TW200948929A - Material for organic electro-luminescence element and organic electro-luminescence element - Google Patents

Material for organic electro-luminescence element and organic electro-luminescence element Download PDF

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TW200948929A
TW200948929A TW098105390A TW98105390A TW200948929A TW 200948929 A TW200948929 A TW 200948929A TW 098105390 A TW098105390 A TW 098105390A TW 98105390 A TW98105390 A TW 98105390A TW 200948929 A TW200948929 A TW 200948929A
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Taiwan
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compound
substituted
group
unsubstituted
organic
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TW098105390A
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Chinese (zh)
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Yoshiyuki Takata
Tohru Iwata
Tetsuya Kaneko
Junpei Hayakawa
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Toyo Ink Mfg Co
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Priority claimed from JP2008040803A external-priority patent/JP2009197144A/en
Priority claimed from JP2008085146A external-priority patent/JP2009235292A/en
Priority claimed from JP2008225383A external-priority patent/JP2010059293A/en
Application filed by Toyo Ink Mfg Co filed Critical Toyo Ink Mfg Co
Publication of TW200948929A publication Critical patent/TW200948929A/en

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Abstract

Provided is a material for organic electro-luminescence element which is a compound represented by the following general formula [1]. (wherein Ar1 and Ar2 respectively independently represents substituted or unsubstituted divalent aromatic hydrocarbon group, or substituted or unsubstituted divalent aromatic heterocyclic group, Ar3 represents substituted or unsubstituted condensed aromatic hydrocarbon group, or substituted or unsubstituted condensed aromatic heterocyclic group, Ar4 represents hydrogen atom, substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group, X represents S, O or N-Ar5, wherein Ar5 represents substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group, R1 and R2 respectively independently represents hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted alkoxy group, or substituted or unsubstituted aryloxy group, wherein R1 and R2 may couple to each other to form a ring.)

Description

i 200948929 六、發明說明： 【發明所屬之技術領域】 場發光元件 【先前技術】 本發明係關於使用於平面光源或顯示之有機電場發 光巧件用材料及使用該有機電場發光元件特料之有機電 有機電場發光（以下稱為有機EL)元件，當從陰 入之電子與從陽極所注人之電洞，在夾持於此兩極間之有 ❹機螢光體内再次結合時會發光。有機EL元件，有另 固體發光型顯示元件的料，因此，近年來積極地進^ 發。 此研究係由Eastman Kodak公司的c. W. Tang氏等 人，發端於一種積層有有機薄膜之EL元件。於此報告中， 藉由將金屬螯合錯合物使用於發光層，將胺系化合物使用 於電洞注入層，而獲得在6至ιον的直流電壓下之亮度為 ❹數10〇〇(cd/m2)、最大發光效率為之綠色發光 (非專利文獻1)。目前，於各種研究機構中，正朝向全彩 顯不器的實用化，進行有機EL元件之高效率化、高耐久化 之研究，並探討各種構造的材料作為有機EL元件用材料。 有機EL元件，至目前為止已進行使用各種材料之元 件的研究，亦已探討使用雜五員環化合物之有機EL元件。 正進行例如噻吩衍生物（專利文獻1至4)、呋喃衍生物（專 利文獻5至7)、吡咯衍生物（專利文獻8至13)等之探討。 非專利文獻 l :Appl. Phys. Lett.，第 51 卷，913 321062 3 200948929 頁，1987年 專利文獻1: 專利文獻2 : 專利文獻3 : 專利文獻4 : 專利文獻5： 專利文獻6 : 專利文獻7 : 專利文獻8 : 專利文獻9 : 專利文獻10 專利文獻11 專利文獻12 專利文獻13 【發明内容】 曰本特開平4-304466號公叙 曰本特開2000-26451號公報 曰本特開2005-63679號公報 曰本特開2003-13054號公報 曰本特開平10-125468號公報 曰本特開平10-152676號公報 曰本特開11-111460號公報 曰本特開2000-260567號公報 曰本特開2003-129044號公報 曰本特開2004-075980號公報 曰本特開2004-311410號公報 曰本特開2004-311412號公報 曰本特開2004-335427號公報 (發明欲解決之課題） 本發明之一實施型態的課題係，為了提升有機EL元 件的性能，而提供一種較使用先前技術所述之 EL元件’更能夠顯現出高效率、長壽命，並且點=機的 免度降低較緩慢之有機EL元件用材料及有機EL元件。提 升有機EL兀件的效率係，即使使用較小的電能亦可獲得強 的亮度’且就凡件的驅動電壓之降低而言乃極為重要，並 且了抑制對το件所施加之電性負擔，因此，有益於元件的 長哥命化。亦即，本發明之-實施型態的課題’在於提供 4 321062 200948929 一種可顯現出低電壓驅動、4 有機EL元件。 *科、耐驗料良特性之 (解決課題之手段） 本發明人係考量並為了敵 關於-種有機電場發光元件用二本:特::實施型態係 式⑴所表示之化合物：材枓’其特徵是由下列一般 ❹i 200948929 VI. Description of the Invention: [Technical Field] The field light-emitting element [Prior Art] The present invention relates to a material for an organic electric field light-emitting component used for a planar light source or display, and the use of the organic electric field light-emitting element An electromechanical organic electric field illuminating element (hereinafter referred to as an organic EL) element emits light when the electrons from the yin and the holes injected from the anode are recombined in the fluorescing phosphor between the two electrodes. Since the organic EL element has a material of another solid-state light-emitting display element, it has been actively promoted in recent years. This study was initiated by C. W. Tang et al. of Eastman Kodak Company, Inc., starting with an EL element with an organic film laminated. In this report, by using a metal chelate complex for the light-emitting layer, an amine compound is used for the hole injection layer, and a luminance of 10 〇〇 at a DC voltage of 6 to ιον is obtained. /m2), the maximum luminous efficiency is green light emission (Non-Patent Document 1). At present, in various research institutes, the use of organic EL elements for high efficiency and high durability has been studied, and materials of various structures have been examined as materials for organic EL elements. Organic EL elements have been studied for the use of various materials up to now, and organic EL elements using a heteroquinone ring compound have also been examined. For example, thiophene derivatives (Patent Documents 1 to 4), furan derivatives (Patent Documents 5 to 7), and pyrrole derivatives (Patent Documents 8 to 13) are being examined. Non-Patent Document 1: Appl. Phys. Lett., Vol. 51, 913 321062 3 200948929, 1987 Patent Document 1: Patent Document 2: Patent Document 3: Patent Document 4: Patent Document 5: Patent Document 6: Patent Literature 7 : Patent Document 8 : Patent Document 9 : Patent Document 10 Patent Document 11 Patent Document 12 Patent Document 13 [Summary of the Invention] 曰本特开平4-304466号 公曰 曰本特开 2000-26451号曰本特开2005 Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Japanese Unexamined Patent Publication No. Publication No. No. No. No. No. No. No. Publication No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. No An object of an embodiment of the present invention is to provide a higher efficiency, a longer life, and a point-free machine than the EL element described in the prior art in order to improve the performance of the organic EL element. Reduce slower organic EL elements And an organic EL element material. The efficiency of the organic EL element is improved, and a strong brightness can be obtained even with a small electric energy', and it is extremely important in terms of the reduction of the driving voltage of the piece, and the electric load imposed on the τ piece is suppressed. Therefore, it is beneficial to the long brother of the component. That is, the subject matter of the present invention is to provide 4 321062 200948929, a low voltage drive, 4 organic EL device. *Means, and good resistance to good materials (the means to solve the problem) The inventors of the present invention have considered two types of organic electric field light-emitting elements for use in an enemy-specific type: special:: a compound represented by the type (1): 'It is characterized by the following general ❹

Ar3—Ar1. xAr3—Ar1. x

Ar2— R1 R2 般式[1] [式中’ Ar1及Ar2分为丨你 芳香族烴基、或是取代咬未^地為取代或未取代的Μ 、ΑΓ為取代或未取代的縮合芳香族煙基、二公、 取代的縮合芳麵雜環基； 5 (取代或 ❹Ar2— R1 R2 General formula [1] [In the formula, Ar1 and Ar2 are classified as 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 、 、 、 、 、 、 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 芳香族 Ar Ar Ar Ar Ar Ar Ar Alkyl, di-, substituted fused aromatic heterocyclic; 5 (substituted or deuterated)

Ar為氫原子、取代或未取代的芳香族 或未取代的芳香族雜環基； 基或疋取, x為S、0、或N_紅5 為 香族煙基、或是為取代或未取代的5 1 2飞疋取代或未取代的芳香族雜環基； 只及β分別獨立地為氫、 在此;…二的 =是取代或未取代的芳氧基 元件，：在明之一實施型態係關於一種有機電場發片 .-在由陽極與陰極所成之一對電極間，形成一層或 321062 5 200948929 w 多層的有機層而成之有機電場發光元件，其中，至少1層 為含有上述有機電場發光元件用材料的層。 再者，本發明之一實施型態係關於一種有機電場發光 元件，係在由陽極與陰極所成之一對電極間，形成至少一 層的發光層而成之有機電場發光元件，其中，發光層為含 有上述有機電場發光元件用材料的層。 再者，本發明之一實施型態係關於一種有機電場發光 元件，係在由陽極與陰極所成之一對電極間，形成至少一 層的發光層而成之有機電場發光元件，其中，係使用上述 Ο 有機電場發光元件用材料作為發光層主材料。 再者，本發明之一實施型態係關於一種有機電場發光 元件，係在由陽極與陰極所成之一對電極間，形成至少一 層的發光層而成之有機電場發光元件，其中，電子傳輸層 為含有上述有機電場發光元件用材料的層。 (發明之效果） 使用由一般式[1]所表示之化合物之有機EL元件，可 實現高亮度、高效率、長壽命、以及高初期安定性。 本發明之揭示，係關於2008年2月22曰所申請之曰 本特願2008-040803、2008年3月28日所申請之日本特願 2008-085146及2008年9月3日所申請之日本特願 2008-225383中所包含之主題，並將於這些說明書中所揭 示之事項明確地編入於本說明書中。 【實施方式】 以下詳細說明本發明之由一般式[1]中所表示之化合 6 321062 200948929 物。一般式[1]中之Ar1及Ar2， 價芳香族烴基、或是取代或未取^不取代或未取代的2 價芳香族雜環基。Ar is a hydrogen atom, a substituted or unsubstituted aromatic or unsubstituted aromatic heterocyclic group; a base or a draw, x is S, 0, or N_red 5 is a scented smog group, or is substituted or not Substituted 5 1 2 indole substituted or unsubstituted aromatic heterocyclic group; only β is independently hydrogen, here; ... is a substituted or unsubstituted aryloxy element, The type is related to an organic electric field emitting sheet. An organic electroluminescent element is formed by forming a layer or a 32122 5 200948929 w multilayer organic layer between a pair of electrodes formed by an anode and a cathode, wherein at least one layer contains A layer of the material for an organic electric field light-emitting element. Furthermore, an embodiment of the present invention relates to an organic electroluminescent device which is an organic electroluminescent device in which at least one light-emitting layer is formed between a pair of electrodes formed by an anode and a cathode, wherein the light-emitting layer is formed. It is a layer containing the material for organic light-emitting elements described above. Furthermore, an embodiment of the present invention relates to an organic electric field light-emitting element, which is an organic electric field light-emitting element formed by forming at least one light-emitting layer between a pair of electrodes formed by an anode and a cathode, wherein The above-mentioned material for the organic electroluminescent element is used as the main material of the light-emitting layer. Furthermore, an embodiment of the present invention relates to an organic electric field light-emitting element, which is an organic electric field light-emitting element in which at least one light-emitting layer is formed between a pair of electrodes formed by an anode and a cathode, wherein electron transport is performed. The layer is a layer containing the material for the above organic electroluminescent element. (Effect of the Invention) The organic EL device of the compound represented by the general formula [1] can achieve high brightness, high efficiency, long life, and high initial stability. The disclosure of the present invention relates to Japan's special wish 2008-040803, which was filed on February 22, 2008, and Japan's special application 2008-085146, which was filed on March 28, 2008, and Japan applied for on September 3, 2008. The subject matter contained in the Japanese Patent Application No. 2008-225383, the entire disclosure of which is hereby incorporated by reference. [Embodiment] Hereinafter, the compound 6 321062 200948929 represented by the general formula [1] of the present invention will be described in detail. Ar1 and Ar2 in the general formula [1], a valent aromatic hydrocarbon group, or a substituted or unsubstituted unsubstituted or unsubstituted divalent aromatic heterocyclic group.

Ai^-Ar1Ai^-Ar1

A^-Ar4 R1 〜般式[1] 在此，2償芳香族烴基例如有伸苯基 ^ ί、伸菲基、伸苗基、伸稠四苯基、伸稠五苯伸= 等。當中較理想為伸苯基、伸萘基、伸惠基、伸菲 此外’2價芳香族雜環基例如有伸吡啶美 ^ 伸異啥琳基、:伸㈣基、伸苯并嗟吩基^啥琳基、 伸吲哚基等6當中鲂理相盔妯邮&甘 r本井味喃基、 料基。J切想為伸对基、伸㈣基、伸苯并 此外’上述一般式[1 ]中之ΑΓ3，倍± 、 7合芳料《.、.歧取代或絲代的料^族未雜取環代 ❹ 此’維合芳香族烴基例如有萘基、蒽基、菲基、翻 萘ί 、=、錄m #中較理想為 苯并縮合芳香族雜環基例如有㈣基、異麵基、 ♦ % 土、苯并呋喃基、吲哚基、啡啉基、咔唑基等。 田中較理想為料基、苯并嘆吩基、料咬喃基、十坐基。 或未此外，上述一般式π]中之紅4，係表示氫原子、取代 美。取代的芳香族烴基、或是取代或未取代的芳香族雜 321062 7 200948929 在此，芳香族蛵基例如有苯基、聯笨基、三苯基、萘 基、蒽基、菲基、裯五苯基、四伸苯基、芘基、茈基、芴 基等。當中較理想為苯基、聯苯基、三苯基、萘基、茛美、 菲基、芴基。 ‘如土、 此外，芳香族雜環基例如有吡啶基、吡卩井基、嘧啶基、 三氮雜苯基、喹啉基、異喹啉基、苯并噻吩基、苯并呋喃 基、㈣基、《基、唯嗤基等。當中較理想為吧咬基、 ’基、料基、苯并嘆吩基、苯并咳㉝基、Μ基。 此外，上述一般式[1]中之X為s、〇、或恥Ar5。Ar5 係表示取㈣未取代料錢烴基、或是取代 芳香族雜環基。 在此士5中之芳香族烴基及芳香族雜環基，例如有與 Ar中之芳香族煙基及芳香族雜環基為相同者。 上述Ar至Ar可具有取代基。在此，紅1至紅5所能 夠具有之取代基’例如有烧基、芳麵烴基、芳香族雜環 基、烷氧基、或是芳氧基。 在此’燒基有由碳數1至18個所形成之烧基。此類 燒基例如有甲基、乙基、丙基、異㊉基、正丁基、異丁基、 二級丁基、三級丁基、戊基、異絲、己基、庚基、辛基、 癸基、十沐基、十五燒基、十八燒基等。較理想為由碳 數1至4個所形成之燒基，例如有甲基、乙基、正兩基、 異丙基、jH·丁基、三級丁基等。 此外’方香族烴基例如有與Ar4中之芳香族烴基為相 同者。 321062 8 200948929 此外，芳香族雜環基例如有與ΑΓ4中—香矣雜《其 為相.同者。. ” 此外，烷氧基例如有:氣基、乙氧基、丁氧基、辛氧 基、癸氧基等烧氧基。當中較理想為甲mm 氧基。 π二外二氧基為0鍵。於與Al*4中之芳香族烴基為相 同的基而戒者，例如有苯氧基、萘氣基等 ο 此外’上述一般式[1]中之R1 取代或未取代W、取錢柄代^=原ζ代 ==香族雜環基、取代或未取代=、= 取代^取代的芳氧基。此外，r2可鍵結_成環。 m ；^及R中之烧基、芳香族烴基、芳香族雜環基、 烧3、及方氣基，例如有與“至Αγ5中之烧基、芳香 矢炫基、务香族雜環基、院氧基、及芳氧基為相同者。 此外’ R及R2可具有取代基。 ❹ 5在此，R及R2所能夠具有之取代基’例如有與Ar1至 Ar所能夠具有之取代基為相同者。 下係於第1表中表示本發明之有機EL元件中所 =用_之由—般式[1]所表示之有機EL元件詩料的代 例例不化合物1至440)，但本發明並不限定於此。 9 321062 200948929 [第1表] 號碼 化學構造 號碼 化學構造 1 2 3 4 0#CN3rC^ 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Q 19 2 0 10 321062 200948929A^-Ar4 R1~ General Formula [1] Here, the 2-valent aromatic hydrocarbon group is, for example, a stretching phenyl group, a phenanthrene group, a stretching base group, a thickened tetraphenyl group, a thickened pentabenzene extension, and the like. Among them, it is preferred to be a phenyl group, an anthranyl group, a stilbene group, a phenanthrene group, and a '2-valent aromatic heterocyclic group, for example, a pyridine group, a stilbene group, an exo (tetra) group, and a benzophenanthenyl group. ^啥琳基, 伸吲哚基, etc. among the 6 鲂 相 妯 & & & & 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘 甘J is conceived as a base, a (four) base, a benzene extension, and a ΑΓ3 in the above general formula [1], a double, a hexagram, or a singular material. ' ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ❹ ♦ % soil, benzofuranyl, fluorenyl, morpholinyl, carbazolyl and the like. Tanaka is ideally based on the base material, benzophenanthrene, butyl base, and ten base. Or not, the red 4 in the above general formula π] represents a hydrogen atom and a substituted beauty. Substituted aromatic hydrocarbon group or substituted or unsubstituted aromatic impurity 321067 200948929 Here, the aromatic fluorenyl group is, for example, a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group or a fluorene group. Phenyl, tetraphenylene, fluorenyl, fluorenyl, fluorenyl and the like. More preferably, it is a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, a fluorene group, a phenanthryl group or a fluorenyl group. '如土, In addition, the aromatic heterocyclic group is, for example, pyridyl, pyridinium, pyrimidinyl, triazaphenyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, (d) Base, "base, only 嗤 base." Preferably, it is a bite base, a base, a base, a benzophenanyl group, a benzocyanato 33 group, or a fluorenyl group. Further, X in the above general formula [1] is s, 〇, or shame Ar5. The Ar5 system represents a (iv) unsubstituted hydroxy group or a substituted aromatic heterocyclic group. The aromatic hydrocarbon group and the aromatic heterocyclic group in the group 5 are, for example, the same as the aromatic smoky group and the aromatic heterocyclic group in Ar. The above Ar to Ar may have a substituent. Here, the substituent which the red 1 to the red 5 can have is, for example, a burnt group, an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkoxy group or an aryloxy group. Here, the alkyl group has a burnt group formed by 1 to 18 carbon atoms. Such alkyl groups are, for example, methyl, ethyl, propyl, isodecyl, n-butyl, isobutyl, secondary butyl, tert-butyl, pentyl, iseth, hexyl, heptyl, octyl , 癸基, 十沐基, fifteen burning base, eighteen burning base, etc. The alkyl group formed by 1 to 4 carbon atoms is preferable, and examples thereof include a methyl group, an ethyl group, a n-diyl group, an isopropyl group, a jH-butyl group, a tertiary butyl group and the like. Further, the 'fragrant aromatic hydrocarbon group is, for example, the same as the aromatic hydrocarbon group in Ar4. 321062 8 200948929 In addition, the aromatic heterocyclic group is, for example, the same as ΑΓ4. Further, the alkoxy group is, for example, an alkoxy group such as a gas group, an ethoxy group, a butoxy group, an octyloxy group or a decyloxy group, and more preferably a methyloxy group. The π di-dioxy group is 0. The bond is the same as the aromatic hydrocarbon group in Al*4, and is, for example, a phenoxy group, a naphthalene group, or the like. Further, R1 in the above general formula [1] is substituted or unsubstituted, and money is taken.柄代^=原原代== Aromatic heterocyclic group, substituted or unsubstituted =, = substituted aryloxy group. In addition, r2 can be bonded to form a ring. m ; ^ and R in the alkyl group, The aromatic hydrocarbon group, the aromatic heterocyclic group, the calcined carbon group, and the gas group are, for example, the same as the "alkyl group, the aromatic fluoranyl group, the sulphur heterocyclic group, the alkoxy group, and the aryloxy group". The same. Further, 'R and R2 may have a substituent. Here, the substituent " which R and R2 can have" is, for example, the same as the substituent which Ar1 to Ar can have. In the organic EL device of the present invention, the organic EL device of the present invention is represented by the first embodiment, and the example of the organic EL device shown in the general formula [1] is not the compound 1 to 440), but the present invention It is not limited to this. 9 321062 200948929 [Table 1] No. Chemical structure No. Chemical structure 1 2 3 4 0#CN3rC^ 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Q 19 2 0 10 321062 200948929

11 321062 >4200948929 4 1 Q ^ 4 2 4 3 44 4 5 4 6 4 7 4 8 4 9 5 0 5 1 52 5 3 54 5 5 cip O^yO 5 6 5 7 5 8 §^ir^ 5 9 6 011 321062 >4200948929 4 1 Q ^ 4 2 4 3 44 4 5 4 6 4 7 4 8 4 9 5 0 5 1 52 5 3 54 5 5 cip O^yO 5 6 5 7 5 8 §^ir^ 5 9 6 0

Ο 12 321062 200948929 6 1 6 2 6 3 64 °^^τ〇 6 5 6 6 GcX^rJ^ 6 7 Q 6 8 6 9 70 7 1 7 2 73 74 7 5 76 77 78 °iW&%° 7 9 §^% 80 §^ύτ^)) 13 321062 200948929Ο 12 321062 200948929 6 1 6 2 6 3 64 °^^τ〇6 5 6 6 GcX^rJ^ 6 7 Q 6 8 6 9 70 7 1 7 2 73 74 7 5 76 77 78 °iW&%° 7 9 §^% 80 §^ύτ^)) 13 321062 200948929

❿ 14 321062 200948929 Ο ❹ 101 10 2 10 3 104 10 5 10 6 10 7 10 8 10 9 110 °^P 111 °w° 112 °w° 113 Q Q ^2° 114 °w° 115 116 ob 117 118 119 12 0 15 321062 200948929 12 1 ^〇%° 12 2 123 0^-0 124 12 5 〇? §〇 12 6 〇00 O^yD 12 7 12 8 12 9 13 0 ^〇S〇 13 1 13 2 13 3 134 13 5 Q Q 136 13 7 13 8 13 9 140 © 16 321062 200948929 ❹ 141 14 2 143 1 4 4 14 5 14 6 14 7 14 8 14 9 15 0 15 1 15 2 15 3 154 15 5 15 6 15 7 15 8 15 9 16 0 17 321062 200948929 16 1 16 2 16 3 16 4 16 5 16 6 16 7 16 8 1 6 9 17 0 17 1 8^r^° 17 2 17 3 174 Q- 17 5 17 6 17 7 17 8 17 9 18 0❿ 14 321062 200948929 Ο ❹ 101 10 2 10 3 104 10 5 10 6 10 7 10 8 10 9 110 °^P 111 °w° 112 °w° 113 QQ ^2° 114 °w° 115 116 ob 117 118 119 12 0 15 321062 200948929 12 1 ^〇%° 12 2 123 0^-0 124 12 5 〇? §〇12 6 〇00 O^yD 12 7 12 8 12 9 13 0 ^〇S〇13 1 13 2 13 3 134 13 5 QQ 136 13 7 13 8 13 9 140 © 16 321062 200948929 ❹ 141 14 2 143 1 4 4 14 5 14 6 14 7 14 8 14 9 15 0 15 1 15 2 15 3 154 15 5 15 6 15 7 15 8 15 9 16 0 17 321062 200948929 16 1 16 2 16 3 16 4 16 5 16 6 16 7 16 8 1 6 9 17 0 17 1 8^r^° 17 2 17 3 174 Q- 17 5 17 6 17 7 17 8 17 9 18 0

18 321062 200948929 ❹ ❹ 18 1 18 2 18 3 184 18 5 18 6 18 7 18 8 6^6 18 9 190 19 1 19 2 193 194 19 5 19 6 19 7 °^S3r^ 19 8 19 9 200 Q ^ Γ9 321062 200948929 2 0 1 Q 20 2 203 204 2 0 5 206 207 2 0 8 2 0 9 2 10 2 11 2 12 2 13 2 14 §^ir% 2 15 2 16 2 17 2 18 2 19 2 2 0 20 321062 200948929 ❹18 321062 200948929 ❹ ❹ 18 1 18 2 18 3 184 18 5 18 6 18 7 18 8 6^6 18 9 190 19 1 19 2 193 194 19 5 19 6 19 7 °^S3r^ 19 8 19 9 200 Q ^ Γ9 106^ir% 2 15 2 16 2 17 2 18 2 19 2 2 0 20 321062 200948929 ❹

200948929 24 1 242 24 3 244 24 5 2 4 6 247 248 5^¾¾ 249 2 5 0 2 5 1 °w° 2 5 2 °w° 2 5 3 2 54 °w° 2 5 5 Q Q 〇 2 5 6 2 5 7 2 5 8 OQ 2 5 9 ^SS 2 6 0200948929 24 1 242 24 3 244 24 5 2 4 6 247 248 5^3⁄43⁄4 249 2 5 0 2 5 1 °w° 2 5 2 °w° 2 5 3 2 54 °w° 2 5 5 QQ 〇2 5 6 2 5 7 2 5 8 OQ 2 5 9 ^SS 2 6 0

22 321062 200948929 2 6 1 2 6 2 2 6 3 264 2 6 5 2 6 6 2 6 7 268 2 6 9 270 2 7 1 2 72 2 7 3 ©ip 2 74 /¾ 2 7 5 δ〇 cv 276 °w° 2 7 7 278 i % 2 7 9 28 0 23 321062 200948929 28 1 Op Q 28 2 2 8 3 2 8 4 C^r〇r^ 2 8 5 2 8 6 0^0 2 8 7 2 8 8 %^〇 2 8 9 & 〇0〇 2 9 0 & ,ά9 2 9 1 2 9 2 ^0^0 2 9 3 294 2 9 5 2 9 6 0 0¾^ 2 9 7 298 2 9 9 3 0 0 Q^o22 321062 200948929 2 6 1 2 6 2 2 6 3 264 2 6 5 2 6 6 2 6 7 268 2 6 9 270 2 7 1 2 72 2 7 3 ©ip 2 74 /3⁄4 2 7 5 δ〇cv 276 °w ° 2 7 7 278 i % 2 7 9 28 0 23 321062 200948929 28 1 Op Q 28 2 2 8 3 2 8 4 C^r〇r^ 2 8 5 2 8 6 0^0 2 8 7 2 8 8 %^ 〇2 8 9 & 〇0〇2 9 0 & ά9 2 9 1 2 9 2 ^0^0 2 9 3 294 2 9 5 2 9 6 0 03⁄4^ 2 9 7 298 2 9 9 3 0 0 Q ^o

24 321062 200948929 〇 ❿ 3 0 1 30 2 3 0 3 304 3 0 5 3 0 6 5^0^0¾ 3 0 7 ^0^0¾ 3 0 8 3 0 9 3 10 3 11 3 12 3 13 3 14 3 15 3 16 〇%〇^〇^0 3 17 3 18 3 19 3 2 0 25 321062 200948929 3 2 1 3 2 2 Λ 3 2 3 324 3 2 5 3 2 6 3 2 7 3 2 8 3 2 9 °Λ%° 3 3 0 3 3 1 3 3 2 3 3 3 3 34 3 3 5 §H^<y% 3 3 6 3 3 7 338 3 3 9 34024 321062 200948929 〇❿ 3 0 1 30 2 3 0 3 304 3 0 5 3 0 6 5^0^03⁄4 3 0 7 ^0^03⁄4 3 0 8 3 0 9 3 10 3 11 3 12 3 13 3 14 3 15 3 16 〇%〇^〇^0 3 17 3 18 3 19 3 2 0 25 321062 200948929 3 2 1 3 2 2 Λ 3 2 3 324 3 2 5 3 2 6 3 2 7 3 2 8 3 2 9 °Λ% ° 3 3 0 3 3 1 3 3 2 3 3 3 3 34 3 3 5 §H^<y% 3 3 6 3 3 7 338 3 3 9 340

