TW201817707A - Novel compound and organic electroluminescent device including the same - Google Patents

Novel compound and organic electroluminescent device including the same Download PDF

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TW201817707A
TW201817707A TW106136265A TW106136265A TW201817707A TW 201817707 A TW201817707 A TW 201817707A TW 106136265 A TW106136265 A TW 106136265A TW 106136265 A TW106136265 A TW 106136265A TW 201817707 A TW201817707 A TW 201817707A
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unsubstituted
compound
aryl
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咸昊完
安賢哲
姜京敏
裵惟珍
金東駿
閔丙哲
金槿泰
李螢振
林東煥
林大喆
權桐熱
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南韓商東進世美肯股份有限公司
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Abstract

To provide a novel compound and roganic electroluminescent device.

Description

新穎化合物及包含其的有機發光裝置Novel compound and organic light emitting device containing the same

本發明涉及新穎化合物及包含其的有機發光裝置。The present invention relates to a novel compound and an organic light emitting device including the same.

在有機發光二極體中，用作有機層的材料可根據功能大致分類為發光材料、電洞注入材料、電洞傳輸材料、電子傳輸材料、電子注入材料等。並且，上述發光材料可根據分子量分類為高分子和低分子，可根據發光原理分類為來源於電子的單態激發狀態的螢光材料和來源於電子的三態激發狀態的磷光材料，發光材料可根據發光色分類為藍色、綠色、紅色發光材料和體現更好的天然色所需的黃色及橙色發光材料。並且，為了增加色純度，並藉由能量轉移增加發光效率，可將主體/摻雜劑類用作發光物質。其原理為若將與主要構成發光層的主體相比，能帶隙小且發光效率優秀的摻雜劑少量混合於發光層中，則在主體中產生的激子向摻雜劑傳輸，從而發出效率高的光。此時，主體的波長向摻雜劑的波長帶移動，因而可根據利用的摻雜劑和主體的種類獲得所需的波長的光。In the organic light emitting diode, materials used as an organic layer can be roughly classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to functions. In addition, the above luminescent materials can be classified into high molecular and low molecules according to molecular weight, and can be classified into fluorescent materials in a single-state excitation state derived from electrons and phosphorescent materials in a three-state excitation state derived from electrons according to the principle of light emission. They are classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials required for better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host / dopant can be used as a light-emitting substance. The principle is that if a small amount of a dopant with a small band gap and excellent luminous efficiency is mixed with the light emitting layer compared to the main body that mainly constitutes the light emitting layer, excitons generated in the host are transmitted to the dopant, thereby emitting Efficient light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used and the host.

至今，作為使用於這種有機發光裝置的物質，眾所周知的有多種化合物，但在利用至今眾所周知的物質的有機發光裝置的情況下，由於高的驅動電壓、低的效率及短壽命，持續要求開發新的材料。因此，持續努力利用具有優秀的特性的物質來開發具有低電壓驅動、高亮度及長壽命的有機發光裝置。Heretofore, as a substance used in such an organic light-emitting device, various compounds are well known. However, in the case of an organic light-emitting device using a conventionally well-known substance, development has been continuously demanded due to high driving voltage, low efficiency, and short life. New material. Therefore, efforts are continuously being made to develop organic light-emitting devices with low-voltage driving, high brightness, and long life using substances with excellent characteristics.

習知技術文獻：日本公開專利10-2015-530735。Conventional technical literature: Japanese Laid-Open Patent No. 10-2015-530735.

本發明提供新穎有機化合物及其製備方法以及包含其的有機發光裝置。The present invention provides a novel organic compound, a method for preparing the same, and an organic light-emitting device including the same.

但是，本發明所要解決的問題不局限於以上描述的問題，本發明所屬技術領域具有通常知識者可根據以下的記載內容明確地理解未描述的其他問題。However, the problems to be solved by the present invention are not limited to the problems described above, and those with ordinary knowledge in the technical field to which the present invention pertains can clearly understand other problems not described based on the following description.

化學式1在上述化學式1中，R1 為氫、重氫、C1 -C6 烷基或C6 -C30 的芳基；Ar1 至Ar4 分別獨立地為取代或未取代的C6 -C30 芳基、取代或未取代的C10 -C25 縮合芳基或取代或未取代的C5 -C30 雜芳基，上述Ar3 及Ar4 能夠相互形成或不形成環；L為連接基團，其是選自單鍵、C6 -C30 伸芳基或C5 -C30 伸雜芳基；Ar為取代或未取代的C6 -C10 芳基、取代或未取代的C10 -C25 縮合芳基或取代或未取代的C5 -C30 雜芳基，l為1至4的整數，m為1至3的整數。Chemical formula 1 In the above Chemical Formula 1, R 1 is hydrogen, deuterium, C 1 -C 6 alkyl or C 6 -C 30 aryl; Ar 1 to Ar 4 are each independently substituted or unsubstituted C 6 -C 30 Ar, substituted or unsubstituted C 10 -C 25 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, the above Ar 3 and Ar 4 can form or not form a ring with each other; L is a linking group , Which is selected from a single bond, C 6 -C 30 aryl or C 5 -C 30 heteroaryl; Ar is substituted or unsubstituted C 6 -C 10 aryl, substituted or unsubstituted C 10- C 25 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, l is an integer of 1 to 4, and m is an integer of 1 to 3.

本發明的第二實施方式，提供包含本發明的化合物的有機發光裝置。A second embodiment of the present invention provides an organic light-emitting device including the compound of the present invention.

本發明是用苯基取代的二芳基芴和包含苯基及縮合芳基的芳胺來形成容易注入及傳輸電洞的最高佔有分子軌道（HOMO），並藉由取代二芳基芴部來維持高的最低未佔有分子軌道（LUMO），以容易阻隔電子，因此藉由使發光層內激子有效形成來實現了高效率有機發光裝置。並且，與胺相結合的芳基中的一部分導入碳原子數為6～10個的芳基或縮合芳基，因此分子的薄膜及介面排列優秀，從而可藉由快速的電洞移動率（hole mobility）來抑制滾降現象，並實現長壽命裝置，且在較小分子量的芳胺中，也可維持高的Tg，從而可防止薄膜的再結晶化來增加驅動穩定性。The present invention uses a phenyl substituted diarylfluorene and an arylamine containing a phenyl group and a condensed aryl group to form a highest occupied molecular orbital (HOMO) that can easily inject and transport holes, and replaces the diarylfluorene moiety Maintaining a high minimum unoccupied molecular orbital (LUMO) to easily block electrons, therefore, by efficiently forming excitons in the light emitting layer, a highly efficient organic light emitting device is realized. In addition, a part of the aryl group bonded to the amine is introduced with an aryl group having 6 to 10 carbon atoms or a condensed aryl group. Therefore, the molecular thin film and the interface arrangement are excellent, and the fast hole mobility (hole) mobility) to suppress the roll-off phenomenon and achieve a long-life device, and also maintain a high Tg in the smaller molecular weight aromatic amines, thereby preventing recrystallization of the film to increase driving stability.

