TW201111471A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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Abstract
Description
201111471 六、發明說明： 【發明所屬之技術領域】 本發明係關於新穎有機電場發光化合物及使用該化 合物之有機電場發光裝置。本發明之有機電場發光化令物 係以化學式（1)表示：201111471 VI. Description of the Invention: [Technical Field] The present invention relates to a novel organic electroluminescent compound and an organic electric field light-emitting device using the same. The organic electric field luminescence system of the present invention is represented by the chemical formula (1):
【先前技術】. 一般而言，有機EL裝置通常具有陽極/電洞注入層 (HIL)/電洞傳輸層（HTL)/發光材料層（EML)/電子傳輸層 (ETL)/電子注入層（EIL)/陰極之構形。發出藍光、綠光或 紅光之有機電场發光裝置的生產可取決於發光材料層如何 形成。 就功能方面而言’電場發光材料可分為主體(h〇st)材[Prior Art] In general, an organic EL device generally has an anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer ( EIL) / cathode configuration. The production of an organic electric field illuminating device that emits blue, green or red light may depend on how the luminescent material layer is formed. In terms of function, the electric field luminescent material can be divided into main body (h〇st)
94942 3 201111471 目前，CBP是最廣為人知的鱗光發光材料之主體材 料。使用包括BCP、BAlq等之電洞阻擋層的高效率oled 已被發表。Pioneer(日本）及其他公司發表了使用BAlq衍 生物作為主體材料之高性能0LED。94942 3 201111471 Currently, CBP is the most widely known material for luminescent materials. High efficiency oled using hole barriers including BCP, BAlq, etc. has been published. Pioneer (Japan) and other companies have published high-performance OLEDs using BAlq derivatives as the host material.
雖然此等材料提供良好的電場發光特性，但由於其玻 璃轉移溫度低且熱安定性不佳’因此於真空高溫沈積製程 期間可能會發生降解。由於〇LED之功率效率（power efficiency)係定義為（Π/電壓）x電流效率，因此功率效率 與電壓成反比。為了降低0LED的功率消耗，乃需要高功率 效率。實際上’使用磷光材料之0LED係提供遠比使用螢光 材料之0LED更佳之電流效率（燭光（cd)/安培（A))。然而， 當使用現存材料（如BAlq、CBP等）作為磷光材料之主體 時’因為需要高驅動電壓，因此相較於使用螢光材料之 0LED ’其在功率效率（流明（lm)/瓦（w))上並不具有顯著優 勢。 再者’ 0LED裝置不具有令人滿意之操作壽命。因此， 仍需開發更安定、更高性能之主體材料。 【發明内容】 因此’本發明之一目的係提供具有比現存主體材料更 4 94942 201111471 為提升之發光效率及裝置操作壽命且具有優異之骨架 當之色座標的有機電場發光化合物，以解決上述問=、 發明之另-目的係提供使用該有機電場發光化合 = 場發光材料之有機電場發光裝置。 …電 本發明係關於化學式（1)所示之有機電場發光入 及使用該化合物之有機電場發光裝置。由於本發 ^ 電場發光化合物展現高發光效率 壽命特性，因此其可用於製造具有二==== 0LED。 丁 可〒的 化學式（1)Although these materials provide good electric field luminescence properties, they may degrade during vacuum high temperature deposition processes due to their low glass transition temperature and poor thermal stability. Since the power efficiency of a 〇LED is defined as (Π/voltage)x current efficiency, power efficiency is inversely proportional to voltage. In order to reduce the power consumption of the OLED, high power efficiency is required. In fact, the OLED using phosphorescent materials provides much better current efficiency (candle (cd) / ampere (A)) than OLEDs using fluorescent materials. However, when using existing materials (such as BAlq, CBP, etc.) as the main body of the phosphorescent material, 'because of the high driving voltage, it is in power efficiency (lumens (lm) / watt (w compared to the OLED using fluorescent materials) )) does not have a significant advantage. Furthermore, the '0 LED device does not have a satisfactory operational life. Therefore, it is still necessary to develop a more stable and higher performance host material. SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic electroluminescent compound having an excellent luminescent color and a device operating life of 4 94942 201111471 which is superior to the existing host material and has an excellent skeleton color coordinate to solve the above problem. =, another object of the invention is to provide an organic electric field illuminating device using the organic electric field illuminating = field luminescent material. The present invention relates to an organic electric field illuminating device according to the chemical formula (1) and an organic electric field illuminating device using the same. Since the present electric field luminescent compound exhibits high luminous efficiency life characteristics, it can be used to manufacture LEDs having two ==== 0. Ding Kezhen's chemical formula (1)
Ar!及An獨立表示化學鍵、具有或不具有取代基之 C6-C40)伸芳基、或具有或不具有取代基之（c2_c4〇) 芳基； I至Rn獨立表示氫、氘、鹵素、具有或不具有取代基 之（C1—C30)烷基、具有或不具有取代基之（C6-C30)芳基、 ”個或多個具有或不具有取代基之（C3_C30)環烷基稠合 之經取代或未經取代之（C6-C30)芳基、具有或不具有取代 5 94942 201111471 基之（C3-C30)雜芳基、具有或不具有取代基之5員至7員 雜環烷基、與一個或多個具有或不具有取代基之芳香環稠 合之5員至7員雜環烷基、具有或不具有取代基之（C3-C30) 環烷基、與一個或多個具有或不具有取代基之芳香環稠合 之（C3-C30)環烧基、氰基、NR21R22、BR23R24、PR25R26、 P(=0)R27R28、RaRbRcSi-、RdY-、ReC(=0)-、RfC(:0)0-、具有 或不具有取代基之（C6-C30)芳基（C1-C30)烷基、具有或不 具有取代基之（C2-C30)烯基、具有或不具有取代基之Ar! and An independently represent a chemical bond, a C6-C40) aryl group with or without a substituent, or a (c2_c4〇) aryl group with or without a substituent; and I to Rn independently represent hydrogen, deuterium, halogen, and Or a (C1-C30) alkyl group having no substituent, a (C6-C30) aryl group having or not having a substituent, and one or more (C3_C30) cycloalkyl groups having or without a substituent Substituted or unsubstituted (C6-C30) aryl, with or without a substituent 5 94942 201111471 (C3-C30)heteroaryl, 5- or 7-membered heterocycloalkyl with or without a substituent a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings having or without a substituent, a (C3-C30) cycloalkyl group having or not having a substituent, and having one or more Or an aromatic ring fused without a substituent (C3-C30) cycloalkyl, cyano, NR21R22, BR23R24, PR25R26, P(=0)R27R28, RaRbRcSi-, RdY-, ReC(=0)-, RfC (:0)0-, (C6-C30)aryl(C1-C30)alkyl group with or without a substituent, (C2-C30)alkenyl group with or without a substituent, with or without a substituent It
可各自經由具有或不具有祠合環之（C3-C30)伸烧基或 (C3-C30)伸烯基與相鄰取代基鍵聯以形成脂環、單環或多 環之芳香環、或單環或多環之雜芳香環；. W 表示-(CR5lR52)m-、-(R51)C = C(R52)-、-N(R53)-、-S-、 -0---Si(R54)(R55)---P(R56)---P(=0)(R5t)---C(=0)-或 _B(R58)_ ; R51至R58及R61至R63係與Rl至Rl6之定義相同； 該雜環烷基及雜芳基可含有一個或多個選自Β、Ν、0、 S、P(=0)、Si及P之雜原子； 1^21至R28獨立表示具有或不具有取代基之（C卜C30)烷 基、具有或不具有取代基之（C6-C30)芳基、或具有或不具 有取代基之（C3-C30)雜芳基，Ra、Rb、Re& Rd獨立表示具 有或不具有取代基之（C1-C30)烷基、或具有或不具有取代 6 94942 201111471 基之（C6-C30)芳基，Y表示s或0，Re& Rf表示具有或不 具有取代基之（n-C30)烷基、具有或不具有取代基之 (C1-C30)烷氧基、具有或不具有取代基之（C6 C3〇)芳基、 或具有或不具有取代基之（C6_C3〇)芳氧基； a及b表示整數〇或2;以及 m表示整數1或2。 【實施方式】 於本發明中，‘烷基，、‘烷氧基，及其他含有‘烷 基，部分（moiety)之取代基係包括直鏈及分支鏈烷基兩 者。於本發明中，‘環烷基，係同時包括具有或不具有取 代基之金剛烧基以及具有或不具有取代基之（C7_C3〇)雙環 烷基。 於本發明中，‘芳基’意指自芳香族烴去掉一個氫原 子所獲得之有機基，其可包括4員至7員，特別是5員或 6員之單環或稍合環’且亦包括藉由單鍵鍵聯之複數個芳 基。具體實例包括，但不限於苯基、萘基、聯苯基、蒽基、 茚基、蕗基、菲基、聯伸三笨基（triphenylenyl)、芘基、 茈基、蒯基（chrysenyl)、稠四苯基（naphthacenyl)、丙二 烯合苐基（fluoranthenyl)等。該萘基包括1-萘基及2-萘 基，該蒽基包括1-蒽基、2~蒽基及9-蒽基，該葬基包括 卜薙基、2-¾基、3-荞基、4~荞基及9_苐基。於本發明中， ‘雜芳基’意指含有作爲芳香環骨架原子之1個至4個選 自B、N、0、S、P(=0)、Si及p之雜原子以及作為剩餘芳 香環骨架原子之碳原子之芳基。該雜芳基可為5員或6員 7 94942 201111471 單環雜芳基或為與笨環稠合之多環雜芳基，且可呈部分飽 和。此外’該雜芳基包括一個以上之藉由單鍵鍵聯之雜芳 基。該雜芳基包括二價芳基，其中於環内之雜原子可經氧 化或四級化以形成例如N-氧化物或四級鹽。具體實例包 括，但不限於單環雜芳基，諸如呋喃基、噻吩基、吡咯基、 咪唑基、吡唑基、嗟唑基、噻二唑基、異B塞唑基、異曙峻 基、噚唑基、曙二唑基、三哄基、四畊基、三唑基、四唑 基、呋咕基、°比啶基、吡D并基、嘧啶基、嗒畊基等；多環 雜芳基’諸如笨并呋喃基、苯并噻吩基、異苯并呋喃基、 苯并咪唑基、苯并噻唑基、笨并異噻唑基、笨并異噚唑基、 苯并卩f唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、 喧琳基、異啥嘛基、琳基（cinn〇linyl)、啥嗤琳基、喧 %琳基、吟唾基、啡咬基及笨并二曙呃基（benz〇diοχο 1 y 1) 等，以及其N-氧化物（例如π比咬基N-氧化物、啥琳基N-氧 化物）及其四級鹽等。 本文所述之“（C1-C30)烷基”可包括（n-C20)烷基或 (C1-C10)烷基，“（C6-C30)芳基，，包括（C6-C20)芳基或 (C6-C12)芳基。“（C3-C30)雜芳基”包括（C3-C20)雜芳基 或（C3-C12)雜芳基，“（C3-C30)環烷基，’包括（C3-C20)環 烷基或（C3-C7)環烷基。“（C2-C3〇)烯基或炔基”包括 (C2-C20)烯基或炔基、（C2-C10)烯基或炔基。 於本文所述之術語‘經取代或未經取代（或具有或不具 有取代基）’中，術語‘經取代，意指具有一個或多個獨立 選自下列者之取代基：氘、_素、具有或不具有齒素取代基 8 94942 201111471 之（C1-C30)烧基、（C6-C30)芳基、具有或不具有（匚6_仁3〇) 芳基取代基之（C3-C30)雜芳基、5員至7員雜環烧基、與一 個或多個芳香環稠合之5員至7員雜環烷基、（C3_C3〇)環烷 基、與一個或多個芳香環稠合之（C3-C30)環烷基、三（C1-C30) 烷基矽烷基、二（C1-C30)烷基（C6-C30)芳基矽烷基、三 (C6-C30)芳基矽烷基、（C2-C30)烯基、（C2-C30)炔基、氰基、 咔唑基、NR31R32、BR33R34、PR35R36、p(=〇)r37R38、（C6_C3〇)芳 基（C1-C30)烧基、（C1-C30)烧基（C6-C30)芳基、（C1-C30) 烷氧基、（C1-C30)烷硫基、（C6-C30)芳氧基、（C6-C30)芳硫 基、（C卜C30)烷氧基羰基、（C1-C30)烷基羰基、（C6-C30) 芳基羰基、（C6-C30)芳氧基羰基、（C1-C30)烷氧基羰基氧 基、（C1-C30)烷基羰基氧基、（C6-C30)芳基羰基氧基、 (C6-C30)^r氧基幾基氧基、竣基、墙基及經基；或者相鄰取 代基鍵聯在一起以形成環；以及r31至R38獨立表示（cl_C3〇) 烧基、（C6-C30)芳基或（C3-C30)雜芳基。