦであり、残りはＨである）
で表される、３位および６位に１つ以上のフッ素を有するカルバゾール骨格を二量体以上含むことを特徴とする発光層化合物。
【選択図】 図１PROBLEM TO BE SOLVED: To provide a light emitting layer compound that can be used as a host material whose emission wavelength is shifted by a long wavelength.
SOLUTION: General formula (1)
[Chemical 1]
(Wherein at least one of R3 and R6 is F, and the rest is H)
A light emitting layer compound comprising a dimer or more of a carbazole skeleton having one or more fluorine atoms at the 3 and 6 positions represented by:
[Selection] Figure 1
Description
本発明は、有機電界発光素子に用いる材料および素子構成に関する。 The present invention relates to materials and device configurations used for organic electroluminescent devices.
近年、次世代ディスプレイや照明のための発光技術として有機電界発光素子（有機ＥＬ素子）が注目されている。有機ＥＬ素子の研究初期は、有機層の発光機構として主に蛍光が用いられていた。しかし、蛍光の内部量子効率は理論上２５％が上限であるとされている。実際、実験的にも、蛍光を用いた有機ＥＬ素子で２５％を超える量子効率を示す報告はほとんどなされていない。一方、リン光を用いた有機ＥＬ素子では、原理上１００％の内部量子効率が得られることが示されている。これは、蛍光が励起一重項のみからの発光であるのに対し、リン光は励起三重項からの発光が可能となり、統計的に励起三重項は励起一重項の３倍存在するためである。実際、リン光を用いた有機ＥＬ素子においては、１００％に近い内部量子効率を示す実験結果が報告されている。 In recent years, organic electroluminescent elements (organic EL elements) have attracted attention as light-emitting technologies for next-generation displays and lighting. In the early days of research on organic EL devices, fluorescence was mainly used as the light emission mechanism of the organic layer. However, the upper limit of the internal quantum efficiency of fluorescence is theoretically 25%. Actually, there has been almost no report showing a quantum efficiency exceeding 25% in an organic EL element using fluorescence. On the other hand, in an organic EL element using phosphorescence, it has been shown that an internal quantum efficiency of 100% can be obtained in principle. This is because fluorescence is emitted only from the excited singlet, whereas phosphorescence can be emitted from the excited triplet, and the excited triplet is statistically three times as many as the excited singlet. Actually, in an organic EL element using phosphorescence, an experimental result showing an internal quantum efficiency close to 100% has been reported.
近年におけるリン光を用いた発光層の構成の主流は、有機材料からなるホスト材料中に、イリジウムや白金などを中心金属とする発光性金属錯体をドープしたものである。このリン光発光層中の発光ドーパントにおける励起子生成のメカニズムの１つは以下の通りである。すなわち、陰極と陽極からの電子と正孔の注入により生成したホスト材料の励起状態から、発光ドーパントへエネルギー移動を起こすことによって発光ドーパントが励起状態となり、その基底状態へのエネルギー失活過程において発光を示す。 In recent years, the mainstream of the structure of a light emitting layer using phosphorescence is that a host material made of an organic material is doped with a light emitting metal complex having iridium or platinum as a central metal. One of the mechanisms of exciton generation in the luminescent dopant in the phosphorescent layer is as follows. In other words, the luminescent dopant becomes excited by causing energy transfer from the excited state of the host material generated by the injection of electrons and holes from the cathode and anode to the luminescent dopant, and emits light in the energy deactivation process to its ground state. Indicates.
このような発光層では、ホスト材料の発光スペクトルと発光ドーパントの吸収スペクトルの重なりが大きいほど、ホスト材料から発光ドーパントへのエネルギー移動効率がよい。これは、フェルスターのエネルギー移動機構と呼ばれる。 In such a light emitting layer, the larger the overlap between the emission spectrum of the host material and the absorption spectrum of the luminescent dopant, the better the energy transfer efficiency from the host material to the luminescent dopant. This is called Förster energy transfer mechanism.
リン光を用いた発光層のホスト材料は、低分子系と高分子系に大別される。低分子系ホスト材料を含む発光層は、主に低分子系ホスト材料および発光ドーパントを真空共蒸着することによって成膜される。高分子系ホスト材料を含む発光層は、主に高分子系ホスト材料および発光ドーパントを混合した溶液を塗布することによって成膜される。 The host material of the light emitting layer using phosphorescence is roughly classified into a low molecular weight type and a high molecular weight type. The light emitting layer containing the low molecular weight host material is formed mainly by vacuum co-evaporation of the low molecular weight host material and the light emitting dopant. The light emitting layer containing the polymer host material is formed mainly by applying a solution in which the polymer host material and the light emitting dopant are mixed.