本發明的化合物具有高的發光效率、高的色純度等的效果，從而適用於有機發光裝置、太陽能發電用有機光裝置等，由此可大大地貢獻於柔性顯示器、照明設備等的有機發光二極體（OLED）產業。The compounds of the present invention have effects such as high luminous efficiency and high color purity, and are therefore suitable for use in organic light-emitting devices, organic light-emitting devices for solar power generation, and the like, thereby greatly contributing to organic light-emitting devices such as flexible displays and lighting equipment. Polaroid (OLED) industry.

以下，參照附圖，詳細說明本發明的實例及實施例，使得本發明所屬技術領域具有通常知識者可容易實施。Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the drawings, so that those skilled in the art to which the present invention pertains can easily implement.

但是，本發明能夠以多種不同的形態實現，且不局限於在此說明的實例及實施例。並且，在圖中，為了明確說明本發明，省略了與說明無關的部分，在說明書全文中，對於類似的部分，標注了類似的附圖標記。However, the present invention can be implemented in many different forms, and is not limited to the examples and embodiments described herein. Moreover, in the drawings, in order to clearly explain the present invention, parts irrelevant to the description are omitted, and throughout the specification, similar parts are marked with similar reference numerals.

在本發明說明書全文中，當一個部件位於另一部件「上」時，不僅包括一個部件與另一部件相接觸的情況，還包括在兩個部件之間存在其他部件的情況。Throughout the description of the present invention, when a component is "on" another component, it includes not only the case where one component is in contact with another component, but also the case where other components are present between the two components.

在本發明說明書全文中，當一個部分「包括」一個結構要素時，除非有特別相反的記載，則意味著還可包括其他結構要素，而不是排除其他結構要素。在本發明說明書全文中使用的術語「約」、「實質上」等在所提及的含義上提示固有的製備及物質容差時以其數值或接近於其數值的含義使用，以防止昧良心的侵權人不當地利用為了幫助理解本發明而提及準確或絕對的數值的公開內容。在本發明說明書全文中使用的術語「～（的）步驟」或「～的步驟」不意味著「用於～的步驟」。Throughout the description of the present invention, when a part “includes” a structural element, unless there is a special contrary description, it means that other structural elements may also be included instead of excluding other structural elements. The terms "about", "substantially" and the like used throughout the specification of the present invention are used in their meanings to indicate inherent preparation and material tolerances in their numerical values or meanings close to their numerical values in order to prevent conscience. The infringer improperly makes use of disclosures that refer to exact or absolute numerical values in order to help understand the present invention. The terms "~ (step)" or "~ step" used throughout the present specification do not mean "step for ~".

在本發明說明書全文中，馬庫西（Markush）形式的表現中所含的「這些的組合」這一術語意味著選自由馬庫西形式的表現中所記載的多個結構要素組成的組中的一種以上的混合或組合，意味著包括選自由上述多個結構要素組成的組中的一種以上。Throughout the description of the present invention, the term "combination of these" included in the expression of the Markush form means that it is selected from the group consisting of a plurality of structural elements described in the expression of the Markush form A mixture or combination of more than one means that it includes one or more selected from the group consisting of the plurality of structural elements.

在本發明說明書全文中，「A和/或B」這一記載意味著「A或B，或者A及B」。Throughout the description of the present invention, the expression "A and / or B" means "A or B, or A and B".

在本發明說明書全文中，術語「芳基」意味著包含C6 -C30 的芳香族烴環基，例如，苄基、苯基、萘基、聯苯基、三聯苯基、芴基、菲基、三苯基烯基、苯基烯基、䓛基、熒烷噻吩甲基、苯並芴基、苯並三苯基烯基、苯並屈基、蒽基、均二苯乙烯基、芘基等的芳香族環；「雜芳基」作為包含至少一個雜元素的芳香族環，例如，意味著包含吡咯啉基、吡嗪基、吡啶基、吲哚基、異吲哚基、呋喃基、苯並呋喃基、異苯並呋喃基、二苯並呋喃基、苯並苯硫基、二苯並苯硫基、喹啉基、異喹啉基、喹喔啉基、哢唑基、菲唳基、吖啶基、菲咯啉基、噻吩基及由吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吲哚環、喹啉環、吖啶環、吡咯烷環、二噁烷環、呱啶環、嗎啉環、呱嗪環、哢唑環、呋喃環、噻吩環、噁唑環、噁二唑環、苯並噁唑環、噻唑環、噻重氮環、苯並噻唑環、三唑環、咪唑環、苯並咪唑環、吡喃環、二苯並呋喃環形成的芳香族雜環基。Throughout this specification, the term "aryl" means an aromatic hydrocarbon ring group containing C 6 -C 30 , such as benzyl, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthrene Base, triphenylalkenyl, phenylalkenyl, fluorenyl, fluoranthienyl, benzofluorenyl, benzotriphenylenyl, benzopentyl, anthracenyl, homostilbyl, fluorene Aromatic rings such as radicals; "heteroaryl" as an aromatic ring containing at least one hetero element, for example, means a pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl group , Benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzophenylthio, dibenzophenylthio, quinolinyl, isoquinolinyl, quinoxalinyl, oxazolyl, phenanthrene Fluorenyl, acridinyl, phenanthroline, thienyl, and pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, quinoline, acridine, pyrrolidine, Dioxane ring, pyrimidine ring, morpholine ring, oxazine ring, oxazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazonium ring, And a thiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a furan group dibenzo aromatic heterocyclic ring formed.

在本發明說明書全文中，術語「烷基」可包含直鏈或支鏈的飽和或不飽和的C1 -C6 烷基，例如，可包含甲基、乙基、丙基、丁基、戊基、己基或這些可能的所有同分異構體，但有可能不局限於此。In the specification of the present invention, the term "alkyl" may include saturated or unsaturated, linear or branched C 1 -C 6 alkyl chain, for example, may include methyl, ethyl, propyl, butyl, pentyl Group, hexyl group or all possible isomers of these, but it is possible to be not limited thereto.

