TW202104162A - Organic compound for capping layer and organic electroluminescent device including the same - Google Patents

Organic compound for capping layer and organic electroluminescent device including the same Download PDF

Info

Publication number
TW202104162A
TW202104162A TW109116961A TW109116961A TW202104162A TW 202104162 A TW202104162 A TW 202104162A TW 109116961 A TW109116961 A TW 109116961A TW 109116961 A TW109116961 A TW 109116961A TW 202104162 A TW202104162 A TW 202104162A
Authority
TW
Taiwan
Prior art keywords
chemical formula
substituted
unsubstituted
compound
group
Prior art date
Application number
TW109116961A
Other languages
Chinese (zh)
Inventor
咸昊完
安賢哲
金東駿
李東炫
韓政佑
李螢振
安慈恩
權桐熱
金兌旼
Original Assignee
南韓商東進世美肯股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 南韓商東進世美肯股份有限公司 filed Critical 南韓商東進世美肯股份有限公司
Publication of TW202104162A publication Critical patent/TW202104162A/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

The present invention relates to a compound for a cover layer and an organic light emitting device containing the same. One embodiment of the compound for a cover layer of the present invention is suitable for an organic light emitting device, and the compound can improve external luminous efficiency, color coordinates and service life of the organic light emitting device.

Description

覆蓋層用有機化合物及包含其的有機發光裝置Organic compound for covering layer and organic light emitting device containing the same

本發明係有關於覆蓋層用有機化合物及包含其的有機發光裝置。The present invention relates to an organic compound for a cover layer and an organic light-emitting device containing the organic compound.

在有機發光裝置中，用作有機物層的材料可根據功能大致分類為發光材料、電洞注入材料、電洞輸送材料、電子輸送材料、電子注入材料等。並且，上述發光材料可根據發光機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重態激發狀態的磷光材料。進而，可根據發光色分類為藍色、綠色、紅色發光材料。In organic light-emitting devices, materials used as the organic layer can be roughly classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like according to their functions. In addition, the above-mentioned light-emitting materials can be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to the light-emitting mechanism. Furthermore, it can be classified into blue, green, and red light-emitting materials according to the light-emitting color.

一般的有機發光裝置可具有如下結構，在基板上部形成陽極，在該陽極上部依次形成電洞輸送層、發光層、電子輸送層及陰極。其中，上述電洞輸送層、發光層及電子輸送層為由有機化合物形成的有機薄膜。A general organic light-emitting device may have a structure in which an anode is formed on the upper part of a substrate, and a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially formed on the upper part of the anode. Among them, the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films formed of organic compounds.

具有如上所述的結構的有機發光裝置的驅動原理如下。若向上述陽極及陰極之間施加電壓，則從陽極注入的電洞經由電洞輸送層而移動至發光層的同時從陰極注入的電子經由電子輸送層而移動至發光層。移動至發光層的上述電洞及電子再結合而生成激子（exciton）。上述激子從激發狀態轉換為基態而生成光。The driving principle of the organic light emitting device having the structure as described above is as follows. When a voltage is applied between the anode and the cathode, the holes injected from the anode move to the light emitting layer via the hole transport layer, and the electrons injected from the cathode move to the light emitting layer via the electron transport layer. The above-mentioned holes and electrons that have moved to the light-emitting layer recombine to generate excitons. The above-mentioned excitons convert from an excited state to a ground state to generate light.

有機發光裝置的效率通常可分為內部發光效率和外部發光效率。上述內部發光效率與如電洞輸送層、發光層及電子輸送層等一樣介入第一電極與第二電極之間的有機層中如何有效地生成激子而實現光轉換相關，按理論上來講，就內部發光效率而言，螢光為約25%，磷光為約100%。The efficiency of organic light-emitting devices can generally be divided into internal luminous efficiency and external luminous efficiency. The above-mentioned internal luminous efficiency is related to how to effectively generate excitons in the organic layer between the first electrode and the second electrode, such as the hole transport layer, the light emitting layer, and the electron transport layer, to achieve light conversion. In theory, In terms of internal luminous efficiency, fluorescence is about 25%, and phosphorescence is about 100%.

另一方面，外部發光效率呈現從上述有機物層生成的光提取到有機發光裝置外部的效率，通常，內部發光效率的約20％的水準提取到外部。On the other hand, the external luminous efficiency represents the efficiency of extracting the light generated from the organic material layer to the outside of the organic light-emitting device, and generally, about 20% of the internal luminous efficiency is extracted to the outside.

用於提高這種外部發光效率，即光提取效率的方法，為了防止發射到外部的光進行全反射而被損失，將多種有機化合物適用為覆蓋層（capping layer），為了改善有機發光裝置的性能，持續努力開發具有可提高外部發光效率的高折射率及薄膜穩定性的有機化合物。The method for improving the external luminous efficiency, that is, the light extraction efficiency, in order to prevent the light emitted to the outside from being totally reflected and lost, a variety of organic compounds are applied as a capping layer, in order to improve the performance of the organic light-emitting device Continuing efforts to develop organic compounds with high refractive index and film stability that can improve external luminous efficiency.

習知技術文獻 專利文獻 韓國公開專利公報第10-2004-0098238號Known technical literature Patent literature Korean Patent Publication No. 10-2004-0098238

發明要解決的技術問題The technical problem to be solved by the invention

本發明要解決的問題在於，提供維持高折射率的同時放大紫外線區域的吸收強度及範圍，增大外部量子效率，並可改善因暴露於外部紫外線而引起的壽命縮短問題的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。The problem to be solved by the present invention is to provide a compound for a coating layer and a coating layer that amplifies the absorption intensity and range of the ultraviolet region while maintaining a high refractive index, increases the external quantum efficiency, and can improve the problem of shortened lifetime caused by exposure to external ultraviolet rays. An organic light-emitting device including a cover layer containing the above-mentioned compound.

本發明要解決的問題在於，提供使可見光區域吸收最小化，維持寬的帶隙，可實現高色純度的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。The problem to be solved by the present invention is to provide a compound for a cover layer that minimizes absorption in the visible light region, maintains a wide band gap, and can achieve high color purity, and an organic light-emitting device including a cover layer containing the compound.

本發明要解決的另一問題在於，提供使化合物內龐大特性最小化，改善分子間薄膜排列，由此改善折射率，並可從外部空氣及水分中改善穩定性的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。Another problem to be solved by the present invention is to provide a coating compound that minimizes bulk properties in the compound, improves the arrangement of the intermolecular film, thereby improves the refractive index, and improves the stability from the external air and moisture, and includes The organic light-emitting device of the covering layer of the above-mentioned compound.

本發明要解決的另一問題在於，提供具有高的Tg及高的Td，以防止分子間再結晶化，從而可從有機發光裝置驅動時產生的熱中維持穩定的薄膜的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。Another problem to be solved by the present invention is to provide a compound for a coating layer that has a high Tg and a high Td to prevent intermolecular recrystallization, thereby maintaining a stable thin film from the heat generated when the organic light-emitting device is driven. An organic light-emitting device containing a coating layer of the above-mentioned compound.

但是，本發明要解決的問題不局限於以上描述的問題，所屬技術領域具有通常知識者應當藉由以下的記載內容明確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 should clearly understand other problems not described by the following description.

本發明的技術方案在於：The technical scheme of the present invention is:

本發明的第一實施方式提供由以下化學式1表示的覆蓋層用化合物。The first embodiment of the present invention provides a compound for a cover layer represented by the following Chemical Formula 1.

化學式1

Figure 02_image001
在上述化學式1中， A、B及C各自獨立地為取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基，上述A、B及C中的一個以上為以下化學式1-1， L1 至L3 各自獨立地為直接鍵合、取代或未取代的C6~C50的伸芳基、或者取代或未取代的C2~C50的雜芳基， 化學式1-1
Figure 02_image004
在上述化學式1-1中， X各自獨立地為CR或N， R各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。Chemical formula 1
Figure 02_image001
In the above chemical formula 1, A, B and C are each independently a substituted or unsubstituted C6-C50 aryl group, or a C2-C50 heteroaryl group formed by a substituted or unsubstituted C2-C9 ring structure, One or more of the above-mentioned A, B, and C is the following chemical formula 1-1, each of L 1 to L 3 is independently a directly bonded, substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2 ~C50 heteroaryl, chemical formula 1-1
Figure 02_image004
In the above chemical formula 1-1, X is each independently CR or N, and R is each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted Substituted C2~C30 alkenyl, substituted or unsubstituted C1~C30 alkoxy, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted by Or a C2-C50 heteroaryl group formed by an unsubstituted C2-C9 ring structure.

本發明的第二實施方式提供有機發光裝置，其包括：第一電極及第二電極；有機物層，介於上述第一電極及上述第二電極內側；以及覆蓋層，配置於上述第一電極及上述第二電極中的一個以上電極外側，並包含本發明第一實施方式的覆蓋層用化合物。The second embodiment of the present invention provides an organic light-emitting device, which includes: a first electrode and a second electrode; an organic layer interposed between the first electrode and the second electrode; and a cover layer disposed on the first electrode and the second electrode. One or more of the above-mentioned second electrodes are outside and contain the compound for a cover layer according to the first embodiment of the present invention.

對照先前技術之功效Compare the effects of previous technologies

本發明的一實例的覆蓋層用化合物呈現如下作用效果，維持高折射率的同時放大紫外線區域的吸收強度及範圍，增大外部量子效率，並可改善因暴露於外部紫外線而引起的壽命縮短問題。The compound for the coating layer of an example of the present invention exhibits the following effects, while maintaining a high refractive index, amplifying the absorption intensity and range of the ultraviolet region, increasing the external quantum efficiency, and improving the problem of shortened life due to exposure to external ultraviolet rays .