Each may be bonded to an adjacent substituent via a (C3-C30) extended or a (C3-C30) extended alkenyl group with or without a chelating ring to form an alicyclic, monocyclic or polycyclic aromatic ring, or Monocyclic or polycyclic heteroaromatic ring; W represents -(CR5lR52)m-, -(R51)C = C(R52)-, -N(R53)-, -S-, -0---Si( R54)(R55)---P(R56)---P(=0)(R5t)---C(=0)- or _B(R58)_ ; R51 to R58 and R61 to R63 are related to Rl The definition to R16 is the same; the heterocycloalkyl and heteroaryl group may contain one or more hetero atoms selected from the group consisting of ruthenium, osmium, 0, S, P(=0), Si and P; 1^21 to R28 are independent (C-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, or (C3-C30)heteroaryl group with or without a substituent, Ra, Rb, Re& Rd independently represents a (C1-C30)alkyl group with or without a substituent, or a (C6-C30) aryl group with or without a substituent 6 94942 201111471, Y represents s or 0, Re& Rf (C-C30) alkoxy group with or without a substituent, (C1-C30) alkoxy group with or without a substituent, (C6 C3〇) aryl group with or without a substituent, or (C6_C3〇)aryloxy with or without a substituent; a and b represent an integer 〇 or 2; and m represents an integer of 1 or 2. [Embodiment] In the present invention, the 'alkyl group, 'alkoxy group, and other substituents containing an 'alkyl group' and a moiety include both a straight chain and a branched alkyl group. In the present invention, the 'cycloalkyl group' includes both an adamantyl group having or not having a substituent and a (C7_C3〇)bicycloalkyl group having or not having a substituent. In the present invention, 'aryl' means an organic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, which may include 4 to 7 members, particularly a 5- or 6-membered monocyclic or slightly ring- Also included are a plurality of aryl groups bonded by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, fluorenyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, chrysenyl, thick Naphthacenyl, fluoranthenyl, and the like. The naphthyl group includes a 1-naphthyl group and a 2-naphthyl group, and the fluorenyl group includes a 1-fluorenyl group, a 2-nonyl group and a 9-fluorenyl group, and the morden group includes a diterpene group, a 2-3⁄4 group, a 3-mercapto group, and 4 ~ 荞 base and 9 苐 base. In the present invention, 'heteroaryl' means one to four hetero atoms selected from B, N, 0, S, P (=0), Si and p as an aromatic ring skeleton atom and as a residual aromatic An aryl group of a carbon atom of a ring skeleton atom. The heteroaryl group can be 5 or 6 members. 7 94942 201111471 Monocyclic heteroaryl or polycyclic heteroaryl fused to a stupid ring, and can be partially saturated. Further, the heteroaryl group includes more than one heteroaryl group bonded by a single bond. The heteroaryl group includes a divalent aryl group in which a hetero atom in the ring can be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include, but are not limited to, monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, thiadiazolyl, iso-Bizozolyl, isoindolyl, Carbazolyl, oxadiazolyl, tridecyl, tetra-negative, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl, pyrimidinyl, hydrazine, etc.; polycyclic An aryl group such as a benzofuranyl group, a benzothienyl group, an isobenzofuranyl group, a benzimidazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazole group, a benzoxazole group, Isoindolyl, fluorenyl, carbazolyl, benzothiadiazolyl, fluorenyl, hydrazine, cinn〇linyl, 啥嗤琳, 喧% 琳, 吟 基, a brown bite base and a stupid base (benz〇diοχο 1 y 1), etc., and its N-oxides (such as π than bite-based N-oxide, 啥-based N-oxide) and its four stages Salt and so on. "(C1-C30)alkyl" as used herein may include (n-C20)alkyl or (C1-C10)alkyl, "(C6-C30)aryl, including (C6-C20)aryl or (C6-C12) aryl. "(C3-C30)heteroaryl" includes (C3-C20)heteroaryl or (C3-C12)heteroaryl, "(C3-C30)cycloalkyl,'includes C3-C20) cycloalkyl or (C3-C7)cycloalkyl. "(C2-C3〇)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl. In the term 'substituted or unsubstituted (with or without a substituent)' as used herein, the term 'substituted' means having one or more substituents independently selected from the group consisting of hydrazine and hydrazine. (C1-C30) alkyl, (C6-C30) aryl, with or without dentate substituent 8 94942 201111471, with or without (匚6_仁3〇) aryl substituent (C3-C30 a heteroaryl group, a 5- to 7-membered heterocyclic alkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, a (C3_C3〇)cycloalkyl group, and one or more aromatic rings Fused (C3-C30)cycloalkyl, tri(C1-C30)alkyldecane, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecane , (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, p(=〇)r37R38, (C6_C3〇)aryl (C1-C30) (C1-C30)alkyl (C6-C30) aryl, (C1-C30) alkoxy, (C1-C30)alkylthio, (C6-C30) aryloxy, (C6-C30) aryl Sulfur, (C, C30) alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C 30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)^roxy a benzyloxy group, a fluorenyl group, a wall group and a thiol group; or an adjacent substituent grouped together to form a ring; and r31 to R38 independently represent a (cl_C3〇)alkyl group, a (C6-C30) aryl group or (C3) -C30) Heteroaryl.
Rl至Rl6、R21至R28、R51至R58及R61至R63係選自，但不 限於.鼠，氛；鹵素；烧基，如曱基、乙基、丙基、丁基、 戊基、己基、乙基己基、庚基、辛基等；芳基，如笨基、 萘基、第基、聯苯基、菲基、聯三苯基（terphenyl)、芘基、 花基、螺雙苐基（叩丨1*〇|：^{111〇1'€1^1)、丙二稀合荞基、蒯 基、聯伸三苯基等；與一個或多個環烷基稠合之芳基，如 1，2-二氫危基（1，2-(1丨11丫(11'03。6113卩111:1171);雜芳基，如二 苯并噻吩基、二笨并呋喃基、咔唑基、吼啶基、呋喃基、 嗟吩基、喹啉基、三畊基、嘧啶基、嗒啡基、喹噚啉基、 9 94942 201111471 啡啉基等；與一個或多個芳香環稠合之雜環烷基，如N-苯 并吡咯啶基（benzopyrrolidino)、N-苯并六氫吡啶基、N-二本并嗎琳基、N-二苯并氮呼基（dibenzoazepino)等；經 芳基（如苯基、萘基、苐基、聯苯基、菲基、聯三苯基、芘 基、茈基、螺雙g基、丙二烯合苐基、蒯基、聯伸三苯基 等）取代之胺基；經雜芳基（如二笨并噻吩基、二苯并呋喃 基、咔唑基、吡啶基、呋喃基、噻吩基、喹啉基、三畊基、 嘧啶基、嗒哄基、喹噚啉基、啡啉基等）取代之胺基；芳氧 基，如聯笨基氧基等；芳硫基，如聯笨基硫基尊；芳烷基， 如聯苯基曱基 苯曱基等；R1 to Rl6, R21 to R28, R51 to R58 and R61 to R63 are selected from, but not limited to, murine, halal, halogen; alkyl, such as decyl, ethyl, propyl, butyl, pentyl, hexyl, Ethylhexyl, heptyl, octyl, etc.; aryl, such as stupid, naphthyl, decyl, biphenyl, phenanthryl, terphenyl, fluorenyl, aryl, spirobiguanyl (叩丨1*〇|:^{111〇1'€1^1), propylene disulfide fluorenyl, fluorenyl, extended triphenyl, etc.; aryl group fused to one or more cycloalkyl groups, such as 1,2-dihydrogen (1,2-(1丨11丫(11'03.6113卩111:1171); heteroaryl, such as dibenzothiophenyl, di-p-furanyl, carbazolyl) , acridinyl, furyl, porphinyl, quinolyl, tri-pound, pyrimidinyl, morphine, quinoxalinyl, 9 94942 201111471 morpholinyl, etc.; fused to one or more aromatic rings Heterocycloalkyl, such as N-benzopyrrolidino, N-benzohexahydropyridyl, N-dibenzhydrinyl, N-dibenzoazepino, etc.; Base (such as phenyl, naphthyl, anthracenyl, biphenyl, phenanthryl, triphenylene, fluorenyl, An amine group substituted with a fluorenyl group, a spirobis g group, a propadienyl fluorenyl group, a fluorenyl group, a tert-triphenyl group, etc.; a heteroaryl group (such as a diphenylthiophene group, a dibenzofuranyl group, an oxazolyl group) , an amino group substituted with a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a tri-pirty group, a pyrimidinyl group, a decyl group, a quinoxaline group, a porphyrin group, etc.; an aryloxy group such as a phenyloxy group An arylthio group such as a phenyl group; an aralkyl group such as a biphenyl phenyl benzoyl group;
ReiRei
«83 /--K 且此等基團可如化學式⑴所輯—步經取代。 更具體地，R1至心可藉由下列結構例米之，但不限於 此0 10 94942 201111471«83 /--K and these groups can be replaced by the formula (1). More specifically, R1 to the heart can be obtained by the following structural examples, but is not limited to this 0 10 94942 201111471
^-1 .^-1 .