在本發明說明書全文中，在術語「取代或未取代的」中，「取代」意味著可由選自由重氫、鹵素、氨基、腈基、硝基或C1 -C20 的烷基、C2 -C20 的烯基、C1 -C20 的烷氧基、C3 -C20 的環烷基、C3 -C20 的雜環烷基、C6 -C30 的芳基及C5 -C30 的雜芳基組成的組中的一種以上的基取代。In the specification of the present invention, the term "substituted or unsubstituted", the "substituted" means that may be selected from the group consisting of heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group or a C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 3 -C 20 cycloalkyl, C 3 -C 20 heterocycloalkyl, C 6 -C 30 aryl, and C 5- One or more groups in the group consisting of C 30 heteroaryl are substituted.

並且，在本發明說明書全文中，除非有特殊提及，相同的記號則可具有相同的含義。In addition, throughout the specification of the present invention, unless otherwise mentioned, the same symbols may have the same meaning.

本發明的第一實施方式，提供由以下化學式1表示的化合物。A first embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

化學式1在上述化學式1中，R1 為氫、重氫、C1 -C6 烷基或C6 -C30 的芳基，Ar1 至Ar4 分別獨立地為取代或未取代的C6 -C30 芳基、取代或未取代的C6 -C30 縮合芳基或取代或未取代的C5 -C30 雜芳基，上述Ar3 及Ar4 能夠相互形成或不形成環，L為連接基團，其是選自單鍵C6 -C30 伸芳基或C5 -C30 伸雜芳基；Ar為取代或未取代的C6 -C10 芳基、取代或未取代的C10 -C25 縮合芳基或取代或未取代的C5 -C30 雜芳基，l為1至4的整數，m為1至3的整數。Chemical formula 1 In the above Chemical Formula 1, R 1 is hydrogen, deuterium, C 1 -C 6 alkyl, or C 6 -C 30 aryl, and Ar 1 to Ar 4 are each independently substituted or unsubstituted C 6 -C 30 Ar, substituted or unsubstituted C 6 -C 30 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, the above Ar 3 and Ar 4 can form or not form a ring with each other, and L is a linking group , Which is selected from the group consisting of a single bond C 6 -C 30 aryl or C 5 -C 30 hetaryl; Ar is a substituted or unsubstituted C 6 -C 10 aryl, a substituted or unsubstituted C 10 -C 25 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, l is an integer from 1 to 4, and m is an integer from 1 to 3.

在本發明的一實例中，Ar3 和Ar4 可相結合來形成環，例如，可形成芴基。In an example of the present invention, Ar 3 and Ar 4 may be combined to form a ring, for example, a fluorenyl group may be formed.

在本發明的一實例中，在Ar為芳基的情況下，例如，可以為苯基等，在Ar為縮合芳基的情況下，可以為萘基、菲基、聯伸三苯等。由於這種取代基的限制，可形成高的最低未佔有分子軌道，並誘導使分子的薄膜及介面排列變得優秀，且在沉積製程中，能夠以低的溫度進行控制。In an example of the present invention, when Ar is an aryl group, for example, it may be a phenyl group, and when Ar is a condensed aryl group, it may be a naphthyl group, a phenanthryl group, or a triphenylene group. Due to the limitation of such substituents, a high minimum unoccupied molecular orbital can be formed, and the thin film and interface arrangement of the molecules can be induced to be excellent, and can be controlled at a low temperature during the deposition process.

在本發明的一實例中，上述化學式1的化合物可包含由以下化學式2或化學式3表示的化合物。In an example of the present invention, the compound of the above Chemical Formula 1 may include a compound represented by the following Chemical Formula 2 or Chemical Formula 3.

化學式2 Chemical formula 2

化學式3 Chemical formula 3

在上述化學式2及3中，Ar、Ar1 、Ar2 、Ar4 、L、l及m如在化學式1中所定義，R2 至R5 分別獨立地為氫、重氫、C1 -C6 烷基、C6 -C30 芳基或C5 -C30 雜芳基。In the above Chemical Formulas 2 and 3, Ar, Ar 1 , Ar 2 , Ar 4 , L, l, and m are as defined in Chemical Formula 1, and R 2 to R 5 are each independently hydrogen, deuterium, or C 1 -C. 6 alkyl, C 6 -C 30 aryl or C 5 -C 30 heteroaryl.

在本發明的一實例中，上述化合物可包含由以下化學式4或化學式5表示的化合物。In one embodiment of the present invention, the compound may include a compound represented by the following Chemical Formula 4 or Chemical Formula 5.

化學式4 Chemical formula 4

化學式5 Chemical formula 5

在上述化學式4及5中，Ar、R1 、l及m如在化學式1中所定義，R6 及R7 分別獨立地為氫、重氫或C1 -C6 烷基，R8 至R11 分別獨立地為氫、重氫、C1 -C6 烷基、C6 -C30 芳基或C5 -C30 雜芳基，Ar5 為取代或未取代的C6 -C30 芳基、取代或未取代的C6 -C30 縮合芳基或取代或未取代的C5 -C30 雜芳基，n為0至3的整數。In the above Chemical Formulas 4 and 5, Ar, R 1 , l, and m are as defined in Chemical Formula 1, R 6 and R 7 are each independently hydrogen, deuterium or C 1 -C 6 alkyl, and R 8 to R 11 are each independently hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 5 -C 30 heteroaryl, and Ar 5 is substituted or unsubstituted C 6 -C 30 aryl , Substituted or unsubstituted C 6 -C 30 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, n is an integer from 0 to 3.

在本發明的一實例中，上述化合物可包含以下化學式6或化學式7的化合物。In one embodiment of the present invention, the compound may include a compound of the following Chemical Formula 6 or Chemical Formula 7.

化學式6 Chemical formula 6

化學式7 Chemical formula 7

在上述化學式6及7中，Ar、R1 、l及m如在化學式1中所定義，R6 至R11 及Ar5 如在化學式4及化學式5中所定義。In the above Chemical Formula 6 and 7, Ar, R 1, l and m are as defined in Chemical Formula 1, R 6 to R 11 and Ar 5 are as defined in the Chemical Formula 4 and Chemical Formula 5.

在本發明的一實例中，在上述化學式1至化學式7中，Ar具體地可以為未取代的C6 -C10 芳基或未取代的C10 -C25 縮合芳基。In an example of the present invention, in the above Chemical Formulas 1 to 7, Ar may specifically be an unsubstituted C 6 -C 10 aryl group or an unsubstituted C 10 -C 25 condensed aryl group.

在本發明的一實例中，在上述化學式1至化學式7中，Ar可以為苯基或萘基。In an example of the present invention, in the above Chemical Formulas 1 to 7, Ar may be a phenyl group or a naphthyl group.

在本發明的一實例中，在上述化學式1至化學式7中，l可以為1，R1 可以為氫。In an example of the present invention, in the above Chemical Formulas 1 to 7, l may be 1, and R 1 may be hydrogen.