26 321062 200948929 34 1 34 2 ^2s 343 344 34 5 346 34 7 σ§^ 348 >0^0 349 350 3 5 1 & 3 5 2 JCH, 3 5 3 354 355 356 357 3 5 8 3 5 9 M〇%° 3 6 0 CH^〇S〇%° 27 321062 200948929 3 6 1 3 6 2 3 6 3 3 6 4 3 6 5 3 6 6 3 6 7 3 6 8 3 6 9 3 7 0 3 7 1 ^%° 3 7 2 6¾5^°¾ 3 7 3 3 74 %Μ° 3 7 5 3 7 6 3 7 7 °%S^ 3 7 8 3 7 9 3 8 0 °^τ〇^ Ο26 321062 200948929 34 1 34 2 ^2s 343 344 34 5 346 34 7 σ§^ 348 >0^0 349 350 3 5 1 & 3 5 2 JCH, 3 5 3 354 355 356 357 3 5 8 3 5 9 M〇%° 3 6 0 CH^〇S〇%° 27 321062 200948929 3 6 1 3 6 2 3 6 3 3 6 4 3 6 5 3 6 6 3 6 7 3 6 8 3 6 9 3 7 0 3 7 1 ^%° 3 7 2 63⁄45^°3⁄4 3 7 3 3 74 %Μ° 3 7 5 3 7 6 3 7 7 °%S^ 3 7 8 3 7 9 3 8 0 °^τ〇^ Ο

28 321062 200948929 〇 ❹ 3 8 1 3 8 2 3 8 3 3 84 3 8 5 3 8 6 3 8 7 3 8 8 3 8 9 3 90 ^¾¾ 3 9 1 3 9 2 3 9 3 OujO 394 6¾¾¾ 3 9 5 3 9 6 ^0^0% 3 9 7 3 9 8 3 9 9 400 29 321062 200948929 4 0 1 O^Pn^O o^o 40 2 4 0 3 404 秦 4 0 5 406 4 0 7 cuo 4 0 8 4 0 9 4 10 °Μ〇^ 4 11 4 12 4 13 4 14 4 15 CH3^〇i^ 4 16 4 17 4 18 4 19 (9^0 4 2 0 〇%〇^1，28 321062 200948929 〇❹ 3 8 1 3 8 2 3 8 3 3 84 3 8 5 3 8 6 3 8 7 3 8 8 3 8 9 3 90 ^3⁄43⁄4 3 9 1 3 9 2 3 9 3 OujO 394 63⁄43⁄43⁄4 3 9 5 3 9 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 9 4 10 °Μ〇^ 4 11 4 12 4 13 4 14 4 15 CH3^〇i^ 4 16 4 17 4 18 4 19 (9^0 4 2 0 〇%〇^1,

30 321062 200948929 421 〇LV〇 CHi5^¥〇 4 2 2 CH3^〇^> 423 4 2 4 4 2 5 4 2 6 4 2 7 4 2 8 ch3-o doh3 4 2 9 430 4 3 1 4 3 2 4 3 3 CHfcks 434 4 3 5 34 6 4 3 7 4 3 8 4 3 9 440 由一般式[1]所表示之化合物群，可藉由一般所知的 方法來製得，可經由例如以4-溴苯甲醯基溴甲烷、與4’ 31 321062 200948929 溴苯乙酮等為起始原料，經過2至3階段的反應而製得（例 如有下列所記載者：Synthesis，200G，1259、Organic Syntheses, Coll. Vol. 10, 418 > Synthesis, 1982, 1061 > The Journal of Organic Chemistry, 2007, Vol. 72, 6901-6904'The Journal of Organic Chemistry, 2003, Vol. 68, 5392-5394 ' Journal of Medicinal Chemistry, Vol. 44，3838等）。以下係舉出反應例，但本發明並不限定於 此030 321062 200948929 421 〇LV〇CHi5^¥〇4 2 2 CH3^〇^> 423 4 2 4 4 2 5 4 2 6 4 2 7 4 2 8 ch3-o doh3 4 2 9 430 4 3 1 4 3 2 4 3 3 CHfcks 434 4 3 5 34 6 4 3 7 4 3 8 4 3 9 440 The group of compounds represented by the general formula [1] can be obtained by a generally known method, for example, by 4- Bromobenzyl bromide, prepared as a starting material with 4' 31 321062 200948929 bromoacetophenone, etc., after 2 to 3 stages of reaction (for example, the following are listed: Synthesis, 200G, 1259, Organic Syntheses, Coll. Vol. 10, 418 > Synthesis, 1982, 1061 > The Journal of Organic Chemistry, 2007, Vol. 72, 6901-6904 'The Journal of Organic Chemistry, 2003, Vol. 68, 5392-5394 ' Journal of Medicinal Chemistry, Vol. 44, 3838, etc.). The reaction examples are given below, but the present invention is not limited to this.

接下來說明可使用本發明之有機EL元件用材料而製 作出之有機EL元件。Next, an organic EL device which can be produced by using the material for an organic EL device of the present invention will be described.

有機EL元件，係由在陽極與陰極間形成一層或多層 的有機層而成之元件所構成，在此，所謂的一層型有機EL 32 321062 200948929 元件，是指在陽極與陰極間僅由發光層所形成之元件。另 一方面，所諝的多層型有機EL元件，是指除了發光層之 外’為了使電洞或電子谷易注入至發光層、或是使於發光 層内之電洞與電子的再次結合順利地進行之目的，而積層 有電洞注入層、電洞傳輸層、電洞阻止層、電子注入層、 電子傳輸層等而成者。因此，多層型有機EL元件的代表性 元件構成，有以（1)陽極/電洞注入層/發光層/陰極；（2) !%極/電洞注入層/電洞傳輸層/發光層/陰極；（3)陽極/電 © 洞注入層/發光層/電子注入層/陰極；（4)陽極/電洞注入層 /電洞傳輸層/發光層/電子注入層/陰極；陽極/電洞注 入層/發光層/電洞阻止層/電子注入層/陰極；（6)陽極/電 洞注入層/電洞傳輸層/發光層/電洞阻止層/電子注入層/ 陰極；（7)陽極/發光層/電洞阻止層/電子注入層/陰極；(8) 陽極/發光層/電子注入層/陰極；（9)陽極/電洞注入層/電 洞傳輸層/發光層/電子傳輸層/電子注入層/陰極；（1〇)陽 ❹極/電洞注入層/發光層/電洞阻止層/電子傳輸層/電子注 入層/陰極等多層構成積層而成之元件構成。 此外，上述各有機層分別可由雙層以上的層構成所形 成、，也可重複積層有數層。該例子之一，例如有近年來以 取光效率的提升為目的，將上述多層型有機EL元件之一部 分的層予以多層化之稱為「多重光子放射」的元件構成。 此係例如有’在由玻璃基板/陽極/電洞傳輸層/電子傳輸性 發光層/電子注入層/電荷產生層/發光單元/陰極所構成之 有機EL元件中，積層複數屬電荷產生層與發光軍元的部分 321062 33 200948929 之方法。 本發明之有機EL元件用材料，可使用於上述任一層， 但較理想為使用於發光層或電子傳輸層。 發光層可由單獨的材.料所形成，或是由複數種材料所 形成。發光層所使用之材料，除了本發明之有機乩元件甩 材料之外，亦可使用一般所知的發光材料、摻雜材料、電 洞注入材料及電子注入材料。亦可依發光層令所使用之材 料的種類及該組成之不同，而達到發光亮度或發光效率的 提升’或是得到紅色或藍色、綠色等多種發光色^此外， 亦可藉由組合複數種發光材料而獲得白色發光。 可與本發明之有機EL元件用材料一同使用於發光層 之發光材料或摻雜材料，例如有蒽衍生物、蔡衍生物、菲 衍生物、茈衍生物、稠四苯衍生物、蔻衍生物、稠二萘衍 生物、螢光黃衍生物、茈衍生物、欧茈（Phthaloperylene) 衍生物、萘并花（Naphthaloperylene)衍生物、紫環酮衍生 物、酜并周因_ (Phthaloperinone)衍生物、萘并周因S同 (Naphthaloperinone)衍生物、二苯丁二烯衍生物、四苯丁 二烯衍生物、香豆素衍生物、噚二唑衍生物、醛連氮衍生 物、雙苯并卩萼唾琳衍生物、雙苯乙烯衍生物、二酮β比洛並 吡咯衍生物、吡咯甲川衍生物、吡畊衍生物、環戊二烯衍 生物、喹啉金屬錯合物衍生物、二苯伸乙基衍生物、乙婦 蒽衍生物、味嗤衍生物、α辰喃衍生物、嘆喃衍生物、聚次 曱基衍生物、部花青素衍生物、咪唑螯合化類氧化物衍生 物、喹吖啶酮衍生物、紅螢烯衍生物、或是色素雷射用或 34 321062 200948929 增白用的螢光色素等，但並不限定於此β 上述材料中可適當地使用之發光層構成材料， 萘衍生物、蒽衍生物、菲衍生物、芘衍生物、 歹:如有 祠四苯衍生 物、茈衍生物、咔唑衍生物、二酮吡咯並吡咯衍生物、。 咯甲川衍生物、喹啉系金屬錯合物衍生物。 吡 此外，發光層中所能夠使用之發光材料或摻雜材料， 亦可使用磷光發光材料。當組合使用本發明之有機乩元件 ❹用材料與磷光發光材料時，本發明之化合物可用作為發光 層中的主材料。在此所謂的磷光發光材料，係意味著從激 發二重態躍遷至基底狀態時產生發光之化合物。本發明之 有機電場發光元件所能夠使用之磷光發光材料，例如為有 機金屬錯合物。有機金屬錯合物中的金屬原子，_般為過 渡金屬’較理想的對象為週期為第5週期或第6週期，族 為6族至11族，更理想為8族至1〇族之元素。具體而言 有銦和鉑等。此外，配位基有2-苯吡啶或2-(2’ —苯并噻 G 吩基）吡啶等，該特徵為這些配位基上的碳原子直接與金屬 鍵結。其他例子有卟啉或四氮雜卟啉環錯合物等，中心金 屬例如有鉑等。 此外，發光層中，為了擔負起電洞傳輸層或電子傳輸 層的功能，或是為了提升成膜性’可使用高分子。此外， 為了提升成膜性或防止膜的針孔等，可使用抗氧化劑、紫 外線吸收劑、可塑劑。高分子例如有聚苯乙烯、聚碳酸酯、 氟丙烯酸酯、聚酯、聚醯胺、聚胺甲酸酯、聚砜、聚甲基 丙烯酸曱酯、聚丙烯酸曱酯、纖維素等絕緣性樹脂及該等 35 321062 200948929 的共聚物；聚-N-乙烯咔唑、聚矽烷等光導電性樹脂；聚噻 吩、聚°比p各等導電性樹脂。 當發光層使用複數種材料時，各材料的調配比並無特 別限定。此外，將本發明之有機EL元件用材料使用於發光 層時在發光層中的存在比例，並無特別限定。亦即，本發 明之有機EL元件用材料可單獨使用，或是作為主材料或摻 雜劑而使用於發光層。 電洞注入層，係使用對發光層顯現出優異的電洞注入 效果，且可形成與陽極界面之密接性與薄膜形成性優良之 電洞注入層的電洞注入材料。此外，當積層有多層電洞注 入效果高的材料與電洞傳輸效果高的材料來作為此材料 時，有時分別將所使用的材料稱為電洞注入材料、電洞傳 輸材料。此電洞注入材料或電洞傳輸材料的例子，除了本 申請案發明的化合物之外，例如有酞菁衍生物、萘酞菁衍 生物、外琳衍生物、曙二嗤衍生物、三。坐衍生物、咪峻衍 生物、w米β坐酮衍生物、ϋ米唾硫酮衍生物、π比坐琳衍生物、 π比。坐酮衍生物、四氫σ米嗤衍生物、曙β坐衍生物、曙二唾衍 生物、滕衍生物、醯腙衍生物、二苯乙稀衍生物、芳香族 三級胺衍生物等低分子化合物；或聚乙烯咔唑衍生物、聚 矽烷衍生物等高分子化合物，只要可形成元件製作所需的 薄膜，且可從陽極注入電洞並傳輸電洞之材料，則並無特 別限制。 上述材料中可適當地使用之電洞注入材料或電洞傳 輸材料，例如有芳香族三級胺衍生物及駄菁衍生物。芳香 36 321062 200948929 族三級胺衍生物例如有N，r -二苯基-N，N，-(3-甲基苯 基）-1，1’ -聯苯-4,4’ -二胺、N，N，N’，N’ -(4-甲基苯 基）-1，Γ -苯基-4,4’ -二胺、N，N，N’，N’ -(4-曱基苯 基）-1，Γ -聯苯-4,4’ -二胺、N，N’ -二苯基-N，N，-二萘 基-1，Γ -聯苯-4,4’ -二胺、N，N’ -(甲基苯基）-n，N，-(4-正丁基苯基）-菲-9, 10-二胺、N, N-雙（4-二-4-甲苯胺基 苯基）-4-苯基-環己烧’以及具有這些芳香族三級胺骨幹之 低聚物或聚合物’這些均可適用於電洞注入材料及電洞傳 ❹ 輸材料的任一種。此外，駄菁（Pc)衍生物例如有HzPc >The organic EL element is composed of an element in which one or more organic layers are formed between the anode and the cathode. Here, the so-called one-layer organic EL 32 321062 200948929 element means that only the light-emitting layer is between the anode and the cathode. The formed component. On the other hand, the multilayer organic EL device of the present invention means that in addition to the light-emitting layer, 'in order to facilitate the injection of a hole or an electron valley into the light-emitting layer, or to recombine the hole and the electron in the light-emitting layer smoothly. The purpose of the ground is to form a hole injection layer, a hole transport layer, a hole stop layer, an electron injection layer, an electron transport layer, and the like. Therefore, representative elements of the multilayer organic EL device are composed of (1) anode/hole injection layer/light-emitting layer/cathode; (2) !% pole/hole injection layer/hole transmission layer/light-emitting layer/ Cathode; (3) anode/electron injection layer/light-emitting layer/electron injection layer/cathode; (4) anode/hole injection layer/hole transmission layer/light-emitting layer/electron injection layer/cathode; anode/hole Injection layer/light-emitting layer/hole stop layer/electron injection layer/cathode; (6) anode/hole injection layer/hole transport layer/light-emitting layer/hole stop layer/electron injection layer/cathode; (7) anode / luminescent layer / hole blocking layer / electron injection layer / cathode; (8) anode / luminescent layer / electron injection layer / cathode; (9) anode / hole injection layer / hole transmission layer / luminescent layer / electron transport layer /Electron injection layer/cathode; (1〇) an anode/pole injection layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode and the like are composed of a plurality of layers. Further, each of the above organic layers may be formed of a layer of two or more layers, or a plurality of layers may be repeatedly laminated. In one of the examples, for example, in order to improve the light extraction efficiency, a layer of a part of the multilayer organic EL element is referred to as a "multiple photon emission" element. For example, in the organic EL element composed of a glass substrate/anode/hole transport layer/electron light-transmitting light-emitting layer/electron-implanted layer/charge generating layer/light-emitting unit/cathode, the laminated plurality of charge generating layers and The method of illuminating the military element part 3210633 200948929. The material for an organic EL device of the present invention can be used for any of the above layers, but is preferably used for a light-emitting layer or an electron transport layer. The luminescent layer may be formed of a single material or a plurality of materials. As the material used for the light-emitting layer, in addition to the organic germanium element(R) material of the present invention, generally known light-emitting materials, dopant materials, hole injecting materials, and electron injecting materials can be used. According to the type of the material used in the luminescent layer and the difference in the composition, the illuminating brightness or the illuminating efficiency can be improved, or a plurality of illuminating colors such as red or blue or green can be obtained, or by combining plural numbers. A luminescent material is used to obtain white luminescence. It can be used together with the material for an organic EL device of the present invention for a light-emitting material or a dopant material of a light-emitting layer, for example, an anthracene derivative, a Cai derivative, a phenanthrene derivative, an anthracene derivative, a thick tetraphenyl derivative, an anthracene derivative. , fused naphthalene derivative, fluorescent yellow derivative, anthraquinone derivative, Phthaloperylene derivative, Naphthaloperylene derivative, pirinone derivative, Phthaloperinone derivative Naphthaloperinone derivative, diphenylbutadiene derivative, tetraphenylbutadiene derivative, coumarin derivative, oxadiazole derivative, aldehyde nitrogen derivative, bisbenzoate卩萼 琳 衍生物 derivative, bis styrene derivative, diketone β piropyrazole derivative, pyrromethene derivative, pyridinium derivative, cyclopentadiene derivative, quinoline metal complex derivative, two Benzene ethyl ester derivative, ethyl 4-glycoside derivative, miso derivative, α-chen derivative, sulphur derivative, poly-decyl derivative, phthalocyanine derivative, imidazole chelated oxide Derivative, quinacridone derivative, red fluorene derivative For the pigment or laser light, or the fluorescent pigment for whitening, 34 321062 200948929, but not limited to the β light-emitting layer constituent material which can be suitably used in the above materials, naphthalene derivative, anthracene derivative, phenanthrene Derivatives, anthracene derivatives, hydrazine: such as a perylenetetrazine derivative, an anthracene derivative, a carbazole derivative, a diketopyrrolopyrrole derivative. A carbamide derivative or a quinoline metal complex derivative. Pyridine In addition, a phosphorescent material can be used as the light-emitting material or dopant material that can be used in the light-emitting layer. When the organic germanium element of the present invention is used in combination with a phosphorescent material, the compound of the present invention can be used as a main material in the light-emitting layer. The term "phosphorescent luminescent material" as used herein means a compound which emits light upon transition from an excited doublet state to a basal state. The phosphorescent material which can be used in the organic electroluminescence device of the present invention is, for example, an organic metal complex. The metal atom in the organometallic complex, _like a transition metal, is preferably a period of the fifth cycle or the sixth cycle, and the family is a group of 6 to 11 groups, more preferably an element of 8 to 1 group. . Specifically, there are indium, platinum, and the like. Further, the ligand is 2-phenylpyridine or 2-(2'-benzothia G phenyl)pyridine or the like, which is characterized in that the carbon atom on these ligands is directly bonded to the metal. Other examples are porphyrin or tetraazaporphyrin ring complex, and the like, for example, platinum or the like. Further, in the light-emitting layer, a polymer may be used in order to function as a hole transport layer or an electron transport layer or to improve film formability. Further, in order to improve film formability or prevent pinholes or the like of the film, an antioxidant, an ultraviolet absorber, or a plasticizer can be used. Examples of the polymer include insulating resins such as polystyrene, polycarbonate, fluoroacrylate, polyester, polyamine, polyurethane, polysulfone, polymethylmethacrylate, polyacrylic acid acrylate, and cellulose. And the copolymer of 35 321062 200948929; a photoconductive resin such as poly-N-vinylcarbazole or polydecane; a conductive resin such as polythiophene or polypyramidine. When a plurality of materials are used for the light-emitting layer, the compounding ratio of each material is not particularly limited. Further, the ratio of the presence of the material for an organic EL device of the present invention to the light-emitting layer in the light-emitting layer is not particularly limited. That is, the material for an organic EL device of the present invention can be used alone or as a host material or a dopant for the light-emitting layer. The hole injection layer is formed by using a hole injection material which exhibits an excellent hole injection effect on the light-emitting layer and which forms a hole injection layer excellent in adhesion to the anode interface and film formation property. In addition, when a material having a high layer injection effect and a material having a high hole transmission effect is laminated as the material, the materials used may be referred to as a hole injection material or a hole transmission material, respectively. Examples of the hole injecting material or the hole transporting material include, in addition to the compound of the invention of the present application, a phthalocyanine derivative, a naphthalocyanine derivative, a metalin derivative, an anthraquinone derivative, and a third. Sit derivative, imiline derivative, w-m β ketone derivative, glutinous thione derivative, π than sitting derivative, π ratio. Low ketone derivatives, tetrahydrostilbene derivatives, 曙β sit derivatives, guanidine di-saliva derivatives, tensin derivatives, anthracene derivatives, diphenylethylene derivatives, aromatic tertiary amine derivatives, etc. The molecular compound or a polymer compound such as a polyvinyl carbazole derivative or a polydecane derivative is not particularly limited as long as it can form a film required for the production of a device and can inject a hole from the anode and transport the material of the hole. A hole injecting material or a hole transporting material which can be suitably used in the above materials, for example, an aromatic tertiary amine derivative and a phthalocyanine derivative. Aromatic 36 321062 200948929 Group of tertiary amine derivatives such as N,r-diphenyl-N,N,-(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, N,N,N',N'-(4-methylphenyl)-1, fluorene-phenyl-4,4'-diamine, N,N,N',N'-(4-mercaptobenzene -1,Γ-biphenyl-4,4'-diamine, N,N'-diphenyl-N,N,-dinaphthyl-1, fluorene-biphenyl-4,4'-diamine ,N,N'-(methylphenyl)-n,N,-(4-n-butylphenyl)-phenanthrene-9, 10-diamine, N, N-bis(4-di-4-methyl Anilinophenyl)-4-phenyl-cyclohexanol and oligomers or polymers having these aromatic tertiary amine backbones are suitable for use in cavity injection materials and tunneling materials. One. Further, the phthalocyanine (Pc) derivative has, for example, HzPc >

