TW202309243A - Materials for organic electroluminescent devices - Google Patents

Materials for organic electroluminescent devices Download PDF

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TW202309243A
TW202309243A TW111113074A TW111113074A TW202309243A TW 202309243 A TW202309243 A TW 202309243A TW 111113074 A TW111113074 A TW 111113074A TW 111113074 A TW111113074 A TW 111113074A TW 202309243 A TW202309243 A TW 202309243A
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盧分 凌吉
米瑞姆 恩格爾
薩巴斯汀 史托茲
賽巴斯汀 梅爾
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德商麥克專利有限公司
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    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The present invention relates to a composition comprising a compound of formula (H1) and a compound of formula (H2). The present inven­tion furthermore relates to a formulation comprising a composition comprising a compound of formula (H1) and a formula (H2) and a solvent. Finally, the present invention relates to an electronic device comprising a such a composition.

Description

用於有機電致發光裝置之材料Materials for Organic Electroluminescent Devices

本發明關於一種包含式(H1)化合物和式(H2)化合物之組成物。本發明此外關於一種調配物，其包含一種包含式(H1)和式(H2)化合物之組成物及一種溶劑。最後，本發明關於一種包含該種組成物之電子裝置。The present invention relates to a composition comprising a compound of formula (H1) and a compound of formula (H2). The invention furthermore relates to a formulation comprising a composition comprising compounds of formula (H1) and formula (H2) and a solvent. Finally, the invention relates to an electronic device comprising such a composition.

用於電子裝置的功能性化合物之開發為目前深入研究的主題。特別地，目的為開發可用其達成改良電子裝置在一或多個相關特徵的性質(諸如，例如，裝置的功率效率和壽命以及發射光的色坐標)之化合物。 根據本發明，術語電子裝置尤其意指有機積體電路(OIC)、有機場效電晶體(OFET)、有機薄膜電晶體(OTFT)、有機發光電晶體(OLET)、有機太陽能電池(OSC)、有機光學檢測器、有機感光器(photoreceptor)、有機場淬滅裝置(OFQD)、有機發光電化學電池(OLEC)、有機雷射二極體(O-雷射)和有機電致發光裝置(OLED)。 特別感興趣的是提供使用於最後提及之稱為OLED的電子裝置之化合物。OLED的一般結構和功能原理為熟習該項技術者已知且描述於例如US 4539507中。 仍然需要關於OLED之性能數據的進一步改良，特別是鑑於廣泛商業用途，例如，用於顯示裝置或作為光源。就此而論，特別重要的是OLED的壽命、效率和操作電壓以及所達成的色值。特別地，在藍色發光OLED的情況下，關於裝置的效率、壽命和操作電壓之改良是有可能的。 達成該等改良的重要起點為發光體化合物的選擇及主體化合物的選擇。事實上，發光體化合物通常係與第二化合物組合用於發光層，該第二化合物係用作為基質化合物或主體化合物。發光體化合物在本文中意指在電子裝置操作期間發射光的化合物。主體化合物在此情況下意指以大於該發光體化合物的比例存在於混合物中之化合物。術語基質化合物和術語主體化合物可同義地使用。主體化合物較佳不發射光。即使多種不同的主體化合物存在於發光層的混合物中，彼等個別比例通常大於發光體化合物的比例，或若多種發光體化合物存在於發光層的混合物，則大於個別發光體化合物的比例。例如US 4769292中已描述關於螢光發射層中之該等實施態樣。 若多種化合物的混合物存在於發光層中，則發光體化合物通常是以較小量(即，以小於發光層的混合物中的其他化合物之比例)存在的組份。在此情況下，發光體化合物亦稱為摻雜劑。 從先前技術中已知的用於螢光發光體之主體化合物為多種化合物。發光層可包括一種主體化合物或更多種。包含萘并雙苯并呋喃基團之主體化合物已揭示於先前技術中(例如於WO 2020/089138中)。包含二苯并呋喃和蒽基團之主體化合物已揭示於先前技術中(例如於KR 10-2017-0096860和CN 109867646中)。 然而，仍然需要用於螢光發光體的其他主體材料或主體材料的組合，其可使用於OLED中並且導致在壽命、顏色發射和效率方面具有非常好的性質之OLED。更特別地，需要組合非常高的效率、非常好的壽命和非常好的熱穩定性之用於螢光發光體的主體材料或主體材料的組合。 此外，已知OLED可包含不同的層，其可在真空室中藉由氣相沈積施加或藉由從溶液處理。以氣相沈積為基礎之方法導致良好的結果，但該等方法複雜且昂貴。因此，也需要可從溶液容易且可靠地處理的包含OLED材料之組成物。更特別地，需要包含OLED材料之組成物，其當從調配物(更特別是從溶液如油墨)處理時在製造OLED期間可沉積成均勻之薄膜。在此情況下，該等材料在包含彼的溶液中應具有良好的溶解度，且包含OLED材料之沉積薄膜在導致移除溶劑的乾燥步驟後應儘可能的平滑。重要的是，沉積層形成平滑且均勻的薄膜，因為層厚度不均勻性造成不均勻的發光強度分佈，且膜厚度較薄的區域顯示增加的發光強度，而較厚的區域具有減少的發光強度，其導致OLED的品質下降。同時，包含從溶液處理的薄膜之OLED應呈現良好的性能，例如在壽命、操作電壓和效率方面。 此外仍然需要導致容易純化和容易處理之穩定的OLED材料之方法。需要藉由以可接受的純度和高產率提供OLED材料而在經濟和品質上令人感興趣之方法。 The development of functional compounds for use in electronic devices is currently the subject of intensive research. In particular, the aim is to develop compounds which can be achieved to improve the properties of electronic devices in one or more relevant features, such as, for example, the power efficiency and lifetime of the device and the color coordinates of the emitted light. According to the present invention, the term electronic device means especially organic integrated circuit (OIC), organic field effect transistor (OFET), organic thin film transistor (OTFT), organic light emitting transistor (OLET), organic solar cell (OSC), Organic optical detectors, organic photoreceptors (photoreceptors), organic field quenching devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs) ). Of particular interest is the provision of compounds for use in the last-mentioned electronic devices known as OLEDs. The general structure and functional principles of OLEDs are known to those skilled in the art and are described, for example, in US 4,539,507. Further refinement of the performance data on OLEDs is still needed, especially in view of widespread commercial use, eg for display devices or as light sources. Of particular importance in this connection are the lifetime, efficiency and operating voltage of the OLEDs as well as the color values achieved. Especially in the case of blue-emitting OLEDs, improvements are possible with regard to the efficiency, lifetime and operating voltage of the device. An important starting point for achieving these improvements is the selection of the emitter compound and the selection of the host compound. In fact, the emitter compound is usually used in the light-emitting layer in combination with a second compound which acts as matrix compound or host compound. An emitter compound here means a compound that emits light during operation of the electronic device. A host compound in this case means a compound which is present in the mixture in a larger proportion than the emitter compound. The term matrix compound and the term host compound may be used synonymously. The host compound preferably does not emit light. Even if a plurality of different host compounds are present in the mixture of the emitting layer, their individual proportions are generally greater than the proportions of the emitter compounds, or, if a plurality of emitter compounds are present in the mixture of the emitting layer, than the proportions of the individual emitter compounds. Such implementations in fluorescent emissive layers have been described, for example, in US 4769292. If a mixture of compounds is present in the emitting layer, the emitter compound is usually a component present in a minor amount, ie in a smaller proportion than the other compounds in the mixture of the emitting layer. In this case, the emitter compounds are also referred to as dopants. Host compounds for fluorescent emitters are known from the prior art in a wide variety of compounds. The light emitting layer may include one kind of host compound or more kinds. Host compounds comprising a naphthobisbenzofuran group have been disclosed in the prior art (eg in WO 2020/089138). Host compounds comprising dibenzofuran and anthracene groups have been disclosed in the prior art (eg in KR 10-2017-0096860 and CN 109867646). However, there is still a need for other host materials or combinations of host materials for fluorescent emitters which can be used in OLEDs and lead to OLEDs with very good properties in terms of lifetime, color emission and efficiency. More particularly, there is a need for host materials or combinations of host materials for fluorescent emitters that combine very high efficiency, very good lifetime and very good thermal stability. Furthermore, it is known that OLEDs can comprise different layers, which can be applied by vapor deposition in a vacuum chamber or by processing from solution. Methods based on vapor deposition lead to good results, but are complex and expensive. Accordingly, there is also a need for compositions comprising OLED materials that can be easily and reliably processed from solution. More particularly, there is a need for compositions comprising OLED materials that can be deposited as uniform thin films during the manufacture of OLEDs when processed from formulations, more particularly from solutions such as inks. In this case, the materials should have good solubility in the solutions containing them, and the deposited film containing the OLED material should be as smooth as possible after the drying step leading to the removal of the solvent. It is important that the deposited layer forms a smooth and uniform film because layer thickness inhomogeneity causes a non-uniform luminous intensity distribution, and regions with thinner film thicknesses show increased luminous intensity, while thicker regions have decreased luminous intensity , which leads to a decrease in the quality of the OLED. At the same time, OLEDs comprising thin films processed from solution should exhibit good properties, eg in terms of lifetime, operating voltage and efficiency. Furthermore there remains a need for methods leading to stable OLED materials that are easy to purify and easy to handle. There is a need for an economically and qualitatively interesting method by providing OLED materials with acceptable purity and high yield.

本發明因此係基於提供適合用於電子裝置(諸如OLED)，更特別是作為螢光發光體之基質組份的包含OLED材料之組成物的技術目標。本發明亦是基於提供特別適合於溶液處理的包含OLED材料之組成物的技術目標。本發明亦基於提供方法的技術目標。 在對使用於電子裝置之新穎組成物之研究中，目前已發現，如下所定義之包含式(H1)化合物和式(H2)化合物之組成物非常適合使用於電子裝置。特別地，彼等達成上述技術目標之一或多者，較佳為全部。 本申請案因此關於一種組成物，其包含式(H1)化合物和式(H2)化合物，

Figure 02_image001
Figure 02_image003
其中下列適用於所使用的符號和標號： E 1、E 2、E 3和E 4在每次出現時相同或不同地代表單鍵、-BR 0-、-C(R 0) 2-、-Si(R 0) 2-、-C(=O)-、-O-、 -S-、-S(=O)-、-SO 2-、-N(R 0)-或-P(R 0)-；其先決條件為，在包含E 1和E 3之環中，只有一個基團E 1或E 3可為單鍵及，在包含E 2和E 4之環中，只有一個基團E 2或E 4可為單鍵； E 5代表O或S； X 1至X 12在每次出現時相同或不同地代表C-R X、C-Ar X或N；其先決條件為至少一個選自X 1至X 12之基團代表基團C-Ar X及Ar X代表式(Ar X)之基團：
Figure 02_image005
其中虛線鍵表示至C-Ar X中之基團C的鍵結； Z 1至Z 8在每次出現時相同或不同地代表C-R Z、C-Ar Z或N；其先決條件為至少一個選自Z 1至Z 8之基團代表基團C-Ar Z及Ar Z代表式(Ar Z)之基團：
Figure 02_image007
其中虛線鍵表示至C-Ar Z中之基團C的鍵結； Ar 1在每次出現時相同或不同地為具有10至60個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R V取代； Ar 3在每次出現時相同或不同地為具有10至60個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R Y取代； Ar 2、Ar 4、Ar S在每次出現時相同或不同地為具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R取代； R V、R X、R Y、R Z在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R) 2、N(Ar) 2、NO 2、Si(R) 3、B(OR) 2、OSO 2R、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基，彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經RC=CR、C≡C、Si(R) 2、Ge(R) 2、Sn(R) 2、C=O、C=S、C=Se、P(=O)(R)、SO、SO 2、O、S或CONR置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換、具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代、或具有5至60個芳族環原子之芳氧基，其可經一或多個基團R取代； 其中二個基團R V、二個基團R X、二個基團R Y、二個基團R Z可一起形成脂族、芳族或雜芳族環系統，其可經一或多個基團R取代； R 0在每次出現時相同或不同地代表H、D、F、具有1至20個C原子之直鏈烷基、或具有3至20個C原子之支鏈或環狀烷基，彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經O或S置換及其中一或多個H原子可經D或F置換、或具有5至40個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代，其中二個相鄰基團R 0，可一起形成脂族或芳族環系統，其可經一或多個基團R取代； R 在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R’) 2、N(Ar) 2、NO 2、Si(R’) 3、B(OR’) 2、OSO 2R’、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基，彼等各自可經一或多個基團R’取代，其中在各情況下一或多個非相鄰的CH 2基團可經R’C=CR’、C≡C、Si(R’) 2、Ge(R’) 2、Sn(R’) 2、C=O、C=S、C=Se、P(=O)(R’)、SO、SO 2、O、S或CONR’置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換、具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R’取代、或具有5至60個芳族環原子之芳氧基，其可經一或多個基團R’取代；其中二個基團R可一起形成脂族或芳族環系統，其可經一或多個基團R’取代； Ar 在每次出現時相同或不同地為具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R’取代； R’ 在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CN、具有1至20個C原子之直鏈烷基、烷氧基或烷硫基或具有3至20個C原子之支鏈或環狀烷基、烷氧基、或烷硫基，其中在各情況下一或多個非相鄰的CH 2基團可經SO、SO 2、O、S置換及其中一或多個H原子可經D、F、Cl、Br或I置換、或具有5至24個芳族環原子之芳族或雜芳族環系統；及 p、s 在每次出現時相同或不同地為0或1，其中： 當p或s為0時，則對應Ar S不存在及基團Ar 1或Ar 3直接鍵結至C-Ar X或C-Ar Z中之C； q、t 在每次出現時相同或不同地為0、1或2，其中： 當q為0時，則Ar 4不存在；當t為0時，則Ar 2不存在； 當q為1或2時，則Ar 1係經一個基團或二個基團Ar 4取代； 當t為1或2時，則Ar 3係經一個基團或二個基團Ar 2取代。 此外，下列化學基團的定義適用於本申請案之目的： 芳基就本發明之意義而言包含6至60個芳族環原子，較佳6至40個芳族環原子，更佳6至20個芳族環原子；雜芳基就本發明之意義而言包含5至60個芳族環原子，較佳5至40個芳族環原子，更佳5至20個芳族環原子，其中至少一者為雜原子。雜原子較佳地係選自N、O和S。此表示基本定義。若在本發明說明中指示其他較佳選擇，例如有關所存在之芳族環原子或雜原子的數目，則這些適用。 芳基或雜芳基在此意指簡單芳族環，即苯，或簡單雜芳族環，例如吡啶、嘧啶或噻吩，或縮合(稠合(annellated))芳族或雜芳族多環，例如萘、菲、喹啉或咔唑。縮合(稠合)芳族或雜芳族多環就本申請案的意義而言由二或更多個彼此縮合之簡單芳族或雜芳族環組成。 在各情況下可經上述基團取代且可經由任何所要位置連接至芳族或雜芳族環系統之芳基或雜芳基特別意指衍生自下列之基團：苯、萘、蒽、菲、芘、二氫芘、
Figure 111113074-001
(chrysene)、苝、丙二烯合茀(fluoranthene)、苯并蒽、苯并菲、稠四苯、稠五苯、苯并芘、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻𠯤、啡㗁𠯤、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑(naphthimidazole)、菲并咪唑(phenanthrimidazole)、吡啶并咪唑(pyridimidazole)、吡𠯤并咪唑(pyrazinimidazole)、喹㗁啉并咪唑(quinoxalinimidazole)、㗁唑、苯并㗁唑、萘并㗁唑(naphthoxazole)、蒽并㗁唑(anthroxazole)、菲并㗁唑(phenanthroxazole)、異㗁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒𠯤、苯并嗒𠯤、嘧啶、苯并嘧啶、喹㗁啉、吡𠯤、啡𠯤、㖠啶、氮雜咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-㗁二唑、1,2,4-㗁二唑、1,2,5-㗁二唑、1,3,4-㗁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三𠯤、1,2,4-三𠯤、1,2,3-三𠯤、四唑、1,2,4,5-四𠯤、1,2,3,4-四𠯤、1,2,3,5-四𠯤、嘌呤、蝶啶、吲
Figure 111113074-002
及苯并噻二唑。 根據本發明之定義的芳氧基意指如上述所定義之芳基，其經由氧原子鍵結。類似定義適用於雜芳氧基。 芳族環系統就本發明之意義而言在環系統中包含6至60個C原子，較佳地6至40個C原子，更佳地6至20個C原子。雜芳族環系統就本發明之意義而言包含5至60個芳族環原子，較佳地5至40個芳族環原子，更佳地5至20個芳族環原子，其中至少一個為雜原子。雜原子較佳選自N、O及/或S。芳族或雜芳族環系統就本發明之意義而言意指不一定只包含芳基或雜芳基，而是其中此外多個芳基或雜芳基可藉由非芳族單元(較佳為少於10%之非H的原子)(諸如，例如sp 3-混成之C、Si、N或O原子、sp 2-混成之C或N原子或sp-混成之C原子)連接的系統。因此，例如，系統諸如9,9’-螺二茀、9,9’-二芳基茀、三芳基胺、二芳基醚、二苯乙烯、等等亦意欲為就本發明之意義而言的芳族環系統，如為其中二或多個芳基例如藉由直鏈或環狀烷基、烯基或炔基或藉由矽基連接之系統。此外，其中二或多個芳基或雜芳基係經由單鍵彼此連結之系統亦為就本發明之意義而言的芳族或雜芳族環系統，諸如，例如系統諸如聯苯、聯三苯或二苯基三𠯤。 在各情況下亦可經如上述所定義之基團取代且可經由任何所要位置連接至芳族或雜芳族基團之具有5-60個芳族環原子的芳族或雜芳族環系統特別意指衍生自下列之基團：苯、萘、蒽、苯并蒽、菲、苯并菲、芘、
Figure 111113074-001
(chrysene)、苝、丙二烯合茀(fluoranthene)、稠四苯、稠五苯、苯并芘、聯苯、伸聯苯(biphenylene)、聯三苯(terphenyl)、聯伸三苯(terphenylene)、聯四苯(quaterphenyl)、茀、螺二茀、二氫菲、二氫芘、四氫芘、順-或反-茚并茀、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻𠯤、啡㗁𠯤、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑(naphthimidazole)、菲并咪唑(phenanthrimidazole)、吡啶并咪唑(pyridimidazole)、吡𠯤并咪唑(pyrazinimidazole)、喹㗁啉并咪唑(quinoxalinimidazole)、㗁唑、苯并㗁唑、萘并㗁唑(naphthoxazole)、蒽并㗁唑(anthroxazole)、菲并㗁唑(phenanthroxazole)、異㗁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒𠯤、苯并嗒𠯤、嘧啶、苯并嘧啶、喹㗁啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜苝、吡𠯤、啡𠯤、啡㗁𠯤、啡噻𠯤、螢紅環(fluorubin)、㖠啶、氮雜咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-㗁二唑、1,2,4-㗁二唑、1,2,5-㗁二唑、1,3,4-㗁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三𠯤、1,2,4-三𠯤、1,2,3-三𠯤、四唑、1,2,4,5-四𠯤、1,2,3,4-四𠯤、1,2,3,5-四𠯤、嘌呤、喋啶、吲
Figure 111113074-002
和苯并噻二唑、或這些基團的組合。 就本發明之目的而言，具有1至40個C原子之直鏈烷基或具有3至40個C原子之支鏈或環狀烷基或具有2至40個C原子之烯基或炔基，其中，此外，個別H原子或CH 2基團可經在上述該等基團定義下之基團取代，較佳意指基團甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、2-甲基丁基、正戊基、二級戊基、環戊基、新戊基、正己基、環己基、新己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1至40個C原子之烷氧基或烷硫基較佳意指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、正戊氧基、二級戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基、三級丁硫基、正戊硫基、二級戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。 就本申請案之目的而言，二或更多個基團彼此可形成環之陳述特別意指：二個基團彼此以一化學鍵鍵聯。此以下列圖解說明：
Figure 02_image009
然而，此外，上述陳述也意指：在其中二基團之一表示氫的情況中，第二基團鍵結於氫原子所鍵結之位置，且形成環。此以下列圖解說明：
Figure 02_image011
當二個基團彼此形成環時，則較佳的是二個基團為相鄰的基團。相鄰基團就本發明之意義而言為鍵結至彼此直接連接的原子或鍵結至同一原子上的基團。 較佳地，基團Ar 1、Ar 3在每次出現時相同或不同地代表具有10至18個芳族環原子之縮合芳基。更佳地，基團Ar 1、Ar 3在每次出現時相同或不同地代表蒽、萘、菲、稠四苯、
Figure 111113074-001
(chrysene)、苯并蒽、苯并菲、芘、苝、聯伸三苯、苯并芘或丙二烯合茀(fluoranthene)，彼等各自可經一或多個基團R V(在Ar 1的情況)或經R Y(在Ar 3的情況)取代在任何自由位置。非常佳地，基團Ar 1、Ar 3代表蒽基團，其可經一或多個基團R V取代在Ar 1之任何自由位置或經一或多個基團R Y取代在Ar 3之任何自由位置。 適當基團Ar 1和Ar 3之實例為如下表中所表示的式(Ar1-1)至(Ar1-11)之基團：
Figure 02_image013
其中該等式(Ar-1)至(Ar-11)之基團可鍵結至相鄰的基團之任何位置且在Ar 1的情況下可經基團R V和在Ar 3的情況下可經R Y取代在各自由位置。 式(Ar1-1)至(Ar1-11)之基團中，式(Ar1-1)之基團為較佳。 非常適當的基團Ar 1和Ar 3之實例為如下表中所表示的式(Ar1-1-1)至(Ar1-12-1)之基團：
Figure 02_image015
其中 虛鍵表示至相鄰基團的鍵結；及其中式(Ar1-1-1)至(Ar1-12-1)之基團在Ar 1的情況可經基團R V取代在各自由位置，或在Ar 3的情況可經基團R Y取代在各自由位置，其中R V和R Y具有與上述相同的意義。 式(Ar1-1-1)至(Ar1-12-1)之基團中，式(Ar1-1-1)之基團為較佳。 較佳的是，在式(H1)化合物中，至少一個選自X 1至X 4之基團代表基團C-Ar X，其中Ar X代表如上定義的式(Ar X)之基團及基團X 5至X 12代表C-R X或N。 較佳地，式(H1)化合物係選自式(H1-A)至(H1-D)之化合物：
Figure 02_image017
Figure 02_image019
其中該等符號具有與上述相同的意義。 較佳地，E 1、E 2、E 3和E 4在每次出現時相同或不同地代表單鍵、-C(R 0) 2-、-Si(R 0) 2-、-O-、-S-或-N(R 0)。更佳地，一個選自E 1和E 3之基團代表單鍵及其他基團代表 -C(R 0) 2-、-Si(R 0) 2-、-O-、-S-或-N(R 0)及一個選自E 2和E 4之基團代表單鍵及其他基團代表-C(R 0) 2-、-Si(R 0) 2-、 -O-、-S-或-N(R 0)。 更佳地，式(H1)化合物係選自下列式之化合物：
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027
Figure 02_image029
Figure 02_image031
其中該等符號R X、Ar X具有與上述相同的意義及基團E 1、E 2、E 3和E 4在每次出現時相同或不同地代表-BR 0-、 -C(R 0) 2-、-Si(R 0) 2-、-C(=O)-、-O-、-S-、-S(=O)-、-SO 2-、-N(R 0)-或-P(R 0)-。 在式(H1-A-1)至(H1-D-4)之化合物中，式(H1-A-1)、(H1-B-1)、(H1-C-1)和(H1-D-1)之化合物為較佳。 較佳地，基團Ar X代表式(Ar X-1)之基團：
Figure 02_image033
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R V取代在各自由位置。 更佳地，基團Ar X代表下列式之一者的基團：
Figure 02_image035
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R V取代在各自由位置。 特佳地，式(H1)化合物係選自下列式之化合物：
Figure 02_image037
Figure 02_image039
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R V取代在各自由位置。 較佳地，R V、R X在每次出現時相同或不同地代表H、D、F、具有1至40個(較佳1至20個，更佳1至10個) C原子之直鏈烷基、烷氧基或烷硫基或具有3至40個(較佳3至20個，更佳3至10個)C原子之支鏈或環狀烷基、烷氧基或烷硫基(彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經RC=CR、C≡C、O或S置換及其中一或多個H原子可經D或F置換)、具有5至60個(較佳5至40個，更佳5至30個，特佳5至18個)芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)。更佳地，R V、R X在每次出現時相同或不同地代表H、D、F、具有1至20個(較佳1至10個，更佳1至6個)C原子之直鏈烷基或具有3至20個(較佳3至10個，更佳3至6個)C原子的支鏈或環狀烷基(彼等各自可經一或多個基團R取代)、具有5至40個(較佳5至30個，更佳5至18個)芳族環原子的芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)。更佳地，R X為H或D。更佳地，R V為H或D。 較佳的是，在式(H2)化合物中，一個選自Z 1至Z 4之基團代表基團C-Ar Z及一個選自Z 5至Z 8之基團代表基團C-Ar Z，其中Ar Z代表如上定義的式(Ar Z)之基團。 較佳地，化合物(H2)係選自下列式之化合物：
Figure 02_image041
Figure 02_image043
Figure 02_image045
其中該等符號具有與上述相同的意義。 式(H2-A)至(H2-J)化合物之中，式H2-A至H2-E、H2-H、H2-I之化合物為較佳。 較佳地，基團Ar Z代表式(Ar Z-1)之基團：
Figure 02_image047