並且，本發明的一實例的覆蓋層用化合物呈現如下作用效果，使可見光區域吸收最小化，維持寬的帶隙，可實現高色純度。In addition, the compound for a cover layer of an example of the present invention exhibits the following effects to minimize absorption in the visible light region, maintain a wide band gap, and achieve high color purity.

進而，本發明的一實例的覆蓋層用化合物呈現如下作用效果，使化合物內龐大特性最小化，改善分子間薄膜排列，由此改善折射率，並可從外部空氣及水分中改善穩定性。Furthermore, the compound for a coating layer of an example of the present invention exhibits the following effects, minimizing bulk properties in the compound, improving the arrangement of the intermolecular film, thereby improving the refractive index, and improving the stability from external air and moisture.

進而，本發明一實例的覆蓋層用化合物呈現具有高的Tg及高的Td，以防止分子間再結晶化，從而可從有機發光裝置驅動時產生的熱中維持穩定的薄膜的作用效果。Furthermore, the compound for a cover layer of an example of the present invention exhibits a high Tg and a high Td to prevent intermolecular recrystallization, thereby maintaining a stable film effect from the heat generated when the organic light-emitting device is driven.

以下，參照圖式，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 with ordinary knowledge in the technical field to which the present invention belongs can be easily implemented.

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，標注了類似的元件符號。However, the present invention can be implemented in many different forms, and is not limited to the examples and embodiments described here. In addition, in the drawings, in order to clearly explain the present invention, parts that are not related to the description are omitted. In the entire 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 specification 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 there are other components 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”。In the entire specification of the present invention, when a part "includes" a structural element, unless there is a special description to the contrary, it means that other structural elements may be included instead of excluding other structural elements. The terms "about", "substantially", etc. used throughout the specification of the present invention are used in the meaning of their value or close to their value when the mentioned meanings indicate inherent preparation and material tolerances to prevent ambiguity. The infringer improperly uses the disclosure that mentions accurate or absolute values in order to help understand the present invention. The term "~ (of) step" or "~ step" used throughout the specification of the present invention does not mean "a 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“它們的組合”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群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群組中的一種以上。Throughout the specification of the present invention, the term "their combination" contained in the expression of the Markush form means to be 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 of the above means to include more than one selected from the group consisting of the above-mentioned multiple 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”。In the entire specification of the present invention, the description of "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”或“伸芳基”可意味著包含C6-50 的芳香族烴環基，例如，苯基、苄基、萘基、聯苯基、三聯苯基、芴基、菲基、三苯基烯基、苯基烯基、䓛基、熒蒽基、苯並芴基、苯並三苯基烯基、苯並䓛基、蒽基、均二苯乙烯基、芘基等的芳香族環，“雜芳基”或“伸雜芳基”作為包含一個以上雜原子的C2-50 的芳香族環，例如，意味著包含從吡咯啉基、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、苯並噻吩基、二苯並噻吩基、喹啉基、異喹啉基、喹㗁啉基、哢唑基、菲基唳基、吖啶基、菲基咯啉基、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雜環基。Throughout the specification of the present invention, the term "aryl" or "arylene" may mean a C 6-50 aromatic hydrocarbon ring group, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl Group, fluorenyl group, phenanthryl group, triphenylalkenyl group, phenylalkenyl group, triphenylalkenyl group, fluoranthene group, benzofluorenyl group, benzotriphenylalkenyl group, benzotriphenylalkenyl group, anthracenyl group, stilbene Aromatic rings such as vinyl, pyrenyl, etc., "heteroaryl" or "heteroaryl" as a C 2-50 aromatic ring containing one or more heteroatoms, for example, means containing from pyrrolinyl, pyrrolidinyl, Azinyl, pyridyl, indolyl, isoindolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, quinolinyl, Isoquinolinyl, quinolinyl, oxazolyl, phenanthryl, acridinyl, phenanthroline, thienyl and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring , Indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, pyrazine ring, oxazole ring, furan ring, thiophene ring, oxazole ring, oxadiene ring A heterocyclic group formed by an azole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, and a dibenzofuran ring.

在本發明說明書全文中，術語“取代的”或“可取代的”可意味著可由選自由重氫、鹵素、氨基、腈基、硝基或C1 ～ 30 的烷基、C2 ～ 30 的烯基、C1 ～ 30 的烷氧基、C3 ～ 20 的環烷基、C3 ～ 20 的雜環烷基、C1 ～ 30 硫醚基、C6 ～ 30 的芳基及C2 ～ 30 的雜芳基組成的群組中的一種以上的基取代未取代。並且，在本發明說明書全文中，相同的元件符號只要沒有特別提及的內容，就可具有相同意思。In the specification of the present invention, the term "substituted" or "substituted" means that may be selected from the group consisting of heavy hydrogen, halogen, amino, nitrile, nitro or C 1 ~ 30 alkyl group, C 2 ~ 30 of alkenyl group, C 1 ~ 30 alkoxy group, C 3 ~ 20 cycloalkyl group, the heterocycloalkyl group of C 3 ~ 20, C 1-30 thioether, C aryl and C 6 ~ 30 ~ 2 One or more groups in the group consisting of 30 heteroaryl groups are substituted and unsubstituted. In addition, in the entire specification of the present invention, the same reference signs may have the same meaning as long as there is no special mention.

本發明的第一實施方式提供由以下化學式1表示的覆蓋層用化合物。The first embodiment of the present invention provides a compound for a cover layer represented by the following Chemical Formula 1.

化學式1

Figure 02_image001
在上述化學式1中， A、B及C各自獨立地為取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基，上述A、B及C中的一個以上為以下化學式1-1， L1 至L3 各自獨立地為直接鍵合、取代或未取代的C6~C50的伸芳基、或者取代或未取代的C2~C50的雜芳基。 化學式1-1
Figure 02_image004
在上述化學式1-1中， X各自獨立地為CR或N， R各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。Chemical formula 1
Figure 02_image001
In the above chemical formula 1, A, B and C are each independently a substituted or unsubstituted C6-C50 aryl group, or a C2-C50 heteroaryl group formed by a substituted or unsubstituted C2-C9 ring structure, One or more of the above-mentioned A, B, and C is the following chemical formula 1-1, each of L 1 to L 3 is independently a directly bonded, substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2 ~C50 heteroaryl. Chemical formula 1-1
Figure 02_image004
In the above chemical formula 1-1, X is each independently CR or N, and R is each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted Substituted C2~C30 alkenyl, substituted or unsubstituted C1~C30 alkoxy, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted by Or a C2-C50 heteroaryl group formed by an unsubstituted C2-C9 ring structure.

在本發明中，上述取代基各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。In the present invention, the above-mentioned substituents are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C2~C30 alkenyl, substituted Or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted or unsubstituted C2~C9 ring structure The formed C2~C50 heteroaryl group.

並且，在本發明中，上述雜芳基的C2~C9的環結構可包含吡啶或喹啉，而不包含哢唑、二苯並呋喃及二苯並噻吩。如上所述，雜芳基由C2~C9形成，使龐大特性最小化，改善分子間薄膜排列，由此改善有機發光裝置的折射率時非常有效。Furthermore, in the present invention, the C2-C9 ring structure of the heteroaryl group may include pyridine or quinoline, but not azole, dibenzofuran, and dibenzothiophene. As described above, the heteroaryl group is formed from C2 to C9, which minimizes bulkiness and improves the arrangement of the intermolecular film, thereby improving the refractive index of the organic light-emitting device.

本發明的一實例的上述化學式1的覆蓋層用化合物，藉由由二環的稠芳基或稠雜芳基取代的芳基胺，維持高折射率的同時可增大紫外線區域的吸收波長強度及範圍。藉由這種特性，本發明的覆蓋層用化合物增大有機發光裝置的外部量子效率，可從外部紫外線暴露中改善壽命。The compound for the coating layer of the above chemical formula 1 of an example of the present invention can increase the absorption wavelength intensity in the ultraviolet region while maintaining a high refractive index by using an arylamine substituted with a bicyclic fused aryl group or a fused heteroaryl group And scope. With this characteristic, the compound for a cover layer of the present invention increases the external quantum efficiency of the organic light-emitting device, and can improve the lifetime from external ultraviolet exposure.

並且，本發明的一實例的上述化學式1的覆蓋層用化合物包含二環的稠芳基或稠雜芳基，由此使可見光區域的吸收最小化，可維持寬的帶隙，其結果可實現高色純度。In addition, the compound for coating layer of the above chemical formula 1 of an example of the present invention contains a bicyclic fused aryl group or fused heteroaryl group, thereby minimizing the absorption in the visible light region and maintaining a wide band gap. As a result, it can be realized High color purity.

並且，本發明的一實例的上述化學式1的覆蓋層用化合物，線性連接使龐大特性最小化的二環的稠芳基或稠雜芳基，由此分子間薄膜排列變得優秀。由此，可改善折射率，並可從外部空氣或水分中改善穩定性。其中，上述線性連接意味著L1至L3包含伸苯基的情況下，較佳地結合在1,4-伸苯基的位置。In addition, the compound for the coating layer of the above-mentioned chemical formula 1 of an example of the present invention linearly connects a bicyclic fused aryl group or a fused heteroaryl group that minimizes bulkiness, so that the intermolecular film arrangement becomes excellent. As a result, the refractive index can be improved, and the stability can be improved from outside air or moisture. Wherein, the above-mentioned linear connection means that when L1 to L3 contain phenylene, they are preferably bonded at the position of 1,4-phenylene.

並且，本發明的一實例的上述化學式1的覆蓋層用化合物，在450nm的折射率可以為2.1以上，具體地可以為2.2以上。並且，在紫外線吸收區域380nm下的吸收強度為0.6以上，具體地可以為0.7以上。In addition, the compound for a coating layer of Chemical Formula 1 in an example of the present invention may have a refractive index at 450 nm of 2.1 or more, specifically 2.2 or more. In addition, the absorption intensity at 380 nm in the ultraviolet absorption region is 0.6 or more, and specifically may be 0.7 or more.