低分子系ホスト材料の代表例は、パラビスカルバゾリルフェニレン（ＣＢＰ）などである。高分子系ホスト材料の代表例は、ポリビニルカルバゾール（ＰＶＫ）などである（非特許文献１、非特許文献２）。下記に、ＣＢＰおよびＰＶＫの構造を示す。
発光ドーパント材料には、青色発光ドーパント材料、緑色発光ドーパント材料、赤色発光ドーパント材料などがある。青色発光ドーパント材料の代表例はビス（２−（４，６−ジフルオレフェニル）ピリジナートイリジウム錯体［以下、ＦＩｒｐｉｃと記す］などである。緑色発光ドーパント材料の代表例はトリス（２−フェニルピリジン）イリジウム錯体［以下、Ｉｒ（ｐｐｙ）3と記す］などである。赤色発光ドーパント材料の代表例はＢｔ2Ｉｒ（ａｃａｃ）などである。 Examples of the light emitting dopant material include a blue light emitting dopant material, a green light emitting dopant material, and a red light emitting dopant material. A typical example of a blue light-emitting dopant material is a bis (2- (4,6-difluorphenyl) pyridinatoiridium complex [hereinafter referred to as FIrpic], etc. A typical example of a green light-emitting dopant material is tris (2-phenyl). Pyridine) iridium complex [hereinafter referred to as Ir (ppy) 3 ], etc. A typical example of a red light emitting dopant material is Bt 2 Ir (acac).
これらの発光ドーパント材料と高分子系ホスト材料であるＰＶＫとを含む発光層を成膜することを想定する。ＰＶＫの発光波長が４２０ｎｍであるのに対し、それぞれの発光ドーパント材料の吸収波長は、青色発光ドーパント材料であるＦＩｒｐｉｃで３８０ｎｍ、緑色発光ドーパント材料であるＩｒ（ｐｐｙ）3で４１０ｎｍ、赤色発光ドーパント材料であるＢｔ2Ｉｒ（ａｃａｃ）で４８０ｎｍとなっている。したがって、たとえばＰＶＫからＢｔｐ2Ｉｒ（ａｃａｃ）へのエネルギー移動を効率よく行わせたい場合には、ＰＶＫの発光波長を長波長シフトさせることが望ましい。 It is assumed that a light-emitting layer containing these light-emitting dopant materials and PVK that is a polymer host material is formed. While the emission wavelength of PVK is 420 nm, the absorption wavelength of each light emitting dopant material is 380 nm for FIrpic which is a blue light emitting dopant material, 410 nm for Ir (ppy) 3 which is a green light emitting dopant material, and a red light emitting dopant material Bt 2 Ir (acac) is 480 nm. Therefore, for example, when it is desired to efficiently transfer energy from PVK to Btp 2 Ir (acac), it is desirable to shift the emission wavelength of PVK by a long wavelength.
本発明の目的は、発光波長が長波長シフトしたホスト材料として用いることができる発光層化合物、およびこの発光層化合物を発光層に含む有機電界発光素子を提供することにある。 An object of the present invention is to provide a light emitting layer compound that can be used as a host material whose emission wavelength is shifted by a long wavelength, and an organic electroluminescence device comprising the light emitting layer compound in the light emitting layer.
本発明の一実施形態によれば、一般式（１）
（式中、Ｒ３およびＲ６の少なくとも１つはＦであり、残りはＨである）
で表される、３位および６位に１つ以上のフッ素を有するカルバゾール骨格を二量体以上含むことを特徴とする発光層化合物が提供される。
(Wherein at least one of R3 and R6 is F, and the rest is H)
A light emitting layer compound comprising a carbazole skeleton having one or more fluorine atoms at the 3-position and the 6-position represented by the formula:
本発明の他の実施形態によれば、陽極と陰極との間に発光層を有し、前記発光層は、前記の発光層化合物からなるホスト材料と、赤色発光ドーパントとを含有することを特徴とする有機電界発光素子が提供される。 According to another embodiment of the present invention, a light emitting layer is provided between an anode and a cathode, and the light emitting layer contains a host material composed of the light emitting layer compound and a red light emitting dopant. An organic electroluminescent element is provided.
本発明の実施形態に係る発光層化合物は、発光波長が長波長シフトしたホスト材料として用いることができ、赤色発光ドーパント材料へのエネルギー移動効率を向上できる。また、本発明の実施形態に係る有機電界発光素子は、前記発光層化合物からなるホスト材料と赤色発光ドーパントとを含有する発光層を有し、高い発光効率を得ることができる。 The light emitting layer compound according to the embodiment of the present invention can be used as a host material whose emission wavelength is shifted by a long wavelength, and can improve the energy transfer efficiency to the red light emitting dopant material. Moreover, the organic electroluminescent element which concerns on embodiment of this invention has a light emitting layer containing the host material which consists of the said light emitting layer compound, and a red light emitting dopant, and can obtain high luminous efficiency.
