TWI614928B - Organic light emitting device - Google Patents
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- 0 *C1CCCCC1 Chemical compound *C1CCCCC1 0.000 description 5
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c(cccc2)c2c2c1cccc2 Chemical compound C[n]1c(cccc2)c2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- BODXNJXWEBCCQV-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)cc3c2c(-c2c(cccc4)c4ccc2)c(cccc2)c2c3-c2cccc3c2cccc3)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)cc3c2c(-c2c(cccc4)c4ccc2)c(cccc2)c2c3-c2cccc3c2cccc3)nc2c1cccc2 BODXNJXWEBCCQV-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N c(cc1-c2cccc3cccc-4c23)cc2c1c-4ccc2 Chemical compound c(cc1-c2cccc3cccc-4c23)cc2c1c-4ccc2 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N c1cc(ccc2c3nccc2)c3nc1 Chemical compound c1cc(ccc2c3nccc2)c3nc1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明係有關於一種有機發光裝置,且包括第一陰極;第二陰極;以及設於該第一陰極與該第二陰極之間之陽極,其中,第一發光單元係設於該第一陰極與該陽極之間,第二發光單元係設於該第二陰極與該陽極之間,且該第一發光單元與該第二發光單元係彼此並聯,該第一發光單元包括第一發光層,且包括如式1所示之化合物之有機材料層係設於該第一發光層與該陽極之間,該第二發光單元包括第二發光層,且包括如式1所示之化合物之有機材料層係設於該第二發光層與該陽極之間。 The present invention relates to an organic light-emitting device, and includes a first cathode; a second cathode; and an anode disposed between the first cathode and the second cathode, wherein the first light-emitting unit is disposed at the first cathode A second light emitting unit is disposed between the second cathode and the anode, and the first light emitting unit and the second light emitting unit are connected in parallel with each other, and the first light emitting unit includes a first light emitting layer. And an organic material layer comprising a compound as shown in Formula 1 is disposed between the first light-emitting layer and the anode, the second light-emitting unit includes a second light-emitting layer, and comprises an organic material of a compound as shown in Formula 1. A layer is disposed between the second luminescent layer and the anode.
Description
本發明係關於一種有機發光裝置。 The present invention relates to an organic light-emitting device.
有機發光裝置透過將來自兩電極之電子與電洞注入至有機材料層中而使電流轉換為可見光。該有機發光裝置可具有包括兩層或以上之有機材料層之多層結構,舉例來說,該有機發光裝置除了發光層外,必要時可進一步包括一電子或電洞注入層、一電子或電洞阻擋層、或一電子或電洞傳輸層。 The organic light-emitting device converts current into visible light by injecting electrons and holes from the two electrodes into the organic material layer. The organic light-emitting device may have a multi-layer structure including two or more organic material layers. For example, the organic light-emitting device may further include an electron or hole injection layer, an electron or a hole, in addition to the light-emitting layer. A barrier layer, or an electron or hole transport layer.
近來,該有機發光裝置已有多樣化之用途,並已積極地針對可改善該有機發光裝置之表現之材料加以研究。 Recently, the organic light-emitting device has been used for a variety of purposes, and has been actively studied for materials which can improve the performance of the organic light-emitting device.
本發明提供一種具有新穎性結構之有機發光裝置。 The present invention provides an organic light-emitting device having a novel structure.
本發明之一示例性實施例包括:第一陰極;第二陰極;以及設於該第一陰極與該第二陰極之間之陽極,其中,第一發光單元係設於該第一陰極與該陽極之 間,第二發光單元係設於該第二陰極與該陽極之間,且該第一發光單元與該第二發光單元係彼此並聯,該第一發光單元包括第一發光層,且包括如下述式1所示之化合物之有機材料層係設於該第一發光層與該陽極之間,並且該第二發光單元包括第二發光層,且包括如下述式1所示之化合物之有機材料層係設於該第二發光層與該陽極之間。 An exemplary embodiment of the present invention includes: a first cathode; a second cathode; and an anode disposed between the first cathode and the second cathode, wherein the first light emitting unit is disposed on the first cathode and the anode Anode a second light emitting unit is disposed between the second cathode and the anode, and the first light emitting unit and the second light emitting unit are connected in parallel with each other, the first light emitting unit includes a first light emitting layer, and includes the following An organic material layer of the compound of Formula 1 is disposed between the first light-emitting layer and the anode, and the second light-emitting unit includes a second light-emitting layer and includes an organic material layer of a compound represented by Formula 1 below The system is disposed between the second luminescent layer and the anode.
於式1中,R1至R6係彼此相同或不同,且各自獨立為氫、鹵原子、腈基(-CN)、硝基(-NO2)、磺醯基(-SO2R)、亞碸(-SOR)、磺醯胺(-SO2NR)、磺酸酯(-SO3R)、三氟甲基(-CF3)、酯基(-COOR)、醯胺基(-CONHR或-CONRR')、一經取代或未經取代之直鏈或支鏈C1至C12烷氧基、一經取代或未經取代之直鏈或支鏈之C1至C12烷基、一經取代或未經取代之直鏈或支鏈之C2至C12烯基、一經取代或未經取代之芳族或非芳族雜環、一經取代或未經取代之芳基、一經取代或未經取代之單 -或二芳基胺、或一經取代或未經取代之芳烷基胺,其中R和R'係各自為一經取代或未經取代之C1至C60烷基、一經取代或未取代之芳基、或一經取代或未經取代之5-至7-員雜環。 In Formula 1, R 1 to R 6 are the same or different from each other, and are each independently hydrogen, a halogen atom, a nitrile group (-CN), a nitro group (-NO 2 ), a sulfonyl group (-SO 2 R), Athene (-SOR), sulfonamide (-SO 2 NR), sulfonate (-SO 3 R), trifluoromethyl (-CF 3 ), ester (-COOR), guanamine (-CONHR) Or -CONRR'), a substituted or unsubstituted linear or branched C 1 to C 12 alkoxy group, a substituted or unsubstituted linear or branched C 1 to C 12 alkyl group, once substituted Or unsubstituted linear or branched C 2 to C 12 alkenyl, substituted or unsubstituted aromatic or non-aromatic heterocyclic ring, substituted or unsubstituted aryl group, substituted or unsubstituted a substituted mono- or diarylamine, or a substituted or unsubstituted arylalkylamine, wherein each of R and R' is a substituted or unsubstituted C 1 to C 60 alkyl group, once substituted or not Substituted aryl, or substituted or unsubstituted 5- to 7-membered heterocyclic ring.
根據本發明之有機發光裝置,藉由對稱地連接兩發光單元至陽極(其係一共用電極)之上方及下方而可應用於雙發光型有機發光裝置之中。此外,根據本發明之有機發光裝置,透過包括如式1所示之化合物於該有機材料層中,因而可使用具有各種功函數之電極材料。 The organic light-emitting device according to the present invention can be applied to a two-emission type organic light-emitting device by symmetrically connecting the two light-emitting units to the upper and lower sides of the anode (which is a common electrode). Further, according to the organic light-emitting device of the present invention, an electrode material having various work functions can be used by passing a compound including the compound of the formula 1 in the organic material layer.