CuPc、CoPc、NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、 ClGaPc、ClInPc、ClSnPc、ChSiPc、（HO)AlPc、（HO)GaPc、 VOPc、TiOPc、MoOPc、GaPc-〇-GaPc 等酞菁衍生物’這些 尤其適用於電洞注入材料。 電子注入層及電子傳輸層，係使用分別對發光層顯現 出優異的電子注入效果、電子傳輸效果，且形成與陰極 ❹界面之密接性與薄膜形成性優良之電子注入層的電子注入 材料。此電子注入材料的例子，除了本發明的牝舍物之外， 例如有金屬錯合物、含氮五員環衍生物、芴醐衍生物、蒽 醌二甲烷衍生物、聯苯醌衍生物、二氧化噻喃衍生物、茈 四羧酸衍生物、亞芴曱烷衍生物、蒽酮衍生物、矽雜裱戊 二烯衍生物、乙醯丙酮鈣、醋酸鈉等❶此外，邡有將铯等 金屬摻雜於紅二苯基啡啉而成之無機/有機複舍讨斜或 BCP、TPP、T5MPyTZ等，作為電子注入材料的例孑（高分子 學會預稿集，第50卷，4號’ 66〇頁，2〇〇1枣、第50次 .321062 37 200948929 應用物理學朗會演講觀集， 2_年)。只要為可形成元件製作所需的薄膜3，；術頁， 極注入電子並傳輪雷工+以" 守騰’且可從陰 上述電子料’則並無特別限制。 上这電子“材料1子傳輸材料巾 材料，例如有本發明的化合物、金屬錯合物或含、 衍生：。本發明中所能夠使用之電子注入材料= ⑽屬錯合物’例如有參（8—祕州銘、參（2_甲基: I基啥琳）18、參（5-苯基♦祕料）銘、雙經^啥 啉）（1-萘紛）铭、雙(8，基喧琳）（2_萘盼化、雙⑻經基 啥琳X苯紛）銘、雙（8一經基啥琳)(4一氰基一卜萘紛）紹、雙 (4-甲基-8-羥基喹啉）（卜萘酚）鋁、雙（5_甲基_8_羥基喹 琳）（2-萘酚）鋁、雙（5-苯基~8_羥基啥琳）（苯紛）铭、雙（5_ 氰基-8-輕基啥琳）（4-氰基-1-萘盼）紹、雙（8_經基喧琳） 氯銘、雙（8-經基喧琳）（鄰甲紛）銘等銘錯合物；參（8_經基 喹啉）鎵、參（2-曱基-8-羥基喹啉）鎵、參（2-曱基-5-苯基 〇 -8-羥基喹淋）鎵、雙（2-甲基-8-羥基嗤琳）（1-萘盼）鎵、雙 (2-甲基-8-羥基喹啉）（2-萘酚）鎵、雙（2-曱基-8-羥基喹 啉）（苯酚）鎵、雙（2-甲基-8-羥基喹啉）（4-氰基-1-萘酚） 鎵、雙（2, 4_二甲基_8-羥基喹啉）（1一萘酚）鎵、雙（2, 5-二 曱基-8-羥基喹啉）（2-萘酚）鎵、雙（2-曱基-5-苯基-8-羥基 喹嘛）（苯酴）鎵、雙（2-甲基-5-氰基-8-經基噎琳）（4-氰基 -1-萘酚）鎵、雙（2-曱基-8-羥基喹啉）氯鎵、雙（2-甲基-8-羥基喹啉）（鄰曱酚）鎵等鎵錯合物；此外更有8-羥基喹啉 鋰、雙（8-羥基喹啉）銅、雙（8-羥基喹啉）錳、雙（10-羥基 38’ 321062 200948929 苯并[h]喹啉）鈹、雙（8__鞀 啥们鋅等金屬錯合物。基唆琳）鋅、雙（1〇_經基苯并[h] 相的:i卜五一明中所能约使用之電子注入材料中’較理 想的含氮五貝環衍生物，例 俨-4^、-上此 例如有％唑衍生物、噻唑衍生物、 %—唑知生物、噻二唑衍生一 例如有2,5-雙（卜苯基^ 三唾衍生物。具體而言’ ! q . ^ ^ 0 p 1’3,4~'噚唑、2,5-雙（1-苯基）- ❹ 級丁基苯基）-5-(4” -聯 , q ^ ^ ~ ,聊本)〜丨，3,4-噚二唑、2,5-雙（1-萘 2 [2 r5, - 丨’4—雙[2—(5~苯基Pf 二峻基）]苯、1，4~ 4、二級丁基苯]、2-(4’ -三級丁 基本基）-5-(4” -聯笨）4 q i，m哇、u-雙[2’广嗟二吃、2,5_雙（1_寮基）' C 2〜（5~苯基噻二唑基）]苯、2-(4’ ~ -級丁基本基)-5-(4、聯笨 基M，3, 4-三唑、]4錐r ，3, 4_二唑、2,卜雙（1_萘 ϋ _ ，雙[2~(5-苯基三唑基）]苯等。 再者，電洞阻止層，往a m ❹ 到達至電子、、主入展，n糸使用可防止經過發光層之電洞 可形成薄膜形成性優良之層的電洞 苯基苯紛）料㈣合物^ ’例如有雙（8_祕喧琳）（4-苯盼）鎵等鎵錯合物；2 9 (2m祕喹似4_苯基 (簡等含氮縮合料^基-4,7—二苯基―1，1G-啡琳 此外，本發明之有棬 例如有碳、链、鈒、鐵1件的陽極中所使用之材料， 金屬及其合金;氧化鋅、，、錦、鶴、銀、金、始、把等 等導電性金屬氧化物；聚窠匕锡、氧化姻、氧化銦錫（IT0) 眾塞吩、聚吡咯、聚苯胺等導電性 321062 39 200948929 聚合物等。尤其是本發明之有機乩元件的陽極中所使用之 導電性材料，較理想為使用電阻值盡可能低者，較佳為Ιτ〇 玻璃、NESA玻璃。 此外，本發明之有機EL元件的陰極中所使用之材料， 只要是可有效率地將電子注人至有機EL元件之材料，則無 特別限定，-般例如為鉑、金、銀、銅、鐵、錫、鋅、鋁‘、: 铜、鉻、鐘、納、鉀、舞、鎮及這些金屬的合金。在此， 代表性的合金例如有翁/銀、鎂/銦、鐘/料，較理想為包 含鐘、納、身、約、鎂等低功函數金屬的合金。此外，亦 可使用如氟化鱗無機鹽來取代上述低功函數金屬。此 外’运些陰極的製作方法，可藉由電阻加熱、電子束加熱、 濺鐘、離子蒸鑛、㈣法㈣界巾—般所知的方法來製作。 述之陽極及陰極，可依需要，藉由雙層以上的構成 災开4 w。 1為了有效率地從本發明之有機EL元件取光，取光3 ==較理想為充分透明。具體而言，元件所發 二有一般為_上，㈣ 者，則無特別限ΐ 機械及熱強度，並且為透 聚乙稀、聚‘=除了玻璃之外’亦推薦可使 此外，本發等透明性聚合物。 運用真空蒸鍍機虹70件之各層的形成方法’月 式成膜法、戈是旋轉=射二鍍:電漿、離子蒸鍍等， 之任一種方法。褥塗佈、浸潰、流動塗佈等濕式成膜: 層的膜厚並無特別限定，若臈厚太厚 321062 40 200948929 則為了獲#力的光輪出而需施加較大電壓，因而導致效 率的惡化，相反的，甚厘太蓮 右膜厚太薄，則會產生針孔等，即使 施加電場，亦難以寐卢&八&H Α 乂筏侍充分的發先焭度。因此，各層的膜 厚較理想為lnm至]"m s .Β Λ 王上的辄圍’更理想為ι〇ηιη至o.zym 的範圍。 此外，為了提升有機EL元件對溫度、濕度、環境之 安定性，可於元件的表面設置保護層，或是藉由樹脂等將 元件全體予以覆蓋或密封。尤其當將元件全體予以覆蓋或 达、封時’較理想為使用可藉由光而硬化之光硬化性樹脂。 如上所述，本有機乩元件，可以低驅動電壓顯現出 尚色純度及凴度。因此’本有機肌元件可運用在壁掛式電 視等平面顯示器或平面發光體，並且可運用在影印機和印 表機等的光源，液晶顯示器或量測儀器類的光源，以及顯 示板、標誌燈等。 為了說明本申請案發明，而於上述引用各種刊物，但 φ 將刊物中所揭示之事項明確地將全體編入於本說明書中。 實施例 首先’在實施例之前，先說明本發明之有機EL元件 用材料的合成例。 (1,4-二酮的合成） (合成例1)中間體1的合成 將氯化鋅（32. 69g)、曱苯（lOOmL)、二乙基胺 (13.16g)、三級丁醇（13. 33g)放入至200mL的燒瓶中，於 氮氣環境下，於室溫中攪拌3小時。將4-溴苯曱醯基溴甲 41 321062 200948929 烷（21.82g)、4’ -溴苯乙酮（10.41g)添加於其中，於室溫 中再攪拌4天。將反應液注入於5重量％硫酸水溶液並擾 拌30分鐘，濾取淡黃色析出物，以水及曱醇洗淨後進行減 壓乾燥（4(TC、1晚），而製得中間體1(15. 66g)。EI-MS (THERMO ELECTRON 公司製 Polaris Q)m/z(分子量測定 值、以下相同）=394、396、398(分子量（從分子式所計算之 理論值、以下相同）：396)。Phthalocyanine derivatives such as CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, ChSiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPc-〇-GaPc 'These are especially suitable for hole injection materials. In the electron injecting layer and the electron transporting layer, an electron injecting material which exhibits an excellent electron injecting effect and electron transporting effect to the light emitting layer and which forms an electron injecting layer excellent in adhesion to the cathode and thin film formation is used. Examples of the electron injecting material include, in addition to the present invention, a metal complex, a nitrogen-containing five-membered ring derivative, an anthracene derivative, a quinodimethane derivative, a biphenyl hydrazine derivative, a thiopyran derivative, a ruthenium tetracarboxylic acid derivative, a decylene derivative, an anthrone derivative, a decyl pentadiene derivative, a calcium acetonate, a sodium acetate, etc. An inorganic/organic complex or a BCP, TPP, T5MPyTZ, etc., which is doped with a red diphenylmorpholine, as an example of an electron injecting material (Preface of Polymer Society, Vol. 50, No. 4) '66 〇 page, 2 〇〇 1 jujube, 50th. 32,062, 37, 2009, 29, 29, 29, 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 As long as the film 3 required for the formation of the element can be formed, there is no particular limitation on the page, the injection of electrons into the pole, and the transfer of the laser to the "Shou Teng' and the above-mentioned electronic material. The electron "material 1 sub-transport material towel material, for example, the compound of the present invention, the metal complex or the inclusion, derivatization: the electron injecting material which can be used in the present invention = (10) is a complex compound, for example, has a reference ( 8—Muzhou Ming, Shen (2_Methyl: I), 18, ginseng (5-phenyl ♦ secret material) Ming, double Jing ^ porphyrin) (1-naphthalene) Ming, double (8,基喧琳)(2_naphthalene, double (8) by 啥琳琳X benzene) Ming, double (8 经 基啥琳) (4-cyano-naphthalene) Shao, bis (4-methyl- 8-hydroxyquinoline (p-naphthol) aluminum, bis(5-methyl-8-hydroxyquinolin) (2-naphthol) aluminum, bis(5-phenyl~8-hydroxyindole) ) Ming, bis (5_ cyano-8-light 啥 啥 )) (4-cyano-1-naphthalene) Shao, double (8_ by Ji Yulin) Chlormine, double (8-Jin Jilin) (Neighboring A) Ming and other complexes; ginseng (8-pyridylquinoline) gallium, ginseng (2-mercapto-8-hydroxyquinoline) gallium, ginseng (2-mercapto-5-phenylindole) -8-hydroxyquinoline gallium, bis(2-methyl-8-hydroxyphthalocyanine) (1-naphthalene) gallium, bis(2-methyl-8-hydroxyquinoline) (2-naphthol) gallium Double (2-mercapto-8-) (quinoquinoline) (phenol) gallium, bis(2-methyl-8-hydroxyquinoline) (4-cyano-1-naphthol) gallium, bis(2,4-dimethyl-7-hydroxyquinoline (1-naphthol) gallium, bis(2,5-didecyl-8-hydroxyquinoline) (2-naphthol) gallium, bis(2-mercapto-5-phenyl-8-hydroxyquina )(phenyl hydrazine) gallium, bis(2-methyl-5-cyano-8-carbyl) (4-cyano-1-naphthol) gallium, bis(2-mercapto-8-hydroxyquine) a gallium complex such as chlorogallium or bis(2-methyl-8-hydroxyquinoline) (o-nonylphenol) gallium; in addition, lithium quinolate, bis(8-hydroxyquinoline) copper, Bis(8-hydroxyquinoline) manganese, bis(10-hydroxy 38' 321062 200948929 benzo[h]quinoline) fluorene, bis (8__ 鼗啥 Zn, etc. metal complex) (1〇_Phenylbenzo[h] phase: ibu Wuyiming, the most suitable nitrogen-containing pentylene ring derivative in the electron injecting material, 俨-4^,- For example, a % azole derivative, a thiazole derivative, a %-azole, or a thiadiazole-derived one has, for example, a 2,5-bis(p-phenyl^tris-salt derivative. Specifically, '!q.^^0p 1'3,4~' carbazole 2,5-bis(1-phenyl)-fluorene-tert-butylphenyl)-5-(4"-linked, q ^ ^ ~ , 聊本)~丨, 3,4-oxadiazole, 2,5 - bis (1-naphthalene 2 [2 r5, - 丨'4-bis[2-(5-phenyl Pf dih-yl)]benzene, 1,4~4, butylbenzene], 2-(4 '-Triple butyl base>-5-(4"-linked stupid) 4 qi,m wow, u-double [2' 嗟2 eaten, 2,5_double (1_寮 base)' C 2~ (5~phenylthiadiazolyl)]benzene, 2-(4'~-butylidene)-5-(4, phenylidene M,3,4-triazole,]4 cone r, 3, 4_diazole, 2, bis (1_naphthoquinone _, bis[2~(5-phenyltriazolyl))benzene, and the like. Furthermore, the hole blocking layer reaches the electrons and reaches the exhibition, and the hole phenylbenzene material (4) which can prevent the formation of a film having excellent film formation through the holes of the light-emitting layer is used. The substance ^' has, for example, a gallium complex such as bis (8_ 喧 喧 琳) (4-phenylpan) gallium; 2 9 (2m quinine like 4 phenyl) (simple nitrogen-containing condensate ^ base-4, 7 -diphenyl-1,1G-morphine In addition, the present invention has materials such as carbon, chain, bismuth, and iron used in an anode, metal and alloy thereof; zinc oxide, brocade, and crane Conductive metal oxides such as silver, gold, ruthenium, etc.; polyfluorene tin, oxidized sulphur, indium tin oxide (IT0), public phenophene, polypyrrole, polyaniline, etc. 321062 39 200948929 Polymer, etc. The conductive material used in the anode of the organic tantalum element of the present invention is preferably one having a resistance value as low as possible, preferably Ιτ〇 glass or NESA glass. Further, in the cathode of the organic EL element of the present invention The material to be used is not particularly limited as long as it can efficiently inject electrons into the organic EL element. Platinum, gold, silver, copper, iron, tin, zinc, aluminum', copper, chromium, bell, nano, potassium, dance, town, and alloys of these metals. Here, representative alloys such as Weng/Silver , magnesium/indium, clock/material, preferably an alloy containing a low work function metal such as a bell, nano, body, about, or magnesium. In addition, a fluorinated scale inorganic salt may be used instead of the above low work function metal. 'The method of making these cathodes can be made by the methods known as resistance heating, electron beam heating, splashing clock, ion-steaming, (4) method (4). The anode and cathode can be borrowed as needed. In order to efficiently take light from the organic EL element of the present invention, the light taking 3 == is preferably sufficiently transparent. Specifically, the element is generally _ (4), there is no special limitation on mechanical and thermal strength, and it is a transparent polymer that is made of polyvinylidene, poly '= except glass'. It is also recommended to use a transparent polymer such as this one. Forming method of each layer of the piece 'monthly film forming method, Ge is rotating = shot two plating: plasma, ion Any one of methods such as vapor deposition, wet coating such as coating, dipping, and flow coating: The film thickness of the layer is not particularly limited, and if the thickness is too thick, 3210640 200948929, in order to obtain the light of the force However, a large voltage is required, which leads to deterioration of efficiency. On the contrary, even if the right film thickness is too thin, pinholes and the like are generated, and even if an electric field is applied, it is difficult to lick Lu &&& H Α 乂筏Therefore, the film thickness of each layer is ideally 1 nm to]"ms.Β Λ Λ 上 Λ Λ ' ' ' ' Λ Λ Λ Λ Λ 。 。 。 。 。 。 。 。 。 。 。 。 。 The stability of the EL element to temperature, humidity, and environment may be provided with a protective layer on the surface of the element, or the entire element may be covered or sealed by a resin or the like. In particular, when the entire element is covered or sealed, it is preferable to use a photocurable resin which can be cured by light. As described above, the organic germanium element can exhibit a color purity and a low temperature at a low driving voltage. Therefore, the organic muscle element can be applied to a flat panel display such as a wall-mounted television or a flat illuminator, and can be applied to a light source such as a photocopier and a printer, a light source of a liquid crystal display or a measuring instrument, and a display panel and a marker light. Wait. In order to explain the invention of the present application, various publications are cited above, but the matters disclosed in the publication are expressly incorporated in the specification. EXAMPLES First, a synthesis example of a material for an organic EL device of the present invention will be described before the examples. (Synthesis of 1,4-diketone) (Synthesis Example 1) Synthesis of Intermediate 1 Zinc chloride (32.69 g), toluene (100 mL), diethylamine (13.16 g), and tertiary butanol ( 13. 33 g) was placed in a 200 mL flask and stirred at room temperature for 3 hours under a nitrogen atmosphere. 4-Bromobenzoyl bromide 41 321062 200948929 alkane (21.82 g) and 4'-bromoacetophenone (10.41 g) were added thereto, and stirred at room temperature for further 4 days. The reaction solution was poured into a 5 wt% sulfuric acid aqueous solution and scrambled for 30 minutes, and the pale yellow precipitate was collected by filtration, washed with water and methanol, and dried under reduced pressure (4 (TC, 1 night)) to obtain Intermediate 1 (15. 66g). EI-MS (Polaris Q manufactured by THERMO ELECTRON Co., Ltd.) m/z (molecular weight measurement value, the same applies hereinafter) = 394, 396, 398 (molecular weight (theoretical value calculated from the molecular formula, the same applies hereinafter): 396 ).

(合成例2)中間體2的合成 於合成例1中使用苯乙酮（6. 29g)來取代4’ _演笨乙 酮並進行相同反應，而製得中間體2(11. 〇4g；)。Ei__Ms m/z=316、318(分子量：317)。(Synthesis Example 2) Synthesis of Intermediate 2 In Synthesis Example 1, acetophenone (6.99 g) was used in place of 4'-phenoacetone and the same reaction was carried out to obtain Intermediate 2 (11. 4 g; ). Ei__Ms m/z = 316, 318 (molecular weight: 317).

(合成例3)中間體3的合成 於合成例1中使用卜乙酿基-4-溴萘（l3〇4g)來取代 4’ -溴苯乙酮並進行相同反應，而製得中間體3 (15· 91g)。EI-MS ra/z=444、446、448(分子量：446) 321062 42 200948929(Synthesis Example 3) Synthesis of Intermediate 3 In Synthesis Example 1, an ethylidene-4-bromonaphthalene (l3〇4g) was used in place of 4'-bromoacetophenone and the same reaction was carried out to obtain an intermediate 3 (15·91g). EI-MS ra/z=444, 446, 448 (molecular weight: 446) 321062 42 200948929

中間體3 (合成例4)中間體4的合成 於合成例1中使用丨〜乙醯基-4-溴萘（13. 04g)來取代 4’ -溴苯乙酮’使用乙醯萘（25 75g)來取代 © 4-溴苯曱酿基溴甲烧並進行相同反應，而製得中間體 4(19. 48g)。EI-MS m/z=494、496、498(分子量：496)。Intermediate 3 (Synthesis Example 4) Synthesis of Intermediate 4 In Synthesis Example 1, hydrazine-acetamido-4-bromonaphthalene (13.04 g) was used instead of 4'-bromoacetophenone. The intermediate 4 (19.48 g) was obtained by substituting <RTIgt; EI-MS m/z = 494, 496, 498 (molecular weight: 496).

中間艘4 ^ (合成例5)中間體5的合成 於合成例1中使用4，-氯苯乙酮（8. 〇9g)來取代4, 溴苯乙酮並進行相同反應，而製得中間體5(1 L89S)。 EI-MS m/z=350、352(分子量：352)。Intermediate 4 ^ (Synthesis Example 5) Synthesis of Intermediate 5 In Synthesis Example 1, 4,-chloroacetophenone (8. 9 g) was used in place of 4, bromoacetophenone and the same reaction was carried out to prepare an intermediate Body 5 (1 L89S). EI-MS m/z = 350, 352 (molecular weight: 352).

(合成例6)中間體6的合成 43 321062 200948929 於合成例1中使用3’ -溴苯乙酮（10.41g)來取代 4’ -溴苯乙酮並進行相同反應，而製得中間體6 (13. 46g)。EI-MS m/z=394、396、398(分子量：396)'(Synthesis Example 6) Synthesis of Intermediate 6 43 321062 200948929 In the Synthesis Example 1, 3'-bromoacetophenone (10.41 g) was used in place of 4'-bromoacetophenone and the same reaction was carried out to obtain Intermediate 6 (13. 46g). EI-MS m/z = 394, 396, 398 (molecular weight: 396)'

BrBr

中間體6 (合成例7)中間體7的合成 於合成例1中使用2-乙醯菲（11. 52g)來取代4’ -溴 苯乙酮並進行相同反應，而製得中間體7(11. 47g)。EI-MS m/z=416、418(分子量：417)。Intermediate 6 (Synthesis Example 7) Synthesis of Intermediate 7 In Synthesis Example 1, 2-ethyl phenanthrene (11.52 g) was used in place of 4'-bromoacetophenone and the same reaction was carried out to obtain Intermediate 7 ( 11. 47g). EI-MS m/z = 416, 418 (molecular weight: 417).

Br 中間體7 (合成例8)中間體8的合成 於合成例1中使用9-乙醯菲（11. 52g)來取代4’ -溴 苯乙酮並進行相同反應，而製得中間體8(10. 04g)。EI-MS m/z=416、418(分子量：417)。 44 321062 200948929Br Intermediate 7 (Synthesis Example 8) Synthesis of Intermediate 8 In Synthesis Example 1, 9-ethyl phenanthrene (11. 52 g) was used in place of 4'-bromoacetophenone and the same reaction was carried out to obtain Intermediate 8 (10. 04g). EI-MS m/z = 416, 418 (molecular weight: 417). 44 321062 200948929

(環化反應） (合成例9)中間體9的合成 將中間體 1(10· 00g)、魯森試劑（Lawesson’ s Reagent) ❾ （11. 9〇g)、曱苯（lOOmL)放入至300mL的燒瓶中，於氮氣環 境下進行3. 5小時的加熱回流。將反應液冷卻至室溫後， 濾取白色析出物。將此析出物於曱醇（100mL)中攪拌1小時 後，濾取白色固體並進行減壓乾燥（40°C、1晚）’而製得 中間體 9(7. 79g)。EI-MS m/z=392、394、396(分子量：394)。(cyclization reaction) (Synthesis Example 9) Synthesis of Intermediate 9 Intermediate 1 (10·00 g), Lawesson's Reagent 11 (11.9 〇g), and toluene (100 mL) were placed. The mixture was heated under reflux for 3.5 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, a white precipitate was collected by filtration. The precipitate was stirred in decyl alcohol (100 mL) for 1 hour, and then a white solid was filtered and dried under reduced pressure (40 ° C, 1 night) to afford Intermediate 9 (7. 79 g). EI-MS m/z = 392, 394, 396 (molecular weight: 394).

(合成例10)中間體的合成 於合成例9中使用中間體2(8. 0〇g)來取代中間體1並 進行相同反應’而製得中間體10(5. 87g) ° EI〜MS m/z=314、 316(分子量：315)。(Synthesis Example 10) Synthesis of Intermediate In Intermediate Example 9, Intermediate 2 (8.0 g) was used instead of Intermediate 1 and the same reaction was carried out to obtain Intermediate 10 (5. 87 g) ° EI~MS m/z = 314, 316 (molecular weight: 315).

(合成例11)中間體11的合成 45 321062 200948929 於合成例9中使用中間體3(11. 26g)來取代中間體1 並進行相同反應，而製得中間體11(8. 64g)。EI-MS m/z=442、444、446(分子量：444)。(Synthesis Example 11) Synthesis of Intermediate 11 45 321062 200948929 Intermediate 3 (11.26 g) was used to give Intermediate 1 (11.26 g). EI-MS m/z = 442, 444, 446 (molecular weight: 444).

(合成例12)中間體12的合成 於合成例9中使用中間體4(12. 53g)來取代中間體1 並進行相同反應，而製得中間體12(10. 54g)。EI-MS m/z=492、494、496(分子量：494)。(Synthesis Example 12) Synthesis of Intermediate 12 Intermediate 12 (12.5 g) was obtained by substituting Intermediate 4 (12. EI-MS m/z = 492, 494, 496 (molecular weight: 494).

Br 中間體12 (合成例13)中間體13的合成 於合成例9中使用中間體5(8. 88g)來取代中間體1並 進行相同反應，而製得中間體13(6. Olg) 〇EI-MS m/z=348、 350(分子量：350)。Br Intermediate 12 (Synthesis Example 13) Synthesis of Intermediate 13 Intermediate 9 (8. 88 g) was used in the synthesis of Example 9 to replace Intermediate 1 and the same reaction was carried out to obtain Intermediate 13 (6. Olg). EI-MS m/z = 348, 350 (molecular weight: 350).

CICI

Br 中問體13 (合成例14)中間體14的合成 於合成例9中使用中間體6(10. 00g)來取代中間體1 46 321062 200948929 並進行相同反應，而製得中間體14(6. 85g)。EI-MS m/z= 392、394、396(分子量：394)。Br Intermediate 13 (Synthesis Example 14) Synthesis of Intermediate 14 In Synthesis Example 9, Intermediate 6 (10. 00 g) was used instead of Intermediate 1 46 321062 200948929 and the same reaction was carried out to obtain Intermediate 14 (6). . 85g). EI-MS m/z = 392, 394, 396 (molecular weight: 394).

(合成例15)中間體15的合成 將中間體l(8.00g)、對曱苯磺酸（4. 23g)、甲苯（lOOmL) ❺ 放入至200mL的燒瓶中，於氮氣環境下進行1小時的加熱 回流。將反應液冷卻至室溫後，濾取白色析出物。將此析 出物於甲苯（50mL)進行再結晶後，進行減壓乾燥（40°C、1 晚）而製得中間體 15(5. 06g)aEI-MSm/z=376、378、380(* 子量：378) 〇(Synthesis Example 15) Synthesis of Intermediate 15 Intermediate 1 (8.00 g), p-toluenesulfonic acid (4.23 g), and toluene (100 mL) were placed in a 200 mL flask and allowed to stand for 1 hour under a nitrogen atmosphere. Heated back. After the reaction solution was cooled to room temperature, a white precipitate was collected by filtration. The precipitate was recrystallized from toluene (50 mL), and dried under reduced pressure (40 ° C, 1 night) to afford Intermediate 15 (5.06 g) aEI-MS m/z = 376, 378, 380 (* Sub-quantity: 378) 〇

(合成例16)中間體16的合成(Synthesis Example 16) Synthesis of Intermediate 16

於合成例15中使用中間體2(6. 41g)來取代中間體i 並進行相同反應’而製得中間體16(5. Olg)。EljS m/z=298、300(分子量：299)。Intermediate 16 (5. Olg) was obtained by substituting Intermediate 2 (6. EljS m/z = 298, 300 (molecular weight: 299).

中間體16 321062 .47 200948929 (合成例17)中間體17的合成 於合成例15中使用中間體3(9. Olg)來取代中間體1 並進行相同反應，而製得中間體17(6. 23g)。EI-MS m/z=426、428、430(分子量：428)。Intermediate 16 321062 .47 200948929 (Synthesis Example 17) Synthesis of Intermediate 17 Intermediate 13 (9.10 g) was used to replace Intermediate 1 in Synthesis Example 15 and the same reaction was carried out to obtain Intermediate 17 (6. 23g). EI-MS m/z = 426, 428, 430 (molecular weight: 428).

Br 中間體17 (合成例18)中間體18的合成 於合成例15中使用中間體4(10. 02g)來取代中間體1 並進行相同反應，而製得中間體18(7. 41g)。EI-MS m/z=476、478、480(分子量：478)。Br Intermediate 17 (Synthesis Example 18) Synthesis of Intermediate 18 Intermediate 14 (10. 02 g) was used to replace Intermediate 1 in Synthesis Example 15 and the same reaction was carried out to give Intermediate 18 ( 7.41 g). EI-MS m/z = 476, 478, 480 (molecular weight: 478).

Br 中間體18 (合成例19)中間體19的合成 於合成例15中使用中間體5(7. 10g)來取代中間體1 並進行相同反應，而製得中間體19(5. 82g)。EI-MS m/z=332、334(分子量：334)。Br Intermediate 18 (Synthesis Example 19) Synthesis of Intermediate 19 Intermediate 19 (7. 10 g) was used to give Intermediate 19 (5. EI-MS m/z = 332, 334 (molecular weight: 334).

Br 中間體19 48 321062 200948929 (合成例20)中間體2〇的合成 於合成例15中使用中間體7(8. 43g)來取代中間體1 並進行相同反應，而製得中間體2〇(7. 13g)。丑卜做 m/z=398、400(分子量：399)。Br intermediate 19 48 321062 200948929 (Synthesis Example 20) Synthesis of intermediate 2 oxime In the synthesis example 15, intermediate 7 (8. 43 g) was used in place of the intermediate 1 and the same reaction was carried out to obtain the intermediate 2 oxime ( 7. 13g). Ugly do m / z = 398, 400 (molecular weight: 399).

〇 (合成例21)中間體21的合成 於合成例15中使用中間體8(8. 43g)來取代中間體j 並進行相同反應，而製得中間體21(6. 94g)。Ei_ms m/z=398、400(分子量：399)。〇 (Synthesis Example 21) Synthesis of Intermediate 21 Intermediate 8 (8.44 g) was obtained by using Intermediate 8 (8. Ei_ms m/z = 398, 400 (molecular weight: 399).

(合成例22)中間體22的合成 將中間體 l(lO.OOg)、甲苯（l〇〇mL)、苯胺（4. 85g)、 對曱苯磺酸（0.45g)添加至200mL的燒瓶中，於氮氣環境下 進行8小時的加熱回流。將反應液冷卻至室溫後，遽取析 出物。將所得之過濾物以甲苯（400mL)進行再結晶而製得中 間體22(9,01运）。£1-18111/2=451、453、455(分子量：453)。 321062 •49 200948929(Synthesis Example 22) Synthesis of Intermediate 22 Intermediate 1 (1.00 g), toluene (1 mL), aniline (4.85 g), p-toluenesulfonic acid (0.45 g) was added to a 200 mL flask. The mixture was heated under reflux for 8 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, the precipitate was taken. The obtained filtrate was recrystallized from toluene (400 mL) to give Intermediate 22 (9,01). £1-18111/2 = 451, 453, 455 (molecular weight: 453). 321062 •49 200948929

(合成例23)中間體23的合成 於合成例22中使用卜萘胺（7. 23g)來取代苯胺並進行 相同反應，而製得中間體23(10. 8g)°EI-MSm/z=5(H、503、 505(分子量：503)。(Synthesis Example 23) Synthesis of Intermediate 23 In Synthesis Example 22, phthalamide (7.23 g) was used to substitute aniline and the same reaction was carried out to obtain Intermediate 23 (10.8 g) °EI-MSm/z = 5 (H, 503, 505 (molecular weight: 503).

Br 中間體23 (合成例24)中間體24的合成 於合成例22中使用中間體2(8. Olg)來取代中間體1 並進行相同反應，而製得中間體24(7. 96g)。EI-MS m/z=373、375(分子量：374)。Br Intermediate 23 (Synthesis Example 24) Synthesis of Intermediate 24 Intermediate 2 (8. Ol. EI-MS m/z = 373, 375 (molecular weight: 374).

(合成例25)中間體25的合成 於合成例22中使用中間體3(11. 26g)來取代中間體1 並進行相同反應，而製得中間體25(9. 16g)。EI-MS m/z=501、503、505(分子量：503)。 50 321062 200948929(Synthesis Example 25) Synthesis of Intermediate 25 Intermediate 3 (11.26 g) was obtained by using Intermediate 3 (1. EI-MS m/z = 501, 503, 505 (molecular weight: 503). 50 321062 200948929

中間*25Middle *25

(合成例26)中間體26的合成 於合成例22中使用中間體5(8-88它）來取代中間體1 並進行相同反應，而製得中間體26(9. 31g)。EI-MS m/z=407、409(分子量：409)。(Synthesis Example 26) Synthesis of Intermediate 26 Intermediate 25 (9. 31 g) was obtained by using Intermediate 5 (8-88) to substituting Intermediate 1 and carrying out the same reaction. EI-MS m/z = 407, 409 (molecular weight: 409).

CI 中間體26 (合成例27)中間體27的合成 將中間體13(6. 00g)、卜萘酸（4. 42g)、肆（三苯膦） 把（0)_(0. 81g)、曱苯（10〇瓜1)、211碳酸_水溶液（1〇〇1111〇放 入至300mL的燒瓶中，於氮氣環境下，於80t中攪拌5小 時。使反應液冷卻後分離出有機層，以曱苯萃取水層（50mL x3次）。將此與先前的有機層混合，並以硫酸鎂進行乾燥。 滤除乾燥職，將活性碳（3 Gg)加人餘中錢拌】小 時。濾、除雜碳後’將缝予以賴濃㈣得之淡褐色固 體以％己院進行再結晶後，藉由甲苯—甲醇進行再沉澱而 製得中間體27(5，）H,m/z(分子量：396)。 51 321062 200948929CI Intermediate 26 (Synthesis Example 27) Synthesis of Intermediate 27 Intermediate 13 (6.0 g), bnaphthalic acid (4. 42 g), bismuth (triphenylphosphine), (0)_ (0. 81 g), Toluene (10 melon 1), 211 carbonic acid_aqueous solution (1〇〇1111〇) was placed in a 300 mL flask, and stirred under a nitrogen atmosphere for 5 hours at 80 t. After cooling the reaction solution, the organic layer was separated. The aqueous layer was extracted with benzene (50 mL x 3 times). This was mixed with the previous organic layer and dried with magnesium sulfate. The dryness was filtered off, and the activated carbon (3 Gg) was added to the remaining amount of time. After the addition of carbon, the solid brown solid obtained by refining (4) was recrystallized in % hexane, and then reprecipitated by toluene-methanol to obtain intermediate 27 (5,) H, m/z (molecular weight :396). 51 321062 200948929

中間體27 (合成例28)中間體勿的合成 將中間體19(5. 00g)、1-萘堋酸（3. 〇9g)、肆（三苯膦） 把（0)(0. 52g)、曱本（100mL)、2M碳酸卸水溶液（1〇〇此）放 入至300mL的燒瓶中’於氮氣環境下，於8(rc中擾摔3 5 小時。使反應液冷卻後分離出有機層，以甲苯萃取水層 (50mLx3次）。將此與先前的有機層混合，並以硫酸鎂進行 乾燥。濾除乾燥劑後，將活性碳（3. 〇g)加入濾液中並攪拌 1小時。濾除活性碳後，將濾液予以減壓濃縮而得之淡褐 色固體，以環己烷進行再結晶後，藉由甲苯一曱醇進行再沉 澱而製付中間體28(3. 82g)°EI~MS m/z=380(分子量：380)。Intermediate 27 (Synthesis Example 28) Synthesis of intermediates Intermediate 19 (5.0 g), 1-naphthoic acid (3. 9 g), hydrazine (triphenylphosphine) (0) (0.52 g)曱 ( (100mL), 2M aqueous solution of carbonic acid (1 )) was placed in a 300mL flask 'under nitrogen environment, disturbed for 3 5 hours in 8 (rc). After the reaction liquid was cooled, the organic layer was separated. The aqueous layer was extracted with toluene (50 mL×3 times). This was mixed with the previous organic layer and dried over magnesium sulfate. After the desiccant was filtered off, activated carbon (3. g) was added to the filtrate and stirred for 1 hour. After filtering off the activated carbon, the filtrate was concentrated under reduced pressure to give a pale brown solid, which was recrystallized from cyclohexane and then reprecipitated by toluene monoethanol to afford intermediate 28 (3. 82 g) ° EI ~MS m/z = 380 (molecular weight: 380).