R71至R136獨立表示氫、氘' 鹵素、（C1_C30)烷基、 (C6-C30)芳基、與一個或多個（C3_C3〇)環烷基稠合之 (C6 C30)芳基、（C3—C30)雜芳基、5員至7員雜環烧基、 與個或夕個芳香環稠合之5員至7員雜環烷基、（C3_C3〇) 環烧基、與一個或多個芳香環稠合之（C3-C30)環烷基、氰 基、胺基、（C1-C30)烷基胺基、（C6-C30)芳基胺基、Nr41r42、 BR43R44、PR4sR46、p(=〇)r47r48、三（ci-C30)烧基石夕烧基、二 (C1-C30)烧基（C6-C30)芳基矽烷基、三（C6-C30)芳基矽烷 基、（C6-C30)芳基（C1-C30)烷基、（C1-C30)烷氧基、（C1-C30) 烷硫基、（C6-C30)芳氧基、（C6-C30)芳硫基、（C1-C30)烷 氧基羰基、（C1-C30)烷基羰基、（C6-C30)芳基羰基、（C2-C30) 11 94942 201111471 烯基、（C2-C30)炔基、（C6-C30)芳氧基羰基、（C1-C30)烷 氧基羰基氧基、（C1-C30)烷基羰基氧基、（C6-C30)芳基羰 基氧基、（C6-C30)芳氧基羰基氧基、羧基、硝基或羥基， 或者R71至R136可各自經由具有或不具有稠合環之（C3-C30) 伸烷基或（C3-C30)伸烯基與相鄰取代基鍵聯以形成脂環、 或單環或多環之芳香環；以及 R41至R48獨立表示（C1-C30)烷基、（C6-C30)芳基或 (C3-C30)雜芳基。 味 αγ2-| 係以下列結構例示之，但不限於此。a 係 如化學式（1)所定義。 12 94942 201111471R71 to R136 independently represent hydrogen, 氘' halogen, (C1_C30) alkyl, (C6-C30) aryl, (C6 C30) aryl fused to one or more (C3_C3 fluorene) cycloalkyl, (C3 - C30) Heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl, (C3_C3〇)cycloalkyl, fused to one or more aromatic fused to an individual or an aromatic ring Ring-fused (C3-C30) cycloalkyl, cyano, amine, (C1-C30)alkylamino, (C6-C30) arylamine, Nr41r42, BR43R44, PR4sR46, p(=〇) R47r48, tri(ci-C30) calcene base, di(C1-C30) alkyl (C6-C30) aryl decyl, tris(C6-C30) aryl decyl, (C6-C30) aryl (C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkane Oxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30) 11 94942 201111471 alkenyl, (C2-C30)alkynyl, (C6-C30) aryloxycarbonyl (C1-C30) alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy,carboxyl,nitrate Or a hydroxy group, or R71 to R136, each may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, or a single ring. Or a polycyclic aromatic ring; and R41 to R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl. The taste αγ2-| is exemplified by the following structure, but is not limited thereto. a is as defined in formula (1). 12 94942 201111471
13 94942 20111147113 94942 201111471
本發明之有機電場發光化合物可藉由下列化合物具 體例示之，但不限於此。The organic electroluminescent compound of the present invention can be specifically exemplified by the following compounds, but is not limited thereto.
14 94942 20111147114 94942 201111471
15 94942 20111147115 94942 201111471
16 94942 20111147116 94942 201111471
17 94942 20111147117 94942 201111471
18 94942 20111147118 94942 201111471
本發明之有機電場發光化合物可如下列反應圖（1)所 示製備之。 19 94942 201111471 反應圖（1)The organic electroluminescent compound of the present invention can be produced as shown in the following reaction scheme (1). 19 94942 201111471 Reaction diagram (1)
其中，among them,
Ri至Rie、An、An、a及b係如化學式（1)所定義。 本發明提供一種有機電場發光裝置，其包括第一電 極；第二電極；以及一層或多層插置於該第一電極與該第 二電極間之有機層，其中，該有機層包括一種或多種化學 式（1)所示之有機電場發光化合物。該有機電場發光化合物 係用作電場發光層之主體材料。 此外，該有機層可包括電場發光層，該電場發光層除 了包括一種或多種化學式（1)所示之有機電場發光化合物 外，還可進一步包括一種或多種摻雜劑。用於本發明之有 機電場發光裝置的摻雜劑並無特別限制。 較佳地，用於本發明之有機電場發光裝置的摻雜劑可 選自下述化學式（2)。 化學式（2) M1L101L102L103 其中， 20 94942 201111471 Μ1為選自下列所組成群組之金屬：第7族、第8族、 第9族、第10族、第11族、第13族、第14族、第15 族及第16族之金屬；以及配位子Lm、L1。2及L1。3係獨立選 自下列結構：Ri to Rie, An, An, a and b are as defined in the chemical formula (1). The present invention provides an organic electric field light-emitting device including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer includes one or more chemical formulas (1) An organic electric field luminescent compound as shown. The organic electroluminescent compound is used as a host material of an electroluminescent layer. Further, the organic layer may include an electric field luminescent layer which may further include one or more dopants in addition to one or more organic electroluminescent compounds of the formula (1). The dopant used in the organic electroluminescence device of the present invention is not particularly limited. Preferably, the dopant used in the organic electroluminescence device of the present invention may be selected from the following chemical formula (2). Chemical formula (2) M1L101L102L103 wherein, 20 94942 201111471 Μ1 is a metal selected from the group consisting of: Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Metals of Groups 15 and 16; and ligands Lm, L1. 2 and L1. 3 are independently selected from the following structures:
β21β2121β
^20^20
其中， R2〇i至R2。3獨立表示氫、具有或不具有鹵素取代基之 (C1-C30)烷基、具有或不具有（C1-C30)烷基取代基之 21 94942 201111471 (C6-C30)芳基、或鹵素； 匕04至R219獨立表示氫、具有或不具有取代基之（C1-C30) 烧基、具有或不具有取代基之（C1_C3〇)烷氧基、具有或不 具有取代基之（C3-C30)環烷基、具有或不具有取代基之 (C2-C30)烯基、具有或不具有取代基之（C6_C30)芳基、具 有或不具有取代基之單-或二_(C1_C30)烷基胺基、具有或 不具有取代基之單-或二_(C6_C30)芳基胺基、SF5、具有或 不具有取代基之三（C1-C30)烷基矽烷基、具有或不具有取 代基之二（C1-C30)烷基（C6-C30)芳基矽烷基、具有或不具 有取代基之三（C6-C30)芳基矽烷基、氰基、或_素； 至R223獨立表示氫、具有或不具有鹵素取代基之 (C1-C30)烧基或具有或不具有（cl C3〇)烷基取代基之 (C6-C30)芳基； R224與R225獨立表示氫、具有或不具有取代基之（C卜C30) 烷基、具有或不具有取代基之（C6_C3〇)芳基、或鹵素，或 者Rm與Rm可經由具有或不具有稠合環之（C3_C12)伸烷 基或（C3-C12)伸烯基相鍵聯以形成脂環、或單環或多環之 芳香環；Wherein R 2 〇 i to R 2 . 3 independently represent hydrogen, (C 1 -C 30 )alkyl with or without a halogen substituent, 21 with or without (C 1 -C 30 ) alkyl substituent 94 94 2011 201111471 (C6-C30 Aryl or halogen; 匕04 to R219 independently represent hydrogen, (C1-C30) alkyl group with or without a substituent, (C1_C3〇) alkoxy group with or without a substituent, with or without a substitution (C3-C30)cycloalkyl, (C2-C30)alkenyl with or without a substituent, (C6_C30) aryl with or without a substituent, mono- or di- ordinarily _(C1_C30)alkylamino group, mono- or di-(C6_C30)arylamino group with or without a substituent, SF5, a tri(C1-C30)alkyldecane group with or without a substituent, having Or a substituted (C1-C30)alkyl (C6-C30) arylalkylene group, a tris(C6-C30)aryldecyl group, a cyano group, or a _ element with or without a substituent; R223 independently represents hydrogen (C1-C30)alkyl or a (C6-C30) aryl group with or without a (cl C3 〇) alkyl substituent; R224 is independent of R225 Hydrogen, (C, C30) alkyl with or without a substituent, (C6_C3〇) aryl with or without a substituent, or halogen, or Rm and Rm may be via or without a fused ring ( C3_C12) an alkyl group or a (C3-C12) extending alkenyl group to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring;
Rm表示具有或不具有取代基之（C1-C30)烷基、具有或 不具有取代基之（C6-C30)芳基、具有或不具有取代基之 (C5-C30)雜芳基、或齒素； —尺⑴至1^29獨立表示氫、具有或不具有取代基之（c卜C3〇) 燒基、具有或不具有取代基之（C6〜C3〇)芳基、或_素；以 及 22 94942 201111471 F^3i Q表示 或 其中，R231 至R242獨立表不氫、具有或不具有鹵素取代基之（H-C30) 烧基、（α-⑽燒氣基、齒素、具有或 (C6-C30)芳基、氰兴 糾代巷之 炫基，或者‘至有或不具有取代基之（G5-C3〇)環 代基鍵聯以形成螺壤基或:稀基與相鄰取 伸烧基或伸稀絲，或者^至1"42可各自經由 合環。 ^如或R2°8鍵聯以形成飽和或不飽和稠 電場發光層係指 私 層，該多層係由兩層層，其可為單一層或可為多 發明之構形中，當# : /日積疊（laminate)而成。於本 明之電場㈣主摻賴线合物時，咸信本發 謂之摻雜濃度實現^提升發光效率。其可由⑴5至10 場發光主體具有優越目較於其他主體材料，本發明之電 安定性，因此顯現顯著電及電子傳導性以及優異的材料 M1係選自下列所〜命以及提升發光效率之特徵。 Os、Tl、pb、Bi、！之群組：Ir、pt、Pd、Rh、Re、 in、Sn、Sb、τ 所示之摻雜劑化合物係 e、Au及Ag。化學式（2) 1〇-謂、〇112855號所韓國專利中請案第 於本發明之有機電子m合物例示之，但不限於此。 式⑴所示之有機電場發；;’該有機層除了包括化學 一種或多種選㈣其H物外’還可進一步同時包括 種選自方基胺化合物及苯乙縣芳基胺化合物所 94942 201111471 組成群組之化合物。該等芳基胺化合物或苯乙烯基芳基胺 化合物係例示於韓國專利申請案第10-2008-0123276號、 第 10-2008-0107606 號或第 10-2008-0118428 號中，但不 限於此。 此外，於本發明之有機電場發光裝置中，該有機層除 了包括化學式（1)所示之有機電場發光化合物外，還可進一 步包括一種或多種選自下列所組成群組之金屬：第1族之 有機金屬、第2族、第4周期與第5周期之過渡金屬、鑭 系金屬及d-過渡元素，或錯合物化合物。該有機層可包括 電場發光層及電荷產生層。 此外，該有機層除了包括化學式（1)所示之有機電場 發光化合物外，還可同時包括一層或多層發出藍光、綠光 或紅光之有機電場發光層，以形成發出白光之有機電場發 光裝置。該發出藍光、綠光及紅光之化合物可由韓國專利 申請案第 10-2008-0123276 號、第 10_2〇〇8-〇1〇7606 號或 第10-2008-0118428號所揭示之化合物例示之，但不限於 此。 