圖1係根據相關技術之有機發光裝置之堆疊型結構示意圖。 1 is a schematic view showing a stacked structure of an organic light-emitting device according to the related art.
圖2係根據本發明一示例性實施例之有機發光裝置之堆疊型結構示意圖。 2 is a schematic view showing a stacked structure of an organic light-emitting device according to an exemplary embodiment of the present invention.
圖3係根據本發明一示例性實施例之有機發光裝置之堆疊型結構示意圖。 3 is a schematic view showing a stacked structure of an organic light-emitting device according to an exemplary embodiment of the present invention.
於下文中,本發明所列舉之實施例將詳細地加以說明。 Hereinafter, the embodiments of the present invention will be described in detail.
一般而言,相關技術中的有機發光裝置具有光僅由單一方向發出之結構。於該結構中,當陽極與陰極作為透明 電極使用時可實現雙發光型有機發光裝置。但光線由兩側發出將導致裝置亮度會比單一側之亮度減少一半的現象發生。 In general, an organic light-emitting device in the related art has a structure in which light is emitted only in a single direction. In this structure, when the anode and cathode are transparent A dual light-emitting organic light-emitting device can be realized when the electrode is used. However, when light is emitted from both sides, the brightness of the device will be reduced by half compared to the brightness of the single side.
此外,下圖1中係根據相關技術之有機發光裝置之堆疊型結構示意圖。具體而言,相關技術之有機發光裝置可包括陽極、陰極、以及包括一發光層之有機材料層設於陽極與陰極之間。特別是,相關技術之有機發光裝置可於有機材料層中包括兩發光層以發出白光,但由於發光層之波長之空腔長度彼此不同,且由其中兩側所發出的光的顏色可彼此不同,因而具有難以實現所欲顏色的問題。 In addition, FIG. 1 is a schematic diagram of a stacked structure of an organic light-emitting device according to the related art. Specifically, the related art organic light-emitting device may include an anode, a cathode, and an organic material layer including a light-emitting layer disposed between the anode and the cathode. In particular, the related art organic light-emitting device may include two light-emitting layers in the organic material layer to emit white light, but the cavity lengths of the light-emitting layers may be different from each other, and the colors of the light emitted from the two sides may be different from each other. Therefore, it has a problem that it is difficult to achieve a desired color.
因此,於本發明中,引入將垂直方向上並聯的兩個或以上之發光單元之結構,且特別是,已針對有機發光裝置中,藉由利用陽極作為共用電極而進一步簡化其中之電極結構進行研製。 Therefore, in the present invention, the structure of two or more light-emitting units which are connected in parallel in the vertical direction is introduced, and in particular, in the organic light-emitting device, the electrode structure is further simplified by using the anode as a common electrode. Developed.
根據本發明一示例性實施例之有機發光裝置包括:第一陰極;第二陰極;以及設於該第一陰極與該第二陰極之間之陽極,其中,第一發光單元係設於該第一陰極與該陽極之間,第二發光單元係設於該第二陰極與該陽極之間,且該第一發光單元與該第二發光單元係彼此並聯,該第一發光單元包括第一發光層,且包括如式1所示之化合物之有機材料層係設於該第一發光層與該陽極之間,並且該第二發光單元包括第二發光層,且包括如式1所示之化合物之有機材料層係設於該第二發光層與該陽極之間。 An organic light-emitting device according to an exemplary embodiment of the present invention includes: a first cathode; a second cathode; and an anode disposed between the first cathode and the second cathode, wherein the first light-emitting unit is disposed in the first Between a cathode and the anode, a second light emitting unit is disposed between the second cathode and the anode, and the first light emitting unit and the second light emitting unit are connected in parallel with each other, and the first light emitting unit includes a first light emitting unit a layer, and an organic material layer including a compound as shown in Formula 1 is disposed between the first light-emitting layer and the anode, and the second light-emitting unit includes a second light-emitting layer, and includes a compound as shown in Formula 1. The organic material layer is disposed between the second light emitting layer and the anode.
於本發明中,該至少一包括如式1所示之化合物之 有機材料層係與陽極接觸。此外,設於該第一發光層與該陽極之間之該包括如式1所示之化合物之有機材料層,以及設於該第二發光層與該陽極之間之該包括如式1所示之化合物之有機材料層,均可與陽極接觸。 In the present invention, the at least one includes a compound as shown in Formula 1. The organic material layer is in contact with the anode. In addition, the organic material layer including the compound shown in Formula 1 between the first light-emitting layer and the anode, and the between the second light-emitting layer and the anode are included as shown in Formula 1. The organic material layer of the compound can be in contact with the anode.
於本發明中,式1之化合物可舉例為如下式1-1置1-6之化合物,但並不限於此。 In the present invention, the compound of the formula 1 can be exemplified by the following compounds of the formula 1-6, but is not limited thereto.
[式1-6]
式1之其他實例、或合成方法以及各種特性已描述於美國專利申請號2002-0158242以及美國專利號6,436,559與4,780,536之中,且上述文件中所有內容已併入本案發明中。 Other examples of Formula 1, or methods of synthesis, and various features are described in U.S. Patent Application No. 2002-0158242, and U.S. Patent Nos. 6,436,559 and 4,780,536, the entire contents of each of which are incorporated herein.
於下文中,將詳細地描述組成根據本發明一示例性實施例之有機發光裝置之每一層。下述每一層之材料可為單一材料或是兩種或以上之材料之組成。 Hereinafter, each layer constituting the organic light-emitting device according to an exemplary embodiment of the present invention will be described in detail. The material of each of the following layers may be a single material or a combination of two or more materials.
於本發明中,n型意指n型半導體特性。換言之,一n型半導體係一具有電子於LUMO能階注入或傳輸之特性之有機材料層,且該有機材料層具有電子遷移率高於電洞遷移率之材料之特性。反之,p型意指p型半導體特性。換言之,一p型半導體係一具有電洞於最高佔據分子軌道(HOMO)能階注入或傳輸之特性之有機材料層,且該有機材料層具有電洞遷移率高於電子遷移率之材料之特性。於本發明中,「一有機材料層其於HOMO能階傳輸電荷」與p型有機材料層可具有同樣的意義;且「一有機材料層其於LUMO能階傳輸電荷」與n型有機材料層可具有同樣的意 義。 In the present invention, n-type means n-type semiconductor characteristics. In other words, an n-type semiconductor is an organic material layer having electrons injected or transferred in a LUMO energy level, and the organic material layer has characteristics of a material having an electron mobility higher than a hole mobility. Conversely, p-type means p-type semiconductor characteristics. In other words, a p-type semiconductor is an organic material layer having the characteristics of a hole in the highest occupied molecular orbital (HOMO) energy level injection or transmission, and the organic material layer has the characteristics of a material having a hole mobility higher than the electron mobility. . In the present invention, "an organic material layer transporting charge at HOMO energy level" has the same meaning as a p-type organic material layer; and "an organic material layer transports charge at LUMO energy level" and an n-type organic material layer Can have the same meaning Righteousness.