在本發明的一實例中，在上述化學式3、化學式5及化學式7中，R3 、R4 、R9 及R10 分別獨立地可以為氫、甲基或苯基。In an example of the present invention, in Chemical Formula 3, Chemical Formula 5, and Chemical Formula 7, R 3 , R 4 , R 9, and R 10 may each independently be hydrogen, methyl, or phenyl.

在本發明的一實例中，上述化學式1的化合物可按以下反應式1製備而成，但有可能不局限於此。In an example of the present invention, the compound of the above Chemical Formula 1 can be prepared according to the following Reaction Formula 1, but it may not be limited thereto.

反應式1 Reaction 1

在本發明的一實例中，上述有機發光化合物可包含以下具體化合物，但有可能不局限於此。In an example of the present invention, the organic light-emitting compound may include the following specific compounds, but may not be limited thereto.

在上述具體化合物中，以下的化合物可藉由將N直接耦合在至少一個芴基的第二位置來具有更快的電洞移動率，由此，可更降低驅動電壓，並更改善效率和壽命。Among the above specific compounds, the following compounds can have faster hole mobility by directly coupling N to the second position of at least one fluorene group, thereby reducing the driving voltage and improving efficiency and life .

並且，在上述具體化合物中，以下的化合物可藉由將L、伸苯基或N耦合在二芳基芴或二苯基芴基的第二位置來具有更快的電洞移動率，由此，可更降低驅動電壓，並更改善效率和壽命。In addition, among the above specific compounds, the following compounds can have faster hole mobility by coupling L, phenylene, or N to the second position of the diarylfluorene or diphenylfluorenyl group, thereby , Can reduce the driving voltage, and improve efficiency and life.

本發明的第二實施方式，提供包含由上述化學式1表示的化合物的有機發光裝置。上述有機發光裝置可在第一電極及第二電極之間包含含有本發明化合物的一層以上的有機層。A second embodiment of the present invention provides an organic light-emitting device including the compound represented by the aforementioned Chemical Formula 1. The organic light emitting device may include one or more organic layers containing the compound of the present invention between the first electrode and the second electrode.

在本發明的一實例中，上述有機層可以為電洞注入層、電洞傳輸層及發光輔助層中的一層以上，但有可能不局限於此，此時，本發明的化合物可單獨使用或與公知的有機發光化合物一同使用。In an example of the present invention, the organic layer may be more than one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, but may not be limited to this. In this case, the compound of the present invention may be used alone or It is used together with a known organic light emitting compound.

在本發明的一實例中，上述有機發光裝置可包括含有電洞傳輸物質的有機層及含有由上述化學式1表示的化合物的有機層，但有可能不局限於此。In an example of the present invention, the organic light-emitting device may include an organic layer containing a hole-transporting substance and an organic layer containing a compound represented by the above Chemical Formula 1, but it is not limited thereto.

上述有機發光裝置可在陽極（anode）和陰極（cathode）之間包括一個以上的電洞注入層（HIL）、電洞傳輸層（HTL）、發光層（EML）、電子傳輸層（ETL）、電子注入層（EIL）等的有機層。The above organic light emitting device may include more than one hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL) between the anode (anode) and cathode (cathode), An organic layer such as an electron injection layer (EIL).

例如，上述有機發光裝置可根據第1圖中所記載的結構來製備而成。有機發光裝置由下而上依次層疊陽極（電洞注入電極1000）/電洞注入層200/電洞傳輸層300/發光層400/電子傳輸層500/電子注入層600/陰極（電子注入電極2000）。For example, the organic light-emitting device can be prepared according to the structure described in FIG. 1. The organic light-emitting device has an anode (hole injection electrode 1000) / hole injection layer 200 / hole transmission layer 300 / light emitting layer 400 / electron transmission layer 500 / electron injection layer 600 / cathode (electron injection electrode 2000) stacked in order from bottom to top. ).

在第1圖中，基板100可使用用於有機發光裝置的基板，尤其，可以為機械強度、熱穩定性、透明性、表面平滑性、處理容易性及防水性優秀的透明的玻璃基板或可彎曲的塑膠基板。In FIG. 1, the substrate 100 may be a substrate for an organic light-emitting device. In particular, the substrate 100 may be a transparent glass substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Bent plastic substrate.

電洞注入電極1000用作用於注入有機發光裝置的電洞的陽極。為了可注入電洞，利用具有低的功函數的物質，可由氧化銦錫（ITO）、氧化銦鋅（IZO）、石墨烯（graphene）之類的透明的材質形成。The hole injection electrode 1000 functions as an anode for injecting holes into an organic light emitting device. In order to be able to inject holes, a substance having a low work function is used, and can be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

藉由真空沉積法、旋轉塗佈法、鑄造法、LB（Langmuir-Blodgett）法等來在上述陽極電極上部沉積電洞注入層物質，由此可形成電洞注入層200。在藉由上述真空沉積法來形成電洞注入層的情況下，其沉積條件因用作電洞注入層200的材料的化合物、所需電洞注入層的結構及熱特性等而不同，但通常可在50-500℃的沉積溫度、10-8 至10-3 托 (torr)的真空度、0.01至100Å/sec的沉積速度、10Å至5μm的層厚度範圍內適當地進行選擇。The hole injection layer 200 may be formed by depositing a hole injection layer material on the anode electrode by a vacuum deposition method, a spin coating method, a casting method, a LB (Langmuir-Blodgett) method, or the like. When the hole injection layer is formed by the vacuum deposition method described above, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the required hole injection layer, but usually It can be appropriately selected within the range of a deposition temperature of 50-500 ° C, a vacuum degree of 10 -8 to 10 -3 torr, a deposition speed of 0.01 to 100 sec / sec, and a layer thickness of 10 Å to 5 μm.

接著，藉由真空沉積法、旋轉塗佈法、鑄造法、LB法等來在上述電洞注入層200上部沉積電洞傳輸層物質，由此可形成電洞傳輸層300。在藉由上述真空沉積法來形成電洞傳輸層的情況下，其沉積條件因使用的化合物而不同，但通常，較佳地，在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。之後，藉由真空沉積法、旋轉塗佈法、鑄造法、LB法等來在上述電洞傳輸層上部沉積發光層物質，由此可形成發光層400。在藉由上述真空沉積法來形成發光層的情況下，其沉積條件因使用的化合物而不同，但通常，較佳地，在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。並且，上述發光層材料可將公知的化合物用作主體或摻雜劑。Then, a hole transport layer material is deposited on the hole injection layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, so that the hole transport layer 300 can be formed. In the case where the hole transport layer is formed by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer. . Thereafter, a light-emitting layer substance is deposited on the above hole transport layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, so that the light-emitting layer 400 can be formed. In the case where the light-emitting layer is formed by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer. The light-emitting layer material may use a known compound as a host or a dopant.