(合成例29)中間體29的合成 將中間體26(5. 00g)、1-萘棚酸（3. 16g)、肆（三苯膦） 把（0)(0.712)、曱苯（100虬）、2]^碳酸鉀水溶液（1〇〇1111〇放 入至300mL的燒瓶中，於氮氣環境下，於8〇°c中攪拌5小 時。使反應液冷卻後分離出有機層，以甲苯萃取水層（5〇mL x3次）。將此與先前的有機層混合，並以硫酸鎂進行乾燥。 52 321062 200948929 濾除乾燥劑後，將活性碳（3. 〇g)加入濾液中並攪拌i小 時。濾除活性礙後，將濾液予以減壓濃縮而得之淡褐色固 體，以環己烷進行再結晶後，藉由曱苯_曱醇進行再沉澱而 製知中間體 29(3. 26g)。EI-MS m/z=455(分子量：455)。(Synthesis Example 29) Synthesis of Intermediate 29 Intermediate 26 (5.0 g), 1-naphthalene acid (3. 16 g), hydrazine (triphenylphosphine) (0) (0.712), toluene (100 虬) And 2] potassium carbonate aqueous solution (1〇〇1111〇 was placed in a 300 mL flask, and stirred under a nitrogen atmosphere at 8 ° C for 5 hours. After cooling the reaction solution, the organic layer was separated and extracted with toluene. Water layer (5 〇mL x 3 times). Mix this with the previous organic layer and dry with magnesium sulfate. 52 321062 200948929 After filtering off the desiccant, add activated carbon (3. 〇g) to the filtrate and stir. After the activity was filtered off, the filtrate was concentrated under reduced pressure to give a pale brown solid, which was recrystallized from hexanes, and then reprecipitated by benzene-nonyl alcohol to obtain intermediate 29 (3. EI-MS m/z = 455 (molecular weight: 455).

❹（合成例30)例示化合物1的合成 將中間體9(3. 50g)、1-萘硼酸（2.44g)、肆（三苯膦） 鈀（0)(0. 51g)、甲笨（1〇〇虬）、2M碳酸鉀水溶液（i〇〇mL)放 入至300mL的燒瓶中，於氮氣環境下’於8〇。匚中攪拌5小 時。使反應液冷卻後分離出有機層，以曱苯萃取水層（5〇mL x3次）。將此與先前的有機層混合，並以硫酸鎂進行乾燥。 濾除乾燥劑後，將活性碳X3.6g)加入濾液中並擾拌1小 ❹時。濾除活性碳後，將濾液予以減壓濃縮而得之淡褐色固 體，以環己烷進行再結晶後，藉由甲苯-甲醇進行再沉澱而 製得例示化合物1(2.78琶）。£1-1^111々=488(分子量：488)。 (合成例31)例示化合物2的合成 於合成例30中使用2-萘硼酸（2. 44g)來取代1-萘硼 酸並進行相同反應，而製得例示化合物2(2. 54g)。EI-MS m/z=488(分子量：488)。 (合成例32)例示化合物3的合成 於合成例30中使用9-蒽硼酸（3. 15g)來取代1-萘硼 53 321062 200948929 酸並進行相同反應，而製得例示化合物3(3. 27g)。EI-MS m/z=588(分子量：588)。 (合成例33)例示化合物4的合成 於合成例30中使用苯基_9一蒽硼酸（4. 23g)來取代 1-萘硼酸並進行相同反應，而製得例示化合物4(4. 02g)。 EI-MS m/z=740(分子量：740) ° (合成例34)例示化合物62的合成 於合成例30中使用中間體1〇(2. 80g)來取代中間體9 並進行相同反應’而製得例示化合物62(2. 04幻。EI-MS m/z=362(分子量：362) ° (合成例35)例示化合物63的合成 於合成例30中使用中間體1〇(2. 80g)來取代中間體 9，使用9-蒽硼酸（3. I5g)來取代卜萘硼酸並進行相同反 應，而製得例示化合物63(2.36g)。EI_MS m/z=412(分子 量：412)。 (合成例36)例示化合物64的合成❹ (Synthesis Example 30) exemplification of the synthesis of Compound 1 Intermediate 9 (3.50 g), 1-naphthalene boronic acid (2.44 g), hydrazine (triphenylphosphine) palladium (0) (0. 51 g), and a stupid (1) 〇〇虬), 2M aqueous potassium carbonate solution (i 〇〇 mL) was placed in a 300 mL flask and was at 8 Torr under a nitrogen atmosphere. Stir for 5 hours in the crucible. After cooling the reaction solution, the organic layer was separated, and the aqueous layer was extracted with benzene (5 〇mL x 3 times). This was mixed with the previous organic layer and dried over magnesium sulfate. After filtering off the desiccant, activated carbon X3.6 g) was added to the filtrate and spoiled for 1 hour. After filtering off the activated carbon, the filtrate was concentrated under reduced pressure to give a pale brown solid, which was recrystallised from cyclohexane and then re-precipitated by toluene-methanol to give the compound 1 (2.78 琶). £1-1^111々=488 (molecular weight: 488). (Synthesis Example 31) Synthesis of exemplified compound 2 In the synthesis example 30, 2-naphthaleneboronic acid (2.44 g) was used instead of 1-naphthalene boronic acid and the same reaction was carried out to obtain the exemplified compound 2 (2.44 g). EI-MS m/z = 488 (molecular weight: 488). (Synthesis Example 32) Synthesis of exemplified compound 3 In Synthesis Example 30, 9-indoleboric acid (3.15 g) was used instead of 1-naphthalene boron 53 321062 200948929 acid and the same reaction was carried out to obtain an exemplified compound 3 (3. 27 g). ). EI-MS m/z = 588 (molecular weight: 588). (Synthesis Example 33) Synthesis of exemplified compound 4 In Synthesis Example 30, phenyl-9-boronic acid (4.23 g) was used in place of 1-naphthaleneboronic acid and the same reaction was carried out to obtain an exemplified compound 4 (4.22 g). . EI-MS m/z = 740 (molecular weight: 740) ° (Synthesis Example 34) exemplification of the compound 62 was synthesized in the synthesis example 30 using the intermediate 1 (2. 80 g) instead of the intermediate 9 and carrying out the same reaction' An exemplified compound 62 (2. 04 g) was obtained by the exemplified compound 62 (2. 04 phantom. EI-MS m/z = 362 (molecular weight: 362) ° (Synthesis Example 35) exemplified in Synthesis Example 30. To replace Intermediate 9, 9-indoleboronic acid (3.15 g) was used in place of the naphthalene boronic acid and the same reaction was carried out to obtain the exemplified compound 63 (2.36 g). EI_MS m/z = 412 (molecular weight: 412). Synthesis Example 36) Synthesis of Compound 64

於合成例30中使用中間體l〇(2.8〇g)來取代中間體 9,使用10-苯基-9-蒽硼酸（4.23g)來取代卜萘硼酸並進行 相同反應，而製得例Μ合物64(2· 59g) ° EI'MS m/z=488(分子量：488) ° (合成例37)例示化合物82的合&amp;In the synthesis example 30, the intermediate l (2.8 g) was used instead of the intermediate 9, and 10-phenyl-9-indole boronic acid (4.23 g) was used in place of the naphthalene boronic acid and the same reaction was carried out to prepare an example. Compound 64 (2·59 g) ° EI'MS m/z = 488 (molecular weight: 488) ° (Synthesis Example 37) exemplified compound &amp;

於合成例30中使用中間體U(3, 95g)來取代中間體9 並進行相同反應，而製得例示化合物82(3.3切。EI-MS m/z=538(分子量：538) 321062 54 200948929 (合成例38)例示化合物80的合成 於合成例30中使用中間體Π (3. 95g)來取代中間體 9，使用9-蒽硼酸（3. 15S)來取代1-萘硼酸並進行相同反 應，而製得例示化合物80(3. 70g)。EI-MS m/z=638(分子 量：638) 〇 (合成例39)例示化合物78的合成 於合成例30中使用中間體11 (3. 95g)來取代中間體 9,使用10-苯基-9-慧硼酸（4.23g)來取代1-萘硼酸並進行 〇 相同反應，而製得例示化合物78(4. 13g)。EI~MSm/z=790 (分子量：790)。 (合成例40)例示化合物1〇6的合成Intermediate U (3, 95 g) was used in Synthesis Example 30 in place of Intermediate 9 and the same reaction was carried out to obtain the exemplified compound 82 (3.3 cut. EI-MS m/z = 538 (molecular weight: 538) 321062 54 200948929 (Synthesis Example 38) Synthesis of exemplified compound 80 In the synthesis example 30, the intermediate hydrazine (3.95 g) was used instead of the intermediate 9, and 9-indoleboronic acid (3.15S) was used in place of 1-naphthaleneboronic acid and the same reaction was carried out. An exemplified compound 80 (3.70 g) was obtained. EI-MS m/z = 638 (molecular weight: 638) 〇 (Synthesis Example 39) exemplified by the synthesis of compound 78. In order to replace the intermediate 9, the 10-phenyl-9-bromoboronic acid (4.23 g) was used in place of the 1-naphthalene boronic acid and the same reaction was carried out to obtain the exemplified compound 78 (4.13 g). EI~MSm/z = 790 (molecular weight: 790). (Synthesis Example 40) Synthesis of the compound 1〇6

於合成例30中使用中間體12(4_ 34g)來取代中間體9 並進行相同反應，而製得例示化合物106(3. 47g)。EI-MS m/z=588(分子量：588)。 (合成例41)例示化合物1〇5的合成 ❹ 於合成例30中使用中間體12(4. 34g)來取代中間體 9，使用9-蒽硼酸（3. 15g)來取代1-萘硼酸並進行相同反 應’而製得例示化合物105(3. 97g)。EI-MS m/z=688(分子 量：688)。 (合成例42)例示化合物108的合成 於合成例30中使用中間體12(4. 34g)來取代中間體 9,使用10-苯基-9-蒽领酸（4. 23g)來取代1-萘硼酸並進行 相同反應，而製得例示化合物l〇8(5.46g)。EI-MS m/z=840(分子量：840)。 55 321062 200948929 (合成例43)例示化合物20的合成 將中間體 27(3. 00g)、2-萘硼酸（1. 43g)、THF(100mL)、 氟化鉀（1· 32g)、參（二苯亞甲基丙酮）二鈀（〇)(〇. 69g)、三 -三級丁膦（0· 31g)放入至200mL的燒瓶中，於氮氣環境 下，於室溫中攪拌8小時。將反應液注入至甲醇（3〇〇mL) 中並濾取析出物。將此藉由三氣甲烷-甲醇進行再沉澱雨製. 得例示化合物 20(2. 61g)。EI-MSm/z=488(分子量：488)。 (合成例44)例示化合物23的合成 於合成例43中使用9-蒽硼酸（1. 85g)來取代2-萘硼 ❹ 酸並進行相同反應’而製得例示化合物23(2. 58g)。EI-MS m/z=538(分子量：538)。 (合成例45)例示化合物131的合成 將中間體15(2. 50g)、1-萘硼酸（3. 41g)、肆（三苯膦） 鈀（0)(0. 38g)、曱苯（lOOmL)、2M碳酸鉀水溶液（i〇〇mL)放 入至300mL的燒瓶中，於氮氣環境下，於8〇。〇中攪拌2. 5 小時。使反應液冷卻後分離出有機層，以甲苯萃取水層 (50mLx3次）。將此與先前的有機層混合，並以硫酸鎂進行 〇 乾燥。遽除乾燥劑後’將滤液予以減壓濃縮。將所得之黄 橙色固體溶解於甲苯（150mL)，加入活性碳（3.5g)並攪拌 0.5小時。濾除活性碳後，費時2〇分鐘將甲醇（4〇〇mL)滴 入至;慮液並授拌一晚後，滤取析出物而製得例示化合物 131(1. 79g)。EI-MS m/z=472(分子量：472)。 (合成例46)例示化合物132的合成 於合成例45中使用2-萘硼酸（3. 41g)來取代卜萘硼 321062 56 200948929 酸並進行相同反應，而製得例示化合物132(1.84g) βΙ-MS m/z=472(分子量：472)。 (合成例47)例示化合物133的合成 於合成例45中使用10-笨基-9-蒽硼酸（5. 91g)來取代 1-萘硼酸並進行相同反應，而製得例示化合物133(2. 89g)。 EI-MS m/z=724(分子量：724)。 (合成例48)例示化合物134的合成 於合成例45中使用9-蒽硼酸（4. 40g)來取代1-萘侧 〇 酸並進行相同反應，而製得例示化合物134(2. 77g&gt;EI-MS m/z=572(分子量：572) 〇 (合成例49)例示化合物139的合成 於合成例45中使用9-菲蝴酸（4. 40g)來取代1-萘硼 酸並進行相同反應，而製得例示化合物139(2. 59g&gt;EI-MS m/z=572(分子量：572)。 (合成例50)例示化合物149的合成 q 於合成例45中使用苯并[b]噻吩-2-基硼酸（3. 53g)來 取代1-萘硼酸並進行相同反應，而製得例示化合物149 (2. 27g)。EI-MS m/z=484(分子量：484)。 (合成例51)例示化合物197的合成 於合成例45中使用中間體16(1. 98g)來取代中間體 15，使用10-苯基-9-蒽棚酸（5. 91g)來取代1-萘蝴酸並進 行相同反應，而製得例示化合物197(2. 04g)。EI-MS m/z^ 472(分子量：472)。 (合成例52)例示化合物213的合成 57 321062 200948929 於合成例45中使用中間體17(2.咖）來取代中間體 15，使用9-蒽硼酸（4. 40g)來取代卜萘鑛並進行相同反 應’而製得例示化合物213(3. i2g)。EI_MSm/z=622(分子 量：622)。 (合成例53)例示化合物215的合成 於合成例45中使用中間體17(2. 83g)來取代中間體 15並進行相同反應，而製得例示化合物215(2. 42g)〇EI~MS m/z=522(分子量：522)。 (合成例54)例示化合物242的合成 Ο 於合成例45中使用中間體1 §(3. 16g)來取代中間體 15，使用2-壽领酸（3.41g)來取代丨_萘蝴酸並進行相同反 應，而製得例示化合物242(2.41g)。EI-MSm/z=572(分子 量：572)。 (合成例55)例示化合物247的合成 於合成例45中使用中間體18(3. 16g)來取代中間體 15 ’使用9-惠棚酸（4. 40g)來取代1-蔡侧酸並進行相同反 應’而製得例示化合物247(2. 70g)。El-MS m/z=672(分子 ® 量：672)。 (合成例56)例示化合物218的合成 於合成例45中使用中間體20(2· 64g)來取代中間體 15，使用9-蒽硼酸（4. 40g)來取代1-萘硼酸並進行相同反 應，而製得例示化合物218(2. 26g)。EI-MS m/z=496(分子 量：496)。 (合成例57)例示化合物261的合成 321062 58 200948929 於合成例45中使用中間體21(2· 64g)來取代中間體 15，使用1〇-苯基-9-蒽爛酸（5. 91 g)來取代1-萘蝴酸並進 行相同反應，而製得例示化合物261(3. 42g)。EI-MS m/z= 572(分子量：572)。 (合成例58)例示化合物262的合成 於合成例45中使用中間體21(2. 64g)來取代中間體 15，使用苯并[b]噻吩-2-基硼酸（3. 53g)來取代1-萘硼酸 並進行相同反應，而製得例示化合物262(2. 47g)。EI-MS 〇 m/z=452(分子量：452)。 (合成例59)例示化合物153的合成 將中間體 28(3. 50g)、2-萘硼酸（1. 90g)、THF(lOOmL)、 氟化鉀（1. 60g)、參（二苯亞曱基丙酮）二鈀（0)(0. 42g)、三 -三級丁膦（0. 19g)放入至200mL的燒瓶中，於氮氣環境 下，於室溫中攪拌8小時。將反應液注入至甲醇（300mL) 中並濾取析出物。將此藉由三氯甲烷-曱酵進行再沉澱而製 q 得例示化合物 153(3. 24g) ^EI-MS m/z=472(分子量：472)。 (合成例60)例示化合物156的合成 於合成例59中使用9-蒽硼酸（2. 45g)來取代2-萘硼 酸並進行相同反應，而製得例示化合物156(3. 65g&gt;EI-MS m/z=522(分子量：522)。 (合成例61)例示化合物172的合成 於合成例59中使用苯并[b]噻吩-2-基硼酸（1. 96g) 來取代2-萘硼酸並進行相同反應，而製得例示化合物 172(3. 27g)。EI-MS m/z=478(分子量：478)。 59 321062 200948929 (合成例6 2 )例不化合物3 0 6的合成 將中間體22(3.00g)、1-萘硼酸（3L71g)、肆（三苯膦） 鈀（0)(0. 38g)、甲苯（100mL)、2mol/L 碳酸鉀水溶液（lOOmL) 放入至300mL的燒瓶中，於氮氣環境下，於80°C中攪拌3 小時。使反應液冷卻至室溫後分離出有機層。以三氯甲烷 萃取水層（100mLx3)後，將此與先前的有機層混合。將所得 之有機層，以硫酸鎂進行乾燥後進行活性碳處理’以甲苯 (150mL)進行再結晶而製得例示化合物306(2. 38g)。EI-MS m/z=548(分子量：548)。 ® (合成例6 3)例不化合物3 0 7的合成 於合成例62中使用9-蒽硼酸（2.20g)來取代1-萘硼 酸並進行相同反應，而製得例示化合物307(2. 98g)°EI-MS m/z=647(分子量：647) 〇 (合成例64)例示化合物308的合成 於合成例62中使用10-苯基-9-蒽硼酸（2. 96g)來取代 1-萘硼酸並進行相同反應，而製得例示化合物308 a (3.56g)。EI-MS m/z=799(分子量：799)。 (合成例65)例示化合物309的合成 於合成例62中使用9-菲硼酸（2. 20g)來取代1-萘硼 酸並進行相同反應，而製得例示化合物309(3. 17g)°EI_MS m/z=647(分子量：647)。 (合成例66)例示化合物316的合成 於合成例62中使用N-笨基-3-咔唑硼酸（2. 85g)來取 代1-萘棚酸並進行相同反應，而製得例示化合物316 60 321062 200948929 (2. 64g)。EI-MS m/z=777(分子量：777)。 (合成例6Ό例示化合物327的合成 於合成例62中使用中間體23(3. 33g)來取代中間體 22並進行相同反應，而製得例示化合物327(3. 18g&gt;EI-MS m/z=598(分子量：598)。 (合成例68)例示化合物291的合成 於合成例62中使用中間體24(2,48g)來取代中間體 22並進行相同反應，而製得例示化合物291(1. 98g)»EI-MS ❹ m/z=422(分子量：422)。 (合成例69)例示化合物372的合成 於合成例62中使用中間體25(3. 33g)來取代中間體 22並進行相同反應，而製得例示化合物372(2. 74g&gt;EI-MS m/z=598(分子量：598)。 (合成例70)例示化合物358的合成 將中間體 29(3. 50g)、9-蒽硼酸（2. 56g)、THF(lOOmL)、 ❹ 氟化鉀（1. &amp;〇g)、參（二苯亞甲基丙酮）二鈀（〇)(〇· 35g)、三 -三級丁膦（0. 16g)放入至200mL的燒瓶中，於氮氣環境 下，於室溫中攪拌10小時。將反應液注入至甲醇（300mL) 中並濾取析出物。將此藉由三氯曱烷-曱醇進行再沉澱而製 得例示化合物 358(3. 04g)。EI-MS m/z=597(分子量：597)。 (合成例Ή)例示化合物438的合成 於合成例70中使用1-(4-氯苯基）-4-甲基-1,3, 5-三 苯吡咯（1.96g)來取代中間體29並進行相同反應，而製得 例示化合物 438(1. 46g)。EI-MS m/z=511(分子量：511)。 61 321062 200948929 以下係藉由實施例來說明使用本發明之有機EL元件 用材料之有機EL元件，但本發明並不限定於實施例。實施 例中，、要未特別說明時，混合比均表示重量比。蒸鐘（真 空療鐘）係在lG6TQrr的真空中，在未進行基板的加熱或 冷部U控制的條件下進行。此外，元件的發光特性， 係使用發光it件面積2mmx2mm的有機肛元件來測特性。 實施例1 將α-NPD(下列化合物A)真空蒸鍍於洗淨後之附有 ΙΤ0電極的玻璃板上，而製得膜厚75ηιη的電洞注入層。接 ❹ 著將本發明之例示化合物1予以真空蒸鍍而製得膜厚4〇mn 的發光層。之後將TPBI(下列化合物B)予以真空蒸鍍而製 付膜厚.20ηπι的電子注入層。於其上首先蒸鑛氣化鐘inm， 然後再蒸鍍鋁（Al)150nm來形成電極’而製得有機EL元 件。以發光亮度300(cd/m2)於室溫下對此元件進行定電流 驅動後之色度，為CIECxj)1^0. 15,0.〇9)的藍色發光’發 光效率為3. 4cd/A。此外，ϋ測定出以電流密度12. 5mA/cm2 ❹ 進行驅動時之初期亮度、以及於30 C的環境下連續驅動 100小時後之亮度。結果如第2表所示。Intermediate 12 (4 - 34 g) was used in Synthesis Example 30 instead of Intermediate 9 and the same reaction was carried out to give the title compound 106 ( 3.47 g). EI-MS m/z = 588 (molecular weight: 588). (Synthesis Example 41) exemplification of the synthesis of the compound 1〇5 In the synthesis example 30, the intermediate 12 (4. 34 g) was used instead of the intermediate 9, and 9-indole boronic acid (3.15 g) was used instead of the 1-naphthalene boronic acid. An exemplified compound 105 (3.97 g) was obtained by carrying out the same reaction. EI-MS m/z = 688 (molecular weight: 688). (Synthesis Example 42) Synthesis of the exemplified compound 108 In the synthesis example 30, the intermediate 12 (4. 34 g) was used instead of the intermediate 9, and 10-phenyl-9-fluorene acid (4. 23 g) was used instead of 1- The naphthalene boronic acid was reacted in the same manner to give the exemplified compound 10 (5.46 g). EI-MS m/z = 840 (molecular weight: 840). 55 321062 200948929 (Synthesis Example 43) Synthesis of exemplified compound 20 Intermediate 27 (3.0 g), 2-naphthalene boronic acid (1.43 g), THF (100 mL), potassium fluoride (1·32 g), ginseng (II) Phenylmethylacetone) dipalladium (〇) (〇. 69 g) and tri-tertiary phosphine (0·31 g) were placed in a 200 mL flask, and stirred at room temperature for 8 hours under a nitrogen atmosphere. The reaction solution was poured into methanol (3 mL) and the precipitate was collected by filtration. This was reprecipitated by tri-gas methane-methanol to give the compound 20 ( 2.61 g). EI-MS m/z = 488 (molecular weight: 488). (Synthesis Example 44) Synthesis of exemplified compound 23 Illustrative compound 23 (2. 58 g) was obtained by using 9-indole boronic acid (1.85 g) in the same manner as in Synthesis Example 43 and substituting 2-naphthalene boronic acid and performing the same reaction. EI-MS m/z = 538 (molecular weight: 538). (Synthesis Example 45) Synthesis of exemplified compound 131 Intermediate 15 (2.50 g), 1-naphthaleneboronic acid (3.41 g), hydrazine (triphenylphosphine) palladium (0) (0.38 g), toluene (100 mL) 2M potassium carbonate aqueous solution (i〇〇mL) was placed in a 300 mL flask under a nitrogen atmosphere at 8 Torr. Stir for 2. 5 hours. After the reaction mixture was cooled, the organic layer was separated, and aqueous layer was extracted with toluene (50 mL x 3 times). This was mixed with the previous organic layer and dried with magnesium sulfate. After removing the desiccant, the filtrate was concentrated under reduced pressure. The obtained yellow-orange solid was dissolved in toluene (150 mL), activated carbon (3.5 g) was added and stirred for 0.5 hour. After the activated carbon was filtered off, methanol (4 mL) was added dropwise thereto over a period of 2 minutes; after the mixture was stirred for one night, the precipitate was collected by filtration to give the title compound 131 (1. 79 g). EI-MS m/z = 472 (molecular weight: 472). (Synthesis Example 46) Synthesis of exemplified compound 132 In the synthesis example 45, 2-naphthaleneboronic acid (3.41 g) was used instead of bnaphthalene boron 3210656 200948929 acid and the same reaction was carried out to obtain an exemplified compound 132 (1.84 g) βΙ. - MS m/z = 472 (molecular weight: 472). (Synthesis Example 47) Synthesis of exemplified compound 133 In the synthesis example 45, 10-phenyl-9-indoleboronic acid (5.91 g) was used in place of 1-naphthaleneboronic acid and the same reaction was carried out to obtain the exemplified compound 133 (2. 89g). EI-MS m/z = 724 (molecular weight: 724). (Synthesis Example 48) Synthesis of exemplified compound 134 In the synthesis example 45, 9-anthraceneboronic acid (4. 40 g) was used in place of 1-naphthyl phthalic acid and the same reaction was carried out to obtain an exemplified compound 134 (2. 77 g &gt; EI -MS m/z = 572 (molecular weight: 572) 〇 (Synthesis Example 49) exemplified synthesis of compound 139 In Synthesis Example 45, 9-phenanthic acid (4. 40 g) was used in place of 1-naphthaleneboronic acid and the same reaction was carried out. Thus, exemplified compound 139 (2. 59 g &gt; EI-MS m/z = 572 (molecular weight: 572). (Synthesis Example 50) exemplified the synthesis of compound 149 q Benzene[b]thiophene-2 was used in Synthesis Example 45. - Benzylboronic acid (3.53 g) was used in place of 1-naphthalene boronic acid and the same reaction was carried out to obtain the exemplified compound 149 (2.27 g). EI-MS m/z = 484 (molecular weight: 484). (Synthesis Example 51) Synthesis of exemplified compound 197 In Intermediate Example 45, Intermediate 16 (1.98 g) was used instead of Intermediate 15, and 10-phenyl-9-indole acid (5.91 g) was used in place of 1-naphthalene acid and The same reaction was carried out to obtain the exemplified compound 197 (2. 04 g). EI-MS m/z^ 472 (molecular weight: 472). (Synthesis Example 52) exemplified synthesis of compound 213 57 321062 200948929 Intermediate used in Synthesis Example 45 17 (2. coffee) to come Substituent Intermediate 15, exemplified by using 9-indoleboronic acid (4.40 g) in place of the naphthalene ore and carrying out the same reaction', gave the exemplified compound 213 (3. i2g). EI_MSm/z = 622 (molecular weight: 622). Example 53) Synthesis of exemplified compound 215 In Intermediate 45, Intermediate 17 (2.83 g) was used to replace the intermediate 15 and the same reaction was carried out to obtain the exemplified compound 215 (2.22 g) 〇EI~MS m/z = 522 (molecular weight: 522) (Synthesis Example 54) Synthesis of Compound 242 exemplified In the synthesis of Example 45, Intermediate 1 § (3. 16 g) was used instead of Intermediate 15, and 2-shou acid (3.41 g) was used. The compound 242 (2.41 g) was obtained by substituting hydrazine-naphthalene acid and the same reaction was carried out. EI-MS m/z = 572 (molecular weight: 572). (Synthesis Example 55) Synthesis of Compound 247 was synthesized in Synthesis Example 45 The intermediate compound 18 (3.16 g) was used in place of the intermediate 15' to replace the 1-cai-acid and the same reaction using 9- shed acid (4. 40 g) to obtain the exemplified compound 247 (2.70 g). El-MS m/z = 672 (Molecular Weight: 672). (Synthesis Example 56) Synthesis of exemplified Compound 218 In Intermediate Example 45, Intermediate 20 (2·64 g) was used instead of Intermediate 15, using 9- Boric acid 4. 40g) in place of 1-naphthyl boronic acid and the same reaction, yielding Exemplified Compound 218 (2. 26g). EI-MS m/z = 496 (molecular weight: 496). (Synthesis Example 57) Synthesis of Compound 261 321062 58 200948929 Intermediate 21 (2.66 g) was used in Synthesis Example 45 to replace Intermediate 15 using 1-indole-phenyl-9-calcic acid (5. 91 g The compound 261 (3.42 g) was obtained by substituting 1-naphthalene acid and carrying out the same reaction. EI-MS m/z = 572 (molecular weight: 572). (Synthesis Example 58) Synthesis of exemplified compound 262 In Intermediate Example 45, Intermediate 21 (2. 64 g) was used instead of Intermediate 15 and benzo[b]thiophen-2-ylboronic acid (3.33 g) was used instead. -Naphthaleneboronic acid and the same reaction was carried out to give the compound 262 (2. 47 g). EI-MS 〇 m/z = 452 (molecular weight: 452). (Synthesis Example 59) Synthesis of exemplified compound 153 Intermediate 28 (3. 50 g), 2-naphthalene boronic acid (1. 90 g), THF (100 mL), potassium fluoride (1. 60 g), bis(diphenylarsenazo) The base acetone) dipalladium (0) (0.42 g) and tris-tert-butylphosphine (0.19 g) were placed in a 200 mL flask, and stirred at room temperature for 8 hours under a nitrogen atmosphere. The reaction solution was poured into methanol (300 mL) and the precipitate was collected by filtration. This was obtained by reprecipitation by chloroform-fermentation to give the compound 153 (3. 24 g). EI-MS m/z = 472 (molecular weight: 472). (Synthesis Example 60) Synthesis of exemplified compound 156 In the synthesis example 59, 9-indoleboric acid (2.55 g) was used in place of 2-naphthaleneboronic acid and the same reaction was carried out to obtain the exemplified compound 156 (3. 65 g &gt; EI-MS m/z = 522 (molecular weight: 522) (Synthesis Example 61) Synthesis of exemplified compound 172 In Synthesis Example 59, benzo[b]thiophen-2-ylboronic acid (1.96 g) was used instead of 2-naphthaleneboronic acid. The same reaction was carried out to obtain the exemplified compound 172 (3. 27 g). EI-MS m/z = 478 (molecular weight: 478). 59 321062 200948929 (Synthesis Example 6 2 ) Synthesis of Compound 3 0 6 Intermediate 22 (3.00 g), 1-naphthaleneboronic acid (3L71g), hydrazine (triphenylphosphine) palladium (0) (0.38 g), toluene (100 mL), 2 mol/L potassium carbonate aqueous solution (100 mL), placed in a 300 mL flask The mixture was stirred at 80 ° C for 3 hours under a nitrogen atmosphere, and the organic layer was separated after cooling the reaction mixture to room temperature. After extracting the aqueous layer (100 mL×3) with chloroform, the mixture was mixed with the previous organic layer. The obtained organic layer was dried over magnesium sulfate and subjected to activated carbon treatment to recrystallize with toluene (150 mL) to give the title compound 306 (2. 38 g). EI-MS m/z = 548 Amount: 548). (Synthesis Example 6 3) Synthesis of Compound No. 3 0 7 In Synthesis Example 62, 9-indoleboronic acid (2.20 g) was used in place of 1-naphthaleneboronic acid and the same reaction was carried out to obtain an exemplified compound. 307 (2. 98 g) ° EI-MS m/z = 647 (molecular weight: 647) 〇 (Synthesis Example 64) exemplified synthesis of compound 308. 10-Phenyl-9-indole boronic acid (2. 96 g). The compound 308 a (3.56 g) was obtained by substituting 1-naphthalene boronic acid and the same reaction was carried out. EI-MS m/z = 799 (molecular weight: 799). (Synthesis Example 65) Synthesis of the compound 309 was synthesized. In Example 62, 9-phenanthroic acid (2.20 g) was used in place of 1-naphthalene boronic acid and the same reaction was carried out to obtain the exemplified compound 309 (3.17 g) °EI_MS m/z = 647 (molecular weight: 647). Example 66) Synthesis of exemplified compound 316 In Example 62, N-phenyl-3-oxazole boronic acid (2.85 g) was used in place of 1-naphthalene acid and the same reaction was carried out to obtain an exemplified compound 316 60 321062 200948929 (2. 64g). EI-MS m/z = 777 (molecular weight: 777). (Synthesis Example 6 Ό exemplified Compound 327 was synthesized in Synthesis Example 62 using Intermediate 23 (3.33 g) instead of Intermediate 22 The same reaction, Prepared exemplified compound 327 (3 18g &gt; EI-MS m / z = 598 (molecular weight: 598). (Synthesis Example 68) Synthesis of exemplified compound 291 In Intermediate </RTI> </ RTI> </ RTI> m/z = 422 (molecular weight: 422). (Synthesis Example 69) Synthesis of exemplified compound 372 In Intermediate Example 25, Intermediate 25 (3.33 g) was used instead of Intermediate 22, and the same reaction was carried out to obtain the exemplified compound 372 (2. 74g &gt; EI-MS m/ z = 598 (molecular weight: 598) (Synthesis Example 70) Synthesis of exemplified compound 358 Intermediate 29 (3. 50 g), 9-indoleboronic acid (2.66 g), THF (100 mL), and potassium fluoride (1) . &amp; 〇g), ginseng (diphenylmethyleneacetone) dipalladium (〇) (〇·35g), tri-tertiary phosphine (0.16g) was placed in a 200mL flask under nitrogen The mixture was stirred at room temperature for 10 hours, and the reaction mixture was poured into methanol (300 mL), and the precipitate was collected by filtration, and then reprecipitated by trichloromethane-nonanol to obtain the exemplified compound 358 (3. 04 g) EI-MS m/z = 597 (molecular weight: 597). (Synthesis Example) Synthesis of exemplified compound 438 1-(4-chlorophenyl)-4-methyl-1,3 was used in Synthesis Example 70. 5-triphenylpyrrole (1.96 g) was used in place of the intermediate 29 and the same reaction was carried out to obtain the exemplified compound 438 (1. 46 g). EI-MS m/z = 511 (molecular weight: 511) 61 321062 200948929 The organic EL using the present invention will be described by way of examples. The organic EL device of the material for the device is not limited to the embodiment. In the examples, the mixing ratio indicates the weight ratio unless otherwise specified. The steam clock (vacuum clock) is in a vacuum of lG6TQrr. It was carried out under the condition that the heating of the substrate or the control of the cold portion U was not performed. Further, the light-emitting characteristics of the element were measured using an organic anal element having a light-emitting element area of 2 mm x 2 mm. Example 1 α-NPD (Compound A below) Vacuum evaporation was performed on the washed glass plate with the ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 75 ηη. Next, the exemplified compound 1 of the present invention was vacuum-deposited to obtain a film thickness of 4 〇. a light-emitting layer of mn. Then, TPBI (the following compound B) was vacuum-deposited to prepare an electron injecting layer having a film thickness of .20 ηπ, on which the vaporization clock inm was first vaporized, and then aluminum (Al) 150 nm was evaporated. An organic EL element is formed by forming an electrode. The chromaticity of the element after constant current driving at room temperature with a luminance of 300 (cd/m 2 ) is CIECxj)1^0. 15,0.〇9) The blue luminescence 'luminescence efficiency is 3. 4 cd / A. Further, ϋ measured the initial luminance when the current density was 12.5 mA/cm 2 ❹ and the luminance after continuous driving for 100 hours in an environment of 30 C. The results are shown in Table 2.

