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WO2007063754A1 - 有機電界発光素子用化合物及び有機電界発光素子 - Google Patents

有機電界発光素子用化合物及び有機電界発光素子 Download PDF

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WO2007063754A1
WO2007063754A1 PCT/JP2006/323290 JP2006323290W WO2007063754A1 WO 2007063754 A1 WO2007063754 A1 WO 2007063754A1 JP 2006323290 W JP2006323290 W JP 2006323290W WO 2007063754 A1 WO2007063754 A1 WO 2007063754A1
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ring
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French (fr)
Inventor
Masaki Komori
Toshihiro Yamamoto
Takahiro Kai
Masanori Hotta
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Nippon Steel Chemical and Materials Co Ltd
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Nippon Steel Chemical Co Ltd
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Priority to JP2007547906A priority Critical patent/JP4593631B2/ja
Priority to CN200680045030.8A priority patent/CN101321755B/zh
Priority to US12/085,447 priority patent/US7993760B2/en
Priority to EP06833112A priority patent/EP1956022B1/en
Publication of WO2007063754A1 publication Critical patent/WO2007063754A1/ja
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Definitions

  • the present invention relates to a novel compound for organic electroluminescence device and organic electroluminescence device (hereinafter referred to as organic EL device). Specifically, a phosphorescent dopant and a host compound having a specific structure are used. It is related to an organic EL device that exhibits high brightness when used in combination.
  • an organic EL element has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure.
  • an organic EL element when an electric field is applied between both electrodes, cathode force electrons are injected and anode force holes are injected.
  • These recombination energy levels in the light emitting layer have conduction band strength. Utilizes the phenomenon of emitting light as energy when returning to the valence band.
  • the electrode type is optimized for the purpose of improving the efficiency of the electrode force carrier injection, and consists of a hole transport layer that also has an aromatic diamine force and an 8-hydroxyquinoline aluminum complex (hereinafter referred to as Alq3).
  • Alq3 8-hydroxyquinoline aluminum complex
  • Patent Document 1 JP-T-2003-515897
  • Patent Document 1 Japanese Translation of Special Publication 2003-515897
  • Patent Document 2 JP 2001-313178 A
  • Patent Document 3 JP 2002-305083 A
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-352957
  • Patent Document 5 Japanese Patent Laid-Open No. 11-162650
  • Patent Document 6 Japanese Patent Laid-Open No. 11-176578
  • CBP a powerful rubazole compound introduced in Japanese Patent Application Laid-Open No. 2001-313178
  • Ir (ppy) 3 2,-phenol-lysine iridium complex
  • CBP has a characteristic that it can easily flow holes but not electrons. As a result, the charge injection balance is lost, and excess holes flow out to the electron transport side, resulting in a decrease in light emission efficiency from Ir (ppy) 3.
  • indolocarbazole compounds are disclosed in JP-A-11-162650 and JP-A-11-176578, the compounds of the present invention are not disclosed.
  • the endocarbazole compound disclosed in JP-A-11-162650 and JP-A-11-176578 is recommended for use as a hole transporting material, and the stability of the compound is also improved. It is not taught to use as a phosphorescent host material. Disclosure of the invention
  • An object of the present invention is to provide a practically useful organic EL device having high efficiency and high driving stability, and a compound suitable therefor, in view of the above-described present situation.
  • the compound for organic electroluminescence device of the present invention is represented by the following general formula (1).
  • z is not a condensed ring structure ⁇ -substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group
  • a linking group consisting of
  • n an integer of 2 or more
  • Y represents a group represented by the following formula (la),
  • Ring A represents an aromatic ring or a heterocycle represented by the formula (lb) fused with the adjacent ring
  • Ring B represents a heterocycle represented by the formula (lc) fused with the adjacent ring
  • X represents carbon or nitrogen
  • 43 represents a ring that is condensed with hydrogen, a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group that is not a condensed ring structure, or a ring containing X;
  • 44 is not a condensed ring structure !, represents a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,
  • R and R are hydrogen, alkyl, aralkyl, alkenyl, alkynyl, cyan
  • dialkylamino group dialylamino group, dialalkylamino group, amino group, nitro group
  • R 1 and R 2 have the same meaning as R independently.
  • the compound for organic electroluminescence device of the present invention represented by the general formula (1) includes a compound represented by the following general formula (2) or (3).
  • Ring A and ring A ′ represent an aromatic ring represented by the formula (2a) fused with an adjacent ring
  • ring B and ring B ′ represent a heterocycle represented by the formula (2b) fused with an adjacent ring.
  • Ring C and Ring C ′ represent an aromatic ring represented by the formula (3a) fused with the adjacent ring,
  • Ring D and Ring D ′ represent a heterocyclic ring represented by Formula (3b) that is condensed with an adjacent ring,
  • Ring E and ring E ′ represent a heterocycle represented by the formula (3c) that is condensed with an adjacent ring.
  • the compound for organic electroluminescence device of the present invention includes a compound represented by the following general formula (4) or (5).
  • Ring F and ring F ′ represent a heterocycle represented by the formula (5a) that is condensed with an adjacent ring.
  • rings A, A, C, C are benzene rings Yes, R, R, R, R, R, R, R, R are substituted or unsubstituted
  • X represents carbon or nitrogen
  • R 1, R 2, R 3, R 5 are independently hydrogen, a substituted or unsubstituted fragrance that is not a condensed ring structure
  • R R to R, R to R, R to R, R, R are independently substituted or non-condensed ring structures
  • An unsubstituted aromatic hydrocarbon group or an aromatic heterocyclic group An unsubstituted aromatic hydrocarbon group or an aromatic heterocyclic group
  • Ar to Ar are independently a substituted or unsubstituted aromatic hydrocarbon group that is not a condensed ring structure, or
  • a divalent linking group comprising an aromatic heterocyclic group
  • R to R R to R, R, R to R, R, R to R, R to R, R to R, R to R, R to R, R to R are independently
  • Kill group aralkyl group, alkyl group, alkyl group, cyano group, dialkylamino group
  • the present invention provides an organic electroluminescent device having a light emitting layer between an anode and a cathode laminated on a substrate, wherein the light emitting layer comprises a phosphorescent dopant and the above organic electroluminescence.
  • An organic electroluminescence device comprising an elemental compound as a host material.
  • the organic electroluminescent element preferably has a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer.
  • At least one of the compounds represented by the general formula (1) preferably the compounds represented by the general formulas (2) to (5), is added to at least one of the organic layers in the organic EL device. Use for one.
  • the compound for an organic EL device of the present invention is represented by the general formula (1).
  • Z represents a linking group selected from a substituted or unsubstituted aromatic hydrocarbon group that is not a condensed ring structure and a substituted or unsubstituted aromatic heterocyclic group that is not a condensed ring structure.
  • Show. n represents an integer of 2 or more.
  • Z is an n-valent group.
  • preferred examples of the aromatic hydrocarbon ring forming the aromatic hydrocarbon group include a benzene ring, a biphenyl ring, and a terphenyl ring.
  • the aromatic heterocyclic group include a pyridine ring, a triazole ring, a diazole ring, a phenol pyridine ring, a phenol triazole ring, and a triphenyl triazole ring.
  • substituents include alkyl having 1 to 6 carbon atoms, phenol and pyridyl. The number of substituents is 0 to 4, preferably 0 to 2.
  • Y is a group represented by the above formula (la).
  • formula (la) ring A and ring B represent a ring fused with an adjacent ring.
  • Y is a group represented by the general formula (Id).
  • R 1, R 2 force is a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group.
  • preferred examples of the aromatic hydrocarbon group include a phenyl group and a biphenylyl group.
  • a pyridyl group is preferable.
  • preferred examples of the substituent include alkyl having 1 to 6 carbon atoms, phenyl, pyridyl and the like. The number of substituents is 0 to 4, preferably 0 to 2.
  • R or R ⁇ is an aromatic hydrocarbon group
  • Preferred examples of 43 44 include a phenyl group and a biphenyl-lyl group. When it is an aromatic heterocyclic group, a pyridyl group is preferable. When these have a substituent, preferred examples of the substituent include alkyl having 1 to 6 carbon atoms, phenol, pyridyl and the like. The number of substituents is 0 to 4, preferably 0 to 2. R may be the above aromatic hydrocarbon group or aromatic heterocyclic group.
  • this ring When the ring is fused to a 6-membered ring containing X in the formula (lb), this ring may be a fused ring.
  • the condensed ring include rings E and E ′ and rings F and F ′ having a condensed ring in the general formulas (3) and (5). That is, an indole ring optionally having R, R, R or R
  • the nitrogen-containing ring in the indole ring is condensed to a 6-membered ring containing X.
  • the compound of the general formula (1) when ring A is a benzene ring, it becomes an indolo power rubazole derivative, so that the compound of the present invention is a compound having an indolo power rubazole unit! be able to.
  • This indolo power rubazole unit is a unit that enhances the hole transportability, and n must be 2 or more in order to further enhance the hole transportability.