於本發明中,能階指的是能量的大小。據此,即使當能階以由真空度之負方向(negative(-)direction)表示時,該能階被解釋為相對於能量值之一絕對值。舉例來說,該HOMO能階指的是由未佔據能階(vacuum level)至最高佔據分子軌道之距離。並且,該LUMO能階指的是由未佔據能階(vacuum level)至最低未佔據分子軌道之距離。 In the present invention, the energy level refers to the magnitude of energy. According to this, even when the energy level is expressed by the negative direction of the degree of vacuum (negative (-) direction), the energy level is interpreted as an absolute value with respect to one of the energy values. For example, the HOMO energy level refers to the distance from the unoccupied vacuum level to the highest occupied molecular orbital. Also, the LUMO energy level refers to the distance from the unoccupied vacuum level to the lowest unoccupied molecular orbital.
於本發明中,電荷指的是電子或電洞。 In the present invention, a charge refers to an electron or a hole.
陽極anode
陽極包括金屬、金屬氧化物、或傳導性聚合物。該傳導性聚合物可包括導電性聚合物。舉例來說,陽極可具有功函數值約為3.5eV至約5.5eV。傳導材料之實例包括碳、鋁、釩(vanadium)、鉻、銅、鋅、銀、金、其他金屬、或其合金;氧化鋅、氧化銦、氧化錫、銦錫氧化物(ITO)、以及其他類似金屬氧化物;氧化物與金屬之混合物,如ZnO:Al及SnO2:Sb,以及類似者。關於作為陽極之材料,可使用透明或不透明的材料。於光朝陽極方向發射之結構之情況下,可形成透明之陽極。在此,只要具備由有機發光層所發射之光可被傳遞之充分的透明度即可,且該光之透射率並無特別限制。 The anode includes a metal, a metal oxide, or a conductive polymer. The conductive polymer can include a conductive polymer. For example, the anode can have a work function value of from about 3.5 eV to about 5.5 eV. Examples of conductive materials include carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, other metals, or alloys thereof; zinc oxide, indium oxide, tin oxide, indium tin oxide (ITO), and others Similar to metal oxides; mixtures of oxides and metals, such as ZnO:Al and SnO 2 :Sb, and the like. Regarding the material as the anode, a transparent or opaque material can be used. In the case of a structure in which light is emitted toward the anode, a transparent anode can be formed. Here, as long as the light emitted from the organic light-emitting layer can be transmitted with sufficient transparency, the transmittance of the light is not particularly limited.
特別是,本發明有機發光裝置可透過包括該陽極做為一共用電極,以更有效地應用於雙發光型有機發光裝置。 In particular, the organic light-emitting device of the present invention can be more effectively applied to a dual-emissive organic light-emitting device by including the anode as a common electrode.
於本發明中,p型有機材料層可各自設於第一 發光層或該第二發光層與陽極之間。該p型有機材料層可為一電洞注入層(HIL)或一電洞傳輸層(HTL)。 In the present invention, the p-type organic material layers may each be set at the first Between the luminescent layer or the second luminescent layer and the anode. The p-type organic material layer may be a hole injection layer (HIL) or a hole transport layer (HTL).
關於p型有機材料層之材料,可使用芳基胺化合物。關於芳基胺化合物之實例,其係如下式2之化合物。 As the material of the p-type organic material layer, an arylamine compound can be used. As an example of an arylamine compound, it is a compound of the following formula 2.
於式2中,Ar1、Ar2、及Ar3各自獨立為氫或烴基(hydrocarbon group),Ar1、Ar2、及Ar3至少一者可包括一芳族烴取代基,且各自之取代基可彼此相同或可由不同取代基所組成。 In Formula 2, Ar 1 , Ar 2 , and Ar 3 are each independently hydrogen or a hydrocarbon group, and at least one of Ar 1 , Ar 2 , and Ar 3 may include an aromatic hydrocarbon substituent, and each of them is substituted. The groups may be identical to each other or may be composed of different substituents.
式2之具體實例包括如下之化學式,且本發明所述之示例性實施例並不總限於此。 Specific examples of Formula 2 include the following chemical formulas, and the exemplary embodiments of the present invention are not always limited thereto.
該p型有機材料層異於相關技術中以p型摻雜物摻雜之有機材料之具有p型半導體特性之層。該p型有機材料層藉由p型摻雜物並未展現p型半導體特性,然而該p型有機材料層本身包括一具有p型半導體特性之有機材料。 The p-type organic material layer is different from the layer having the p-type semiconductor property of the organic material doped with the p-type dopant in the related art. The p-type organic material layer does not exhibit p-type semiconductor characteristics by the p-type dopant, however the p-type organic material layer itself includes an organic material having p-type semiconductor characteristics.
發光層(EML)Light-emitting layer (EML)
由於電洞傳輸與電子傳輸同時發生於本發明之第一發光層與第二發光層中,該第一發光層與該第二發光層可同時具有n型特性與p型特性。方便起見,當電子傳輸比電洞傳輸快時,發光層可被定義為一n型發光層;而當電洞傳輸比電子傳輸快時,發光層可被定義為一p型發光層。 Since the hole transmission and the electron transmission occur simultaneously in the first light-emitting layer and the second light-emitting layer of the present invention, the first light-emitting layer and the second light-emitting layer can have both n-type characteristics and p-type characteristics. For convenience, when the electron transport is faster than the hole transport, the light-emitting layer can be defined as an n-type light-emitting layer; and when the hole transport is faster than the electron transport, the light-emitting layer can be defined as a p-type light-emitting layer.
n型發光層包括:三-(8-羥基喹啉)鋁(Alq3);8-羥基喹啉鈹(BAlq);苯并噁唑類化合物(benzoxazole-based compound);苯並噻唑類化合物(benzthiazole-based compound)或苯並咪唑類化合物(benzimidazole-based compound);聚芴類化合物(polyfluorene-based compound);矽雜環戊二烯類化合物(sila cyclopentadiene(silole)-based compound)、及類似者,但本發明不限於此。 The n-type light-emitting layer includes: tris-(8-hydroxyquinoline)aluminum (Alq 3 ); 8-hydroxyquinolinium (BAlq); a benzoxazole-based compound; a benzothiazole compound ( Benzthiazole-based compound or benzimidazole-based compound; polyfluorene-based compound; sila cyclopentadiene (silole)-based compound, and the like However, the invention is not limited thereto.
p型發光層包括:咔唑類化合物(carbazole-based compound);蒽類化合物(anthracene-based compound);聚苯基乙烯類聚合物(polyphenylenevinylene (PPV)-based polymer);或螺環化合物(spiro compound)、及類似者,但本發明並不限於此。 The p-type light-emitting layer includes: a carbazole-based compound; an anthracene-based compound; a polyphenylenevinylene (PPV)-based polymer; or a spiro compound (spiro) Compound), and the like, but the invention is not limited thereto.
電子傳輸層(ETL)與電洞傳輸層(EIL)Electron Transport Layer (ETL) and Hole Transport Layer (EIL)
於本發明中,n型有機材料層可分別設於該第一發光層或該第二發光層與陰極之間。該n型有機材料層可為一電子注入層(EIL),或一電子傳輸層(ETL)。 In the present invention, the n-type organic material layer may be respectively disposed between the first light-emitting layer or the second light-emitting layer and the cathode. The n-type organic material layer may be an electron injection layer (EIL) or an electron transport layer (ETL).