於本發明之有機電場發光裝置中，可將選自硫屬化合 物（chalcogenide)層、金屬每化物層及金屬氧化物層之層 體（後文中稱為「表面層」）設置於電極對之一個或兩個電 極的内表面上。更具體地，可將矽或鋁金屬之硫屬化合物 (包括氧化物）層設置於電場發光介質層之陽極表面上，並 可將金屬齒化物層或金屬氧化物層設置於電場發光介質層 之陰極表面上。藉此，可得到操作安定性。 24 94942 201111471 硫屬化合物可為例如Si0x(l $；χ^2)、Rm represents a (C1-C30)alkyl group having or not having a substituent, a (C6-C30) aryl group having or not having a substituent, a (C5-C30) heteroaryl group having or not having a substituent, or a tooth a ruler (1) to 1^29 independently represents hydrogen, a (c-C3〇) group with or without a substituent, a (C6-C3〇)aryl group with or without a substituent, or a γ element; 22 94942 201111471 F^3i Q represents or wherein, R231 to R242 independently represent hydrogen (H-C30), (α-(10) gas-burning base, dentate, with or (C6) -C30) aryl, cyanide, sneaker, or 'G5-C3〇' ring with or without a substituent to form a screw base or: dilute and adjacent extension Burning or stretching filaments, or ^ to 1" 42 may each pass through a ring. ^ or R2 °8 linkage to form a saturated or unsaturated thick electric field luminescent layer refers to a private layer, the multilayer is composed of two layers, It may be a single layer or may be a multi-invention configuration, when #: / day is laminated. When the electric field (4) of the present invention is doped with a linear compound, the doping concentration of the salt letter is real Now, the luminous efficiency can be improved. It can be superior to other host materials by (1) 5 to 10 field light-emitting bodies, and the electrical stability of the present invention, thus exhibiting remarkable electrical and electronic conductivity and excellent material M1 is selected from the following And characteristics of improving luminous efficiency. Groups of Os, Tl, pb, Bi, !: dopant compounds represented by Ir, pt, Pd, Rh, Re, in, Sn, Sb, τ, e, Au, and Ag The organic electron compound of the present invention is exemplified in the Korean Patent Application No. 112855, but is not limited thereto. The organic electric field shown in the formula (1);; The layer may further comprise, in addition to the chemical one or more (4) its H species, a compound selected from the group consisting of a arylamine compound and a phenylethylamine arylamine compound 94942 201111471. The arylamine compound or The styryl arylamine compound is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. Further, in the present invention In an organic electric field illuminating device, the organic layer In addition to the organic electroluminescent compound represented by the chemical formula (1), one or more metals selected from the group consisting of: organometallic groups of Group 1, Group 2, Cycle 4, and Cycle 5 may be further included. a transition metal, a lanthanide metal, and a d-transition element, or a complex compound. The organic layer may include an electric field luminescent layer and a charge generating layer. Further, the organic layer includes an organic electroluminescent compound represented by the chemical formula (1). In addition, one or more organic light-emitting layers emitting blue, green or red light may be simultaneously included to form an organic electric field light-emitting device that emits white light. The compound which emits blue light, green light, and red light can be exemplified by the compound disclosed in Korean Patent Application No. 10-2008-0123276, No. 10-2〇〇8-〇1〇7606, or 10-2008-0118428. But it is not limited to this. In the organic electric field light-emitting device of the present invention, a layer selected from a chalcogenide layer, a metal compound layer, and a metal oxide layer (hereinafter referred to as a "surface layer") may be provided in one of the electrode pairs. Or on the inner surface of the two electrodes. More specifically, a chalcogenide (including oxide) layer of ruthenium or aluminum metal may be disposed on the anode surface of the electric field luminescent medium layer, and a metal dentide layer or a metal oxide layer may be disposed on the electric field luminescent medium layer. On the surface of the cathode. Thereby, operational stability can be obtained. 24 94942 201111471 The chalcogen compound may be, for example, Si0x (l $; χ^2),
AlOxUSGl. 5)、SiON、SiAlON等。金屬齒化物可為例 如LiF、MgFz、CaFz、稀土金屬之氟化物等。金屬氧化物可 為例如 Cs2〇、Li2〇、MgO、SrO、BaO、CaO 等。 於本發明之有機電場發光裝置中，亦較佳者為將電子 傳輸化合物與還原性摻雜劑之混合區域或電洞傳輪化合物 與氧化性摻雜劑之混合區域設置於所製造之電極對的至少 一個表面上。於此情況下，由於電子傳輸化合物被還原成 陰離子’因此促使電子更易於自混合區域注入及傳輸至電 場發光介質。此外，由於電洞傳輸化合物被氧化成陽離子， 因此促使電洞更易於自混合區域注入及傳輸至電場發光介 質。較佳的氧化性摻雜劑包括各種路易 士酸（Lewis acid) 及接受者化合物（accept or compound)。較佳的還原性摻雜 劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬、及 其混合物。 此外’具有兩層或更多層電場發光層之發出白光之電 场發光裝置可藉由使用還原性摻雜劑層作為電荷產生層而 製造。 由於本發明之有機電場發光化合物展現良好的發光 效率及優異的壽命特性，因此可用於製造具有非常優異的 操作壽命之0LED裝置。 本發明係藉由參照本發明之有機電場發光化合物、製 備該化合物之製程、以及使用該化合物之裝置的發光特性 而進一步說明。然而，下列實施例僅提供作為例示說明用， 25 94942 201111471 並非意欲用於限制本發明之範圍。 [製備例1]製備化合物1AlOxUSGl. 5), SiON, SiAlON, and the like. The metal tooth compound may be, for example, LiF, MgFz, CaFz, a fluoride of a rare earth metal, or the like. The metal oxide may be, for example, Cs2〇, Li2〇, MgO, SrO, BaO, CaO or the like. In the organic electric field light-emitting device of the present invention, it is also preferred to provide a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant in the electrode pair to be fabricated. At least one surface. In this case, since the electron transporting compound is reduced to an anion', the electrons are more easily injected and transported from the mixed region to the electric field illuminating medium. In addition, since the hole transporting compound is oxidized to a cation, it is easier to inject and transport the hole into the electric field illuminating medium from the mixed region. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, an electric field light-emitting device which emits white light having two or more electric field light-emitting layers can be manufactured by using a reducing dopant layer as a charge generating layer. Since the organic electroluminescent compound of the present invention exhibits good luminescence efficiency and excellent life characteristics, it can be used to manufacture an OLED device having a very excellent operational life. The present invention is further illustrated by reference to the organic electroluminescent compound of the present invention, the process for preparing the compound, and the luminescent properties of the device using the compound. However, the following examples are provided for illustrative purposes only, and 25 94942 201111471 is not intended to limit the scope of the invention. [Preparation Example 1] Preparation of Compound 1
將2-(2_胺基苯基）苯并咪唑（4. 18公克（g)，20.0毫 莫耳（mmol))及苯甲醛（2.3 g，22. 〇 mmol)溶於硝基苯（5〇 毫升（mL))中，然後加熱攪拌該混合物20小時。將反應溫 度降至室溫後，過濾所產生的黃色固體。以乙酸乙酯洗滌 並乾燥，獲得化合物 1(4.2 g，14. 22 mmol，71.10%)。 [製備例2]製備化合物412-(2-Aminophenyl)benzimidazole (4.18 g (g), 20.0 mmol (mmol)) and benzaldehyde (2.3 g, 22. mmol) were dissolved in nitrobenzene (5 The mixture was stirred in liters (mL) and then the mixture was stirred with heating for 20 hours. After the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. It was washed with ethyl acetate and dried to give Compound 1 (4.2 g, 14.22 mmol, 71.10%). [Preparation Example 2] Preparation of Compound 41