並且，在發光層中，與磷光摻雜劑一同使用的情況下，為了防止三態激子或電洞向電子傳輸層擴散的現象，藉由真空沉積法或旋轉塗佈法還可層疊電洞抑制材料（HBL）。此時可使用的電洞抑制物質不受特別的限制，但可從用作電洞抑制材料的公知的物質中選擇任意物質來利用。例如，可列舉惡二唑衍生物或三唑衍生物、菲咯啉衍生物或日本特開平11-329734（A1）中所記載的電洞抑制材料等，代表性地，可使用Balq（雙（8-羥基-2-甲基喹啉）-鋁聯苯酚鹽）、菲咯啉（phenanthrolines）類化合物（例如：通用顯示器（UDC）公司的BCP（Basso Coupoline））等。In addition, in the case of using together with a phosphorescent dopant in the light emitting layer, in order to prevent the diffusion of tri-state excitons or holes to the electron transport layer, holes may be laminated by a vacuum deposition method or a spin coating method. Inhibitory material (HBL). The hole-inhibiting substance that can be used at this time is not particularly limited, but any substance can be selected and used from known substances used as hole-inhibiting materials. For example, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, or a hole suppressing material described in Japanese Patent Application Laid-Open No. 11-329734 (A1) can be cited. Typically, Balq (bis (bis ( 8-hydroxy-2-methylquinoline) -aluminum biphenolate), phenanthrolines (for example: BCP (Basso Coupoline) of Universal Display (UDC)).

在如上形成的發光層400上部形成有電子傳輸層500，此時，上述電子傳輸層可藉由真空沉積法、旋轉塗佈法、鑄造法等方法來形成。並且，上述電子傳輸層的沉積條件因使用的化合物而不同，但通常，較佳地，在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。An electron transport layer 500 is formed on the light-emitting layer 400 formed as described above. At this time, the electron transport layer can be formed by a method such as a vacuum deposition method, a spin coating method, or a casting method. In addition, the deposition conditions of the above-mentioned electron transport layer differ depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer.

之後，可在上述電子傳輸層500上部沉積電子注入層物質來形成電子注入層600，此時，上述電子傳輸層可藉由真空沉積法、旋轉塗佈法、鑄造法等的方法來形成常規的電子注入層物質。Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form an electron injection layer 600. At this time, the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like to form a conventional Electron injection layer substance.

上述裝置的電洞注入層200、電洞傳輸層300、發光層400、電子傳輸層500可使用本發明的化合物或如下的物質，或者，可一同使用本發明的化合物和公知的物質。 The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the above device may use the compound of the present invention or the following substances, or may use the compound of the present invention and a known substance together.

藉由真空沉積法或濺射法等的方法來在電子注入層600上形成用於注入電子的陰極2000。作為陰極，可使用多種金屬。具體例子有鋁、金、銀等的物質。A cathode 2000 for injecting electrons is formed on the electron injection layer 600 by a method such as a vacuum deposition method or a sputtering method. As the cathode, various metals can be used. Specific examples include substances such as aluminum, gold, and silver.

本發明的有機發光裝置不僅可以採用陽極、電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層、陰極結構的有機發光裝置，還可採用多種結構的有機發光裝置的結構，根據需要，還可形成一層或兩層的中間層。The organic light-emitting device of the present invention can not only adopt an organic light-emitting device having an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or a cathode structure, but also a structure of an organic light-emitting device with various structures. As required, one or two intermediate layers can also be formed.

如上所述，根據本發明形成的各個有機層的厚度可根據所需的程度來進行調節，較佳地，具體為10至1000nm，更具體為20至150nm。As described above, the thickness of each organic layer formed according to the present invention can be adjusted according to a desired degree, preferably, specifically 10 to 1000 nm, and more specifically 20 to 150 nm.

並且，在本發明中，包含由上述化學式1表示的化合物的有機層可將有機層的厚度調節為分子單位，因而具有表面均勻且形態穩定性突出的優點。Further, in the present invention, the organic layer containing the compound represented by the above Chemical Formula 1 can adjust the thickness of the organic layer to a molecular unit, and thus has the advantages of uniform surface and outstanding morphological stability.

針對本實施方式的有機發光化合物，均可適用對於本發明的第一實施方式記載的內容，但有可能不局限於此。The organic light-emitting compound of this embodiment can be applied to the contents described in the first embodiment of the present invention, but it is not limited thereto.

實施例Examples

製備例1Preparation Example 1

IM的合成為了合成目的化合物，經過如上述反應式的步驟進行合成，以便準備IM。 以下IM1的合成法如下。Synthesis of IM In order to synthesize the target compound, it is synthesized through the steps of the above reaction formula to prepare IM. The following IM1 is synthesized as follows.

在圓底燒瓶中，在200ml的1,4-二惡烷中溶解15.0g的2-溴-9,9-二甲基-9H-芴及5.1g的苯基硼酸，並放入60ml的K2 CO3 （2M）和1.3g的Pd(PPh3 )4 之後，進行回流攪拌。藉由薄層層析法（TLC）確認反應，添加水後，結束反應。用二氯甲烷（MC）提取有機層，並進行減壓過濾之後，進行管柱純化來獲得了10.43g（回收率為63%）的中間體IM1-1。In a round bottom flask, dissolve 15.0 g of 2-bromo-9,9-dimethyl-9H-fluorene and 5.1 g of phenylboronic acid in 200 ml of 1,4-dioxane, and put 60 ml of K After 2 CO 3 (2M) and 1.3 g of Pd (PPh 3 ) 4 , the mixture was stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC). After adding water, the reaction was terminated. The organic layer was extracted with dichloromethane (MC) and filtered under reduced pressure, followed by column purification to obtain 10.43 g (recovery rate: 63%) of Intermediate IM1-1.

利用如上述IM1的方法，改變起始物質來合成了以下IM2至IM4。 為了合成目的化合物，經過如上述反應式的步驟進行合成，以便準備OP。 以下OP1的合成法如下。 Using the method of IM1 described above, the following IM2 to IM4 were synthesized by changing the starting materials. In order to synthesize the target compound, it is synthesized through the steps of the above reaction formula to prepare OP. The following OP1 synthesis method is as follows.