62 321062 200948929 實施例2至11 除了使用下列第2表所示之化合物來取代化合物1而 製作出發光層之外，其他與實施例1相同來製作出元件。 測定出以發光亮度300(cd/m2)於室溫下對此元件進行定電 流驅動時之效率。此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於30°C的環境下連續驅動 100小時後之亮度。結果如第2表所示。 比較例1 ❹ 除了使用下列化合物C來取代化合物1而製作出發光 層之外，其他與實施例1相同來製作出元件。測定出以發 光亮度3 0 0 (c d / m2)於室溫下對此元件進行定電流驅動時之 效率。此外，並測定出以電流密度12. 5mA/cm2進行驅動時 之初期亮度、以及於30°C的環境下連續驅動100小時後之 亮度。結果如第2表所示。62 321062 200948929 Examples 2 to 11 The elements were produced in the same manner as in Example 1 except that the compound shown in the following Table 2 was used instead of the compound 1 to prepare a light-emitting layer. The efficiency at which the element was subjected to constant current driving at room temperature with a luminance of 300 (cd/m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 2. Comparative Example 1 元件 An element was produced in the same manner as in Example 1 except that the following compound C was used instead of the compound 1 to prepare a light-emitting layer. The efficiency at which the element was subjected to constant current driving at room temperature with a luminance of 300 (c d / m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 2.

化合物c 63 321062 200948929 [第2表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 1 1 3.4 340 310 2 3 3. 2 350 320 3 10 2. 9 400 370 4 23 3. 7 340 300 5 53 2.4 420 370 6 63 2. 9 290 280 7 68 3. 0 300 270 8 78 1. 9 380 350 9 88 3. 2 390 340 10 99 2. 5 330 290 11 100 2.7 310 260 比較例1 C 0.4 120 40 從第2表中可得知，本發明之化合物，均較比較例1 所製作之元件更具有長壽命且可獲得高效率。 實施例12 將下列化合物D真空蒸鍍於附有ΙΤ0電極的玻璃板 上，而製得膜厚70nm的電洞注入層。接著以5 : 100的組 成比，將化合物1與下列化合物E予以共蒸鍍，而形成膜 厚40nm的發光層。之後將TPBI予以蒸鍍而製得膜厚20nm 的電子注入層。於其上首先蒸鍍氟化鋰lnm，然後再蒸鍍 A1為lOOnm來形成陰極，而製得有機EL元件。以發光亮 度300(cd/m2)於室溫下對此元件進行定電流驅動後之色 度，為CIE(x，yM〇. 15,0. 11)的藍色發光，發光效率為 6. 3cd/A。此外，並測定出以電流密度12. 5mA/cm2進行驅 64 321062 200948929 動時之初期壳度、以及於3(TC的環境下連續驅動loo小時 後之亮度。結果如第3表所示。Compound c 63 321062 200948929 [Table 2] Example compound luminous efficiency (cd/A) Current density 12. 5 mA/cm 2 Initial luminance (cd/m 2 ) 30 ° C, luminance after 100 hours (cd/m 2 ) 1 1 3.4 340 310 2 3 3. 2 350 320 3 10 2. 9 400 370 4 23 3. 7 340 300 5 53 2.4 420 370 6 63 2. 9 290 280 7 68 3. 0 300 270 8 78 1. 9 380 350 9 88 3. 2 390 340 10 99 2. 5 330 290 11 100 2.7 310 260 Comparative Example 1 C 0.4 120 40 As can be seen from Table 2, the compounds of the present invention are more than the components produced in Comparative Example 1. Has a long life and high efficiency. Example 12 The following Compound D was vacuum-deposited on a glass plate with a ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 70 nm. Next, Compound 1 and the following Compound E were co-evaporated at a composition ratio of 5:100 to form a light-emitting layer having a film thickness of 40 nm. Thereafter, TPBI was vapor-deposited to obtain an electron injecting layer having a film thickness of 20 nm. On this, an organic EL device was obtained by first vapor-depositing lithium fluoride 1 nm, and then vapor-depositing A1 to 100 nm to form a cathode. The luminescence efficiency is 6. 3cd. The luminosity of the CIE (x, yM 〇. 15,0. 11), the luminescence efficiency is 6. 3cd. /A. Further, the initial shell degree at the time of the current density of 12.5 mA/cm 2 was measured, and the brightness was continuously driven after loo hours in the environment of TC. The results are shown in Table 3.

❹實施例13至31 除了使用第3表中的化合物來取代化合物1之外，其 他與實施例12相同來製作出元件。這些元件在以發光亮度 300(cd/m2)於室溫下進行定電流驅動後之發光色，係顯現 出藍色，且發光效率均為4cd/A以上。此外，並測定出以 電流密度12. 5mA/cm2進行驅動時之初期亮度、以及於3〇 C的環境下連續驅動1〇〇小時後之亮度。結果如第3表所 ©示。 比較例2至3 除了使用化合物C(比較例2)、下列化合物F(比較例 3)來取代化合物1之外，其他與實施例12相同來製作出元 件。測定出以發光亮度300(cd/m2)於室溫下對這些元件進 行定電流驅動時之發光效率。此外，並測定出以電流密度 12. 5mA/cm2進行驅動時之初期亮度、以及於30°C的環境下 連續驅動100小時後之亮度。結果如第3表所示。 521062 65 200948929Examples 13 to 31 Other than Example 1, except that the compound in Table 3 was used instead of Compound 1, an element was produced. These elements exhibited a blue color when the constant light was driven at a room temperature of 300 (cd/m2), and the luminous efficiency was 4 cd/A or more. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 1 hour in an environment of 3 〇 C were measured. The results are shown in Table 3. Comparative Examples 2 to 3 Parts were produced in the same manner as in Example 12 except that the compound C (Comparative Example 2) and the following Compound F (Comparative Example 3) were used instead of the compound 1. The luminous efficiency at the time of constant current driving of these elements at room temperature with a luminance of 300 (cd/m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 3. 521062 65 200948929

[第3表] 實施例 化合物 發光效率 (cd/A) 發光色 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 12 1 6.3 藍色 630 560 13 2 5.7 藍色 540 470 14 3 5.3 藍色 690 620 15 4 6.2 藍色 740 630 16 13 4.6 藍色 530 480 17 17 5.8 藍色 490 440 18 24 4.3 藍色 590 500 19 34 5.9 藍色 530 490 20 41 6.0 藍色 630 560 21 53 6.6 藍色 530 470 22 55 4.9 藍色 680 620 23 57 5.7 藍色 550 510 24 59 5.1 藍色 530 490 25 64 5.5 藍色 480 440 26 71 4.3 藍色 710 620 27 80 5.8 藍色 680 650 28 84 6.4 藍色 610 560 29 97 4.7 藍色 640 570 30 105 5.2 藍色 470 420 31 111 4.4 藍色 520 470 比較例2 C 1.1 水色 340 150 比較例3 F 2.3 水色 410 130 從第3表中可得知，本發明之化合物，均較比較例2 及3所製作之元件，更顯現出色純度高之藍色，具有長壽 66 321062 200948929 命且可獲得高效率。 實施例32 將下列化合物G真空蒸鍍於附有IT〇電極的玻璃板 上，而製得膜厚80nm的電洞注入層。接著以1〇0 : 3的重 量組成比，將化合物E與化合物1予以共蒸鍍，而形成膜 厚30nm的發光層。之後將化合物B予以蒸鍍而製得膜厚 30nm的電子注入層。於其上首先蒸鍍氧化鋰（Li2〇)lnm， 然後再蒸鍍A1為l〇〇nm來形成陰極，而製得有機EL元件。 ❹以發光亮度300(cd/m2)於室溫下對此元件進行定電流驅動 時之發光效率為5. 2cd/A。此外，並測定出以電流密度 12.5mA/cm2進行驅動時之初期亮度、以及於30°C的環境下 連續驅動100小時後之亮度。結果如第4表所示。[Table 3] Example compound Luminous efficiency (cd/A) Luminescent current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, luminance after 100 hours (cd/m 2 ) 12 1 6.3 Blue 630 560 13 2 5.7 Blue 540 470 14 3 5.3 Blue 690 620 15 4 6.2 Blue 740 630 16 13 4.6 Blue 530 480 17 17 5.8 Blue 490 440 18 24 4.3 Blue 590 500 19 34 5.9 Blue 530 490 20 41 6.0 Blue 630 560 21 53 6.6 Blue 530 470 22 55 4.9 Blue 680 620 23 57 5.7 Blue 550 510 24 59 5.1 Blue 530 490 25 64 5.5 Blue 480 440 26 71 4.3 Blue 710 620 27 80 5.8 Blue 680 650 28 84 6.4 Blue 610 560 29 97 4.7 Blue 640 570 30 105 5.2 Blue 470 420 31 111 4.4 Blue 520 470 Comparative Example 2 C 1.1 Water 340 150 Comparative Example 3 F 2.3 Aqua 410 130 It can be seen from the third table that the compounds of the present invention are more excellent in blue with excellent purity than those produced in Comparative Examples 2 and 3, and have longevity 66 321062 200948929 and high efficiency can be obtained. Example 32 The following compound G was vacuum-deposited on a glass plate with an IT crucible electrode to prepare a hole injection layer having a film thickness of 80 nm. Next, the compound E and the compound 1 were co-deposited at a weight ratio of 1 〇 0 : 3 to form a light-emitting layer having a film thickness of 30 nm. Thereafter, the compound B was subjected to vapor deposition to obtain an electron injecting layer having a film thickness of 30 nm. On this, an organic EL element was obtained by first vapor-depositing lithium oxide (Li 2 〇) 1 nm, and then vapor-depositing A1 to 10 nm to form a cathode. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 4.

實施例33至50 除了使用第4表中的化合物來取代化合物1之外，其 他與實施例32相同來製作出元件。將這些元件以發光亮声 3(i0(cd/m2)於室溫下進行定電流驅動時之發光效率均為 4cd/A以上，此外，並測定出以電流密度12. 5mA/cm2進行 驅動時之初期亮度、以及於3CTC的環境下連續驅動1〇〇 ^ 321062 67 200948929 時後之亮度。結果如第4表所示。 比較例4 除了使用化合物C來取代化合物1之外，其他與實施 例32相同來製作出元件。測定出以發光亮度300(cd/m2) 於室溫下對該元件進行定電流驅動時之發光效率。此外， 並測定出以電流密度12. 5mA/cm2進行驅動時之初期亮度、 以及於30°C的環境下連續驅動100小時後之亮度。結果如 第4表所示。 [第4表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 勒期免度 (cd/m2) 30°C、100小時後之 亮度 (cd/m2) 32 1 5.2 540 480 33 2 5.7 670 600 34 6 6.3 550 480 35 8 6.2 630 560 36 26 5.1 610 530 37 28 5.8 590 530 38 31 4.3 540 490 39 38 4.3 630 540 40 44 6.3 540 480 41 48 5.7 480 420 42 53 6.3 610 520 43 63 6.6 570 500 44 68 5.7 600 510 45 73 5.9 470 430 46 88 6.3 590 500 47 94 5.3 620 550 48 104 4.2 530 470 49 115 4.4 540 490 50 118 4.7 490 430 比較例4 C 1.4 220 100 68 321062 200948929 從第4表中可得知’本發明之化合物，均較比較例$ 所製作之元件更具有長壽命且可獲得高效率。 實施例.51 將化合物D真空蒸鍍於附有Π0電極的玻璃板上，而 製得膜厚65nm的電洞注入層。接著以3 : 1〇〇的組成比， 將下列化合物Η與化合物1予以共蒸鍍，而形成膜厚30nm 的發光層。之後將TPBI予以蒸鍍而製得膜厚3〇nm的電子 庄入層於其上首先蒸鍍氟化鋰lnm，然後再蒸鍍A1為 O 1GGnm來形成陰極，•得有機EL元件。以發光亮度 300(cd/m )於室溫下對此元件進行定電流驅動後之色度， 為CIE(x, y)_(〇. i6,〇. 13)的藍色發光，發光效率為 5. lcd/A。此外，並測定出以電流密度125mA/⑽2進行驅 動時之初期亮度、以及於3(rc的環境下連續驅動1〇〇小 時，接著再於10(TC的環境下連續驅動24小時後之各種驅 動後之亮度。結果如第5表所示。Examples 33 to 50 The elements were produced in the same manner as in Example 32 except that the compound in Table 4 was used instead of Compound 1. When the current is driven at a current density of 12.5 mA/cm 2 , the light-emitting efficiency is 4 cd/A or more when the current is driven at a constant current of 4 cd/A. The initial brightness and the brightness after 1 〇〇 321062 67 200948929 were continuously driven in the environment of 3 CTC. The results are shown in Table 4. Comparative Example 4 In addition to the use of Compound C instead of Compound 1, other examples And the light-emitting efficiency of the element is measured at a current density of 12. 5 mA/cm 2 when the current density is 12. 5 mA/cm 2 . The initial brightness and the brightness after continuous driving for 100 hours in an environment of 30 ° C. The results are shown in Table 4. [Table 4] Example compound luminous efficiency (cd/A) Current density 12. 5 mA/cm 2 Exemption (cd/m2) 30 ° C, brightness after 100 hours (cd/m2) 32 1 5.2 540 480 33 2 5.7 670 600 34 6 6.3 550 480 35 8 6.2 630 560 36 26 5.1 610 530 37 28 5.8 590 530 38 31 4.3 540 490 39 38 4.3 630 540 40 44 6.3 540 480 41 48 5.7 480 420 42 53 6.3 610 520 43 63 6.6 600 570 45 73 5.9 470 430 46 88 6.3 590 500 47 94 5.3 620 550 48 104 4.2 530 470 49 115 4.4 540 490 50 118 4.7 490 430 Comparative example 4 C 1.4 220 100 68 321062 200948929 It can be seen from Table 4 that the compounds of the present invention all have a longer life and higher efficiency than the components produced in Comparative Example $. Example. 51 Vacuum evaporation of Compound D A hole injection layer having a film thickness of 65 nm was prepared on a glass plate with a Π0 electrode, and then the following compound Η and the compound 1 were co-deposited at a composition ratio of 3:1 , to form a film thickness of 30 nm. After the TPBI is vapor-deposited, an electronic layer having a thickness of 3 〇 nm is formed thereon, firstly, lithium fluoride is deposited at a thickness of 1 nm, and then A1 is deposited as O 1 GGnm to form a cathode, and an organic EL is obtained. The chromaticity of the element after constant current driving at room temperature with a luminance of 300 (cd/m) is CIE(x, y)_(〇. i6, 〇. 13) blue luminescence, luminescence The efficiency is 5. lcd/A. In addition, the initial luminance at the time of driving at a current density of 125 mA/(10) 2 and the continuous driving for 3 hours in an environment of rc, and then various driving after continuous driving for 24 hours in a TC environment were measured. After the brightness, the results are shown in Table 5.

除了使用第5表中的化合物來取代化合物丨之外 他與實施例51相同來製作出元件。將這些元件以發光^ 300(cd/m2)於室溫下進行定電流驅動時之發光效率均為 321062 69 200948929 5cd/A以上。此外，並測定出以電流密度12. 5mA/cm2進行 驅動時之初期亮度、以及於30°C的環境下連續驅動100小 時，接著再於l〇〇°C的環境下連續驅動24小時後之各種驅 動後之亮度。結果如第5表所示。 比較例5 除了使用下列化合物I來取代化合物1之外，其他與 實施例51相同來製作出元件。測定出以發光亮度 300(cd/m2)於室溫下對該元件進行定電流驅動時之發光效 率。此外，並測定出以電流密度12. 5mA/cm2進行驅動時之 © 初期亮度、以及於30°C的環境下連續驅動100小時，接著 再於100°C的環境下連續驅動24小時後之各種驅動後之亮 度。結果如第5表所示。An element was produced in the same manner as in Example 51 except that the compound in Table 5 was used instead of the compound 丨. When these elements were driven by constant current driving at room temperature of 1300 (cd/m2), the luminous efficiencies were 321062 69 200948929 5 cd/A or more. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the continuous driving for 100 hours in an environment of 30 ° C were measured, followed by continuous driving for 24 hours in an environment of 10 ° C. The brightness of various drivers. The results are shown in Table 5. Comparative Example 5 An element was produced in the same manner as in Example 51 except that the following compound I was used instead of the compound 1. The luminous efficiency when the element was subjected to constant current driving at a room temperature of 300 (cd/m2) was measured. In addition, the initial brightness of the drive at a current density of 12.5 mA/cm 2 and the continuous driving for 100 hours in an environment of 30 ° C, followed by continuous driving for 24 hours in an environment of 100 ° C were measured. The brightness after driving. The results are shown in Table 5.

70 321062 200948929 [第5表]70 321062 200948929 [Table 5]

實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後 之亮度 (cd/m2) 100°C、24小時後 之亮度 (cd/m2) 51 1 5.1 560 510 390 52 2 5.8 490 450 360 53 3 5.4 590 550 490 54 4 6.7 600 560 500 55 13 6.4 480 460 380 56 20 5.0 590 560 450 57 25 6.9 510 480 450 58 39 6.3 490 460 390 59 47 6.8 620 580 510 60 54 5.9 580 550 480 61 58 6.0 550 500 430 62 62 7.0 610 570 510 63 63 5.6 430 400 330 64 64 6.8 560 520 480 65 71 5.8 540 510 380 66 72 6.1 640 600 530 67 78 6.7 470 440 370 68 80 5.4 500 450 410 69 81 5.7 570 540 460 70 84 6.8 560 540 480 71 86 6.5 490 460 400 72 94 6.2 550 530 450 73 101 6.0 590 560 510 74 108 6.6 570 520 470 比較例 5 I 1.4 270 130 20 從第5表中可得知，本發明之化合物，均較比較例5 所製作之元件更具有長壽命且可獲得高效率。 實施例75 將化合物G真空蒸鍍於附有ΙΤ0電極的玻璃板上，而 製得膜厚60nm的電洞注入層。接著以2 : 100的組成比， 將下列化合物J與化合物1予以共蒸鍍，而形成膜厚40nm 71 321062 200948929 ， 的發光層。之後將TPBI予以蒸鑛而製得膜厚4Onm的電子 注入層。於其上首先蒸鍍氣化鐘Inm，然後再蒸鍵A1為 lOOnm來形成陰極，而製得有機EL元件。以發光亮度 300(cd/m2)於室溫下對此元件進行定電流驅動後之色度， 為CIE(x，yM〇. 14, 0· 15)的藍色發光，發光效率為 4. 7cd/A。此外，並測定出以電流密度丨2. 5mA/cm2進行驅 動時之初期亮度、以及於30°C的環境下連續驅動小時 後之亮度。結果如第6表所示。Example compound Luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, brightness after 100 hours (cd/m 2 ) 100 ° C, brightness after 24 hours (cd/ M2) 51 1 5.1 560 510 390 52 2 5.8 490 450 360 53 3 5.4 590 550 490 54 4 6.7 600 560 500 55 13 6.4 480 460 380 56 20 5.0 590 560 450 57 25 6.9 510 480 450 58 39 6.3 490 460 390 59 47 6.8 620 580 510 60 54 5.9 580 550 480 61 58 6.0 550 500 430 62 62 7.0 610 570 510 63 63 5.6 430 400 330 64 64 6.8 560 520 480 65 71 5.8 540 510 380 66 72 6.1 640 600 530 67 78 6.7 470 440 370 68 80 5.4 500 450 410 69 81 5.7 570 540 460 70 84 6.8 560 540 480 71 86 6.5 490 460 400 72 94 6.2 550 530 450 73 101 6.0 590 560 510 74 108 6.6 570 520 470 Comparative example 5 I 1.4 270 130 20 As can be seen from the fifth table, the compounds of the present invention have a longer life and higher efficiency than the elements produced in Comparative Example 5. Example 75 Compound G was vacuum-deposited on a glass plate with a ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the following compound J and the compound 1 were co-deposited at a composition ratio of 2:100 to form a light-emitting layer having a film thickness of 40 nm, 71 321062 and 200948929. Thereafter, TPBI was subjected to steaming to obtain an electron injecting layer having a film thickness of 4 Onm. The gasification clock Inm was first vapor-deposited thereon, and then the vapor-bonding A1 was made to be 100 nm to form a cathode, thereby producing an organic EL element. The luminescence efficiency is 4. 7cd. The luminosity of the CIE (x, yM 〇. 14, 0·15) is 4, 7cd. /A. Further, the initial luminance at the time of driving at a current density of 2.5 mA/cm 2 and the luminance after continuous driving for 30 hours at 30 ° C were measured. The results are shown in Table 6.