製備化合物2-1 將2,4-二溴-6-甲基-1，3,5-三畊（2〇运）溶於1'胛（200 mL)中，並於〇°c缓慢添加溴外苯基鎂（79. 〇8 mL，237. 25 mm〇 1，3. 0M於乙醚中）。5小時後’緩慢添加蒸傑水。以 EA萃取並以蒸餾水洗滌之後，萃取液以硫酸鎂乾燥並於減 壓下蒸餾。使用EA及曱醇再結晶，獲得化合物2-1(16 g， 64. 70 则1〇1，81. 90%)。 製備化合物2_2 參照 Journal of organic chemistry vol, 29，pages 678~681，1963，使用化合物2-1獲得化合物2-2(12. 6 g， 26 94942 201111471 45. 60 mmol, 70. 5%)。 製備化合物2-3 參照 Journal of organic chemistry vol. 29, pages 678-681，1963，使用化合物2-2獲得化合物2-3(6.7 g, 25. 60 mmol, 56. 3%)。 製備化合物41 將化合物 2-3(4. 18 g，20.0 mmol)及苯曱醛（2.3 g， 22. 0 mmol)溶於硝基苯（50 mL)中，然後加熱攪拌該混合物 20小時。將反應溫度降至室溫後，過濾所產生的黃色固體。 以乙酸乙酯洗務並乾燥，獲得化合物41 (4. 8 g，10. 66 mmol, 53. 3%)。 [製備例3]製備化合物86Preparation of compound 2-1 2,4-dibromo-6-methyl-1,3,5-trin (2 〇) was dissolved in 1' 胛 (200 mL), and bromine was slowly added at 〇 °c Phenyl magnesium (79. 〇 8 mL, 237.25 mm 〇1, 3.0 M in diethyl ether). After 5 hours, slowly add steamed water. After extracting with EA and washing with distilled water, the extract was dried over magnesium sulfate and distilled under reduced pressure. Recrystallization from EA and decyl alcohol gave Compound 2-1 (16 g, 64.70, 1:1, 81.90%). Preparation of Compound 2-2 Referring to Journal of organic chemistry vol, 29, pages 678-681, 1963, Compound 2-2 (12. 6 g, 26 94942 201111471 45. 60 mmol, 70.5%) was obtained using Compound 2-1. Preparation of Compound 2-3 Compound 2-3 (6.7 g, 25.60 mmol, 56.3%) was obtained using Compound 2-2, with reference to </ RTI> </ RTI> </ RTI> <RTIgt; Preparation of Compound 41 Compound 2-3 (4. 18 g, 20.0 mmol) and phenylfurfural (2.3 g, 22.0 mmol) were dissolved in nitrobenzene (50 mL), and the mixture was stirred for 20 hr. After the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. It was washed with ethyl acetate and dried to give Compound 41 (4. 8 g, 10.66 mmol, 53.3%). [Preparation Example 3] Preparation of Compound 86
OH H邮厂 3-1 製備化合物3-1 混合 2-胺基-5-溴苯甲酸（20 g, 92. 57 mmol)、1，2-二胺基苯（10 g，92. 57 mmol)及多填酸（polyphosphoric acid)(100 mL)，於250°C攪拌該混合物5小時。冷卻至 100°C並缓慢添加蒸餾水之後，於減壓下過濾所產生的固 體。將NaOH水溶液與所產生的固體一起攪拌。當所得混合 物中和時，於減壓下過濾，再以曱醇再結晶，獲得化合物 3-1(11 g，38. 17 mmol，41. 24%)。 27 94942 201111471 製備化合物3-2 將化合物 3-1(4. 18 g, 20.0 mmol)及苯甲醛（2.3 g， 22.0 mmol)溶於梢基苯（50 mL)之後，加熱擾拌該混合物 20小時。將反應溫度降至室溫之後，過濾所產生的黃色固 體。以乙酸乙酯洗滌並乾燥，獲得化合物3-2(4. 3 g，11.49 mmol, 57. 0%)。 製備化合物86 將化合物 3-2(4 g，10. 68 mmol)、°卡°坐（1. 78 g，10. 68 mmol)、Pd(0ac)2(0. 11 g，0. 53 mmol)、P(t-bu)3(0. 13 mL， 1. 06 mmol，50%於曱苯中）、Na0t-bu(3. 08 g，32. 06 mmol) 及甲苯（100 mL)於回流下混合。4小時後，將反應溫度降 至室溫並缓慢添加蒸餾水。以EA萃取並以硫酸鎂乾燥之 後，於藏壓下蒸餾，再經管柱分離，獲得化合物86(2. 6 g， 5. 64 mmol, 52. 86%) ° [製備例4]製備化合物90OH H Post 3-1 Preparation of Compound 3-1 Mixed 2-Amino-5-bromobenzoic acid (20 g, 92.57 mmol), 1,2-diaminobenzene (10 g, 92.57 mmol) And polyphosphoric acid (100 mL), and the mixture was stirred at 250 ° C for 5 hours. After cooling to 100 ° C and slowly adding distilled water, the resulting solid was filtered under reduced pressure. The aqueous NaOH solution was stirred with the solid produced. When the mixture was neutralized, it was filtered under reduced pressure and then crystallised from EtOAc to afford Compound 3-1 (11 g, 38.17 mmol, 41.24%). 27 94942 201111471 Preparation of compound 3-2 After compound 3-1 (4. 18 g, 20.0 mmol) and benzaldehyde (2.3 g, 22.0 mmol) were dissolved in benzene (50 mL), the mixture was stirred and heated for 20 hours. . After the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. It was washed with ethyl acetate and dried to give Compound 3-2 (4.3 g, 11.49 mmol, 57.0%). Preparation of compound 86 Compound 3-2 (4 g, 10.68 mmol), EtOAc (1. 78 g, 10.68 mmol), Pd (0 s) 2 (0. 11 g, 0. 53 mmol) , P(t-bu)3 (0. 13 mL, 1. 06 mmol, 50% in toluene), Na0t-bu (3.08 g, 32.06 mmol) and toluene (100 mL) under reflux mixing. After 4 hours, the reaction temperature was lowered to room temperature and distilled water was slowly added. After extracting with EA and drying over magnesium sulfate, the mixture was evaporated under reduced pressure and then purified by column to afford compound 86 (2.6 g, 5.64 mmol, 52.86%) [Preparation 4]
製備化合物4-1 混合2-胺基-4, 5-二溴苯曱酸（20 g，92.57 mmol)、 1，2-二胺基苯（10 g，92. 57 mmol)及多磷酸（100 mL)，並 於250°C攪拌5小時。冷卻至100°C之後，緩慢添加蒸餾水， 於減壓下過濾所產生的固體。將NaOH水溶液與固體一起攪 拌。當所得混合物中和時，於減壓下過濾，再以甲醇再結 28 94942 201111471 晶，獲得化合物 4-1(17. 2 g，46. 86 mmol, 50. 62%)。 製備化合物4-2 將化合物 4-1(4.18 g，20.0 mmol)及苯甲醛（2.3 g， 22.0 mmol)溶於硝基苯（50 mL)之後，加熱攪拌該混合物 2 0小時。當反應溫度降至室溫時，過滤所產生的黃色固 體。以乙酸乙酯洗滌並乾燥，獲得化合物4-2(4. 7 g，10. π mmol， 51.65%)。 製備化合物90 將化合物4-2(4 g，8.82 mmol)、苯基爛酸（3.22 g， 26. 48 mmol)、Pd(PPh3)4(0. 5 g，〇· 44 mmol)、2M K2C〇3(l5 mL)、甲苯（100 mL)及乙醇（50 mL)混合並於回流下授拌。 10小時後’將反應溫度降至室溫並緩慢添加蒸餾水。以EA 萃取並以硫酸鎂乾燥之後’於減壓下蒸餾，再經管柱分離， 獲得化合物 90(2· 3 g，5.13 mmol，58.26°/。）。 [製備例5]製備化合物97Preparation of Compound 4-1 Mixed 2-Amino-4,5-dibromobenzoic acid (20 g, 92.57 mmol), 1,2-diaminobenzene (10 g, 92.57 mmol) and polyphosphoric acid (100) (mL) and stirred at 250 ° C for 5 hours. After cooling to 100 ° C, distilled water was slowly added, and the resulting solid was filtered under reduced pressure. The aqueous NaOH solution was stirred with the solid. When the mixture was neutralized, it was filtered under reduced pressure, and then recrystallized from methanol to </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; Preparation of Compound 4-2 After dissolving Compound 4-1 (4.18 g, 20.0 mmol) and benzaldehyde (2.3 g, 22.0 mmol) in nitrobenzene (50 mL), the mixture was stirred for 20 hours. When the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. It was washed with ethyl acetate and dried to give Compound 4-2 (4. 7 g, 10. π mmol, 51.65%). Preparation of compound 90 Compound 4-2 (4 g, 8.82 mmol), phenyl rotten acid (3.22 g, 26.48 mmol), Pd(PPh3)4 (0.5 g, 〇· 44 mmol), 2M K2C〇 Mix 3 (l5 mL), toluene (100 mL) and ethanol (50 mL) and mix under reflux. After 10 hours, the reaction temperature was lowered to room temperature and distilled water was slowly added. After extracting with EA and drying over magnesium sulfate, it was distilled under reduced pressure and then separated by column to give compound 90 (2.3 g, 5.13 mmol, 58.26 ° /.). [Preparation Example 5] Preparation of Compound 97
製備化合物5-1 混合2-胺基-3, 5-二溴笨曱酸（20 g，92. 57 mmol)、 1’2-一胺基苯（l〇 g，92. 57 mmol)及多罐酸（100 mL)，並 於250°C攪拌5小時。冷卻至loot後，緩慢添加蒸餾水， 於減壓下過濾所產生的固體。將Na0H水溶液與固體一起攪 29 94942 201111471 拌。當所得混合物中和時，於減壓下過濾，再以甲醇再結 晶，獲得化合物 5-1(13. 5 g，36. 78 mmol，39.72%)。 製備化合物5-2 將化合物 5-1(4.18 g，20.0 mmol)及苯曱醛（2.3 g， 22. 0 mmol)溶於硝基苯（50 mL)之後，加熱攪拌該混合物 20小時。當反應温度降至室溫時，過濾所產生的黃色固 體。以乙酸乙酯洗滌並乾燥，獲得化合物5-2(4. 5 g，9. 93 mmol, 49.45%)。 製備化合物97 將化合物 5-2(4 g，10. 68 mmol )、坐（1. 78 g，10. 68 mmol)、Pd(0ac)2(0. 11 g，0. 53 mmol)、P(t-bu)3(0. 13 mL， 1. 06 mmol，50%於甲笨中）、Na0t-bu(3. 08 g，32. 06 mmol) 及曱苯（100 mL)混合並於回流下攪拌。4小時後，將反應 溫度降至室溫並緩慢添加蒸餾水。以EA萃取並以硫酸鎂乾 燥之後，於減壓下蒸餾，再經管柱分離，獲得化合物97(3. 2 g，5. 11 mmol，47. 9%)。 [製備例6]製備化合物101Preparation of compound 5-1 with 2-amino-3,5-dibromoindole (20 g, 92.57 mmol), 1'2-monoaminobenzene (10 g, 92.57 mmol) and more Pot acid (100 mL) and stir at 250 ° C for 5 hours. After cooling to the loot, distilled water was slowly added, and the resulting solid was filtered under reduced pressure. Mix the aqueous Na0H solution with the solid 29 94942 201111471. When the mixture was neutralized, it was filtered under reduced pressure and then recrystallized from methanol to give Compound 5-1 (13.5 g, 36.78 mmol, 39.72%). Preparation of Compound 5-2 After compound 5-1 (4.18 g, 20.0 mmol) and phenylfurfural (2.3 g, 22.0 mmol) were dissolved in nitrobenzene (50 mL), the mixture was stirred for 20 hr. When the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. It was washed with ethyl acetate and dried to give Compound 5-2 (4.5 g, 9.93 mmol, 49.45%). Preparation of Compound 97 Compound 5-2 (4 g, 10.68 mmol), sat. (1. 78 g, 10.68 mmol), Pd (0 ac) 2 (0. 11 g, 0.25 mmol), P ( T-bu)3 (0. 13 mL, 1. 06 mmol, 50% in a stupid), Na0t-bu (3.08 g, 32.06 mmol) and terpene (100 mL) were mixed and refluxed Stir. After 4 hours, the reaction temperature was lowered to room temperature and distilled water was slowly added. After extraction with EA and dried over magnesium sulfate, EtOAc (EtOAc) [Preparation Example 6] Preparation of Compound 101