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R Y取代在各自由位置。 較佳地，基團Ar Z代表下列式之一者的基團：
Figure 02_image049
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R Y取代在各自由位置。 更佳地，化合物(H2)係選自下列式之化合物：
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
Figure 02_image059
其中該等符號和標號具有與上述相同的意義及其中該蒽基團可經基團R Y取代在各自由位置。 式(H2-A-1)至(H2-J-2)化合物之中，式H2-A-1至H2-E-1、H2-H-1、H2-H2、H2-I2和H2-I-1 之化合物為較佳。 較佳地，R Y、R Z在每次出現時相同或不同地代表H、D、F、具有1至40個(較佳1至20個，更佳1至10個) C原子之直鏈烷基、烷氧基或烷硫基或具有3至40個(較佳3至20個，更佳3至10個) C原子之支鏈或環狀烷基、烷氧基或烷硫基(彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經RC=CR、C≡C、O或S置換及其中一或多個H原子可經D或F置換)、具有5至60個(較佳5至40個，更佳5至30個，特佳5至18個)芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)。更佳地，R Y、R Z在每次出現時相同或不同地代表H、D、F、具有1至20個(較佳1至10個，更佳1至6個) C原子之直鏈烷基或具有3至20個(較佳3至10個，更佳3至6個) C原子的支鏈或環狀烷基(彼等各自可經一或多個基團R取代)、具有5至40個(較佳5至30個，更佳5至18個)芳族環原子的芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)。更佳地，R Z代表H或D。更佳地，R Y代表H或D。 較佳地，基團Ar 2和Ar 4在每次出現時係相同或不同地選自具有5至30個(較佳5至25個)芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代。更佳地，基團Ar 2、Ar 4係選自由下列所組成之群組：苯基、聯苯、聯三苯、聯四苯、茀、螺二茀、萘、菲、蒽、聯伸三苯、丙二烯合茀(fluoranthene)、稠四苯、
Figure 111113074-001
(chrysene)、苯并蒽、苯并菲、芘、苝、吲哚、苯并呋喃、苯并噻吩、二苯并呋喃、二苯并噻吩、咔唑、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、喹諾酮、苯并吡啶、苯并嗒𠯤、苯并嘧啶、苯并咪唑和喹唑啉，彼等各自可經一或多個基團R取代；其中Ar 2、Ar 4也可為先前所引用的基團中之二或更多者的組合。特佳地，基團Ar 2、Ar 4係選自由下列所組成之群組：苯基、聯苯、聯三苯、聯四苯、茀、螺二茀、萘、蒽、菲、聯伸三苯、丙二烯合茀(fluoranthene)、稠四苯、
Figure 111113074-001
(chrysene)、苯并蒽、苯并菲、芘或苝、二苯并呋喃、咔唑和二苯并噻吩，彼等各自可在任何自由位置經一或多個基團R取代；及其中Ar 2、Ar 4也可為先前所引用的基團中之二或更多者的組合。非常特佳地，基團Ar 2、Ar 4係選自由下列所組成之群組：苯基、聯苯、聯三苯、聯四苯、茀、螺二茀、萘、蒽、菲、聯伸三苯、丙二烯合茀(fluoranthene)、二苯并呋喃、咔唑和二苯并噻吩，彼等各自可在任何自由位置經一或多個基團R取代；及其中Ar 2、Ar 4也可為先前所引用的基團中之二或更多者的組合。 適當基團Ar 2和Ar 4之實例為如下表中所示的式(Ar2-1)至(Ar2-27)之基團：
Figure 02_image061
Figure 02_image063
Figure 02_image065
其中虛線鍵表示至相鄰基團之鍵結及其中基團R 0具有與如上述相同的意義； 及其中該等式(Ar2-1)至(Ar2-27)之基團式可在各自由位置經具有與如上述相同的意義之基團R取代。 式(Ar2-1)至(Ar2-27)之基團中，式(Ar2-1)、(Ar2-2)、(Ar2-3)、(Ar2-4)、(Ar2-5)、(Ar2-8)、(Ar2-18)、(Ar2-19)之基團為較佳。式(Ar2-1)、(Ar2-2)、(Ar2-3)、(Ar2-4)、(Ar2-5)之基團為非常佳的。 較佳地，基團Ar S在每次出現時相同或不同地代表苯基、聯苯、茀、螺二茀、萘、菲、蒽、二苯并呋喃、二苯并噻吩、咔唑、吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、苯并吡啶、苯并嗒𠯤、苯并嘧啶和喹唑啉，彼等各自可經一或多個基團R取代。 適當基團Ar S之實例為如下表中所示的式(ArS-1)至(ArS-26)之基團：
Figure 02_image067
Figure 02_image069
其中虛線鍵表示至式(H1)或(H2)中相鄰基團之鍵結； 其中該等式(ArS-1)至(ArS-26)之基團可在各自由位置經具有與如上定義相同的意義之基團R取代；及 其中基團E每次出現時係相同或不同地選自-BR 0-、 -C(R 0) 2-、-Si(R 0) 2-、-C(=O)-、-O-、-S-、-S(=O)-、-SO 2-、-N(R 0)-、和-P(R 0)-， 其中R 0具有與上述相同的定義。 式(ArS-1)至(ArS-26)之基團中，式(ArS-1)、(ArS-2)、(ArS-3)、(ArS-11)和(ArS-12)之基團為較佳。式(ArS-1)、(ArS-2)、(ArS-3)之基團為非常佳的。 較佳地，R 0在每次出現時相同或不同地代表H、D、F、具有1至10個C原子之直鏈烷基或具有3至10個C原子之支鏈或環狀烷基(彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經O或S置換及其中一或多個H原子可經D或F置換)、或具有5至30個(較佳地6至18個)芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代，其中二個相鄰基團R 0可一起形成脂族或芳族環系統，其可經一或多個基團R取代； 較佳地，R在每次出現時相同或不同地代表H、D、F、CN、N(Ar) 2、具有1至40個(較佳1至20個，更佳1至10個) C原子之直鏈烷基、烷氧基或烷硫基或具有3至40個(較佳3至20個，更佳3至10個) C原子之支鏈或環狀烷基、烷氧基或烷硫基(彼等各自可經一或多個基團R’取代，其中在各情況下一或多個非相鄰的CH 2基團可經R’C=CR’、C≡C、O或S置換及其中一或多個H原子可經D或F置換)、或具有5至60個(較佳5至40個，更佳5至30個，特佳6至18個)芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R’取代。 較佳地，Ar在每次出現時相同或不同地為具有5至40個(較佳5至30個，更佳5至25個，非常更佳6至18個)芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R’取代； 較佳地，R’在每次出現時相同或不同地代表H、D，F、Cl、Br、I、CN、具有1至10個C原子之直鏈烷基或具有3至10個C原子之支鏈或環狀烷基(其中在各情況下一或多個H原子可經D或F置換)、或具有5至18個C原子之芳族或雜芳族環系統。 下列化合物為式(H1)化合物之實例：
Figure 02_image071
Figure 02_image073
Figure 02_image075
Figure 02_image077
Figure 02_image079
Figure 02_image081
Figure 02_image083
Figure 02_image085
Figure 02_image087
下列化合物為式(H2)化合物之實例：
Figure 02_image089
Figure 02_image091
Figure 02_image093
Figure 02_image095
Figure 02_image097
Figure 02_image099
Figure 02_image101
根據一較佳的實施態樣，組成物包含式(H1)化合物、式(H2)化合物和至少一種螢光發光體。詞句“至少一種螢光發光體”意指“一、二、三、或更多種螢光發光體”。 根據一非常佳的實施態樣，組成物包含作為第一主體材料之式(H1)化合物、作為第二主體材料之式(H2)化合物和作為摻雜劑材料之螢光發光體。 較佳地，組成物包含至少一種螢光發光體，其包含下列基團中之至少一者： - 包含三個直接鍵結至氮的經取代或未經取代之芳族或雜芳族環系統的芳基胺； - 橋聯三芳基胺； -具有至少14個芳族環原子之縮合芳族或雜芳族環系統； - 茚并茀、茚并茀胺或茚并茀二胺； - 苯并茚并茀、苯并茚并茀胺或苯并茚并茀二胺； - 二苯并茚并茀、二苯并茚并茀胺或二苯并茚并茀二胺； - 包含具有至少10個芳族環原子的縮合芳基之茚并茀； - 雙茚并茚并茀； - 茚并二苯并呋喃；茚并茀胺或茚并茀二胺； - 茀二聚物； - 啡㗁𠯤；或 - 硼衍生物。 更佳地，組成物包含至少一種如下所述的下列式(E-1)、(E-2)、(E-3)或E-4)中之一者的螢光發光體：
Figure 02_image103
其中 Ar 10、Ar 11、Ar 12在每次出現時相同或不同地為具有6至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R取代；其先決條件為至少一個基團Ar 10、Ar 11、Ar 12為具有10至40個芳族環原子之芳族或雜芳族環系統且包含至少一個由2至4個彼此縮合的芳族環組成的縮合芳基或雜芳基，其中該芳族或雜芳族環系統可經一或多個基團R取代； R    具有與上述相同的定義；及 e     為1、2、3或4；更佳地，e為1；
Figure 02_image105
其中 Ar 20、Ar 21、Ar 22在每次出現時相同或不同地為具有6至30個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R取代； E 20在每次出現時係相同或不同地選自BR、C(R 0) 2、Si(R 0) 2、C=O、C=NR 0、C=C(R 0) 2、O、S、S=O、SO 2、NR 0、PR 0、P(=O)R 0或P(=S)R 0；其中Ar 20、Ar 21和E 20一起形成五員環或六員環，及Ar 21、Ar 23和E 20一起形成五員環或六員環； R 0在每次出現時相同或不同地代表H、D、F、具有1至20個(較佳1至10個) C原子之直鏈烷基或具有3至20個(較佳為3至10個) C原子之支鏈或環狀烷基(彼等各自可經一或多個R基團取代，其中在各情況下一或多個非相鄰的CH 2基團可經O或S置換和其中一或多個H原子可經D或F置換)、或具有5至40個(較佳為5至30個，更佳為6至18個)芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)，其中兩個相鄰的基團R 0可一起形成脂族或芳族環系統，其可經一或多個基團R取代， R   具有與上述相同的定義； p、q 在每次出現時相同或不同地為0或1，其先決條件為p + q = 1； r     為1、2或3；
Figure 02_image107
其中 Ar 30、Ar 31、Ar 32在每次出現時相同或不同地代表具有5至22個(較佳5至18個，更佳6至14個)芳族環原子之經取代或未經取代之芳基或雜芳基； E 30代表B或N； E 31、E 32、E 33在每次出現時相同或不同地代表O、S、C(R 0) 2、C=O、C=S、C=NR 0、C=C(R 0) 2、Si(R 0) 2、BR 0、NR 0、PR 0、SO 2、SeO 2或化學鍵，其先決條件為若E 30為B，則基團E 31、E 32、E 33中之至少一者代表NR 0，及若E 30為N，則基團E 31、E 32、E 33中之至少一者代表BR 0； R 0具有與上述相同的定義； s、t、u 在每次出現時相同或不同地為0或1，其先決條件為s + t + u ≥ 1。
Figure 02_image109
其中 Ar 40、Ar 41、Ar 42在每次出現時相同或不同地代表具有5至22個(較佳5至18個，更佳6至14個)芳族環原子之經取代或未經取代之芳基或雜芳基； E 41、E 42、E 43在每次出現時相同或不同地代表O、S、C(R 0) 2、C=O、C=S、C=NR 0、C=C(R 0) 2、Si(R 0) 2、BR 0、NR 0、PR 0、SO 2、SeO 2或化學鍵，其先決條件為基團E 41、E 42、E 43中之至少一者存在且代表化學鍵； R 0具有與上述相同的定義； i、g、h 在每次出現時相同或不同地為0或1，其先決條件為i + g + h ≥ 1。 較佳地，式(E-1)之螢光發光體包含至少一個基團Ar 10、Ar 11或Ar 12，較佳為Ar 10，其係選自式(Ar 10-1)至(Ar 10-24)之基團：
Figure 02_image111
Figure 02_image113
Figure 02_image115
其中基團Ar 10-1至Ar 10-24可在所有自由位置經一或多個基團R取代；及其中 E 10在每次出現時係相同或不同地選自BR 0、C(R 0) 2、Si(R 0) 2、C=O、C=NR 0、C=C(R 0) 2、O、S、S=O、SO 2、NR 0、PR 0、P(=O)R 0或P(=S)R 0，較佳地E 10為C(R 0) 2； 其中R 0具有與上述相同的定義； E 11在每次出現時係相同或不同地選自C=O、O、S、S=O或SO 2，較佳為O或S，更佳為O；及 Ar 13在每次出現時相同或不同地為具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R取代。 根據一較佳實施態樣，式(E-1)之發光體包含基團Ar 10，其選自式(Ar 10-15)至(Ar 10-22)之基團，其中d較佳等於1及其中較佳地至少一個基團Ar 11、Ar 12係選自式(Ar 10-15)至(Ar 10-22)之基團。 根據一非常佳的實施態樣，式(E-1)之發光體係選自式(E-1-1)至(E-1-6)之發光體，
Figure 02_image117
Figure 02_image119
其中該等符號具有與上述相同的意義和其中： f     為0、1或2；及 上述在式(E-1-1)至(E-1-6)之化合物中所表示的苯環可在所有自由位置經一或多個基團R取代。 特佳地，式(E-1)化合物係選自式(E-1-1-A)至(E-1-6-A)之化合物，
Figure 02_image121
Figure 02_image123
Figure 02_image125
其中該等符號和標號具有與上述相同的意義及其中上述在式(E-1-1-A)至(E-1-6-A)之化合物中所表示的苯環可在所有自由位置經一或多個基團R取代。 較佳地，式(E-2)之螢光發光體係選自式(E-2-1)至(E-2-43)之螢光發光體，
Figure 02_image127
Figure 02_image129
Figure 02_image131
Figure 02_image133
Figure 02_image135
Figure 02_image137
其中式(E-2-1)至(E-2-43)之基團可在所有自由位置經一或多個基團R取代；及其中E 20具有與上述相同的定義。較佳地，E 20為C(R 0) 2。 式(E-2)化合物較佳係選自式(E-2-32)至(E-2-43)之化合物。更佳地，式(E-2)化合物係選自化合物(E-2-32-A)至(E-2-43-A)：
Figure 02_image139
Figure 02_image141
Figure 02_image143
其中該等符號具有與上述相同的意義及其中上述在式(E-2-32-A)至(E-2-43-A)之化合物中所表示的苯和萘環可在所有自由位置經一或多個基團R取代。 較佳地，式(E-3)之螢光發光體係選自式(E-3-1)之螢光發光體，
Figure 02_image145
其中該等符號和標號具有與上述相同的意義。 更佳地，式(E-3)之螢光發光體係選自式(E-3-2)之螢光發光體，
Figure 02_image147
其中該等符號E 30至E 33具有與上述相同的意義；其中t為0或1，其中當t為0時，基團E 32不存在和基團 R 10存在，其置換E 32的鍵；及其中 R 10在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R’) 2、N(Ar) 2、NO 2、Si(R’) 3、B(OR’) 2、OSO 2R’、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基(彼等各自可經一或多個基團R’取代，其中在各情況下一或多個非相鄰的CH 2基團可經R’C=CR’、C≡C、Si(R’) 2、Ge(R’) 2、Sn(R’) 2、C=O、C=S、C=Se、P(=O)(R’)、SO、SO 2、O、S或CONR’置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換)、具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R’取代)、或具有5至60個芳族環原子之芳氧基(其可經一或多個基團R’取代)；其中二個相鄰的取代基R 10可一起形成脂族或芳族環系統，其可經一或多個基團R’取代；其中R’具有與上述相同的定義。 甚至更佳地，式(E-3)之螢光發光體係選自式(E-3-3)和(E-3-4)之螢光發光體，
Figure 02_image149
其中該等符號和標號具有與上述相同的意義。 較佳地，式(E-4)之螢光發光體係選自式(E-4-1)或E-4-2)之螢光發光體，
Figure 02_image151
其中 E 41和E 42在每次出現時相同或不同地代表O、S、C(R 0) 2、C=O、C=S、C=NR 0、C=C(R 0) 2、Si(R 0) 2、BR 0、NR 0、PR 0、SO 2、SeO 2或化學鍵，其中E 41較佳為鍵； R 20在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R’) 2、N(Ar) 2、NO 2、Si(R’) 3、B(OR’) 2、OSO 2R’、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基(彼等各自可經一或多個基團R’取代，其中在各情況下一或多個非相鄰的CH 2基團可經R’C=CR’、C≡C、Si(R’) 2、Ge(R’) 2、Sn(R’) 2、C=O、C=S、C=Se、P(=O)(R’)、SO、SO 2、O、S或CONR’置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換)、具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R’取代)、或具有5至60個芳族環原子之芳氧基(其可經一或多個基團R’取代)；其中二個相鄰的取代基R 20可一起形成脂族或芳族環系統，其可經一或多個基團R’取代；其中R’具有與上述相同的定義； g    為0或1。 更佳地，式(E-4)之螢光發光體係選自式(E-4-1-A)或(E-4-2-A)之螢光發光體，
Figure 02_image153
其中該等符號具有與上述相同的意義。 根據一較佳實施態樣，式(E-1)、(E-2)、(E-3)或(E-4)之螢光發光體包含基團RS，其中基團RS係： -     選自以式(RS-a)之基團的下列通式表示之支鏈或環狀烷基，
Figure 02_image155
其中 R 22、R 23、R 24在每次出現時係相同或不同地選自H、具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基，其中上述基團可各自經一或多個基團R 25取代，且其中基團R 22、R 23、R 24中之二者或所有基團R 22、R 23、R 24可連接以形成(多)環狀烷基，其可經一或多個基團R 25取代； R 25在每次出現時係相同或不同地選自具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基； 其先決條件為在每次出現時，基團R 22、R 23和R 24中之至少一者不為H，其先決條件為在每次出現時，所有基團R 22、R 23和R 24一起具有至少4個碳原子且先決條件為在每次出現時，若基團R 22、R 23、R 24中之二者為H，則其餘基團不為直鏈；或 -     選自以下列通式(RS-b)表示之支鏈或環狀烷氧基
Figure 02_image157
其中 R 26、R 27、R 28在每次出現時係相同或不同地選自H、具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基，其中上述基團可各自經一或多個如上定義之基團R 25取代，且其中基團R 26、R 27、R 28中之二者或所有基團R 26、R 27、R 28可連接以形成(多)環狀烷基，其可經一或多個如上定義之基團R 25取代； 其先決條件為在每次出現時，基團R 26、R 27和R 28中只有一者可為H； -     選自以下列通式(RS-c)表示之芳烷基
Figure 02_image159
其中 R 29、R 30、R 31在每次出現時係相同或不同地選自H、具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基，其中上述基團可各自經一或多個基團R 32取代、或具有6至30個芳族環原子之芳族環系統，其在各情況下可經一或多個基團R 32取代，且其中基團R 29、R 30、R 31中之二者或全部可連接以形成(多)環狀烷基或芳族環系統，彼等各自可經一或多個基團R 32取代； R 32在每次出現時係相同或不同地選自具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基、或具有6至24個芳族環原子之芳族環系統； 其先決條件為在每次出現時，基團R 29、R 30和R 31中之至少一者不為H，且在每次出現時，基團R 29、R 30和R 31中之至少一者為或包含具有至少6個芳族環原子之芳族環系統； -     選自以下列通式(RS-d)表示之芳族環系統
Figure 02_image161
其中 R 40至R 44在每次出現時係相同或不同地選自H、具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基，其中上述基團可各自經一或多個基團R 32取代、或具有6至30個芳族環原子之芳族環系統，其在各情況下可經一或多個基團R 32取代，且其中基團R 40至R 44中之二或更多者可連接以形成(多)環狀烷基或芳族環系統，彼等各自可經一或多個如上定義之基團R 32取代；或 -     選自式(RS-e)之基團，
Figure 02_image163
其中式(RS-e)中之虛線鍵表示至螢光發光體的鍵結，其中Ar 50、Ar 51在每次出現時相同或不同地代表具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代；及其中m為選自1至10的整數。 較佳地，式(RS-e)之基團中的標號m為選自1至6，非常佳地選自1至4的整數。 較佳地，其中Ar 50、Ar 51在每次出現時相同或不同地代表具有5至40個(較佳5至30個，更佳6至18個)芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代。更佳地，Ar 50、Ar 51係選自苯基、聯苯、聯三苯(terphenyl)、聯四苯(quaterphenyl)、茀、螺二茀、萘、蒽、菲、聯伸三苯(triphenylene)、丙二烯合茀(fluoranthene)、二苯并呋喃、咔唑和二苯并噻吩，其在各情況下可經一或多個基團R取代。非常佳地，至少一個基團Ar 50或Ar 51為茀，其可經一或多個基團R取代。 更特別地，較佳的是至少一個基團Ar 50代表式(Ar50-2)之基團及/或至少一個基團Ar 51代表式(Ar51-2)之基團，
Figure 02_image165
其中 式(Ar50-2)中之虛線鍵表示至螢光發光體和至基團Ar 50或Ar 51的鍵結；及式(Ar51-2)中之虛線鍵表示至Ar 50的鍵結； E 4係選自-C(R 0a) 2-、-Si(R 0a) 2-、-O-、-S-或-N(R 0a)-，較佳為-C(R 0a) 2； R 0a在每次出現時相同或不同地代表H、D、F、CN、具有1至40個(較佳1至20個，更佳1至10個) C原子之直鏈烷基或具有3至40個(較佳3至20個，更佳3至10個) C原子之支鏈或環狀烷基(彼等各自可經一或多個基團R取代)、具有5至60個(較佳5至40個，更佳5至30個，非常佳5至18個)芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R取代)；其中二個相鄰的取代基R 0a可形成單環或多環的脂族環系統或芳族環系統，其可經一或多個基團R取代，其具有與上述相同的意義；及 式(Ar50-2)和(Ar51-2)之基團可在各自由位置經基團R取代，該基團R具有與上述相同的意義。 基團RS較佳位於其中RS替代R、R 0或R’之位置。 可使用於包含式(H1)和(H2)化合物之組成物中的螢光發光體之實例為芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族
Figure 111113074-001
胺(chrysenamine)或芳族
Figure 111113074-001
二胺。芳族蒽胺意指其中一個二芳胺基直接鍵結至蒽基(較佳在9位置)的化合物。芳族蒽二胺意指其中兩個二芳胺基直接鍵結至蒽基(較佳在9,10-位置)的化合物。芳族芘胺、芘二胺、
Figure 111113074-001
胺及
Figure 111113074-001
二胺係與其類似地定義，其中二芳胺基較佳地鍵結至芘之1-位置或1,6-位置。其他較佳發光體為橋聯三芳基胺(例如根據WO 2019/111971、WO2019/240251和WO 2020/067290)。其他較佳發光體為茚并茀胺或茚并茀二胺(例如根據WO 2006/108497或WO 2006/122630)、苯并茚并茀胺或苯并茚并茀二胺(例如根據WO 2008/006449)、及二苯并茚并茀胺或二苯并茚并茀二胺(例如根據WO 2007/140847)、和WO 2010/012328中所揭示之包含縮合芳基之茚并茀衍生物。又其他較佳發光體為如WO 2015/158409中所揭示之苯并蒽衍生物、如WO 2017/036573中所揭示之蒽衍生物、如WO 2016/150544中之經由雜芳基連接的茀二聚物或如WO 2017/028940和WO 2017/028941中所揭示之啡㗁𠯤衍生物。同樣較佳者為WO 2012/048780和WO 2013/185871中所揭示之芘芳基胺(pyrenarylamine)。同樣較佳者為WO 2014/037077中所揭示之苯并茚并茀胺、WO 2014/106522中所揭示之苯并茀胺和WO 2014/111269或WO 2017/036574、WO 2018/007421中所揭示之茚并茀。較佳亦為如WO 2018/095888、WO 2018/095940、WO 2019/076789、WO 2019/170572以及未公開申請案PCT/EP2019/072697、PCT/EP2019/072670和PCT/EP2019/072662中所揭示之包含二苯并呋喃或茚并二苯并呋喃部分之發光體。同樣較佳者為如例如WO 2015/102118、CN108409769、CN107266484、 WO2017195669、US2018069182中以及未公開申請案EP 19168728.4、EP 19199326.0和EP 19208643.7中所揭示之硼衍生物。 在本發明的情況下，非常適合的螢光發光體為WO 2018/007421中所揭示之茚并茀衍生物和WO 2019/076789中所揭示之二苯并呋喃衍生物。 可使用於包含式(H1)和(H2)化合物之組成物的較佳螢光發光化合物之實例係描述於下表中：
Figure 02_image167
Figure 02_image169
Figure 02_image171
Figure 02_image173
Figure 02_image175
Figure 02_image177
Figure 02_image179
Figure 02_image181
Figure 02_image183
Figure 02_image185
Figure 02_image187
Figure 02_image189
Figure 02_image191
Figure 02_image193
Figure 02_image195
Figure 02_image197
Figure 02_image199
Figure 02_image201
Figure 02_image203
Figure 02_image205
Figure 02_image207
Figure 02_image209
Figure 02_image211
Figure 02_image213
Figure 02_image215
Figure 02_image217
Figure 02_image219
Figure 02_image221
Figure 02_image223
Figure 02_image225
Figure 02_image227
Figure 02_image229
Figure 02_image231
Figure 02_image233
Figure 02_image235
Figure 02_image237
Figure 02_image239
Figure 02_image241
Figure 02_image243
Figure 02_image245
Figure 02_image247
Figure 02_image249
Figure 02_image251
Figure 02_image253
Figure 02_image255
Figure 02_image257
Figure 02_image259
Figure 02_image261
根據本發明，式(H1)化合物和式(H2)化合物一起存在於組成物中，較佳存在於均勻混合物中。 較佳地，式(H1)化合物係以1-99%，較佳10-90%，更佳20-80%，特佳30-75%，非常特佳35-70%的比例存在於組成物中。 較佳地，式(H2)化合物係以1-99%，較佳10-90%，更佳20-80%，特佳25-70%，非常特佳30-60%的比例存在於根據本發明之組成物中。 根據一較佳實施態樣，根據本發明之組成物另外包含至少一種螢光發光體。在此情況下，較佳的是螢光發光體係以0.1和50.0%，較佳介於0.5和20.0%之間，特佳地介於1.0和10.0%之間的比例存在於組成物中。 就本申請案目的而言，以%表示的比例規格，若化合物是從氣相中施加，則意指體積%，及若化合物是從溶液施加，則意指重量%。 為了從液相處理根據本發明之化合物(例如藉由塗佈方法如旋轉塗佈或藉由印刷方法)，需要根據本發明之組成物的調配物。此等調配物可為例如溶液、分散液或乳液。為此目的，較佳可為使用二或更多種溶劑之混合物。溶劑較佳地選自有機和無機溶劑，更佳地有機溶劑。溶劑非常佳地選自烴、醇、酯、醚、酮和胺。適合且較佳的溶劑為(例如)甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、對稱三甲苯、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二㗁烷、苯氧基甲苯(特別是3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、1-乙基萘、癸基苯、苯基萘、異戊酸薄荷酯、異丁酸對甲苯基酯、己酸環己酯(cyclohexal hexanoate)、對甲苯甲酸乙酯、鄰甲苯甲酸乙酯、間甲苯甲酸乙酯、十氫萘、2-甲氧基苯甲酸乙酯、二丁基苯胺、二環己基酮、異山梨醇二甲基醚、十氫萘、2-甲基聯苯、辛酸乙酯、辛酸辛酯、癸二酸二乙酯、3,3-二甲基聯苯、1,4-二甲基萘、2,2’-二甲基聯苯、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、茚烷、NMP、對-異丙基甲苯、苯基乙基醚、1,4-二異丙基苯、二苯甲基醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷或此等溶劑之混合物。 本發明因此再者關於一種包含根據本發明之式(H1)化合物和式(H2)化合物及至少一種溶劑之調配物。溶劑可為上述溶劑中之一者或這些溶劑的混合物。 有機溶劑在根據本發明之調配物中的比例基於調配物的總重量較佳為至少60重量%，較佳為至少70重量%和更佳為至少80重量%。 根據本發明之調配物可用於製造一層或多層結構，其中依據製造較佳的電子或光電組件(例如OLED)之要求，有機功能材料可存在於該等層中。 本發明之調配物較佳可使用於在基板上或在施加至基板的層之一者上形成包含根據本發明之組成物的功能層。 本發明的又另一目的為一種製造電子裝置之方法，其中至少一層係從施加本發明調配物而獲得。較佳地，將根據本發明之調配物施加於基板或另一層並接著乾燥。 得自根據本發明之調配物的功能層可例如以泛塗(flood coating)、浸塗、噴塗、旋轉塗佈、網版印刷、凸版印刷、凹版印刷、旋轉印刷、輥塗、快乾印刷(flexographic printing)、平版印刷或噴嘴印刷，較佳噴墨印刷在基板上或施加至基板之層中的一者而製得。 根據本發明之調配物施加至基板或已施加的功能層之後，可進行乾燥步驟以便移除溶劑。較佳地，乾燥步驟包含真空乾燥，其較佳接著進行層的退火。真空乾燥在此較佳可在從10 -7毫巴至1巴之範圍，特佳在從10 -6毫巴至1巴之範圍的壓力下進行。真空乾燥較佳在從10至40℃，更佳15至30℃之範圍的溫度下進行。真空乾燥步驟較佳接著層的熱退火。層的熱退火較佳在從120℃至180℃，較佳從130℃至170℃，更佳140℃至160℃的溫度下進行。 因此，本發明關於一種製造電子裝置之方法，該電子裝置包含至少一層包含根據本發明之組成物的層，其中該方法包含下列步驟： a) 製備一種根據本發明之調配物； b) 將步驟a)中製備的調配物施加在基板上或另一層上以形成包含根據本發明之組成物的層； c) 將該層乾燥以移除溶劑。 較佳地，在步驟b)中，調配物係藉由從液相處理，更佳地經由塗佈方法或印刷方法，非常更佳地藉由印刷方法，特佳地藉由噴墨印刷方法而施加。 本發明的另一目標為電子裝置，其包含陽極、陰極和至少一個介於二者之間的功能層，其中此功能層包含根據本發明之組成物。較佳地，包含根據本發明之組成物的該至少一個功能層為發光層。 電子裝置較佳係選自有機電致發光裝置(OLED)、有機積體電路、有機場效電晶體、有機薄膜電晶體、有機發光電晶體、有機太陽能電池、有機染料敏化太陽能電池、有機光學檢測器、有機感光器(photoreceptor)、有機場淬滅裝置、發光電化學電池、有機雷射二極體和有機電漿子發射裝置。更佳地，電子裝置為有機電致發光裝置(OLED)。 有機電致發光裝置包含陰極、陽極和至少一個發光層，其包含根據本發明之組成物。除了此等層以外，有機電致發光裝置亦可包含其他層，例如在各情況下一或多個電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、激子阻擋層、電子阻擋層、及/或電荷產生層。同樣可能在二個發光層之間引入具有例如激子阻擋功能之中間層。然而，應指出的是此等層各者不一定必須存在。有機電致發光裝置在此可包含一個發光層或多個發光層。若存在多個發光層，則此等較佳地具有總計多個在380 nm和750 nm之間的發光最大值，整體導致白色發光，亦即將能夠發螢光或磷光的各種發光化合物使用於發光層中。特佳者為具有三個發光層之系統，其中該三層呈現藍色、綠色及橙色或紅色發光(基本結構參見例如WO 2005/011013)。此等可為螢光或磷光發光層或其中螢光和磷光發光層彼此組合的混合系統。 所涉及的電子裝置可包含單一發光層，其包含根據本發明之組成物，或其可包含二更多個發光層。 根據本發明之組成物可包含一或多種其他基質材料。 較佳其他基質材料係選自下列之類別：寡聚伸芳基(oligoarylene)(例如根據EP 676461之2,2’,7,7’-四苯基螺二茀或二萘基蒽)，特別是包含縮合芳族基團之寡聚伸芳基、寡聚伸芳基伸乙烯基(oligoarylenevinylene)(例如根據EP 676461之DPVBi或螺-DPVBi)、多牙(polypodal)金屬錯合物(例如根據WO 2004/081017)、電洞傳導化合物(例如根據WO 2004/058911)、電子傳導化合物，特別是酮、氧化膦、亞碸、等等(例如根據WO 2005/084081和WO 2005/084082)、阻轉異構物(例如根據WO 2006/048268)、硼酸衍生物(例如根據WO 2006/117052)或苯并蒽(例如根據WO 2008/145239)。特佳基質材料係選自下列之類別：包含萘、蒽、苯并蒽及/或芘或這些化合物的阻轉異構物之寡聚伸芳基、寡聚伸芳基伸乙烯基、酮、氧化膦和亞碸。非常特佳的基質材料係選自下列之類別：包含蒽、苯并蒽、苯并菲及/或芘或這些化合物的阻轉異構物之寡聚伸芳基。寡聚伸芳基就本發明的意義而言意指一種其中至少三個芳基或伸芳基彼此鍵結之化合物。 用作為根據本發明之有機電致發光裝置中的對應功能材料之一般較佳材料類別係表示於下。 適當電荷傳輸材料，如可使用於根據本發明之電子裝置的電洞注入或電洞傳輸層或電子阻擋層或於電子傳輸層中，為(例如) Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010中所揭示之化合物或根據先前技術使用於此等層中之其他材料。 可使用於電子傳輸層之材料為根據先前技術用作為電子傳輸層中之電子傳輸材料的所有材料。特別適合的是鋁錯合物(例如，Alq 3)、鋯錯合物(例如，Zrq 4)、鋰錯合物(例如LiQ)、苯并咪唑衍生物、三𠯤衍生物、嘧啶衍生物、吡啶衍生物、吡𠯤衍生物、喹㗁啉衍生物、喹啉衍生物、㗁二唑衍生物、芳族酮、內醯胺、硼烷、二氮磷雜環戊二烯(diazaphosphole)衍生物和氧化膦衍生物。此外，適當材料為上述化合物之衍生物，如JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中所揭示。 可用於根據本發明之電致發光裝置中的電洞傳輸層、電洞注入層或電子阻擋層中之較佳電洞傳輸材料為茚并茀胺衍生物(例如根據WO 06/122630或WO 06/100896)、EP 1661888中所揭示之胺衍生物、六氮雜聯伸三苯衍生物(例如根據WO 01/049806)、包含縮合芳族環之胺衍生物(例如根據US 5,061,569)、WO 95/09147中所揭示之胺衍生物、單苯并茚并茀胺(例如根據WO 08/006449)、二苯并茚并茀胺(例如根據WO 07/140847)、螺二茀胺(例如根據WO 2012/034627或WO 2013/120577)、茀胺(例如根據申請案EP 2875092、EP 2875699和EP 2875004)、螺二苯并哌喃胺(例如根據WO 2013/083216)和二氫吖啶衍生物(例如根據WO 2012/150001)。根據本發明之化合物也可用作為電洞傳輸材料。 有機電致發光裝置之陰極較佳包含具有低功函數之金屬、金屬合金或包含各種金屬之多層結構，諸如，例如鹼土金屬、鹼金屬、主族金屬或鑭系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm、等等)。亦適合的是包含鹼金屬或鹼土金屬和銀之合金，例如包含鎂和銀之合金。在多層結構之情況中，除該等金屬外，也可使用具有較高功函數之其他金屬，諸如(例如)Ag或Al，在該情況中通常使用金屬之組合，諸如(例如)Ca/Ag、Mg/Ag或Ag/Ag。較佳亦可於金屬陰極與有機半導體之間引入具有高介電常數之材料的薄中間層。適合於此目的者為(例如)鹼金屬氟化物或鹼土金屬氟化物，但對應氧化物或碳酸鹽(例如LiF、Li 2O、BaF 2、MgO、NaF、CsF、Cs 2CO 3、等等)亦適合。此外，喹啉酸鋰(LiQ)可使用此目的。此層之層厚度較佳係介於0.5和5 nm之間。 陽極較佳包含具有高功函數之材料。陽極較佳具有相對於真空為大於4.5 eV之功函數。適合於此目的者一方面為具有高氧化還原電位之金屬，諸如(例如)Ag、Pt或Au。另一方面，金屬/金屬氧化物電極(例如Al/Ni/NiO x、Al/PtO x)亦可為較佳的。就一些應用而言，電極中之至少一者必須是透明或部分透明的，以便促進有機材料之照射(有機太陽能電池)或光之耦合輸出(coupling-out)(OLED、O-雷射)。較佳陽極材料在此為導電性混合金屬氧化物。特佳者為氧化銦錫(ITO)或氧化銦鋅(IZO)。此外較佳者為導電性摻雜型有機材料，特別是導電性摻雜型聚合物。 將裝置適當地(視應用而定)結構化，配備接點且最後密封，因為根據本發明之裝置的壽命在水及/或空氣存在下被縮短。 在一較佳實施態樣中，根據本發明之有機電致發光裝置特徵在於一或多層係利用昇華方法塗佈，其中該等材料係於真空昇華單元中在低於10 ‑5毫巴，較佳低於10 ‑6毫巴之初壓力下藉由氣相沈積施加。然而，初壓力在此也可能甚至更低，例如低於10 ‑7毫巴。 同樣較佳者為一種有機電致發光裝置，其特徵在於利用OVPD(有機氣相沈積)方法或輔以載體-氣體昇華法塗佈一或多層，其中該等材料係在介於10 -5毫巴和1巴之間的壓力下施加。此方法的一特殊例子為OVJP(有機氣相噴墨印刷)方法，其中該等材料係透過噴嘴直接施加且因此結構化(例如M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301)。 此外較佳者為一種有機電致發光裝置，其特徵在於一或多層係諸如(例如)以旋轉塗佈或利用任何所欲印刷方法(諸如，例如網版印刷、快乾印刷、噴嘴印刷或平版印刷，但特佳為LITI(光誘導熱成像、熱轉移印刷)或噴墨印刷)從溶液製造。為此目的需要可溶性式(I)化合物。高溶解度可透過該等化合物之適當取代而達成。 亦可能者為混合方法，其中，例如，一或多層係從溶液施加且一或多個其他層係藉由氣相沈積施加。因此，例如，可能從溶液施加發光層且可能藉由氣相沈積施加電子傳輸層。 此等方法通常為熟習此項技術者已知且可由熟習此項技術者可在無進步性(inventive step)下應用於包含根據本發明之化合物的有機電致發光裝置。 根據本發明，包含一或多種根據本發明之化合物的電子裝置可使用於顯示器中、作為照明應用中之光源及作為醫學及/或美容應用(例如光療法)中之光源。 現將以下列實施例更詳細地解釋本發明，而不希望因此限制本發明。 The present invention is therefore based on the technical aim of providing compositions comprising OLED materials suitable for use in electronic devices such as OLEDs, more particularly as matrix components for fluorescent emitters. The invention is also based on the technical aim of providing compositions comprising OLED materials which are particularly suitable for solution processing. The invention is also based on the technical aim of providing a method. In research on novel compositions for use in electronic devices, it has now been found that compositions comprising compounds of formula (H1) and compounds of formula (H2) as defined below are very suitable for use in electronic devices. In particular, they achieve one or more of the above technical objectives, preferably all of them. The present application therefore relates to a composition comprising a compound of formula (H1) and a compound of formula (H2),
