TW202313532A

TW202313532A - Aromatic compound and organic electroluminescent element

Info

Publication number: TW202313532A
Application number: TW111120563A
Authority: TW
Inventors: 長谷川司; 岡部一毅; 李延軍; 弘大輔
Original assignee: 日商三菱化學股份有限公司
Priority date: 2021-06-04
Filing date: 2022-06-02
Publication date: 2023-04-01
Also published as: KR20240016268A; JPWO2022255402A1; WO2022255402A1

Abstract

An organic electroluminescent element which comprises a positive electrode and a negative electrode on a substrate, while having an organic layer between the positive electrode and the negative electrode, wherein the organic layer comprises a layer that contains an aromatic compound represented by formula (1). (In the formula, each of Ar1 to Ar5 represents a hydrogen atom or an aromatic hydrocarbon group having 6 to 60 carbon atoms; at least one of Ar1, Ar2 and Ar5 is represented by formula (2) or formula (3); each of L1 to L5 represents an aromatic hydrocarbon group having 6 to 60 carbon atoms; and R represents a specific substituent.).

Description

芳香族化合物及有機電場發光元件Aromatic compounds and organic electroluminescent devices

本發明是有關於一種可用於有機電場發光元件（以下，有時稱為「有機發光二極體（organic light emitting diode，OLED）」或「元件」）的芳香族化合物。另外，本發明是有關於一種具有該芳香族化合物的有機電場發光元件、具有該有機電場發光元件的顯示裝置及照明裝置、含有該化合物及有機溶劑的組成物、使用該組成物的薄膜形成方法及有機電場發光元件的製造方法。The present invention relates to an aromatic compound that can be used in organic electroluminescent devices (hereinafter, sometimes referred to as "organic light emitting diode (OLED)" or "device"). In addition, the present invention relates to an organic electroluminescent device having the aromatic compound, a display device and a lighting device having the organic electroluminescent device, a composition containing the compound and an organic solvent, and a method of forming a thin film using the composition And a method for manufacturing an organic electroluminescence element.

近年來，作為薄膜型的電場發光元件，進行使用有機薄膜的有機電場發光元件的開發來代替使用無機材料的有機電場發光元件。有機電場發光元件（OLED）通常於陽極與陰極之間具有電洞注入層、電洞傳輸層、有機發光層、電子傳輸層等。適於該各層的材料正在不斷開發，發光顏色亦以紅、綠、藍而分別推進開發。另外，與先前的蒸鍍型相比，正推進材料利用效率高、可降低製造成本的塗佈型OLED的研究。In recent years, as a thin-film type electroluminescent element, an organic electroluminescent element using an organic thin film has been developed instead of an organic electroluminescent element using an inorganic material. An organic electroluminescent device (OLED) usually has a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, etc. between the anode and the cathode. Materials suitable for each layer are being continuously developed, and the luminescent colors are also being developed separately for red, green, and blue. In addition, compared with the conventional vapor deposition type, research is advancing on a coating type OLED that has high material utilization efficiency and can reduce manufacturing costs.

於塗佈型OLED中，要求元件的長壽命化或更低消耗功率下的驅動。對元件的壽命或消耗功率改善帶來影響的原因考慮有各種因素。例如，關於壽命，認為構成元件的材料的耐熱耐久性、或結晶性會帶來大的影響。In coating-type OLEDs, longer device life and driving with lower power consumption are required. Various factors are considered to affect the improvement of the life of the element or the power consumption. For example, regarding the lifetime, it is considered that the heat resistance durability and crystallinity of the material constituting the element have a great influence.

為了藉由濕式成膜法來製造有機電場發光元件，所使用的材料需要全部為可溶解於有機溶劑中而作為油墨來使用的材料。若使用材料的溶解性差，則需要長時間加熱等操作，因此存在於使用前材料劣化的可能性。若無法於溶液狀態下長時間保持均勻狀態，則會發生材料自溶液的析出，從而無法利用噴墨裝置等進行成膜。對於濕式成膜法中所使用的材料，要求迅速溶解於有機溶劑、於溶解後不析出而保持均勻狀態此兩種意義上的溶解性。 In order to manufacture an organic electroluminescent device by a wet film-forming method, all materials used need to be soluble in an organic solvent and used as an ink. If the solubility of the material used is poor, operations such as heating for a long time are required, and therefore there is a possibility that the material deteriorates before use. If a uniform state cannot be maintained in a solution state for a long period of time, material will be precipitated from the solution, making it impossible to form a film using an inkjet device or the like. The materials used in the wet film-forming method are required to have solubility in two senses: rapidly dissolving in an organic solvent and maintaining a uniform state without precipitation after dissolution.

為了藉由將有機層積層多層進行塗佈並成膜，利用濕式成膜法形成全部有機層來製作有機電場發光元件，要求於濕式成膜後，對塗佈於其上的油墨的耐溶劑性。In order to fabricate an organic electroluminescent device by coating and forming a multilayer organic layer and forming all the organic layers by a wet film-forming method, resistance to the ink coated thereon after wet film-forming is required. Solvent.