並且，本發明的一實例的上述化學式1的覆蓋層用化合物包含二環的稠芳基或稠雜芳基，具有高的Tg及Td，其結果可防止分子間再結晶化，由此可從驅動有機發光裝置時產生的熱中維持穩定的薄膜。In addition, the compound for the coating layer of the above-mentioned chemical formula 1 of an example of the present invention contains a bicyclic fused aryl group or a fused heteroaryl group, and has high Tg and Td. As a result, intermolecular recrystallization can be prevented, thereby being able to prevent intermolecular recrystallization. A stable thin film is maintained in the heat generated when the organic light-emitting device is driven.

即，將本發明的一實例的覆蓋層用化合物適用於覆蓋層，若將上述覆蓋層配置於有機發光裝置的電極外側，則可提高外部發光效率。當從介於有機發光裝置的第一電極及第二電極內側的有機物層中生成的光提取到有機發光裝置的外部時，可防止向外部發射的光被全反射而損失。That is, the compound for a cover layer of an example of the present invention is applied to the cover layer, and if the cover layer is arranged outside the electrode of the organic light-emitting device, the external luminous efficiency can be improved. When the light generated from the organic material layer inside the first electrode and the second electrode of the organic light emitting device is extracted to the outside of the organic light emitting device, the light emitted to the outside can be prevented from being totally reflected and lost.

本發明的一實例的覆蓋層用化合物，因如上的結構特徵，可具有高折射率，薄膜穩定性突出，當適用為有機發光裝置的覆蓋層時，可提高有機發光裝置的外部發光效率、色座標及壽命。The compound for a cover layer of an example of the present invention can have a high refractive index and outstanding film stability due to the above structural characteristics. When applied as a cover layer of an organic light-emitting device, it can improve the external luminous efficiency and color of the organic light-emitting device. Coordinates and life.

在本發明的一實例中，上述化學式1可由以下化學式2表示。In an example of the present invention, the above Chemical Formula 1 may be represented by the following Chemical Formula 2.

化學式2

Figure 02_image008
在上述化學式2中， A、B及C各自獨立地如上述化學式1中所定義， l、m及n各自獨立地為0或1至4的整數， l+m+n為1以上的整數。Chemical formula 2
Figure 02_image008
In the above chemical formula 2, A, B, and C are each independently as defined in the above chemical formula 1, l, m, and n are each independently 0 or an integer of 1 to 4, and l+m+n is an integer of 1 or more.

由上述化學式2表示的化合物，包含與胺的氮直接鍵合的伸苯基，維持不能吸收可見光區域的寬的帶隙，並有效改善折射率。The compound represented by the above-mentioned chemical formula 2 contains phenylene directly bonded to the nitrogen of the amine, maintains a wide band gap in the region that cannot absorb visible light, and effectively improves the refractive index.

在本發明的一實例中，上述化學式1的化合物可由以下化學式3至化學式5中的一個表示。In an example of the present invention, the compound of the above Chemical Formula 1 may be represented by one of the following Chemical Formula 3 to Chemical Formula 5.

化學式3

Figure 02_image010
Chemical formula 3
Figure 02_image010

化學式4

Figure 02_image012
Chemical formula 4
Figure 02_image012

化學式5

Figure 02_image014
在上述化學式3至化學式5中， A、B及C各自獨立地如上述化學式1中所定義， o及p各自獨立地為0、1或2， q為2至7的整數， r為0或1至4的整數。Chemical formula 5
Figure 02_image014
In the above chemical formulas 3 to 5, A, B and C are each independently as defined in the above chemical formula 1, o and p are each independently 0, 1, or 2, q is an integer from 2 to 7, and r is 0 or An integer from 1 to 4.

如上所述，由上述化學式3至化學式5表示的化合物包含1,4-伸苯基，增大紫外線區域的吸收波長強度及範圍的同時可具有高折射率。As described above, the compounds represented by the above Chemical Formula 3 to Chemical Formula 5 include 1,4-phenylene, and can have a high refractive index while increasing the intensity and range of the absorption wavelength in the ultraviolet region.

根據本發明的一實例，A、B及C中的2個以上可以為以下化學式1-1。這種情況下，還能以低的分子量實現高的Tg。According to an example of the present invention, two or more of A, B, and C may be the following chemical formula 1-1. In this case, a high Tg can also be achieved with a low molecular weight.

化學式1-1

Figure 02_image004
在上述化學式1-1中， X各自獨立地為CR或N， R各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。Chemical formula 1-1
Figure 02_image004
In the above chemical formula 1-1, X is each independently CR or N, and R is each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted Substituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted by Or a C2-C50 heteroaryl formed by an unsubstituted C2-C9 ring structure.

根據本發明的一實例，A、B及C均可以為上述化學式1-1。這種情況下，還能以低的分子量實現高的Tg。According to an example of the present invention, A, B and C can all be the above chemical formula 1-1. In this case, a high Tg can also be achieved with a low molecular weight.

並且，根據本發明的一實例，在上述化學式1-1中，X均可以為CR，具體地，R均可以為氫。當X均為CR時，可維持更寬的帶隙。Moreover, according to an example of the present invention, in the above chemical formula 1-1, X can all be CR, and specifically, R can be hydrogen. When X is CR, a wider band gap can be maintained.

並且，根據本發明的一實例，上述A可以為取代或未取代的萘基。當A為萘基時，可實現更高的折射率。Moreover, according to an example of the present invention, the aforementioned A may be a substituted or unsubstituted naphthyl group. When A is a naphthyl group, a higher refractive index can be achieved.

在本發明的一實例中，上述化學式1的化合物可以由以下化學式6至化學式9中的一個表示。In an example of the present invention, the compound of the above Chemical Formula 1 may be represented by one of the following Chemical Formula 6 to Chemical Formula 9.

化學式6

Figure 02_image016
Chemical formula 6
Figure 02_image016

化學式7

Figure 02_image018
Chemical formula 7
Figure 02_image018

化學式8

Figure 02_image020
Chemical formula 8
Figure 02_image020

化學式9

Figure 02_image022
在上述化學式6至化學式9中， A、B及C各自獨立地如上述化學式1中所定義， o為0、1或2， q為2至6的整數， r為0或1至4的整數， R1 及R2 各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。Chemical formula 9
Figure 02_image022
In the above chemical formulas 6 to 9, A, B and C are each independently as defined in the above chemical formula 1, o is 0, 1, or 2, q is an integer from 2 to 6, and r is an integer from 0 or 1 to 4. , R 1 and R 2 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C2~C30 alkenyl, substituted or unsubstituted Substituted C1~C30 alkoxy, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted or unsubstituted C2~C9 ring structure formed C2~C50 heteroaryl groups.

如上所述，由上述化學式6至化學式9表示的化合物，還能以較小的分子量具有高的Tg的同時可具有高折射率。As described above, the compounds represented by the above Chemical Formula 6 to Chemical Formula 9 can also have a high Tg with a smaller molecular weight and a high refractive index.

根據本發明的一實例，A、B及C可各自獨立地選自由苯基、聯苯基、三聯苯基、萘基、吡啶基、喹啉基或它們的組合組成的群組中。According to an example of the present invention, A, B, and C may each independently be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, pyridyl, quinolinyl, or a combination thereof.

並且，根據本發明的一實例，上述化學式1的化合物可包含一個以上的甲基、甲氧基、氟基或氰基作為取代基。Also, according to an example of the present invention, the compound of the above Chemical Formula 1 may include more than one methyl group, methoxy group, fluoro group or cyano group as a substituent.

在本發明的一實例中，由上述化學式1至化學式9表示的覆蓋層用化合物能夠以如下所述的反應式進行合成，不局限於此，還能夠以多種方法進行合成。In an example of the present invention, the compound for the coating layer represented by the above Chemical Formula 1 to Chemical Formula 9 can be synthesized in the following reaction formula, but is not limited to this, and can also be synthesized in a variety of methods.

反應式

Figure 02_image024
Reaction formula
Figure 02_image024

在本發明的一實例中，由上述化學式1表示的化合物可以為以下提出的化合物1至化合物312中的一種化合物，可不局限於此：

Figure 02_image026
Figure 02_image028
Figure 02_image030
Figure 02_image032
Figure 02_image034
Figure 02_image036
Figure 02_image038
Figure 02_image040
Figure 02_image042
Figure 02_image044
Figure 02_image046
Figure 02_image048
Figure 02_image050
Figure 02_image052
Figure 02_image054
Figure 02_image056
Figure 02_image058
Figure 02_image060
Figure 02_image062
Figure 02_image064
Figure 02_image066
Figure 02_image068
Figure 02_image070
Figure 02_image072
Figure 02_image074
Figure 02_image076
。In an example of the present invention, the compound represented by the above chemical formula 1 may be one of the compounds 1 to 312 proposed below, but may not be limited thereto:
Figure 02_image026
Figure 02_image028
Figure 02_image030
Figure 02_image032
Figure 02_image034
Figure 02_image036
Figure 02_image038
Figure 02_image040
Figure 02_image042
Figure 02_image044
Figure 02_image046
Figure 02_image048
Figure 02_image050
Figure 02_image052
Figure 02_image054
Figure 02_image056
Figure 02_image058
Figure 02_image060
Figure 02_image062
Figure 02_image064
Figure 02_image066
Figure 02_image068
Figure 02_image070
Figure 02_image072
Figure 02_image074
Figure 02_image076
.

本發明的第二實施方式提供包括含有由上述化學式1至化學式9中的一種表示的化合物的覆蓋層的有機發光裝置。The second embodiment of the present invention provides an organic light-emitting device including a cover layer containing a compound represented by one of the above-mentioned Chemical Formula 1 to Chemical Formula 9.

