JP2007314512A - Organic compound and organic light-emitting device - Google Patents
Organic compound and organic light-emitting device Download PDFInfo
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 39
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Abstract
Description
本発明は、新規有機化合物およびそれを有する有機発光素子に関し、詳しくは有機化合物からなる薄膜に電界を印加することにより光を放出する素子に関する。 The present invention relates to a novel organic compound and an organic light-emitting device having the same, and more particularly to a device that emits light by applying an electric field to a thin film made of an organic compound.
有機発光素子は,古くはアントラセン蒸着膜に電圧を印加して発光させた例(非特許文献1)等がある。 In the past, there has been an example in which an organic light emitting element emits light by applying a voltage to an anthracene vapor deposition film (Non-patent Document 1).
他にも非特許文献2に詳述されているように、一般に有機EL素子は透明基板上に形成された、上下2層の電極と、この間に発光層を含む有機物層が形成された構成を持つ。 In addition, as described in detail in Non-Patent Document 2, an organic EL element generally has a configuration in which an upper and lower two layers of electrodes are formed on a transparent substrate, and an organic material layer including a light emitting layer is formed therebetween. Have.
また、蛍光性有機化合物の種類を変えることにより、紫外から赤外までの発光が可能であり、最近では様々な化合物の研究が活発に行われている。 In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched.
さらに、上記のような低分子材料を用いた有機発光素子の他にも、共役系高分子を用いた有機発光素子が、ケンブリッジ大学のグループ(非特許文献3)により報告されている。この報告ではポリフェニレンビニレン(PPV)を塗工系で成膜することにより、単層で発光を確認している。 Furthermore, in addition to the organic light-emitting device using the low-molecular material as described above, an organic light-emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 3). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system.
このように有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。 As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.
しかしながら、現状では更なる高輝度の光出力あるいは高変換効率が必要である。また、長時間の使用による経時変化や酸素を含む雰囲気気体や湿気などによる劣化等の耐久性の面で未だ多くの問題がある。さらにはフルカラーディスプレイ等への応用を考えた場合の色純度の良い青、緑、赤の発光が必要となるが、これらの問題に関してもまだ十分でない。 However, under the present circumstances, light output with higher brightness or higher conversion efficiency is required. In addition, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Furthermore, it is necessary to emit blue, green, and red light with good color purity when considering application to a full color display or the like, but these problems are still not sufficient.
また、電子輸送層や発光層などに用いる蛍光性有機化合物として、芳香族化合物や縮合多環芳香族化合物が数多く研究されているが、発光輝度や耐久性が十分に満足できるものは得られているとは言いがたい。 In addition, many aromatic organic compounds and condensed polycyclic aromatic compounds have been studied as fluorescent organic compounds for use in the electron transport layer, the light emitting layer, and the like. It's hard to say.
本発明に関連するフルオレン化合物の有機ELへの応用の特許文献として特許文献1が挙げられる。この特許文献においては、フルオレン環に対してフェナントレン環を結合させた化合物やフルオレン環に対して両端にフェナントレン環を結合させた化合物等の記載がある。しかし、オリゴフルオレン環とフェナントレン環からなることを特徴とする本発明の有機化合物の開示はない。
本発明の目的は、新規なフルオレン誘導体を提供することにある。 An object of the present invention is to provide a novel fluorene derivative.
また本発明の目的は、特定なフルオレン誘導体を用い、極めて高効率で高輝度な光出力を有する有機発光素子を提供することにある。また、極めて耐久性のある有機発光素子を提供することにある。 Another object of the present invention is to provide an organic light emitting device using a specific fluorene derivative and having a light output with extremely high efficiency and high luminance. Another object of the present invention is to provide an extremely durable organic light emitting device.
よって本発明は、
下記一般式[1]で示されることを特徴とする有機化合物を提供する。
Therefore, the present invention
An organic compound represented by the following general formula [1] is provided.