在圓底燒瓶中，在150ml的甲苯中溶解10.0g的2-溴-9,9-二苯基-9H-芴、3.8g的苯胺、5.3g的t-BuONa、1.4g的Pd2 (dba)3 及1.6ml的(t-Bu)3 P之後，進行回流攪拌。藉由薄層層析法來確認反應，添加水之後，結束反應。用二氯甲烷（MC）提取有機層，並進行減壓過濾之後，進行管柱純化及再結晶，從而獲得了7.73g（回收率為74%）的OP1。In a round-bottomed flask, 10.0 g of 2-bromo-9,9-diphenyl-9H-fluorene, 3.8 g of aniline, 5.3 g of t-BuONa, and 1.4 g of Pd 2 (dba ) 3 and 1.6 ml of (t-Bu) 3 P, and then stirred under reflux. The reaction was confirmed by thin layer chromatography. After adding water, the reaction was terminated. The organic layer was extracted with dichloromethane (MC) and filtered under reduced pressure, followed by column purification and recrystallization, to obtain 7.73 g (recovery rate of 74%) of OP1.

利用如上述OP1的方法，改變起始物質，從而合成了以下OP2至OP7。 合成例1：化合物1的合成 Using the method of OP1 described above, the starting materials were changed, and the following OP2 to OP7 were synthesized. Synthesis Example 1: Synthesis of Compound 1

在圓底燒瓶中，在100ml的甲苯中溶解5.0g的IM1、3.3g的OP1、1.5g的t-BuONa、0.4g的Pd2 (dba)3 及0.5ml的(t-Bu)3 P之後，進行回流攪拌。藉由薄層層析法來確認反應，添加水之後，結束反應。用二氯甲烷（MC）提取有機層，並進行減壓過濾之後，進行管柱純化及再結晶，從而獲得了5.01g（回收率為70%）的化合物1。In a round bottom flask, after dissolving 5.0 g of IM1, 3.3 g of OP1, 1.5 g of t-BuONa, 0.4 g of Pd 2 (dba) 3 and 0.5 ml of (t-Bu) 3 P in 100 ml of toluene, And stirred at reflux. The reaction was confirmed by thin layer chromatography. After adding water, the reaction was terminated. The organic layer was extracted with dichloromethane (MC) and filtered under reduced pressure, followed by column purification and recrystallization to obtain 5.01 g (recovery rate of 70%) of Compound 1.

m/z：677.31（100.0%），678.31（57.1%），679.31（15.7%），680.32（2.9%）m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

合成例2：化合物2的合成 Synthesis Example 2: Synthesis of Compound 2

利用IM2來代替IM1，從而藉由如合成例1的方法來合成了化合物2（回收率為74%）。IM2 was used instead of IM1, and compound 2 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 74%).

m/z：677.31（100.0%），678.31（57.1%），679.31（15.7%），680.32（2.9%）m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

合成例3：化合物3的合成 Synthesis Example 3: Synthesis of Compound 3

利用IM3來代替IM1，從而藉由如合成例1的方法來合成了化合物3（回收率為70%）。IM3 was used instead of IM1, and compound 3 was synthesized by the method as in Synthesis Example 1 (recovery rate was 70%).

m/z：677.31（100.0%），678.31（57.1%），679.31（15.7%），680.32（2.9%）m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

合成例4：化合物4的合成 Synthesis Example 4: Synthesis of Compound 4

利用IM4來代替IM1，從而藉由如合成例1的方法來合成了化合物4（回收率為65%）。IM4 was used instead of IM1, and compound 4 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 65%).

m/z：677.31（100.0%），678.31（57.1%），679.31（15.7%），680.32（2.9%）m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

合成例5：化合物5的合成 Synthesis Example 5: Synthesis of Compound 5

利用OP2來代替OP1，從而藉由如合成例1的方法來合成了化合物5（回收率為71%）。OP2 was used instead of OP1, and compound 5 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 71%).

m/z：727.32（100.0%），728.33（61.0%），729.33（18.3%），730.33（3.6%）m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

合成例6：化合物6的合成 Synthesis Example 6: Synthesis of Compound 6

利用OP3來代替OP1，從而藉由如合成例1的方法來合成了化合物6（回收率為75%）。OP3 was used instead of OP1, and compound 6 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 75%).

m/z：727.32（100.0%），728.33（61.0%），729.33（18.3%），730.33（3.6%）m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

合成例7：化合物7的合成 Synthesis Example 7: Synthesis of Compound 7

利用OP4來代替OP1，從而藉由如合成例1的方法來合成了化合物7（回收率為70%）。OP4 was used instead of OP1, and compound 7 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 70%).

m/z：637.28（100.0%），638.28（53.4%），639.28（14.0%），640.29（2.4%）m / z: 637.28 (100.0%), 638.28 (53.4%), 639.28 (14.0%), 640.29 (2.4%)

合成例8：化合物8的合成 Synthesis Example 8: Synthesis of Compound 8

利用OP5來代替OP1，從而藉由如合成例1的方法來合成了化合物8（回收率為62%）。OP5 was used instead of OP1, and compound 8 was synthesized by the method as in Synthesis Example 1 (recovery rate: 62%).

m/z：687.29（100.0%），688.30（57.7%），689.30（16.4%），690.30（3.0%）m / z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30 (3.0%)

合成例9：化合物9的合成 Synthesis Example 9: Synthesis of Compound 9

利用OP6來代替OP1，從而藉由如合成例1的方法來合成了化合物9（回收率為65%）。OP6 was used instead of OP1, and compound 9 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 65%).

m/z：687.29（100.0%），688.30（57.7%），689.30（16.4%），690.30（3.0%）m / z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30 (3.0%)

合成例10：化合物10的合成 Synthesis Example 10: Synthesis of Compound 10

利用OP7來代替OP1，從而藉由如合成例1的方法來合成了化合物10（回收率為70%）。OP7 was used instead of OP1, and compound 10 was synthesized by the method as in Synthesis Example 1 (the recovery rate was 70%).

m/z：713.31（100.0%），714.31（60.3%），715.31（17.6%），716.32（3.4%）m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

合成例11：化合物11的合成 Synthesis Example 11: Synthesis of Compound 11

利用OP8來代替OP1，從而藉由如合成例1的方法來合成了化合物11（回收率為72%）。OP8 was used instead of OP1, and compound 11 was synthesized by the method as in Synthesis Example 1 (recovery rate was 72%).

m/z：801.34（100.0%），802.34（67.4%），803.35（22.5%），804.35（4.9%）m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

製備例2：有機發光裝置的製備Preparation Example 2: Preparation of an organic light emitting device