根據本發明的一實例，有機發光裝置可包括：第一電極及第二電極，有機物層，介於上述第一電極及上述第二電極內側；以及覆蓋層，配置於上述第一電極及上述第二電極中的一個以上的電極外側，並包含本發明的覆蓋層用化合物。其中，在第一電極或第二電極的兩側面中，將與介於第一電極與第二電極之間的有機物層相鄰的一側作為內側，將不與有機物層相鄰的一側作為外側。即，在第一電極的外側配置覆蓋層時，在覆蓋層與有機物層之間介入第一電極，在第二電極的外側配置覆蓋層時，在覆蓋層與有機物層之間介入第二電極。According to an example of the present invention, an organic light-emitting device may include: a first electrode and a second electrode, an organic layer interposed between the first electrode and the second electrode; and a cover layer disposed on the first electrode and the second electrode. The outer side of one or more of the two electrodes contains the compound for a coating layer of the present invention. Among them, of the two sides of the first electrode or the second electrode, the side adjacent to the organic layer between the first electrode and the second electrode is taken as the inner side, and the side not adjacent to the organic layer is taken as the inner side. Outside. That is, when the covering layer is arranged outside the first electrode, the first electrode is interposed between the covering layer and the organic layer, and when the covering layer is arranged outside the second electrode, the second electrode is interposed between the covering layer and the organic layer.

根據本發明的一實例，就上述有機發光裝置而言，在第一電極及第二電極內側可介入多種有機物層，在第一及第二電極中的至少一個外側可形成覆蓋層。上述覆蓋層均形成在第一電極的外側和第二電極外側，或者可配置於第一電極的外側或第二電極的外側。上述覆蓋層可包含本發明的覆蓋層用化合物。According to an example of the present invention, for the above-mentioned organic light-emitting device, a variety of organic layers can be inserted inside the first electrode and the second electrode, and a covering layer can be formed outside at least one of the first and second electrodes. The above-mentioned covering layers are both formed on the outside of the first electrode and the outside of the second electrode, or may be arranged on the outside of the first electrode or the outside of the second electrode. The above-mentioned cover layer may contain the compound for a cover layer of the present invention.

並且，根據本發明的一實例，在介入有上述覆蓋層的第一電極及第二電極外側上還可形成起到多種功能的有機物層。即，覆蓋層可直接形成於第一電極（或第二電極）外側表面上，或者在第一電極（或第二電極）外側表面形成起到多種功能的有機物層，並在上述有機物層上可形成包含本發明的化合物的覆蓋層。In addition, according to an example of the present invention, an organic layer with multiple functions may be formed on the outer side of the first electrode and the second electrode interposed with the above-mentioned covering layer. That is, the covering layer may be directly formed on the outer surface of the first electrode (or second electrode), or an organic layer with multiple functions may be formed on the outer surface of the first electrode (or second electrode), and the organic layer may be formed on the organic layer. A covering layer containing the compound of the present invention is formed.

根據本發明的一實例，覆蓋層可單獨包含本發明的一實例的覆蓋層用化合物，或者可一起包含2種以上或習知的化合物。According to an example of the present invention, the cover layer may separately include the compound for the cover layer of an example of the present invention, or may include two or more or conventional compounds together.

本發明的一實例的有機發光裝置在第一電極及第二電極之間，即在第一電極及第二電極的內側包括1層以上的有機物層，在上述第一電極及第二電極的外側可形成覆蓋層。上述有機物層通常可以是構成發光部的電洞輸送層、發光層及電子輸送層，可不局限於此。The organic light-emitting device of an example of the present invention includes one or more organic layers between the first electrode and the second electrode, that is, on the inner side of the first electrode and the second electrode, and on the outer side of the first electrode and the second electrode. A cover layer can be formed. The above-mentioned organic substance layer may generally be a hole transport layer, a light emitting layer, and an electron transport layer constituting the light emitting part, but is not limited to these.

上述有機發光裝置在第一電極（陽極，anode）與第二電極（陰極，cathode）之間可包括1層以上的電洞注入層（HIL）、電洞輸送層（HTL）、發光層（EML）、電子輸送層（ETL）、電子注入層（EIL）等構成發光部的有機物層。The above organic light-emitting device may include more than one hole injection layer (HIL), hole transport layer (HTL), and light emitting layer (EML) between the first electrode (anode) and the second electrode (cathode). ), electron transport layer (ETL), electron injection layer (EIL) and other organic material layers that constitute the light-emitting part.

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。有機發光裝置可至下而上依次層疊第一電極（陽極，電洞注入電極1000）/電洞注入層200/電洞輸送層300/發光層400/電子輸送層500/電子注入層600/第二電極（陰極，電子注入電極2000）/覆蓋層3000。For example, the above-mentioned organic light-emitting device can be manufactured according to the structure described in Fig. 1. The organic light-emitting device can stack the first electrode (anode, hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/light emitting layer 400/electron transport layer 500/electron injection layer 600/section from bottom to top. Two electrodes (cathode, electron injection electrode 2000)/covering layer 3000.

如上所述，本發明的一實例的覆蓋層用化合物，藉由由二環的稠芳基或稠雜芳基取代的芳基胺，維持高折射率的同時增大紫外線區域的吸收波長強度及範圍，來增大有機發光裝置的外部量子效率，並可從外部紫外線暴露中改善壽命，由於包含二環的稠芳基或稠雜芳基，因此可使可見光區域的吸收最小化並可維持寬的帶隙，其結果可實現高色純度，線性連接（例如，結合在1,4-伸苯基的位置）使龐大特性最小化的二環的稠芳基或稠雜芳基，分子間薄膜排列優秀，由此可改善折射率，可從外部空氣或水分中改善穩定性。並且，根據本發明的一實例的上述化學式1的覆蓋層用化合物包含二環的稠芳基或稠雜芳基，具有高的Tg及Td，其結果可防止分子間再結晶化，由此可從驅動有機發光裝置時產生的熱中維持穩定的薄膜。即，將本發明的一實例的覆蓋層用化合物適用於覆蓋層，若將上述覆蓋層配置於有機發光裝置的電極外側，則可提高外部發光效率。當從介於有機發光裝置的第一電極及第二電極內側的有機物層中生成的光提取到有機發光裝置外部時，可防止向外部發射的光被全反射而損失。As described above, the compound for a coating layer of an example of the present invention uses an arylamine substituted with a bicyclic fused aryl group or a fused heteroaryl group to maintain a high refractive index while increasing the absorption wavelength intensity in the ultraviolet region and Range to increase the external quantum efficiency of the organic light-emitting device and improve the lifetime from external ultraviolet exposure. Since the bicyclic fused aryl group or fused heteroaryl group is included, the absorption of the visible light region can be minimized and the wide range can be maintained. As a result, high color purity can be achieved, linear connection (for example, combined at the position of 1,4-phenylene) to minimize the bulkiness of the bicyclic fused aryl or fused heteroaryl, intermolecular thin film Excellent arrangement, which can improve refractive index, and improve stability from outside air or moisture. In addition, the compound for the coating layer of the above-mentioned chemical formula 1 according to an example of the present invention contains a bicyclic fused aryl group or a fused heteroaryl group, and has high Tg and Td. As a result, intermolecular recrystallization can be prevented, thereby Maintain a stable thin film from the heat generated when the organic light-emitting device is driven. That is, the compound for a cover layer of an example of the present invention is applied to the cover layer, and if the cover layer is arranged outside the electrode of the organic light-emitting device, the external luminous efficiency can be improved. When the light generated from the organic layer inside the first electrode and the second electrode of the organic light emitting device is extracted to the outside of the organic light emitting device, the light emitted to the outside can be prevented from being totally reflected and lost.

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 Figure 1, the substrate 100 can be a substrate for an organic light-emitting device. In particular, it can be a transparent glass substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Curved plastic substrate.

第一電極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 first electrode 1000 serves as an anode for injecting holes of the organic light-emitting device. In order to be able to inject holes, a material with a low work function is used, which can be formed of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

藉由真空沉積法、旋塗法、鑄造法、LB（Langmuir-Blodgett）法等來在上述第一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10-3torr（托）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。並且，在電洞注入層表面，根據需要可追加沉積電荷發生層。作為電荷發生層物質可使用常規的物質，可舉例HATCN。The hole injection layer material is deposited on the upper portion of the first electrode by a vacuum deposition method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, or the like, thereby forming the hole injection layer 200. In the case of forming the hole injection layer by the above-mentioned vacuum deposition method, 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 hole injection layer required, etc., but generally It can be appropriately selected within a deposition temperature of 50-500°C, a vacuum degree of 10-8 to 10-3torr (torr), a deposition speed of 0.01 to 100 Å/sec, and a layer thickness of 10 Å to 5 μm. In addition, a charge generation layer can be additionally deposited on the surface of the hole injection layer as needed. As the charge generation layer material, conventional materials can be used, and HATCN can be exemplified.

接著，藉由真空沉積法、旋塗法、鑄造法、LB法等來在上述電洞注入層200上部沉積電洞輸送層物質，由此可形成電洞輸送層300。在藉由上述真空沉積法來形成電洞輸送層的情況下，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。Next, the 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, thereby forming the hole transport layer 300. In the case of forming the hole transport layer 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 range of almost the same conditions as the formation of the hole injection layer .

上述電洞輸送層300可使用習知的化合物而形成。根據本發明的一實例，電洞輸送層300可以是1層以上，雖然圖中未示出，但在上述電洞輸送層300上可形成發光輔助層。The hole transport layer 300 can be formed using a known compound. According to an example of the present invention, the hole transport layer 300 may be more than one layer. Although not shown in the figure, a light-emitting auxiliary layer may be formed on the hole transport layer 300 described above.