該用於n型有機材料層之材料較佳為具有高電子遷移率之材料以傳輸電子。電子傳輸層包括:三-(8-羥基喹啉)鋁(Alq3);一包括Alq3結構之有機化合物;一羥基黃銅-金屬複合物(hydroxyflavone-metal complex);或一矽雜環戊二烯類化合物(sila cyclopentadiene(silole)-based compound);以其類似者,然而並不限於此。 The material for the n-type organic material layer is preferably a material having a high electron mobility to transport electrons. The electron transport layer comprises: tris-(8-hydroxyquinoline)aluminum (Alq 3 ); an organic compound including an Alq 3 structure; a hydroxyflavone-metal complex; or a heterocyclic pentane A sila cyclopentadiene (silole)-based compound; similar thereto, but is not limited thereto.
此外,作為n型有機材料層之材料,可利用習知用於n型有機材料層之材料作為電子注入或傳輸材料。舉例來說,可使用如下所述之材料,但並不限於此。譬如,關於n型有機材料層之材料之具體實例,可使用具有選自由下列官能基之化合物:咪唑基(imidazole group)、噁唑基(oxazole group)、噻唑基(thiazole group)、喹啉基(quinoline group)及菲咯啉基(phenanthroline group)。 Further, as a material of the n-type organic material layer, a material conventionally used for the n-type organic material layer can be utilized as an electron injecting or transporting material. For example, materials as described below may be used, but are not limited thereto. For example, as a specific example of the material of the n-type organic material layer, a compound having an epoxy group selected from the group consisting of an imidazole group, an oxazole group, a thiazole group, and a quinolyl group can be used. (quinoline group) and phenanthroline group.
具有選自由咪唑基、噁唑基、噻唑基之化合物 之具體實例係如下式3或4之化合物。 Having a compound selected from the group consisting of imidazolyl, oxazolyl, and thiazolyl A specific example is a compound of the following formula 3 or 4.
於式3中,R1至R4可彼此相同或不同,且各自獨立為氫;一C1至C30烷基,其係經一或以上之基團取代或未經取代,該基團選自由:鹵素、氨基(amino group)、腈基(nitrile group)、硝基(nitro group)、C1至C30烷基、C2至C30烯基、C1至C30烷氧基、C3至C30環烷基、C3至C30雜環烷基、C5至C30芳基、以及C2至C30雜芳基所組成之群組;一C3至C30環烷基,其係經一或以上之基團取代或未經取代,該基團選自由:鹵素、氨基、腈基、硝基、C1至C30烷基、C2至C30烯基、C1至C30烷氧基、C3至C30環烷基、C3至C30雜環烷基、C5至C30芳基、以及C2至C30雜芳基所組成之群組;一C5至C30芳基,其係經一或以上之基團取代或未經取代,該基團選自由:鹵素、氨基、腈基、硝基、C1至C30烷基、C2至C30烯基、C1至C30烷氧基、C3至C30環烷基、C3至C30雜環烷基、C5至C30芳基、以及C2至C30雜芳基所組成之群組;或一C2至C30雜芳基,其係經一或以上之基團取代或未經取代,該基團選自由:鹵素、氨基、腈基、硝基、C1至C30烷基、C2至C30烯基、C1至C30烷氧基、C3至C30環烷基、C3至C30雜 環烷基、C5至C30芳基、以及C2至C30雜芳基所組成之群組;且可形成一脂肪族、芳族、脂肪族雜環、或芳族雜環縮合環或一螺環鍵結合相鄰基團;Ar1係氫原子、經取代或未經取代之芳族環、或一經取代或未經取代之芳族雜環;X係O、S、或NRa;且Ra可為氫、一C1至C7脂肪族烴、一芳族環、或一芳族雜環。 In Formula 3, R1 to R4 may be the same or different, and each independently hydrogen; a C 1 to C 30 alkyl, which is substituted by one or more lines of substituted or unsubstituted, selected from the group consisting of: Halogen, amino group, nitrile group, nitro group, C 1 to C 30 alkyl group, C 2 to C 30 alkenyl group, C 1 to C 30 alkoxy group, C 3 to a group consisting of a C 30 cycloalkyl group, a C 3 to C 30 heterocycloalkyl group, a C 5 to C 30 aryl group, and a C 2 to C 30 heteroaryl group; a C 3 to C 30 cycloalkyl group, Substituted or unsubstituted by one or more groups selected from the group consisting of: halogen, amino, nitrile, nitro, C 1 to C 30 alkyl, C 2 to C 30 alkenyl, C 1 to C 30 group consisting of alkoxy, C 3 to C 30 cycloalkyl, C 3 to C 30 heterocycloalkyl group, C 5 to C 30 aryl, and C 2 to C 30 heteroaryl group; a C 5 a C 30 aryl group substituted or unsubstituted with one or more groups selected from the group consisting of halogen, amino, nitrile, nitro, C 1 to C 30 alkyl, C 2 to C 30 Alkenyl, C 1 to C 30 alkoxy, C 3 to C 30 cycloalkyl, C 3 to C 30 heterocycloalkyl, C 5 to C 30 aryl, and C 2 to C 30 a group consisting of heteroaryl groups; or a C 2 to C 30 heteroaryl group substituted or unsubstituted with one or more groups selected from the group consisting of halogen, amino, nitrile, nitro , C 1 to C 30 alkyl, C 2 to C 30 alkenyl, C 1 to C 30 alkoxy, C 3 to C 30 cycloalkyl, C 3 to C 30 heterocycloalkyl, C 5 to C 30 a group consisting of an aryl group and a C 2 to C 30 heteroaryl group; and may form an aliphatic, aromatic, aliphatic heterocyclic ring, or an aromatic heterocyclic fused ring or a spiro ring bonding adjacent group Ar 1 is a hydrogen atom, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted aromatic heterocyclic ring; X is O, S, or NR a ; and R a can be hydrogen, a C a 1 to C 7 aliphatic hydrocarbon, an aromatic ring, or an aromatic heterocyclic ring.
於式4中,X係O、S、NRb、或一C1至C7二價烴基;A、D、及Rb係各自為氫、腈基(-CN)、硝基(-NO2)、一C1至C24烷基、一經取代之芳族環,其包括C5至C20芳族環或雜原子、鹵素、或伸烷基或一包括雜原子之伸烷基,其可與相鄰之環結合而形成稠環;A及D可彼此相連以形成芳族環或雜芳環;當n為2或以上時,B係經取代或未經取代之伸烷基或亞芳基,其共軛或非共軛地連接複數雜環以作為連接單元,且當n為1時,B係一經取代或未經取代之烷基或芳基;且n係從1至8之整數。 In Formula 4, X is O, S, NR b or a C 1 to C 7 divalent hydrocarbon group; each of A, D, and R b is hydrogen, a nitrile group (-CN), a nitro group (-NO 2 ) a C 1 to C 24 alkyl group, a substituted aromatic ring comprising a C 5 to C 20 aromatic ring or a hetero atom, a halogen, or an alkylene group or an alkyl group including a hetero atom, which may Combines with adjacent rings to form a fused ring; A and D may be bonded to each other to form an aromatic ring or a heteroaryl ring; when n is 2 or more, B is substituted or unsubstituted alkyl or aromatic a group which is conjugated or non-conjugated to a plurality of heterocyclic rings as a linking unit, and when n is 1, B is a substituted or unsubstituted alkyl or aryl group; and n is an integer from 1 to 8. .