於專利文獻1中，作為磷光發光性化合物的電荷傳輸材料，報告一種使用下述化合物（C-1）、下述化合物（C-2）等芳香族化合物的OLED用材料。Patent Document 1 reports a material for OLED using an aromatic compound such as the following compound (C-1) and the following compound (C-2) as a charge transport material of a phosphorescent compound.

[化1]

[chemical 1]

專利文獻1：國際公開第2007/043357號Patent Document 1: International Publication No. 2007/043357

所述化合物雖然溶解性高，帶隙大，但關於玻璃轉移溫度，於化合物（C-1）中低至99℃，於化合物（C-2）中低至87℃而耐熱性不充分。另外，於由所述化合物成膜的薄膜上，利用使用醇系溶劑的濕式成膜法積層薄膜時，針對所使用的醇系溶劑的耐溶劑性不充分。Although the compound has high solubility and a large band gap, its glass transition temperature is as low as 99° C. in the compound (C-1) and as low as 87° C. in the compound (C-2), and the heat resistance is insufficient. In addition, when a thin film formed from the compound is laminated by a wet film-forming method using an alcoholic solvent, the solvent resistance against the alcoholic solvent used is insufficient.

本發明的課題在於提供一種耐熱性、溶劑溶解性優異、並且針對薄膜中的醇系溶劑的耐溶劑性亦優異、以及帶隙大的化合物。另外，本發明的課題在於提供一種具有該化合物的有機電場發光元件、具有該有機電場發光元件的顯示裝置及照明裝置、含有該化合物及溶劑的組成物、使用該組成物的薄膜形成方法及有機電場發光元件的製造方法。 [解決課題之手段] An object of the present invention is to provide a compound having excellent heat resistance and solvent solubility, excellent solvent resistance to alcohol-based solvents in thin films, and a large band gap. In addition, the object of the present invention is to provide an organic electroluminescent device having the compound, a display device and a lighting device having the organic electroluminescent device, a composition containing the compound and a solvent, a method of forming a thin film using the composition, and an organic electroluminescent device. A method of manufacturing an electroluminescence element. [Means to solve the problem]

本發明者發現，藉由使用特定結構的芳香族化合物而可解決所述課題。The inventors of the present invention found that the above-mentioned problems can be solved by using an aromatic compound of a specific structure.

本發明的主旨如以下的＜1＞～＜32＞般。The gist of the present invention is as follows <1> to <32>.

＜1＞一種有機電場發光元件，於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件中，所述有機層具有包含下述式（1）所表示的芳香族化合物的層。 <1> An organic electroluminescence element having an anode and a cathode on a substrate, an organic layer between the anode and the cathode, and in the organic electroluminescence element, The organic layer has a layer containing an aromatic compound represented by the following formula (1).

[化2]

[Chem 2]

（式（1）中， Ar ¹～Ar ⁵各自獨立地為氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基， Ar ¹、Ar ²及Ar ⁵的至少一個由下述式（2）或下述式（3）表示。 L ¹～L ⁵各自獨立地為可具有取代基的二價的碳數6以上且60以下的芳香族烴基。 R各自獨立地表示烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。 m1、m2及m5各自獨立地表示0～5的整數。 m3及m4各自獨立地表示1～5的整數。 n表示0～10的整數。 a1及a2各自獨立地表示0～3的整數。 a3表示0～4的整數。 a4表示0或1的整數。其中，於a3為4的情況下a4為0。於Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基各自獨立地為烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。式（1）中，Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ³-(L ³) _m3-、Ar ⁴-(L ⁴) _m4-均不成為氫原子。） (In formula (1), Ar ¹ to Ar ⁵ are each independently a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have substituents, and at least one of Ar ¹ , Ar ² and Ar ⁵ Represented by the following formula (2) or the following formula (3). L ¹ to L ⁵ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms that may have a substituent. R each independently represents Alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkoxycarbonyl, acyl, halogen atom, haloalkyl, alkylthio, arylthio, silyl, siloxy, aralkyl, or an aromatic hydrocarbon group. m1, m2 and m5 each independently represent an integer of 0 to 5. m3 and m4 each independently represent an integer of 1 to 5. n represents an integer of 0 to 10. a1 and a2 each independently represent an integer of 0 to 5 An integer of 3. a3 represents an integer of 0 to 4. a4 represents an integer of 0 or 1. However, when a3 is 4, a4 is 0. Among Ar ¹ to Ar ⁵ , the number of monovalent carbon atoms is 6 or more and 60 or less The substituents that the aromatic hydrocarbon groups in L 1 to L 5 may have, and the substituents that the divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms in L ¹ to L ⁵ are each independently an alkyl group, an alkenyl group, an alkynyl group, an alkane group, Oxygen group, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group. In the formula (1) , Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ³ -(L ³ ) _m3 -, Ar ⁴ -(L ⁴ ) _m4 - are not hydrogen atoms.)