  • the compound of the general formula (1) includes the compounds represented by the general formulas (2) to (5). Therefore, when the compound of the general formula (1) is referred to, the compounds represented by these formulas It is understood that it includes
  • n is preferably 2-4, more preferably 2-3.
  • n is 5 or more, the molecular weight increases, the sublimation property decreases, and it becomes difficult to use the vapor deposition method when manufacturing the electroluminescent device, or the purification becomes difficult due to the high molecular weight of impurities. There is a case.
  • Examples of the compound represented by the general formulas (2) to (5) include compounds represented by the general formulas (2) to (5).
  • the symbols appearing in the general formulas (2) to (5) and having the same meaning as in the general formula (1) are preferably the same groups or rings as described in the general formula (1).
  • the organic EL device of the present invention has a light emitting layer between an anode and a cathode laminated on a substrate, and the light emitting layer contains a phosphorescent dopant and the compound for organic EL as a host material. To do. It is advantageous to have a hole injection / transport layer between the anode and the light emitting layer and an electron injection / transport layer between the cathode and the light emitting layer. It is also advantageous to have a hole blocking layer between the light emitting layer and the electron injecting and transporting layer.
  • the organic EL device of the present invention is a compound represented by the general formula (1) in the general formula (1) as a host material or represented by the general formulas (2) to (5). It is better to use the compound.
  • the compound represented by the general formula (1) can be easily produced by a known method. For example, it can be produced by the following reaction formula with reference to the synthesis example shown in Tetrahedron, 1991, Vol. 47, No. 37, p7739-7750.
  • the compound represented by the general formula (2) can be produced by the following reaction formula.
  • Ar to Ar in the general formulas (2) to (5) represent a divalent linking group. Specifically, the following Y-1
  • a linking group represented by -Y-118 is mentioned.
  • linking groups may have a substituent.
  • substituents are alkyl, aralkyl, alkyl, alkyl, cyano, dialkylamino, dialkylamino, dialalkylamino, amino, nitro, acyl, alkoxy
  • substituents include a carbo group, a carboxyl group, an alkoxyl group, an alkyl sulfol group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group or an aromatic heterocyclic group.
  • substituents include the following substituents represented by Z-1 to Z-138.
  • the organic EL device of the present invention contains a phosphorescent dopant and the compound for organic EL as a host material in the light emitting layer.
  • the phosphorescent dopant material in the light emitting layer preferably includes an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
  • organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
  • Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2'acac3, and complexes such as PtOEt3. . Specific examples of these complexes are shown below, but are not limited to the following compounds.
  • the amount of the phosphorescent dopant contained in the light emitting layer is preferably in the range of 5 to 10 wt%.
  • the organic EL device of the present invention is an organic EL device having at least one light-emitting layer between an anode and a cathode laminated on a substrate, and the light-emitting layer has a phosphorescent dopant, a general formula Contains the compound represented by (1).
  • FIG. 1 Schematic diagram showing an example of an organic EL device
  • the structure of the organic EL element of the present invention will be described with reference to the drawings.
  • the structure of the organic EL element of the present invention is not limited to the illustrated one.
  • Fig. 1 is a cross-sectional view schematically showing a structural example of a general organic EL device used in the present invention.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is hole transport.
  • 5 represents a light emitting layer
  • 6 represents an electron transport layer
  • 7 represents a cathode.
  • the substrate, the anode, the light emitting layer, and the cathode as the essential layers. It is preferable to have a hole blocking layer between the layer and the electron injecting and transporting layer.
  • the hole injection / transport layer means either or both of the hole injection layer and the hole transport layer
  • the electron injection / transport layer means either or both of the electron injection layer and the electron transport layer. .
  • the structure opposite to that shown in Fig. 1, that is, the cathode 7, the electron transport layer 6, the light emitting layer 5, the hole transport layer 4, and the anode 2 can be laminated on the substrate 1 in this order.
  • the organic EL element of the present invention between two substrates, at least one of which is highly transparent. Also in this case, layers can be added or omitted as necessary.
  • the present invention is applicable even if the organic EL element is a single element, an element having a structure arranged in an array, or a structure in which an anode and a cathode are arranged in a Y matrix. can do.
  • the organic EL device of the present invention by containing a compound having a specific skeleton in the light emitting layer and a phosphorescent light emitting dopant, the organic EL device has higher luminous efficiency and driving than the conventional device using light emission from a singlet state. Devices with greatly improved stability can be obtained and can be used for full-color or multi-color panels! Example
  • the filtrate was transferred to a 2000 ml separatory funnel and separated into an organic layer and an aqueous layer.
  • the organic layer was washed with 500 ml of water three times, and then the obtained organic layer was dehydrated with magnesium sulfate, and after the magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 13.7 g (41.2 mmo 1, yield 40.6%) of a white solid.
  • the filtrate was transferred to a 1000 ml separatory funnel and separated into an organic layer and an aqueous layer.
  • the organic layer was washed three times with 100 ml of water, and then the obtained organic layer was dehydrated with magnesium sulfate. After magnesium sulfate was filtered off once, the solvent was distilled off under reduced pressure. Then, it refine
  • Compound 40 had an EI—MS (M + 1) of 818 and an undetected melting point.
  • the filtrate was transferred to a 2000 ml separatory funnel and separated into an organic layer and an aqueous layer.
  • the organic layer was washed with 500 ml of water three times, and then the obtained organic layer was dehydrated with magnesium sulfate, and after the magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 13.7 g (41.2 mmo 1, yield 40.6%) of a white solid.
  • Compound 27 had an EI-MS (M + 1) of 816 and a melting point of 362 ° C.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • the excitation wavelength the maximum absorption wavelength of Compound 9 was used, and the light emitted at that time was observed and compared with the light emitted in the case of a thin film of Compound 9 alone.
  • the results are shown in Table 1.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • the excitation wavelength the maximum absorption wavelength of Compound 40 was used, and the light emitted at that time was observed and compared with the light emitted in the case of a thin film of Compound 40 alone.
  • the results are shown in Table 1.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • the excitation wavelength the maximum absorption wavelength of Compound 27 was used, and the light emitted at that time was observed and compared with the light emitted in the case of the thin film of Compound 27 alone.
  • the results are shown in Table 1.
  • Example 4 The same procedure as in Example 4 was performed, except that the thin film main component was changed to Alq3 to prepare a thin film.
  • the results are shown in Table 1. From Table 1, when compounds 9, 40, and 27 are used as the main material of the light emitting layer, energy is transferred to Ir (ppy) 3, and when the force Alq3 is used to observe light emission from Ir (ppy) 3, , Ir (ppy) 3 shows no energy transition, Alq3 itself emits fluorescence
  • an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • the compound 9 and Ir (ppy) as a light-emitting layer are shared on the hole transport layer from different evaporation sources.
  • Vapor deposition was performed to form a thickness of 25 nm. At this time, the concentration of Ir (ppy) was 7.0%.
  • Alq3 As the child transport layer, Alq3 was formed to a thickness of 50 nm. Furthermore, lithium fluoride (LiF) was formed as an electron injection layer on the electron transport layer to a thickness of 0.5 °. Finally, aluminum (A1) was formed as an electrode with a thickness of 170 nm on the electron injection layer to produce an organic EL device.
  • LiF lithium fluoride
  • AlA1 aluminum
  • an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • the compound 40 and Ir (ppy) as a light emitting layer are simultaneously coated on the hole transport layer from different vapor deposition sources.
  • Vapor deposition was performed to form a thickness of 25 nm. At this time, the concentration of Ir (ppy) was 7.0%.
  • Alq3 As the child transport layer, Alq3 was formed to a thickness of 50 °. Furthermore, lithium fluoride (LiF) was formed as an electron injection layer on the electron transport layer to a thickness of 0.5 °. Finally, aluminum (A1) was formed as an electrode with a thickness of 170 nm on the electron injection layer to produce an organic EL device.
  • LiF lithium fluoride
  • AlA1 aluminum
  • Example 9 In Figure 1, an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • compound 27 and Ir (ppy) as a light-emitting layer are simultaneously coated on the hole transport layer from different vapor deposition sources.
  • Alq3 As the child transport layer, Alq3 was formed to a thickness of 50 nm. Furthermore, lithium fluoride (LiF) was formed as an electron injection layer on the electron transport layer to a thickness of 0.5 °. Finally, aluminum (A1) was formed as an electrode with a thickness of 170 nm on the electron injection layer to produce an organic EL device.
  • LiF lithium fluoride
  • AlA1 aluminum
  • An organic EL device was prepared in the same manner as in Example 7 except that HMTPD was used as the hole transport layer and TAZ was used as the main component of the light emitting layer.
  • An organic EL device was produced in the same manner as in Example 7 except that TAZ was used as the main component of the light emitting layer.
  • Example 8 2300 6. 0 1 2. 0
  • the filtrate was transferred to a 2000 ml separatory funnel and separated into an organic layer and an aqueous layer.