藉由真空沉積法、旋塗法、鑄造法、LB法等方法，在上述電洞輸送層300或發光輔助層上沉積發光層物質，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習知的化合物用作主體或摻雜劑。The light-emitting layer material is deposited on the hole transport layer 300 or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, or an LB method, thereby forming the light-emitting layer 400. In the case of forming the light-emitting layer by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select within a range of almost the same conditions as the formation of the hole injection layer. In addition, the above-mentioned light-emitting layer material may use a conventional compound as a host or dopant.

並且，在發光層中，與磷光摻雜劑一同使用的情況下，為了防止三重態激子或電洞向電子輸送層擴散的現象，藉由真空沉積法或旋塗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習知的物質中選擇任意物質來利用。例如，可例舉噁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（如通用顯示器（UDC）公司的BCP（Basso Coupoline））等。In addition, when used together with phosphorescent dopants in the light-emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, a vacuum deposition method or a spin coating method can also be laminated to suppress the holes Material (HBL). The hole suppressing substance that can be used at this time is not particularly limited, but any substance can be selected and used from conventional substances used as hole suppressing materials. For example, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, or the hole suppressing material described in JP 11-329734 (A1) can be exemplified. Representatively, Balq (double (8-hydroxy-2-methylquinoline)-aluminum biphenolate), phenanthrolines (phenanthrolines) compounds (such as BCP (Basso Coupoline) of Universal Display (UDC)), etc.

在如上形成的發光層400上部形成有電子輸送層500，此時，上述電子輸送層可藉由真空沉積法、旋塗法、鑄造法等方法來形成。並且，上述電子輸送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 above. In this case, the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. In addition, the deposition conditions of the above-mentioned electron transport layer differ depending on the compound used, but in general, it is preferable to select within a range of almost the same conditions as the formation of the hole injection layer.

之後，可在上述電子輸送層500上部沉積電子注入層物質來形成電子注入層600，此時，上述電子輸送層可藉由真空沉積法、旋塗法、鑄造法等的方法來形成常規的電子注入層物質。After that, the electron injection layer material can be deposited on the electron transport layer 500 to form the electron injection layer 600. At this time, the electron transport layer can be formed by vacuum deposition, spin coating, casting and other methods to form conventional electrons. Inject layer material.

上述有機發光裝置的電洞注入層200、電洞輸送層300、發光層400、電子輸送層500可使用如下的物質，不局限於此。

Figure 02_image078
Figure 02_image080
Figure 02_image082
Figure 02_image084
Figure 02_image086
Figure 02_image088
Figure 02_image090
The following substances can be used for the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the above-mentioned organic light emitting device, and are not limited thereto.
Figure 02_image078
Figure 02_image080
Figure 02_image082
Figure 02_image084
Figure 02_image086
Figure 02_image088
Figure 02_image090

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第二電極2000。作為第二電極，可使用多種金屬。具體例有鋁、金、銀、鎂等的物質。The second electrode 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 second electrode, various metals can be used. Specific examples include substances such as aluminum, gold, silver, and magnesium.

本發明的有機發光裝置不僅可以採用第一電極、電洞注入層、電洞輸送層、發光層、電子輸送層、電子注入層、第二電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 organic light-emitting devices with a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode structure, but also organic light-emitting devices with a variety of structures. For the structure of the light-emitting device, one or two intermediate layers can also be formed as required.

如上所述，根據本發明形成的各個有機物層的厚度可根據所需的程度來進行調節，具體為10至1000nm，更具體地可以為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, specifically 10 to 1000 nm, more specifically 20 to 150 nm.

根據本發明的一實例，在上述第一電極1000中，在使電洞注入層200介入的電極的外側可形成覆蓋層3000。並且，在上述第二電極2000中，在使電子注入層600介入的電極外側可形成覆蓋層3000，但不局限於此，上述覆蓋層3000可藉由沉積工序形成，上述覆蓋層3000的厚度可以為100至1000Å，更具體地可以為300至1000Å。此時，可防止覆蓋層的透射率降低。According to an example of the present invention, in the above-mentioned first electrode 1000, a cover layer 3000 may be formed on the outer side of the electrode where the hole injection layer 200 is inserted. In addition, in the second electrode 2000, the covering layer 3000 may be formed on the outside of the electrode where the electron injection layer 600 is inserted, but it is not limited to this. The covering layer 3000 may be formed by a deposition process, and the thickness of the covering layer 3000 may be It is 100 to 1000 Å, more specifically 300 to 1000 Å. At this time, the transmittance of the cover layer can be prevented from decreasing.

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，但可不局限於此。Regarding the organic light-emitting compound of this embodiment, the content described in the first embodiment of the present invention can be applied, but it is not limited to this.

以下，藉由本發明的實施例進行更具體的說明，本發明的範圍不局限於本實施例。Hereinafter, an embodiment of the present invention will be used for more specific description, and the scope of the present invention is not limited to this embodiment.

中間體的合成Synthesis of intermediates

為了合成目的化合物，合成中間體（IM，Intermediate）。In order to synthesize the target compound, an intermediate (IM, Intermediate) is synthesized.

製備例1：IM1的合成Preparation Example 1: Synthesis of IM1

以下IM1的合成法如下。

Figure 02_image092
The synthesis method of the following IM1 is as follows.
Figure 02_image092

在圓底燒瓶中，將（4-（萘-1-基）苯基）硼酸30.0g、1-溴-4-碘苯26.3g溶解於600ml的1,4-二噁烷中，並放入160ml的K2 CO3 （2M）和3.7g的Pd（PPh3 ）4 之後，進行回流攪拌。利用薄層層析法（TLC）來確認反應，並添加水之後，結束反應。利用甲基纖維素（MC）來提取有機層，並進行減壓過濾之後進行柱純化，由此得到中間體IM1 24.0g（收率63％）。In a round bottom flask, 30.0 g of (4-(naphthalene-1-yl)phenyl)boronic acid and 26.3 g of 1-bromo-4-iodobenzene were dissolved in 600 ml of 1,4-dioxane and put in After 160 ml of K 2 CO 3 (2M) and 3.7 g of Pd (PPh 3 ) 4 , reflux and stirring were performed. The reaction was confirmed by thin layer chromatography (TLC), and after adding water, the reaction was terminated. The organic layer was extracted with methyl cellulose (MC), filtered under reduced pressure, and then subjected to column purification, thereby obtaining 24.0 g of intermediate IM1 (yield 63%).

製備例2：IM2的合成Preparation Example 2: Synthesis of IM2

以與上述IM1相同的方法，如下列表1所示，改變起始物質來合成如下的IM2。

Figure 02_image094
In the same way as the above IM1, as shown in Table 1 below, change the starting materials to synthesize the following IM2.
Figure 02_image094

表1 IM2的起始物質

Figure 02_image096
，
Figure 02_image098
（4-（萘-2-基）苯基）硼酸（4-naphthalene-2-yl）phenyl）boronic acid， 1-溴-4-碘苯（1-bromo-4-iodobenzene） Table 1 IM2 starting material
Figure 02_image096
,
Figure 02_image098
 (4-(Naphthalene-2-yl)phenyl)boronic acid, 1-bromo-4-iodobenzene (1-bromo-4-iodobenzene)

覆蓋層用化合物的合成Synthesis of compound for covering layer

合成例1：化合物20的合成

Figure 02_image100
Synthesis Example 1: Synthesis of Compound 20
Figure 02_image100

在圓底燒瓶中，將IM1 3.0g、二（[1,1':4',1''-三聯苯]-4-基）胺（di（[1,1':4',1''-terphenyl]-4-yl）amine））4.4g、t-BuONa 1.2g、Pd2 （dba）3 0.3g、（t-Bu）3 P 0.4ml溶解於120ml的甲苯，進行回流攪拌。利用薄層層析法來確認反應，並添加水之後，結束反應。利用甲基纖維素來提取有機層，並進行減壓過濾之後進行再結晶，由此得到化合物20 3.7g（收率59％）。In a round bottom flask, mix IM1 3.0g, two ([1,1':4',1''-terphenyl]-4-yl)amine (di([1,1':4',1'' -terphenyl]-4-yl)amine)) 4.4 g, t-BuONa 1.2 g, Pd 2 (dba) 3 0.3 g, and (t-Bu) 3 P 0.4 ml were dissolved in 120 ml of toluene and stirred under reflux. The reaction was confirmed by thin layer chromatography, and after adding water, the reaction was terminated. The organic layer was extracted with methyl cellulose, filtered under reduced pressure, and then recrystallized to obtain 3.7 g of compound 20 (yield 59%).

m/z：751.32（100.0%）、752.33（63.2%）、753.33（19.6%）、754.33（4.0%）m/z: 751.32 (100.0%), 752.33 (63.2%), 753.33 (19.6%), 754.33 (4.0%)

玻璃轉化溫度（Tg；TA儀器（TA instruments），DSC-2500）：130℃Glass transition temperature (Tg; TA instruments, DSC-2500): 130°C

合成例2：化合物222的合成

Figure 02_image102
Synthesis Example 2: Synthesis of Compound 222
Figure 02_image102

以與合成例1相同的方法，使用IM2及雙（4-（萘-2-基）苯基）胺（bi（4-（naphthalene-2-yl）phenyl）amine）來代替IM1及二（[1,1':4',1''三聯苯-]-4-基）胺，合成化合物222（收率65％）。In the same way as Synthesis Example 1, IM2 and bis(4-(naphthalene-2-yl)phenyl)amine (bi(4-(naphthalene-2-yl)phenyl)amine) were used instead of IM1 and two([ 1,1':4',1'' terphenyl-]-4-yl)amine, compound 222 was synthesized (yield 65%).