[式中R1、R2、R3は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基を表し、同じであっても異なっていてもよい。nは、2から10の何れかの整数を表す。また、複数存在するR2及びR3はそれぞれ同じであっても異なっていてもよい。さらに、Ar1は置換もしくは未置換のフェナントレン構造を表す。]
また本発明は、
下記一般式[2]で示されることを特徴とする有機化合物を提供する。
[Wherein R 1 , R 2 and R 3 each independently represents a hydrogen atom, a halogen atom or a substituted or unsubstituted alkyl group, and may be the same or different. n represents any integer of 2 to 10. A plurality of R 2 and R 3 may be the same or different. Ar 1 represents a substituted or unsubstituted phenanthrene structure. ]
The present invention also provides
An organic compound represented by the following general formula [2] is provided.
[式中R4からR15は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基を表し、同じであっても異なっていてもよい。mは、2から10の何れかの整数を表す。また、複数存在するR5及びR6はそれぞれ同じであっても異なっていてもよい。]
また本発明は、
下記一般式[3]で示されることを特徴とする有機化合物を提供する。
[Wherein R 4 to R 15 each independently represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group, and may be the same or different. m represents an integer of 2 to 10. A plurality of R 5 and R 6 may be the same or different. ]
The present invention also provides
An organic compound represented by the following general formula [3] is provided.
[式中R16からR27は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基(を表し、同じであっても異なっていてもよい。lは、2から10の何れかの整数を表す。また、複数存在するR17及びR18はそれぞれ同じであっても異なっていてもよい。]
また本発明は、
少なくとも一方が透明か半透明な陽極および陰極からなる一対の電極間に挟持された一層または複数層の有機化合物層より構成される有機発光素子において、前記有機化合物層のうち少なくとも一層が、一般式[1]乃至[3]のいずれかに記載の前記有機化合物を含有することを特徴とする有機発光素子を提供する。
[Wherein R 16 to R 27 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group (may be the same or different. L is any one of 2 to 10] And a plurality of R 17 and R 18 may be the same or different.]
The present invention also provides
In an organic light-emitting device composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes consisting of a transparent or semi-transparent anode and cathode, at least one of the organic compound layers is represented by the general formula An organic light-emitting device comprising the organic compound according to any one of [1] to [3] is provided.
また本発明は、
少なくとも一方が透明か半透明な陽極および陰極からなる一対の電極間に挟持された一層または複数層の有機化合物層より構成される有機発光素子において、前記一層または複数層の有機化合物層のうちの発光層が一般式[1]乃至[3]のいずれかに記載の有機化合物を含有することを特徴とする有機発光素子を提供する。
The present invention also provides
In the organic light-emitting device composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes, at least one of which is a transparent or translucent anode and cathode, of the one or more organic compound layers. Provided is an organic light emitting device characterized in that a light emitting layer contains the organic compound described in any one of the general formulas [1] to [3].
本発明の一般式[1]から[3]で示される有機化合物は、優れた有機発光素子を提供するための新規材料である。そしてそれを有する有機発光素子は、低い印加電圧で高効率な発光を与えた。更には、優れた耐久性も得られる。 The organic compounds represented by the general formulas [1] to [3] of the present invention are novel materials for providing an excellent organic light emitting device. And the organic light emitting element which has it gave highly efficient light emission with the low applied voltage. Furthermore, excellent durability is also obtained.
本発明に係る有機化合物は、
下記一般式[1]で示されることを特徴とする有機化合物である。
The organic compound according to the present invention is
It is an organic compound characterized by being represented by the following general formula [1].
[式中R1、R2、R3は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基を表し、同じであっても異なっていてもよい。nは、2から10の何れかの整数を表す。また、複数存在するR2及びR3はそれぞれ同じであっても異なっていてもよい。さらに、Ar1は置換もしくは未置換のフェナントレン構造を表す。]
あるいは本発明に係る有機化合物は、
下記一般式[2]で示されることを特徴とする有機化合物である。
[Wherein R 1 , R 2 and R 3 each independently represents a hydrogen atom, a halogen atom or a substituted or unsubstituted alkyl group, and may be the same or different. n represents any integer of 2 to 10. A plurality of R 2 and R 3 may be the same or different. Ar 1 represents a substituted or unsubstituted phenanthrene structure. ]
Alternatively, the organic compound according to the present invention is
It is an organic compound characterized by being represented by the following general formula [2].