以下、本発明の実施形態を説明する。
本発明の実施形態に係る発光層化合物は、３位および６位に１つ以上のフッ素を有するカルバゾール骨格を二量体以上含む。下記に、カルバゾールと、３，６−ジフルオロカルバゾールの構造を示す。
The light emitting layer compound according to the embodiment of the present invention includes a dimer or more of a carbazole skeleton having one or more fluorine atoms at the 3-position and the 6-position. The structures of carbazole and 3,6-difluorocarbazole are shown below.
分子軌道計算によれば、３，６−ジフルオロカルバゾールの発光波長は、無置換カルバゾールの発光波長に比べて、約２８ｎｍ長波長シフトすることがわかっている。具体的には以下の通りである。 According to molecular orbital calculation, it is known that the emission wavelength of 3,6-difluorocarbazole is shifted by about 28 nm longer than the emission wavelength of unsubstituted carbazole. Specifically, it is as follows.
分子軌道計算は、分子軌道計算ソフトであるｇａｕｓｓｉｎ０３を用いて行い、基底状態についての構造最適化は、Ｂ３ＬＹＰ法（基底関数は６−３１Ｇ*）で行った。励起子の構造最適化はＣＩＳ法（基底関数は６−３１Ｇ*）で行い、その最適構造を使ってＴＤ−ＤＦＴ（時間依存密度汎関数法）計算を行うことで発光波長を算出した。その結果、無置換カルバゾールの発光波長は３３４ｎｍ、３，６−ジフルオロカルバゾールの発光波長は３０６ｎｍであり、長波長シフトは約２８ｎｍとなった。 Molecular orbital calculation was performed using gaussin03, which is molecular orbital calculation software, and structure optimization for the ground state was performed by the B3LYP method (basic function was 6-31G *). The structure of the exciton was optimized by the CIS method (basic function was 6-31G *), and the emission wavelength was calculated by performing TD-DFT (time-dependent density functional theory) calculation using the optimal structure. As a result, the emission wavelength of unsubstituted carbazole was 334 nm, the emission wavelength of 3,6-difluorocarbazole was 306 nm, and the long wavelength shift was about 28 nm.
また、下記に、３，６−ジフルオロカルバゾールを含む二量体およびポリマーを示す。
したがって、前記一般式（１）で表される発光層化合物からなるホスト材料は、赤色発光ドーパント材料へのエネルギー移動効率を向上できる。また、前記一般式（１）で表される発光層化合物からなるホスト材料と赤色発光ドーパントとを含有する発光層を有する有機電界発光素子は、高い発光効率を得ることができる。 Therefore, the host material comprising the light emitting layer compound represented by the general formula (1) can improve the energy transfer efficiency to the red light emitting dopant material. Moreover, the organic electroluminescent element which has a light emitting layer containing the host material which consists of a light emitting layer compound represented by the said General formula (1), and a red light emitting dopant can obtain high luminous efficiency.
以下、図面を参照しながら、本発明の実施例を説明する。
図１に本実施例に係る白色有機ＥＬ素子の断面図を示す。ガラス基板１上に、陽極２、青色発光層３、赤色発光層４、および陰極５が順次形成されている。なお、陽極２と青色発光層３との間に正孔注入層や正孔輸送層を設けてもよいし、赤色発光層４と陰極５との間に電子輸送層や電子注入層を設けてもよい。
Embodiments of the present invention will be described below with reference to the drawings.
FIG. 1 shows a cross-sectional view of a white organic EL element according to this example. On the
陰極２の材料には、たとえばＩＴＯ（インジウム錫酸化物）が用いられる。必要に応じて設けられる正孔輸送層の材料には、たとえばポリ（エチレンジオキシチオフェン）：ポリ（スチレン・スルフォン酸）［ＰＥＤＯＴ：ＰＳＳ］が用いられる。
For example, ITO (indium tin oxide) is used as the material of the
青色発光層３の材料には、下記に示すようにホスト材料としてポリ（ビニル−２，７−ジフルオロカルバゾール）、および青色リン光発光ドーパントとしてＦＩｒｐｉｃが用いられる。これらを有機溶媒に溶解した溶液をスピンコートによって塗布し、加熱して乾燥することにより青色発光層３を形成する。
図２に２，７−ジフルオロカルバゾールと無置換カルバゾールの発光スペクトルを示す。図２に示されるように、２，７−ジフルオロカルバゾールでは、無置換カルバゾールと比較して、発光波長が短波長シフトする。したがって、ポリ（ビニル−２，７−ジフルオロカルバゾール）の発光スペクトルとＦＩｒｐｉｃの吸収スペクトルとの重なりが大きく、ホスト材料から発光ドーパントへのエネルギー移動効率がよいため、発光効率が高くなる。 FIG. 2 shows emission spectra of 2,7-difluorocarbazole and unsubstituted carbazole. As shown in FIG. 2, in 2,7-difluorocarbazole, the emission wavelength is shifted by a short wavelength compared to unsubstituted carbazole. Therefore, the overlap between the emission spectrum of poly (vinyl-2,7-difluorocarbazole) and the absorption spectrum of FIrpic is large, and the energy transfer efficiency from the host material to the emission dopant is good, so that the emission efficiency is increased.