m/z：699.29（100.0%）、700.30（58.8%）、701.30（17.0%）、702.30（3.2%）m/z: 699.29 (100.0%), 700.30 (58.8%), 701.30 (17.0%), 702.30 (3.2%)

玻璃轉化溫度（Tg；TA instruments, DSC-2500）：113℃Glass transition temperature (Tg; TA instruments, DSC-2500): 113℃

合成例3：化合物163的合成

Figure 02_image104
Synthesis Example 3: Synthesis of Compound 163
Figure 02_image104

在圓底燒瓶中，將IM2 3.0g、[1,1'-聯苯]-4-胺（[1,1'-biphenyl]-4-amine）1.4g、t-BuONa 1.2g、Pd2 （dba）3 0.3g、（t-Bu）3 P 0.4ml溶解於150ml的甲苯之後，進行回流攪拌。利用薄層層析法來確認反應，並添加水之後，結束反應。利用甲基纖維素來提取有機層，並進行減壓過濾之後進行再結晶，由此得到化合物163 3.6g（收率60％）。In a round bottom flask, mix IM2 3.0g, [1,1'-biphenyl]-4-amine ([1,1'-biphenyl]-4-amine) 1.4g, t-BuONa 1.2g, Pd 2 ( dba) 3 0.3 g and (t-Bu) 3 P 0.4 ml were dissolved in 150 ml of toluene, and then refluxed and stirred. The reaction was confirmed by thin layer chromatography, and after adding water, the reaction was terminated. The organic layer was extracted with methyl cellulose, filtered under reduced pressure, and then recrystallized to obtain 3.6 g of compound 163 (yield 60%).

m/z：725.31（100.0%）、726.31（61.4%）、727.31（18.2%）、728.32（3.6%）m/z: 725.31 (100.0%), 726.31 (61.4%), 727.31 (18.2%), 728.32 (3.6%)

玻璃轉化溫度（Tg；TA instruments, DSC-2500）：120℃Glass transition temperature (Tg; TA instruments, DSC-2500): 120℃

合成例4：化合物68的合成

Figure 02_image106
Synthesis Example 4: Synthesis of Compound 68
Figure 02_image106

以與合成例1相同的方法，使用IM2來代替IM1，合成化合物68（收率60％）。In the same manner as in Synthesis Example 1, IM2 was used instead of IM1 to synthesize compound 68 (yield 60%).

m/z：751.32（100.0%）、752.33（63.2%）、753.33（19.6%）、754.33（4.0%）m/z: 751.32 (100.0%), 752.33 (63.2%), 753.33 (19.6%), 754.33 (4.0%)

玻璃轉化溫度（Tg；TA instruments, DSC-2500）：129℃Glass transition temperature (Tg; TA instruments, DSC-2500): 129℃

合成例5：化合物229的合成

Figure 02_image108
Synthesis Example 5: Synthesis of Compound 229
Figure 02_image108

以與合成例3相同的方法，使用4-（萘-2-基）苯胺（4-（naphthalene-2-yl）aniline）來代替[1,1'-聯苯]-4-胺，合成化合物229。（收率60%）In the same way as Synthesis Example 3, using 4-(naphthalene-2-yl)aniline (4-(naphthalene-2-yl)aniline) instead of [1,1'-biphenyl]-4-amine, the compound was synthesized 229. (Yield 60%)

m/z：775.32（100.0%）、776.33（65.4%）、777.33（21.0%）、778.33（4.4%）m/z: 775.32 (100.0%), 776.33 (65.4%), 777.33 (21.0%), 778.33 (4.4%)

玻璃轉化溫度（Tg；TA instruments, DSC-2500）：127℃Glass transition temperature (Tg; TA instruments, DSC-2500): 127℃

有機發光裝置的製備Preparation of organic light emitting device

根據第1圖中所記載的結構來製備有機發光裝置。有機發光裝置可至下而上依次層疊第一電極（電洞注入電極1000）/電洞注入層200/電洞輸送層300/發光層400/電子輸送層500/電子注入層600/第二電極（電子注入電極2000）/覆蓋層3000。According to the structure described in Figure 1, an organic light-emitting device was prepared. The organic light-emitting device can sequentially stack the first electrode (hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/light emitting layer 400/electron transport layer 500/electron injection layer 600/second electrode from bottom to top (Electron injection electrode 2000)/covering layer 3000.

在第1圖中，當製備有機發光裝置時，基板10可以為透明的玻璃基板或可彎曲的塑膠基板。In Figure 1, when the organic light-emitting device is prepared, the substrate 10 may be a transparent glass substrate or a flexible plastic substrate.

第一電極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（grapheme）之類的透明的材質形成。The first electrode 1000 serves as an anode for injecting holes of the organic light-emitting device. In order to be able to inject holes, a substance with a low work function is used, which can be formed of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and grapheme.

在電洞注入層200、電洞輸送層300、發光層400、電子輸送層500中，使用下列表2中所整理的多種物質。In the hole injection layer 200, the hole transport layer 300, the light-emitting layer 400, and the electron transport layer 500, a variety of substances sorted out in Table 2 below are used.

表2

Figure 02_image110
Figure 02_image112
Figure 02_image114
Figure 02_image116
Figure 02_image118
Figure 02_image120
Figure 02_image122
     Table 2
Figure 02_image110
Figure 02_image112
Figure 02_image114
Figure 02_image116
Figure 02_image118
Figure 02_image120
Figure 02_image122

在電子注入層600上形成用於注入電子的第二電極2000。作為第二電極，可使用多種金屬。具體例有鋁、金、銀等的物質。A second electrode 2000 for injecting electrons is formed on the electron injection layer 600. As the second electrode, various metals can be used. Specific examples include substances such as aluminum, gold, and silver.

實施例1：本發明的有機發光裝置的製備Example 1: Preparation of the organic light-emitting device of the present invention

在形成包含Ag的反射層的ITO基板上，作為電洞注入層將600Å的HI01進行製膜，將50Å的HATCN進行製膜，作為電洞輸送層將500Å的HT01進行製膜之後，作為上述發光層摻雜3％的BH01：BD01，以250Å進行製膜。接著，作為電子輸送層將300Å的ET01：Liq（1：1）進行製膜之後，沉積LiF 10Å，形成電子注入層。接著，以15nm的厚度沉積MgAg，在上述陰極上，作為覆蓋層，以600Å厚度沉積在合成例1中製備的化合物。將該裝置密封（Encapsulation）於手套箱中，從而製備有機發光裝置。On an ITO substrate on which a reflective layer containing Ag is formed, 600Å HI01 is formed as a hole injection layer, 50Å HATCN is formed as a film, and 500Å HT01 is formed as a hole transport layer. The layer is doped with 3% BH01: BD01, and the film is formed at 250 Å. Next, 300Å of ET01:Liq (1:1) was deposited as an electron transport layer, and LiF 10Å was deposited to form an electron injection layer. Next, MgAg was deposited in a thickness of 15 nm, and on the above-mentioned cathode, as a covering layer, the compound prepared in Synthesis Example 1 was deposited in a thickness of 600 Å. The device was sealed (Encapsulation) in a glove box to prepare an organic light-emitting device.

實施例2至5：本發明的有機發光裝置的製備Examples 2 to 5: Preparation of the organic light emitting device of the present invention

以與實施例1相同的方法進行製備，分別使用在合成例2至5中製備的化合物來代替合成例1中製備的化合物，製備將覆蓋層製膜的有機發光裝置。The preparation was performed in the same manner as in Example 1, and the compounds prepared in Synthesis Examples 2 to 5 were used instead of the compounds prepared in Synthesis Example 1, respectively, to prepare an organic light-emitting device in which a cover layer was formed.

比較例1至3：有機發光裝置的製備Comparative Examples 1 to 3: Preparation of Organic Light-Emitting Device

以與實施例1相同的方法進行製備，分別使用下列表3中所示的Ref.1至Ref.3來代替合成例1中製備的化合物，製備將覆蓋層製膜的有機發光裝置。The preparation was carried out in the same manner as in Example 1, and Ref. 1 to Ref. 3 shown in Table 3 below were used instead of the compound prepared in Synthesis Example 1 to prepare an organic light-emitting device in which a cover layer was formed.

表3

Figure 02_image124
玻璃轉化溫度（Tg）78℃
Figure 02_image126
玻璃轉化溫度（Tg）90℃
Figure 02_image128
玻璃轉化溫度（Tg）95℃ table 3
Figure 02_image124
Glass transition temperature (Tg) 78℃
Figure 02_image126
Glass transition temperature (Tg) 90℃
Figure 02_image128
Glass transition temperature (Tg) 95℃

實驗例1：有機發光裝置的性能評價Experimental example 1: Performance evaluation of 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，從而評價實施例1至實施例5及比較例1至比較例3的有機發光裝置的性能，並將其結果示於下列表4中。The Kiethley 2400 source measurement unit is used to apply voltage to inject electrons and holes, and the Konica Minolta spectroradiometer (CS-2000) is used to measure the brightness of light emission. Under atmospheric pressure conditions, the current density and brightness with respect to the applied voltage were measured to evaluate the performance of the organic light-emitting devices of Examples 1 to 5 and Comparative Examples 1 to 3, and the results are shown in Table 4 below .