化學式3之化合物之實例包括韓國專利申請公 開號2003-006773中已知的化合物;化學式4之化合物之實例亦包括美國專利號5,645,948及WO05/097756中所描述之化合物。上述文件中所有內容均已併入本發明說明書中。 Examples of the compound of Chemical Formula 3 include Korean Patent Application Compounds of the type disclosed in U.S. Patent No. 5,645,948 and WO 05/097756. All of the above documents have been incorporated in the specification of the present invention.
具體而言,式3之化合物亦包括如下式5之化合物。 Specifically, the compound of Formula 3 also includes a compound of Formula 5 below.
於式5中,R5至R7係彼此相同或不同,且各自獨立為氫、一C1至C20脂族烴、一芳族環、一芳族雜環、或一脂肪族或芳族稠環;Ar係一直接鍵結、一芳族環或一芳族雜環;X係O、S、或NRa;且Ra係一氫原子、一C1至C7脂族烴、一芳族環、或一芳族雜環;然而,排除R5及R6同時為氫的情況。 In Formula 5, R 5 to R 7 are the same or different from each other, and are each independently hydrogen, a C 1 to C 20 aliphatic hydrocarbon, an aromatic ring, an aromatic heterocyclic ring, or an aliphatic or aromatic group. a fused ring; an Ar-bond-direct bond, an aromatic ring or an aromatic heterocycle; X-form O, S, or NR a ; and R a is a hydrogen atom, a C 1 to C 7 aliphatic hydrocarbon, An aromatic ring or an aromatic heterocyclic ring; however, the case where both R 5 and R 6 are simultaneously hydrogen is excluded.
此外,式4之化合物亦包括如下式6之化合物。 Further, the compound of Formula 4 also includes a compound of the following Formula 6.
於式6中,Z係O、S、或NRb;且R8及Rb係氫、一C1至C24烷基、一經取代之芳族環,其包括一C5至C20芳族環或一雜原子、一鹵素、或一伸烷基或包括雜原子可與苯並唑(benzazole)環結合形成一稠環之一伸烷基;當n為2或以上時,B係伸烷基、亞芳基、一經取代之伸烷基、或一經取代之亞芳基,其共軛或非共軛地連接苯並唑環作為一連接單元,當n為1時,B係一經取代或未經取代之烷基或芳基;且n係一由1至8之整數。 In Formula 6, Z is O, S, or NR b ; and R 8 and R b are hydrogen, a C 1 to C 24 alkyl group, a substituted aromatic ring, which includes a C 5 to C 20 aromatic group. a ring or a hetero atom, a halogen, or an alkyl group or a hetero atom may be bonded to a benzazole ring to form a fused ring of one alkyl group; when n is 2 or more, B is an alkyl group, An arylene group, a substituted alkylene group, or a substituted arylene group, which is conjugated or non-conjugated to a benzoxazole ring as a linking unit, and when n is 1, the B system is substituted or not Substituted alkyl or aryl; and n is an integer from 1 to 8.
譬如,可使用具有下列結構之咪唑化合物:
具有喹啉基之化合物之實例包括如下列化學式7至13所示之化合物。 Examples of the compound having a quinolyl group include compounds represented by the following Chemical Formulas 7 to 13.
於式7至式13中,n係一由0至9之整數,且m係一2或以上之整數,R9係選自由:具有氫之環狀結構;烷基,如甲基及乙基;環烷基,如環己基及降冰片基(norbornyl);芳烷基(aralkyl group),如芐基(benzyl group);烯基,如乙烯基(vinyl group)及烯丙基(allyl group);環烯基(cycloalkenyl group),如環戊二烯基(cyclopentadienyl group)及環己烯基(cyclohexenyl group);烷氧基,如甲氧基 (methoxy group);烷硫基(alkylthio group),其中烷氧基之醚鍵之氧原子係經硫原子所取代;芳基醚基(aryl ether group),如苯氧基(phenoxy group);芳基硫醚基(aryl thioether group),其中芳醚基之醚鍵之氧原子係經硫原子所取代;芳基,如苯基(phenyl group)、萘基(naphthyl group)、以及聯苯基(biphenyl group);雜環基(heterocyclic group),如呋喃基(furyl group)、噻吩基(thienyl group)、噁唑基(oxazolyl group)、吡啶基(pryridyl group)、喹啉基(quinolyl group)、以及咔唑基(carbazolyl group);鹵素;氰基(cyano group);醛基(aldehyde group);羰基(carbonyl group);羧基(carboxyl group);酯基(ester group);氨基甲醯基(carbamoyl group);氨基(amino group);硝基(nitro group);矽烷基(silyl group),如三甲基甲矽烷基(trimethylsilyl group);矽氧烷基(siloxanyl group),其係一通過醚鍵而具有矽之基團;以及一相鄰之取代基;且該取代基可經取代或未經取代,且當n為2時,該些取代基可彼此相同或不同;且Y係一二價或以上基團之R9基團。 In Formulas 7 to 13, n is an integer from 0 to 9, and m is an integer of 2 or more, and R 9 is selected from the group consisting of: a cyclic structure having hydrogen; an alkyl group such as a methyl group and an ethyl group. a cycloalkyl group such as a cyclohexyl group and a norbornyl group; an aralkyl group such as a benzyl group; an alkenyl group such as a vinyl group and an allyl group; a cycloalkenyl group such as a cyclopentadienyl group and a cyclohexenyl group; an alkoxy group such as a methoxy group; an alkylthio group; Wherein the oxygen atom of the ether bond of the alkoxy group is substituted by a sulfur atom; an aryl ether group such as a phenoxy group; an aryl thioether group, wherein the aryl ether The oxygen atom of the ether bond is substituted by a sulfur atom; an aryl group such as a phenyl group, a naphthyl group, and a biphenyl group; a heterocyclic group such as Furyl group, thienyl group, oxazolyl group, pryridyl group, quinolyl group, And carbazolyl group; halogen; cyano group; aldehyde group; carbonyl group; carboxyl group; ester group; carbamate Group); amino group; nitro group; silyl group, such as trimethylsilyl group; siloxanyl group, which is ether-bonded a group having an anthracene; and an adjacent substituent; and the substituent may be substituted or unsubstituted, and when n is 2, the substituents may be the same or different from each other; and the Y system is one or two Or an R 9 group of the above group.
化學式7至13之化合物已描述於韓國專利申請公開號2007-0118711中,且該文件之內容全部併入本發明中作為參考。 The compounds of Chemical Formulas 7 to 13 have been described in Korean Patent Application Publication No. 2007-0118711, the entire contents of which are hereby incorporated by reference.
具有菲咯啉基(phenanthroline group)之化合物包括如下列式14至24之化合物,但並不限於此。 The compound having a phenanthroline group includes a compound of the following formulas 14 to 24, but is not limited thereto.