  • the organic layer was washed three times with 500 ml of water, and then the obtained organic layer was dehydrated with magnesium sulfate. After magnesium sulfate was filtered off once, the solvent was distilled off under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 13.7 g (0.04 mol, yield 4 0.8%) of a white solid.
  • Compound 103 had an EI-MS (M + 1) of 1072, and a melting point of 492 ° C.
  • Compound 103 was deposited from a deposition source on a glass substrate by a vacuum deposition method under a vacuum degree of 4.0 ⁇ 10 ⁇ 4 Pa, and a thin film was formed at a thickness of 50 ° in 1.0 AZ seconds.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • compound 3 and Ir (ppy) 3 were vapor-deposited on a glass substrate by vacuum vapor deposition under the condition of vacuum degree 4.0 X 10-4 Pa, and the concentration of Ir (ppy) 3 was 7.0%
  • a thin film having a thickness of 50 mm was formed in 1.0 AZ seconds.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • the excitation wavelength used was the maximum absorption wavelength of Compound 103, and the light emitted at that time was observed and compared with the light emitted in the case of a thin film of Compound 103 alone.
  • the results are shown in Table 3.
  • Example 11 The same procedure as in Example 11 was performed, except that the thin film main component was changed to Alq3 to prepare a thin film. The results are shown in Table 3.
  • an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • Alq3 was formed to a thickness of 50 nm. Furthermore, on the electron transport layer, lithium fluoride (LiF) was formed to a thickness of 0.5 as an electron injection layer. Finally, aluminum (A1) was formed as an electrode with a thickness of 170 nm on the electron injection layer to produce an organic EL device.
  • An organic EL device was prepared in the same manner as in Example 12 except that HMTPD was used as the hole transport layer and TAZ was used as the main component of the light emitting layer.
  • An organic EL device was prepared in the same manner as in Example 12 except that TAZ was used as the main component of the light emitting layer.
  • the organic EL device of the present invention can emit light with high luminance and high efficiency at a low voltage.
  • the organic EL device according to the present invention is a flat panel display (for example, for OA computers and wall-mounted televisions), an in-vehicle display device, a mobile phone display, and a light source (for example, a copier). It can be applied to light sources, backlight sources for liquid crystal displays and instruments), display panels, and beacon lights, and its technical value is great.

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Description

明 細 書
有機電界発光素子用化合物及び有機電界発光素子
技術分野
[0001] 本発明は新規な有機電界発光素子用化合物及び有機電界発光素子 (以下、有機 EL素子という）に関するものであり、詳しくは、燐光発光ドーパントと特定の構造を有 するホストイ匕合物を併用することにより、高輝度を示す有機 EL素子に関するものであ る。
背景技術
[0002] 一般に、有機 EL素子は、その最も簡単な構造としては発光層及び該層を挟んだ一 対の対向電極から構成されている。すなわち、有機 EL素子では、両電極間に電界 が印加されると、陰極力 電子が注入され、陽極力 正孔が注入され、これらが発光 層にお ヽて再結合エネルギー準位が伝導帯力 価電子帯に戻る際にエネルギーと して光を放出する現象を利用する。
[0003] 近年、有機薄膜を用いた EL素子の開発が行われるようになった。特に発光効率を 高めるため、電極力 キャリアー注入の効率向上を目的として電極の種類の最適化 を行い、芳香族ジァミン力もなる正孔輸送層と 8—ヒドロキシキノリンアルミニウム錯体 (以下、 Alq3という）からなる発光層とを電極間に薄膜として設けた素子の開発により、 従来のアントラセン等の単結晶を用いた素子と比較して大幅な発光効率の改善がな されたこと力ゝら、自発光 ·高速応答性と ヽつたと特徴を持つ高性能フラットパネルへの 実用を目指して進められてきた。
[0004] また、素子の発光効率を上げる試みとして、蛍光ではなく燐光を用いることも検討さ れて 、る。上記の芳香族ジァミンからなる正孔輸送層と Alq3力 なる発光層とを設け た素子をはじめとした多くの素子が蛍光発光を利用したものであつたが、燐光発光を 用いる、すなわち、三重項励起状態からの発光を利用すれば、従来の蛍光 (一重項) を用いた素子と比べて、 3倍程度の効率向上が期待される。この目的のためにタマリ ン誘導体やべンゾフ ノン誘導体を発光層とすることが検討されてきたが、極めて低 い輝度し力得られな力 た。その後、三重項状態を利用する試みとして、ユーロピウ ム錯体を用いることが検討されてきたが、これも高効率の発光には至らな力つた。燐 光発光ドーパントとしては、特表 2003-515897号公報 (特許文献 1)に挙げられるよう な発明が多数行われて 、る。
[0005] 特許文献 1：特表 2003-515897号公報
特許文献 2：特開 2001-313178号公報
特許文献 3：特開 2002-305083号公報
特許文献 4：特開 2002-352957号公報
特許文献 5：特開平 11-162650号公報
特許文献 6：特開平 11-176578号公報
[0006] 有機 EL素子開発にぉ 、て発光層に用いるホスト材料として提案されて 、るのは、 特開 2001-313178号公報で紹介されている力ルバゾール化合物の CBPである。緑色 燐光発光材料のトリス (2-フエ-ルビリジン)イリジウム錯体 (以下、 Ir(ppy)3と 、う）のホ スト材として CBPを用いると、 CBPは正孔を流し易く電子を流しにくい特性上、電荷注 入バランスが崩れ、過剰の正孔は電子輸送側に流出し、結果として Ir(ppy)3からの発 光効率が低下する。
[0007] 上記の解決手段として、例えば特開 2002-305083号公報のように、発光層と電子輸 送層の間に正孔阻止層を設ける手段がある。この正孔阻止層により正孔を発光層中 に効率よく蓄積することによって、発光層中での電子との再結合確率を向上させ、発 光の高効率ィ匕を達成することができる。現状一般的に用いられている正孔阻止材料 として、 2,9-ジメチル- 4,7-ジフエ-ル- 1, 10-フエナント口リン（以下、 BCPという）及び p -フエ-ルフエノラート-ビス (2-メチル -8-キノリノラート- N1, 08)アルミニウム（以下、 BA1 qという）が挙げられる。これにより電子輸送層で電子と正孔の再結合が起こることを防 止できるが、 BCPは室温でも結晶化し易く材料としての信頼性に欠けるため、素子寿 命が極端に短い。また BAlqは Tgが約 100°Cと比較的良好な素子寿命結果が報告さ れているが、正孔阻止能力が十分でなぐ Ir(ppy)3からの発光効率は低下する。