Figure 02_image001
Figure 02_image003
Wherein the following applies for the symbols and designations used: E 1 , E 2 , E 3 and E 4 represent, identically or differently at each occurrence, a single bond, -BR 0 -, -C(R 0 ) 2 -, - Si(R 0 ) 2 -, -C(=O)-, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 )-, or -P(R 0 )-; the prerequisite is that, in the ring containing E 1 and E 3 , only one group E 1 or E 3 can be a single bond, and in the ring containing E 2 and E 4 , only one group E 2 or E 4 may be a single bond; E 5 represents O or S; X 1 to X 12 represent CR X , C-Ar X or N identically or differently at each occurrence; its prerequisite is that at least one is selected from X The group of 1 to X 12 represents the group C-Ar X and Ar X represents the group of formula (Ar X ):
Figure 02_image005
wherein the dotted bond represents a bond to group C in C-Ar X ; Z 1 to Z 8 represent CR Z , C-Ar Z or N identically or differently at each occurrence; a prerequisite for which is at least one of the selected The group from Z 1 to Z 8 represents the group C-Ar Z and Ar Z represents the group of formula (Ar Z ):
Figure 02_image007
where the dotted bond represents the bond to group C in C-Ar Z ; Ar 1 is identically or differently at each occurrence an aryl or heteroaryl group having 10 to 60 aromatic ring atoms, which in each In each case it can also be substituted by one or more radicals R V ; Ar 3 is identically or differently at each occurrence an aryl or heteroaryl group having 10 to 60 aromatic ring atoms, which in each case is also may be substituted by one or more radicals RY ; Ar 2 , Ar 4 , Ar S are identically or differently at each occurrence an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which In each case also substitution by one or more radicals R; R V , R X , RY , R Z represent H, D, F, Cl, Br, I, CHO identically or differently at each occurrence , CN, C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R) 2 , N(Ar) 2 , NO 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, linear alkyl, alkoxy or thioalkyl with 1 to 40 C atoms or branched chain with 3 to 40 C atoms or cyclic alkyl, alkoxy or alkylthio groups, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH groups may be substituted by RC=CR , C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O , S or CONR replacement and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or aryloxy groups having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R; wherein two radicals R V , two groups R X , two groups R Y , two groups R Z may together form an aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R; R 0 Represents H, D, F, straight-chain alkyl having 1 to 20 C atoms, or branched or cyclic alkyl having 3 to 20 C atoms identically or differently at each occurrence, each of which may Substituted by one or more groups R, where in each case one or more non-adjacent CH groups may be replaced by O or S and where one or more H atoms may be replaced by D or F, or with Aromatic or heteroaromatic ring systems of 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R, wherein two adjacent radicals R 0 , may together form an aliphatic or Aromatic ring systems, which may be substituted by one or more radicals R; R at each occurrence identically or differently represents H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar , P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R') 2 , N(Ar) 2 , NO 2 , Si(R') 3 , B (OR') 2 , OSO 2 R', linear alkyl, alkoxy or thioalkyl with 1 to 40 C atoms or branched or cyclic alkyl with 3 to 40 C atoms , alkoxy or alkylthio, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH groups may be substituted by R'C=CR', C≡C, Si(R') 2 , Ge(R') 2 , Sn(R') 2 , C=O, C=S, C=Se, P(=O)(R'), SO, SO 2 , O, S or CONR' replacement and wherein one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 , aromatic or heteroaromatic with 5 to 60 aromatic ring atoms Aromatic ring systems, which in each case may be substituted by one or more radicals R', or aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R'; wherein Two radicals R may together form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R'; Ar is, in each occurrence, identically or differently, an aliphatic or aromatic ring system having from 5 to 60 aromatic ring atoms Aromatic or heteroaromatic ring systems, which may in each case also be substituted by one or more radicals R';R', identically or differently at each occurrence, represents H, D, F, Cl, Br, I , CN, straight-chain alkyl, alkoxy or alkylthio with 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or alkylthio with 3 to 20 C atoms, wherein In each case one or more non-adjacent CH2 groups may be replaced by SO, SO2 , O, S and one or more H atoms may be replaced by D, F, Cl, Br or I, or have Aromatic or heteroaromatic ring systems of 5 to 24 aromatic ring atoms; and p, s are identically or differently 0 or 1 at each occurrence, wherein: when p or s is 0, then corresponds to ArS Absent and group Ar 1 or Ar 3 is directly bonded to C in C-Ar X or C-Ar Z ; q, t are identically or differently 0, 1 or 2 at each occurrence, wherein: when q When 0, then Ar 4 does not exist; when t is 0, then Ar 2 does not exist; when q is 1 or 2, then Ar 1 is replaced by one group or two groups Ar 4 ; when t is When 1 or 2, then Ar 3 is substituted by one group or two groups Ar 2 . Furthermore, the following definitions of chemical groups apply for the purposes of this application: Aryl in the sense of the present invention contains 6 to 60 aromatic ring atoms, preferably 6 to 40 aromatic ring atoms, more preferably 6 to 40 aromatic ring atoms 20 aromatic ring atoms; heteroaryl in the sense of the present invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, wherein At least one is a heteroatom. Heteroatoms are preferably selected from N, O and S. This represents the basic definition. If other preferences are indicated in the description of the invention, eg with regard to the number of aromatic ring atoms or heteroatoms present, these apply. Aryl or heteroaryl here means a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, such as pyridine, pyrimidine or thiophene, or a condensed (annellated) aromatic or heteroaromatic polycyclic ring, For example naphthalene, phenanthrene, quinoline or carbazole. Condensed (fused) aromatic or heteroaromatic polycycles in the sense of the present application consist of two or more simple aromatic or heteroaromatic rings condensed with one another. Aryl or heteroaryl which may in each case be substituted by the groups mentioned above and which may be attached via any desired position to an aromatic or heteroaromatic ring system means in particular radicals derived from: benzene, naphthalene, anthracene, phenanthrene , pyrene, dihydropyrene,
Figure 111113074-001
(chrysene), perylene, fluoranthene, benzanthracene, triphenylene, condensed tetraphenyl, condensed pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran , thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6 -Quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenanthium, phenanthyl, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole , phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthracene Anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, thiazole, benzothraxazole, pyrimidine, benzopyrimidine, quinine phenoline, pyridine, phenanthroline, phenidine, azacarbazole, benzocarboline, morpholine, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2 ,3-Oxadiazole, 1,2,4-Oxadiazole, 1,2,5-Oxadiazole, 1,3,4-Oxadiazole, 1,2,3-Thiadiazole, 1,2 ,4-Thiadiazole, 1,2,5-Thiadiazole, 1,3,4-Thiadiazole, 1,3,5-Trisadiazole, 1,2,4-Trisadiazole, 1,2,3 -Trizole, tetrazole, 1,2,4,5-tetrazole, 1,2,3,4-tetrazole, 1,2,3,5-tetrazole, purine, pteridine, ind
Figure 111113074-002
and benzothiadiazoles. Aryloxy as defined according to the invention means an aryl group as defined above, which is bonded via an oxygen atom. Similar definitions apply to heteroaryloxy. The aromatic ring system in the sense of the present invention comprises 6 to 60 C atoms, preferably 6 to 40 C atoms, more preferably 6 to 20 C atoms in the ring system. Heteroaromatic ring systems in the sense of the present invention comprise 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is heteroatoms. Heteroatoms are preferably selected from N, O and/or S. Aromatic or heteroaromatic ring systems in the sense of the present invention are meant not necessarily to contain only aryl or heteroaryl groups, but in which additionally a plurality of aryl or heteroaryl groups can be formed by means of non-aromatic units (preferably Systems that are less than 10% atoms other than H) (such as, for example, sp 3 -mixed C, Si, N or O atoms, sp 2 -mixed C or N atoms, or sp-mixed C atoms). Thus, for example, systems such as 9,9'-spirobistilbene, 9,9'-diarylstilbene, triarylamine, diaryl ether, stilbene, etc. are also intended to be in the sense of the present invention An aromatic ring system such as a system in which two or more aryl groups are linked, for example, via a linear or cyclic alkyl, alkenyl or alkynyl group or via a silicon group. Furthermore, systems in which two or more aryl or heteroaryl groups are linked to one another via single bonds are also aromatic or heteroaromatic ring systems within the meaning of the present invention, such as, for example, systems such as biphenyl, biphenyl Benzene or diphenyltriphenyl. Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may also be substituted in each case by radicals as defined above and which may be attached to the aromatic or heteroaromatic group via any desired position In particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, pyrene,
Figure 111113074-001
(chrysene), perylene, fluoranthene, condensed tetraphenyl, condensed pentaphenyl, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene , bitetraphenyl (quaterphenyl), fennel, spirodifenole, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, truxene, isotruxene, Spiroindene, spiroisotriindene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindene Indole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline , benzo-7,8-quinoline, phenanthrimidazole, phenanthrimidazole, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole ), pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole , Isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, thiazole, benzopyrimidine, pyrimidine, benzopyrimidine, quinzoline, 1,5-diazaanthracene, 2, 7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10 -Tetraazaperylene, pyridine, phenanthroline, phenanthene, morphine, fluorubin, fenidine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-tri Azole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3, 4-thiadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3, 5-three 𠯤, 1,2,4-three 𠯤, 1,2,3-three 𠯤, tetrazole, 1,2,4,5-tetra 𠯤, 1,2,3,4-tetra 𠯤, 1, 2,3,5-Tetramethalone, Purine, Pteridine, Ind
Figure 111113074-002
and benzothiadiazole, or a combination of these groups. For the purposes of the present invention, straight-chain alkyl having 1 to 40 C atoms or branched or cyclic alkyl having 3 to 40 C atoms or alkenyl or alkynyl having 2 to 40 C atoms , wherein, in addition, individual H atoms or CH groups may be substituted by groups under the definition of these groups above, preferably meaning the groups methyl, ethyl, n-propyl, isopropyl, n-butyl Base, isobutyl, secondary butyl, tertiary butyl, 2-methylbutyl, n-pentyl, secondary pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n- Heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butene Base, Pentenyl, Cyclopentenyl, Hexenyl, Cyclohexenyl, Heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Ethynyl, Proynyl, Butynyl, Pentyl Alkynyl, hexynyl or octynyl. Alkoxy or alkylthio having 1 to 40 C atoms preferably means methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy radical, secondary butoxy, tertiary butoxy, n-pentyloxy, secondary pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy Base, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio , isopropylthio, n-butylthio, isobutylthio, secondary butylthio, tertiary butylthio, n-pentylthio, secondary pentylthio, n-hexylthio, cyclohexylthio, n-heptyl Thio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, Vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio , cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio. For the purposes of this application, the statement that two or more groups can form a ring with each other means in particular that two groups are linked to each other by a chemical bond. This is illustrated in the following diagrams:
Figure 02_image009
In addition, however, the above statement also means that, in the case where one of the two groups represents hydrogen, the second group is bonded to the position to which the hydrogen atom is bonded, and forms a ring. This is illustrated in the following diagrams:
Figure 02_image011
When two groups form a ring with each other, it is preferable that the two groups are adjacent groups. Adjacent radicals in the sense of the present invention are radicals which are bonded to atoms which are directly bonded to one another or to the same atom. Preferably, the groups Ar 1 , Ar 3 represent identically or differently at each occurrence a condensed aryl group having 10 to 18 aromatic ring atoms. More preferably, the groups Ar 1 , Ar 3 represent identically or differently at each occurrence anthracene, naphthalene, phenanthrene, condensed tetraphenyl,
Figure 111113074-001
(chrysene), benzanthracene, triphenylene, pyrene, perylene, triphenylene, benzopyrene or allene (fluoranthene), each of which can be passed through one or more groups R V (in Ar 1 in the case of Ar 3 ) or substituted by RY (in the case of Ar 3 ) at any free position. Very preferably, the groups Ar 1 , Ar 3 represent an anthracene group, which may be substituted at any free position of Ar 1 by one or more groups R V or at any free position of Ar 3 by one or more groups RY any free position. Examples of suitable groups Ar and Ar are groups of formulas (Ar1-1) to (Ar1-11) as represented in the table below:
Figure 02_image013
wherein the groups of the equations (Ar-1) to (Ar-11) can be bonded to any position of the adjacent group and in the case of Ar 1 can be bonded to the group R V and in the case of Ar 3 Can be substituted by RY at each free position. Among the groups of formulas (Ar1-1) to (Ar1-11), the group of formula (Ar1-1) is preferred. Examples of very suitable groups Ar1 and Ar3 are groups of formulas (Ar1-1-1) to (Ar1-12-1) as represented in the table below:
Figure 02_image015
wherein the imaginary bond represents a bond to an adjacent group; and wherein the groups of formulas (Ar1-1-1) to (Ar1-12-1) may be substituted in each free position by the group R V in the case of Ar , or in the case of Ar 3 may be substituted at each free position by a group RY , wherein R V and RY have the same meaning as above. Among the groups of formulas (Ar1-1-1) to (Ar1-12-1), the group of formula (Ar1-1-1) is preferred. Preferably, in the compound of formula (H1), at least one group selected from X 1 to X 4 represents the group C-Ar X , wherein Ar X represents the group and group of formula (Ar X ) as defined above Groups X 5 to X 12 represent CR X or N. Preferably, the compound of formula (H1) is selected from compounds of formula (H1-A) to (H1-D):
Figure 02_image017
Figure 02_image019
Wherein these symbols have the same meaning as above. Preferably, E 1 , E 2 , E 3 and E 4 represent single bond, -C(R 0 ) 2 -, -Si(R 0 ) 2 -, -O-, -S- or -N(R 0 ). More preferably, one group selected from E 1 and E 3 represents a single bond and the other represents -C(R 0 ) 2 -, -Si(R 0 ) 2 -, -O-, -S- or - N(R 0 ) and a group selected from E 2 and E 4 represent single bonds and other groups represent -C(R 0 ) 2 -, -Si(R 0 ) 2 -, -O-, -S- or -N(R 0 ). More preferably, the compound of formula (H1) is selected from the compounds of the following formulae:
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027
Figure 02_image029
Figure 02_image031
wherein the symbols R X , Ar X have the same meanings as above and the groups E 1 , E 2 , E 3 and E 4 represent -BR 0 -, -C(R 0 ) identically or differently at each occurrence 2 -, -Si(R 0 ) 2 -, -C(=O)-, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 )- or - P(R 0 )-. Among the compounds of formulas (H1-A-1) to (H1-D-4), formulas (H1-A-1), (H1-B-1), (H1-C-1) and (H1-D The compound of -1) is preferable. Preferably, the group Ar X represents a group of formula (Ar X -1):
Figure 02_image033
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group R V . More preferably, the group Ar X represents a group of one of the following formulae:
Figure 02_image035
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group R V . Particularly preferably, the compound of formula (H1) is selected from the compounds of the following formulae:
Figure 02_image037
Figure 02_image039
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group R V . Preferably, R V , R X represent H, D, F, straight chain with 1 to 40 (preferably 1 to 20, more preferably 1 to 10) C atoms identically or differently at each occurrence Alkyl, alkoxy or alkylthio or branched or cyclic alkyl, alkoxy or alkylthio with 3 to 40 (preferably 3 to 20, more preferably 3 to 10) C atoms ( Each of them may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be replaced by RC=CR, C≡C, O or S and one or more of them Aromatic or heteroaromatic rings having 5 to 60 (preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18) aromatic ring atoms, each H atom may be replaced by D or F) system (which in each case may be substituted by one or more radicals R). More preferably, R V , R X represent H, D, F, straight chain with 1 to 20 (preferably 1 to 10, more preferably 1 to 6) C atoms at each occurrence identically or differently Alkyl or branched or cyclic alkyl having 3 to 20 (preferably 3 to 10, more preferably 3 to 6) C atoms (each of which may be substituted by one or more groups R), having Aromatic or heteroaromatic ring systems (which in each case may be substituted by one or more radicals R) of 5 to 40 (preferably 5 to 30, more preferably 5 to 18) aromatic ring atoms. More preferably, R X is H or D. More preferably, R V is H or D. Preferably, in the compound of formula (H2), a group selected from Z 1 to Z 4 represents the group C-Ar Z and a group selected from Z 5 to Z 8 represents the group C-Ar Z , wherein Ar Z represents a group of formula (Ar Z ) as defined above. Preferably, compound (H2) is selected from compounds of the following formula:
Figure 02_image041
Figure 02_image043
Figure 02_image045
Wherein these symbols have the same meaning as above. Among the compounds of formulas (H2-A) to (H2-J), compounds of formulas H2-A to H2-E, H2-H, and H2-I are preferred. Preferably, the group Ar Z represents a group of formula (Ar Z -1):
Figure 02_image047
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group RY . Preferably, the group Ar Z represents a group of one of the following formulas:
Figure 02_image049
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group RY . More preferably, compound (H2) is selected from compounds of the following formula:
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
Figure 02_image059
wherein the symbols and labels have the same meanings as above and wherein the anthracene group can be substituted at each free position by the group RY . Among the compounds of formulas (H2-A-1) to (H2-J-2), formulas H2-A-1 to H2-E-1, H2-H-1, H2-H2, H2-I2 and H2-I The compound of -1 is preferred. Preferably, RY , R Z represent H, D, F, straight chain with 1 to 40 (preferably 1 to 20, more preferably 1 to 10) C atoms identically or differently at each occurrence Alkyl, alkoxy or alkylthio or branched or cyclic alkyl, alkoxy or alkylthio with 3 to 40 (preferably 3 to 20, more preferably 3 to 10) C atoms ( Each of them may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be replaced by RC=CR, C≡C, O or S and one or more of them Aromatic or heteroaromatic rings having 5 to 60 (preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18) aromatic ring atoms, each H atom may be replaced by D or F) system (which in each case may be substituted by one or more radicals R). More preferably, RY , R Z represent H, D, F, straight chain with 1 to 20 (preferably 1 to 10, more preferably 1 to 6) C atoms identically or differently at each occurrence Alkyl or branched or cyclic alkyl having 3 to 20 (preferably 3 to 10, more preferably 3 to 6) C atoms (each of which may be substituted by one or more groups R), having Aromatic or heteroaromatic ring systems (which in each case may be substituted by one or more radicals R) of 5 to 40 (preferably 5 to 30, more preferably 5 to 18) aromatic ring atoms. More preferably, R Z represents H or D. More preferably, RY represents H or D. Preferably, the radicals Ar and Ar are at each occurrence identically or differently selected from aromatic or heteroaromatic ring systems having 5 to 30 (preferably 5 to 25) aromatic ring atoms, These may in each case be substituted by one or more radicals R. More preferably, the groups Ar 2 and Ar 4 are selected from the group consisting of phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirobis, naphthalene, phenanthrene, anthracene, triphenyl , allene combined fluoranthene (fluoranthene), thick tetraphenyl,
Figure 111113074-001
(chrysene), benzanthracene, triphenylene, pyrene, perylene, indole, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, indenocarbazole, indolocarbazole , pyridine, pyrimidine, pyridine, pyrimidine, trisulfone, quinolone, benzopyridine, benzopyridine, benzopyrimidine, benzimidazole and quinazoline, each of which may be substituted by one or more groups R ; wherein Ar 2 and Ar 4 can also be a combination of two or more of the previously cited groups. Particularly preferably, the groups Ar 2 and Ar 4 are selected from the group consisting of phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirobis, naphthalene, anthracene, phenanthrene, triphenyl , allene combined fluoranthene (fluoranthene), thick tetraphenyl,
Figure 111113074-001
(chrysene), benzanthracene, triphenylene, pyrene or perylene, dibenzofuran, carbazole and dibenzothiophene, each of which may be substituted at any free position by one or more groups R; and wherein Ar 2. Ar 4 can also be a combination of two or more of the aforementioned groups. Very particularly preferably, the groups Ar 2 and Ar 4 are selected from the group consisting of phenyl, biphenyl, terphenyl, tetraphenyl, fennel, spirobistilbene, naphthalene, anthracene, phenanthrene, biphenyl Benzene, allene and fluoranthene, dibenzofuran, carbazole and dibenzothiophene, each of which may be substituted at any free position by one or more groups R; and wherein Ar 2 , Ar 4 are also It may be a combination of two or more of the previously cited groups. Examples of suitable groups Ar and Ar are groups of formulas (Ar2-1) to (Ar2-27) as shown in the table below:
Figure 02_image061
Figure 02_image063
Figure 02_image065
wherein the dotted bond represents a bond to an adjacent group and wherein the group R has the same meaning as above; and wherein the group formulas of the equations (Ar2-1) to (Ar2-27) can be represented by The position is substituted with a group R having the same meaning as above. Among the groups of formulas (Ar2-1) to (Ar2-27), the formulas (Ar2-1), (Ar2-2), (Ar2-3), (Ar2-4), (Ar2-5), (Ar2 -8), (Ar2-18), (Ar2-19) groups are preferred. Groups of formula (Ar2-1), (Ar2-2), (Ar2-3), (Ar2-4), (Ar2-5) are very preferred. Preferably, the group ArS represents identically or differently at each occurrence phenyl, biphenyl, fluorine, spirodioxene, naphthalene, phenanthrene, anthracene, dibenzofuran, dibenzothiophene, carbazole, pyridine , pyrimidine, pyridine, pyridine, trisulfone, benzopyridine, benzopyridine, benzopyrimidine and quinazoline, each of which may be substituted with one or more groups R. Examples of suitable groups ArS are groups of formulas (ArS-1) to (ArS-26) as shown in the table below:
Figure 02_image067
Figure 02_image069
Wherein the dotted line bond represents the bond to the adjacent group in the formula (H1) or (H2); wherein the group of the equation (ArS-1) to (ArS-26) can be at each free position by having the same as defined above Substituted by groups R of the same meaning; and wherein each occurrence of the group E is identically or differently selected from -BR 0 -, -C(R 0 ) 2 -, -Si(R 0 ) 2 -, -C (=O)-, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 )-, and -P(R 0 )-, wherein R 0 has the same same definition. Among the groups of formulas (ArS-1) to (ArS-26), the groups of formulas (ArS-1), (ArS-2), (ArS-3), (ArS-11) and (ArS-12) is better. Groups of formula (ArS-1), (ArS-2), (ArS-3) are very preferred. Preferably, R represents H, D, F, linear alkyl having 1 to 10 C atoms or branched or cyclic alkyl having 3 to 10 C atoms identically or differently at each occurrence (each of which may be substituted by one or more groups R, where in each case one or more non-adjacent CH groups may be replaced by O or S and where one or more H atoms may be replaced by D or F substitution), or an aromatic or heteroaromatic ring system having 5 to 30 (preferably 6 to 18) aromatic ring atoms, which may in each case be substituted by one or more groups R, wherein Two adjacent groups R can together form an aliphatic or aromatic ring system, which can be substituted by one or more groups R; preferably, R represents H, D, F, CN, N(Ar) 2 , straight chain alkyl, alkoxy or alkylthio having 1 to 40 (preferably 1 to 20, more preferably 1 to 10) C atoms or 3 to 40 branched or cyclic alkyl, alkoxy or alkylthio groups (preferably 3 to 20, more preferably 3 to 10) C atoms (each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH groups may be replaced by R'C=CR', C≡C, O or S and wherein one or more H atoms may be replaced by D or F), or an aromatic or heteroaromatic ring system having 5 to 60 (preferably 5 to 40, more preferably 5 to 30, especially preferably 6 to 18) aromatic ring atoms, which in each case can be Or multiple groups R'substituted. Preferably, Ar is, at each occurrence, identical or different, aromatic having 5 to 40 (preferably 5 to 30, more preferably 5 to 25, very preferably 6 to 18) aromatic ring atoms or a heteroaromatic ring system, which in each case may also be substituted by one or more radicals R'; preferably, R' represents, identically or differently at each occurrence, H, D, F, Cl, Br , I, CN, straight chain alkyl having 1 to 10 C atoms or branched or cyclic alkyl having 3 to 10 C atoms (wherein each case one or more H atoms can be replaced by D or F replacement), or an aromatic or heteroaromatic ring system having 5 to 18 C atoms. The following compounds are examples of compounds of formula (H1):
Figure 02_image071
Figure 02_image073
Figure 02_image075
Figure 02_image077
Figure 02_image079
Figure 02_image081
Figure 02_image083
Figure 02_image085
Figure 02_image087
The following compounds are examples of compounds of formula (H2):
Figure 02_image089
Figure 02_image091
Figure 02_image093
Figure 02_image095
Figure 02_image097
Figure 02_image099
Figure 02_image101
According to a preferred embodiment, the composition comprises a compound of formula (H1), a compound of formula (H2) and at least one fluorescent emitter. The phrase "at least one fluorescent emitter" means "one, two, three, or more fluorescent emitters". According to a very preferred embodiment, the composition comprises a compound of formula (H1) as a first host material, a compound of formula (H2) as a second host material, and a fluorescent emitter as a dopant material. Preferably, the composition comprises at least one fluorescent emitter comprising at least one of the following groups: - comprising three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen - a bridged triarylamine; - a condensed aromatic or heteroaromatic ring system having at least 14 aromatic ring atoms; - indenoxene, indenoxeneamine or indenoxenediamine; - benzene benzoindenoxine, benzoindenoxineamine or benzoindenoxenediamine; - dibenzoindenoxene, dibenzoindenoxineamine or dibenzoindenoxinediamine; - containing at least 10 Indenofluorene of a condensed aryl group of two aromatic ring atoms; - bisindenoindenofluorene; - indenodibenzofuran; indenofluoreneamine or indenodiamine; 𠯤; or - a boron derivative. More preferably, the composition comprises at least one fluorescent emitter of one of the following formulas (E-1), (E-2), (E-3) or E-4) as described below:
Figure 02_image103
wherein Ar 10 , Ar 11 , Ar 12 are identically or differently at each occurrence an aromatic or heteroaromatic ring system having 6 to 60 aromatic ring atoms, which may in each case also be replaced by one or more The group R is substituted; the prerequisite for this is that at least one group Ar 10 , Ar 11 , Ar 12 is an aromatic or heteroaromatic ring system with 10 to 40 aromatic ring atoms and contains at least one of 2 to 4 each other Condensed aryl or heteroaryl groups consisting of condensed aromatic rings, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R; R has the same definition as above; and e is 1, 2 , 3 or 4; more preferably, e is 1;
Figure 02_image105
wherein Ar 20 , Ar 21 , Ar 22 are identically or differently at each occurrence an aryl or heteroaryl group having 6 to 30 aromatic ring atoms, which in each case may also be represented by one or more groups R substitution; E 20 at each occurrence is identically or differently selected from BR, C(R 0 ) 2 , Si(R 0 ) 2 , C=O, C=NR 0 , C=C(R 0 ) 2 , O, S, S=O, SO 2 , NR 0 , PR 0 , P(=O)R 0 or P(=S)R 0 ; wherein Ar 20 , Ar 21 and E 20 together form a five-membered ring or a six-membered ring Member ring, and Ar 21 , Ar 23 and E 20 together form a five-member ring or a six-member ring; R 0 represents H, D, F identically or differently at each occurrence, with 1 to 20 (preferably 1 to 20) 10) straight-chain alkyl groups with C atoms or branched or cyclic alkyl groups with 3 to 20 (preferably 3 to 10) C atoms (each of which may be substituted by one or more R groups, wherein in each case one or more non-adjacent CH groups can be replaced by O or S and wherein one or more H atoms can be replaced by D or F), or have 5 to 40 (preferably 5 to 30, more preferably 6 to 18), aromatic or heteroaromatic ring systems (which in each case may be substituted by one or more radicals R) of aromatic ring atoms, wherein two adjacent radicals The radicals R 0 may together form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R, R having the same definition as above; p, q are identically or differently 0 or 1 at each occurrence , whose prerequisites are p + q = 1; r is 1, 2 or 3;
Figure 02_image107
Wherein Ar 30 , Ar 31 , Ar 32 represent identically or differently each occurrence of substituted or unsubstituted aromatic ring atoms having 5 to 22 (preferably 5 to 18, more preferably 6 to 14) aromatic ring atoms. aryl or heteroaryl; E 30 represents B or N; E 31 , E 32 , E 33 represent O, S, C(R 0 ) 2 , C=O, C= S, C=NR 0 , C=C(R 0 ) 2 , Si(R 0 ) 2 , BR 0 , NR 0 , PR 0 , SO 2 , SeO 2 or a chemical bond, the prerequisite is that if E 30 is B, Then at least one of the groups E 31 , E 32 , E 33 represents NR 0 , and if E 30 is N, at least one of the groups E 31 , E 32 , E 33 represents BR 0 ; R 0 has Same definition as above; s, t, u are equally or differently 0 or 1 at each occurrence, with the prerequisite that s + t + u ≥ 1.