〇 化合物j 實施例76至83 除了使用第6表中的化合物來取代化合物1之外，其 他與實施例75相同來製作出元件。將這些元件以發光亮度 300(cd/m2)於室溫下進行定電流驅動時之發光效率均為 4cd/A以上，此外，並測定出以電流密度12· 5mA/cm2進行 驅動時之初期亮度、以及於30°C的環境下連續驅動100小 時後之亮度。結果如第6表所示。 72 321062 200948929 [第6表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/in2) 30°C、100小時後之亮度 (cd/m2) 75 1 4.7 470 430 76 4 5.2 550 500 77 24 4. 8 460 410 78 26 4.4 530 480 79 52 5.7 卜570 500 80 59 5. 3 450 410 81 75 6.4 590 560 — 82 86 5.7 510 480 83 89 6. 1 490 460 — 實施例84 將下列化合物K蒸鍍於附有ΙΤ0電極的玻璃板上，而 製得膜厚60nm的電洞注入層。接著以1〇〇 : 5的組成比， 將第1表的化合物2與下列化合物L予以共蒸鍍，而形成 膜厚40nm的發光層。之後將Balq(下列化合物M)予以蒸鍍 而製得膜厚10nm的電洞阻止層，然後於其上將Alq3(Tris ❹（8-Hydroxyquinoline)Alumiiiiuin :參f8-羥基喹啉）鋁）予 以真空蒸鍍而製得膜厚30nm的電子注入層，於其上首先蒸 鍍氟化鋰lnm，然後再蒸鍍A1為200nm來形成電極，而製 得有機EL元件。以發光亮度300(cd/m2)於室溫下對此元 件進行定電流驅動時，係顯現出藍色發光，發光效率為 9.5cd/A 。 73 321062 200948929化合物 Compound j Examples 76 to 83 In the same manner as in Example 75 except that the compound in Table 6 was used instead of Compound 1, an element was produced. When these elements were driven at a constant current of 300 (cd/m 2 ) at room temperature, the luminous efficiency was 4 cd/A or more, and the initial luminance at the time of driving at a current density of 12·5 mA/cm 2 was measured. And the brightness after continuous driving for 100 hours in an environment of 30 ° C. The results are shown in Table 6. 72 321062 200948929 [Table 6] Example compound Luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial brightness (cd/in2) 30 ° C, brightness after 100 hours (cd/m2) 75 1 4.7 470 430 76 4 5.2 550 500 77 24 4. 8 460 410 78 26 4.4 530 480 79 52 5.7 570 500 80 59 5. 3 450 410 81 75 6.4 590 560 — 82 86 5.7 510 480 83 89 6. 1 490 460 — Example 84 The following compound K was vapor-deposited on a glass plate with a ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the compound 2 of the first table and the following compound L were co-deposited at a composition ratio of 1 〇〇:5 to form a light-emitting layer having a film thickness of 40 nm. Then, Balq (the following compound M) was vapor-deposited to obtain a hole-stopping layer having a film thickness of 10 nm, and then Alq3 (Tris ❹(8-Hydroxyquinoline) Alumiiiiuin: ginseng f8-hydroxyquinoline) aluminum was vacuumed thereon. An electron injecting layer having a film thickness of 30 nm was formed by vapor deposition, and lithium fluoride was first deposited thereon to a thickness of 1 nm, and then an electrode was vapor-deposited to form an electrode to form an electrode to obtain an organic EL device. When the element was subjected to constant current driving at a room temperature of 300 (cd/m2), blue light emission was exhibited, and the luminous efficiency was 9.5 cd/A. 73 321062 200948929

實施例85至87 除了使用第7表中的化合物來取代化合物2之外，其 他與實施例84相同來製作出元件。將這些元件以發光亮度 300(cd/m2)於室溫下進行定電流驅動時之發光效率均為 9cd/A以上。結果如第7表所示。 [第7表] 實施例 化合物 發光效率 (cd/A) 84 2 9. 5 85 9 10. 2 86 46 9. 2 87 97 9. 8 實施例88 以旋轉塗佈法使PED0T/PSS (聚（3，4-伸乙二氧基）-2, 5-噻吩/聚苯乙烯磺酸、Bayer公司製BAYTRON P VP CH8000)成膜於洗淨後之附有ΙΤ0電極的玻璃板上，而製得 膜厚50nm的電洞注入層。接著以2. Owt%的濃度，將60 74 321062 200948929 %的PVK(聚乙烯咔唑）、4%的化合物77及36%的電子傳 輸材料（下列化合物N)溶解於曱苯，並藉由旋轉塗佈法而 製得膜厚60nm的發光層。之後於其上蒸鍍Ca為2〇nm後， 再蒸鍍A1為200nm來形成電極，而製得有機el元件。對 此元件進行通電試驗時，可獲得最大發光亮度為48〇cd/m2 的藍色發光。Examples 85 to 87 In the same manner as in Example 84 except that the compound in Table 7 was used instead of Compound 2, an element was produced. When these elements were driven at a constant current of 300 (cd/m2) at room temperature, the luminous efficiency was 9 cd/A or more. The results are shown in Table 7. [Table 7] Example compound Luminous efficiency (cd/A) 84 2 9. 5 85 9 10. 2 86 46 9. 2 87 97 9. 8 Example 88 PED0T/PSS (poly() by spin coating 3,4-Exetylenedioxy)-2,5-thiophene/polystyrenesulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer Co., Ltd. was formed into a film on a glass plate with a ΙΤ0 electrode after washing, and obtained. A hole injection layer having a film thickness of 50 nm. Next, 60 74 321062 200948929 % PVK (polyvinylcarbazole), 4% compound 77 and 36% electron transport material (the following compound N) were dissolved in toluene at a concentration of 2.0 wt%, and rotated by A light-emitting layer having a film thickness of 60 nm was obtained by a coating method. Thereafter, after Ca was vapor-deposited to 2 nm, the electrode was formed by vapor-depositing A1 to 200 nm to prepare an organic EL element. When this component was subjected to a current test, blue light having a maximum luminance of 48 〇cd/m2 was obtained.

實施例89 以旋轉塗佈法使PED〇T/pss(聚（3,4_伸乙二氧基）_ 2’ 5-嗟吩/聚苯乙烯確酸、Bayer公司製baytron p vp CH8000)成膜於洗淨後之附有IT〇電極的玻璃板上，而製得 膜厚50nm的電洞注入層。接著以2. 〇wt%的濃度，將6〇 %的PVK(聚乙烯咔唑）、5%的化合物82及35%的電子傳 ⑩1材料（下列化合物〇)溶解於甲苯，並藉由旋轉塗佈法而 製得膜厚7〇11111的發光層。之後於其上蒸鐘Ca為20nm後， 再蒸鍍A1為2〇〇nm來形成電極，而製得有機EL元件。對 此元件進行通電試驗時’可獲得最大發光亮度為37〇cd/m2 的藍色發光。Example 89 PED〇T/pss (poly(3,4_ethylenedioxy)_ 2' 5- porphin/polystyrene acid, Baytron p vp CH8000 manufactured by Bayer Co., Ltd.) was spin-coated. The film was washed on a glass plate to which an IT crucible electrode was attached to prepare a hole injection layer having a film thickness of 50 nm. Next, 6〇% of PVK (polyvinylcarbazole), 5% of compound 82 and 35% of electron-transporting 101 material (the following compound 〇) were dissolved in toluene at a concentration of 2. 〇wt%, and spin-coated A light-emitting layer having a film thickness of 7〇11111 was obtained by a cloth method. Thereafter, after the vapor Ca was 20 nm thereon, the electrode was formed by vapor-depositing A1 to 2 〇〇 nm to prepare an organic EL device. When the element was subjected to a current test, blue light having a maximum light emission luminance of 37 〇cd/m2 was obtained.

實施例9 0 75 · 321062 200948929 將本發明之化合物32真空蒸鍍於洗淨後之附有IT〇 電極的玻璃板上’而製得膜厚50nm的電洞注入層。接著將 化合物A予以真空蒸鐘而製得膜厚30nm的電洞傳輸層。再 將A1 q3予以真空療·鍵而製得膜厚5Οηιη的電子注入型發光 層’於其上首先蒸鏟敗化鐘lnm，然後再蒸鍍A1為2〇〇nm 來形成電極’而製付有機EL το件。對此元件進行通電試驗 時，可獲得最大發光亮度為1610cd/m2的黃色發光。 實施例91 將化合物D蒸鑛於附有IT0電極的玻璃板上，形成膜 厚50nm的電洞注入層後’將化合物50予以蒸鍍而形成膜 厚30nm的電洞傳輸層。接著將Alq3予以蒸鑛而形成膜厚 50nm的電子注入型發光層，於其上首先蒸鍍氟化鋰lnm， 然後再藉由真空蒸鑛形成A1為20Onm來形成電極，而製得 有機EL元件。對此元件進行通電試驗時，可獲得最大發光 亮度為1840cd/m2的黃色發光。 實施例犯 將化合物D真空蒸鍍於附有IT0電極的玻璃板上，製 得膜厚5〇nm的電洞注入層。接著將Alq3予以蒸鍍而形成 膜厚40nm的發光層。然後將化合物19予以蒸鍍而形成膜 厚30nm的電子注入層。於其上首先蒸鍍氟化鋰lnm，然後 再藉由蒸鍍形成A1為lOOnm來形成陰極，而製得有機el 元件。對此元件進行通電試驗時，可獲得最大發光亮度為 1740cd/m2的黃色發光。 實施例93 321062 76 200948929 除了使用化合物15來取代化合物19之外，其他與實 施例92相同而製作出元件。對此元件進行通電試驗時，可 獲得最大發光亮度為1580cd/m2的黃色發光。 實施例94 將a -NPD真空蒸鍍於洗淨後之附有IT〇電極的玻璃板 上，而製得膜厚60nm的電洞注入層。接著將化合物131 予以真空蒸鍍而製得膜厚30nm的發光層。之後將τρΒΐ予 以真空蒸鐘而製得膜厚30nm的電子注入層，於其上首先蒸 © 鍍氟化鋰lnm，然後再蒸鍍A1為150nm來形成電極，而製 钎有機EL元件。以發光亮度300(cd/m2)於室溫下對此元 件進行定電流驅動時之色度，為CIE(x，y)=(〇. 14, 〇. 10)的 藍色發光，發光效率為2· 6cd/A。此外，並測定出以電流 密度12.5mA/cm2進行驅動後之初期亮度、以及於3(rc的環 境下連續驅動100小時後之亮度。結果如第8表所示。 實施例95至108 ❾ 除了使用下列第8表所示之化合物來取代化合物131 而製作出發光層之外，其他與實施例94相同來製作出元 件。測定出以發光亮度300(cd/m2)於室溫下對此元件進行 定電流驅動時之效率。此外’並測定出以電流密度 12. 5mA/cm2進行驅動時之初期亮度、以及於3〇°c的環境下 連續驅動100小時後之亮度。結果如第8表所示。 比較例6 除了使用下列化合物P來取代化合物131而製作出發 光層之外，其他與實施例94相同來製作出元件。測定出以 321062 77 200948929 發光亮度300(cd/m2)於室溫下對此元件進行定電流驅動時 之效率。此外，並測定出以電流密度12. 5mA/cin2進行驅動 時之初期亮度、以及於30°C的環境下連續驅動100小時後 之亮度。結果如第8表所示。Example 9 0 75 · 321062 200948929 The compound 32 of the present invention was vacuum-deposited on a glass plate with an IT crucible attached thereto to prepare a hole injection layer having a film thickness of 50 nm. Next, Compound A was subjected to vacuum distillation to obtain a hole transport layer having a film thickness of 30 nm. Then, A1 q3 is subjected to a vacuum treatment key to obtain an electron-injection-type light-emitting layer having a film thickness of 5 Οηη, on which the first electrode is steamed and smashed to a thickness of 1 nm, and then A1 is evaporated to form an electrode to form an electrode. Organic EL το pieces. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1610 cd/m2 was obtained. Example 91 The compound D was distilled from a glass plate to which an IT0 electrode was attached to form a hole injection layer having a thickness of 50 nm, and the compound 50 was vapor-deposited to form a hole transport layer having a film thickness of 30 nm. Next, Alq3 is subjected to vaporization to form an electron injecting type light-emitting layer having a film thickness of 50 nm, and firstly, lithium fluoride is deposited thereon to a thickness of 1 nm, and then an electrode is formed by vacuum evaporation to form an electrode of 20 nm to form an organic EL device. . When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1840 cd/m2 was obtained. EXAMPLES Compound D was vacuum-deposited on a glass plate to which an IT0 electrode was attached to prepare a hole injection layer having a film thickness of 5 Å. Next, Alq3 was vapor-deposited to form a light-emitting layer having a film thickness of 40 nm. Then, the compound 19 was vapor-deposited to form an electron injecting layer having a film thickness of 30 nm. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1 nm and then forming a cathode by vapor deposition to form A1 to be 100 nm. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1740 cd/m2 was obtained. Example 93 321062 76 200948929 An element was produced in the same manner as in Example 92 except that Compound 15 was used instead of Compound 19. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1,580 cd/m2 was obtained. Example 94 A-NPD was vacuum-deposited on a cleaned glass plate with an IT crucible electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the compound 131 was subjected to vacuum evaporation to obtain a light-emitting layer having a film thickness of 30 nm. Thereafter, an electron injecting layer having a film thickness of 30 nm was formed by vacuum evaporation, and an organic EL device was formed by first evaporating lithium fluoride 1 nm, and then vapor-depositing A1 to 150 nm to form an electrode. The chromaticity when the element is subjected to constant current driving at a room temperature of 300 (cd/m 2 ) is CIE(x, y)=(〇. 14, 〇.10), and the luminous efficiency is 2·6cd/A. Further, the initial luminance after driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 3 hours in an environment of 3 (rc) were measured. The results are shown in Table 8. Examples 95 to 108 ❾ An element was produced in the same manner as in Example 94 except that the compound 131 was replaced with the compound shown in the following Table 8. The light-emitting luminance was 300 (cd/m 2 ) at room temperature. The efficiency at the time of constant current driving was measured. Further, the initial luminance at the time of driving at a current density of 10.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 3 〇 ° C were measured. Comparative Example 6 An element was produced in the same manner as in Example 94 except that the following compound P was used instead of the compound 131 to prepare a light-emitting layer, and a luminance of 300 (cd/m 2 ) was measured at 321062 77 200948929. The efficiency at the time of constant current driving of the element was measured at a temperature, and the initial brightness at the time of driving at a current density of 12.5 mA/cin2 and the brightness after continuous driving for 100 hours in an environment of 30 ° C were measured. As shown in Table 8 fruit.

化合物PCompound P

[第8表] 實施例 化合物 發先效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 94 131 2. 6 460 420 95 134 3. 5 420 370 96 145 2. 4 350 330 97 150 3. 1 360 330 98 155 2. 1 280 240 99 177 3. 7 410 350 100 179 2.2 440 360 101 183 2. 9 450 410 102 193 2. 8 390 320 103 198 2. 9 340 310 104 216 2. 3 370 340 105 219 3. 1 370 320 106 235 3. 5 390 360 107 242 3. 3 440 390 108 271 2. 8 400 380 比較例 6 P 0. 3 90 20 從第8表中可得知，本發明之化合物，均較比較例6 所製作之元件更具有長壽命且可獲得高效率。 78 321062 200948929 實施例109 將下列化合物Q真空蒸鍍於附有IT〇電極的玻璃板 上，而製得膜厚80nm的電洞注入層。接著以3 : 1〇〇的組 成比’將化合物131與下列化合物r予以共蒸鍍，而形成 膜厚35nm的發光層。之後將Τρβΐ予以蒸鐘而製得膜厚 35nm的電子注入層。於其上首先蒸鍍氟化鋰lnm，然後再 蒸鍍A1為100nm來形成陰極，而製得有機EL元件。以發 光壳度300(cd/m2)於室溫下對此元件進行定電流驅動後之 ©色度，為CIE(x，y)=(o. 12,〇. 1〇)的藍色發光，發光效率為 6. Ocd/A。此外，並測定出以電流密度12· 5mA/cm2進行驅 動時之初期亮度、以及於3(rc的環境下連續驅動1〇〇小時 後之壳度。結果如第9表所示。[Table 8] Example compound initial efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, luminance after 100 hours (cd/m 2 ) 94 131 2. 6 460 420 95 134 3. 5 420 370 96 145 2. 4 350 330 97 150 3. 1 360 330 98 155 2. 1 280 240 99 177 3. 7 410 350 100 179 2.2 440 360 101 183 2. 9 450 410 102 193 2. 8 390 320 103 198 2. 9 340 310 104 216 2. 3 370 340 105 219 3. 1 370 320 106 235 3. 5 390 360 107 242 3. 3 440 390 108 271 2. 8 400 380 Comparative example 6 P 0. 3 90 20 As can be seen from the eighth table, the compounds of the present invention have a longer life and higher efficiency than the elements produced in Comparative Example 6. 78 321062 200948929 Example 109 The following compound Q was vacuum-deposited on a glass plate with an IT crucible electrode to prepare a hole injection layer having a film thickness of 80 nm. Subsequently, the compound 131 and the following compound r were co-deposited at a composition ratio of 3:1 Å to form a light-emitting layer having a film thickness of 35 nm. Thereafter, Τρβΐ was subjected to steaming to obtain an electron injecting layer having a film thickness of 35 nm. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1 nm, and then vapor-depositing A1 to 100 nm to form a cathode. The chromaticity of the element after constant current driving of the element at room temperature of 300 (cd/m2) is CIE(x, y)=(o.12, 〇.1〇) blue luminescence, The luminous efficiency is 6. Ocd/A. Further, the initial luminance at the time of driving at a current density of 12·5 mA/cm 2 and the shell degree after continuous driving for 1 hour in an environment of 3 (rc) were measured. The results are shown in Table 9.

除了使用第9表中的化合物來取代化合物131之外， 其他與實施例1G9相同來製作出元件。這些元件在以發光 壳度300(cd/m2)於室溫下進行定電流驅動後之發光色，係 顯現出藍色，且發光效率均為5cd/A以上。此外，並測定 出以電流密度12. 5mA/em2進行驅動時之初期亮度、以及於 30C的環境下連續驅動_小時後之亮度。結果如第9表 實施例110至130 所示。 79 321062 200948929 比較例7至8 除了使用化合物P (比較例7 )、下列化合物S (比較例 8)來取代化合物131之外，其他與實施例109相同來製作 出元件。測定出以發光亮度300(cd/m2)於室溫下對這些元 件進行定電流驅動時之發光效率。此外，並測定出以電流 密度12. 5mA/cm2進行驅動時之初期亮度、以及於30°C的環 境下連續驅動1〇〇小時後之亮度。結果如第9表所示。An element was produced in the same manner as in Example 1G9 except that the compound in Table 9 was used instead of Compound 131. The luminescent color of these elements after driving at a constant current of 300 (cd/m2) at room temperature showed blue color and the luminous efficiency was 5 cd/A or more. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 30 hours in an environment of 30 C were measured. The results are shown in Tables 110 to 130 of Table 9. 79 321062 200948929 Comparative Examples 7 to 8 An element was produced in the same manner as in Example 109 except that the compound P (Comparative Example 7) and the following Compound S (Comparative Example 8) were used instead of the compound 131. The luminous efficiency when these elements were driven at a constant current at a room temperature of 300 (cd/m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 1 hour in an environment of 30 ° C were measured. The results are shown in Table 9.

Q 80 321062 200948929 [第9表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5raA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 109 131 6.0 780 720 110 134 6.4 810 760 111 137 7.4 770 710 112 144 6.4 680 630 113 149 7.2 720 670 114 152 6.1 740 690 115 154 6.8 770 720 116 157 7.8 660 630 117 165 6.2 810 750 118 171 6.9 720 690 119 174 5.8 680 620 120 179 6.4 750 690 121 180 6.6 700 630 122 188 7.3 670 620 123 197 5.7 750 690 124 199 6.7 790 740 125 204 6.9 730 670 126 214 6.3 770 700 127 218 7.0 690 650 128 223 6.4 710 640 129 256 6.6 670 630 130 275 5.8 690 610 比較例7 P 1.3 220 130 比較例8· S 1.6 310 180 從第9表中可得知，本發明之化合物，均較比較例7 及8所製作之元件，更具有長壽命且可獲得高效率。 實施例131 將下列化合物T真空蒸鍍於附有ΙΤ0電極的玻璃板 上，而製得膜厚60nm的電洞注入層。接著以100 : 3的重 81 321062 200948929 而 量組成比，將化合物R與例示化合物133予以， 形成膜厚30韻的發光層。之後將化合物B予以蒸^形成 膜厚3〇nm的電子注入層。於其上首先蒸链w為！⑽， 然後再蒸錄A1為1()_來形成陰極，而製得有機el元件。 此元件在以發光亮度300(cd/m2)於室温下進行定電流驅動 後之發先色，係顯現出藍色’且發光效率為5.9·。此 外，並狀出以電絲度】2· 5mA心2進行驅動時之初期亮 度、以及於30°C的環境下連續驅動1〇〇小時後之亮度。結 果如第10表所示。Q 80 321062 200948929 [Table 9] Example compound luminous efficiency (cd/A) Current density 12. 5raA/cm2 Initial luminance (cd/m2) 30 ° C, brightness after 100 hours (cd/m2) 109 131 6.0 780 720 110 134 6.4 810 760 111 137 7.4 770 710 112 144 6.4 680 630 113 149 7.2 720 670 114 152 6.1 740 690 115 154 6.8 770 720 116 157 7.8 660 630 117 165 6.2 810 750 118 171 6.9 720 690 119 174 5.8 680 620 120 179 6.4 750 690 121 180 6.6 700 630 122 188 7.3 670 620 123 197 5.7 750 690 124 199 6.7 790 740 125 204 6.9 730 670 126 214 6.3 770 700 127 218 7.0 690 650 128 223 6.4 710 640 129 256 6.6 670 630 130 275 5.8 690 610 Comparative Example 7 P 1.3 220 130 Comparative Example 8·S 1.6 310 180 It can be seen from Table 9 that the compounds of the present invention are more capable than the elements produced in Comparative Examples 7 and 8. Long life and high efficiency. Example 131 The following compound T was vacuum-deposited on a glass plate with a ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, a composition ratio of 100:3 by weight 81 321062 200948929 was used, and the compound R and the exemplified compound 133 were applied to form a light-emitting layer having a film thickness of 30. Thereafter, the compound B was evaporated to form an electron injecting layer having a film thickness of 3 Å. On the first steamed chain w is! (10), and then A1 is 1 ()_ to form a cathode, and an organic EL element is produced. This element exhibited a blue color after a constant current driving at a luminance of 300 (cd/m2) at room temperature, and the luminous efficiency was 5.9. Further, the initial brightness when driving with a wire degree of 2·5 mA 2 and the brightness after continuous driving for 1 hour at 30 ° C were obtained. The results are shown in Table 10.

實施例132至141 除了使用第ίο表中的化合物來取代化合物133之 外，其他與實施例131㈣來製作出元件。這些元件在以 發光亮度300(Cd/in2)於室温下進行定電流驅動後之發光 色，均顯現出藍色，且發光效率均為5cd/A以上，此外， 並測定iii以電流密度12. 5mA/Cm2進行驅動時之初期亮度、 以及於30 C的環境下連續驅動丨〇〇小時後之亮度。結果如 第10表所示。 比較例9 除了使用化合物s來取代化合物133之外，其他與實 321062 82 200948929 施!j 來f作出元件，定出以發光亮度(摘 於至》皿下對該兀件進行定電流驅動時之發光效率。此外， 並度12,5mA/cm2進行_時之_亮度、 以及於30 C的錢下連續驅動1〇〇小時後之亮度。結果如 第10表所示。 [第10表] 化合物 發光效率 (cd/A) 發光色 初期亮度 (cd/m2) 電流密度12.5mA/cm2 100小時後之亮度 (cd/m2)Examples 132 to 141 An element was produced in the same manner as in Example 131 (IV) except that the compound in the table of ίο was used instead of the compound 133. The illuminating colors of these elements after constant current driving at a room temperature of 300 (Cd/in2) were all blue, and the luminous efficiencies were all 5 cd/A or more. Further, iii was measured at a current density of 12. The initial brightness when driving at 5 mA/cm2 and the brightness after continuous driving for 30 hours in a 30 C environment. The results are shown in Table 10. Comparative Example 9 In addition to the use of the compound s in place of the compound 133, the other elements were used to determine the light-emitting luminance (sampling the device). Luminous efficiency: In addition, the brightness of 12, 5 mA/cm2 was _ brightness, and the brightness was continuously driven for 1 hour after 30 C. The results are shown in Table 10. [Table 10] Compound Luminous efficiency (cd/A) Initial luminance of luminescent color (cd/m2) Current density of 12.5 mA/cm2 Brightness after 100 hours (cd/m2)

❹ 從第10表中可得知，本發明之化合物，均較比較例9 所製作之7L件更具有長壽命且可獲得高效率。 實施例142 將化合物Q真空蒸鍍於附有IT〇電極的玻璃板上，而 製得膜厚60nm的電洞注入層。接著以3 : 1〇〇的組成比， 將化合物Η與例示化合物131予以共蒸鍍，而形成膜厚 40nm的發光層。之後將ΤΡΒΙ予以蒸鍍而製得膜厚4〇nm的 電子注入層。於其上首先蒸鍍氟化鋰lnm，然後再蒸鍍A1 為100nm來形成陰極，而製得有機EL元件。以發光亮度 321062 83 200948929 300(cd/m2)於室溫下對此元件進行定電流驅動後之色度， 為CIE(x，y) = (0. 17,〇. 17)的藍色發光，發光效率為 6.4cd/A。此外，並測定出以電流密度12.5mA/cm2進行驅 動時之初期亮度、以及於30°C的環境下連續驅動100小時 後之亮度。結果如第11表所示。 實施例143至159 除了使用第11表中的化合物來取代化合物131之 外，其他與實施例142相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 ❹ 率均為5cd/A以上。此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於30°C的環境下連續驅動 10 0小時後之亮度。結果如第11表所示。 比較例10至11 除了使用化合物S (比較例1 〇 )、下列化合物V (比較例 11)來取代化合物131之外，其他與實施例142相同來製作 出元件。測定出以發光亮度3〇〇(cd/m2)於室溫下對該元件 ❹ 進行定電流驅動時之發光效率。此外，並測定出以電流密 度12. 5mA/cm2進行驅動時之初期亮度、以及於3(TC的環境 下連續驅動1〇〇小時後之亮度。結果如第11表所示。❹ It can be seen from Table 10 that the compounds of the present invention have a longer life and a higher efficiency than the 7L pieces produced in Comparative Example 9. Example 142 Compound Q was vacuum-deposited on a glass plate with an IT crucible electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the compound ruthenium and the exemplary compound 131 were co-deposited at a composition ratio of 3:1 Torr to form a light-emitting layer having a film thickness of 40 nm. Thereafter, ruthenium was vapor-deposited to prepare an electron injection layer having a film thickness of 4 Å. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1 nm, and then vapor-depositing A1 to 100 nm to form a cathode. The chromaticity of the element after constant current driving at room temperature with a luminance of 321062 83 200948929 300 (cd/m2) is a blue luminescence of CIE(x, y) = (0.17. 17). The luminous efficiency was 6.4 cd/A. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 11. Examples 143 to 159 An element was produced in the same manner as in Example 142 except that the compound in Table 11 was used instead of the compound 131. When these elements were driven at a constant current of 300 (cd/m2) at room temperature, the luminous efficiency was 5 cd/A or more. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 30 hours in an environment of 30 ° C were measured. The results are shown in Table 11. Comparative Examples 10 to 11 An element was produced in the same manner as in Example 142 except that the compound S (Comparative Example 1 〇) and the following Compound V (Comparative Example 11) were used instead of the compound 131. The luminous efficiency when the element was driven at a constant current of 3 〇〇 (cd/m 2 ) at room temperature was measured. Further, the initial luminance at the time of driving with a current density of 10.5 mA/cm 2 and the luminance after continuous driving for 1 hour under a TC atmosphere were measured. The results are shown in Table 11.