[0008] 一方、特開 2002-352957号公報で紹介されている 3-フエニル -4-(1'-ナフチル) -5- フエ-ル- 1,2,4-トリァゾール（以下、 TAZという）も燐光有機 EL素子のホスト材として 提案されているが、電子を流しやすく正孔を流しにくい特性上、発光領域が正孔輸 送層側となる。従って正孔輸送層の材料によっては Ir(ppy)3との相性問題により、 Ir(p py)3からの発光効率が低下することも考えられる。例えば、正孔輸送層として高性能 、高信頼性、高寿命の点から最も良く使用されている 4,4'-ビス (N-(l-ナフチル) -N-フ ェ-ルァミノ)ビフエ-ル（以下、 NPBという）は、 Ir(ppy)3との相性が悪ぐ Ir(ppy)3から N PBにエネルギー遷移が起き、発光効率が低下するという問題がある。
[0009] また、特開平 11-162650号公報及び特開平 11-176578号公報でインドロカルバゾー ル化合物の開示がなされているが、本発明の化合物に関しては、開示されていない 。また、特開平 11-162650号公報及び特開平 11-176578号公報で開示されているィ ンドロカルバゾールイ匕合物は、正孔輸送材料としての使用が推奨されており、化合物 の安定性も謳われている力 燐光ホスト材料としての使用を教えるものではない。 発明の開示
発明が解決しょうとする課題
[0010] 有機 EL素子をフラットパネル ·ディスプレイ等の表示素子に応用するためには、素 子の発光効率を改善すると同時に駆動時の安定性を十分に確保する必要がある。 本発明は、上記現状に鑑み、高効率かつ高い駆動安定性を有した実用上有用な有 機 EL素子及びそれに適する化合物を提供することを目的とする。
課題を解決するための手段
[0011] 本発明者らは、鋭意検討した結果、特定のインドロ力ルバゾール骨格を有する化合 物を有機 EL素子に使用することで、上記課題を解決することができることを見出し、 本発明を完成するに至った。
[0012] 本発明の有機電界発光素子用化合物は、下記一般式（1)で表わされる。
z -ev ) n
( 1 )
ここで、
zは縮環構造でな ヽ置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基 からなる連結基を示し、
nは 2以上の整数を示し、
Yは下記式（la)で表わされる基を示す、
Figure imgf000006_0001
ここで、
環 Aは隣接環と縮合する式（lb)で表わされる芳香族環又は複素環を示し、 環 Bは隣接環と縮合する式（lc)で表わされる複素環を示し、
Xは炭素又は窒素を示し、
R
43は、水素、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族 複素環基、又は Xを含む環と縮合する環を示し、
R
44は縮環構造でな!、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環 基を示し、
R 、 R は、水素、アルキル基、ァラルキル基、アルケニル基、アルキニル基、シァノ
41 42
基、ジアルキルアミノ基、ジァリールアミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基 、ァシル基、アルコキシカルボ-ル基、カルボキシル基、アルコキシル基、アルキルス ルホニル基、ハロアルキル基、水酸基、アミド基、置換又は未置換の芳香族炭化水 素基又は芳香族複素環基を示す。
[0013] 一般式（1)において、 Yが下記式（Id)を表わされる基であると優れた有機電界発 光素子用化合物を与える。あるいは、 nが 2、 3又は 4であると優れた有機電界発光素 子用化合物を与える。
Figure imgf000007_0001
ここで、
R
45は、水素、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族 複素環基を示し、
R
46は R
44と同じ意味を有し、
R 、R は独立に、 R と同じ意味を有する。
47 48 41
[0015] また、一般式（1)で表わされる本発明の有機電界発光素子用化合物には、下記一 般式（2)又は（3)で表される化合物がある。
Figure imgf000008_0001
Figure imgf000008_0002
ここで、
環 A、環 A'は隣接環と縮合する式 (2a)で表される芳香環を示し、 環 B、環 B'は隣接環と縮合する式 (2b)で表される複素環を示す。
Figure imgf000009_0001
Figure imgf000009_0002
N-R14
( 3 b) N - R15
( 3 c)
ここで、
環 C、環 C'は隣接環と縮合する式（3a)で表される芳香環を示し、
環 D、環 D'は隣接環と縮合する式（3b)表される複素環を示し、
環 E、環 E'は隣接環と縮合する式 (3c)で表される複素環を示す。
更に、本発明の有機電界発光素子用化合物には、下記一般式 (4)又は (5)で表さ れる化合物がある。
Figure imgf000010_0001
Figure imgf000010_0002
Figure imgf000010_0003
ここで、
環 F、環 F'は隣接環と縮合する式 (5a)で表される複素環を示す。
[0019] 上記一般式（2)〜（5)及び式（2a)〜（2c)、（3a)〜（3c)、 (5a)中、環 A、 A，、 C、 C ，がベンゼン環であり、 R、R 、R 、R 、R 、R 、R 、R が置換若しくは未置換の
6 14 15 22 23 30 31 32
フエ-ル基又はピリジル基であり、且つ、 R〜R、R〜R 、R 〜R 、R 〜R 力 S、水
1 4 7 12 16 21 24 29 素又はフ -ル基であると優れた有機電界発光素子用化合物を与える。 [0020] 上記一般式（1)〜（5)及び式（la)〜（： Ld)、 (2a)〜（2c)、（3a)〜（3c)、 (5a)にお いて、記号は次の意味を有する。
Xは炭素又は窒素を示し、
R R 、R 、R 、R は独立に、水素、縮環構造でない置換若しくは未置換の芳香
5、 13 17 20 45
族炭化水素基又は芳香族複素環基を示し、
R R 〜R 、R 〜R 、R 〜R 、R 、R は独立に、縮環構造でない置換若しくは
6、 14 15 22 23 30 32 44 46
未置換の芳香族炭化水素基又は芳香族複素環基を示し、
Ar〜Arは独立に、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は
1 4
芳香族複素環基からなる 2価の連結基を示し、
R〜R R〜R 、R 、R 〜R 、R 、 R 〜R 、 R 〜R 、 R 〜R は独立に、ァノレ
1 4、 7 12 16 18 19 21 24 29 41 42 47 48
キル基、ァラルキル基、ァルケ-ル基、アルキ-ル基、シァノ基、ジアルキルアミノ基
、ジァリールアミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基、ァシル基、アルコキシ カルボ-ル基、カルボキシル基、アルコキシル基、アルキルスルホ-ル基、ハロアル キル基、水酸基、アミド基、置換又は未置換の芳香族炭化水素基又は芳香族複素環 基を示す。
[0021] また、本発明は、基板上に積層された陽極と陰極の間に、発光層を有する有機電 界発光素子であって、該発光層が、燐光発光性ドーパントと上記の有機電界発光素 子用化合物をホスト材料として含有することを特徴とする有機電界発光素子である。 この有機電界発光素子は、陽極と発光層の間に正孔注入輸送層及び陰極と発光層 の間に電子注入輸送層を有することが望ましい。あるいは、発光層と電子注入輸送 層の間に正孔阻止層を有してなることが望ましい。
[0022] 本発明では前記一般式（1)で表わされる化合物、好ましくは一般式 (2)〜（5)で表 わされる化合物のいずれか 1以上を有機 EL素子中の有機層の少なくとも 1つに用い る。
[0023] 本発明の有機 EL素子用化合物は、上記一般式（1)で表される。一般式（1)中、 Z は、縮環構造でな!ヽ置換若しくは未置換の芳香族炭化水素基及び縮環構造でな 、 置換若しくは未置換の芳香族複素環基から選ばれる連結基を示す。 nは 2以上の整 数を示す。そして、 Zは n価の基である。 [0024] 連結基 Zが芳香族炭化水素基である場合、芳香族炭化水素基を形成する芳香族 炭化水素環としては、ベンゼン環、ビフヱ-ル環、ターフェニル環等が好ましく挙げら れる。芳香族複素環基である場合、ピリジン環、トリァゾール環、ジァゾール環、フエ -ルピリジン環、フエ-ルトリアゾール環、トリフエ-ルトリアゾール環等が好ましく挙げ られる。これらが置換基を有する場合、置換基としては炭素数 1〜6のアルキル、フエ -ル、ピリジル等が好ましく挙げられる。置換基の数は 0〜4、好ましくは 0〜2がよい。
[0025] Yは上記式（la)で表わされる基である。式（la)中、環 A及び環 Bは隣接環と縮合 する環を表す。有利には、 Yは上記一般式（Id)で表わされる基である。
[0026] R 、R 力 置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基である
41 42
場合、芳香族炭化水素基としては、フヱニル基、ビフヱ-リル基等が好ましく挙げられ る。芳香族複素環基である場合、ピリジル基が好ましく挙げられる。これらが置換基を 有する場合、置換基としては炭素数 1〜6のアルキル、フ ニル、ピリジル等が好まし く挙げられる。置換基の数は 0〜4、好ましくは 0〜2がよい。
[0027] R 又は R ί 芳香族炭化水素基である場合、芳香族炭化水素基として
43 44 は、フエ二 ル基、ビフヱ-リル基等が好ましく挙げられる。芳香族複素環基である場合、ピリジル 基が好ましく挙げられる。これらが置換基を有する場合、置換基としては炭素数 1〜6 のアルキル、フエ-ル、ピリジル等が好ましく挙げられる。置換基の数は 0〜4、好まし くは 0〜2がよい。 R は、上記芳香族炭化水素基又は芳香族複素環基であることが
43
できる他、水素又は式（lb)中の Xを含む 6員環に縮合する環であることができ、水素 又は上記環であることが好まし 、。