Figure 02_image109
Wherein Ar 40 , Ar 41 , Ar 42 represent identically or differently each occurrence of substituted or unsubstituted aromatic ring atoms having 5 to 22 (preferably 5 to 18, more preferably 6 to 14) aromatic ring atoms. Aryl or heteroaryl; E 41 , E 42 , E 43 represent O, S, C(R 0 ) 2 , C=O, C=S, C=NR 0 , C=C(R 0 ) 2 , Si(R 0 ) 2 , BR 0 , NR 0 , PR 0 , SO 2 , SeO 2 or a chemical bond, the prerequisite being at least one of the groups E 41 , E 42 , E 43 One is present and represents a chemical bond; R 0 has the same definition as above; i, g, h are identically or differently 0 or 1 at each occurrence, with the prerequisite that i + g + h ≥ 1. Preferably, the fluorescent emitter of formula (E-1) comprises at least one group Ar 10 , Ar 11 or Ar 12 , preferably Ar 10 , which is selected from formulas (Ar 10 -1) to (Ar 10 -24) group:
Figure 02_image111
Figure 02_image113
Figure 02_image115
wherein the groups Ar 10 -1 to Ar 10 -24 may be substituted at all free positions by one or more groups R; and wherein E 10 at each occurrence is identically or differently selected from BR 0 , C(R 0 ) 2 , Si(R 0 ) 2 , C=O, C=NR 0 , C=C(R 0 ) 2 , O, S, S=O, SO 2 , NR 0 , PR 0 , P(=O) R 0 or P(=S)R 0 , preferably E 10 is C(R 0 ) 2 ; wherein R 0 has the same definition as above; E 11 is selected from C= O, O, S, S=O or SO 2 , preferably O or S, more preferably O; and Ar 13 is, identically or differently in each occurrence, an aromatic having 5 to 60 aromatic ring atoms or heteroaromatic ring systems, which in each case may also be substituted by one or more radicals R. According to a preferred embodiment, the emitter of formula (E-1) comprises a group Ar 10 , which is selected from groups of formulas (Ar 10 -15) to (Ar 10 -22), wherein d is preferably equal to 1 And preferably at least one of the groups Ar 11 and Ar 12 is selected from the groups of formulas (Ar 10 -15) to (Ar 10 -22). According to a very good embodiment, the light-emitting system of formula (E-1) is selected from the light-emitting bodies of formulas (E-1-1) to (E-1-6),
Figure 02_image117
Figure 02_image119
wherein these symbols have the same meanings as above and wherein: f is 0, 1 or 2; and the benzene rings represented in the compounds of formulas (E-1-1) to (E-1-6) above All free positions are substituted with one or more groups R. Particularly preferably, the compound of formula (E-1) is selected from the compounds of formula (E-1-1-A) to (E-1-6-A),
Figure 02_image121
Figure 02_image123
Figure 02_image125
Wherein these symbols and labels have the same meaning as above and wherein the above-mentioned benzene rings represented in the compounds of formulas (E-1-1-A) to (E-1-6-A) can be passed through at all free positions One or more groups R are substituted. Preferably, the fluorescent light emitting system of formula (E-2) is selected from the fluorescent light emitters of formula (E-2-1) to (E-2-43),
Figure 02_image127
Figure 02_image129
Figure 02_image131
Figure 02_image133
Figure 02_image135
Figure 02_image137
wherein the groups of formulas (E-2-1) to (E-2-43) may be substituted at all free positions by one or more groups R; and wherein E 20 has the same definition as above. Preferably, E 20 is C(R 0 ) 2 . The compound of formula (E-2) is preferably selected from compounds of formulas (E-2-32) to (E-2-43). More preferably, the compound of formula (E-2) is selected from compounds (E-2-32-A) to (E-2-43-A):
Figure 02_image139
Figure 02_image141
Figure 02_image143
wherein these symbols have the same meanings as above and wherein the above-mentioned benzene and naphthalene rings represented in the compounds of formulas (E-2-32-A) to (E-2-43-A) can be passed through at all free positions One or more groups R are substituted. Preferably, the fluorescent light emitting system of formula (E-3) is selected from the fluorescent light emitters of formula (E-3-1),
Figure 02_image145
Wherein these symbols and labels have the same meanings as above. More preferably, the fluorescent light emitting system of formula (E-3) is selected from the fluorescent light emitters of formula (E-3-2),
Figure 02_image147
wherein the symbols E30 to E33 have the same meaning as above; wherein t is 0 or 1, wherein when t is 0, the group E32 is absent and the group R10 is present, which replaces the bond of E32 ; and wherein R 10 at each occurrence identically or differently represents H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) 2 , S(= O)Ar, S(=O) 2 Ar, N(R') 2 , N(Ar) 2 , NO 2 , Si(R') 3 , B(OR') 2 , OSO 2 R', with 1 to Straight-chain alkyl, alkoxy or alkylthio (thioalkyl) having 40 C atoms or branched or cyclic alkyl, alkoxy or alkylthio having 3 to 40 C atoms (they can each be passed through One or more groups R' are substituted, wherein in each case one or more non-adjacent CH 2 groups can be replaced by R'C=CR', C≡C, Si(R') 2 , Ge(R ') 2 , Sn(R') 2 , C=O, C=S, C=Se, P(=O)(R'), SO, SO 2 , O, S or CONR' substitution and one or more of them H atoms may be replaced by D, F, Cl, Br, I, CN or NO), aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms (which in each case may be replaced by one or a plurality of groups R'substituted), or an aryloxy group having 5 to 60 aromatic ring atoms (which may be substituted by one or more groups R'); where two adjacent substituents R 10 can be together An aliphatic or aromatic ring system is formed, which may be substituted by one or more radicals R'; wherein R' has the same definition as above. Even more preferably, the fluorescent light emitting system of formula (E-3) is selected from the fluorescent light emitters of formula (E-3-3) and (E-3-4),
Figure 02_image149
Wherein these symbols and labels have the same meanings as above. Preferably, the fluorescent light-emitting system of formula (E-4) is selected from the fluorescent emitters of formula (E-4-1) or E-4-2),
Figure 02_image151
where E 41 and E 42 represent O, S, C(R 0 ) 2 , C=O, C=S, C=NR 0 , C=C(R 0 ) 2 , Si (R 0 ) 2 , BR 0 , NR 0 , PR 0 , SO 2 , SeO 2 or a chemical bond, wherein E 41 is preferably a bond; R 20 represents H, D, F, Cl identically or differently at each occurrence , Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R') 2 , N( Ar) 2 , NO 2 , Si(R') 3 , B(OR') 2 , OSO 2 R', linear alkyl, alkoxy or thioalkyl having 1 to 40 C atoms or Branched or cyclic alkyl, alkoxy or alkylthio groups having 3 to 40 C atoms (each of which may be substituted by one or more radicals R', wherein in each case one or more non-phase The adjacent CH 2 group can be changed by R'C=CR', C≡C, Si(R') 2 , Ge(R') 2 , Sn(R') 2 , C=O, C=S, C= Se, P(=O)(R'), SO, SO 2 , O, S or CONR' replacement and one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 ) , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms (which in each case may be substituted by one or more radicals R'), or an aromatic ring system having 5 to 60 aromatic ring atoms Oxygen (which may be substituted by one or more groups R'); where two adjacent substituents R may together form an aliphatic or aromatic ring system which may be substituted by one or more groups R'; wherein R' has the same definition as above; g is 0 or 1. More preferably, the fluorescent light-emitting system of formula (E-4) is selected from the fluorescent emitters of formula (E-4-1-A) or (E-4-2-A),
Figure 02_image153
Wherein these symbols have the same meaning as above. According to a preferred embodiment, the fluorescent emitter of formula (E-1), (E-2), (E-3) or (E-4) comprises a group RS, wherein the group RS is: - selected Branched chain or cyclic alkyl represented by the following general formula of the radical of formula (RS-a),
Figure 02_image155
Wherein R 22 , R 23 , R 24 are identically or differently selected from each occurrence of H, straight chain alkyl having 1 to 10 carbon atoms, or branched or cyclic having 3 to 10 carbon atoms Alkyl, wherein each of the aforementioned groups may be substituted by one or more groups R 25 , and wherein two or all of the groups R 22 , R 23 , R 24 may be connected to to form a (poly)cyclic alkyl group, which may be substituted by one or more groups R 25 ; R 25 at each occurrence is identically or differently selected from linear alkyl groups having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms; with the proviso that at each occurrence at least one of the groups R 22 , R 23 and R 24 is not H, with the proviso that At each occurrence, all groups R 22 , R 23 and R 24 together have at least 4 carbon atoms with the proviso that at each occurrence, if two of the groups R 22 , R 23 , R 24 are H, the remaining groups are not linear; or - selected from branched or cyclic alkoxy groups represented by the following general formula (RS-b)
Figure 02_image157
Wherein R 26 , R 27 , R 28 are identically or differently selected from each occurrence of H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic group having 3 to 10 carbon atoms Alkyl, wherein each of the aforementioned groups may be substituted by one or more groups R 25 as defined above, and wherein two or all of the groups R 26 , R 27 , R 28 are R 26 , R 27 , R 28 may be attached to form a (poly)cyclic alkyl group which may be substituted by one or more groups R 25 as defined above; with the proviso that in each occurrence of the groups R 26 , R 27 and R 28 Only one of them can be H; - selected from the aralkyl group represented by the following general formula (RS-c)
Figure 02_image159
Wherein R 29 , R 30 , R 31 are identically or differently selected from each occurrence of H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic group having 3 to 10 carbon atoms Alkyl, wherein the aforementioned groups may each be substituted by one or more groups R 32 , or aromatic ring systems having 6 to 30 aromatic ring atoms which may in each case be substituted by one or more groups R 32 substituted, and wherein two or all of the groups R 29 , R 30 , R 31 can be connected to form a (poly)cyclic alkyl or aromatic ring system, each of which can be connected via one or more groups R 32 is substituted; R 32 is identically or differently selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, or having 6 Aromatic ring systems of up to 24 aromatic ring atoms; provided that at each occurrence at least one of the groups R 29 , R 30 and R 31 is not H, and at each occurrence the group At least one of the groups R 29 , R 30 and R 31 is or comprises an aromatic ring system having at least 6 aromatic ring atoms; - selected from the aromatic ring systems represented by the following general formula (RS-d)
Figure 02_image161
wherein R40 to R44 are identically or differently selected from each occurrence of H, linear alkyl having 1 to 10 carbon atoms, or branched or cyclic alkyl having 3 to 10 carbon atoms, wherein the aforementioned radicals may each be substituted by one or more radicals R 32 , or aromatic ring systems having 6 to 30 aromatic ring atoms which may in each case be substituted by one or more radicals R 32 , and wherein two or more of the groups R 40 to R 44 may be linked to form a (poly)cyclic alkyl or aromatic ring system, each of which may be substituted by one or more groups R 32 as defined above or - selected from a group of formula (RS-e),
Figure 02_image163
Wherein the dotted bond in the formula (RS-e) represents the bond to the fluorescent emitter, wherein Ar 50 , Ar 51 represent the same or different aromatic or aromatic ring atoms having 5 to 60 aromatic ring atoms at each occurrence. Heteroaromatic ring systems, which may in each case be substituted by one or more radicals R; and wherein m is an integer selected from 1 to 10. Preferably, the index m in the group of formula (RS-e) is an integer selected from 1 to 6, very preferably selected from 1 to 4. Preferably, wherein Ar 50 , Ar 51 represent identically or differently each occurrence of an aromatic or heteroaryl having 5 to 40 (preferably 5 to 30, more preferably 6 to 18) aromatic ring atoms Acyclic ring systems which may in each case be substituted by one or more radicals R. More preferably, Ar 50 and Ar 51 are selected from phenyl, biphenyl, terphenyl, quaterphenyl, stilbene, spirobistilbene, naphthalene, anthracene, phenanthrene, and triphenylene , allene fluoranthene, dibenzofuran, carbazole and dibenzothiophene, which may in each case be substituted by one or more radicals R. Very preferably, at least one group Ar 50 or Ar 51 is fluorene, which may be substituted by one or more groups R. More particularly, it is preferred that at least one group Ar 50 represents a group of formula (Ar50-2) and/or at least one group Ar 51 represents a group of formula (Ar51-2),
Figure 02_image165
Wherein the dotted line bond in the formula (Ar50-2) represents the bond to the fluorescent light emitter and to the group Ar 50 or Ar 51 ; and the dotted line bond in the formula (Ar51-2) represents the bond to the Ar 50 ; E 4 is selected from -C(R 0a ) 2- , -Si(R 0a ) 2- , -O-, -S- or -N(R 0a )-, preferably -C(R 0a ) 2 ; R 0a represents H, D, F, CN, straight-chain alkyl having 1 to 40 (preferably 1 to 20, more preferably 1 to 10) C atoms or having 3 to 10 C atoms identically or differently at each occurrence 40 (preferably 3 to 20, more preferably 3 to 10) branched or cyclic alkyl groups of C atoms (each of which may be substituted by one or more groups R), having 5 to 60 (more Preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18) aromatic or heteroaromatic ring systems of aromatic ring atoms (which in each case may be substituted by one or more radicals R) ; where two adjacent substituents R 0a can form a monocyclic or polycyclic aliphatic ring system or aromatic ring system, which can be substituted by one or more groups R, which have the same meaning as above; and The groups of the formulas (Ar50-2) and (Ar51-2) may be substituted at each free position by a group R which has the same meaning as above. The group RS is preferably located in a position where RS replaces R, R 0 or R'. Examples of fluorescent emitters that can be used in compositions comprising compounds of the formulas (H1) and (H2) are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic
Figure 111113074-001
Amine (chrysenamine) or aromatic
Figure 111113074-001
diamine. Aromatic anthracenamine means a compound in which one diarylamine group is directly bonded to an anthracenyl group (preferably at the 9-position). Aromatic anthracene diamine means a compound in which two diarylamine groups are directly bonded to an anthracene group (preferably at the 9,10-position). Aromatic pyreneamine, pyrenediamine,
Figure 111113074-001
Amines and
Figure 111113074-001
Diamines are defined analogously thereto, wherein the diarylamine group is preferably bonded to the 1-position or the 1,6-position of pyrene. Further preferred emitters are bridged triarylamines (eg according to WO 2019/111971, WO 2019/240251 and WO 2020/067290). Further preferred emitters are indenoxeneamine or indenoxenediamine (eg according to WO 2006/108497 or WO 2006/122630), benzindenoxeneamine or benzoindenoxenediamine (eg according to WO 2008/ 006449), and dibenzoindenoxeneamine or dibenzoindenoxenediamine (for example according to WO 2007/140847), and the indenoxene derivatives comprising condensed aryl groups disclosed in WO 2010/012328. Yet other preferred emitters are benzanthracene derivatives as disclosed in WO 2015/158409, anthracene derivatives as disclosed in WO 2017/036573, terpenes linked via heteroaryl groups as in WO 2016/150544 Polymers or phenanthane derivatives as disclosed in WO 2017/028940 and WO 2017/028941. Also preferred are pyrenarylamines disclosed in WO 2012/048780 and WO 2013/185871. Also preferred are the benzoindenotermines disclosed in WO 2014/037077, the benzoindenotermines disclosed in WO 2014/106522 and the ones disclosed in WO 2014/111269 or WO 2017/036574, WO 2018/007421 of indene and fennel. Preferably also as disclosed in WO 2018/095888, WO 2018/095940, WO 2019/076789, WO 2019/170572 and unpublished applications PCT/EP2019/072697, PCT/EP2019/072670 and PCT/EP2019/072662 Emitters containing dibenzofuran or indenodibenzofuran moieties. Also preferred are boron derivatives as disclosed in for example WO 2015/102118, CN108409769, CN107266484, WO2017195669, US2018069182 and unpublished applications EP 19168728.4, EP 19199326.0 and EP 19208643.7. In the context of the present invention, very suitable fluorescent emitters are the indenoxene derivatives disclosed in WO 2018/007421 and the dibenzofuran derivatives disclosed in WO 2019/076789. Examples of preferred fluorescent light-emitting compounds that can be used in compositions comprising compounds of formula (H1) and (H2) are described in the table below:
Figure 02_image167
Figure 02_image169
Figure 02_image171
Figure 02_image173
Figure 02_image175
Figure 02_image177
Figure 02_image179
Figure 02_image181
Figure 02_image183
Figure 02_image185
Figure 02_image187
Figure 02_image189
Figure 02_image191
Figure 02_image193
Figure 02_image195
Figure 02_image197
Figure 02_image199
Figure 02_image201
Figure 02_image203
Figure 02_image205
Figure 02_image207
Figure 02_image209
Figure 02_image211
Figure 02_image213
Figure 02_image215
Figure 02_image217
Figure 02_image219
Figure 02_image221
Figure 02_image223
Figure 02_image225
Figure 02_image227
Figure 02_image229
Figure 02_image231
Figure 02_image233
Figure 02_image235
Figure 02_image237
Figure 02_image239
Figure 02_image241
Figure 02_image243
Figure 02_image245
Figure 02_image247
Figure 02_image249
Figure 02_image251
Figure 02_image253
Figure 02_image255
Figure 02_image257
Figure 02_image259
Figure 02_image261