製備化合物6-1 參照 Journal of organic chemistry vol. 29, pages 678-681, 1963,使用 5-氣-2-曱基嘧啶（20 g, 155. 57 mmol) 30 94942 201111471 獲得化合物 6-2(17.8 g，112. 97 mmol，72. 6%)。 製備化合物6-2 參照 Journal of organic chemistry vol· 29，pages 678-681，1963，使用化合物6-1獲得化合物6-2(8. 9 g， 62. 44 mmol，55. 28%)。 製備化合物6-3 將化合物 6-2(4. 18 g，20.0 mmol)及苯甲醛（2.3 g, 22.0 mmol)溶於硝基苯（50 mL)之後，加熱攪拌該混合物 20小時。當反應溫度降至室溫時’過濾所產生的黃色固 體。以乙酸乙酯洗滌並乾燥，獲得化合物6-3(3. 7 g，9.69 mmol, 48. 68%)。 製備化合物101 將化合物 6-3(5 g，13. 09 mmol)、2, 6-二笨基吼咬一 爛酸（3· 6 g，13. 09 mmol)、Pd(PPh3)4(0. 7 g，〇· 65 mm〇1)、 2M K2C〇3(20 mL)、曱苯（100 mL)及乙醇（40 mL)混合並於 回流下攪拌。12小時後，將反應溫度降至室溫並緩慢添加 蒸德水。以EA萃取並以硫酸鎂乾燥之後，於減壓下蒸館， 再經管柱分離，獲得化合物101(3. 5 g，6. 06 romoL 46·36%)。 [製備例7]製備化合物106Preparation of Compound 6-1 Referring to Journal of organic chemistry vol. 29, pages 678-681, 1963, using 5-ox-2-mercaptopyrimidine (20 g, 155.57 mmol) 30 94942 201111471 Obtained compound 6-2 (17.8 g, 112. 97 mmol, 72. 6%). Preparation of Compound 6-2 Compound 6-2 (8.9 g, 62.44 mmol, 55.28%) was obtained using Compound 6-1, </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; Preparation of compound 6-3 After dissolving compound 6-2 (4.18 g, 20.0 mmol) and benzaldehyde (2.3 g, 22.0 mmol) in nitrobenzene (50 mL), the mixture was stirred for 20 hr. The yellow solid produced was filtered when the reaction temperature was lowered to room temperature. It was washed with ethyl acetate and dried to give compound 6-3 (3.7 g, 9.69 mmol, 48.68%). Preparation of Compound 101 Compound 6-3 (5 g, 13.09 mmol), 2,6-diphenyl group, bituminic acid (3.6 g, 13.09 mmol), Pd(PPh3)4 (0. 7 g, 〇· 65 mm〇1), 2M K2C〇3 (20 mL), toluene (100 mL) and ethanol (40 mL) were mixed and stirred under reflux. After 12 hours, the reaction temperature was lowered to room temperature and steamed water was slowly added. After extracting with EA and drying over magnesium sulfate, the mixture was evaporated under reduced pressure, and then separated by a column to obtain Compound 101 (3.5 g, 6.06 romoL 46·36%). [Preparation Example 7] Preparation of Compound 106
將2-(2-胺基苯基）苯并咪嗤（4.18 g，20.0 mm〇i)及 94942 31 201111471 苯曱酸（2.3 g，22.0 mmol)溶於硝基苯（50 mL)之後，加熱 攪拌該混合物20小時。當反應溫度降至室溫時，過濾所產 生的黃色固體。以乙酸乙酯洗滌並乾燥，獲得化合物 106(4.2 g， 14.22 mmol， 71.10%)。 依據製備例1至7之製程製備有機電場發光化合物1 至110 ;表1顯示所製備之有機電場發光化合物的1H NMR 及MS/FAB數據。 表1 化合物 NMR(CDC13/ 200 MHz) MS/FAB 實測值 計算值 1 δ = 7.22(2Η, m), 7.41(lHf m), 7.5K2H, m), 7.58-7.59 (2H, m), 7.B3-7.84(2H, m), 8.16(lHf m), 8.28{2H, m), 8.5€(1H, m) 295.34 295.11 4 δ - 7.22-7.25(3H, m), 7.33(1H, m), 7.45-7.S(3H, m), 7.5B-7.59(4H/ m), 7.69(1H, m), 7.77(1H, m), 7.83-7.87(3Hf m), 7.94UH, m), 8·16(1Η, m}, 8·55~8·56(2Η, m). 460,53 460.17 7 δ « 7.22(2H, m), 7.42(1H, m) , 7.49{lH, m), 7.58-7.63(3Hr m), 7.72(1H, m), 7.83-7.84(2H, m), 7.92Ϊ1Η, m), 8.16(1H, m), 8·56(1Η, m), 8·97(1Η, m) 346.38 346,12 13 δ - 7.22 (2H, m), 7.4K2H, m) , 7.51-7.52(8H, m), 7.58-7.59(2H/ m), 7.66<3H, m), 7.83-7.84(2H, m), 8.16(1Η/ m), 8.56(1H, m) 447.53 447.17 19 δ = 7.22C2H, n〇, 7.37(6H, m), 7.46-7.59(13H, m), 7.83-7.89(4H, m), 8.16{1H, ra), 8.56(1H, m) 553.73 553.20 28 δ = 7.22{2H, m)# 7.53-7*59(4H, m) f 7.S3-7-84(2H, m), 8.01(lHf m), 8.16-8.18(2H, m), 8.56<1H# m) 352.41 352.0Θ 32 δ « 1.69{6Hf s), 6.94(lHf s), 7*22-7.3(6Hf m), 7.58-7.59(2H# m), 7.83-7.84(2H, m), B.16(XH, m), 8.56{1H, m) 361.44 361.16 32 94942 201111471 34 δ - 7(1H, m), 7.22-7.26(3H, m), 7.51(1H, m), 7.58-7.59(2H, m)f 7.83-7.88(4H, m), 8.16(1H, m), 8.5(1H, m), 8.56(1H, m), 8.81(2Hf m) 372.42 372.14 40 δ = 7.22(2Hf m), 7.47(2H, m), 7.54-7.59{6H, m), 7.83-7.84 (2H, m), 8.05(2H, m), 8.16(XH, m), 8.3(4H, m), 8.56(1H, m) 446.52 448.17 41 δ =* 7.22(2H, m), 7.4H2H, m), 7.51(4H, in), 7.58-7.59 (2H, m), 7.83-7.84(2H, m), 8.16{1H, m), 8.28(4H, mi, 8.56(1H, m) 450.49 450.16 45 δ = 7,22(2H, m), 7.41-7.59(10Hf m), 7.83-7.84(2H, m), 8.11-8.16(2H/ m), 8.3(2H, m) r B.56(2H, m) 448.52 448.17 48 δ = 7.22〜7.25(4H, m), 7.47 (2H, m), 7.54-7.59(6Hr m), 7.83-7.85{4H, m), B. 16-B.2(3H, m), 8.3(4K, m)f 8.5611H, m) 524.61 524.20. 54 δ - 7.22(2H, ra), 7.41(2H, m), 7.51-7.52(BH, m), 7.58-7,59(2H, m) f 7.66{3H, m), 7.83-7.84(2H, m) f 8.16(1H, m), 8.56(1H, m), 9.48(2H, m) 525.60 525.20 60 δ = 6.4K1H, m), 6.68(1H, m) # 7.1*7.11(2H, ra), 7.22(2H, m), 7.41*7.44(2Hf m), 7.51-7.52(4H, m) f 7.58-7.59(2H# ml, 7.83-7.84(2H, mj, 8.1€(1H, m), 8.56(1H, m), 9.48(2H, m) 488.54 488.17 6S δ = 7·22〜7.33(5Η, m), 7.5(1H, zn), 7.56-7.68 (5H, m), 7.79-7.84(4H, m), 7.94(1H, m), 8.12-8.16(2H, m), 8.55r8.56(2H, m) 460.53 460.17 67 δ « 7.22-7.33(7H, m), 7.5(1H, m), 7.58-7.68(5H, m), 7-79~7.85(6H, m), 7.94(1H, m), 812-8·16(2H, m), 8.55-8.56(2flf m) 536.62 536.20 70 δ » 7.22-7.25(6H, 'm), 7.41C2H, m) f .7.51-7.52(8H, m), 7.58-7.59(2H, ml, 7.83-7.85(6H, m)f 8.16(XHr ra), 8.56(1H, m) 602.69 602.22 72 δ 7.22-7.24(3H, m), 7,37(6H, π), 7·46(6Η, π), 7.55~7.59(6H, ra), 7·7(1Η, ir〇, 7.83-7.84(2H, m), 8.16(1H, m), 632.80 632.22 33 94942 201111471 8.24{2Hr m), 8.56(1H, m), 8.67(1H, m) 78 δ = 7.22-7.25(3H, m), 7,33(1H, zn), 7.58-7.68 (0Hf in), 7.79-7.84 (4H, m), 7.94(1Η, m)f 8.16(2H, m), 8.54-8.56(3Hf m) 510.59 510.18 84 δ » 7.22(2H, m), 7.41<4H, m), 7·51(8Η, ·7·58·7·59(2Η, m), 7.68~7.69(3H, m), 7·77~7·87(7Η, n〇,. B(1H, m), 8‘16-8·18(2Η, m), 8.28{8H, m), 0.56(lHf m) 923.03 922.33 86 δ « 7.22~7.33(5H, m), 7.41(1», m) f 7·卜7·51(3Η, m) f 7.59-7.63(2H, m), 7.94-7.98(2H, m), 8.06*8.16(3H, m) f 8.28{2H, m), 8.55-8.56(2H, m) 460.53 460.17 90 δ « 7.22(2H/ m), 7.4K3H, m), 7.51(6Hf m), 7.59{lHf m) r 7.79(4H, m)F 8.12(1H, s), 8.28(2^ in), 8.29(1H, s), B.56(lHf m) 447.53 447.17 97 δ « 7.22-7.33Ϊ8Η, m), 7.41(lHf m》，7.5-7.51(4H, m), 7.59-7.63(3Η, m), 7.94(2H, m), 8.05-8.12(4^ ια), 8.2Θ(2Η, m), 8.55-6.56(3H, m) 62S.72 625.23 ioo δ = 7.22(2H, m), 7.41{2H, m), 7.51-7.52(8H, m), 7.59(lHf m), 7.66-7.67(5Hf m), 7.84(lHf m), 8.01(lHf ra), 8.16{2H, m), 8.56{1H, m), 9.48(2^ m) 575.66 575.21 104 δ » 7.22(2H# m), 7.39-7.41 (5Hf m), 7.5K4H, m), 7.59(1H, m), 7.9K3H, m), 8.28-8.3K6H, xn> r 8.56(1H, m), 9.48(2Hf m) 628.68 628.21 105 δ - 7.22(2Hf m), 7.28(1H/ m) r 7.41{2H, m), 7.5K4H, m), 7.59(1H, m)t 7.67(1H, m), 8.28(4H/ m), 8.56(1H# m), 8.63(2H, m), 9.48{2R, m) 632.64 632.19 106 6 = 7.22-7.25(8H, m), 7.58*7.59(4Hf m) ,· 7.83*7.85(8H, m), 8.16(2Hr m), 8.56(2Hr m) 588.66 588.21 107 δ * 7.22~7.25(8H, m), 7.59(2H/ m), 7.67{4H, m)f 7.83-7.85C6H, m), 8.16(4H, m), 8.54-8.56[4Hf m) 688.70 688.24 108 δ « 7.22-7.25(8Hf m), 7.4X{4fif m), 7.5K8H, m), 7.59{2H, m) f 7.79-7.85(12H/ m), 8.12(2H, s), 8.29(2H, s), B.56(2H, m) 893.04 892.33 109 δ 7.22(6H, m), 7·5Β~7·59(6Η, m) r 7.66(3H, in)/ 7.83·7·84(6Η, m), 8·16(3Η, m), 8·56(3Η, m) 729.79 729.24 110 δ = 1.72(6H, B)f 7.22(4H, m), 7.58-7.63 (6H, m), 7.77Ϊ2Η, ία), 7.83-7.84(4^ m)f 7.93(2H, m), 8.16(2H, ra), 8.56(2H# m) 628.72 628.24 34 94942 201111471 [實施例1 ]使用本發明之有機電場發光化合物之0LED裝 置的製造 使用本發明之電場發光材料製造0LED襞置。 