[式中R4からR15は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基を表し、同じであっても異なっていてもよい。mは、2から10の何れかの整数を表す。また、複数存在するR5及びR6はそれぞれ同じであっても異なっていてもよい。]
あるいは本発明に係る有機化合物は、
下記一般式[3]で示されることを特徴とする有機化合物である。
[Wherein R 4 to R 15 each independently represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group, and may be the same or different. m represents an integer of 2 to 10. A plurality of R 5 and R 6 may be the same or different. ]
Alternatively, the organic compound according to the present invention is
It is an organic compound characterized by being represented by the following general formula [3].
[式中R16からR27は、それぞれ独立に水素原子、ハロゲン原子、置換または未置換のアルキル基(を表し、同じであっても異なっていてもよい。lは、2から10の何れかの整数を表す。また、複数存在するR17及びR18はそれぞれ同じであっても異なっていてもよい。]
また本発明に係る有機発光素子は、
少なくとも一方が透明か半透明な陽極および陰極からなる一対の電極間に挟持された一層または複数層の有機化合物層より構成される有機発光素子において、前記有機化合物層のうち少なくとも一層が、一般式[1]乃至[3]のいずれかに記載の前記有機化合物を含有することを特徴とする有機発光素子である。
[Wherein R 16 to R 27 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group (may be the same or different. L is any one of 2 to 10] And a plurality of R 17 and R 18 may be the same or different.]
The organic light emitting device according to the present invention is
In an organic light-emitting device composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes consisting of a transparent or semi-transparent anode and cathode, at least one of the organic compound layers is represented by the general formula [1] An organic light-emitting device comprising the organic compound according to any one of [3].
またあるいは本発明に係る有機発光素子は、
少なくとも一方が透明か半透明な陽極および陰極からなる一対の電極間に挟持された一層または複数層の有機化合物層より構成される有機発光素子において、前記一層または複数層の有機化合物層のうちの発光層が一般式[1]乃至[3]のいずれかに記載の有機化合物を含有することを特徴とする有機発光素子である。
Alternatively, the organic light-emitting device according to the present invention is
In the organic light-emitting device composed of one or more organic compound layers sandwiched between a pair of electrodes, at least one of which is a transparent or translucent anode and cathode, of the one or more organic compound layers. An organic light-emitting device, wherein the light-emitting layer contains the organic compound according to any one of the general formulas [1] to [3].
以下更に説明する。 This will be further described below.
発光層が、キャリア輸送性のホスト材料とゲストからなる場合、発光にいたる主な過程は、以下のいくつかの過程からなる。
1.発光層内でのキャリアの輸送
2.ホストの励起子生成
3.ホスト分子間の励起エネルギー伝達
4.ホストからゲストへの励起エネルギー移動
EL素子の発光効率を高めるためには、発光中心材料そのものの発光量子収率が大きいことは言うまでもない。しかしながら、ホスト−ホスト間、あるいはホスト−ゲスト間のエネルギー移動が如何に効率的にできるかも大きな問題となる。また、通電による発光劣化は今のところ原因は明らかではないが、少なくとも発光中心材料そのもの、または、その周辺分子による発光材料の環境変化に関連したものと想定される。
When the light emitting layer is composed of a carrier material having a carrier transport property and a guest, the main process leading to light emission includes the following several processes.
1. 1. Transport of carriers in the light emitting layer 2. Host exciton generation 3. Excitation energy transfer between host molecules Excitation energy transfer from host to guest It goes without saying that the emission quantum yield of the luminescent center material itself is large in order to increase the luminous efficiency of the EL element. However, how to efficiently transfer energy between the host and the host or between the host and the guest is also a big problem. Further, although the cause of light emission deterioration due to energization is not clear at present, it is assumed that it is related to the environmental change of the light emitting material due to at least the luminescent center material itself or its peripheral molecules.
しかし、発光の失活は、上記1から4で示した過程において競合でおこっていると考えると、特に発光層ホストにおいては、ゲスト材料に合わせたキャリア輸送性等の性能を調整することも求められる。 However, considering that the deactivation of light emission is caused by competition in the processes shown in 1 to 4 above, it is also required to adjust the performance such as carrier transportability in accordance with the guest material, particularly in the light emitting layer host. It is done.