According to the invention, the compound of formula (H1) and the compound of formula (H2) are present together in a composition, preferably in a homogeneous mixture. Preferably, the compound of formula (H1) is present in the composition at a ratio of 1-99%, preferably 10-90%, more preferably 20-80%, particularly preferably 30-75%, very particularly preferably 35-70% middle. Preferably, the compound of formula (H2) is present in the ratio of 1-99%, preferably 10-90%, more preferably 20-80%, particularly preferably 25-70%, very particularly preferably 30-60%. In the composition of the invention. According to a preferred embodiment, the composition according to the invention additionally comprises at least one fluorescent emitter. In this case, it is preferred that the fluorescent light-emitting system is present in the composition in a proportion between 0.1 and 50.0%, preferably between 0.5 and 20.0%, especially between 1.0 and 10.0%. For the purposes of this application, ratio specifications in % mean % by volume if the compound is applied from the gas phase and % by weight if the compound is applied from solution. In order to process the compounds according to the invention from the liquid phase, for example by coating methods such as spin coating or by printing methods, formulations of the compositions according to the invention are required. Such formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it is preferred to use a mixture of two or more solvents. The solvent is preferably selected from organic and inorganic solvents, more preferably organic solvents. The solvent is very preferably selected from hydrocarbons, alcohols, esters, ethers, ketones and amines. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, trimethylbenzene, tetralin, veratrole, THF, methyl-THF , THP, chlorobenzene, dioxane, phenoxytoluene (especially 3-phenoxytoluene), (-)-fenzone, 1,2,3,5-tetramethylbenzene, 1,2,4 ,5-tetramethylbenzene, 1-methylnaphthalene, 1-ethylnaphthalene, decylbenzene, phenylnaphthalene, menthyl isovalerate, p-cresyl isobutyrate, cyclohexal hexanoate ), ethyl p-toluate, ethyl o-toluate, ethyl m-toluate, decahydronaphthalene, ethyl 2-methoxybenzoate, dibutylaniline, dicyclohexyl ketone, isosorbide dimethyl ether, decahydronaphthalene, 2-methylbiphenyl, ethyl octanoate, octyl octanoate, diethyl sebacate, 3,3-dimethylbiphenyl, 1,4-dimethylnaphthalene, 2,2 '-Dimethylbiphenyl, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-bis Methylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexyl Benzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indanes, NMP, p-cymene, phenylethyl ether, 1,4-diisopropylbenzene, benzhydryl ether , Diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether , tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or a mixture of such solvents. The present invention therefore also relates to a formulation comprising a compound of formula (H1 ) and a compound of formula (H2) according to the invention and at least one solvent. The solvent may be one of the above solvents or a mixture of these solvents. The proportion of organic solvents in the formulations according to the invention is preferably at least 60% by weight, preferably at least 70% by weight and better still at least 80% by weight, based on the total weight of the formulation. The formulations according to the invention can be used to produce one-layer or multi-layer structures, wherein organic functional materials can be present in the layers, depending on the requirements for the production of preferred electronic or optoelectronic components, such as OLEDs. The formulations of the invention can preferably be used to form a functional layer comprising a composition according to the invention on a substrate or on one of the layers applied to a substrate. Yet another object of the invention is a method of manufacturing an electronic device, wherein at least one layer is obtained from applying the formulation of the invention. Preferably, the formulation according to the invention is applied to a substrate or another layer and then dried. The functional layers obtained from the formulations according to the invention can be coated, for example, by flood coating, dip coating, spray coating, spin coating, screen printing, letterpress printing, gravure printing, rotary printing, roll coating, quick-dry printing ( flexographic printing), lithographic printing or nozzle printing, preferably inkjet printing on the substrate or one of the layers applied to the substrate. After the formulation according to the invention has been applied to the substrate or the applied functional layer, a drying step may be carried out in order to remove the solvent. Preferably, the drying step comprises vacuum drying, which is preferably followed by annealing of the layer. Vacuum drying can preferably be carried out here at a pressure in the range from 10 −7 mbar to 1 bar, particularly preferably at a pressure in the range from 10 −6 mbar to 1 bar. Vacuum drying is preferably performed at a temperature ranging from 10 to 40°C, more preferably 15 to 30°C. The vacuum drying step is preferably followed by thermal annealing of the layers. Thermal annealing of the layers is preferably carried out at a temperature of from 120°C to 180°C, preferably from 130°C to 170°C, more preferably from 140°C to 160°C. Accordingly, the present invention relates to a method of manufacturing an electronic device comprising at least one layer comprising a composition according to the invention, wherein the method comprises the following steps: a) preparing a formulation according to the invention; b) combining the steps The formulation prepared in a) is applied on a substrate or on another layer to form a layer comprising the composition according to the invention; c) drying the layer to remove the solvent. Preferably, in step b), the formulation is produced by processing from the liquid phase, more preferably by a coating method or by a printing method, very preferably by a printing method, particularly preferably by an inkjet printing method apply. Another object of the invention is an electronic device comprising an anode, a cathode and at least one functional layer interposed therebetween, wherein this functional layer comprises a composition according to the invention. Preferably, the at least one functional layer comprising the composition according to the invention is a light-emitting layer. The electronic device is preferably selected from organic electroluminescent devices (OLEDs), organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, organic dye-sensitized solar cells, organic optical Detectors, organic photoreceptors, organic field quenchers, light emitting electrochemical cells, organic laser diodes and organic plasmon emitting devices. More preferably, the electronic device is an organic electroluminescent device (OLED). An organic electroluminescent device comprises a cathode, an anode and at least one emitting layer comprising a composition according to the invention. In addition to these layers, the organic electroluminescent device may also comprise further layers, such as in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers, A sub-blocking layer, an electron blocking layer, and/or a charge generating layer. It is likewise possible to introduce an intermediate layer having, for example, an exciton-blocking function between two emitting layers. However, it should be noted that each of these layers does not necessarily have to be present. The organic electroluminescent device here can comprise an emitting layer or a plurality of emitting layers. If several emitting layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in white emission overall, ie using various emitting compounds capable of fluorescence or phosphorescence for emission layer. Particularly preferred are systems with three emitting layers, the three layers exhibiting blue, green and orange or red emission (for the basic structure see eg WO 2005/011013). These may be fluorescent or phosphorescent emitting layers or hybrid systems in which fluorescent and phosphorescent emitting layers are combined with one another. The electronic device concerned may comprise a single light-emitting layer comprising the composition according to the invention, or it may comprise two or more light-emitting layers. Compositions according to the invention may comprise one or more other matrix materials. Preferred further matrix materials are selected from the following classes: oligoarylene (eg 2,2',7,7'-tetraphenylspirobistilbene or dinaphthylanthracene according to EP 676461), in particular are oligoarylene containing condensed aromatic groups, oligoarylenevinylene (for example DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (for example according to WO 2004/081017), hole-conducting compounds (for example according to WO 2004/058911), electron-conducting compounds, especially ketones, phosphine oxides, phosphine, etc. (for example according to WO 2005/084081 and WO 2005/084082), atropine Isomers (eg according to WO 2006/048268), boronic acid derivatives (eg according to WO 2006/117052) or benzanthracene (eg according to WO 2008/145239). Particularly preferred host materials are selected from the following classes: oligoarylene, oligoarylene vinylene, ketone, oxidized Phosphine and Phosphine. Very particularly preferred matrix materials are selected from the class of oligoarylenes comprising anthracene, benzanthracene, triphenanthrene and/or pyrene or atropisomers of these compounds. An oligoaryl group in the sense of the present invention means a compound in which at least three aryl groups or aryl groups are bonded to one another. Generally preferred classes of materials for use as corresponding functional materials in organic electroluminescent devices according to the invention are indicated below. Suitable charge transport materials, such as can be used in hole injection or hole transport layers or electron blocking layers of electronic devices according to the invention or in electron transport layers are, for example, Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010 or other materials used in these layers according to the prior art. Materials which can be used for the electron-transport layer are all materials which have been used according to the prior art as electron-transport materials in the electron-transport layer. Particularly suitable are aluminum complexes (for example, Alq 3 ), zirconium complexes (for example, Zrq 4 ), lithium complexes (for example LiQ), benzimidazole derivatives, trioxane derivatives, pyrimidine derivatives, Pyridine derivatives, pyridine derivatives, quinoline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives. Furthermore, suitable materials are derivatives of the aforementioned compounds, as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300. Preferred hole transport materials which can be used in the hole transport layer, hole injection layer or electron blocking layer in the electroluminescent device according to the invention are indenoximide derivatives (for example according to WO 06/122630 or WO 06 /100896), amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (eg according to WO 01/049806), amine derivatives comprising condensed aromatic rings (eg according to US 5,061,569), WO 95/ Amine derivatives disclosed in 09147, monobenzindenoxylamine (eg according to WO 08/006449), dibenzoindenoxylamine (eg according to WO 07/140847), spirobistilamine (eg according to WO 2012 /034627 or WO 2013/120577), stilamine (eg according to applications EP 2875092, EP 2875699 and EP 2875004), spirodibenzopyranylamine (eg according to WO 2013/083216) and dihydroacridine derivatives (eg According to WO 2012/150001). The compounds according to the invention can also be used as hole transport materials. The cathode of an organic electroluminescent device preferably comprises a metal with a low work function, a metal alloy or a multilayer structure comprising various metals, such as, for example, alkaline earth metals, alkali metals, main group metals or lanthanides (e.g. Ca, Ba, Mg , Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys comprising alkali metals or alkaline earth metals and silver, for example alloys comprising magnesium and silver. In the case of multilayer structures, besides these metals, other metals with higher work functions can also be used, such as, for example, Ag or Al, in which case a combination of metals, such as, for example, Ca/Ag is usually used , Mg/Ag or Ag/Ag. It may also be advantageous to introduce a thin interlayer of a material with a high dielectric constant between the metal cathode and the organic semiconductor. Suitable for this purpose are, for example, alkali metal fluorides or alkaline earth metal fluorides, but corresponding oxides or carbonates (such as LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc. ) is also suitable. Additionally, lithium quinolinate (LiQ) can be used for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm. The anode preferably comprises a material with a high work function. The anode preferably has a work function greater than 4.5 eV versus vacuum. Suitable for this purpose are on the one hand metals with a high redox potential, such as, for example, Ag, Pt or Au. On the other hand, metal/metal oxide electrodes such as Al/Ni/ NiOx , Al/ PtOx may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order to facilitate illumination of organic materials (organic solar cells) or coupling-out of light (OLEDs, O-lasers). Preferred anode materials here are conductive mixed metal oxides. Particularly preferred is indium tin oxide (ITO) or indium zinc oxide (IZO). In addition, conductive doped organic materials are preferred, especially conductive doped polymers. The device is structured appropriately (depending on the application), equipped with joints and finally sealed, since the lifetime of the device according to the invention is shortened in the presence of water and/or air. In a preferred embodiment, the organic electroluminescent device according to the invention is characterized in that one or more layers are coated by means of a sublimation method, wherein the materials are applied in a vacuum sublimation unit at temperatures below 10-5 mbar, more Preferably applied by vapor deposition at an initial pressure below 10-6 mbar. However, the initial pressure can also be even lower here, for example below 10-7 mbar. Also preferred is an organic electroluminescent device characterized in that one or more layers are coated by the OVPD (Organic Vapor Phase Deposition) method or supplemented by a carrier-gas sublimation method, wherein the materials are between 10 -5 mm applied at a pressure between bar and 1 bar. A particular example of this method is the OVJP (Organic Vapor Jet Printing) method, in which the materials are applied directly through nozzles and thus structured (e.g. MS Arnold et al. , Appl. Phys. Lett. 2008 , 92 , 053301 ). Further preferred is an organic electroluminescent device characterized in that one or more layers are formed such as, for example, by spin coating or by any desired printing method, such as, for example, screen printing, quick-dry printing, nozzle printing or lithography Printing, but particularly preferably LITI (Light Induced Thermography, Thermal Transfer Printing) or inkjet printing) from solution. Soluble compounds of formula (I) are required for this purpose. High solubility can be achieved through appropriate substitution of these compounds. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more other layers are applied by vapor deposition. Thus, for example, it is possible to apply the emitting layer from solution and the electron-transporting layer by vapor deposition. These methods are generally known to the person skilled in the art and can be applied by the person skilled in the art without an inventive step to organic electroluminescent devices comprising the compounds according to the invention. According to the invention, electronic devices comprising one or more compounds according to the invention can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications such as phototherapy. The invention will now be explained in more detail with the following examples, without wishing to limit the invention thereby.

合成例 a) 主體H1 式(H1)的主體之合成為熟習此項技術者已知且描述於例如WO 2010/151006和WO 2020/089138中。以下描述其他合成例： A1 的合成

Figure 02_image263
在氬氛圍下，將烘箱乾燥的燒瓶配備磁力攪拌棒、1 (2417686-30-5) (13.0 g，36.9 mmol，1.0 equiv.)、 2(2377545-66-7) (18.4 g，54 mmol)、參(二苯亞甲基丙酮)二鈀(1.3 g，1.4 mmol)、SPhos (1.16 g，2.8 mmol)和氟化鉀(5.3 g，92.3 mmol)。添加甲苯(150 mL)、1,4-二㗁烷(150 mL)和水(150 mL)並將混合物回流過夜。將原產物藉由管柱層析和昇華純化。將所需的產物分離為無色固體(5.2 g，9.1 mmol，25%)。 下列化合物可以類似的方式合成：
Figure 02_image265
Figure 02_image267
A6 的合成
Figure 02_image269
將5 g (8.9 mmol) 2417297-74-4 溶解在 100 ml 甲苯-d8中。在室溫下滴加4.7 ml (0.05 mol)三氟甲磺酸。溶液變黑並在室溫下攪拌2.5小時。藉由保持溫度恆定，添加20 ml 氧化氘。溶液變為橙色。16小時後，添加50 ml的磷酸鉀水溶液和50 ml甲苯。將有機相用水洗滌並用硫酸鎂乾燥。將粗製材料用二氧化矽(甲苯)過濾。將產物藉由管柱層析(二氧化矽，甲苯/庚烷)和甲苯/庚烷之結晶純化。藉由昇華移除剩餘的溶劑。藉由NMR光譜和LC-MS獲得氘化等級。產量：2.8 g (4.8 mmol；54%) b) 主體H2 式(H2)的主體之合成為熟習此項技術者已知且描述於例如EP20187118.3、EP20187122.5、KR20170096860和CN109867646中。以下描述其他合成例： 化合物 B1 的合成：
Figure 02_image271
將15 g (38 mmol) 三氟甲磺酸8-溴-二苯并呋喃-1-基酯、43.3 g (114 mmol) 4,4,5,5-四甲基-2-(10-苯基-蒽-9-基)-[1,3,2]二氧雜環戊硼烷(dioxaborolane)、35.5 g (167 mmol)磷酸鉀和1.6 g (1,9 mmol) XPhos Palladacycle Gen. 3溶解在450 ml THF/水(2：1)中。將混合物在90℃下攪拌16小時。冷卻至室溫後，添加300 ml乙醇並將混合物攪拌一小時。濾出沈澱物並用乙醇洗滌。將原料溶解在甲苯中並通過過濾塞(二氧化矽，甲苯)過濾。所得材料為黃色固體，將其藉由甲苯/庚烷之多次結晶進一步純化以產生淡黃色固體(HPLC＞99.9)。藉由昇華(在330℃下10 -5巴)移除剩餘的溶劑。 產量：15.2 g (22.6 mmol；60%) 下列化合物可以類似的方式合成：
Figure 02_image273
E1-B3 的合成
Figure 02_image275
將8.4 g (30 mmol) 2173554-83-9、15.2 g (40 mmol) 4,4,5,5-四甲基-2-(10-苯基-蒽-9-基)-[1,3,2]二氧雜環戊硼烷(dioxaborolane)、15.9 g ( 75 mmol)磷酸鉀和1.3 g (1.5 mmol) XPhos Palladacycle Gen. 3溶解在400 ml THF/水(2：1)中。將混合物在90℃下攪拌16小時。冷卻至室溫後，添加300 ml乙醇並將混合物攪拌一小時。濾出沈澱物並用乙醇洗滌。將原料溶解在甲苯中並通過過濾塞(二氧化矽，甲苯)過濾。所得材料為固體，將其藉由管柱層析和甲苯/庚烷之結晶進一步純化(HPLC＞98.0)。產量：4.2 g (9.3 mmol；31%)。 B3 的合成
Figure 02_image277
將4.1 g (9.1 mmol) E-H2-3、5.3 g (15 mmol) CAS 870119-38-3、5.3 g (25 mmol)磷酸鉀和0.25 g (0.3 mmol) XPhos Palladacycle Gen. 3溶解在300 ml THF/水(2：1)中。將混合物在90℃下攪拌16小時。冷卻至室溫後，添加300 ml乙醇並將混合物攪拌一小時。濾出沈澱物並用乙醇洗滌。將原料溶解在甲苯中並通過過濾塞(二氧化矽，甲苯)過濾。所得材料為固體，將其藉由管柱層析和甲苯/庚烷之結晶進一步純化(HPLC＞99.9)。藉由昇華(在340℃下10 -5巴)移除剩餘的溶劑。產量：0.96 g (2.1 mmol；23%) 裝置例a)   薄膜和裝置的製備 使用超音波將覆蓋有預結構化的ITO (50 nm)和空白材料之玻璃基板在去離子水中清潔。下文中，基板係使用空氣槍乾燥及接著在加熱板上於225℃下退火2小時。 所有下列方法步驟係以黃光進行。 下列層順序係顯示於圖4a和4b中。 將電洞注入層(HIL)以20 nm的厚度噴墨印刷於基板上，並在真空下乾燥。為此，HIL油墨具有6 g/l的固體濃度。接著將HIL在220℃下退火30分鐘。HIL的噴墨印刷和退火是在空氣中進行。作為HIL材料，將電洞傳輸性可交聯的聚合物和經p-摻雜的鹽溶解於3-苯氧基甲苯中。這些材料係描述於例如(i.e.)WO2016/107668、WO2013/081052和EP2325190中。 在HIL的頂部，在環境條件下噴墨印刷電洞傳輸層，在真空中乾燥及於氬氛圍中在220℃下退火30分鐘。電洞傳輸層為表1中所示結構的聚合物(HTM1)，其係根據WO2013156130合成或聚合物HTM2(表1)，其係根據 WO2018/114882合成。將聚合物溶解於3-苯氧基甲苯中，使得在此若待利用噴墨印刷達到用於裝置之典型20nm的層厚度，則溶液通常具有約5 g/l的固體含量。 發光層包含如下表2中所述之基質材料(一種主體化合物或二種主體化合物)和摻雜劑。將用於發光層的混合物溶解於3-苯氧基甲苯中。在此若待利用噴墨印刷達到用於裝置之典型30nm的層厚度，則該等溶液的固體含量為10 mg/ml。也將藍色發光層(B-EML)噴墨印刷，接著真空乾燥及在150℃下退火10分鐘。噴墨印刷係在環境氛圍下進行，而退火是在氬氛圍下進行。 根據圖4a製備的裝置係使用於評估EML薄膜均勻性。 為了製備用於電光示性的根據圖4b之裝置，則將樣品轉移至真空沉積室中，在其中使用熱蒸發進行兩個電子傳輸層(ETL1、ETL2)、電子注入層(EIL)和陰極(Al)之沉積。特此ETL1由ETM1 (5nm薄膜厚度)組成，而ETL2由ETM1和ETM2之1：1體積%混合物(40nm薄膜厚度)組成。電子注入層由ETM2(2nm)組成和陰極為鋁(100nm)。結構係顯示於表1中。 蒸發後，在氬氛圍的手套箱中封裝裝置。
Figure 02_image279
b) 發光薄膜均勻性之評估 對於顯示器的製造，非常重要的是得到非常良好的像素均勻性而同時具有良好的裝置性能。層厚度的不均勻性造成不均勻的發光強度分佈，薄膜厚度較薄的區域顯示發光強度增加，而較厚的區域顯示發光強度減少。該不均勻性隨著像素而改變，從而阻止像素之間的可再現外觀。綜合而言，此將導致對該類顯示器的品質有負面看法。因此，本發明解決EML薄膜均勻性和裝置性能的課題。從而評估的第一步為檢測薄膜均勻性。為此，使用圖4a所示的堆疊。在EML沉積後停止處理。薄膜係如a)部分中所述製備。EML的組成物係顯示於表2-A和表2-B中。 為了評估印刷薄膜的均勻性，印刷薄膜的形貎係以輪廓儀(profilometer)沿著10µm輪廓特性化，並計算Rp-v(峰谷)值以及粗糙度的均方根差。使用來自KLA-Tencor Corporation之配備2 μm記錄針的輪廓儀Alpha-step D120測量薄膜輪廓。Rp-v值對應於在所測量的輪廓內之測得的最大峰(Rp)和最小峰(Rv)之高度差。為了便於查看，減去薄膜輪廓的基線，使得最小峰對應於0 nm高度且所有圖的軸刻度均相同。 下列二式係用於決定薄膜均勻性：峰谷差Rp-v，其表示層內之最大高度差(式1)，及均方根的粗糙度RMS，其使用高度差的均方根值對平均線z i(式2)。
Figure 02_image281
Figure 02_image283
相較於其中僅使用主體組分2之PR1，包含根據本發明之主體混合物的實例PE1顯示顯著減少的Rp-v和RMS，且對應於更平滑的薄膜(圖1和3)。 此外，相較於PR2，實施例PE1亦顯示類似的Rp-v和RMS值，而導致如下所示之更好的OLED性能(參見表5b、參考3和實施例2)。 額外發光層(EML)的其他薄膜均勻性如下表2-B所示及包含對應EML之OLED的性能係顯示於表5a至5f中。
Figure 02_image285