[式14]
於式14至17中,m係1或以上之整數,n及p係整數,且n+p係8或以下,當m係1時,R10及R11係選自由:具有氫之環狀結構;烷基如甲基及乙基;環烷基如環己基及降冰片基 (norbornyl);芳烷基(aralkyl group),如芐基(benzyl group);烯基,如乙烯基(vinyl group)及烯丙基(allyl group);環烯基(cycloalkenyl group)如環戊二烯基(cyclopentadienyl group)及環己烯基(cyclohexenyl group);烷氧基,如甲氧基(methoxy group);烷硫基(alkylthio group),其中烷氧基之醚鍵之氧原子係經硫原子所取代;芳基醚基(aryl ether group),如苯氧基(phenoxy group);芳基硫醚基(aryl thioether group),其中芳醚基之醚鍵之氧原子係經硫原子所取代;芳基,如苯基(phenyl group)、萘基(naphthyl group)、以及聯苯基(biphenyl group);雜環基(heterocyclic group),如呋喃基(furyl group)、噻吩基(thienyl group)、噁唑基(oxazolyl group)、吡啶基(pryridyl group)、喹啉基(quinolyl group)、以及咔唑基(carbazolyl group);鹵素;氰基(cyano group);醛基(aldehyde group);羰基(carbonyl group);羧基(carboxyl group);酯基(ester group);氨基甲醯基(carbamoyl group);氨基(amino group);硝基(nitro group);矽烷基(silyl group),如三甲基甲矽烷基(trimethylsilyl group);矽氧烷基(siloxanyl group),其係一通過醚鍵而具有矽之基團;以及一相鄰之取代基;當m為2或以上,R10係一直接鍵結或一二價或以上之上述基團,且當m為1時,R11係相同的,該取代基可經取代或未經取代,且當n或p是2或以上時,該取代基可彼此相同或不同。 In Formulas 14 to 17, m is an integer of 1 or more, n and p are integers, and n+p is 8 or less, and when m is 1, R 10 and R 11 are selected from: a ring having hydrogen Structure; alkyl such as methyl and ethyl; cycloalkyl such as cyclohexyl and norbornyl; aralkyl group, such as benzyl group; alkenyl, such as vinyl group And allyl groups; cycloalkenyl groups such as cyclopentadienyl groups and cyclohexenyl groups; alkoxy groups such as methoxy groups; An alkylthio group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom; an aryl ether group such as a phenoxy group; an aryl sulfide group ( Aryl thioether group), wherein the oxygen atom of the ether bond of the aryl ether group is substituted by a sulfur atom; an aryl group such as a phenyl group, a naphthyl group, and a biphenyl group; A heterocyclic group, such as a furyl group, a thiryl group, an oxazolyl group, a pryridyl group, a quinolyl group (q) Uinolyl group), and carbazolyl group; halogen; cyano group; aldehyde group; carbonyl group; carboxyl group; ester group; Carbamoyl group; amino group; nitro group; silyl group, such as trimethylsilyl group; siloxanyl group, a group having an anthracene through an ether bond; and an adjacent substituent; when m is 2 or more, R 10 is a direct bond or a divalent or higher group, and when m is 1 R 11 is the same, the substituent may be substituted or unsubstituted, and when n or p is 2 or more, the substituents may be the same or different from each other.
化學式14至17之化合物已描述於韓國專利申 請公開號2007-0052764及2007-0118711中,且該些文件之內容全部併入本發明中作為參考。 The compounds of Chemical Formulas 14 to 17 have been described in Korean Patent Application The disclosures of which are incorporated herein by reference.
[式20]
於式18至21中,R1a至R8a及R1b至R10b係各自為氫原子、一經取代或未經取代之具有5至60個核原子之芳基、一經取代或未經取代之吡啶基(pyridyl group)、一經取代或未經取代之喹啉基(quinolyl group)、一經取代或未經取代之具有1至50個碳原子之烷基、一經取代或未經取代之具有3至50個碳原子之環烷基、一經取代或未經取代之具有6至50個核原子之芳烷基(aralkyl group)、一經取代或未經取代之具有1至50個碳原子之烷氧基、一經取代或未經取代之具有5至50個核原子之芳氧基(aryloxy)、一經取代或未經取代之具有5至50個核原子之芳硫基(arylthio group)、一 經取代或未經取代之具有1至50個碳原子之烷氧基羰基(alkoxycarbonyl group)、一氨基,其係經由一經取代或未經取代之具有5至50個核原子之芳基所取代、一鹵原子、一氰基、一硝基、一羥基、或一羧基,且可彼此相互鍵結以形成一芳族環,並且,L係一經取代或未經取代之具有6至60個碳原子之亞芳基、一經取代或未經取代之亞吡啶基(pyridinylene group)、一經取代或未經取代之亞喹啉基(quinolynylene group)、或一經取代或未經取代之亞芴基(fluorenylene group)。式18至21之化合物已描述於日本專利申請公開號2007-39405中,且該文件之內容全部併入本發明中作為參考。 In the formulae 18 to 21, R 1a to R 8a and R 1b to R 10b are each a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted pyridine. Pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group having 3 to 50 a cycloalkyl group of one carbon atom, a substituted or unsubstituted aralkyl group having 6 to 50 nuclear atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, a substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms, once substituted or not Substituting an alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 nuclear atoms, a halogen atom, a cyano group, a mononitro group, a monohydroxy group, or a monocarboxy group, and may be bonded to each other to form a a family ring, and L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinoxaline A quinolynylene group, or a substituted or unsubstituted fluorenylene group. The compounds of the formulae 18 to 21 have been described in Japanese Patent Application Publication No. 2007-39405, the entire contents of which are hereby incorporated by reference.
於化學式22及23中,d1、d3至d10以及g1各自為氫、或一芳族或脂肪族烴基,m及n係0至2之整數,且p係0至3之整數。式22及23之化合物已描述於美國專利 公開號2007/0122656中,且該文件之內容全部併入本發明中作為參考。 In Chemical Formulas 22 and 23, d 1 , d 3 to d 10 and g 1 are each hydrogen or an aromatic or aliphatic hydrocarbon group, m and n are integers of 0 to 2, and p is an integer of 0 to 3. The compounds of the formulae 22 and 23 are described in U.S. Patent Publication No. 2007/0122656, the disclosure of which is incorporated herein in its entirety by reference.
於式24中,R1c至R6c係各自為氫原子、一經取代或未經取代之烷基、一經取代或未經取代之芳烷基、一經取代或未經取代之芳基、一經取代或未經取代之雜環基、或鹵原子,且Ar1c及Ar2c係各自選自由下列結構式。 In the formula 24, R 1c to R 6c are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or An unsubstituted heterocyclic group or a halogen atom, and each of Ar 1c and Ar 2c is selected from the following structural formulae.
於上述結構式中,R17至R23係各自為氫原子、一經取代或未經取代之烷基、一經取代或未經取代之芳烷基、一經取代或未經取代之芳基、一經取代或未經取代之雜環基、或一鹵原子。式24之化合物已描述於日本專利申請公開號2004-107263中,且該文件之內容全部併入本發明中作為參考。 In the above formula, R 17 to R 23 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, and a substituted one. Or an unsubstituted heterocyclic group or a halogen atom. The compound of the formula 24 has been described in Japanese Patent Application Publication No. 2004-107263, the entire contents of which are hereby incorporated by reference.