赤色発光層４の材料には、下記に示すようにホスト材料としてポリ（ビニル−３，６−ジフルオロカルバゾール）、および赤色リン光発光ドーパントとしてＢｔ2Ｉｒ（ａｃａｃ）が用いられる。これらを有機溶媒に溶解した溶液をスピンコートによって塗布し、加熱して乾燥することにより赤色発光層４を形成する。
前記のように、３，６−ジフルオロカルバゾールの発光波長は、無置換カルバゾールの発光波長に比べて、約２８ｎｍ長波長シフトする。したがって、ポリ（ビニル−３，６−ジフルオロカルバゾール）の発光スペクトルとＢｔ2Ｉｒ（ａｃａｃ）の吸収スペクトルとの重なりが大きく、ホスト材料から発光ドーパントへのエネルギー移動効率がよいため、発光効率が高くなる。 As described above, the emission wavelength of 3,6-difluorocarbazole is shifted by about 28 nm longer than the emission wavelength of unsubstituted carbazole. Therefore, there is a large overlap between the emission spectrum of poly (vinyl-3,6-difluorocarbazole) and the absorption spectrum of Bt 2 Ir (acac), and the energy transfer efficiency from the host material to the emission dopant is good, resulting in high emission efficiency. Become.
必要に応じて設けられる電子輸送層の材料には、たとえばトリス（８−ヒドロキシキノリナト）アルミニウム［Ａｌｑ3］が用いられる。必要に応じて設けられる電子注入層の材料には、たとえばＬｉＦが用いられる。陰極５の材料には、たとえばＡｌが用いられる。
For example, tris (8-hydroxyquinolinato) aluminum [Alq 3 ] is used as a material for the electron transport layer provided as necessary. For example, LiF is used as the material of the electron injection layer provided as necessary. For example, Al is used as the material of the
上述した青色発光層３および赤色発光層４の発光効率が高いので、高効率の白色有機ＥＬ素子を提供できる。 Since the blue light emitting layer 3 and the red light emitting layer 4 described above have high light emission efficiency, a highly efficient white organic EL element can be provided.
青色発光層３および赤色発光層４のホスト材料が類似の構造を有するので、成膜性が良好であり、しかも界面が安定になり構造欠陥を抑制することができる。 Since the host materials of the blue light-emitting layer 3 and the red light-emitting layer 4 have a similar structure, the film formability is good, and the interface becomes stable and structural defects can be suppressed.
１…ガラス基板、２…陽極、３…青色発光層、４…赤色発光層、５…陰極。
DESCRIPTION OF
Claims (3)
で表される、３位および６位に１つ以上のフッ素を有するカルバゾール骨格を二量体以上含むことを特徴とする発光層化合物。 General formula (1)
A light emitting layer compound comprising a dimer or more of a carbazole skeleton having one or more fluorine atoms at the 3 and 6 positions represented by:
で表される、２位、４位、５位および７位に２つ以上のフッ素を有するカルバゾール骨格を二量体以上含む発光層化合物からなるホスト材料と、青色発光ドーパントとを含有する別の発光層をさらに有することを特徴とする請求項２に記載の有機電界発光素子。 General formula (2) laminated on the light emitting layer.
A host material composed of a light-emitting layer compound containing a dimer or more of a carbazole skeleton having two or more fluorine atoms at the 2nd, 4th, 5th and 7th positions, and a blue light emitting dopant The organic electroluminescent device according to claim 2, further comprising a light emitting layer.
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| JP2011061028A (en) * | 2009-09-10 | 2011-03-24 | Toshiba Corp | Organic electroluminescence device |
| JP2012186460A (en) * | 2011-02-16 | 2012-09-27 | Semiconductor Energy Lab Co Ltd | Light-emitting element |
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| KR101758414B1 (en) | 2010-05-11 | 2017-07-14 | 메르크 파텐트 게엠베하 | Organic electroluminescent devices |
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