對於具有輪廓PE2、PE3、PE4、PE5、PE6、PE7、PE8和PE9的發光層，與上述PE1相同的討論是有效的。 可比較使用具有輪廓 PE1至PE9的EML之裝置的性能與其他裝置(參見表5a 至5f)。對於根據本發明之所有發光層輪廓(PE2至PE7)，相較於單獨使用主體化合物2(PR4、PR6、PR8、PR10、PR12、PR14、PR16和PR18)，觀察到顯著較低的Rp-v和RMS值，而該等值與從單一主體化合物1(PR3、PR5、PR7、PR9、PR11、PR13、PR15、PR17)獲得之值相似。本發明超越單獨使用主體化合物1的優勢係說明於裝置結果部分。 c) 裝置結果 如圖4b中所示的裝置係根據a)部份製備。主體材料係顯示於表3中及發光體係顯示於表4中。藍色EML油墨係如表5a-f中所示混合，其亦顯示個別實例之在1000 cd/m 2下的相對外部量子效率(相對EQE)和相對裝置壽命(在1000 cd/m 2下的相對LT90)。
Figure 02_image287
Figure 02_image289
Figure 02_image291
在手套箱內封裝後，將OLED以標準方法示性。為此目的，測定電致發光光譜、假設Lambert發光特性的電流/電壓/發光密度特徵曲線(IUL特徵曲線)、和(操作)壽命。IUL特徵曲線係用於確定諸如在某發光強度下的外部量子效率(以%表示)的優點之特徵圖。在各施加電壓斜坡的步驟下以恒電壓驅動裝置。在對應於初始發光強度的給定電流下測量裝置壽命。接著藉由校正過的光二極體隨時間測量發光強度。
Figure 02_image293
Figure 02_image295
Figure 02_image297
Figure 02_image299
Figure 02_image301
Figure 02_image303
Figure 02_image305
Figure 02_image307
Figure 02_image309
相較於單一主體類型H1，混合主體系統的所示實施例全部顯示改良的裝置性能，而可達到與主體類型H2類似的性能。此與所使用的發光體和所使用的發光體濃度無關。 如上所述，從表5b已確定參考3、4和實施例2的輪廓(參見圖1至3)。相較於參考3，根據本發明之實施例2和3顯示在效率和壽命方面之改良的裝置性能。相較於顯示非常不均勻的薄膜之參考4，包含根據本發明之混合主體的薄膜是非常均勻的，且同時顯示類似的裝置性能。 相同的論據對於表5a至5f中所示的根據本發明之裝置是有效的。 藉助於本發明，可能達成良好的OLED裝置性能而同時確保均勻膜的品質。 Synthesis examples a) Hosts H1 The synthesis of hosts of formula (H1) is known to those skilled in the art and is described eg in WO 2010/151006 and WO 2020/089138. Other synthesis examples are described below: Synthesis of A1
Figure 02_image263
Oven-dried flask equipped with magnetic stir bar, 1 (2417686-30-5) (13.0 g, 36.9 mmol, 1.0 equiv.), 2 (2377545-66-7) (18.4 g, 54 mmol) under argon atmosphere , ginseng(dibenzylideneacetone)dipalladium (1.3 g, 1.4 mmol), SPhos (1.16 g, 2.8 mmol) and potassium fluoride (5.3 g, 92.3 mmol). Toluene (150 mL), 1,4-dioxane (150 mL) and water (150 mL) were added and the mixture was refluxed overnight. The crude product was purified by column chromatography and sublimation. The desired product was isolated as a colorless solid (5.2 g, 9.1 mmol, 25%). The following compounds can be synthesized in a similar manner:
Figure 02_image265
Figure 02_image267
Synthesis of A6
Figure 02_image269
Dissolve 5 g (8.9 mmol) of 2417297-74-4 in 100 ml of toluene-d8. 4.7 ml (0.05 mol) trifluoromethanesulfonic acid was added dropwise at room temperature. The solution turned black and was stirred at room temperature for 2.5 hours. By keeping the temperature constant, 20 ml of deuterium oxide were added. The solution turned orange. After 16 hours, 50 ml of an aqueous potassium phosphate solution and 50 ml of toluene were added. The organic phase was washed with water and dried over magnesium sulfate. The crude material was filtered through silica (toluene). The product was purified by column chromatography (silica, toluene/heptane) and crystallization from toluene/heptane. The remaining solvent was removed by sublimation. Deuteration grades were obtained by NMR spectroscopy and LC-MS. Yield: 2.8 g (4.8 mmol; 54%) b) Host H2 The synthesis of hosts of formula (H2) is known to those skilled in the art and is described eg in EP20187118.3, EP20187122.5, KR20170096860 and CN109867646. Other synthesis examples are described below: Synthesis of compound B1 :
Figure 02_image271
15 g (38 mmol) 8-bromo-dibenzofuran-1-yl trifluoromethanesulfonate, 43.3 g (114 mmol) 4,4,5,5-tetramethyl-2-(10-benzene base-anthracen-9-yl)-[1,3,2]dioxaborolane (dioxaborolane), 35.5 g (167 mmol) potassium phosphate and 1.6 g (1,9 mmol) XPhos Palladacycle Gen. 3 dissolved In 450 ml THF/water (2:1). The mixture was stirred at 90°C for 16 hours. After cooling to room temperature, 300 ml of ethanol were added and the mixture was stirred for one hour. The precipitate was filtered off and washed with ethanol. The material was dissolved in toluene and filtered through a filter plug (silica, toluene). The resulting material was a yellow solid which was further purified by multiple crystallizations from toluene/heptane to yield a light yellow solid (HPLC >99.9). The remaining solvent was removed by sublimation (10 −5 bar at 330° C.). Yield: 15.2 g (22.6 mmol; 60%) The following compounds can be synthesized in an analogous manner:
Figure 02_image273
Synthesis of E1-B3
Figure 02_image275
8.4 g (30 mmol) 2173554-83-9, 15.2 g (40 mmol) 4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3 ,2] Dioxaborolane (dioxaborolane), 15.9 g (75 mmol) potassium phosphate and 1.3 g (1.5 mmol) XPhos Palladacycle Gen. 3 were dissolved in 400 ml THF/water (2:1). The mixture was stirred at 90°C for 16 hours. After cooling to room temperature, 300 ml of ethanol were added and the mixture was stirred for one hour. The precipitate was filtered off and washed with ethanol. The material was dissolved in toluene and filtered through a filter plug (silica, toluene). The resulting material was a solid which was further purified by column chromatography and crystallization from toluene/heptane (HPLC>98.0). Yield: 4.2 g (9.3 mmol; 31%). Synthesis of B3
Figure 02_image277
Dissolve in 300 ml in THF/water (2:1). The mixture was stirred at 90°C for 16 hours. After cooling to room temperature, 300 ml of ethanol were added and the mixture was stirred for one hour. The precipitate was filtered off and washed with ethanol. The material was dissolved in toluene and filtered through a filter plug (silica, toluene). The resulting material was a solid which was further purified by column chromatography and crystallization from toluene/heptane (HPLC >99.9). The remaining solvent was removed by sublimation (10 −5 bar at 340° C.). Yield: 0.96 g (2.1 mmol; 23%) Device example a) Preparation of thin films and devices Glass substrates covered with pre-structured ITO (50 nm) and blank material were cleaned in deionized water using ultrasound. Hereinafter, the substrates were dried using an air gun and then annealed on a hot plate at 225° C. for 2 hours. All following method steps were performed under yellow light. The following layer sequence is shown in Figures 4a and 4b. A hole injection layer (HIL) was inkjet printed on the substrate with a thickness of 20 nm and dried under vacuum. For this purpose, the HIL ink has a solids concentration of 6 g/l. The HIL was then annealed at 220°C for 30 minutes. Inkjet printing and annealing of HIL were carried out in air. As HIL material, a hole-transporting crosslinkable polymer and a p-doped salt were dissolved in 3-phenoxytoluene. These materials are described eg in (ie) WO2016/107668, WO2013/081052 and EP2325190. On top of the HIL, a hole transport layer was inkjet printed under ambient conditions, dried in vacuum and annealed at 220° C. for 30 minutes in an argon atmosphere. The hole transport layer is a polymer (HTM1) with the structure shown in Table 1, which is synthesized according to WO2013156130 or polymer HTM2 (Table 1), which is synthesized according to WO2018/114882. The polymer is dissolved in 3-phenoxytoluene such that the solution generally has a solids content of about 5 g/l if inkjet printing is to be used here to achieve a typical layer thickness of 20 nm for devices. The light-emitting layer contained a host material (one host compound or two host compounds) and a dopant as described in Table 2 below. The mixture used for the light-emitting layer was dissolved in 3-phenoxytoluene. The solutions have a solids content of 10 mg/ml if inkjet printing is to be used to achieve a typical layer thickness of 30 nm for devices. The blue light-emitting layer (B-EML) was also inkjet printed, followed by vacuum drying and annealing at 150° C. for 10 minutes. Inkjet printing was performed under ambient atmosphere, while annealing was performed under argon atmosphere. The device prepared according to Fig. 4a was used to evaluate the EML film uniformity. In order to prepare the device according to Figure 4b for electro-optic characterization, the sample was transferred to a vacuum deposition chamber where two electron transport layers (ETL1, ETL2), electron injection layer (EIL) and cathode ( Al) deposition. ETL1 is hereby composed of ETM1 (5nm film thickness) and ETL2 is composed of a 1:1 volume % mixture of ETM1 and ETM2 (40nm film thickness). The electron injection layer consisted of ETM2 (2nm) and the cathode was aluminum (100nm). The structures are shown in Table 1. After evaporation, the device was packaged in a glove box under an argon atmosphere.
Figure 02_image279
b) Evaluation of Luminescent Film Uniformity For the manufacture of displays, it is very important to obtain very good pixel uniformity while having good device performance. Inhomogeneity in layer thickness results in a non-uniform luminous intensity distribution, with regions of thinner film thickness showing increased luminous intensity and thicker regions showing decreased luminous intensity. This non-uniformity varies from pixel to pixel, preventing a reproducible appearance between pixels. Taken together, this will lead to a negative perception of the quality of this type of display. Therefore, the present invention addresses the issues of EML thin film uniformity and device performance. Thus the first step in the evaluation is to check the film uniformity. For this, the stack shown in Figure 4a is used. Treatment was stopped after EML deposition. Films were prepared as described in part a). The compositional systems of EML are shown in Table 2-A and Table 2-B. In order to evaluate the uniformity of the printed film, the shape of the printed film was characterized by a profiler (profilometer) along the 10µm profile, and the Rp-v (peak-to-valley) value and the root mean square difference of the roughness were calculated. Film profiles were measured using a profiler Alpha-step D120 from KLA-Tencor Corporation equipped with a 2 μm stylus. The Rp-v value corresponds to the measured height difference between the largest peak (Rp) and the smallest peak (Rv) within the measured profile. For ease of viewing, the baseline of the film profile was subtracted such that the smallest peak corresponds to 0 nm height and the axis scales are the same for all plots. The following two equations are used to determine film uniformity: the peak-to-valley difference Rp-v, which represents the maximum height difference within a layer (Equation 1), and the root mean square roughness RMS, which uses the root mean square value of the height difference to mean line z i (Equation 2).
Figure 02_image281
Figure 02_image283
Example PE1 comprising the host mixture according to the invention showed significantly reduced Rp-v and RMS compared to PR1 in which only host component 2 was used, and corresponded to smoother films ( FIGS. 1 and 3 ). Furthermore, Example PE1 also showed similar Rp-v and RMS values compared to PR2, resulting in better OLED performance as shown below (see Table 5b, Reference 3 and Example 2). Other thin film uniformities of the additional light-emitting layer (EML) are shown in Table 2-B below and the properties of OLEDs comprising corresponding EMLs are shown in Tables 5a to 5f.
Figure 02_image285
For luminescent layers with profiles PE2, PE3, PE4, PE5, PE6, PE7, PE8 and PE9, the same discussion as above for PE1 is valid. The performance of devices using EMLs with profiles PE1 to PE9 can be compared with other devices (see Tables 5a to 5f). For all emissive layer profiles (PE2 to PE7) according to the invention, significantly lower Rp-v was observed compared to host compound 2 alone (PR4, PR6, PR8, PR10, PR12, PR14, PR16 and PR18) and RMS values, which were similar to those obtained from single host compound 1 (PR3, PR5, PR7, PR9, PR11, PR13, PR15, PR17). The advantages of the present invention over the use of host compound 1 alone are illustrated in the Device Results section. c) Device Results The device shown in Figure 4b was prepared according to part a). The host materials are shown in Table 3 and the luminescent systems are shown in Table 4. The blue EML inks were mixed as shown in Tables 5a-f, which also show the relative external quantum efficiency (relative EQE) at 1000 cd/ m2 and the relative device lifetime (relative EQE at 1000 cd/ m2 ) of individual examples. relative to LT90).
Figure 02_image287
Figure 02_image289
Figure 02_image291
After encapsulation in the glove box, the OLEDs were characterized by standard methods. For this purpose, the electroluminescence spectrum, the current/voltage/luminous density characteristic curve (IUL characteristic curve) assuming the Lambert luminescence characteristic, and the (operating) lifetime are determined. The IUL characteristic curve is a characteristic diagram used to determine advantages such as external quantum efficiency (expressed in %) at a certain luminous intensity. The device was driven at a constant voltage at each step of the applied voltage ramp. The device lifetime was measured at a given current corresponding to the initial luminous intensity. Luminous intensity is then measured over time by the calibrated photodiode.
Figure 02_image293
Figure 02_image295
Figure 02_image297
Figure 02_image299
Figure 02_image301
Figure 02_image303
Figure 02_image305
Figure 02_image307
Figure 02_image309
The illustrated embodiments of the mixed-body system all show improved device performance compared to single-body type H1 , while similar performance to body type H2 can be achieved. This is independent of the illuminant used and the illuminant concentration used. As mentioned above, the profiles of references 3, 4 and example 2 have been determined from Table 5b (see Figures 1 to 3). Compared to Reference 3, Examples 2 and 3 according to the invention show improved device performance in terms of efficiency and lifetime. Compared to Reference 4 which showed a very inhomogeneous film, the film comprising the hybrid host according to the invention was very homogeneous and at the same time showed similar device performance. The same argument is valid for the devices according to the invention shown in Tables 5a to 5f. By means of the present invention it is possible to achieve good OLED device performance while ensuring uniform film quality.

[圖1]：顯示薄膜輪廓PR1。 [圖2]：顯示薄膜輪廓PR2。 [圖3]：顯示薄膜輪廓PE1。 [圖4a]：用於評估發光層之薄膜均勻性的裝置之堆疊。 [圖4b]：用於評估裝置之性能的裝置之堆疊。 [Fig. 1]: The film profile PR1 is displayed. [Fig. 2]: The film profile PR2 is displayed. [Fig. 3]: The film profile PE1 is shown. [FIG. 4a]: A stack of devices for evaluating the thin film uniformity of the light-emitting layer. [Fig. 4b]: Stack of devices used to evaluate the performance of the devices.

Claims (23)

一種組成物，其包含式(H1)化合物和式(H2)化合物，
Figure 03_image001
Figure 03_image003
其中下列適用於所使用的符號和標號： E 1、E 2、E 3和E 4在每次出現時相同或不同地代表單鍵、-BR 0-、-C(R 0) 2-、-Si(R 0) 2-、-C(=O)-、-O-、 -S-、-S(=O)-、-SO 2-、-N(R 0)-或-P(R 0)-；其先決條件為，在包含E 1和E 3之環中，只有一個基團E 1或E 3可為單鍵及，在包含E 2和E 4之環中，只有一個基團E 2或E 4可為單鍵； E 5代表O或S； X 1至X 12在每次出現時相同或不同地代表C-R X、C-Ar X或N；其先決條件為至少一個選自X 1至X 12之基團代表基團C-Ar X及Ar X代表式(Ar X)之基團：
Figure 03_image005
其中虛線鍵表示至C-Ar X中之基團C的鍵結； Z 1至Z 8在每次出現時相同或不同地代表C-R Z、C-Ar Z或N；其先決條件為至少一個選自Z 1至Z 8之基團代表基團C-Ar Z及Ar Z代表式(Ar Z)之基團：
Figure 03_image007
其中虛線鍵表示至C-Ar Z中之基團C的鍵結； Ar 1在每次出現時相同或不同地為具有10至60個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R V取代； Ar 3在每次出現時相同或不同地為具有10至60個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R Y取代； Ar 2、Ar 4、Ar S在每次出現時相同或不同地為具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R取代； R V、R X、R Y、R Z在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R) 2、N(Ar) 2、NO 2、Si(R) 3、B(OR) 2、OSO 2R、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基，彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經RC=CR、C≡C、Si(R) 2、Ge(R) 2、Sn(R) 2、C=O、C=S、C=Se、P(=O)(R)、SO、SO 2、O、S或CONR置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換、具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代、或具有5至60個芳族環原子之芳氧基，其可經一或多個基團R取代； 其中二個基團R V、二個基團R X、二個基團R Y、二個基團R Z可一起形成脂族、芳族或雜芳族環系統，其可經一或多個基團R取代； R 0在每次出現時相同或不同地代表H、D、F、具有1至20個C原子之直鏈烷基、或具有3至20個C原子之支鏈或環數烷基，彼等各自可經一或多個基團R取代，其中在各情況下一或多個非相鄰的CH 2基團可經O或S置換及其中一或多個H原子可經D或F置換、或具有5至40個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代，其中二個相鄰基團R 0，可一起形成脂族或芳族環系統，其可經一或多個基團R取代； R   在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar、P(=O)(Ar) 2、S(=O)Ar、S(=O) 2Ar、N(R’) 2、N(Ar) 2、NO 2、Si(R’) 3、B(OR’) 2、OSO 2R’、具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkyl)或具有3至40個C原子之支鏈或環狀烷基、烷氧基或烷硫基，彼等各自可經一或多個基團R’取代，其中在各情況下一或多個非相鄰的CH 2基團可經R’C=CR’、C≡C、Si(R’) 2、Ge(R’) 2、Sn(R’) 2、C=O、C=S、C=Se、P(=O)(R’)、SO、SO 2、O、S或CONR’置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO 2置換、具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R’取代、或具有5至60個芳族環原子之芳氧基，其可經一或多個基團R’取代；其中二個基團R可一起形成脂族或芳族環系統，其可經一或多個基團R’取代； Ar 在每次出現時相同或不同地為具有5至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R’取代； R’ 在每次出現時相同或不同地代表H、D、F、Cl、Br、I、CN、具有1至20個C原子之直鏈烷基、烷氧基或烷硫基或具有3至20個C原子之支鏈或環狀烷基、烷氧基、或烷硫基，其中在各情況下一或多個非相鄰的CH 2基團可經SO、SO 2、O、S置換及其中一或多個H原子可經D、F、Cl、Br或I置換、或具有5至24個芳族環原子之芳族或雜芳族環系統；及 p、s 在每次出現時相同或不同地為0或1，其中： 當p或s為0時，則對應Ar S不存在及基團Ar 1或Ar 3直接鍵結至C-Ar X或C-Ar Z中之C； q、t 在每次出現時相同或不同地為0、1或2，其中： 當q為0時，則Ar 4不存在；當t為0時，則Ar 2不存在； 當q為1或2時，則Ar 1係經一個基團或二個基團Ar 4取代； 當t為1或2時，則Ar 3係經一個基團或二個基團Ar 2取代。 A composition comprising a compound of formula (H1) and a compound of formula (H2),
Figure 03_image001
Figure 03_image003
Wherein the following applies for the symbols and designations used: E 1 , E 2 , E 3 and E 4 represent, identically or differently at each occurrence, a single bond, -BR 0 -, -C(R 0 ) 2 -, - Si(R 0 ) 2 -, -C(=O)-, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 )-, or -P(R 0 )-; the prerequisite is that, in the ring containing E 1 and E 3 , only one group E 1 or E 3 can be a single bond, and in the ring containing E 2 and E 4 , only one group E 2 or E 4 may be a single bond; E 5 represents O or S; X 1 to X 12 represent CR X , C-Ar X or N identically or differently at each occurrence; its prerequisite is that at least one is selected from X The group of 1 to X 12 represents the group C-Ar X and Ar X represents the group of formula (Ar X ):
Figure 03_image005
wherein the dotted bond represents a bond to group C in C-Ar X ; Z 1 to Z 8 represent CR Z , C-Ar Z or N identically or differently at each occurrence; a prerequisite for which is at least one of the selected The group from Z 1 to Z 8 represents the group C-Ar Z and Ar Z represents the group of formula (Ar Z ):
Figure 03_image007