陰極cathode
於本發明中,陰極材料可選自由具有各種功函數之材料。陰極材料較佳通常係一具有小功函數之材料,以方便電子注入。然而,於本發明中,亦可使用具有大功函數之材料。具體而言,本發明中,作為陰極材料可使用 功函數等於或大於如上所述之p型有機材料層之HOMO能階之材料。譬如,本發明中,具有功函數為2eV至5eV之材料可用以作為陰極材料。該陰極材料包括:金屬,如鎂、鈣、鈉、鉀、鈦、銦、釔、鋰、釓、鋁、銀、錫、及鉛、或其合金;一多層結構材料,如LiF/Al或LiO2/Al及類似者。 In the present invention, the cathode material may be selected from materials having various work functions. The cathode material is preferably a material having a small work function to facilitate electron injection. However, in the present invention, a material having a large work function can also be used. Specifically, in the present invention, as the cathode material, a material having a work function equal to or greater than the HOMO energy level of the p-type organic material layer as described above can be used. For example, in the present invention, a material having a work function of 2 eV to 5 eV can be used as a cathode material. The cathode material comprises: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, and lead, or an alloy thereof; a multilayer structural material such as LiF/Al or LiO 2 /Al and the like.
陰極可以利用與陽極相同之材料而形成。此外,陰極或陽極可包括透明材料。 The cathode can be formed using the same material as the anode. Additionally, the cathode or anode can comprise a transparent material.
於本發明中,陽極可以是不透明的,且該第一陰極與第二陰極可以是透明的。此時,陽極包括金屬,且該陰極可具有50nm至200nm之厚度。此外,第一陰極和第二陰極各自獨立地包括金屬或金屬氧化物,且可各自獨立地具有5nm至200nm之厚度。 In the present invention, the anode may be opaque, and the first cathode and the second cathode may be transparent. At this time, the anode includes a metal, and the cathode may have a thickness of 50 nm to 200 nm. Further, the first cathode and the second cathode each independently comprise a metal or a metal oxide, and may each independently have a thickness of 5 nm to 200 nm.
此外,於本發明中,該陽極、第一陰極、以及第二陰極可均為不透明的。在此,該陽極、第一陰極、以及第二陰極各自獨立地包括金屬或金屬氧化物,且可各自獨立地具有5nm至200nm之厚度。 Further, in the present invention, the anode, the first cathode, and the second cathode may both be opaque. Here, the anode, the first cathode, and the second cathode each independently comprise a metal or a metal oxide, and may each independently have a thickness of 5 nm to 200 nm.
於本發明中,第一發光單元可進一步包括第三發光層。在此,如式1所示之有機材料層可進一步包括於該第一發光層與該第三發光層之間。 In the present invention, the first light emitting unit may further include a third light emitting layer. Here, the organic material layer as shown in Formula 1 may further be included between the first light emitting layer and the third light emitting layer.
此外,於本發明中,第二發光單元可進一步包括第四發光層。在此,如式1所示之有機材料層可進一步包括於該第二發光層與該第四發光層之間。 Further, in the present invention, the second light emitting unit may further include a fourth light emitting layer. Here, the organic material layer as shown in Formula 1 may further be included between the second light emitting layer and the fourth light emitting layer.
關於根據本發明一示例性實施例之有機發光裝置,有機發光裝置更進一步包括該第三發光層與該第四 發光層,其係如圖3之示意圖所示。 In an organic light emitting device according to an exemplary embodiment of the present invention, the organic light emitting device further includes the third light emitting layer and the fourth The luminescent layer is shown in the schematic diagram of FIG.
於本發明中,該第一發光層、該第二發光層、該第三發光層與該第四發光層可發出具有相同或不同顏色的光線。 In the present invention, the first luminescent layer, the second luminescent layer, the third luminescent layer and the fourth luminescent layer may emit light having the same or different colors.
特別是,根據本發明之有機發光裝置具有一結構,其中該第一發光單元與該第二發光單元係彼此對稱於陽極。 In particular, the organic light-emitting device according to the present invention has a structure in which the first light-emitting unit and the second light-emitting unit are symmetrical to each other with respect to the anode.
同時,於有機發光裝置中,可利用根據發光顏色以控制裝置之共振腔(cavity)之方法,作為提升發光效率之方法之一。該發光效率可進一步地透過控制裝置之共振腔,以使其適用於發光顏色之波長而提升。在此,該裝置之共振腔意指光在裝置中可共振的長度。 Meanwhile, in the organic light-emitting device, a method of controlling the cavity of the device according to the color of the light can be utilized as one of methods for improving the light-emitting efficiency. The luminous efficiency can be further transmitted through the resonant cavity of the control device to enhance its application to the wavelength of the luminescent color. Here, the resonant cavity of the device means the length of light that can be resonated in the device.
如上所述,當相關技術之有機發光裝置係如圖1所示,其包括兩發光層,其空腔長度彼此相異,因此產生難以實現所欲顏色的問題。 As described above, when the related art organic light-emitting device is as shown in Fig. 1, it includes two light-emitting layers whose cavity lengths are different from each other, thus causing a problem that it is difficult to achieve a desired color.
然而,本發明具有一特性在於:於圖1及圖2之結構中,可藉由包括陽極作為中間電極並連接兩平行之發光單元,以將該空腔長度控制為彼此相同,且因此可實現所欲的顏色。 However, the present invention has a feature that, in the structures of FIGS. 1 and 2, the lengths of the cavities can be controlled to be identical to each other by including an anode as an intermediate electrode and connecting two parallel light-emitting units, and thus can be realized. The desired color.
於下文中,上述示例性實施例之具體實例將詳細地加以說明。然而,下述之實例僅用以說明,並非意圖限制本發明示例性實施例之範圍。 Hereinafter, specific examples of the above exemplary embodiments will be described in detail. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the exemplary embodiments of the invention.
<實施例1><Example 1>
於一基板上,形成一厚度為1,500Å之IZO作 為第一陰極。接著,於其上方,藉由以10重量百分比之Ca摻雜如下式之電子傳輸材料而形成厚度為50Å之電子傳輸層,接著,利用如下式之電子傳輸材料以形成厚度為250Å之有機材料層。 Forming a 1,500 Å IZO on a substrate It is the first cathode. Next, on top of this, an electron transporting layer having a thickness of 50 Å is formed by doping an electron transporting material of the following formula with 10% by weight of Ca, and then an electron transporting material of the following formula is used to form an organic material layer having a thickness of 250 Å. .
於其上方,利用如下式之BCP以形成厚度為75Å之電洞阻擋層。接著,藉由以20重量百分比之如下式之Ir(ppy)3摻雜如下式之CBP以形成厚度為300Å之有機材料層。 Above it, a BCP of the following formula is used to form a hole barrier layer having a thickness of 75 Å. Next, a CBP of the following formula was doped with 20 wt% of Ir(ppy) 3 of the following formula to form an organic material layer having a thickness of 300 Å.