ここで本発明者らは、発光層ホストのキャリアの輸送性を調整するために、本発明の化合物を分子設計するに至った。通電による発光劣化を抑制するためには、駆動電圧を低下させることがまず挙げられる。発光層の分子形状において、分子同士の共役面の重なり合いが大きいと移動度が向上し、駆動電圧は低くなることが予想される。。この点から分子同士の重なりを有する骨格を持った分子設計が必要であると考えられる。 Here, the present inventors have molecularly designed the compound of the present invention in order to adjust the carrier transport property of the light emitting layer host. In order to suppress light emission deterioration due to energization, firstly, the drive voltage is lowered. In the molecular shape of the light emitting layer, it is expected that when the overlap of the conjugate planes between the molecules is large, the mobility is improved and the driving voltage is lowered. . From this point of view, it is considered necessary to design a molecule having a skeleton with overlapping molecules.
例えば、オリゴフルオレン化合物は直鎖状の骨格であるため、分子同士の重なり合いが大きく薄膜とした際、高移動度であるといえる。 For example, since an oligofluorene compound has a linear skeleton, it can be said that when a thin film having a large overlap between molecules is formed, the mobility is high.
本発明の化合物は、オリゴフルオレニル基に対してさらにフェナントレニル基を導入した化合物である。一般式(1)で示したように、フェナントレニル基とフルオレニル基の2量体から10量体までをそれぞれ結合させた化合物である。分子内に含まれるフルオレニル基の数が多いほど、薄膜とした際、分子同士の重なり合いが大きく、高移動度であることは予想される。 The compound of the present invention is a compound in which a phenanthrenyl group is further introduced to the oligofluorenyl group. As shown in the general formula (1), it is a compound in which a dimer to a 10-mer of a phenanthrenyl group and a fluorenyl group are bonded to each other. It is expected that the greater the number of fluorenyl groups contained in the molecule, the greater the overlap between the molecules in the thin film, and the higher the mobility.
一般式(1)で表される化合物は、前記のようにフルオレニル基の数を増やすことで移動度の向上させることが出来る。さらに、フェナントレニル基を導入することで、直鎖状構造をくずし、フルオレニル基の数を増減するだけでは成し得ないような移動度の調整をすることが出来る。 The compound represented by the general formula (1) can improve mobility by increasing the number of fluorenyl groups as described above. Furthermore, by introducing a phenanthrenyl group, it is possible to adjust the mobility that cannot be achieved simply by breaking the linear structure and increasing or decreasing the number of fluorenyl groups.
以上のような思想が本発明の主旨であるが、ただし、移動度を下げすぎると、駆動電圧が高くなり、発光劣化をしやすくなる。 The above idea is the gist of the present invention. However, if the mobility is lowered too much, the driving voltage becomes high and the light emission is easily deteriorated.
例えば、特許文献1において記載がある(例えば、化合物Eや化合物Gなど)化合物は、オリゴフルオレニル基を分子内に含まないため、本発明の化合物より移動度の低下が予想される。 For example, compounds described in Patent Document 1 (for example, Compound E and Compound G) do not contain an oligofluorenyl group in the molecule, and thus are expected to have lower mobility than the compounds of the present invention.
まず、化合物Eに対して本発明の化合物(例えば、化合物Fなど)は、フルオレン環を2つ以上有することで、直鎖状部分を多く含むため、分子同士の重なり合いが大きく薄膜とした際、より高移動度であることが予想される。 First, the compound of the present invention (for example, compound F etc.) with respect to compound E has two or more fluorene rings and contains a lot of linear portions. Higher mobility is expected.
化合物Gに対しても、本発明の化合物は、直鎖状部分を多く含むため、より高移動度であることが予想される。 Also with respect to compound G, the compound of the present invention contains a large amount of linear moieties, and thus is expected to have higher mobility.