對藉由蒸餾水超聲波以1500Å的厚度將氧化銦錫（ITO）塗敷成薄膜的玻璃基板進行洗滌。若蒸餾水洗滌結束，則利用異丙醇、丙酮、甲醇等的溶劑來進行超聲波洗滌，並進行乾燥之後，移送至電漿清洗機，然後利用氧電漿來將上述基板清洗5分鐘之後，在氧化銦錫基板上部利用熱蒸鍍機（thermal evaporator），作為電洞注入層將600Å的HI01進行制膜，將50Å的HATCN進行制膜，作為電洞傳輸層將600Å的化合物1進行制膜之後，作為上述發光層摻雜3%的BH01：BD01，以250Å進行制膜。接著，作為電子傳輸層將300Å的ET01：Liq（1：1）進行制膜之後，將10Å的LiF、1000Å的鋁（Al）進行制膜，並將該裝置密封（Encapsulation）於手套箱中，從而製備了有機發光裝置（實施例1）。A glass substrate coated with indium tin oxide (ITO) as a thin film by ultrasonication of distilled water at a thickness of 1500 Å was washed. After the washing with distilled water is completed, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and after drying, it is transferred to a plasma cleaner, and then the substrate is cleaned with an oxygen plasma for 5 minutes, and then oxidized. The upper part of the indium tin substrate was formed with a film of 600Å of HI01 as a hole injection layer, a film of 50Å of HATCN using a thermal evaporator, and a film of 600 作为 of compound 1 as a hole transport layer. The light-emitting layer was doped with BH01: BD01 at 3% and formed into a film at 250 Å. Next, after forming 300 层 of ET01: Liq (1: 1) as an electron transport layer, 10 F of LiF and 1000 Å of aluminum (Al) were formed into a film, and the device was sealed in a glove box. Thus, an organic light emitting device was prepared (Example 1).

藉由如上所述的方式使用化合物2至化合物11來代替化合物1，從而製備了有機發光裝置（實施例2至實施例11）。By using the compounds 2 to 11 instead of the compound 1 as described above, an organic light emitting device was prepared (Examples 2 to 11).

比較例Comparative example

使用以下Ref.1至Ref.8（比較例1至比較例8）來代替化合物1，除此之外，與上述製備例2相同地製備了有機發光裝置。 The following Ref.1 to Ref.8 (Comparative Example 1 to Comparative Example 8) were used in place of Compound 1, and an organic light-emitting device was prepared in the same manner as in Preparation Example 2 described above.

實驗例1：有機發光裝置的性能評價Experimental example 1: Performance evaluation of an organic light emitting device

利用吉時利2400源測量單元（Kiethley 2400 source measurement unit）施加電壓來注入電子及電洞，利用柯尼卡美能達（Konica Minolta）分光輻射計（CS-2000）來測定發光時的亮度，由此在大氣壓條件下，測定對於施加電壓的電流密度及亮度，從而評價了實施例及比較例的有機發光裝置的性能，並將其結果示於表1中。The electrons and holes were injected using a voltage applied by the Kiethley 2400 source measurement unit, and the Konica Minolta spectroradiometer (CS-2000) was used to measure the brightness at the time of light emission. The performance of the organic light-emitting devices of Examples and Comparative Examples was evaluated by measuring the current density and brightness with respect to the applied voltage under atmospheric pressure conditions. Table 1 shows the results.

表1 Table 1

如上述表1所示，可見在本發明的多個實施例中，與比較例1至比較例11相比，呈現了提高效率及延長壽命的結果。若比較本發明的實施例，則可知如下：1）與比較例5相比，具有二苯基芴成分的情況，2）與比較例1、比較例2相比，藉由取代二苯基芴部苯基來擴張共軛的情況，3）與比較例3、比較例4相比，藉由取代苯基來維持容易阻隔電子的最低未佔有分子軌道的情況，4）與比較例6、比較例7、比較例8相比，在芳胺的一側為苯基或萘基且另一側為非苯基的本發明的化合物中，有機發光裝置的驅動電壓低，並大大改善效率及壽命。As shown in Table 1 above, it can be seen that, in the various embodiments of the present invention, compared with Comparative Examples 1 to 11, the results of improving the efficiency and extending the life are exhibited. If the examples of the present invention are compared, it can be known as follows: 1) when compared with Comparative Example 5, having a diphenylphosphonium component, 2) compared with Comparative Examples 1 and 2, by replacing diphenylphosphonium In the case of expanding the conjugate with a partial phenyl group, 3) Compared with Comparative Examples 3 and 4, the case where the lowest unoccupied molecular orbital that easily blocks electrons is maintained by replacing the phenyl group, 4) Compared with Comparative Example 6, Compared with Example 7 and Comparative Example 8, in the compound of the present invention in which one side of the aromatic amine is phenyl or naphthyl and the other side is non-phenyl, the driving voltage of the organic light-emitting device is low, and the efficiency and life are greatly improved. .

上述本發明的說明是用於例示性的，本發明所屬技術領域具有通常知識者可以理解在不變更本發明的技術思想或必要特徵的情況下，能夠以其他具體方式容易變形。因此，應理解以上描述的多個實施例在所有方面是例示性的，而不是限定性的。例如，以單一型說明的各個結構要素可分散地實施，同樣，說明為分散的多個結構要素也能夠以結合的方式實施。The above description of the present invention is for illustration, and those having ordinary knowledge in the technical field to which the present invention pertains can understand that it can be easily modified in other specific ways without changing the technical idea or necessary features of the present invention. Therefore, it should be understood that the various embodiments described above are illustrative in all aspects and not restrictive. For example, each structural element described as a single type may be implemented in a decentralized manner, and similarly, a plurality of structural elements described as dispersed may be implemented in a combined manner.

本發明的範圍由所附的發明申請專利範圍表示，而不是上述詳細說明，發明申請專利範圍的含義及範圍以及由其等同概念匯出的所有變更或變形的方式應當被解釋為包括在本發明的範圍中。The scope of the present invention is indicated by the scope of the appended patent application for invention, rather than the above-mentioned detailed description. The meaning and scope of the scope of patent application for invention and all changes or modifications derived from its equivalent concept should be interpreted as being included in the present invention In the range.

100‧‧‧基板100‧‧‧ substrate

1000‧‧‧電洞注入電極1000‧‧‧ hole injection electrode

200‧‧‧電洞注入層200‧‧‧ Hole injection layer

2000‧‧‧電子注入電極2000‧‧‧ Electron injection electrode

300‧‧‧電洞傳輸層300‧‧‧ Hole Transmission Layer

400‧‧‧發光層400‧‧‧Light-emitting layer

500‧‧‧電子傳輸層500‧‧‧ electron transmission layer

600‧‧‧電子注入層600‧‧‧ electron injection layer

第1圖表示本發明一實例的有機發光裝置的簡圖。FIG. 1 is a schematic diagram showing an organic light emitting device according to an example of the present invention.