於其上方,利用真空沉積如下式之NPB以形成厚度為300Å之p型電洞傳輸層,並接著於其上方,利用熱真空沉積如下式之HAT以形成厚度為300Å之n型電洞傳輸層,從而製得第一發光部。 Above it, a NPB of the following formula is vacuum deposited to form a p-type hole transport layer having a thickness of 300 Å, and then a HAT of the following formula is thermally deposited thereon to form an n-type hole transport layer having a thickness of 300 Å. Thereby, the first light-emitting portion is produced.
接著,利用Al形成一共用電極,其厚度為700Å。 Next, a common electrode is formed using Al, and has a thickness of 700 Å.
隨後,沉積HAT作為n型電洞注入層,其厚度為300Å;並利用NPB作為p型電洞傳輸層,其厚度為300Å。 Subsequently, HAT was deposited as an n-type hole injection layer with a thickness of 300 Å; and NPB was used as a p-type hole transport layer with a thickness of 300 Å.
藉由以10重量百分比之如下式之Ir(ppy)3摻雜如下式之CBP以形成厚度為300Å之發光層。 A light-emitting layer having a thickness of 300 Å was formed by doping CBP of the following formula with 10 wt% of Ir(ppy) 3 of the following formula.
隨後,將BCP做為電洞阻擋層,其厚度為50Å,並利用如下式之電子傳輸材料以形成厚度為250Å之有機材料層。隨後,藉由以10重量百分比之Ca摻雜如下式之電子傳輸材料而形成電子注入層,從而製得第二發光部。 Subsequently, BCP was used as a hole barrier layer having a thickness of 50 Å, and an electron transporting material of the following formula was used to form an organic material layer having a thickness of 250 Å. Subsequently, an electron injecting layer was formed by doping an electron transporting material of the following formula with 10% by weight of Ca, thereby producing a second light emitting portion.
最後,透過形成Ag作為第二陰極,其厚度為 100Å,以製得一雙發光型有機發光裝置。 Finally, by forming Ag as the second cathode, the thickness is 100Å to produce a pair of light-emitting organic light-emitting devices.
所製得之裝置之量子效率(@10mA/cm2),第一陰極之電極表面發出光線之效率為15%,且該第二陰極之電極表面發出光線之效率為12%,其兩個表面均可獲得高光效率。兩個表面上發射之光之效率之間差異約為1.25:1。此時,測得裝置之驅動電壓係8.5V。 The quantum efficiency (@10 mA/cm 2 ) of the device produced, the efficiency of the surface of the electrode of the first cathode is 15%, and the efficiency of the surface of the electrode of the second cathode is 12%, and the two surfaces thereof High light efficiency is achieved. The difference in efficiency between the light emitted on the two surfaces is approximately 1.25:1. At this time, the driving voltage of the device was measured to be 8.5V.
[電子傳輸材料] [BCP]
<實施例2><Example 2>
以與實施例1相同的方法製造一雙發光型有機發光裝置,不同的是,作為中間共用電極之電極係由Ag組成,其厚度為100Å,以作為透明電極。 A double-emitting organic light-emitting device was fabricated in the same manner as in Example 1, except that the electrode as the intermediate common electrode was composed of Ag and had a thickness of 100 Å as a transparent electrode.
所製得之裝置之量子效率(@10mA/cm2),第一陰極之電極表面發出光線之效率為9%,且該第二陰極之電極表面發出光線之效率為7%。其兩個表面上之光之效率約為1.3:1。此時,測得裝置之驅動電壓係8.5V。 The quantum efficiency (@10 mA/cm 2 ) of the device produced was such that the efficiency of the surface of the electrode of the first cathode was 9%, and the efficiency of the surface of the electrode of the second cathode was 7%. The efficiency of light on both surfaces is about 1.3:1. At this time, the driving voltage of the device was measured to be 8.5V.
<比較例1><Comparative Example 1>
以與實施例1相同的方法製得一雙發光型有機發光裝置,不同的是,於頂部及底部方向與共用電極接觸作為中間電極之HAT層不形成。與所製得之裝置中,電洞不能順利地由作為陽極之Al注入至作為電洞傳輸層的NPB,使得正常的發光動作無法進行。 A double-emitting type organic light-emitting device was obtained in the same manner as in Example 1, except that the HAT layer which was in contact with the common electrode as the intermediate electrode in the top and bottom directions was not formed. In the device produced, the hole could not be smoothly injected from the Al as the anode to the NPB as the hole transport layer, so that the normal light-emitting operation could not be performed.
<比較例2><Comparative Example 2>
於一基板上,形成一厚度為1,500Å之IZO作為一陰極。 On a substrate, an IZO having a thickness of 1,500 Å was formed as a cathode.
接著,沉積HAT作為n型電洞注入層,其厚 度為300Å;並利用NPB作為p型電洞傳輸層,其厚度為300Å。 Next, HAT is deposited as an n-type hole injection layer, which is thick The degree is 300 Å; and NPB is used as the p-type hole transport layer, and its thickness is 300 Å.
藉由以10重量百分比之如上式之Ir(ppy)3摻雜CBP以形成厚度為300Å之發光層。 The light-emitting layer was formed to have a thickness of 300 Å by doping CBP with 10 weight percent of Ir(ppy) 3 of the above formula.
接著,利用BCP以形成厚度為50Å之電洞阻擋層,並利用如上式之電子傳輸材料形成厚度為250Å之有機材料層。隨後,藉由以10重量百分比之Ca摻雜如上式之電子傳輸材料而形成電子注入層,從而製得第二發光部。 Next, BCP was used to form a hole barrier layer having a thickness of 50 Å, and an organic material layer having a thickness of 250 Å was formed using the electron transport material of the above formula. Subsequently, an electron injecting layer was formed by doping an electron transporting material of the above formula with 10% by weight of Ca, thereby producing a second light emitting portion.
最後,透過形成Ag作為第二陰極,其厚度為100Å,以製得一雙發光型有機發光裝置。所製得之裝置之量子效率(@10mA/cm2),第一陰極之電極表面發出光線之效率為9%,且該第二陰極之電極表面發出光線之效率為3%。其兩個表面上之光效率比約為3:1。 Finally, a pair of light-emitting organic light-emitting devices was produced by forming Ag as a second cathode and having a thickness of 100 Å. The quantum efficiency (@10 mA/cm 2 ) of the device produced was such that the efficiency of the surface of the electrode of the first cathode was 9%, and the efficiency of the surface of the electrode of the second cathode was 3%. The light efficiency ratio on both surfaces is approximately 3:1.
如上述結果所示,根據本發明之有機發光裝置,藉由對稱地連接兩發光單元至陽極之上方及下方(其係一共用電極)而應用於雙發光型有機發光裝置中。此外,根據本發明之有機發光裝置,透過包括了包括如式1所示之化合物於該有機材料層中,因而可使用具有各種功函數之電極材料。 As shown in the above results, the organic light-emitting device according to the present invention is applied to a two-emission type organic light-emitting device by symmetrically connecting two light-emitting units to above and below the anode (which is a common electrode). Further, according to the organic light-emitting device of the present invention, the electrode material including the compound represented by Formula 1 is included in the organic material layer, and thus an electrode material having various work functions can be used.
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WO2011146915A1 (en) * | 2010-05-21 | 2011-11-24 | The Board Of Regents Of The University Of Texas System | Monolithic parallel multijunction oled with independent tunable color emission |
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