このことから本発明のオリゴフルオレン環にフェナントレン環を導入した化合物は、ホスト材料として移動度の面でより有利であり、駆動電圧の低下も期待できる。 From this, the compound which introduce | transduced the phenanthrene ring into the oligofluorene ring of this invention is more advantageous in terms of the mobility as a host material, and the fall of a drive voltage can also be anticipated.
オリゴフルオレンに結合させるフェナントレン環の置換位置としては、安価に合成でき得る3位あるいは9位置換が主に挙げられる。そのうち、共役面の重なり合いの大きさを考慮するとフェナントレン環の3位にオリゴフルオレンを結合させた化合物が移動度の面でより有利といえる。 The substitution position of the phenanthrene ring to be bonded to oligofluorene mainly includes substitution at the 3-position or the 9-position, which can be synthesized at low cost. Of these, considering the size of the overlap of the conjugate planes, a compound in which oligofluorene is bonded to the 3-position of the phenanthrene ring is more advantageous in terms of mobility.
本発明の化合物は、以上のような考察をもとにも分子設計がなされている。 The compound of the present invention has been molecularly designed based on the above consideration.
本発明の化合物はこのように発光層に用いる事が効果的であるが、電子輸送層、正孔輸送層、電子阻止層、正孔阻止層、電子注入層、正孔注入層としても有効である。 The compound of the present invention is thus effective for use in the light emitting layer, but is also effective as an electron transport layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, and a hole injection layer. is there.
本発明の化合物を含む有機層を作製する場合は、真空蒸着法、キャスト法、塗布法、スピンコート法、インクジェット法などにより製膜することができる。 When an organic layer containing the compound of the present invention is produced, it can be formed by a vacuum deposition method, a casting method, a coating method, a spin coating method, an ink jet method, or the like.
本発明の基本的な素子構成を図1(a)(b)(c)に示した。
図中符号11は金属電極、12は発光層、13はホール輸送層、14は透明電極、15は透明基板、16は電子輸送層、17は励起子拡散防止層である。
The basic element configuration of the present invention is shown in FIGS. 1 (a), (b) and (c).
In the figure, 11 is a metal electrode, 12 is a light emitting layer, 13 is a hole transport layer, 14 is a transparent electrode, 15 is a transparent substrate, 16 is an electron transport layer, and 17 is an exciton diffusion preventing layer.
図1に示したように、一般に有機EL素子は透明基板15上に、50nm以上200nm以下の膜厚を持つ透明電極14と、複数層の有機膜層と、及びこれを挟持するように金属電極11が形成される。 As shown in FIG. 1, in general, an organic EL element is formed on a transparent substrate 15 with a transparent electrode 14 having a film thickness of 50 nm or more and 200 nm or less, a plurality of organic film layers, and a metal electrode so as to sandwich them. 11 is formed.
図1(a)では、有機層が発光層12とホール輸送層13からなる例を示した。透明電極14としては、仕事関数が大きなITOなどが用いられ、透明電極14からホール輸送層13へホール注入しやすくしている。金属電極11には、アルミニウム、マグネシウムあるいはそれらを用いた合金など、仕事関数の小さな金属材料を用い、有機層への電子注入をしやすくしている。 FIG. 1A shows an example in which the organic layer is composed of the light emitting layer 12 and the hole transport layer 13. As the transparent electrode 14, ITO or the like having a large work function is used to facilitate hole injection from the transparent electrode 14 into the hole transport layer 13. The metal electrode 11 is made of a metal material having a small work function, such as aluminum, magnesium, or an alloy using them, to facilitate electron injection into the organic layer.
発光層12には、本発明の化合物を用いているが、ホール輸送層13には,例えばトリフェニルジアミン誘導体、代表例としてはα−NPDなど、電子供与性を有する材料も適宜用いることができる。 For the light emitting layer 12, the compound of the present invention is used. For the hole transporting layer 13, for example, a material having an electron donating property such as a triphenyldiamine derivative, typically α-NPD, can be used as appropriate. .
以上の構成した素子は電気的整流性を示し、金属電極11を陰極に透明電極14を陽極になるように電界を印加すると、金属電極11から電子が発光層12に注入され、透明電極15からはホールが注入される。 The element configured as described above exhibits electrical rectification. When an electric field is applied so that the metal electrode 11 serves as a cathode and the transparent electrode 14 serves as an anode, electrons are injected from the metal electrode 11 into the light-emitting layer 12 and from the transparent electrode 15. Holes are injected.