84 321(J62 200948929 [第11表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 142 131 6.4 730 670 143 134 5.6 810 730 144 137 6.4 670 620 145 145 5.7 750 680 146 153 5.3 740 690 147 168 6.6 790 720 148 169 6.1 820 700 149 174 6.0 650 590 150 182 6.5 730 700 151 189 5.7 690 650 152 196 5.2 620 600 153 203 6.3 750 670 154 224 6.8 840 760 155 230 5.6 790 700 156 238 5.9 670 640 157 257 6.0 640 580 158 259 5.4 660 600 159 262 6.7 790 740 比較例 10 S 2.1 230 110 比較例 11 V 1.4 280 110 從第11表中可得知，本發明之化合物，均較比較例 10、11所製作之元件更具有長壽命且可獲得高效率。 實施例160 將化合物T真空蒸鍍於附有ITO電極的玻璃板上，而 製得膜厚65nm的電洞注入層。接著以3 : 100的組成比， 將化合物Η與化合物132予以共蒸鍍，而形成膜厚35nm 85 321062 200948929 的發光層。之後將TPBI予以蒸鍍而製得膜厚30nm的電子 注入層。於其上首先蒸鍍氟化鐘1ηπι，然後再蒸鑛μ為 lOOnm來形成陰極，而製得有機EL元件。以發光亮度 300(cd/m2)於室溫下對此元件進行定電流驅動後之色度， 為01£(又，7) = (〇.17，0.18)的藍色發光，發光效率為 6. 6cd/A。此外，並測定出以電流密度12. 5mA/cm2進行驅 動時之初期亮度、以及於30。(：的環境下連續驅動100小 時，接著再於100°C的環境下連續驅動24小時後之各種驅 動後之亮度。結果如第12表所示。 ❹ 實施例161至175 除了使用第12表中的化合物來取代化合物132之 外，其他與實施例160相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 率均為4cd/A以上，此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於30°C的環境下連續驅動 100小時，接著再於l〇〇°C的環境下連續驅動24小時後之 ^84 321 (J62 200948929 [Table 11] Example compound luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, luminance after 100 hours (cd/m 2 ) 142 131 6.4 730 670 143 134 5.6 810 730 144 137 6.4 670 620 145 153 5.7 750 680 146 153 5.3 740 690 147 168 6.6 790 720 148 169 6.1 820 700 149 174 6.0 650 590 150 182 6.5 730 700 151 189 5.7 690 650 152 196 5.2 620 600 153 203 6.3 750 670 154 224 6.8 840 760 155 230 5.6 790 700 156 238 5.9 670 640 157 257 6.0 640 580 158 259 5.4 660 600 159 262 6.7 790 740 Comparative example 10 S 2.1 230 110 Comparative example 11 V 1.4 280 110 It can be seen from Table 11 that the compounds of the present invention have a longer life and higher efficiency than the elements produced in Comparative Examples 10 and 11. Example 160 Vacuum evaporation of Compound T to ITO On the glass plate of the electrode, a hole injection layer having a film thickness of 65 nm was obtained, and then the compound ruthenium and the compound 132 were co-deposited at a composition ratio of 3:100 to form a light-emitting layer having a film thickness of 35 nm 85 321062 200948929. After that, TPBI is evaporated. An electron injecting layer having a film thickness of 30 nm was obtained, and an organic EL device was formed by first vapor-depositing a fluorination clock 1 η πι and then vaporizing the μ to 100 nm to form an organic EL device with a luminance of 300 (cd/m 2 ). The chromaticity of the element after the current is driven by the constant current is 0.1 £ (also, 7) = (〇.17, 0.18) of blue light emission, and the luminous efficiency is 6.6 cd/A. The initial luminance at the time of driving at a current density of 12.5 mA/cm2, and the luminance after various driving after continuous driving for 100 hours in an environment of 30 ° C, and then continuously driving for 24 hours in an environment of 100 ° C. As shown in Table 12. 实施 Examples 161 to 175 The elements were produced in the same manner as in Example 160 except that the compound in Table 12 was used instead of Compound 132. The luminous efficiency when these elements were driven at a constant current of 300 (cd/m 2 ) at room temperature was 4 cd/A or more, and the initial luminance when driving at a current density of 12.5 mA/cm 2 was measured. And continuously driving for 100 hours in an environment of 30 ° C, followed by continuous driving for 24 hours in a l ° ° C environment ^

Q 各種驅動後之亮度。結果如第12表所示。 比較例12至13 除了使用化合物S(比較例12)、化合物V(比較例13) 來取代化合物132之外，其他與實施例160相同來製作出 元件。測定出以發光亮度300(cd/m2)於室溫下對該元件進 行定電流驅動時之發光效率。此外，並測定出以電流密度 12. 5mA/cm2進行驅動時之初期亮度、以及於30°C的環境下 連續驅動100小時，接著再於l〇〇°C的環境下連續驅動24 86 321062 200948929 ❹ 小時後之各種ϋ動後之亮度。結果如第12表所示 [第12表]Q Brightness after various drivers. The results are shown in Table 12. Comparative Examples 12 to 13 In the same manner as in Example 160, except that the compound S (Comparative Example 12) and the compound V (Comparative Example 13) were used instead of the compound 132, an element was produced. The luminous efficiency when the element was driven at a constant current with a luminance of 300 (cd/m2) at room temperature was measured. In addition, the initial brightness at the time of driving at a current density of 12.5 mA/cm 2 and the continuous driving for 100 hours in an environment of 30 ° C were measured, followed by continuous driving in an environment of 10 ° C., 32 86 321062 200948929亮度 The brightness after various hours of turbulence. The results are shown in Table 12 [Table 12]

從第12表中可得知，本發明之化合物，均較比較例 12、13所製作之元件，更可獲得具有長壽命且高效率、高 耐熱性之元件。 實施例17 6 將化合物Κ蒸鐘於附有ΙΤ0電極的玻璃板上，而製得 膜厚70nm的電洞注入層。接著以1〇〇 : 8的組成比，將第 1表的化合物133與化合物L予以共蒸鍍，而形成骐厚6〇nm 的發光層。之後將Balq予以蒸鍍而製得膜厚15nm的電洞 321062 87 200948929 阻止層，然後於其上將Alq3予以真空蒸鍍而製得膜厚40nm 的電子注入層，於其上首先蒸鍍氟化鐘1 nm，然後再蒸鍍 A1為200nm來形成電極，而製得有機EL元件。以發光亮 度300(cd/m2)於室溫下對此元件進行定電流驅動時，係顯 現出藍色發光，發光效率為10. 3cd/A。 實施例177至181 除了使用第13表中的化合物來取代化合物133之 外，其他與實施例176相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 率均為9cd/A以上。結果如第13表所示。 [第13表] 實施例 化合物 發光效率 (cd/A) 176 133 10. 3 177 138 9. 9 178 146 12.5 179 178 11.8 180 199 9. 3 181 208 10. 7 實施例182 以旋轉塗佈法使？£0017?33(聚（3,4-伸乙二氧基）-2, 5-噻吩/聚苯乙烯磺酸、Bayer公司製BAYTRON P VP CH8000)成膜於洗淨後之附有ΙΤ0電極的玻璃板上，而製得 膜厚60nm的電洞注入層。接著以2. Owt%的濃度，將60 %的PVK(聚乙烯咔唑）、5%的化合物183及36%的電子傳 88 321062 200948929 輸材料（化合物N)溶解於甲苯，並藉由旋轉塗佈法而製得 膜厚50nm的發光層。之後於其上蒸鍍Ca為2〇nm後，再蒸 鍍A1為200nm來形成電極，而製得有機EL元件。對此元 件進行通電試驗時，可獲得最大發光亮度為830cd/m2的藍 色發光。 實施例183 以旋轉塗佈法使？£0017?85(聚（3,4-伸乙二氧 基）-2, 5-噻吩/聚苯乙稀續酸、Bayer公司製BAYTR0NPVP ❹ CH8000)成膜於洗淨後之附有ITO電極的玻璃板上，而製得 膜厚50nm的電洞注入層。接著以2_ Owt%的濃度，將60 %的PVK(聚乙烯咔唑）、5%的化合物218及35%的電子傳 輸材料（化合物0)溶解於曱苯，並藉由旋轉塗佈法而製得 膜厚60mn的發光層。之後於其上蒸鍍Ca為20nm後，再蒸 鍍A1為200nm來形成電極，而製得有機EL元件。對此元 件進行通電試驗時，可獲得最大發光亮度為680cd/m2的藍 ❹ 色發光。 實施例184 將化合物278真空蒸鍍於洗淨後之附有ΙΤ0電極的玻 璃板上，而製得膜厚40nm的電洞注入層。接著將化合物（A) 予以真空蒸鑛而製得膜厚40mn的電洞傳輸層。再將Aiq3 予以真空蒸鍍而製得膜厚40nm的電子注入型發光層，於其 上首先蒸鑛氟化鋰lnm ’然後再蒸鍵A1為200nm來形成電 極’而製得有機EL元件。對此元件進行通電試驗時，可獲 得最大發光亮度為1960cd/m2的黃色發光。 321062 89 200948929 實施例185 將化合物Q蒸鍵於附有ΙΤ0電極的破璃板上，形成膜 厚40nm的電洞注入層後，將化合物218予以蒸鍍而形成膜 厚40nm的電洞傳輸層。接著將Aiq3予以蒸鍍而形成膜厚 30nm的電子注入性發光層’於其上首先蒸鍍氟化鋰lnm， 然後再藉由真空蒸鑛形成A1為200nm來形成電極，而製得 有機EL元件。對此元件進行通電試驗時，可獲得最大發光 亮度為1670cd/m2的黃色發光。 實施例186 將化合物Q真空蒸鍍於附有ΙΤ0電極的玻璃板上，形 成膜厚70nm的電洞注入層。接著將Aiq3予以蒸鍍而形成 膜厚30nm的發光層。然後將化合物208予以蒸鍍而形成膜 厚30nm的電子注入層。於其上首先蒸鍍氟化鋰1ηπι，然後 再藉由蒸鐘形成Α1為lOOnm來形成陰極，而製得有機el 元件。對此元件進行通電試驗時，可獲得最大發光亮度為 1490cd/m2的黃色發光。 實施例187 除了使用化合物226來取代化合物208之外，其他與 實施例186相同而製作出元件。對此元件進行通電試驗 時，可獲得最大發光亮度為1620cd/m2的黃色發光。 實施例188 將a -NPD真空蒸鍍於洗淨後之附有IT0電極的玻璃板 上，而製得膜厚60nm的電洞注入層。接著將化合物306 予以真空蒸鍍而製得膜厚30nm的發光層。之後將TPBI予 90 321062 200948929 以真空蒸鐘而製得膜厚3〇nm的電子注入層，於其上、 鍍氟化鋰lnm，然後再蒸鍍A1為150nm來形成電極，蒸 得有機EL元件。以發光亮度300(cd/m2)於室溫下對此^ 件進行定電流驅動時之發光效率為2. 9cd/A。此外，並測 定出以電流密度12. 5mA/cm2進行驅動時之初期亮度、以及 於30C的環境下連續驅動1〇〇小時後之亮度。結果如第 表所示。 實施例189至204 © 除了使用第14表中的化合物來取代化合物306而製 作出發光層之外，其他與實施例188相同來製作出元件。 測定出以發光亮度300(cd/m2)於室溫下對此元件進行定電 流驅動時之效率。此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於30°C的環境下連續驅動 100小時後之亮度。結果如第14表所示。 比較例14 除了使用下列所示之化合物W來取代化合物306而製 作出發光層之外，其他與實施例188相同來製作出元件。 測定出以發光亮度300(cd/m2)於室溫下對此元件進行定電 流驅動時之效率。此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於3(TC的環境下連續驅動 100小時後之亮度。結果如第14表所示。 91 321062 200948929As is apparent from the table 12, the compounds of the present invention are more capable of obtaining elements having a long life, high efficiency, and high heat resistance as compared with the elements produced in Comparative Examples 12 and 13. Example 17 6 A compound was crucible and steamed on a glass plate to which a ΙΤ0 electrode was attached to prepare a hole injection layer having a film thickness of 70 nm. Next, the compound 133 of the first table and the compound L were co-deposited at a composition ratio of 1 〇〇:8 to form a light-emitting layer having a thickness of 6 Å. Then, Balq was vapor-deposited to obtain a hole with a thickness of 15 nm, 32106 87 200948929, and then Alq3 was vacuum-deposited thereon to obtain an electron injecting layer having a film thickness of 40 nm, and firstly vapor-deposited thereon. The organic EL element was produced by forming an electrode by a clock of 1 nm and then vapor-depositing A1 to 200 nm. The illuminating efficiency is 10.3 cd/A, when the illuminating light is transmitted at a constant current of 300 cd/m2 at room temperature. Examples 177 to 181 Other components were produced in the same manner as in Example 176 except that the compound in Table 13 was used instead of Compound 133. When these elements were driven at a constant current of 300 (cd/m2) at room temperature, the luminous efficiency was 9 cd/A or more. The results are shown in Table 13. [Table 13] Example compound Luminous efficiency (cd/A) 176 133 10. 3 177 138 9. 9 178 146 12.5 179 178 11.8 180 199 9. 3 181 208 10. 7 Example 182 by spin coating ? £0017?33 (poly(3,4-exetylenedioxy)-2, 5-thiophene/polystyrenesulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer Co., Ltd.) was formed into a film with a ΙΤ0 electrode attached thereto. On the glass plate, a hole injection layer having a film thickness of 60 nm was obtained. Then, at a concentration of 2.0% by weight, 60% of PVK (polyvinylcarbazole), 5% of compound 183, and 36% of electrons were transferred to toluene by spin coating. A light-emitting layer having a film thickness of 50 nm was obtained by a method. Thereafter, after Ca was vapor-deposited to 2 Å, the electrode was formed by further vapor-depositing A1 to 200 nm to prepare an organic EL device. When the component was subjected to the energization test, blue light having a maximum luminance of 830 cd/m2 was obtained. Example 183 by spin coating method? £0017?85 (poly(3,4-exetylenedioxy)-2, 5-thiophene/polystyrene acid, BAYTR0NPVP ❹ CH8000 manufactured by Bayer Co., Ltd.) film-formed with ITO electrode On the glass plate, a hole injection layer having a film thickness of 50 nm was obtained. Then, 60% of PVK (polyvinylcarbazole), 5% of compound 218 and 35% of electron transporting material (compound 0) were dissolved in toluene at a concentration of 2_wt%, and were prepared by spin coating. A light-emitting layer having a film thickness of 60 nm was obtained. Thereafter, after Ca was vapor-deposited at 20 nm, an electrode was formed by further vapor-depositing A1 to 200 nm to prepare an organic EL device. When the component was subjected to a power-on test, blue illuminance with a maximum luminance of 680 cd/m2 was obtained. Example 184 A compound 278 was vacuum-deposited on a glass plate with a ruthenium electrode attached thereto to prepare a hole injection layer having a film thickness of 40 nm. Next, the compound (A) was subjected to vacuum distillation to obtain a hole transport layer having a film thickness of 40 nm. Further, Aiq3 was vacuum-deposited to obtain an electron injecting type light-emitting layer having a film thickness of 40 nm, and an organic EL device was obtained by first vaporizing lithium fluoride 1 nm' and then steaming the bond A1 to 200 nm to form an electrode'. When the element was subjected to a current test, a yellow light having a maximum light emission luminance of 1960 cd/m2 was obtained. 321062 89 200948929 Example 185 A compound Q was vapor-deposited on a glass plate with a ΙΤ0 electrode to form a hole injection layer having a thickness of 40 nm, and then a compound 218 was vapor-deposited to form a hole transport layer having a film thickness of 40 nm. Then, Aiq3 was vapor-deposited to form an electron-injecting light-emitting layer having a film thickness of 30 nm, on which first, lithium fluoride was deposited, and then an electrode was formed by vacuum evaporation to form an electrode to form an electrode, thereby preparing an organic EL device. . When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1670 cd/m2 was obtained. Example 186 Compound Q was vacuum-deposited on a glass plate with a ΙΤ0 electrode to form a hole injection layer having a film thickness of 70 nm. Next, Aiq3 was vapor-deposited to form a light-emitting layer having a film thickness of 30 nm. Then, the compound 208 was vapor-deposited to form an electron injecting layer having a film thickness of 30 nm. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1 η πι and then forming a cathode by forming a Α1 of 100 nm by a steaming bell. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1490 cd/m2 was obtained. Example 187 An element was produced in the same manner as in Example 186 except that the compound 226 was used instead of the compound 208. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1620 cd/m2 was obtained. Example 188 A-NPD was vacuum-deposited on a cleaned glass plate with an ITO electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the compound 306 was subjected to vacuum evaporation to obtain a light-emitting layer having a film thickness of 30 nm. Then, TPBI was applied to 90 321062 200948929 to obtain an electron injecting layer having a thickness of 3 〇 nm by vacuum evaporation, on which lithium fluoride was plated at 1 nm, and then A1 was 150 nm to form an electrode, and an organic EL device was evaporated. . The illuminating efficiency is 2. 9 cd/A when the illuminating efficiency is 2.9 cd/A. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 1 hour in an environment of 30 C were measured. The results are shown in the table. Examples 189 to 204 © The same procedures as in Example 188 were carried out except that the compound of Table 14 was used instead of Compound 306 to prepare a light-emitting layer. The efficiency at which the element was subjected to constant current driving at room temperature with a luminance of 300 (cd/m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C were measured. The results are shown in Table 14. Comparative Example 14 An element was produced in the same manner as in Example 188 except that the compound W shown below was used instead of the compound 306 to prepare a light-emitting layer. The efficiency at which the element was subjected to constant current driving at room temperature with a luminance of 300 (cd/m2) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 3 hours in a TC environment were measured. The results are shown in Table 14. 91 321062 200948929

[第14表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 188 306 2.9 510 440 189 293 2.4 320 270 190 307 3.2 480 440 191 309 3.5 560 500 192 316 3.8 540 480 193 319 2.1 340 280 194 333 2.4 340 270 195 343 2.9 460 360 196 354 2.5 400 340 197 361 2.8 520 470 198 376 4.0 550 510 199 377 3. 7 490 460 200 388 3. 4 370 320 201 395 3. 6 410 320 202 408 2. 3 300 260 203 430 3. 7 460 430 204 434 4.1 480 440 比較例 14 W 0.4 60 15 從第14表中可得知，本發明之化合物，均較比較例 14所製作之元件更具有長壽命且可獲得高效率。 實施例205 92 321062 200948929 將化合物Q真空蒸鍍於附有IT〇電極的玻璃板上，而 製得膜厚80nm的電洞注入層。接著以3 : 1〇〇的組成比， 將第1表之例示化合物308與化合物R予以共蒸鍍，而形 成膜厚35nm的發光層。之後將TPBI予以蒸鍍而形成膜厚 35nm的電子注入層。於其上首先蒸鍍氟化鋰lnm ,然後再 蒸鍍A1為lOOnm來形成陰極，而製得有機el元件。以發 光売度300(cd/m2)於室溫下對此元件進行定電流驅動後之 色度，為CIE(x，y)=(0· 12, 0. 13)的藍色發光，發光效率為 〇 5. 8cd/A。此外，並測定出以電流密度i2.5mA/cm2進行驅 動時之初期亮度、以及於30。(：的環境下連續驅動1〇〇小時 後之亮度。結果如第15表所示。 實施例206至220 除了使用第15表中的化合物來取代例示化合物3 0 8 之外，其他與實施例205相同來製作出元件。這些元件在 以發光亮度300(cd/m2)於室溫下進行定電流驅動後之發光 q 色，係顯現出藍色，且發光效率均為5cd/A以上。此外， 並測定出以電流密度12. 5mA/cm2進行驅動時之初期亮度、 以及於30°C的環境下連續驅動1〇〇小時後之亮度。結果如 第15表所示。 比較例15至16 除了使用化合物W(比較例15)、下列化合物X(比較例 16)來取代化合物308之外’其他與實施例205相同來製作 出元件。測定出以發光亮度300(cd/m2)於室溫下對這些元 件進行定電流驅動時之發光效率。此外’並測定出以電流 93 321062 200948929 密度12. 5mA/cm2進行驅動時之初期亮度、以及於30°C的環 境下連續驅動100小時後之亮度。結果如第15表所示。[Table 14] Example compound luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, luminance after 100 hours (cd/m 2 ) 188 306 2.9 510 440 189 293 2.4 320 270 190 307 3.2 480 440 191 309 3.5 560 500 192 316 3.8 540 480 193 319 2.1 340 280 194 333 2.4 340 270 195 343 2.9 460 360 196 354 2.5 400 340 197 361 2.8 520 470 198 376 4.0 550 510 199 377 3. 7 490 460 200 388 3. 4 370 320 201 395 3. 6 410 320 202 408 2. 3 300 260 203 430 3. 7 460 430 204 434 4.1 480 440 Comparative example 14 W 0.4 60 15 From table 14 It can be seen that the compounds of the present invention have a longer life and higher efficiency than the elements produced in Comparative Example 14. Example 205 92 321062 200948929 Compound Q was vacuum-deposited on a glass plate with an IT crucible electrode to prepare a hole injection layer having a film thickness of 80 nm. Next, the exemplified compound 308 of the first table and the compound R were co-deposited at a composition ratio of 3:1 Torr to form a light-emitting layer having a film thickness of 35 nm. Thereafter, TPBI was vapor-deposited to form an electron injecting layer having a film thickness of 35 nm. On this, an organic el element was obtained by first vapor-depositing lithium fluoride 1 nm, and then vapor-depositing A1 to 100 nm to form a cathode. The chromaticity of the element after constant current driving at room temperature with a luminance of 300 (cd/m2) is blue light emission of CIE (x, y) = (0·12, 0.13), luminous efficiency 〇 5. 8cd/A. Further, the initial luminance at the time of driving at a current density of i2.5 mA/cm 2 was measured, and 30 was measured. The brightness was continuously driven for 1 hour in the environment of (: The results are shown in Table 15. Examples 206 to 220 Other than the examples except that the compound in Table 15 was used instead of the exemplified compound 3 0 8 The elements were produced in the same manner as in 205. These elements exhibited a blue color and a luminous efficiency of 5 cd/A or more after being subjected to a constant current driving at a room temperature of 300 (cd/m 2 ) at room temperature. The initial luminance at the time of driving at a current density of 10.5 mA/cm 2 and the luminance after continuous driving for 1 hour at 30 ° C were measured. The results are shown in Table 15. Comparative Examples 15 to 16 An element was produced in the same manner as in Example 205 except that the compound W (Comparative Example 15) and the following Compound X (Comparative Example 16) were used instead of the compound 308. The luminance was 300 (cd/m 2 ) at room temperature. The luminous efficiency at the time of constant current driving of these elements was measured. Further, the initial luminance at the time of driving with a current of 93 321062 200948929 density of 12. 5 mA/cm 2 and the continuous driving for 100 hours in an environment of 30 ° C were measured. Brightness. The result is as the 15th Fig.

[第15表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮度 (cd/m2) 205 297 5.8 770 710 206 304 5.1 570 540 207 306 6.1 740 700 208 318 5.6 790 730 209 327 5.4 690 640 210 339 5.9 740 680 211 346 6.2 700 620 212 357 5.3 640 540 213 359 5.6 680 630 214 364 5.5 710 640 215 379 5.4 650 570 216 392 5.2 660 580 217 405 5.8 640 560 218 413 5.4 640 570 219 433 5.6 670 600 220 434 5.7 690 650 比較例15 W 0.8 180 100 比較例16 X 1.3 240 50 從第15表中可得知，本發明之化合物，均較比較例 15及16所製作之元件，更具有長壽命且可獲得高效率。 實施例221 94 321062 200948929[Table 15] Example compound Luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, luminance after 100 hours (cd/m 2 ) 205 297 5.8 770 710 206 304 5.1 570 540 207 306 6.1 740 700 208 318 5.6 790 730 209 327 5.4 690 640 210 339 5.9 740 680 211 346 6.2 700 620 212 357 5.3 640 540 213 359 5.6 680 630 214 364 5.5 710 640 215 379 5.4 650 570 216 392 5.2 660 580 217 405 5.8 640 560 218 413 5.4 640 570 219 433 5.6 670 600 220 434 5.7 690 650 Comparative example 15 W 0.8 180 100 Comparative example 16 X 1.3 240 50 As can be seen from Table 15, the compounds of the invention Compared with the components produced in Comparative Examples 15 and 16, it has a longer life and high efficiency. Example 221 94 321062 200948929

將化合物τ真空蒸鑛於附有L 電極的破璃板上，而 製得膜厚60mn的電洞注入層。接芸丨v 设考从100 : 3的重量组成 比，將化合物R與例示化合物307 + ^ # M共秦链，而形成膜 厂旱3〇舢的發光層。之後將化合物B予以蒸鍍而形成膜厚 3〇nm的電子注入層。於其上首先蒸鍍Lh。為 蒸鍍A1為100nm來形成陰極，而製^ _ ,„ 于有機el元件。此元 件在以發光亮度300(cd/m )於室溫下、* / p遵行定電流驅動後之 發光色，係顯現出藍色，且發光效康炎 〇 卞馬b. 3cd/A。此外， ϋ測定出以電流密度i2. 5mA/cm2進行驅動時之初期… 以及於3(TC的環境下連續驅動1〇M、時後之亮度。結^如 第16表所示。 實施例222至237 除了使用第16表中的化合物來取代化合物3〇7之 外，其他與實施例221相同來製作出元件。這些元件在以 發光党度300(cd/m )於室溫下進行定電流驅動後之發光 ❹色，均顯現出藍色，且發光效率均為5C(j/a以上，此外， 並測定出以電流密度12. 5mA/cm2進行驅動時之初期亮度、 以及於30C的環境下連續驅動1〇〇小時後之亮度。結果如 第16表所示。 比較例17 除了使用化合物X來取代化合物307之外，其他與實 施例221相同來製作出元件。測定出以發光亮度300(cd/m2) 於室溫下對該元件進行定電流驅動時之發光效率。此外， 並測定出以電流密度12. 5mA/cm2進行驅動時之初期亮度、 95 321062 200948929 以及於30°C的環境下連續驅動100小時後之亮度。結果如 第16表所示。 [第16表] 實施例 化合物 發光效率 (cd/A) 發光色 電流密度12. 5raA/cm2 初期亮度 (cd/m2) 30°C、100小時後之 亮度 (cd/m2) 221 307 6.3 藍色 620 540 222 295 5.4 藍色 550 480 223 308 5.7 藍色 670 590 224 320 5. 1 藍色 590 510 225 336 5.9 藍色 620 540 226 338 5.2 藍色 610 510 227 350 5.4 藍色 660 580 228 362 6.2 藍色 720 640 229 366 6.0 藍色 700 610 230 370 5.8 藍色 640 570 231 374 6.2 藍色 690 660 232 380 5.5 藍色 610 570 233 384 5.4 藍色 660 600 234 390 5.8 藍色 680 620 235 398 5.1 藍色 610 530 236 402 6.3 藍色 750 680 237 417 5.6 藍色 650 570 比較例17 X 1.2 水色 200 70 從第16表中可得知，本發明之化合物，均較比較例 17所製作之元件，更顯現出色純度高之藍色，具有長壽命 且可獲得高效率。 實施例238 將化合物Q真空蒸鍍於附有ΙΤ0電極的玻璃板上，而 製得膜厚60nm的電洞注入層。接著以3 : 100的組成比， % 321062 200948929 Λ 將化合物Η與例示化合物306予以共蒸鍍，而形成膜厚 40nm的發光層。之後將ΤΡΒΙ予以蒸鍍而製得膜厚40rm的 電子注入層。於其上首先蒸鍍氟化鋰1ηιη，然後再蒸鍍A1 為lOOnm來形成陰極，而製得有機EL元件。以發光亮度 300(cd/m2)於室溫下對此元件進行定電流驅動時，係顯現 出藍色發光，且發光效率為6. 5cd/A。此外，並測定出以 電流密度12. 5mA/cm2進行驅動時之初期亮度、以及於30 °C的環境下連續驅動1〇〇小時後之亮度。結果如第17表所 〇 示。:... 實施例239至251 除了使用第17表中的化合物來取代化合物306之 外，其他與實施例238相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 率均為5cd/A以上’此外’並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於3〇。匸的環境下連續驅動 φ 100小時後之亮度。結果如第17表所示。 比較例18至19 除了使用化合物X(比較例18)、下列化合物Y(比較例 19)來取代化合物306之外，其他與實施例238相同來製作 出元件。測定出以發光亮度3〇〇(cd/m2)於室溫下對該元件 進行疋電流驅動時之發光效率。此外，並測定出以電流密 度12.5mA/cm2進行驅動時之初期亮度、以及於30。(：的環境 下連續驅動1〇〇小時後之亮度。結果如第17表所示。 97 321062 200948929The compound τ was vacuum-steamed on a glass plate with an L electrode to prepare a hole injection layer having a film thickness of 60 nm. The 芸丨v design is based on a weight ratio of 100:3, and the compound R is combined with the exemplified compound 307 + ^ # M to form a luminescent layer of the membrane plant. Thereafter, the compound B was vapor-deposited to form an electron injecting layer having a film thickness of 3 〇 nm. Lh was first evaporated thereon. The electrode is formed by vapor-depositing A1 to 100 nm, and the organic EL element is produced. The element is driven by a constant current driven at a room temperature of 300 (cd/m) at a room temperature of */p. It is blue, and the luminescence effect is b. 3cd/A. In addition, ϋ is measured at the initial stage when the current density is i2. 5mA/cm2... and continuous driving in 3 (TC environment) 〇M, the brightness after the time. The structure is as shown in Table 16. Examples 222 to 237 The elements were produced in the same manner as in Example 221 except that the compound in Table 16 was used instead of the compound 3〇7. These elements showed blue color when they were driven by a constant current of 300 (cd/m) at room temperature, and the luminous efficiency was 5 C (j/a or more, and was measured. The initial luminance at the time of driving at a current density of 10.5 mA/cm 2 and the luminance after continuous driving for 1 hour in an environment of 30 C. The results are shown in Table 16. Comparative Example 17 In place of the compound 307 except the compound X was used. The other components were produced in the same manner as in Example 221, and the luminance was 300 (c). d/m2) luminous efficiency at constant current driving of the device at room temperature. Further, initial luminance at a current density of 12.5 mA/cm2, 95 321062 200948929, and an environment at 30 ° C were measured. The brightness was continuously driven for 100 hours. The results are shown in Table 16. [Table 16] Example compound luminous efficiency (cd/A) Luminescent current density 12. 5 raA/cm2 Initial luminance (cd/m2) 30° C, brightness after 100 hours (cd/m2) 221 307 6.3 blue 620 540 222 295 5.4 blue 550 480 223 308 5.7 blue 670 590 224 320 5. 1 blue 590 510 225 336 5.9 blue 620 540 226 338 5.2 Blue 610 510 227 350 5.4 Blue 660 580 228 362 6.2 Blue 720 640 229 366 6.0 Blue 700 610 230 370 5.8 Blue 640 570 231 374 6.2 Blue 690 660 232 380 5.5 Blue 610 570 233 384 5.4 Blue 660 600 234 390 5.8 Blue 680 620 235 398 5.1 Blue 610 530 236 402 6.3 Blue 750 680 237 417 5.6 Blue 650 570 Comparative Example 17 X 1.2 Aqua 200 70 As can be seen from Table 16, The compounds of the present invention are all produced in comparison with Comparative Example 17. Elements, show more excellent high purity of blue, having a long life and high efficiency can be obtained. Example 238 Compound Q was vacuum-deposited on a glass plate with a ΙΤ0 electrode to prepare a hole injection layer having a film thickness of 60 nm. Next, the compound ruthenium and the exemplified compound 306 were co-evaporated at a composition ratio of 3:100, % 321062 200948929 , to form a light-emitting layer having a film thickness of 40 nm. Thereafter, ruthenium was vapor-deposited to prepare an electron injection layer having a film thickness of 40 rm. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1ηιη, and then vapor-depositing A1 to 100 nm to form a cathode. The illuminating efficiency is 6. 5 cd/A, when the illuminating efficiency is 6. 5 cd/A. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 and the luminance after continuous driving for 1 hour at 30 ° C were measured. The results are shown in Table 17. :... Examples 239 to 251 An element was produced in the same manner as in Example 238 except that the compound in Table 17 was used instead of the compound 306. The luminous efficiency when these elements were driven at a constant current of 300 (cd/m2) at room temperature was 5 cd/A or more, and the initial luminance at the time of driving at a current density of 12.5 mA/cm2 was measured. And 3 〇. The brightness of φ after 100 hours is continuously driven in a sturdy environment. The results are shown in Table 17. Comparative Examples 18 to 19 Components were produced in the same manner as in Example 238 except that Compound X (Comparative Example 18) and the following Compound Y (Comparative Example 19) were used instead of Compound 306. The luminous efficiency when the element was driven with xenon current at room temperature with a luminance of 3 〇〇 (cd/m 2 ) was measured. Further, the initial luminance at the time of driving at a current density of 12.5 mA/cm 2 was measured, and 30 was measured. The brightness after continuous driving for 1 hour in the environment of :. The result is shown in Table 17. 97 321062 200948929