表4   Op. V mA/cm2 Cd/A CIEx CIEy LT97 實施例1 3.50 10 7.30 0.139 0.048 155 實施例2 3.50 10 7.66 0.141 0.046 163 實施例3 3.50 10 7.64 0.140 0.046 162 實施例4 3.50 10 7.61 0.139 0.047 160 實施例5 3.50 10 7.72 0.140 0.045 170 比較例1 3.52 10 6.02 0.131 0.059 69 比較例2 3.59 10 4.50 0.130 0.073 46 比較例3 3.51 10 6.32 0.133 0.056 100 Table 4 Op. V mA/cm 2 Cd/A CIEx CIEy LT97 Example 1 3.50 10 7.30 0.139 0.048 155 Example 2 3.50 10 7.66 0.141 0.046 163 Example 3 3.50 10 7.64 0.140 0.046 162 Example 4 3.50 10 7.61 0.139 0.047 160 Example 5 3.50 10 7.72 0.140 0.045 170 Comparative example 1 3.52 10 6.02 0.131 0.059 69 Comparative example 2 3.59 10 4.50 0.130 0.073 46 Comparative example 3 3.51 10 6.32 0.133 0.056 100

本發明相比於比較例1，在胺的一側面具有1個以上的二環的稠芳基，由此具有高折射率，分子間薄膜排列變得優秀的同時增大紫外線區域的吸收波長，將110℃以上的高Tg，有效改善有機發光裝置的效率及壽命。Compared with Comparative Example 1, the present invention has one or more bicyclic fused aromatic groups on one side of the amine, thereby having a high refractive index, and the intermolecular film arrangement becomes excellent while increasing the absorption wavelength in the ultraviolet region. The high Tg above 110°C can effectively improve the efficiency and lifetime of the organic light-emitting device.

並且，本發明相比於比較例2，可維持使可見光區域的吸收的寬的帶隙，從CIEy座標結果中可確認可實現高色純度的有機發光裝置。In addition, compared with Comparative Example 2, the present invention can maintain a wider band gap for absorption in the visible light region, and it can be confirmed from the CIEy coordinate results that an organic light-emitting device with high color purity can be realized.

進而，本發明相比於比較例3，用一個胺使分子的龐大特性最小化，還能以小的分子量將折射率改善為2.2以上，由此可實現高效率及高色純度。Furthermore, compared with Comparative Example 3, the present invention minimizes the bulkiness of the molecule with a single amine, and can also improve the refractive index to 2.2 or more with a small molecular weight, thereby achieving high efficiency and high color purity.

實驗例2：折射率的評價Experimental example 2: Evaluation of refractive index

利用化合物20（合成例1）、化合物222（合成例2）及化合物163（合成例3）和表3的Ref.1化合物，在矽基板上借助真空沉積設備分別製備厚度為30nm的沉積膜，並利用橢偏儀裝置（J.A.Woollam Co. Inc, M-2000X）來測定450nm的折射率。其結果如下列表5中所整理。Using compound 20 (synthesis example 1), compound 222 (synthesis example 2), compound 163 (synthesis example 3) and the Ref. 1 compound in Table 3, a deposition film with a thickness of 30 nm was prepared on a silicon substrate with the aid of vacuum deposition equipment. And use an ellipsometer device (JAWoollam Co. Inc, M-2000X) to measure the refractive index of 450nm. The results are summarized in Table 5 below.

表5 @450nm Ref.1 化合物20 化合物222 化合物163 折射率，n 1.95 2.20 2.26 2.26 table 5 @450nm Ref.1 Compound 20 Compound 222 Compound 163 Refractive index, n 1.95 2.20 2.26 2.26

如上述表5中所記載，可確認化合物20、化合物222及化合物163在450nm下的折射率為2.1以上，更具體地，呈現2.2以上的高的折射率。As described in Table 5 above, it was confirmed that the refractive index of Compound 20, Compound 222, and Compound 163 at 450 nm was 2.1 or higher, and more specifically, exhibited a high refractive index of 2.2 or higher.

實驗例3：紫外線區域中的吸收強度的評價Experimental example 3: Evaluation of absorption intensity in the ultraviolet region

在紫外線區域中，利用化合物20（合成例1）、化合物222（合成例2）及化合物163（合成例3）和表3的Ref.1化合物來在矽基板上借助真空沉積設備分別製備厚度為30nm的沉積膜，並利用橢偏儀裝置（J.A.Woollam Co. Inc, M-2000X）來測定250nm～1000nm範圍內的吸收波長。其結果如第2圖中所示。可確認在紫外線吸收區域380nm的基準上，化合物20、化合物222及化合物163的吸收強度為0.6以上，具體為0.7以上，相比於Ref.1化合物，吸收強度上升30％以上，更具體地，上升50％以上。In the ultraviolet region, compound 20 (synthesis example 1), compound 222 (synthesis example 2) and compound 163 (synthesis example 3) and the Ref.1 compound in Table 3 were used to prepare the silicon substrate with a thickness of 30nm deposited film, and use ellipsometer device (JAWoollam Co. Inc, M-2000X) to measure the absorption wavelength in the range of 250nm~1000nm. The results are shown in Figure 2. It can be confirmed that the absorption intensity of compound 20, compound 222, and compound 163 is 0.6 or more, specifically 0.7 or more based on the ultraviolet absorption region of 380 nm, and the absorption intensity is increased by more than 30% compared to the Ref.1 compound. More specifically, Increased by more than 50%.

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實施方式是例示性的，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 illustrative purposes, and those with 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 essential features of the present invention. Therefore, it should be understood that the multiple embodiments described above are illustrative in all embodiments and not restrictive. For example, each structural element described in a single type can be implemented in a dispersed manner, and similarly, a plurality of structural elements described as being dispersed can also be implemented in a combined manner.

本發明的範圍由所附的申請專利範圍表示，而不是上述詳細說明，申請專利範圍的含義及範圍以及由其等同概念導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 attached patent application, rather than the above detailed description. The meaning and scope of the scope of the patent application and all changes or modifications derived from its equivalent concepts should be construed as being included in the scope of the present invention .

100:基板 200:電洞注入層 300:電洞輸送層 400:發光層 500:電子輸送層 600:電子注入層 1000:第一電極（陽極） 2000:第二電極（陰極） 3000:覆蓋層100: substrate 200: hole injection layer 300: Electric hole transport layer 400: luminescent layer 500: electron transport layer 600: electron injection layer 1000: The first electrode (anode) 2000: Second electrode (cathode) 3000: Overlay

第1圖表示本發明一實例的有機發光裝置的簡圖。 第2圖為比較在紫外線區域中本發明一實例的化合物和比較例化合物的吸收強度的曲線圖。Fig. 1 shows a schematic diagram of an organic light-emitting device according to an example of the present invention. Figure 2 is a graph comparing the absorption intensity of a compound of an example of the present invention and a compound of a comparative example in the ultraviolet region.

Figure 109116961-A0101-11-0002-1
Figure 109116961-A0101-11-0002-1

100:基板 100: substrate

200:電洞注入層 200: hole injection layer

300:電洞輸送層 300: Electric hole transport layer

400:發光層 400: luminescent layer

500:電子輸送層 500: electron transport layer

600:電子注入層 600: electron injection layer

1000:第一電極(陽極) 1000: first electrode (anode)

2000:第二電極(陰極) 2000: second electrode (cathode)

3000:覆蓋層 3000: Overlay

Claims (14)