注入されたホールと電子は、発光層12内で再結合して励起子が生じ、発光する。この時ホール輸送層13は電子のブロッキング層の役割を果たし、発光層12とホール輸送層13の間の界面における再結合効率が上がり、発光効率が上がる。 The injected holes and electrons recombine in the light emitting layer 12 to generate excitons and emit light. At this time, the hole transport layer 13 serves as an electron blocking layer, and the recombination efficiency at the interface between the light emitting layer 12 and the hole transport layer 13 is increased, and the light emission efficiency is increased.
さらに図1(b)では、図1(a)の金属電極11と発光層12の間に、電子輸送層16が設けられている。発光機能と電子及びホール輸送機能を分離して、より効果的なキャリアブロッキング構成にすることで、発光効率を上げている。電子輸送層16としては、例えばオキサジアゾール誘導体などを用いることができる。 Further, in FIG. 1B, an electron transport layer 16 is provided between the metal electrode 11 and the light emitting layer 12 in FIG. Luminous efficiency is increased by separating the light emitting function and the electron and hole transporting function to form a more effective carrier blocking structure. As the electron transport layer 16, for example, an oxadiazole derivative or the like can be used.
また図1(c)に示すように、陽極である透明電極14側から、ホール輸送層13、発光層12、励起子拡散防止層17、電子輸送層16、及び金属電極11からなる4層構成とすることも望ましい形態である。 Further, as shown in FIG. 1C, a four-layer structure including a hole transport layer 13, a light emitting layer 12, an exciton diffusion preventing layer 17, an electron transport layer 16, and a metal electrode 11 from the transparent electrode 14 side that is an anode. It is also a desirable form.
上記一般式[1]−[3]における置換基の具体例を以下に示す。 Specific examples of the substituent in the general formulas [1] to [3] are shown below.
ハロゲン原子としては、フッ素、塩素、臭素、ヨウ素などが挙げられる。 Examples of the halogen atom include fluorine, chlorine, bromine and iodine.
置換あるいは未置換のアルキル基としては、メチル基、メチル−d1基、メチル−d3基、エチル基、エチル−d5基、n−プロピル基、n−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−デシル基、iso−プロピル基、iso−プロピル−d7基、iso−ブチル基、sec−ブチル基、tert−ブチル基、tert−ブチル−d9基、iso−ペンチル基、ネオペンチル基、tert−オクチル基、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、2−フルオロエチル基、2,2,2−トリフルオロエチル基、パーフルオロエチル基、3−フルオロプロピル基、パーフルオロプロピル基、4−フルオロブチル基、パーフルオロブチル基、5−フルオロペンチル基、6−フルオロヘキシル基、クロロメチル基、トリクロロメチル基、2−クロロエチル基、2,2,2−トリクロロエチル基、4−クロロブチル基、5−クロロペンチル基、6−クロロヘキシル基、ブロモメチル基、2−ブロモエチル基、ヨードメチル基、2−ヨードエチル基、ヒドロキシメチル基、ヒドロキシエチル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロペンチルメチル基、シクロヘキシルメチル基、シクロヘキシルエチル基、4−フルオロシクロヘキシル基、ノルボルニル基、アダマンチル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the substituted or unsubstituted alkyl group include a methyl group, a methyl-d1 group, a methyl-d3 group, an ethyl group, an ethyl-d5 group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group. N-heptyl group, n-octyl group, n-decyl group, iso-propyl group, iso-propyl-d7 group, iso-butyl group, sec-butyl group, tert-butyl group, tert-butyl-d9 group, iso-pentyl group, neopentyl group, tert-octyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 3- Fluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, perfluorobutyl group, 5-fluoropentyl group, 6-fluoro Hexyl group, chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, 5-chloropentyl group, 6-chlorohexyl group, bromomethyl group, 2-bromoethyl group , Iodomethyl group, 2-iodoethyl group, hydroxymethyl group, hydroxyethyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylethyl group, 4-fluorocyclohexyl group, norbornyl group And adamantyl group and the like, but are not limited thereto.