Claims (13)

一種化合物，係由以下化學式1表示， 化學式1其中， R1 為氫、重氫、C1 -C6 烷基或C6 -C30 的芳基； Ar1 至Ar4 分別獨立地為取代或未取代的C6 -C30 芳基、取代或未取代的C6 -C30 縮合芳基或取代或未取代的C5 -C30 雜芳基，且Ar3 及Ar4 能夠相互形成或不形成環； L為連接基團，其是選自單鍵、C6 -C30 伸芳基或C5 -C30 伸雜芳基； Ar為取代或未取代的C6 -C10 芳基、取代或未取代的C10 -C25 縮合芳基或取代或未取代的C5 -C30 雜芳基； l為1至4的整數，m為1至3的整數。A compound represented by the following Chemical Formula 1, Wherein R 1 is hydrogen, deuterium, C 1 -C 6 alkyl or C 6 -C 30 aryl; Ar 1 to Ar 4 are each independently substituted or unsubstituted C 6 -C 30 aryl, substituted Or unsubstituted C 6 -C 30 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl, and Ar 3 and Ar 4 can form or not form a ring with each other; L is a linking group, which is an optional group From a single bond, C 6 -C 30 aryl or C 5 -C 30 heteroaryl; Ar is substituted or unsubstituted C 6 -C 10 aryl, substituted or unsubstituted C 10 -C 25 condensed aryl Or a substituted or unsubstituted C 5 -C 30 heteroaryl group; l is an integer from 1 to 4, and m is an integer from 1 to 3. 如申請專利範圍第1項所述的化合物，其包含由以下化學式2或化學式3表示的化合物， 化學式2 化學式3其中， Ar、Ar1 、Ar2 、Ar4 、L、l及m如在申請專利範圍第1項中所定義， R2 至R5 分別獨立地為氫、重氫、C1 -C6 烷基、C6 -C30 芳基或C5 -C30 雜芳基。The compound according to item 1 of the scope of patent application, which includes a compound represented by the following Chemical Formula 2 or Chemical Formula 3, Chemical formula 3 Among them, Ar, Ar 1 , Ar 2 , Ar 4 , L, l, and m are as defined in the first patent application range, and R 2 to R 5 are each independently hydrogen, deuterium, or C 1 -C 6 alkane. , C 6 -C 30 aryl or C 5 -C 30 heteroaryl. 如申請專利範圍第1項所述的化合物，其包含由以下化學式4或化學式5表示的化合物， 化學式4化學式5其中， Ar、R1 、l及m如申請專利範圍第1項中所定義， R6 及R7 分別獨立地為氫、重氫或C1 -C6 烷基； R8 至R11 分別獨立地為氫、重氫、C1 -C6 烷基、C6 -C30 芳基或C5 -C30 雜芳基； Ar5 為取代或未取代的C6 -C30 芳基、取代或未取代的C6 -C30 縮合芳基或取代或未取代的C5 -C30 雜芳基； n為0至3的整數。The compound according to item 1 of the scope of patent application, which includes a compound represented by the following Chemical Formula 4 or Chemical Formula 5, Chemical formula 5 Among them, Ar, R 1 , l and m are as defined in the first patent application range, R 6 and R 7 are each independently hydrogen, deuterium or C 1 -C 6 alkyl; R 8 to R 11 are each independent Ground is hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 5 -C 30 heteroaryl; Ar 5 is substituted or unsubstituted C 6 -C 30 aryl, substituted or Unsubstituted C 6 -C 30 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl; n is an integer from 0 to 3. 如申請專利範圍第1項所述的化合物，其包含由化學式6或化學式7表示的化合物， 化學式6化學式7其中， Ar、R1 、l及m如在申請專利範圍第1項中所定義， R6 及R7 分別獨立地為氫、重氫或C1 -C6 烷基， R8 至R11 分別獨立地為氫、重氫、C1 -C6 烷基、C6 -C30 芳基或C5 -C30 雜芳基； Ar5 為取代或未取代的C6 -C30 芳基、取代或未取代的C6 -C30 縮合芳基或取代或未取代的C5 -C30 雜芳基。The compound according to item 1 of the scope of patent application, which includes a compound represented by Chemical Formula 6 or Chemical Formula 6, Chemical formula 7 Among them, Ar, R 1 , l and m are as defined in the first patent application scope, R 6 and R 7 are each independently hydrogen, deuterium or C 1 -C 6 alkyl, and R 8 to R 11 are respectively Is independently hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 5 -C 30 heteroaryl; Ar 5 is substituted or unsubstituted C 6 -C 30 aryl, substituted Or unsubstituted C 6 -C 30 condensed aryl or substituted or unsubstituted C 5 -C 30 heteroaryl. 如申請專利範圍第1項至第4項中任一項所述的化合物，其中Ar為未取代的C6 -C10 芳基或未取代的C10 -C25 縮合芳基。The compound as described in any one of claims 1 to 4, wherein Ar is an unsubstituted C 6 -C 10 aryl group or an unsubstituted C 10 -C 25 condensed aryl group. 如申請專利範圍第5項所述的化合物，其中Ar為苯基或萘基。The compound according to item 5 of the application, wherein Ar is phenyl or naphthyl. 如申請專利範圍第1項至第4項中任一項所述的化合物，其中l為1，R1 為氫。The compound according to any one of claims 1 to 4, wherein l is 1, and R 1 is hydrogen. 如申請專利範圍第2項所述的化合物，其中R3 及R4 分別獨立地為氫、甲基或苯基。The compound according to item 2 of the scope of patent application, wherein R 3 and R 4 are each independently hydrogen, methyl or phenyl. 如申請專利範圍第3項或第4項所述的化合物，其中R9 及R10 分別獨立地為氫、甲基或苯基。The compound as described in claim 3 or 4, wherein R 9 and R 10 are each independently hydrogen, methyl, or phenyl. 如申請專利範圍第1項所述的化合物，其為以下化合物中的一種： The compound according to item 1 of the scope of patent application, which is one of the following compounds: 如申請專利範圍第1 項所述的化合物，其為以下化合物中的一種： The compound as described in item 1 of the patent application scope, which is one of the following compounds: 一種有機發光裝置，其中在第一電極及第二電極之間包括含有如申請專利範圍第1項所述的化合物的一層以上的有機層。An organic light-emitting device, which includes one or more organic layers between the first electrode and the second electrode containing the compound described in item 1 of the scope of patent application. 如申請專利範圍第12項所述的有機發光裝置，其中該有機層為電洞注入層、電洞傳輸層及發光輔助層中的一層以上。The organic light-emitting device according to item 12 of the scope of patent application, wherein the organic layer is more than one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.
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