式（lb)中の Xを含む 6員環に縮合する環である場合、この環は縮合環であってもよ い。縮合環である場合の例としては、一般式（3)及び（5)中の縮合環を有する環 E、 E'及び環 F、 F'がある。すなわち、 R、 R 、 R 又は R を有してもよいインドール環
9 12 25 28
が好ましい。この場合、インドール環中の含窒素環が Xを含む 6員環に縮合する。
[0028] 一般式（1)にお 、て、環 Aがベンゼン環である場合は、インドロ力ルバゾール誘導 体となるので、本発明の化合物はインドロ力ルバゾールユニットを有する化合物と!/、う ことができる。このインドロ力ルバゾールユニットはホール輸送性を高めるユニットであ り、ホール輸送性をより高めるために、 nは 2以上であることが必要である。なお、一般 式（1)は、一般式（1)の化合物は、一般式（2)〜（5)で表わされる化合物を含むので 、一般式（1)の化合物というときは、これらの式で表わされる化合物を含む意味と解さ れる。
[0029] nは 2〜4であることが好ましぐ 2〜3であることがより好ましい。 nが 5以上の場合で は分子量が大きくなり、昇華性が低下して、電界発光素子を製作する際に蒸着法を 用いる場合に支障が出る又は不純物の高分子量ィ匕により精製が困難となる場合があ る。
[0030] nが 2であり、一般式（1)に含まれる化合物としては、一般式（2)〜（5)表わされる化 合物がある。一般式 (2)〜（5)に現れる記号で、一般式（1)と同じ意味を有する記号 は、一般式（1)で述べたと同様な基又は環が好ましい。
[0031] 本発明の有機 EL素子は、基板上に積層された陽極と陰極の間に、発光層を有し、 該発光層が、燐光発光性ドーパントと上記有機 EL用化合物をホスト材料として含有 する。有利には、陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電 子注入輸送層を有することがよい。また、発光層と電子注入輸送層の間に正孔阻止 層を有することも有利である。
[0032] 更に有利には、本発明の有機 EL素子は、ホスト材料として前記一般式（1)中、 Yが 一般式（Id)で表わされる化合物又一般式（2)〜（5)で表される化合物を用いること がよい。
[0033] 一般式（1)で表される化合物は公知の方法で容易に製造することができる。例えば 、 Tetrahedron,1991,Vol.47,No.37,p7739-7750に示される合成例を参考にして以下 の反応式により製造することができる。
[0034] 一般式（2)で表される化合物は、以下の反応式により製造することができる。
Figure imgf000014_0001
[0036] また、一般式（1)中、 Yが一般式（Id)で、 n=3の化合物は、以下の反応式により製 造することができる。
Figure imgf000015_0001
Figure imgf000015_0002
Figure imgf000015_0003
[0038] 一般式（2)〜（5)中の Ar〜Arは 2価の連結基を表す。具体的には、以下の Y— 1
1 4
〜Y— 118で表される連結基が挙げられる。
[0039] また、これらの連結基は置換基を有しても良い。置換基の例としてはアルキル基、 ァラルキル基、ァルケ-ル基、アルキ-ル基、シァノ基、ジアルキルアミノ基、ジァリー ルァミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基、ァシル基、アルコキシカルボ- ル基、カルボキシル基、アルコキシル基、アルキルスルホ-ル基、ハロアルキル基、 水酸基、アミド基、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基が 挙げられる。
Figure imgf000016_0001
ss-人 人 ss-人 ZZ - k
Figure imgf000016_0002
[0濯] 6 / 900Zdf/ェ:) d f>LZ90IL00Z OAV
Figure imgf000017_0001
Figure imgf000017_0002
/ 900Zdf/ェ:) d 91- SL£90/L00Z OAV [0042]
Figure imgf000018_0001
[0043] 置換基の好ましい例として、以下の Z— 1〜Z— 138で表される置換基が挙げられる
Figure imgf000019_0001
[^00] / 900Zdf/ェ:) d LY 17S.C90/.00Z OAV
Figure imgf000020_0001
0045
Figure imgf000021_0001
/ 900Zdf/ェ:) d 61· SL£90/L00Z OAV
Figure imgf000022_0001
前記一般式（2)〜（5)で表される化合物の好ま ヽ具体例を以下に示すが、これら に限定するものではない。
Figure imgf000023_0001
[6濯]Z£Z£/900Zd£/lDd YZ t^L£90/L00Z OAV
Figure imgf000024_0001
s00
Figure imgf000025_0001
[0052]
Figure imgf000026_0001
Figure imgf000026_0002
49 50 51
Figure imgf000027_0001
53
52 54
Figure imgf000027_0002
Figure imgf000027_0003
61 62 63
前記一般式（1)で表され、 Yが一般式（Id)であり、 nが 3以上の有機 EL素子用ィ匕 合物の好ましい具体例を以下に示す力 これらに限定するものではない。
Figure imgf000028_0001
[0056]
Figure imgf000029_0001
Figure imgf000030_0001
[0058]
Figure imgf000031_0001
Figure imgf000031_0002
Figure imgf000031_0003
Figure imgf000032_0001
[0060] 本発明の有機 EL素子は、発光層中に燐光発光性ドーパントと上記有機 EL用化合 物をホスト材料として含有する。発光層における燐光発光ドーパント材料としては、ル テ-ゥム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から 選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。かかる 有機金属錯体は、前記特許文献等で公知であり、これらが選択されて使用可能であ る。
[0061] 好ましい燐光発光ドーパントとしては、 Ir等の貴金属元素を中心金属として有する Ir (ppy)3等の錯体類、 Ir(bt)2 'acac3等の錯体類、 PtOEt3等の錯体類が挙げられる。こ れらの錯体類の具体例を以下に示すが、下記の化合物に限定されない。
Figure imgf000033_0001
Figure imgf000033_0002
Figure imgf000034_0001
[0065] 前記燐光発光ドーパントが発光層中に含有される量は、 5〜 10重量％の範囲にあ ることが好ましい。
[0066] 本発明の有機 EL素子は、基板上に積層された陽極と陰極の間に、少なくとも 1つ の発光層を有する有機 EL素子であり、該発光層が燐光発光性ドーパントと、一般式 ( 1)で表わされる化合物を含有する。
図面の簡単な説明
[0067] [図 1]有機 EL素子の一例を示した模式図
符号の説明
[0068] 1 基板 2 陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 電子輸送層
7 陰極
発明を実施するための最良の形態
[0069] 次に、本発明の有機 EL素子の構造について、図面を参照しながら説明するが、本 発明の有機 EL素子の構造は何ら図示のものに限定されるものではない。
[0070] 図 1は本発明に用いられる一般的な有機 EL素子の構造例を模式的に示す断面図 であり、 1は基板、 2は陽極、 3は正孔注入層、 4は正孔輸送層、 5は発光層、 6は電 子輸送層、 7は陰極を各々表わす。本発明の有機 EL素子では、基板、陽極、発光 層及び陰極を必須の層として有する力 必須の層以外の層以外に、正孔注入輸送 層、電子注入輸送層を有することがよぐ更に発光層と電子注入輸送層の間に正孔 阻止層を有することがよい。なお、正孔注入輸送層は、正孔注入層と正孔輸送層の いずれか又は両者を意味し、電子注入輸送層は、電子注入層と電子輸送層のいず れか又は両者を意味する。
[0071] なお、図 1とは逆の構造、すなわち、基板 1上に陰極 7、電子輸送層 6、発光層 5、 正孔輸送層 4、陽極 2の順に積層することも可能であり、既述したように少なくとも一 方が透明性の高い 2枚の基板の間に本発明の有機 EL素子を設けることも可能であ る。この場合も、必要により層を追加したり、省略したりすることが可能である。
[0072] 本発明は、有機 EL素子が、単一の素子、アレイ状に配置された構造からなる素子 、陽極と陰極力 一 Yマトリックス状に配置された構造の 、ずれにぉ 、ても適用するこ とができる。本発明の有機 EL素子によれば、発光層に特定の骨格を有する化合物と 、燐光発光ドーパントを含有させることにより、従来の一重項状態からの発光を用い た素子よりも発光効率が高くかつ駆動安定性においても大きく改善された素子が得 られ、フルカラーあるいはマルチカラーのパネルへの応用にお!/、て優れた性能を発 揮できる。 実施例
[0073] 以下、本発明を実施例によって更に詳しく説明するが、本発明はこれらの実施例に 限定されるものではなぐ種々の形態で実施することが可能である。なお、化合物番 号は上記化学式に付した番号である。
[0074] 実施例 1
(化合物 9の合成）
脱気窒素置換した 200ml三口フラスコに 1,2-シクロへキサンジオン 5.0g(44.59mmol) 、フエ-ルヒドラジン塩酸塩 12.9g (89.21mmol)をカ卩え、これにエタノール 145mlをカロえ て攪拌させた。その後、同フラスコ内に濃硫酸 0.45g (4.59mmol)を 5分間かけ滴下し た。その後 65°Cまで加熱し、 4時間攪拌した。室温まで冷却した後、生じた紫茶色結 晶を濾取した後、濾取した結晶をエタノール 50mlで二回、リスラリー洗浄をおこなった 。これを、減圧乾燥して紫茶色粉末 12.0g (43.59mmol、収率 97.7%)を得た。