次に一般式[1]から[3]で示される化合物についてその代表例を挙げる。ただし、これらの化合物に限定されるものではない。 Next, typical examples of the compounds represented by the general formulas [1] to [3] will be given. However, it is not limited to these compounds.
以下に実施例を挙げて本発明を具体的に説明する。但し、本発明はこれらに限定されるものではない。 The present invention will be specifically described below with reference to examples. However, the present invention is not limited to these.
また、2―ハロゲノ―9H―フルオレン、2,7―ジハロゲノ―9H―フルオレンを非特許文献であるBull.Chem.Soc.Jpn.62(1989)439を参考にして合成した。得られた化合物をDMF中、アルキルハライド、NaOCH3を用いてフルオレンの9位のアルキル化を行った。さらに、得られた2―ハロゲノ―9―ジアルキルフルオレン、2,7―ジハロゲノ―9―ジアルキルフルオレンをボロン酸またはボロン酸ピナコールエステル体の合成を行った。この合成には非特許文献であるORGANIC SYNTYHESES VIA BORANES Volume3を参考にした。 In addition, 2-halogeno-9H-fluorene and 2,7-dihalogeno-9H-fluorene are described in Bull. Chem. Soc. Jpn. 62 (1989) 439 and synthesized. The resulting compound was alkylated at the 9-position of fluorene using an alkyl halide and NaOCH 3 in DMF. Further, boronic acid or boronic acid pinacol ester was synthesized from the obtained 2-halogeno-9-dialkylfluorene and 2,7-dihalogeno-9-dialkylfluorene. For this synthesis, ORGANIC SYNTHEHES VIA BORANES Volume 3, which is a non-patent document, was referred to.
得られたこれらの化合物を鈴木カップリング、ハロゲン化、アルキル化、ボロン酸合成を適宜組み合わせ、下記反応中間体を合成した。 These compounds thus obtained were appropriately combined with Suzuki coupling, halogenation, alkylation, and boronic acid synthesis to synthesize the following reaction intermediates.
鈴木カップリングには、ORGANIC SYNTYHESES VIA BORANES Volume3を参考にした。 For the Suzuki coupling, ORGANIC SYNTYHESES VIA BORANES Volume 3 was used as a reference.
ハロゲン化にはBull.Chem.Soc.Jpn.62(1989)439を参考にした。 For halogenation, Bull. Chem. Soc. Jpn. 62 (1989) 439.
ここで、X、Yはそれぞれ独立に上記の基を表す。nは1乃至4の整数を表す。 Here, X and Y each independently represent the above group. n represents an integer of 1 to 4.
(実施例1) Example 1
化合物1−1、700mg(1.67mmole)、化合物1−2、417mg(1.67mmole)、Pd(PPh3)4 0.05g、トルエン10ml、エタノール5ml、2M−炭酸ナトリウム水溶液10mlを100mlナスフラスコに仕込み、窒素気流下、80℃で8時間攪拌を行った。反応終了後、反応後有機層をトルエンで抽出し無水硫酸ナトリウムで乾燥後、シリカゲルカラム(ヘキサン+トルエン混合展開溶媒)で精製した。得られた結晶を120℃で真空乾燥後、昇華精製を行い例示化合物A−1を732mg(収率:78%)得た。 Compound 1-1, 700 mg (1.67 mmole), Compound 1-2, 417 mg (1.67 mmole), 0.05 g of Pd (PPh3) 4, 10 ml of toluene, 5 ml of ethanol, and 10 ml of 2M sodium carbonate aqueous solution in a 100 ml eggplant flask The mixture was stirred and stirred at 80 ° C. for 8 hours under a nitrogen stream. After completion of the reaction, the organic layer after the reaction was extracted with toluene, dried over anhydrous sodium sulfate, and purified with a silica gel column (hexane + toluene mixed developing solvent). The obtained crystals were vacuum dried at 120 ° C. and purified by sublimation to obtain 732 mg (yield: 78%) of Exemplary Compound A-1.