化合物Υ [第17表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 (cd/m2) 30°C、100小時後之亮 度 (cd/m2) 238 306 6.5 820 740 239 292 5.1 620 510 240 303 5.4 660 580 241 309 6.6 790 740 242 310 5.8 760 690 243 317 6.3 800 700 244 345 5.3 640 580 245 358 6.1 790 750 246 367 6.3 800 730 247 370 5.9 740 660 248 373 6. 6 850 800 249 376 6.0 790 710 250 403 5.6 750 660 251 426 5.0 620 500 比較例18 X 1.7 210 80 比較例19 Y 0.9 130 20 從第17表中可得知，本發明之化合物，均較比較例 18、19所製作之元件更具有長壽命且可獲得高效率。 實施例252 將化合物Τ真空蒸鍍於附有ΙΤ0電極的玻璃板上，而 製得膜厚65nm的電洞注入層。接著以3 : 100的組成比， 98 321062 200948929 將化合物J與化合物307予以共蒸鍍，而形成膜厚35nm 的發光層。之後將TPBI予以蒸鍍而製得膜厚3〇nm的電子 注入層。於其上首先蒸鐘氟化鐘lnm，然後再蒸鐘A〗為 lOOnm來形成陰極，而製得有機EL元件。以發光亮度 300(cd/m2)於室溫下對此元件進行定電流驅動時之發光色 為藍色’發光效率為6. 8cd/A。此外，並測定出以電流密 度12.5mA/cm2進行驅動時之初期亮度、以及於3〇t：的環境 下連續驅動100小時，接著再於1〇〇它的環境下連續驅動 ® 24小時後之各種驅動後之亮度。結果如第18表所示。 實施例253至266 除了使用第18表所示之化合物來取代化合物3〇7之 外，其他與實施例252相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 率均為4cd/A以上，此外，並測定出以電流密度12. 5mA/cm2 進行驅動時之初期亮度、以及於3〇。(：的環境下連續驅動 ❹100小時’接著再於100°C的環境下連續驅動24小時後之 各種驅動後之亮度。結果如第18表所示。 比較例20至21 除了使用化合物X(比較例20)、化合物Y(比較例21) 來取代化合物307之外’其他與實施例252相同來製作出 元件。測定出以發光亮度300(C(i/m2)於室溫下對該元件進 行定電流驅動時之發光效率。此外，並測定出以電流密度 12. 5mA/cm2進行驅動時之初期亮度、以及於30。(：的環境下 連續驅動100小時’接著再於l〇〇°C的環境下連續驅動24 99 321062 200948929 小時後之各種驅動後之亮度。結果如第18表所示。 [第18表] 實施例 化合物 發光效率 (cd/A) 電流密度12. 5mA/cm2 初期亮度 Ccd/in2) 30°C、100小時後 之亮度 (cd/m2) 100°C、24小時後之 亮度 (cd/m2) 252 307 6.8 880 790 720 253 293 4.5 580 540 450 254 295 4. 9 590 550 490 255 309 5.9 730 640 590 256 316 6.4 800 740 680 257 318 6.0 820 760 700 258 323 5.1 680 620 510 259 350 5.3 640 560 430 260 363 4.5 550 510 400 261 367 5.3 730 650 580 262 372 4.9 620 540 430 263 378 5.7 740 640 510 264 395 5.3 680 600 520 265 404 6.6 870 800 730 266 425 6.2 790 720 570 比較例 20 X 1.5 190 60 未發光 比較例 21 Y 1.4 210 40 未發光 從第18表中可得知，本發明之化合物，均較比較例 20、21所製作之元件，更可獲得具有長壽命且高效率、高 财熱性之元件。 實施例267 將化合物K蒸鍍於附有ITO電極的玻璃板上，而製得 膜厚60nm的電洞注入層。接著以100 ·· 9的組成比，將第 1表的化合物315與化合物L予以共蒸鑛，而形成膜厚5 Onm 的發光層。之後將Balq予以蒸鍍而製得膜厚10nm的電洞 阻止層，然後於其上將Alq3予以真空蒸鍍而製得膜厚50nm 100 321062 200948929 的電子注入層，於其上首先蒸鍍氟化鋰lnm，然後再蒸鍍 A1為200nm來形成電極，而製得有機EL元件。以發光亮 度300(cd/m2)於室溫下對此元件進行定電流驅動時，係顯 現出藍色發光，發光效率為11.4cd/A。 實施例268至276 除了使用第19表中的化合物來取代化合物315之 外，其他與實施例267相同來製作出元件。將這些元件以 發光亮度300(cd/m2)於室溫下進行定電流驅動時之發光效 ❹ 率均為9cd/A以上。結果如第19表所示。 [第19表] 實施例 化合物 發光效率 (cd/A) 267 315 11.4 268 303 9. 5 269 316 10.8 270 326 9. 1 271 336 11.1 272 356 9. 9 273 363 9. 3 274 377 10. 7 275 401 11.4 276 403 10. 9 實施例277 以旋轉塗佈法使？£0077?33(聚（3,4-伸乙二氧基）-2, 5-噻吩/聚苯乙烯磺酸、Bayer公司製BAYTRON P VP CH8000)成膜於洗淨後之附有ΙΤ0電極的玻璃板上，而製得 膜厚50nm的電洞注入層。接著以2. 5wt%的濃度，將60 101 321062 200948929 %的^^(聚乙烯咔唑）、5%的化合物373及36%的電子傳 輸材料（化合物N)溶解於甲苯，並藉由旋轉塗佈法而製得 膜厚40ηιη的發光層。之後於其上蒸鍍以為別⑽後，再蒸 鍍A1為200nm來形成電極，而製得有機乩元件。對此元 件進行通電試驗時，可獲得最大發光亮度為㈣㈤化2)的 藍色發光。 實施例278 以旋轉塗佈法使PED0T/PSS (聚（3，4-伸乙二氧 基）2,5嗟％/聚本乙稀續酸、Bayer公司.製.baytr〇NPVP CH800G)成聽洗淨後謂有ITQt_坡魏上，而製得 膜厚50nm的電洞注入層。接著以2.5wt%的濃度，將6〇 %的PVK(聚乙烯咔唑）、5%的化合物381及35%的電子傳 輸材料（化合物0)溶解於甲苯，並藉由旋轉塗佈法而製得 膜厚50nm的發光層。之後於其上蒸鍍以為2〇胍後，再蒸 鍍A1為200nm來形成電極，而製得有機EL元件。對此元 件進行通電試驗時，可獲得最大發光亮度為68〇(cd/m2)的 藍色發光。 實施例279 將本發明之化合物310真空蒸鍍於洗淨後之附有I το 電極的玻璃板上，而製得膜厚50nm的電洞注入層。接著將 化合物A予以真空蒸鍍而製得膜厚5〇nm的電洞傳輸層。再 將Alq3予以真空絡鍍而製得膜厚5〇nm的電子注入型發光 層，於其上首先蒸鍍氟化鋰lnm，然後再蒸鍍Ai為2〇〇nm 來形成電極，而製得有機EL元件。對此元件進行通電試驗 ^321062 102 200948929 钂 時，可獲得最大發光亮度為2570(cd/m2)的黃色發光。 實施例280至282 除了使用第20表所示之化合物來取代化合物310之 外，其他與實施例279相同而製作出元件。第20表係顯示 對這些元件進行通電試驗時之最大發光亮度。 [第20表] 實施例 化合物 最大發光亮度 (cd/m2) 279 310 2570 280 317 2410 281 375 2960 282 384 2660 實施例283 將化合物Q蒸鍍於附有ITO電極的玻璃板上，形成膜 厚30mn的電洞注入層後，將化合物312予以蒸鍍而形成膜 厚50nm的電洞傳輸層。接著將Alq3予以蒸鍍而形成膜厚 40nm的電子注入性發光層，於其上首先蒸鍍氟化鋰lnm， 〇 然後再藉由真空蒸鍍形成A1為200nm來形成電極，而製得 有機EL元件。對此元件進行通電試驗時，可獲得最大發光 亮度為1950(cd/m2)的黃色發光》 實施例284至286 除了使用第21表所示之化合物來取代化合物312之 外，其他與實施例283相同而製作出元件。第21表係顯示 對這些元件進行通電試驗時之最大發光亮度。 103 321062 200948929 [第21表] 實施例 化合物 最大發光亮度 (cd/m2) 283 312 1950 284 314 2340 285 354 2620 286 405 2240 實施例287 將化合物Q真空蒸鍍於附有ΙΤ0電極的玻璃板上，形 成膜厚40nm的電洞注入層。接著將Alq3予以蒸鍍而形成 膜厚40nm的發光層。然後將化合物311予以蒸鍍而形成膜 厚30nm的電子注入層。於其上首先蒸鍍氟化鋰lnm，然後 再藉由蒸鍍形成A1為lOOnm來形成陰極，而製得有機EL 元件。對此元件進行通電試驗時，可獲得最大發光亮度為 1690(cd/m2)的黃色發光。 實施例288至293 除了使用第22表所示之化合物來取代化合物311之 外，其他與實施例287相同而製作出元件。第22表係顯示 對這些元件進行通電試驗時之最大發光亮度。 104 321062 200948929 [第22表] 實施例 化合物 最大發光亮度 (cd/m2) 287 311 1690 288 326 2040 289 332 1530 290 342 2760 291 343 1940 292 382 2640 293 397 3050 從以上所述之實施例中可得知，使用本發明之有機EL 元件用材料的有機EL元件，可達成發光效率的提升及長壽 命化。 【圖式簡單說明】無 【主要元件符號說明】無 ◎ 105 321062Compound Υ [Table 17] Example compound Luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial luminance (cd/m2) 30 ° C, brightness after 100 hours (cd/m 2 ) 238 306 6.5 820 740 239 292 5.1 620 510 240 303 5.4 660 580 241 309 6.6 790 740 242 310 5.8 760 690 243 317 6.3 800 700 244 345 5.3 640 580 245 358 6.1 790 750 246 367 6.3 800 730 247 370 5.9 740 660 248 373 6. 6 850 800 249 376 6.0 790 710 250 403 5.6 750 660 251 426 5.0 620 500 Comparative Example 18 X 1.7 210 80 Comparative Example 19 Y 0.9 130 20 As can be seen from Table 17, the compounds of the present invention were compared with Comparative Example 18. The components produced in 19 have a long life and high efficiency. Example 252 A compound was poured on a glass plate with a ΙΤ0 electrode under vacuum to obtain a hole injection layer having a film thickness of 65 nm. Next, Compound J and Compound 307 were co-evaporated at a composition ratio of 3:100, 98 321062 200948929 to form a light-emitting layer having a film thickness of 35 nm. Thereafter, TPBI was vapor-deposited to obtain an electron injecting layer having a film thickness of 3 Å. On top of this, an organic EL element was obtained by first steaming a fluorination clock of 1 nm, and then steaming a clock A to be 100 nm to form a cathode. The illuminating color is 6. 8 cd/A when the illuminating color of the light-emitting element is 3.7 cd/A. In addition, the initial brightness at the time of driving at a current density of 12.5 mA/cm 2 and the continuous driving for 3 hours in an environment of 3 〇 t: and then continuously driving in an environment of 1 ® for 24 hours were measured. The brightness of various drivers. The results are shown in Table 18. Examples 253 to 266 Other elements were produced in the same manner as in Example 252 except that the compound shown in Table 18 was used instead of the compound 3〇7. The luminous efficiency when these elements were driven at a constant current of 300 (cd/m 2 ) at room temperature was 4 cd/A or more, and the initial luminance when driving at a current density of 12.5 mA/cm 2 was measured. And 3 〇. The brightness of various driving after continuous driving for ❹100 hours in the environment of :: and then continuously driving for 24 hours in an environment of 100 ° C. The results are shown in Table 18. Comparative Examples 20 to 21 except that Compound X was used (Comparative Example 20), Compound Y (Comparative Example 21) An element was produced in the same manner as in Example 252 except for the compound 307. The element was measured at a luminance of 300 (C (i/m2) at room temperature. The luminous efficiency at the time of constant current driving. The initial luminance at the time of driving at a current density of 12.5 mA/cm 2 was measured, and the driving was continued for 30 hours in an environment of (the environment was continued for 100 hours). The brightness of various driving after 24 99 321062 200948929 hours was continuously driven. The results are shown in Table 18. [Table 18] Example compound luminous efficiency (cd/A) Current density 12. 5 mA/cm2 Initial brightness Ccd/in2) 30 ° C, brightness after 100 hours (cd/m2) 100 ° C, brightness after 24 hours (cd/m2) 252 307 6.8 880 790 720 253 293 4.5 580 540 450 254 295 4. 9 590 550 490 255 309 5.9 730 640 590 256 316 6.4 800 740 680 257 318 6.0 820 760 700 258 323 5.1 680 620 510 259 350 5.3 640 560 430 260 363 4.5 550 510 400 261 367 5.3 730 650 580 262 372 4.9 620 540 430 263 378 5.7 740 640 510 264 395 5.3 680 600 520 265 404 6.6 870 800 730 266 425 6.2 790 720 570 Comparative Example 20 X 1.5 190 60 Non-emissive Comparative Example 21 Y 1.4 210 40 No luminescence As can be seen from Table 18, the compounds of the present invention were all compared with the components produced in Comparative Examples 20 and 21. Further, an element having a long life, high efficiency, and high heat efficiency can be obtained. Example 267 A compound K was deposited on a glass plate with an ITO electrode to prepare a hole injection layer having a film thickness of 60 nm. The composition ratio of 9 was co-steamed with the compound 315 of the first table and the compound L to form a light-emitting layer having a film thickness of 5 Onm, and then Balq was vapor-deposited to obtain a hole blocking layer having a film thickness of 10 nm. Then, Alq3 was vacuum-deposited thereon to obtain an electron injecting layer having a film thickness of 50 nm, 100 321062 and 200948929, on which lithium fluoride was first evaporated to a thickness of 1 nm, and then A1 was evaporated to form an electrode to form an electrode. EL component. When the element was subjected to constant current driving at room temperature with a luminance of 300 (cd/m2), blue light emission was exhibited, and the luminous efficiency was 11.4 cd/A. Examples 268 to 276 An element was produced in the same manner as in Example 267 except that the compound in Table 19 was used instead of the compound 315. When these elements were driven at a constant current of 300 (cd/m2) at room temperature, the luminous efficiency was 9 cd/A or more. The results are shown in Table 19. [Table 19] Example compound Luminous efficiency (cd/A) 267 315 11.4 268 303 9. 5 269 316 10.8 270 326 9. 1 271 336 11.1 272 356 9. 9 273 363 9. 3 274 377 10. 7 275 401 11.4 276 403 10. 9 Example 277 by spin coating? £0077?33 (poly(3,4-exetylenedioxy)-2, 5-thiophene/polystyrenesulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer Co., Ltd.) was formed into a film with a ΙΤ0 electrode attached thereto. On the glass plate, a hole injection layer having a film thickness of 50 nm was obtained. Then, at a concentration of 2.5 wt%, 60 101 321062 200948929% of the (polyvinylcarbazole), 5% of the compound 373, and 36% of the electron transporting material (Compound N) were dissolved in toluene and spin coated. A light-emitting layer having a film thickness of 40 ηηη was obtained by a cloth method. Thereafter, after vapor-depositing thereon (10), the electrode was formed by further vapor-depositing A1 to 200 nm to prepare an organic germanium element. When the component is energized, the blue illuminance with the maximum illuminance of (4) (five) 2) can be obtained. Example 278 PED0T/PSS (poly(3,4-exoethylenedioxy) 2,5嗟%/polyethyl benzoate, Bayer Corporation.baytr〇NPVP CH800G) was made by spin coating. After washing, there is an ITQt_Slope, and a hole injection layer with a film thickness of 50 nm is obtained. Then, 6 wt% of PVK (polyvinylcarbazole), 5% of compound 381, and 35% of an electron transporting material (compound 0) were dissolved in toluene at a concentration of 2.5 wt%, and were prepared by spin coating. A light-emitting layer having a film thickness of 50 nm was obtained. Thereafter, after vapor deposition for 2 Å, an electrode was formed by further vapor-depositing A1 to 200 nm to prepare an organic EL device. When this component is energized, a blue luminescence with a maximum luminance of 68 〇 (cd/m2) can be obtained. Example 279 The compound 310 of the present invention was vacuum-deposited on a glass plate with an I το electrode attached thereto to prepare a hole injection layer having a film thickness of 50 nm. Next, the compound A was subjected to vacuum evaporation to obtain a hole transport layer having a film thickness of 5 Å. Then, Alq3 was vacuum-plated to obtain an electron-injection-type light-emitting layer having a film thickness of 5 〇 nm, and firstly, lithium fluoride was deposited thereon to a thickness of 1 nm, and then Ai was evaporated to 2 nm to form an electrode. Organic EL element. When the element was subjected to a power-on test ^321062 102 200948929 黄色, a yellow light having a maximum light-emitting luminance of 2570 (cd/m 2 ) was obtained. Examples 280 to 282 An element was produced in the same manner as in Example 279 except that the compound shown in Table 20 was used instead of the compound 310. Table 20 shows the maximum luminance of the light when these components are energized. [Table 20] Maximum luminous luminance (cd/m2) of the compound of the example 279 310 2570 280 317 2410 281 375 2960 282 384 2660 Example 283 The compound Q was evaporated on a glass plate with an ITO electrode to form a film thickness of 30 nm. After the hole injection layer, the compound 312 was vapor-deposited to form a hole transport layer having a film thickness of 50 nm. Next, Alq3 was vapor-deposited to form an electron injecting light-emitting layer having a thickness of 40 nm, and first, lithium fluoride was deposited thereon to a thickness of 1 nm, and then an electrode was formed by vacuum evaporation to form an electrode of 200 nm to form an organic EL. element. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1950 (cd/m 2 ) was obtained. Examples 284 to 286 Except that the compound shown in Table 21 was used instead of the compound 312, and Example 283 The components are produced in the same way. Table 21 shows the maximum luminance of the light when these components are energized. 103 321062 200948929 [Table 21] Maximum luminous luminance of the compound of the example (cd/m2) 283 312 1950 284 314 2340 285 354 2620 286 405 2240 Example 287 Compound Q was vacuum-deposited on a glass plate with a ΙΤ0 electrode, A hole injection layer having a film thickness of 40 nm was formed. Next, Alq3 was vapor-deposited to form a light-emitting layer having a film thickness of 40 nm. Then, the compound 311 was vapor-deposited to form an electron injecting layer having a film thickness of 30 nm. On this, an organic EL element was obtained by first vapor-depositing lithium fluoride 1 nm, and then forming a cathode by vapor deposition to form A1 to be 100 nm. When the element was subjected to a current test, yellow light having a maximum light emission luminance of 1690 (cd/m2) was obtained. Examples 288 to 293 An element was produced in the same manner as in Example 287 except that the compound shown in Table 22 was used instead of the compound 311. Table 22 shows the maximum luminance of the light when these components are energized. 104 321062 200948929 [Table 22] Example compounds Maximum luminescence brightness (cd/m2) 287 311 1690 288 326 2040 289 332 1530 290 342 2760 291 343 1940 292 382 2640 293 397 3050 Available from the examples described above It is known that the organic EL device using the material for an organic EL device of the present invention can achieve an improvement in luminous efficiency and a long life. [Simple diagram description] None [Main component symbol description] None ◎ 105 321062

Claims (1)

200948929 1. 七、申請專利範圍： 般式 二種有機t場料藉肖 [1]所表示之化合物： -特徵為由下列 Ar4 Ar3-ArWXV_Ar2- R1 -般式[1] 惟，式中’ 分別獨立地 :芳香〜是取代或—::::200948929 1. VII. Scope of application for patents: Compounds of the general two kinds of organic t-field materials [1]: - characterized by the following Ar4 Ar3-ArWXV_Ar2-R1 - general formula [1] Independently: Aroma ~ is a replacement or -:::: Ar3為取代絲取代_合料族 取代的縮合芳香麵環基； 〜取代或未 或是取代 Ar4為氫原子、取代或未取代的芳香族煙基、 或未取代的芳香族雜環基； X為s、o、或^紅5,在此，Ar5為取代或未取代的― 香族烴基、或是取代或未取代的芳香族雜環基；方Ar3 is a substituted fused-aromatic group-substituted condensed aromatic ring-shaped ring group; ～substituted or unsubstituted or substituted Ar4 is a hydrogen atom, a substituted or unsubstituted aromatic smoky group, or an unsubstituted aromatic heterocyclic group; Is s, o, or ^ red 5, wherein Ar5 is a substituted or unsubstituted "aromatic hydrocarbon group" or a substituted or unsubstituted aromatic heterocyclic group; R及R为別獨立地為風原子、取代或未取代的广基 取代或未取代的芳香族煙基、取代或未取代的芳香族 環基、取代或未取代的烷氧基、或是取代或未取代的芳 氧基，且R1及R2可鍵結而形成環。 2. —種有機電場發光元件，係在由陽極與陰極所成之—對 電極間，形成一廣或多層的有機層而成之有機電場發光 元件，其中，至少1層為含有申請專利範圍第1項之有 機電場發光元件用材料的層。 3. 如申請專利範圍第2項之有機電場發光元件，其中，人 321062 106 200948929 有申請專利範圍第1項之有機電場發光元件用材料的 層為發光層。 4. 如申請專利範圍第3項之有機電場發光元件，其中，含 有申請專利範圍第1項之有機電場發光元件用材料作 為發光層主材料。 5. 如申請專利範圍第2項之有機電場發光元件，其中，含 有申請專利範圍第1項之有機電場發光元件用材料的 層為電子傳輸層。 107 321062 9 200948929 三、英文發明摘要： Provided is a material for organic electro-luminescence element whicli is a compound represented by the following general-formula [1].R and R are independently a halogen atom, a substituted or unsubstituted broad-group substituted or unsubstituted aromatic fluorenyl group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted alkoxy group, or a substitution. Or an unsubstituted aryloxy group, and R1 and R2 may be bonded to form a ring. 2. An organic electric field light-emitting element, which is an organic electric field light-emitting element formed by forming an organic layer of a wide or multiple layers between a pair of electrodes formed by an anode and a cathode, wherein at least one layer contains the patent application scope A layer of a material for an organic electric field light-emitting element of one item. 3. The organic electroluminescent device of claim 2, wherein the layer of the material for the organic electroluminescent device of claim 1 is a light-emitting layer. 4. The organic electroluminescent device of claim 3, wherein the material for the organic electroluminescent device of claim 1 is used as the main material of the light-emitting layer. 5. The organic electroluminescent device of claim 2, wherein the layer of the material for the organic electroluminescent device of claim 1 is an electron transport layer. 107 321062 9 200948929 III. Summary of the invention: Provided is a material for organic electro-luminescence element whicli is a compound represented by the following general-formula [1]. Ar2—Ar^ —般式[1] (wherein Ar1 and Ar2 respectively independently represents substituted or unsubstituted divalent aromatic hydrocarbon group, or substituted or unsubstituted divalent aromatic heterocyclic group,Wherein Ar1 and Ar2 respective independently represented or unsubstituted divalent aromatic hydrocarbon group, or substituted or unsubstituted divalent aromatic heterocyclic group, Ar3 represents substituted or unsubstituted condensed aromatic hydrocarbon group, or substituted or unsubstituted condensed aromatic heterocyclic group, Ar4 represents hydrogen atom, substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group, X represents S, O or N-Ar5, wherein Ar5 represents substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group, R1 and R2 respectively independently represents hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted alkoxy group, or substituted or unsubstituted aiyloxy group wherein R1 and R2 may couple to each other to form a ring.) ’ 四、指定代表圖：本案無圖式 (一) 本案指定代表圖為：第（）圖。 (二) 本代表圖之元件符號簡單說明：Ar3 represents substituted or unsubstituted condensed aromatic hydrocarbon group, or substituted or unsubstituted condensed aromatic heterocyclic group, Ar4 represents hydrogen atom, substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group, X represents S, O or N-Ar5, Alternate or unsubstituted aromatic heterocyclic group, substituted or unsubstituted alkyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted alkoxy Group, or substituted or unsubstituted aiyloxy group, R1 and R2 may couple to each other to form a ring.) ' IV. Designated representative map: There is no schema in this case (1) The representative representative figure in this case is: (). (2) A brief description of the symbol of the representative figure: 五、本案若有化學式時，請揭示最能顯示發明特徵的化學式 一般式[1] Ai^-Ar1·-^ X V-Ar2—Αι4 R1 R2 321062 25. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention. General formula [1] Ai^-Ar1·-^ X V-Ar2—Αι4 R1 R2 321062 2
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