首先，使用超音波依序以三氯乙烯、丙酮、乙醇及蒸 顧水清洗由0LED用玻璃（由Samsung Corn i ng製造）所製得 之透明電極ΙΤ0薄膜（15 Ω/口），並儲存於異丙醇中備用。 然後’將ΙΤ0基板裝配於真空氣相沈積裝置之基板夾 中’並將4,4’，4” -參（Ν，Ν-(2-萘基）-苯基胺基）三苯胺 (2-ΤΝΑΤΑ)置於該真空氣相沈積裝置之一小室中，接著使該 腔室通風以達到1〇_6托（t〇rr)真空。隨後，對該小室施加 電流以蒸發2-TNATA，從而在該IT0基板上形成厚度為6〇 奈米（nm)之電洞注入層。 接著，將N，N’ _雙（α-萘基）-N，N’ _二苯基-4,4，_ 二胺（NPB)置於該真空氣相沈積裝置之另一小室中，對該小 室施加電流以蒸發NPB，從而於該電洞注人層上形成厚度 為20 nm之電洞傳輸層。 又 形成電洞注入層及電洞傳輸層之後，以下述方式於 上形成電場發光層。將化合物41置於該真空氣相沈積裝 之-小至中作為主體’並將具有下列結構之化合物卜(卯 置於f一小室中作爲摻雜劑。以不同速度蒸發該兩種 料伙而以4至1〇重量％於電洞傳輸層上氣相沈積厚产 30 nm之電場發光層。 & 94942 35 2011114712-(2-Aminophenyl)benzoimin (4.18 g, 20.0 mm 〇i) and 94942 31 201111471 benzoic acid (2.3 g, 22.0 mmol) were dissolved in nitrobenzene (50 mL) and heated The mixture was stirred for 20 hours. When the reaction temperature was lowered to room temperature, the resulting yellow solid was filtered. Washed with ethyl acetate and dried to give compound 106 (4.2 g, 14.22 mmol, 71.10%). Organic electroluminescent compounds 1 to 110 were prepared according to the procedures of Preparations 1 to 7; Table 1 shows the 1H NMR and MS/FAB data of the prepared organic electroluminescent compound. Table 1 Compound NMR (CDC13/200 MHz) MS/FAB Measured value 1 δ = 7.22 (2 Η, m), 7.41 (lHf m), 7.5 K2H, m), 7.58-7.59 (2H, m), 7. B3-7.84(2H, m), 8.16(lHf m), 8.28{2H, m), 8.5€(1H, m) 295.34 295.11 4 δ - 7.22-7.25(3H, m), 7.33(1H, m), 7.45-7.S(3H, m), 7.5B-7.59(4H/m), 7.69(1H, m), 7.77(1H, m), 7.83-7.87(3Hf m), 7.94UH, m), 8 ·16(1Η, m}, 8·55~8·56(2Η, m). 460,53 460.17 7 δ « 7.22(2H, m), 7.42(1H, m) , 7.49{lH, m), 7.58 -7.63(3Hr m), 7.72(1H, m), 7.83-7.84(2H, m), 7.92Ϊ1Η, m), 8.16(1H, m), 8·56(1Η, m), 8·97(1Η , m) 346.38 346,12 13 δ - 7.22 (2H, m), 7.4K2H, m), 7.51-7.52 (8H, m), 7.58-7.59 (2H/m), 7.66 <3H, m), 7.83 -7.84(2H, m), 8.16(1Η/ m), 8.56(1H, m) 447.53 447.17 19 δ = 7.22C2H, n〇, 7.37(6H, m), 7.46-7.59(13H, m), 7.83- 7.89(4H, m), 8.16{1H, ra), 8.56(1H, m) 553.73 553.20 28 δ = 7.22{2H, m)# 7.53-7*59(4H, m) f 7.S3-7-84 (2H, m), 8.01(lHf m), 8.16-8.18(2H, m), 8.56<1H# m) 352.41 352.0Θ 32 δ « 1.69{6Hf s), 6.94(lHf s), 7*22- 7.3 (6Hf m), 7.58-7.59 (2H# m), 7.83-7.84(2H, m), B.16(XH, m), 8.56{1H, m) 361.44 361.16 32 94942 201111471 34 δ - 7(1H, m), 7.22-7.26(3H, m), 7.51( 1H, m), 7.58-7.59(2H, m)f 7.83-7.88(4H, m), 8.16(1H, m), 8.5(1H, m), 8.56(1H, m), 8.81(2Hf m) 372.42 372.14 40 δ = 7.22(2Hf m), 7.47(2H, m), 7.54-7.59{6H, m), 7.83-7.84 (2H, m), 8.05(2H, m), 8.16(XH, m), 8.3 (4H, m), 8.56(1H, m) 446.52 448.17 41 δ =* 7.22(2H, m), 7.4H2H, m), 7.51(4H, in), 7.58-7.59 (2H, m), 7.83-7.84 (2H, m), 8.16{1H, m), 8.28(4H, mi, 8.56(1H, m) 450.49 450.16 45 δ = 7,22(2H, m), 7.41-7.59(10Hf m), 7.83-7.84 (2H, m), 8.11-8.16(2H/m), 8.3(2H, m) r B.56(2H, m) 448.52 448.17 48 δ = 7.22~7.25(4H, m), 7.47 (2H, m) , 7.54-7.59(6Hr m), 7.83-7.85{4H, m), B. 16-B.2(3H, m), 8.3(4K, m)f 8.5611H, m) 524.61 524.20. 54 δ - 7.22 (2H, ra), 7.41(2H, m), 7.51-7.52(BH, m), 7.58-7,59(2H, m) f 7.66{3H, m), 7.83-7.84(2H, m) f 8.16 (1H, m), 8.56(1H, m), 9.48(2H, m) 525.60 525.20 60 δ = 6.4K1H, m), 6.68(1H, m) # 7.1*7.11(2H, ra), 7.22(2H, m), 7.41*7.44(2Hf m), 7.51-7. 52(4H, m) f 7.58-7.59(2H# ml, 7.83-7.84(2H, mj, 8.1€(1H, m), 8.56(1H, m), 9.48(2H, m) 488.54 488.17 6S δ = 7 ·22~7.33(5Η, m), 7.5(1H, zn), 7.56-7.68 (5H, m), 7.79-7.84(4H, m), 7.94(1H, m), 8.12-8.16(2H, m) , 8.55r8.56(2H, m) 460.53 460.17 67 δ « 7.22-7.33(7H, m), 7.5(1H, m), 7.58-7.68(5H, m), 7-79~7.85(6H, m) , 7.94(1H, m), 812-8·16(2H, m), 8.55-8.56(2flf m) 536.62 536.20 70 δ » 7.22-7.25(6H, 'm), 7.41C2H, m) f .7.51- 7.52(8H, m), 7.58-7.59 (2H, ml, 7.83-7.85(6H, m)f 8.16(XHr ra), 8.56(1H, m) 602.69 602.22 72 δ 7.22-7.24(3H, m), 7 ,37(6H, π), 7·46(6Η, π), 7.55~7.59(6H, ra), 7·7(1Η, ir〇, 7.83-7.84(2H, m), 8.16(1H, m) , 632.80 632.22 33 94942 201111471 8.24{2Hr m), 8.56(1H, m), 8.67(1H, m) 78 δ = 7.22-7.25(3H, m), 7,33(1H, zn), 7.58-7.68 ( 0Hf in), 7.79-7.84 (4H, m), 7.94(1Η, m)f 8.16(2H, m), 8.54-8.56(3Hf m) 510.59 510.18 84 δ » 7.22(2H, m), 7.41<4H , m), 7·51 (8Η, ·7·58·7·59(2Η, m), 7.68~7.69(3H, m), 7·77~7·87(7Η, n〇,. B(1H , m), 8'16-8·18(2Η, m ), 8.28{8H, m), 0.56(lHf m) 923.03 922.33 86 δ « 7.22~7.33(5H, m), 7.41(1», m) f 7·卜7·51(3Η, m) f 7.59- 7.63(2H, m), 7.94-7.98(2H, m), 8.06*8.16(3H, m) f 8.28{2H, m), 8.55-8.56(2H, m) 460.53 460.17 90 δ « 7.22(2H/ m ), 7.4K3H, m), 7.51(6Hf m), 7.59{lHf m) r 7.79(4H, m)F 8.12(1H, s), 8.28(2^ in), 8.29(1H, s), B. 56(lHf m) 447.53 447.17 97 δ « 7.22-7.33Ϊ8Η, m), 7.41(lHf m),7.5-7.51(4H, m), 7.59-7.63(3Η, m), 7.94(2H, m), 8.05 -8.12(4^ ια), 8.2Θ(2Η, m), 8.55-6.56(3H, m) 62S.72 625.23 ioo δ = 7.22(2H, m), 7.41{2H, m), 7.51-7.52(8H , m), 7.59(lHf m), 7.66-7.67(5Hf m), 7.84(lHf m), 8.01(lHf ra), 8.16{2H, m), 8.56{1H, m), 9.48(2^ m) 575.66 575.21 104 δ » 7.22(2H# m), 7.39-7.41 (5Hf m), 7.5K4H, m), 7.59(1H, m), 7.9K3H, m), 8.28-8.3K6H, xn> r 8.56(1H , m), 9.48(2Hf m) 628.68 628.21 105 δ - 7.22(2Hf m), 7.28(1H/ m) r 7.41{2H, m), 7.5K4H, m), 7.59(1H, m)t 7.67(1H , m), 8.28(4H/m), 8.56(1H# m), 8.63(2H, m), 9.48{2R, m) 632.64 632.19 106 6 = 7.22-7.25(8H, m), 7.58*7.59 (4Hf m) ,····································· , m)f 7.83-7.85C6H, m), 8.16(4H, m), 8.54-8.56[4Hf m) 688.70 688.24 108 δ « 7.22-7.25(8Hf m), 7.4X{4fif m), 7.5K8H, m ), 7.59{2H, m) f 7.79-7.85(12H/m), 8.12(2H, s), 8.29(2H, s), B.56(2H, m) 893.04 892.33 109 δ 7.22(6H, m) , 7·5Β~7·59(6Η, m) r 7.66(3H, in)/ 7.83·7·84(6Η, m), 8·16(3Η, m), 8·56(3Η, m) 729.79 729.24 110 δ = 1.72(6H, B)f 7.22(4H, m), 7.58-7.63 (6H, m), 7.77Ϊ2Η, ία), 7.83-7.84(4^ m)f 7.93(2H, m), 8.16 (2H, ra), 8.56 (2H# m) 628.72 628.24 34 94942 201111471 [Example 1] Manufacture of an OLED device using the organic electroluminescent compound of the present invention An OLED device was produced using the electroluminescent material of the present invention. First, a transparent electrode ΙΤ0 film (15 Ω/□) made of OLED glass (manufactured by Samsung Corn ng) was washed with trichloroethylene, acetone, ethanol, and steamed water in order, and stored in Isopropyl alcohol is reserved. Then 'assemble the ΙΤ0 substrate in the substrate holder of the vacuum vapor deposition apparatus' and 4,4',4"-parameter (Ν,Ν-(2-naphthyl)-phenylamino)triphenylamine (2- ΤΝΑΤΑ) is placed in a chamber of the vacuum vapor deposition apparatus, and then the chamber is ventilated to reach a vacuum of 1 〇 6 Torr, and then a current is applied to the chamber to evaporate 2-TNATA, thereby A hole injection layer having a thickness of 6 nanometers (nm) is formed on the IT0 substrate. Next, N, N' _ bis (α-naphthyl)-N, N' _ diphenyl-4, 4, _ A diamine (NPB) is placed in another chamber of the vacuum vapor deposition apparatus, and a current is applied to the chamber to evaporate the NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. After the hole injection layer and the hole transport layer, an electric field light-emitting layer is formed thereon in the following manner. Compound 41 is placed in the vacuum vapor deposition apparatus as small as medium and will have a compound of the following structure (卯Placed in a small chamber as a dopant. The two materials are evaporated at different speeds and vapor deposited on the hole transport layer at 4 to 1% by weight. An electric field luminescent layer with a thickness of 30 nm. & 94942 35 201111471