MALDI−TOF MS(マトリックス支援イオン化−飛行時間型質量分析)によりこの化合物のM+である562.3を確認した。また、イオン化ポテンシャルは5.83eVである。なお、イオン化ポテンシャルの値は、理研機器製AC−1により測定した値とした。 562.3 which is M + of this compound was confirmed by MALDI-TOF MS (matrix-assisted ionization-time-of-flight mass spectrometry). The ionization potential is 5.83 eV. In addition, the value of ionization potential was taken as the value measured by Riken Instruments AC-1.
(実施例2)
本実施例では、素子構成として、図1(b)に示す有機層が3層の素子を使用した。ガラス基板上に100nmのITOをパターニングした。そのITO基板上に、以下の有機層と電極層を10−5Paの真空チャンバー内で抵抗加熱による真空蒸着して連続製膜し、対向する電極面積が3mm2になるようにした。
ホール輸送層(40nm) 化合物2
発光層(50nm) ホスト:例示化合物A−1、ゲスト化合物3 (重量比 5%)
電子輸送層(25nm) 化合物4
金属電極層1(1nm) KF
金属電極層2(100nm) Al
(Example 2)
In this example, an element having three organic layers as shown in FIG. 1B was used as the element structure. 100 nm ITO was patterned on the glass substrate. On the ITO substrate, the following organic layers and electrode layers were continuously formed by vacuum deposition by resistance heating in a vacuum chamber of 10 −5 Pa so that the opposing electrode area was 3 mm 2 .
Hole transport layer (40 nm) Compound 2
Light emitting layer (50 nm) Host: Exemplified compound A-1, guest compound 3 (weight ratio 5%)
Electron transport layer (25 nm) Compound 4
Metal electrode layer 1 (1 nm) KF
Metal electrode layer 2 (100 nm) Al
EL素子の特性は、電流電圧特性をヒューレッドパッカード社製・微小電流計4140Bで測定し、発光輝度は、トプコン社製BM7で測定した。その結果、4.0Vの印加電圧で、発光輝度1170cd/m2、の青色発光が観測された。さらに、窒素雰囲気下で保ち100時間電圧を印加したところ、初期輝度1900cd/m2から100時間後、800cd/m2となり、優れた耐久性の有機発光素子が実現できた。 As for the characteristics of the EL element, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hured Packard, and the light emission luminance was measured with BM7 manufactured by Topcon. As a result, blue light emission with an emission luminance of 1170 cd / m 2 was observed at an applied voltage of 4.0 V. Further, when a voltage was applied for 100 hours kept in a nitrogen atmosphere, 100 hours after the initial luminance 1900cd / m 2, 800cd / m 2 , and the organic light emitting device having excellent durability can be realized.
(実施例3)
(例示化合物B−1の合成)
実施例1の化合物1−2の代わりに化合物1−3を用いる以外は、実施例1と同様の方法で例示化合物B−1を合成した。
MALDI−TOF MS(マトリックス支援イオン化−飛行時間型質量分析)によりこの化合物のM+である562.3を確認した。また、イオン化ポテンシャルは5.85eVである。なお、イオン化ポテンシャルの値は、理研機器製AC−1により測定した値とした。
(Example 3)
(Synthesis of Exemplary Compound B-1)
Exemplified Compound B-1 was synthesized in the same manner as in Example 1 except that Compound 1-3 was used instead of Compound 1-2 in Example 1.
562.3 which is M + of this compound was confirmed by MALDI-TOF MS (matrix-assisted ionization-time-of-flight mass spectrometry). The ionization potential is 5.85 eV. In addition, the value of ionization potential was taken as the value measured by Riken Instruments AC-1.
11 金属電極
12 発光層
13 ホール輸送層
14 透明電極
15 透明基板
16 電子輸送層
17 励起子拡散防止層
DESCRIPTION OF SYMBOLS 11 Metal electrode 12 Light emitting layer 13 Hole transport layer 14 Transparent electrode 15 Transparent substrate 16 Electron transport layer 17 Exciton diffusion prevention layer
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WO2010074087A1 (en) | 2008-12-26 | 2010-07-01 | 出光興産株式会社 | Material for organic electroluminescent element, and organic electroluminescent element |
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