次に、 300ml三口フラスコに上記紫茶色粉末 12.0g (43.59mmol)をカ卩え、これに酢酸 140g、トリフルォロ酢酸 8.0gを加えて攪拌させた。その後 100°Cまで加熱し、 15時間攪 拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸 20 0mlでリンス洗浄をおこなった後、へキサン 200mlでリンス洗浄をおこなった。これを、 減圧乾燥して白色粉末 5.0g (19.51mmol、収率 44.4%)を得た。
[0075] 脱気窒素置換した 200ml三口フラスコに上記で得た白色粉末 4.0g (15.61mmol)、 4, 4， -ジョードビフエ-ル 3.2g (7.88mmol)、よう化銅 7.6g (39.91mmol)、炭酸カリウム 9.7 g (70.18mmol)、これにキノリン 150mlをカ卩えて攪拌させた。その後 190°Cまで加熱し、 2 4時間攪拌した。ー且、室温まで冷却した後、ョードベンゼン 40.0g (196.07mmol)、よ う化銅 7.6g (39.91mmol)加え、 190°Cまで加熱し、 3日間攪拌した。室温まで冷却した 後、水 200ml、ジクロロメタン 200mlを加え、攪拌を行った後、生じた黄色結晶を濾取し た。濾液を 1000ml分液ロートへ移し、有機層と水層に分画した。有機層を 200mlの水 で三回洗浄し、その後、得られた有機層を硫酸マグネシウムで脱水を行い、ー且、硫 酸マグネシウムを濾別した後、溶媒を減圧留去した。その後、カラムクロマトグラフィー で精製して白色固体 (化合物 9) 3.0g (3.69mmol、収率 46.8%)を得た。
化合物 9の EI— MS (M+ 1)は 814、融点は 398°Cであった。 [0076] 実施例 2
(化合物 40の合成）
脱気窒素置換した 2000ml三口フラスコに 1,2-シクロへキサンジオン 33.3g(297.0mm ol)、フエ-ルヒドラジン塩酸塩 86.0g (594.7mmol)をカ卩え、これにエタノール 1000mlを 加えて攪拌させた。その後、同フラスコ内に濃硫酸 3.0g (30.6mmol)を 5分間かけ滴下 した。その後 65°Cまで加熱し、 4時間攪拌した。室温まで冷却した後、生じた紫茶色 結晶を濾取した後、濾取した結晶をエタノール 500mlで二回、リスラリー洗浄をおこな つた。これを、減圧乾燥して紫茶色粉末 80.0g (280.5mmol、収率 96.3%)を得た。 次に、 1000ml三口フラスコに上記紫茶色粉末 72.0g (261.5mmol)をカ卩え、これに酢 酸 720g、トリフルォロ酢酸 72.0gを加えて攪拌させた。その後 100°Cまで加熱し、 15時 間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢 酸 200mlでリンス洗浄をおこなった後、へキサン 200mlでリンス洗浄をおこなった。これ を、減圧乾燥して白色粉末 30.0g (117.1mmol、収率 44.8%)を得た。
[0077] 次に、脱気窒素置換した 1000ml三口フラスコに上記で得た白色粉末 26.0g (101.4m mol)、ョードベンゼン 122.7g (601.4mmol)、よう化銅 54.7g (287.2mmol)、炭酸カリウム 66.7g (482.6mmol)、これにキノリン 800mlをカ卩えて攪拌させた。その後 190°Cまで加熱 し、 72時間攪拌した。ー且、室温まで冷却した後、水 500ml、ジクロロメタン 500mlを加 え、攪拌を行った後、生じた黄色結晶を濾取した。濾液を 2000ml分液ロートへ移し、 有機層と水層に分画した。有機層を 500mlの水で三回洗浄し、その後、得られた有機 層を硫酸マグネシウムで脱水を行い、ー且、硫酸マグネシウムを濾別した後、溶媒を 減圧留去した。その後、カラムクロマトグラフィーで精製して白色固体 13.7g (41.2mmo 1、収率 40.6%)を得た。
次に、脱気窒素置換した 500ml三口フラスコに 55%水素化ナトリウム 2.16g (49.5mmol )、脱水 Ν,Ν，-ジメチルホルムアミド 70mlを加え、窒素気流中下で攪拌を行う。上記 で得た白色粉末 13.7g (41.2mmol)に脱水 Ν,Ν，-ジメチルホルムアミド 70mlをカ卩え、溶 解させ、その後、同フラスコ内に 15分間かけ滴下した。滴下終了後、 1時間攪拌を継 続した。その後、塩化シァヌル 3.76g (20.4mmol)に脱水 Ν,Ν，-ジメチルホルムアミド 7 0mlを加え、溶解させ、その後、同フラスコ内に 15分間かけ滴下した。滴下終了後、 2 時間攪拌を継続した後、水 350gを加え、析出した結晶を濾取した。濾取した結晶を 水 300gで二回リスラリーを行い、その後、メタノール 300gにてリスラリーを行った。これ を減圧乾燥した後、カラムクロマトグラフィーで精製して白色粉末 10.9g (14.0mmol、 収率 70.0%)を得た。
[0078] 次に 300ml三口フラスコに上記で得た白色粉末 10.0g (12.9mmol)、フエ-ルボロン 酸 2.0g (16.4mmol)、テトラキス（トリフエ-ルホスフィン）パラジウム（0) 1.5g (1.3mmol) エタノール 50ml、トルエン 100mlをカ卩えて攪拌させた。その後、炭酸ナトリウム 6.5g(47. Ommol)を水 50mlに溶解させ、同フラスコ内にカ卩ぇ 85°Cまで加熱し、 5時間攪拌した。 ー且、室温まで冷却した後、水 100ml、トルエン 100mlをカ卩え、攪拌を行った後、ー且 、不溶物を濾別した。濾液を 1000ml分液ロートへ移し、有機層と水層に分画した。有 機層を 100mlの水で三回洗浄し、その後、得られた有機層を硫酸マグネシウムで脱水 を行い、一旦、硫酸マグネシウムを濾別した後、溶媒を減圧留去した。その後、カラム クロマトグラフィーで精製して黄色固体 5.3g (6.5mmol、収率 50.2%)を得た。
化合物 40の EI— MS (M+ 1)は 818、融点は未検出であった。
[0079] 実施例 3
(化合物 27の合成）
脱気窒素置換した 2000ml三口フラスコに 1,2-シクロへキサンジオン 33.3g(297.0mm ol)、フエ-ルヒドラジン塩酸塩 86.0g (594.7mmol)をカ卩え、これにエタノール 1000mlを 加えて攪拌させた。その後、同フラスコ内に濃硫酸 3.0g (30.6mmol)を 5分間かけ滴下 した。その後 65°Cまで加熱し、 4時間攪拌した。室温まで冷却した後、生じた紫茶色 結晶を濾取した後、濾取した結晶をエタノール 500mlで二回、リスラリー洗浄をおこな つた。これを、減圧乾燥して紫茶色粉末 80.0g (280.5mmol、収率 96.3%)を得た。 次に、 1000ml三口フラスコに上記紫茶色粉末 72.0g (261.5mmol)をカ卩え、これに酢 酸 720g、トリフルォロ酢酸 72.0gを加えて攪拌させた。その後 100°Cまで加熱し、 15時 間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢 酸 200mlでリンス洗浄をおこなった後、へキサン 200mlでリンス洗浄をおこなった。これ を、減圧乾燥して白色粉末 30.0g (117.1mmol、収率 44.8%)を得た。
[0080] 次に、脱気窒素置換した 1000ml三口フラスコに上記で得た白色粉末 26.0g (101.4m mol)、ョードベンゼン 122.7g (601.4mmol)、よう化銅 54.7g (287.2mmol)、炭酸カリウム 66.7g (482.6mmol)、これにキノリン 800mlをカ卩えて攪拌させた。その後 190°Cまで加熱 し、 72時間攪拌した。ー且、室温まで冷却した後、水 500ml、ジクロロメタン 500mlを加 え、攪拌を行った後、生じた黄色結晶を濾取した。濾液を 2000ml分液ロートへ移し、 有機層と水層に分画した。有機層を 500mlの水で三回洗浄し、その後、得られた有機 層を硫酸マグネシウムで脱水を行い、ー且、硫酸マグネシウムを濾別した後、溶媒を 減圧留去した。その後、カラムクロマトグラフィーで精製して白色固体 13.7g (41.2mmo 1、収率 40.6%)を得た。
次に、脱気窒素置換した 2000ml三口フラスコに上記で得た白色粉末 13.7g (41.2mm ol)、 6,6，-ジブロモ- 2,2，-ビビリジル 6.4g(20.4mmol)、よう化銅 1.14g (5.98mmol)、リン 酸三カリウム 25.22g(118.8mmol)これに 1,4-ジォキサン 200mlを加えて攪拌させた。攪 拌を継続しながら tranc- 1,2-シクロへキサンジァミン 10mlをカ卩えた。その後 115°Cまで 加熱し、 15時間攪拌した。一旦、室温まで冷却した後、不溶物を濾取した。濾液を減 圧留去した後、メタノールを加え、析出した白色固体を濾取した。その後、カラムクロ マトグラフィ一で精製して白色固体 5.0g (6.14mmol、収率 30.0%)を得た。
化合物 27の EI— MS (M+ 1)は 816、融点は 362°Cであった。
[0081] 実施例 4
ガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4Paの条件にて化合物 9を蒸着源 から蒸着し、薄膜を 1.0AZ秒にて 50應の厚さで形成した。作成した薄膜を、蛍光測 定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4 Paの条件にて化合物 9と Ir (ppy)3とを異なる蒸着源力も蒸着し、 Ir(ppy)3の濃度が 7.0 %であるような薄膜を Ι.θΑ /秒にて 50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物 9の極大吸収波 長を使用し、そのときに出てくる光を観察し、化合物 9単独の薄膜の場合に出てくる 光と比較した。結果を表 1に示す。
[0082] 実施例 5
ガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4Paの条件にて化合物 40を蒸着 源から蒸着し、薄膜を 1.0AZ秒にて 50應の厚さで形成した。作成した薄膜を、蛍光 測定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4 Paの条件にて化合物 40と Ir(ppy)3とを異なる蒸着源力も蒸着し、 Ir(ppy)3の濃度が 7.0 %であるような薄膜を 1.0 AZ秒にて 50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物 40の極大吸収 波長を使用し、そのときに出てくる光を観察し、化合物 40単独の薄膜の場合に出てく る光と比較した。結果を表 1に示す。
[0083] 実施例 6
ガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4Paの条件にて化合物 27を蒸着 源から蒸着し、薄膜を 1.0AZ秒にて 50應の厚さで形成した。作成した薄膜を、蛍光 測定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4 Paの条件にて化合物 27と Ir(ppy)3とを異なる蒸着源力も蒸着し、 Ir(ppy)3の濃度が 7.0 %であるような薄膜を 1.0 AZ秒にて 50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物 27の極大吸収 波長を使用し、そのときに出てくる光を観察し、化合物 27単独の薄膜の場合に出てく る光と比較した。結果を表 1に示す。
[0084] 比較例 1
薄膜主成分を Alq3に変えて薄膜を作成した以外は、実施例 4と同様に行った。結 果を表 1に示す。表 1から発光層の主たる材料に化合物 9、 40及び 27を用いた場合 、 Ir(ppy)3にエネルギーが遷移し、 Ir(ppy) 3からの発光が観察される力 Alq3を用い た場合は、 Ir(ppy)3にエネルギーが遷移せず、 Alq3自身が蛍光を発することがわかる
[0085] [表 1] ホス 卜からの発光 ドーパン 卜からの発光
実施例 4 X 〇 実施例 5 X 〇 実施例 6 X 〇 比較例 1 〇 X I
[0086] 実施例 7
図 1において、正孔注入層を省略し、電子注入層を追加した構成の有機 EL素子を 作成した。膜厚 150醒の ITOからなる陽極が形成されたガラス基板上に、各薄膜を真 空蒸着法にて、真空度 4.0 X 10— 4 Paで積層させた。まず、 ITO上に正孔輸送層として NPBを 60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物 9と Ir(ppy)とを異なる蒸着源から、共
3
蒸着し、 25nmの厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 %であった。次に、電
3
子輸送層として Alq3を 50nmの厚さに形成した。更に、電子輸送層上に、電子注入層 としてフッ化リチウム (LiF)を 0.5應の厚さに形成した。最後に、電子注入層上に、電 極としてアルミニウム (A1)を 170nmの厚さに形成し、有機 EL素子を作成した。
[0087] 実施例 8
図 1において、正孔注入層を省略し、電子注入層を追加した構成の有機 EL素子を 作成した。膜厚 150醒の ITOからなる陽極が形成されたガラス基板上に、各薄膜を真 空蒸着法にて、真空度 4.0 X 10— 4 Paで積層させた。まず、 ITO上に正孔輸送層として NPBを 60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物 40と Ir(ppy)とを異なる蒸着源から、共
3
蒸着し、 25nmの厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 %であった。次に、電
3
子輸送層として Alq3を 50應の厚さに形成した。更に、電子輸送層上に、電子注入層 としてフッ化リチウム (LiF)を 0.5應の厚さに形成した。最後に、電子注入層上に、電 極としてアルミニウム (A1)を 170nmの厚さに形成し、有機 EL素子を作成した。
[0088] 実施例 9 図 1において、正孔注入層を省略し、電子注入層を追加した構成の有機 EL素子を 作成した。膜厚 150應の ITOからなる陽極が形成されたガラス基板上に、各薄膜を真 空蒸着法にて、真空度 4.0 X 10— 4 Paで積層させた。まず、 ITO上に正孔輸送層として NPBを 60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物 27と Ir(ppy)とを異なる蒸着源から、共
3
蒸着し、 25應の厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 %であった。次に、電
3
子輸送層として Alq3を 50nmの厚さに形成した。更に、電子輸送層上に、電子注入層 としてフッ化リチウム (LiF)を 0.5應の厚さに形成した。最後に、電子注入層上に、電 極としてアルミニウム (A1)を 170nmの厚さに形成し、有機 EL素子を作成した。
[0089] 得られた有機 EL素子に外部電源を接続し直流電圧を印加したところ、表 2のような 発光特性を有することが確認された。表 2において、輝度、電圧及び発光効率は、 10 mA/cm2での値を示す。なお、素子発光スペクトルの極大波長は 517 nmであり、 Ir(ppy )力もの発光が得られていることがわ力つた。
3
[0090] 比較例 2
正孔輸送層として HMTPDを、発光層の主成分として TAZを用いた以外は実施例 7 と同様にして有機 EL素子を作成した。
[0091] 比較例 3
発光層の主成分として、 TAZを用いた以外は実施例 7と同様にして有機 EL素子を 作成した。
[0092] [表 2] 輝度（cd/m2) 電圧 (V) 視感発光効率
( l m/W)
実施例 7 2410 8. 0 9. 5
実施例 8 2300 6. 0 1 2. 0
実施例 9 2250 6. 0 1 1. 8
比較例 2 2050 13. 2 4. 9
比較例 3 1270 9. 5 4. 2 [0093] 実施例 10
(化合物 103の合成）
脱気窒素置換した 200ml三口フラスコに 1,2-シクロへキサンジオン 33.3g(0.297mol) 、フエ-ルヒドラジン塩酸塩 86.0g (0.595mol)をカ卩え、これにエタノール 1000mlをカロえ て攪拌させた。その後、同フラスコ内に濃硫酸 3.0g (0.03mol)を 5分間かけ滴下した。 その後 65°Cまで加熱し、 4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を 濾取した後、濾取した結晶をエタノール 500mlで二回、リスラリー洗浄をおこなった。こ れを、減圧乾燥して紫茶色粉末 80.0g (0.286mol、収率 96.3%)を得た。
次に、上記紫茶色粉末 72.0g (0.258mol)に、これに酢酸 720g、トリフルォロ酢酸 72.0 gを加えて攪拌させた。その後 100°Cまで加熱し、 15時間攪拌した。室温まで冷却した 後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸 200mlでリンス洗浄をおこな つた後、へキサン 200mlでリンス洗浄をおこなった。これを、減圧乾燥して白色粉末 30 .0g (0.117mol、収率 45.3%)を得た。
[0094] 次に、脱気窒素置換した 1000ml三口フラスコに上記で得た白色粉末 26.0g (0.101m ol)、ョードベンゼン 122.7g (0.601mol)、よう化銅 54.7g (0.287mol)、炭酸カリウム 66.7g (0.482mol)、これにキノリン 800mlを加えて攪拌させた。その後 190°Cまで加熱し、 72 時間攪拌した。ー且、室温まで冷却した後、水 500ml、ジクロロメタン 500mlを加え、攪 拌を行った後、生じた黄色結晶を濾取した。濾液を 2000ml分液ロートへ移し、有機層 と水層に分画した。有機層を 500mlの水で三回洗浄し、その後、得られた有機層を硫 酸マグネシウムで脱水を行い、一旦、硫酸マグネシウムを濾別した後、溶媒を減圧留 去した。その後、カラムクロマトグラフィーで精製して白色固体 13.7g (0.04mol、収率 4 0.8%)を得た。
次に、脱気窒素置換した 500ml三口フラスコに 55%水素化ナトリウム 2.16g (49.5mmol )、脱水 Ν,Ν，-ジメチルホルムアミド 70mlを加え、窒素気流中下で攪拌を行う。上記 で得た白色粉末 13.7g (40mmol)に脱水 Ν,Ν，-ジメチルホルムアミド 70mlをカ卩え、溶 解させ、その後、同フラスコ内に 15分間かけ滴下した。滴下終了後、 1時間攪拌を継 続した。その後、塩化シァヌル 2.46g (13mmol)に脱水 Ν,Ν，-ジメチルホルムアミド 70 mlを加え、溶解させ、その後、同フラスコ内に 15分間かけ滴下した。滴下終了後、内 温 80°Cで 24時間攪拌を «続した後、室温まで冷却した。冷却した後、同フラスコ内に 水 350gをカ卩え、析出した結晶を濾取した。濾取した結晶を水 300gで二回リスラリーを 行い、その後、メタノール 300gにてリスラリーを行った。これを減圧乾燥した後、カラム クロマトグラフィーで精製して淡黄色粉末 2. lg (2.0mmol、収率 15.5%)を得た。
化合物 103の EI— MS (M+ 1)は 1072、融点は 492°Cであった。
[0095] 実施例 11
ガラス基板上に真空蒸着法にて、真空度 4.0 X 10-4 Paの条件にて化合物 103を 蒸着源から蒸着し、薄膜を 1.0AZ秒にて 50應の厚さで形成した。作成した薄膜を、 蛍光測定装置にて評価した。次にガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4Paの条件にて化合物 3と Ir(ppy)3とを異なる蒸着源力も蒸着し、 Ir(ppy)3の濃度が 7.0 %であるような薄膜を 1.0AZ秒にて 50應の厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物 103の極大吸収 波長を使用し、そのときに出てくる光を観察し、化合物 103単独の薄膜の場合に出て くる光と比較した。結果を表 3に示す。
[0096] 比較例 4
薄膜主成分を Alq3に変えて薄膜を作成した以外は、実施例 11と同様に行った。結 果を表 3に示す。