化合物41 接著’於電場發光層上氣相沈積厚度為5 nm之雙(2_ 甲基-8-M基㈣基）（對笨基笨酚化（ΙΠ)⑽q)作為電 洞阻擋層’並氣相沈積厚度為20 nm之參（8—經基啥琳）銘 (III)(Alq)作為電子傳輪層。然後，氣相沈積厚度為丄⑽ 主2 nm之8-羥基喹啉鋰（lithium quin〇late，Uq)作為 電子注入層’接著再使用另—真空氣相沈積裝置形成厚度 為150 nm之銘（A1)陰極，進而製造出〇LEI)。 用於0LED之各化合物皆已於1〇_6 t〇rr經真空昇華而 純化。 [實施例2]使用本發明之有機電場發光化合物之〇LEd的 製造 除了不使用電洞阻擋層外，以實施例丨之相同方 造 0LED 〇 [實施例3]使用本發日月之有機電場發光化合物之〇L助的 製造 除了使用化合物78作為電場發光層之主體以及使用 (piqMr(acac)作為摻雜劑外，以實施例2之相同方 造 0LED。 、 36 94942 201111471Compound 41 then 'vapor-deposits the bis(2-methyl-8-Myl(tetra)yl) with a thickness of 5 nm on the electroluminescent layer (for the stupid base (10) q) as a hole barrier The phase-deposited thickness of 20 nm of ginseng (8-jing Jilin) Ming (III) (Alq) was used as the electron transfer layer. Then, a vapor deposition thickness of 丄(10) main 2 nm of lithium quinolate (Uq) is used as an electron injection layer, and then another vacuum-vapor deposition apparatus is used to form a thickness of 150 nm. A1) Cathode, which in turn produces 〇LEI). Each compound used for OLED was purified by vacuum sublimation at 1 〇 6 t rr. [Example 2] Production of 〇LEd using the organic electroluminescent compound of the present invention Manufactured in the same manner as in the Example 除了 except that the hole blocking layer was not used [Example 3] The organic electric field of the present day was used. The fabrication of the luminescent compound was carried out in the same manner as in Example 2 except that the compound 78 was used as the host of the electroluminescent layer and (piqMr(acac) was used as the dopant. 36 94942 201111471
[比較例1]使用傳統電場發光材料之0LED裝置的電場發 光特性 除了於該真空氣相沉積裝置之一小室中使用4,4’ -雙（咔唑-9-基）聯苯（CBP)取代本發明之化合物作為主體材 料外，以實施例1之相同方式製造0LED。 [比較例2]使用傳統電場發光材料之0LED裝置的電場發 光特性 除了於該真空氣相沉積裝置之一小室中使用4,4’ -雙（咔唑-9-基）聯苯（CBP)取代本發明之化合物作為主體材 料以及使用雙（2-曱基-8-羥基喹啉基）（對苯基苯酚）鋁 (III)(BAlq)作為電洞阻擋層外，以實施例3之相同方式製 造 0LED 。 於1，000燭光/平方米（cd/m2)測定實施例1至3及比 較例1與2所製造之包括本發明之有機電場發光化合物以 及傳統電場發光化合物的0LED裝置之發光效率。結果如表 2所示。 37 94942 201111471 表2 編號 主體 摻雜劑 電洞 阻擋層 驅動電壓 (V)@l〇〇〇 cd/m2 功率效率 (流明/瓦)@ 1000 cd/m2 顏色 實 施 例 1 1 7 Ir(ppy)3 BAlq 6.8 16.9 綠色 2 41 Ir(ppy)3 BAlq 6.6 17.5 綠色 3 50 Ir(ppy)3 BAlq 6.6 17.6 綠色 4 74 Ir(ppy)3 BAlq 6.9 16.7 綠色 5 89 Ir(ppy)3 BAlq 6.9 16.7 綠色 實 施 例 2 11 48 Ir(ppy)3 — 6.5 16.6 綠色 12 51 Ir(ppy)3 - 6.3 17.9 綠色 13 64 Ir(ppy)3 - 6.2 18.2 綠色 14 70 Ir(ppy)3 - 6.3 18.1 綠色 15 102 Ir(ppy)3 - 6.4 17.6 綠色 實 施 例 3 16 78 (piq)2lr(acac) - 6.2 5.0 紅色 17 81 (piqMr(acac) - 6.0 5.3 紅色 18 82 (piqMr(acac) — 6.1 5.1 紅色 19 100 (piq)2lr(acac) - 5.8 5.5 紅色 20 106 (piq)2lr(acac) - 5. 9 5.3 紅色 比j 交例 1 CBP Ir(ppy)3 BAlq 7.5 10.5 綠色 比較例 2 CBP (piq)2lr(acac) BAlq 7.5 '2.6 紅色 如表2所示，與傳統材料相比，本發明之有機電場發 光化合物具有優異的特性。此外，使用本發明之有機電場 發光化合物作為主體材料之裝置具有優異的電場發光特性 及降低的驅動電壓，從而使功率效率提高1. 7至3. 2流明/ 瓦（lm/W)並改善功率消耗。 【圖式簡單說明】無 【主要元件符號說明】無 38 94942[Comparative Example 1] The electric field luminescence characteristic of an OLED device using a conventional electroluminescence material was replaced by 4,4'-bis(carbazol-9-yl)biphenyl (CBP) in one of the chambers of the vacuum vapor deposition apparatus. An OLED was produced in the same manner as in Example 1 except that the compound of the present invention was used as a host material. [Comparative Example 2] Electric field luminescence characteristics of an OLED device using a conventional electroluminescence material were replaced by 4,4'-bis(carbazol-9-yl)biphenyl (CBP) in a chamber of the vacuum vapor deposition apparatus. In the same manner as in Example 3, the compound of the present invention was used as a host material and bis(2-mercapto-8-hydroxyquinolyl)(p-phenylphenol)aluminum (III) (BAlq) was used as a hole blocking layer. Manufacturing 0LED. The luminous efficiency of the OLED device comprising the organic electroluminescent compound of the present invention and the conventional electroluminescent compound produced in Examples 1 to 3 and Comparative Examples 1 and 2 was measured at 1,000 candles/m 2 (cd/m 2 ). The results are shown in Table 2. 37 94942 201111471 Table 2 Numbering body dopant hole barrier driving voltage (V)@l〇〇〇cd/m2 Power efficiency (lumens/watt) @ 1000 cd/m2 Color Example 1 1 7 Ir(ppy)3 BAlq 6.8 16.9 Green 2 41 Ir(ppy)3 BAlq 6.6 17.5 Green 3 50 Ir(ppy)3 BAlq 6.6 17.6 Green 4 74 Ir(ppy)3 BAlq 6.9 16.7 Green 5 89 Ir(ppy)3 BAlq 6.9 16.7 Green Example 2 11 48 Ir(ppy)3 — 6.5 16.6 Green 12 51 Ir(ppy)3 - 6.3 17.9 Green 13 64 Ir(ppy)3 - 6.2 18.2 Green 14 70 Ir(ppy)3 - 6.3 18.1 Green 15 102 Ir(ppy ) 3 - 6.4 17.6 Green Example 3 16 78 (piq)2lr(acac) - 6.2 5.0 Red 17 81 (piqMr(acac) - 6.0 5.3 Red 18 82 (piqMr(acac) — 6.1 5.1 Red 19 100 (piq)2lr (acac) - 5.8 5.5 Red 20 106 (piq)2lr(acac) - 5. 9 5.3 Red ratio j Example 1 CBP Ir(ppy)3 BAlq 7.5 10.5 Green Comparative Example 2 CBP (piq)2lr(acac) BAlq 7.5 '2.6 Red As shown in Table 2, the organic electroluminescent compound of the present invention has excellent characteristics as compared with the conventional material. Further, the organic electroluminescent compound of the present invention is used. The device of the host material has excellent electric field illuminating characteristics and a reduced driving voltage, thereby increasing power efficiency by 1. 7 to 3.2 lumens per watt (lm/W) and improving power consumption. [Simple description of the diagram] None [mainly Component Symbol Description] No 38 94942
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| US9972784B2 (en) | 2011-06-13 | 2018-05-15 | Lg Chem, Ltd. | Compounds and organic electronic device using same |
| DE112012007348B3 (en) * | 2011-07-22 | 2021-04-01 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, display device, lighting device, and electronic device |
| CN108299439B (en) | 2011-11-10 | 2021-02-09 | Udc 爱尔兰有限责任公司 | 4H-imidazo [1,2-a ] imidazoles for electronic applications |
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| CN103145625A (en) * | 2013-03-29 | 2013-06-12 | 吴江信凯医药科技有限公司 | Method for preparing 2-cyanopyrimidine |
| KR101427620B1 (en) * | 2013-05-14 | 2014-08-07 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR102079255B1 (en) | 2013-06-18 | 2020-02-20 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising same |
| CN105408333B (en) * | 2013-07-17 | 2018-10-16 | 喜星素材株式会社 | Nitrogenous polycyclic compound and use its organic luminescent device |
| KR101656942B1 (en) * | 2013-09-30 | 2016-09-12 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
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|---|---|
| WO2011010842A3 (en) | 2011-03-24 |
| KR20110008784A (en) | 2011-01-27 |
| WO2011010842A2 (en) | 2011-01-27 |
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