where the dotted bond represents the bond to group C in C-Ar Z ; Ar 1 is identically or differently at each occurrence an aryl or heteroaryl group having 10 to 60 aromatic ring atoms, which in each In each case it can also be substituted by one or more radicals R V ; Ar 3 is identically or differently at each occurrence an aryl or heteroaryl group having 10 to 60 aromatic ring atoms, which in each case is also may be substituted by one or more radicals RY ; Ar 2 , Ar 4 , Ar S are identically or differently at each occurrence an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which In each case also substitution by one or more radicals R; R V , R X , RY , R Z represent H, D, F, Cl, Br, I, CHO identically or differently at each occurrence , CN, C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R) 2 , N(Ar) 2 , NO 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, linear alkyl, alkoxy or thioalkyl with 1 to 40 C atoms or branched chain with 3 to 40 C atoms or cyclic alkyl, alkoxy or alkylthio groups, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH groups may be substituted by RC=CR , C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O , S or CONR replacement and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or aryloxy groups having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R; wherein two radicals R V , two groups R X , two groups R Y , two groups R Z may together form an aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R; R 0 Represents H, D, F, straight-chain alkyl having 1 to 20 C atoms, or branched or cyclic alkyl having 3 to 20 C atoms identically or differently at each occurrence, each of which may Substituted by one or more groups R, where in each case one or more non-adjacent CH groups may be replaced by O or S and where one or more H atoms may be replaced by D or F, or with Aromatic or heteroaromatic ring systems of 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R, wherein two adjacent radicals R 0 , may together form an aliphatic or Aromatic ring systems, which may be substituted by one or more radicals R; R at each occurrence identically or differently represents H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar , P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R') 2 , N(Ar) 2 , NO 2 , Si(R') 3 , B (OR') 2 , OSO 2 R', linear alkyl, alkoxy or thioalkyl with 1 to 40 C atoms or branched or cyclic alkyl with 3 to 40 C atoms , alkoxy or alkylthio, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH groups may be substituted by R'C=CR', C≡C, Si(R') 2 , Ge(R') 2 , Sn(R') 2 , C=O, C=S, C=Se, P(=O)(R'), SO, SO 2 , O, S or CONR' replacement and wherein one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 , aromatic or heteroaromatic with 5 to 60 aromatic ring atoms Aromatic ring systems, which in each case may be substituted by one or more radicals R', or aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R'; wherein Two radicals R may together form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R'; Ar is, in each occurrence, identically or differently, an aliphatic or aromatic ring system having from 5 to 60 aromatic ring atoms Aromatic or heteroaromatic ring systems, which may in each case also be substituted by one or more radicals R';R', identically or differently at each occurrence, represents H, D, F, Cl, Br, I , CN, straight-chain alkyl, alkoxy or alkylthio with 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or alkylthio with 3 to 20 C atoms, wherein In each case one or more non-adjacent CH2 groups may be replaced by SO, SO2 , O, S and one or more H atoms may be replaced by D, F, Cl, Br or I, or have Aromatic or heteroaromatic ring systems of 5 to 24 aromatic ring atoms; and p, s are identically or differently 0 or 1 at each occurrence, wherein: when p or s is 0, then corresponds to ArS Absent and group Ar 1 or Ar 3 is directly bonded to C in C-Ar X or C-Ar Z ; q, t are identically or differently 0, 1 or 2 at each occurrence, wherein: when q When 0, then Ar 4 does not exist; when t is 0, then Ar 2 does not exist; when q is 1 or 2, then Ar 1 is replaced by one group or two groups Ar 4 ; when t is When 1 or 2, then Ar 3 is substituted by one group or two groups Ar 2 . 根據請求項1之組成物，其中，在式(H1)化合物中，至少一個選自X 1至X 4之基團代表基團C-Ar X，其中Ar X代表如請求項1中所定義的式(Ar X)之基團及基團X 5至X 12代表C-R X或N，其中R X係如請求項1中所定義。 According to the composition of claim 1, wherein, in the compound of formula (H1), at least one group selected from X 1 to X 4 represents the group C-Ar X , wherein Ar X represents as defined in claim 1 The group of formula (Ar X ) and the groups X 5 to X 12 represent CR X or N, wherein R X is as defined in Claim 1. 根據請求項1或2之組成物，其中該式(H1)化合物係選自式(H1-A)至(H1-D)之化合物：
Figure 03_image009
其中該等符號具有與請求項1中相同的意義。 The composition according to claim 1 or 2, wherein the compound of formula (H1) is selected from compounds of formula (H1-A) to (H1-D):
Figure 03_image009
Wherein these symbols have the same meanings as in Claim 1. 根據前述請求項中一或多項之組成物，其中該式(H1)化合物係選自下列式之化合物：
Figure 03_image011
Figure 03_image013
Figure 03_image015
Figure 03_image017
Figure 03_image019
Figure 03_image021
Figure 03_image023
其中該等符號R X、Ar X具有與請求項1中相同的意義及基團E 1、E 2、E 3和E 4在每次出現時相同或不同地代表 -BR 0-、-C(R 0) 2-、-Si(R 0) 2-、-C(=O)-、-O-、-S-、-S(=O)-、-SO 2-、-N(R 0)-或-P(R 0)-。 The composition according to one or more of the preceding claims, wherein the compound of formula (H1) is selected from compounds of the following formulae:
Figure 03_image011
Figure 03_image013
Figure 03_image015
Figure 03_image017
Figure 03_image019
Figure 03_image021
Figure 03_image023
Wherein these symbols R X , Ar X have the same meaning as in Claim 1 and the groups E 1 , E 2 , E 3 and E 4 represent -BR 0 -, -C( R 0 ) 2 -, -Si(R 0 ) 2 -, -C(=O)-, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 ) - or -P(R 0 )-. 根據前述請求項中一或多項之組成物，其中，在式(H2)化合物中，一個選自Z 1至Z 4之基團代表基團C-Ar Z及一個選自Z 5至Z 8之基團代表基團C-Ar Z，其中Ar Z代表如請求項1中所定義之式(Ar Z)之基團。 According to the composition of one or more of the preceding claims, wherein, in the compound of formula (H2), one group selected from Z 1 to Z 4 represents the group C-Ar Z and one group selected from Z 5 to Z 8 The group represents the group C—Ar Z , wherein Ar Z represents a group of formula (Ar Z ) as defined in claim 1. 根據前述請求項中一或多項之組成物，其中該化合物(H2)係選自下列式之化合物，
Figure 03_image025
Figure 03_image027
Figure 03_image029
Figure 03_image031
其中該等符號具有與請求項1中相同的意義。 The composition according to one or more of the preceding claims, wherein the compound (H2) is selected from compounds of the following formulae,
Figure 03_image025
Figure 03_image027
Figure 03_image029
Figure 03_image031
Wherein these symbols have the same meanings as in Claim 1. 根據前述請求項中一或多項之組成物，其中該等基團Ar 1和Ar 3在每次出現時係相同或不同地選自由下列所組成之群組：蒽、萘、菲、稠四苯、
Figure 111113074-001
(chrysene)、苯并蒽、苯并菲、芘、苝、聯伸三苯、苯并芘、丙二烯合茀(fluoranthene)，彼等各自可在各自由位置在Ar 1的情況下經基團R V取代，和Ar 3的情況下經基團R Y取代，其中R V和R Y具有與請求項1中相同的意義。 A composition according to one or more of the preceding claims, wherein the groups Ar and Ar are selected at each occurrence, identically or differently, from the group consisting of: anthracene, naphthalene, phenanthrene, condensed tetraphenyl ,
Figure 111113074-001
(chrysene), benzanthracene, triphenylene, pyrene, perylene, triphenylene, benzopyrene, allene and fluoranthene (fluoranthene), each of which can be grouped in the case of Ar in each free position R V is substituted, and in the case of Ar 3 is substituted by a group RY , wherein R V and RY have the same meaning as in claim 1. 根據前述請求項中一或多項之組成物，其中該等基團Ar 1和Ar 3係選自式(Ar-1)至(Ar-11)之基團，
Figure 03_image033
Figure 03_image035
其中該等式(Ar-1)至(Ar-11)之基團可於任何位置鍵結至相鄰的基團且可在各自由位置在Ar 1的情況下經基團R V取代，和在Ar 3的情況下經基團R Y取代，其中R V和R Y具有與請求項1中相同的意義。 According to the composition of one or more of the preceding claims, wherein the groups Ar 1 and Ar 3 are groups selected from formulas (Ar-1) to (Ar-11),
Figure 03_image033
Figure 03_image035
wherein the groups of the formulas (Ar-1) to (Ar-11) may be bonded to adjacent groups at any position and may be substituted by a group R V with each free position at Ar , and In the case of Ar 3 is substituted by a group RY , wherein R V and RY have the same meaning as in claim 1. 根據前述請求項中一或多項之組成物，其中基團Ar X代表式(Ar X-1)之基團：
Figure 03_image037
其中該等符號和標號具有與請求項1中相同的意義及其中該蒽基團可在各自由位置經基團R V取代，其中R V具有與如請求項1項中相同的意義。 The composition according to one or more of the preceding claims, wherein the group Ar X represents a group of formula (Ar X -1):
Figure 03_image037
Wherein these symbols and labels have the same meanings as in claim item 1 and wherein the anthracene group can be substituted at each free position by a group R V , wherein R V has the same meaning as in claim item 1. 根據前述請求項中一或多項之組成物，其中基團Ar X代表下列式之一者的基團：
Figure 03_image039
其中該等符號和標號具有與請求項1中相同的意義及其中該蒽基團可在各自由位置經基團R V取代，其中R V具有與如請求項1項中相同的意義。 The composition according to one or more of the preceding claims, wherein the group Ar X represents a group of one of the following formulas:
Figure 03_image039
Wherein these symbols and labels have the same meanings as in claim item 1 and wherein the anthracene group can be substituted at each free position by a group R V , wherein R V has the same meaning as in claim item 1. 根據前述請求項中一或多項之組成物，其中基團Ar Z代表式(Ar Z-1)之基團：
Figure 03_image041
其中該等符號和標號具有與請求項1中相同的意義及其中該蒽基團可在各自由位置經基團R Y取代，其中R Y具有與如請求項1中相同的意義。 The composition according to one or more of the preceding claims, wherein the group Ar Z represents a group of formula (Ar Z -1):
Figure 03_image041
Wherein these symbols and labels have the same meanings as in Claim 1 and wherein the anthracene group can be substituted at each free position by a group RY , wherein RY has the same meaning as in Claim 1. 根據前述請求項中一或多項之組成物，其中基團Ar Z代表下列式之一者的基團：
Figure 03_image043
其中該等符號和標號具有與請求項1中相同的意義及其中該蒽基團可在各自由位置經基團R Y取代，其中R Y具有與如請求項1中相同的意義。 The composition according to one or more of the preceding claims, wherein the group Ar Z represents a group of one of the following formulas:
Figure 03_image043
Wherein these symbols and labels have the same meanings as in claim item 1 and wherein the anthracene group can be substituted at each free position by a group RY , wherein RY has the same meaning as in claim item 1. 根據前述請求項中一或多項之組成物，其中該等基團Ar 2和Ar 4在每次出現時係相同或不同地選自由下列所組成之群組：苯基、聯苯、聯三苯、聯四苯、茀、螺二茀、萘、蒽、菲、聯伸三苯、丙二烯合茀(fluoranthene)、稠四苯、
Figure 111113074-001
(chrysene)、苯并蒽、苯并菲、芘或苝、二苯并呋喃、咔唑和二苯并噻吩，彼等各自可在任何自由位置經一或多個基團R取代；及其中Ar 2、Ar 4也可為先前所引用的基團中之二或更多者的組合。 A composition according to one or more of the preceding claims, wherein the groups Ar 2 and Ar 4 are identically or differently selected at each occurrence from the group consisting of: phenyl, biphenyl, terphenyl , tetraphenyl, fluorine, spirodifenol, naphthalene, anthracene, phenanthrene, triphenylene, fluoranthene, thick tetraphenyl,
Figure 111113074-001
(chrysene), benzanthracene, triphenylene, pyrene or perylene, dibenzofuran, carbazole and dibenzothiophene, each of which may be substituted at any free position by one or more groups R; and wherein Ar 2. Ar 4 can also be a combination of two or more of the aforementioned groups. 根據前述請求項中一或多項之組成物，其進一步包含螢光發光體。The composition according to one or more of the preceding claims, further comprising a fluorescent light emitter. 根據前述請求項中一或多項之組成物，其包含式(H1)化合物作為第一主體材料、式(H2)化合物作為第二主體材料和螢光發光體作為摻雜劑材料。The composition according to one or more of the preceding claims, which comprises the compound of formula (H1) as the first host material, the compound of formula (H2) as the second host material and the fluorescent emitter as the dopant material. 根據前述請求項中一或多項之組成物，其包含選自由下列所組成之群組的螢光發光體： - 含有三個直接鍵結至氮的經取代或未經取代之芳族或雜芳族環系統的芳基胺； - 橋聯三芳基胺； - 具有至少14個芳族環原子之縮合芳族或雜芳族環系統； - 茚并茀、茚并茀胺或茚并茀二胺； - 苯并茚并茀、苯并茚并茀胺或苯并茚并茀二胺； - 二苯并茚并茀、二苯并茚并茀胺或二苯并茚并茀二胺； - 含有具有至少10個芳族環原子的縮合芳基之茚并茀； - 雙茚并茚并茀； - 茚并二苯并呋喃；茚并茀胺或茚并茀二胺； - 茀二聚物； - 啡㗁𠯤；及 - 硼衍生物。 The composition according to one or more of the preceding claims, comprising a fluorescent emitter selected from the group consisting of: - arylamines containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen; - Bridged triarylamines; - condensed aromatic or heteroaromatic ring systems having at least 14 aromatic ring atoms; - indenoxene, indenoxamine or indenoxenediamine; - benzoindenoxene, benzoindenoxamine or benzoindenoxenediamine; - dibenzoindenofluorene, dibenzoindenotermineamine or dibenzoindenoterminediamine; - indenoxenes containing condensed aryl groups having at least 10 aromatic ring atoms; - Bisindenoindenofluorene; - Indenodibenzofuran; indenoxamine or indenoxenediamine; - Dimer of fennel; - Coffee 㗁𠯤; and - Boron derivatives. 根據前述請求項中一或多項之組成物，其中其包含式(E-1)、(E-2)、(E-3)或(E-4)之螢光發光體，
Figure 03_image045
其中 Ar 10、Ar 11、Ar 12在每次出現時相同或不同地為具有6至60個芳族環原子之芳族或雜芳族環系統，其在各情況下亦可經一或多個基團R取代；其先決條件為至少一個基團Ar 10、Ar 11、Ar 12為具有10至40個芳族環原子之芳族或雜芳族環系統，其含有至少一個由2至4個彼此縮合的芳族環組成的縮合芳基或雜芳基，其中該芳族或雜芳族環系統可經一或多個基團R取代； R    具有與請求項1中相同的定義；及 e     為1、2、3或4；更佳地，e為1；
Figure 03_image047
其中 Ar 20、Ar 21、Ar 22在每次出現時相同或不同地為具有6至30個芳族環原子之芳基或雜芳基，其在各情況下亦可經一或多個基團R取代； E 20在每次出現時係相同或不同地選自BR、C(R 0) 2、Si(R 0) 2、C=O、C=NR 0、C=C(R 0) 2、O、S、S=O、SO 2、NR 0、PR 0、P(=O)R 0或P(=S)R 0之基團；其中Ar 20、Ar 21和E 20一起形成五員環或六員環，及Ar 21、Ar 23和E 20一起形成五員環或六員環； R 0在每次出現時相同或不同地代表H、D、F、具有1至20個(較佳為1至10個C原子)之直鏈烷基或具有3至20個(較佳為3至10個)C原子之支鏈或環狀烷基，彼等各自可經一或多個R基團取代，其中在各情況下一或多個非相鄰的CH 2基團可經O或S置換和其中一或多個H原子可經D或F置換，或具有5至40個(較佳為5至30個，更佳為6至18個)芳族環原子之芳族或雜芳族環系統，其在各情況下可經一或多個基團R取代，其中二個相鄰的基團R 0可一起形成脂族或芳族環系統，其可經一或多個基團R取代， R    具有與請求項1中相同的定義； p、q      在每次出現時相同或不同地為0或1，其先決條件為p+q=1； r     為1、2或3；
Figure 03_image049
其中 Ar 30、Ar 31、Ar 32在每次出現時相同或不同地代表具有5至22個(較佳5至18個，更佳6至14個)芳族環原子之經取代或未經取代之芳基或雜芳基； E 30代表B或N； E 31、E 32、E 33在每次出現時相同或不同地代表O、S、C(R 0) 2、C=O、C=S、C=NR 0、C=C(R 0) 2、Si(R 0) 2、BR 0、NR 0、PR 0、SO 2、SeO 2或化學鍵，其先決條件為若E 30為B，則基團E 31、E 32、E 33中之至少一者代表NR 0及若E 30為N，則基團E 31、E 32、E 33中之至少一者代表BR 0； R 0具有與上述相同的定義； s、t、u  在每次出現時相同或不同地為0或1，其先決條件為s+t+u≥1
Figure 03_image051
其中 Ar 40、Ar 41、Ar 42在每次出現時相同或不同地代表具有5至22個(較佳5至18個，更佳6至14個)芳族環原子之經取代或未經取代之芳基或雜芳基； E 41、E 42、E 43在每次出現時相同或不同地代表O、S、C(R 0) 2、C=O、C=S、C=NR 0、C=C(R 0) 2、Si(R 0) 2、BR 0、NR 0、PR 0、SO 2、SeO 2或化學鍵，其先決條件為基團E 41、E 42、E 43中之至少一者存在且代表化學鍵； R 0具有與上述相同的定義； i、g、h  在每次出現時相同或不同地為0或1，其先決條件為i+g+h≥1。 The composition according to one or more of the preceding claims, wherein it comprises a fluorescent emitter of formula (E-1), (E-2), (E-3) or (E-4),
Figure 03_image045
wherein Ar 10 , Ar 11 , Ar 12 are identically or differently at each occurrence an aromatic or heteroaromatic ring system having 6 to 60 aromatic ring atoms, which may in each case also be replaced by one or more The group R is substituted; the prerequisite for this is that at least one of the groups Ar 10 , Ar 11 , Ar 12 is an aromatic or heteroaromatic ring system with 10 to 40 aromatic ring atoms containing at least one of from 2 to 4 A condensed aryl or heteroaryl group consisting of aromatic rings condensed with each other, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R; R has the same definition as in claim 1; and e is 1, 2, 3 or 4; more preferably, e is 1;
Figure 03_image047
wherein Ar 20 , Ar 21 , Ar 22 are identically or differently at each occurrence an aryl or heteroaryl group having 6 to 30 aromatic ring atoms, which in each case may also be represented by one or more groups R substitution; E 20 at each occurrence is identically or differently selected from BR, C(R 0 ) 2 , Si(R 0 ) 2 , C=O, C=NR 0 , C=C(R 0 ) 2 , O, S, S=O, SO 2 , NR 0 , PR 0 , P(=O)R 0 or P(=S)R 0 groups; where Ar 20 , Ar 21 and E 20 together form five members ring or a six-membered ring, and Ar 21 , Ar 23 and E 20 together form a five-membered ring or a six-membered ring; R 0 represents H, D, F, with 1 to 20 (compared to A straight-chain alkyl group preferably having 1 to 10 C atoms) or a branched or cyclic alkyl group having 3 to 20 (preferably 3 to 10) C atoms, each of which can be passed through one or more R Group substitution, wherein in each case one or more non-adjacent CH groups can be replaced by O or S and wherein one or more H atoms can be replaced by D or F, or with 5 to 40 (relatively Aromatic or heteroaromatic ring systems having preferably 5 to 30, more preferably 6 to 18) aromatic ring atoms, which may in each case be substituted by one or more radicals R, two of which are adjacent The groups R 0 of may together form an aliphatic or aromatic ring system, which may be substituted by one or more groups R, R has the same definition as in claim 1; p, q are the same or different at each occurrence ground is 0 or 1, and its prerequisite is p+q=1; r is 1, 2 or 3;
Figure 03_image049
Wherein Ar 30 , Ar 31 , Ar 32 represent identically or differently each occurrence of substituted or unsubstituted aromatic ring atoms having 5 to 22 (preferably 5 to 18, more preferably 6 to 14) aromatic ring atoms. aryl or heteroaryl; E 30 represents B or N; E 31 , E 32 , E 33 represent O, S, C(R 0 ) 2 , C=O, C= S, C=NR 0 , C=C(R 0 ) 2 , Si(R 0 ) 2 , BR 0 , NR 0 , PR 0 , SO 2 , SeO 2 or a chemical bond, the prerequisite is that if E 30 is B, Then at least one of the groups E 31 , E 32 , E 33 represents NR 0 and if E 30 is N, at least one of the groups E 31 , E 32 , E 33 represents BR 0 ; R 0 has the same Same definition as above; s, t, u are equally or differently 0 or 1 at each occurrence, with the precondition that s+t+u≥1
Figure 03_image051
Wherein Ar 40 , Ar 41 , Ar 42 represent identically or differently each occurrence of substituted or unsubstituted aromatic ring atoms having 5 to 22 (preferably 5 to 18, more preferably 6 to 14) aromatic ring atoms. Aryl or heteroaryl; E 41 , E 42 , E 43 represent O, S, C(R 0 ) 2 , C=O, C=S, C=NR 0 , C=C(R 0 ) 2 , Si(R 0 ) 2 , BR 0 , NR 0 , PR 0 , SO 2 , SeO 2 or a chemical bond, the prerequisite being at least one of the groups E 41 , E 42 , E 43 One is present and represents a chemical bond; R 0 has the same definition as above; i, g, h are identically or differently 0 or 1 at each occurrence, with the prerequisite that i+g+h≧1. 一種調配物，其包含至少一種根據請求項1至17中一或多項之組成物和至少一種溶劑。A formulation comprising at least one composition according to one or more of claims 1 to 17 and at least one solvent. 一種製造電子裝置之方法，該電子裝置包含至少一層包含根據請求項1至17中一或多項之組成物的層： a) 製備一種包含至少一種根據請求項1至17中一或多項之組成物和至少一種溶劑的調配物； b) 將步驟a)中製備的調配物施加在基板上或另一層上以形成一層； c) 將該層乾燥以移除該溶劑。 A method of manufacturing an electronic device comprising at least one layer comprising a composition according to one or more of claims 1 to 17: a) preparing a formulation comprising at least one composition according to one or more of claims 1 to 17 and at least one solvent; b) applying the formulation prepared in step a) to a substrate or another layer to form a layer; c) drying the layer to remove the solvent. 根據請求項19之方法，其中該調配物係以塗佈法或印刷法施加。The method according to claim 19, wherein the formulation is applied by coating or printing. 根據請求項19或20之方法，其中該調配物係以泛塗(flood coating)、浸塗、噴塗、旋轉塗佈、網版印刷、凸版印刷、凹版印刷、輥塗、噴墨印刷、旋轉印刷、快乾印刷、平版印刷、縫模塗佈(slot die coating)或噴嘴印刷施加。The method according to claim 19 or 20, wherein the formulation is applied by flood coating, dip coating, spray coating, spin coating, screen printing, letterpress printing, gravure printing, roll coating, inkjet printing, rotary printing , quick-drying printing, lithographic printing, slot die coating (slot die coating) or nozzle printing application. 一種電子裝置，其包含陽極、陰極、和至少一個發光層，其中該發光層包含根據請求項1至17中一或多項之組成物。An electronic device comprising an anode, a cathode, and at least one light-emitting layer, wherein the light-emitting layer comprises the composition according to one or more of claims 1-17. 根據請求項22之電子裝置，其係選自由下列所組成之群組：有機電致發光裝置、有機積體電路、有機場效電晶體、有機薄膜電晶體、有機發光電晶體、有機太陽能電池、染料敏化有機太陽能電池、有機光學檢測器、有機感光器、有機場淬滅裝置、發光電化學電池、有機雷射二極體和有機電漿子發光裝置。The electronic device according to claim 22, which is selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light-emitting transistors, organic solar cells, Dye-sensitized organic solar cells, organic optical detectors, organic photoreceptors, organic field quenching devices, light-emitting electrochemical cells, organic laser diodes, and organic plasmonic light-emitting devices.
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