[0097] [表 3]
Figure imgf000044_0001
実施例 12
図 1において、正孔注入層を省略し、電子注入層を追加した構成の有機 EL素子を 作成した。膜厚 150應の ITOからなる陽極が形成されたガラス基板上に、各薄膜を真 空蒸着法にて、真空度 4.0 X 10— 4 Paで積層させた。まず、 ITO上に正孔輸送層として NPBを 60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物 103と Ir(ppy)とを異なる蒸着源から、 共蒸着し、 25應の厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 %であった。次に、
3
電子輸送層として Alq3を 50nmの厚さに形成した。更に、電子輸送層上に、電子注入 層としてフッ化リチウム (LiF)を 0.5應の厚さに形成した。最後に、電子注入層上に、 電極としてアルミニウム (A1)を 170nmの厚さに形成し、有機 EL素子を作成した。
[0099] 得られた有機 EL素子に外部電源を接続し直流電圧を印カロしたところ、表 4のような 発光特性を有することが確認された。表 4において、輝度、電圧及び発光効率は、 10 mA/cm2での値を示す。なお、素子発光スペクトルの極大波長は 517 nmであり、 Ir(ppy )力もの発光が得られていることがわ力つた。
3
[0100] 比較例 5
正孔輸送層として HMTPDを、発光層の主成分として TAZを用いた以外は実施例 1 2と同様にして有機 EL素子を作成した。
[0101] 比較例 6
発光層の主成分として、 TAZを用いた以外は実施例 12と同様にして有機 EL素子 を作成した。
[0102] [表 4]
Figure imgf000045_0001
産業上の利用の可能性
[0103] 本発明の有機 EL素子は、低電圧において高輝度'高効率で発光させることが可能 となる。したがって、本発明による有機 EL素子はフラットパネル'ディスプレイ (例えば OAコンピュータ用や壁掛けテレビ)、車載表示素子、携帯電話表示や面発光体とし ての特徴を生カゝした光源 (例えば、複写機の光源、液晶ディスプレイや計器類のバッ クライト光源）、表示板、標識灯への応用が考えられ、その技術的価値は大きいもの である。

Claims

請求の範囲 下記一般式 (1)で表わされる有機電界発光素子用化合物。 z -ev ) n
( 1 )
(式中、 Zは縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複 素環基からなる連結基を示し、 Yは下記一般式（la)で表わされる基を示し、 nは 2以 上の整数を示す。 )
Figure imgf000046_0001
(式中、環 A隣接環と縮合する式（lb)で表わされる芳香族環又は複素環を示し、環 B は隣接環と縮合する式（lc)で表わされる複素環を示し、 Xは炭素又は窒素を示し、 R は水素、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複 素環基、又は Xを含む環と縮合する環を示し、 R
44は縮環構造でない置換若しくは未 置換の芳香族炭化水素基又は芳香族複素環基を示し、 R 、R
41 42は、水素、アルキル 基、ァラルキル基、ァルケ-ル基、アルキ-ル基、シァノ基、ジアルキルアミノ基、ジァ リールアミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基、ァシル基、アルコキシカル ボ-ル基、カルボキシル基、アルコキシル基、アルキルスルホ-ル基、ハロアルキル 基、水酸基、アミド基、置換又は未置換の芳香族炭化水素基又は芳香族複素環基を 示す。）
一般式（1)において、 Yが一般式（Id)を表わされる基である請求項 1記載の有機 電界発光素子用化合物。
Figure imgf000047_0001
(式中、 R
5は R
43と同じ意味を有し、 R
46は R
44と同じ意味を有し、 R 、R
47 48は独立に、 R
4 4
1と同じ意味を有する。 )
下記一般式 (2)又は（3)で表される請求項 1に記載の有機電界発光素子用化合物
Figure imgf000048_0001
Figure imgf000048_0002
(式中、環 A、環 A'は隣接環と縮合する式（2a)で表される芳香環又は複素環を示し 、環 B、環 B'は隣接環と縮合する式（2b)で表される複素環を示し、 Arは縮環構造
1
でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基力もなる 2価 の連結基を示し、 Xは炭素又は窒素を示し、 R
5は水素、縮環構造でない置換若しく は未置換の芳香族炭化水素基又は芳香族複素環基を示し、 R
6は縮環構造でない 置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、 R〜Rは独
1 4 立に、水素、アルキル基、ァラルキル基、ァルケ-ル基、アルキ-ル基、シァノ基、ジ アルキルアミノ基、ジァリールアミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基、ァシ ル基、アルコキシカルボ-ル基、カルボキシル基、アルコキシル基、アルキルスルホ ニル基、ハロアルキル基、水酸基、アミド基、置換又は未置換の芳香族炭化水素基 又は芳香族複素環基を示す。 )
Figure imgf000049_0001
Figure imgf000049_0002
(式中、環 C、環 C'は隣接環と縮合する式 (3a)で表される芳香環又は複素環を示し 、環 D、環 D'は隣接環と縮合する式（3b)表される複素環を示し、環 E、環 E'は隣接 環と縮合する式（3c)で表される複素環を示し、 Arは縮環構造でない置換若しくは
2
未置換の芳香族炭化水素基又は芳香族複素環基力 なる 2価の連結基を示し、 Xは 炭素又は窒素を示し、 R R 〜R
13は 5と同じ意味を有し、 R
14 15は独立に、 R
6と同じ意味を 有し、 R〜R は独立に、 Rと同じ意味を有する。 )
7 12 1
下記一般式 (4)又は (5)で示される請求項 1記載の有機電界発光素子用化合物。
Figure imgf000050_0001
(式中、 Arは縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族
3
複素環基からなる 2価の連結基を示し、 R 、R は水素、縮環構造でない置換若しく
17 20
は未置換の芳香族炭化水素基又は芳香族複素環基を示し、 R 、 R
22 23は縮環構造で ない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、 R 、 R
16 18
、 R 、 R は、水素、アルキル基、ァラルキル基、アルケニル基、アルキニル基、シァノ
19 21
基、ジアルキルアミノ基、ジァリールアミノ基、ジァラルキルアミノ基、アミノ基、ニトロ基 、ァシル基、アルコキシカルボ-ル基、カルボキシル基、アルコキシル基、アルキルス ルホニル基、ハロアルキル基、水酸基、アミド基、置換若しくは未置換の芳香族炭化 水素基又は芳香族複素環基を示す。 )
Figure imgf000051_0001
Figure imgf000051_0002
(式中、環 F、環 F'は隣接環と縮合する式（5a)で表される複素環を示し、 Arは Arと
4 3 同じ意味を有し、 R 〜R
32は独立に、 R 〜R
22と同じ意味を有し、 R
24 29は独立に、 R
30 16と 同じ意味を有する。 )
一般式（2)〜（5)及び式（2a)〜（2c)、（3a)〜（3c)、（5a)中、環 A、 A'、 C、 C'が ベンゼン環であり、 R、R 〜R 、R 〜R 、R 〜R が置換若しくは未置換のフエ-
6 14 15 22 23 30 32
ル基又はピリジル基であり、且つ、 R〜R、R〜R 、R 〜R 、R 〜R
1 4 7 12 16 21 24 29が水素又は フエニル基である請求項 3又は 4に記載の有機電界発光素子用化合物。
一般式（1)において、 nが 3又は 4である請求項 1又は 2に記載の有機電界発光素 子用化合物。
基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であつ て、該発光層が、燐光発光性ドーパントと請求項 1〜6のいずれかに記載の有機電 界発光素子用化合物をホスト材料として含有することを特徴とする有機電界発光素 子。
陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を 有してなる請求項 7記載の有機電界発光素子。 [9] 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項 8記載の有機電 界発光素子。
PCT/JP2006/323290 2005-12-01 2006-11-22 有機電界発光素子用化合物及び有機電界発光素子 Ceased WO2007063754A1 (ja)

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EP1956022B1 (en) 2012-07-25
US7993760B2 (en) 2011-08-09
CN102633820A (zh) 2012-08-15
JP4593631B2 (ja) 2010-12-08
TWI378099B (ja) 2012-12-01
CN101321755B (zh) 2012-04-18
CN101321755A (zh) 2008-12-10
EP1956022A4 (en) 2011-07-13
TW200734340A (en) 2007-09-16
KR20080085001A (ko) 2008-09-22
CN102633820B (zh) 2015-01-21
JPWO2007063754A1 (ja) 2009-05-07
US20090302742A1 (en) 2009-12-10
EP1956022A1 (en) 2008-08-13
KR101082258B1 (ko) 2011-11-09

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