一種覆蓋層用化合物，其由以下化學式1表示： 化學式1
Figure 03_image001
在該化學式1中， A、B及C各自獨立地為取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基，A、B及C中的一個以上為以下化學式1-1， L1 至L3 各自獨立地為直接鍵合、取代或未取代的C6~C50的伸芳基、或者取代或未取代的C2~C50的雜芳基， 化學式1-1
Figure 03_image004
在該化學式1-1中， X各自獨立地為CR或N， R各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。A compound for a covering layer, which is represented by the following chemical formula 1: Chemical formula 1
Figure 03_image001
In the chemical formula 1, A, B and C are each independently a substituted or unsubstituted C6-C50 aryl group, or a C2-C50 heteroaryl group formed by a substituted or unsubstituted C2-C9 ring structure, One or more of A, B, and C is the following chemical formula 1-1, and L 1 to L 3 are each independently a directly bonded, substituted or unsubstituted C6~C50 arylene group, or a substituted or unsubstituted C2~ C50 heteroaryl, chemical formula 1-1
Figure 03_image004
In the chemical formula 1-1, X is each independently CR or N, and R is each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted Substituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted by Or a C2-C50 heteroaryl formed by an unsubstituted C2-C9 ring structure. 根據請求項1所述的覆蓋層用化合物，其中，該化學式1由以下化學式2表示： 化學式2
Figure 03_image008
在該化學式2中， A、B及C各自獨立地如請求項1中所定義， l、m及n各自獨立地為0或1至4的整數，l+m+n為1以上的整數。The compound for a cover layer according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2: chemical formula 2
Figure 03_image008
In the chemical formula 2, A, B, and C are each independently as defined in claim 1, l, m, and n are each independently 0 or an integer from 1 to 4, and l+m+n is an integer of 1 or more. 根據請求項1所述的覆蓋層用化合物，其中該化學式1由以下化學式3至化學式5中的一個表示： 化學式3
Figure 03_image010
化學式4
Figure 03_image012
化學式5
Figure 03_image014
在該化學式3至該化學式5中， A、B及C各自獨立地如請求項1中所定義， o及p各自獨立地為0、1或2， q為2至7的整數， r為0或1至4的整數。The compound for a cover layer according to claim 1, wherein the chemical formula 1 is represented by one of the following chemical formulas 3 to 5: chemical formula 3
Figure 03_image010
Chemical formula 4
Figure 03_image012
Chemical formula 5
Figure 03_image014
In the chemical formula 3 to the chemical formula 5, A, B, and C are each independently as defined in claim 1, o and p are each independently 0, 1, or 2, q is an integer from 2 to 7, and r is 0 Or an integer from 1 to 4. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中，A、B及C中的2個以上為以下化學式1-1： 化學式1-1
Figure 03_image004
在該化學式1-1中， X各自獨立地為CR或N， R各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。The compound for a coating layer according to any one of claims 1 to 3, wherein two or more of A, B, and C are the following chemical formula 1-1: Chemical formula 1-1
Figure 03_image004
In the chemical formula 1-1, X is each independently CR or N, and R is each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted Substituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted by Or a C2-C50 heteroaryl group formed by an unsubstituted C2-C9 ring structure. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中，A、B及C均為該化學式1-1。The compound for a coating layer according to any one of claims 1 to 3, wherein A, B and C are all of the chemical formula 1-1. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中，X為CR。The compound for a coating layer according to any one of claims 1 to 3, wherein X is CR. 根據請求項6所述的覆蓋層用化合物，其中，R為H。The compound for a coating layer according to claim 6, wherein R is H. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中，A為取代或未取代的萘基。The compound for a coating layer according to any one of claims 1 to 3, wherein A is a substituted or unsubstituted naphthyl group. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中該化學式1的化合物由以下化學式6至化學式9中的一個表示： 化學式6
Figure 03_image016
化學式7
Figure 03_image018
化學式8
Figure 03_image020
化學式9
Figure 03_image022
在該化學式6至該化學式9中， A、B及C各自獨立地如請求項1中所定義， o為0、1或2， q為2至6的整數， r為0或1至4的整數， R1 及R2 各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。The compound for a cover layer according to any one of claims 1 to 3, wherein the compound of Chemical Formula 1 is represented by one of the following Chemical Formulas 6 to 9: Chemical Formula 6
Figure 03_image016
Chemical formula 7
Figure 03_image018
Chemical formula 8
Figure 03_image020
Chemical formula 9
Figure 03_image022
In the chemical formula 6 to the chemical formula 9, A, B and C are each independently as defined in claim 1, o is 0, 1 or 2, q is an integer from 2 to 6, and r is 0 or 1 to 4. Integer, R 1 and R 2 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C2~C30 alkenyl, substituted or Unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted or unsubstituted C2~C9 ring structure formed The C2~C50 heteroaryl group. 根據請求項1至3中任一項所述的覆蓋層用化合物，其中，A、B及C各自獨立地選自由苯基、聯苯基、三聯苯基、萘基、吡啶基、喹啉基或它們的組合組成的群組中。The compound for a coating layer according to any one of claims 1 to 3, wherein A, B, and C are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridyl group, and a quinolyl group Or a combination of them. 根據請求項1至3中任一項所述的覆蓋層用化合物，其包含一個以上的甲基、甲氧基、氟基或氰基作為取代基。The compound for a coating layer according to any one of claims 1 to 3, which contains one or more methyl groups, methoxy groups, fluoro groups, or cyano groups as substituents. 根據請求項1所述的覆蓋層用化合物，其中該化學式1為以下化合物中的一個：
Figure 03_image026
Figure 03_image028
Figure 03_image030
Figure 03_image032
Figure 03_image034
Figure 03_image036
Figure 03_image038
Figure 03_image040
Figure 03_image042
Figure 03_image044
Figure 03_image046
Figure 03_image048
Figure 03_image050
Figure 03_image052
Figure 03_image054
Figure 03_image056
Figure 03_image058
Figure 03_image060
Figure 03_image062
Figure 03_image064
Figure 03_image066
Figure 03_image068
Figure 03_image070
Figure 03_image072
Figure 03_image074
Figure 03_image076
。The compound for a covering layer according to claim 1, wherein the chemical formula 1 is one of the following compounds:
Figure 03_image026
Figure 03_image028
Figure 03_image030
Figure 03_image032
Figure 03_image034
Figure 03_image036
Figure 03_image038
Figure 03_image040
Figure 03_image042
Figure 03_image044
Figure 03_image046
Figure 03_image048
Figure 03_image050
Figure 03_image052
Figure 03_image054
Figure 03_image056
Figure 03_image058
Figure 03_image060
Figure 03_image062
Figure 03_image064
Figure 03_image066
Figure 03_image068
Figure 03_image070
Figure 03_image072
Figure 03_image074
Figure 03_image076
. 一種有機發光裝置，其包括： 一第一電極及一第二電極； 一有機物層，介於該第一電極及該第二電極的內側；以及 一覆蓋層，配置於該第一電極及該第二電極中的一個以上的電極的外側，並包含如請求項1至12中任一項所述的覆蓋層用化合物。An organic light emitting device, which includes: A first electrode and a second electrode; An organic layer between the inner side of the first electrode and the second electrode; and A covering layer is arranged on the outer side of one or more of the first electrode and the second electrode, and contains the covering layer compound according to any one of claims 1 to 12. 根據請求項13所述的有機發光裝置，其中該覆蓋層的厚度為300至1000Å。The organic light-emitting device according to claim 13, wherein the thickness of the cover layer is 300 to 1000 Å.
TW109116961A 2019-05-27 2020-05-21 Organic compound for capping layer and organic electroluminescent device including the same TW202104162A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020190061745A KR20200136115A (en) 2019-05-27 2019-05-27 Organic compound for capping layer and organic electroluminescent divice including the same
KR10-2019-0061745 2019-05-27

Publications (1)

Publication Number Publication Date
TW202104162A true TW202104162A (en) 2021-02-01

Family

ID=73466596

Family Applications (1)

Application Number Title Priority Date Filing Date
TW109116961A TW202104162A (en) 2019-05-27 2020-05-21 Organic compound for capping layer and organic electroluminescent device including the same

Country Status (3)

Country Link
KR (1) KR20200136115A (en)
CN (1) CN111995530A (en)
TW (1) TW202104162A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114206826A (en) 2020-03-31 2022-03-18 出光兴产株式会社 Compound, material for organic electroluminescent element, and electronic device
CN112952020A (en) * 2021-02-03 2021-06-11 烟台显华光电材料研究院有限公司 Organic electroluminescent device and display device comprising same
CN115710265A (en) * 2021-08-19 2023-02-24 江苏三月科技股份有限公司 Arylamine organic compound and application thereof
KR20230029396A (en) * 2021-08-24 2023-03-03 주식회사 동진쎄미켐 New organic compound for capping layer and Organic light emitting diode comprising to the same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20040098238A (en) 2003-05-14 2004-11-20 주식회사 대우일렉트로닉스 Filter assembly for oxygen generator
JP2008007424A (en) * 2006-06-27 2008-01-17 Idemitsu Kosan Co Ltd Aromatic amine derivative and organic electroluminescent device using the same
JP4882898B2 (en) * 2007-07-23 2012-02-22 ソニー株式会社 Organic electroluminescence device and display device
US7960566B2 (en) * 2008-10-17 2011-06-14 Semiconductor Energy Laboratory Co., Ltd. Anthracene derivative and light-emitting devices, electronic devices, and lighting device using the anthracene derivative
JPWO2011040607A1 (en) * 2009-10-02 2013-02-28 出光興産株式会社 Aromatic amine derivative and organic electroluminescence device
KR101896035B1 (en) * 2011-08-23 2018-09-07 덕산네오룩스 주식회사 Novel compound for organic electronic element, organic electronic element using the same, and terminal thereof
KR20140108117A (en) * 2013-02-28 2014-09-05 에스에프씨 주식회사 Organic electro luminescent compounds and organic electroluminescent device using the same
KR102073322B1 (en) * 2013-06-13 2020-02-03 덕산네오룩스 주식회사 An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same
KR20160120609A (en) * 2015-04-08 2016-10-18 주식회사 엘지화학 Organic electronic device comprising a compound
TWI619701B (en) * 2016-05-27 2018-04-01 Ｌｇ化學股份有限公司 Organic light emitting device
KR102081739B1 (en) * 2017-11-03 2020-02-26 (주)씨엠디엘 2,3 substituted naphthylamine derivative organic compounds and organic electroluminescent device including the same

Also Published As

Publication number Publication date
CN111995530A (en) 2020-11-27
KR20200136115A (en) 2020-12-07

Similar Documents

Publication Publication Date Title
KR102484481B1 (en) New organic compound for capping layer and Organic light emitting diode comprising to the same
KR102364045B1 (en) Compound for forming capping layer and organic electroluminescent divice including the same
KR20210035041A (en) New organic compound for capping layer and electroluminescent device comprising to the same
KR20200062616A (en) Organic compound for capping layer and organic electroluminescent divice including the same
KR20220035066A (en) Compound for forming capping layer and organic electroluminescent divice including the same
KR20200050407A (en) Compound for capping layer and organic electroluminescent divice including the same
TW202104162A (en) Organic compound for capping layer and organic electroluminescent device including the same
KR20230115273A (en) New compound for capping layer and Organic light emitting diode comprising to the same
TW201903124A (en) Coating layer forming compound and organic light emitting element containing same
TW201918542A (en) Novel compound and organic electroluminescent device including the same capable of ensuring high efficiency, prolonged service life, low driving voltage and driving stability of the organic electroluminescent device
KR20200034584A (en) Novel compound for capping layer and organic electroluminescent device including the same
TW202110846A (en) Organic compound for capping layer and organic electroluminescent device including the same
KR20220015971A (en) New compound for capping layer and Organic light emitting diode comprising to the same
TW202212536A (en) Organic electroluminescent device
TW202106672A (en) Compound for capping layer and organic electroluminescent device including the same
CN111217738A (en) Organic compound for capping layer and organic light emitting device including the same
TW202104163A (en) Compound for capping layer and organic electroluminescent device including the same
KR20220015970A (en) New compound for capping layer and Organic light emitting diode comprising to the same
TW201942328A (en) Novel compound and organic electroluminescent device including the same
JP2018115151A (en) Triazine compound having benzimidazole group
KR102654442B1 (en) New organic compound for capping layer and Organic light emitting diode comprising to the same
KR20230029395A (en) Organic electroluminescent device comprising cappling layer
KR20230056865A (en) New compound for capping layer and Organic light emitting diode comprising to the same
KR20210052309A (en) Novel compound and organic electroluminescent device comprising the same
KR20220015893A (en) New compound for capping layer and Organic light emitting diode comprising to the same