[化3]

[Chem 3]

（式（2）或式（3）中，星號（*）表示與式（1）的鍵。 R ¹～R ²⁶各自獨立地表示氫原子、烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。） (In formula (2) or formula (3), an asterisk (*) represents a bond with formula (1). R ¹ to R ²⁶ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, Aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxy group, aralkyl group, or aromatic hydrocarbon group.)

＜2＞如＜1＞所述的有機電場發光元件，其中Ar ¹及Ar ²、與n為1以上時的Ar ⁵或n為2以上時的至少一個Ar ⁵由所述式（2）或所述式（3）表示。 <2> The organic electroluminescent device as described in <1>, wherein Ar ¹ and Ar ² , and Ar ⁵ when n is 1 or more, or at least one Ar ⁵ when n is 2 or more are expressed by the formula (2) or Said formula (3) represents.

＜3＞如＜1＞或＜2＞所述的有機電場發光元件，其中L ¹～L ⁵各自獨立地為可具有取代基的伸苯基或將伸苯基連結兩個以上而成的基。 <3> The organic electroluminescence device as described in <1> or <2>, wherein L ¹ to L ⁵ are each independently an optionally substituted phenylene group or a group in which two or more phenylene groups are linked. .

＜4＞如＜3＞所述的有機電場發光元件，其中L ¹～L ⁵各自獨立地為可具有取代基的1,3-伸苯基。 <4> The organic electroluminescent device according to <3>, wherein L ¹ to L ⁵ are each independently a 1,3-phenylene group which may have a substituent.

＜5＞如＜1＞至＜4＞中任一項所述的有機電場發光元件，其中所述芳香族化合物的分子量為1200以上。<5> The organic electroluminescent device according to any one of <1> to <4>, wherein the molecular weight of the aromatic compound is 1200 or more.

＜6＞如＜1＞至＜5＞中任一項所述的有機電場發光元件，其中包含所述芳香族化合物的層為發光層。<6> The organic electroluminescent device according to any one of <1> to <5>, wherein the layer containing the aromatic compound is a light emitting layer.

＜7＞一種顯示裝置，具有如＜1＞至＜6＞中任一項所述的有機電場發光元件。<7> A display device comprising the organic electroluminescent element according to any one of <1> to <6>.

＜8＞一種照明裝置，具有如＜1＞至＜6＞中任一項所述的有機電場發光元件。<8> A lighting device comprising the organic electroluminescent element according to any one of <1> to <6>.

＜9＞一種芳香族化合物，由下述式（1）表示。<9> An aromatic compound represented by the following formula (1).

[化4]

[chemical 4]

（式（1）中， Ar ¹～Ar ⁵各自獨立地為氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基， Ar ¹、Ar ²及Ar ⁵的至少一個由下述式（2）或下述式（3）表示。 L ¹～L ⁵各自獨立地為可具有取代基的二價的碳數6以上且60以下的芳香族烴基。 R各自獨立地表示烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基。 m1、m2及m5各自獨立地表示0～5的整數。 m3及m4各自獨立地表示1～5的整數。 n表示0～10的整數。 a1及a2各自獨立地表示0～3的整數。 a3表示0～4的整數。 a4表示0或1的整數。其中，於a3為4的情況下a4為0。於Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基各自獨立地為烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基。式（1）中，Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ³-(L ³) _m3-、Ar ⁴-(L ⁴) _m4-均不成為氫原子。） (In formula (1), Ar ¹ to Ar ⁵ are each independently a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have substituents, and at least one of Ar ¹ , Ar ² and Ar ⁵ Represented by the following formula (2) or the following formula (3). L ¹ to L ⁵ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms that may have a substituent. R each independently represents Alkyl group, alkenyl group, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group. m1, m2 and m5 each independently represent 0 An integer of ∼5. m3 and m4 each independently represent an integer of 1 to 5. n represents an integer of 0 to 10. a1 and a2 each independently represent an integer of 0 to 3. a3 represents an integer of 0 to 4. a4 represents 0 or an integer of 1. However, when a3 is 4, a4 is 0. A substituent that a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms in Ar ¹ to Ar ⁵ may have, and L ¹ to L The substituents that the divalent aromatic hydrocarbon group having 6 to 60 carbon atoms in ⁵ are each independently an alkyl group, an alkenyl group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, and a silane group, siloxy group, aralkyl group, or aromatic hydrocarbon group. In formula (1), Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ³ -(L ³ ) _m3 - , Ar ⁴ -(L ⁴ ) _m4 - are not hydrogen atoms.)

[化5]

[chemical 5]

（式（2）或式（3）中，星號（*）表示與式（1）的鍵。 R ¹～R ²⁶各自獨立地表示氫原子、烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基。） (In formula (2) or formula (3), an asterisk (*) represents a bond with formula (1). R ¹ to R ²⁶ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryloxy group, an alkoxy group carbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group.)

＜10＞如＜9＞所述的芳香族化合物，其中a1、a2及a4為0。<10> The aromatic compound as described in <9> whose a1, a2, and a4 are 0.

＜11＞如＜9＞所述的芳香族化合物，其中a4為1，a3為0～3的整數。<11> The aromatic compound as described in <9> whose a4 is 1, and a3 is an integer of 0-3.

＜12＞如＜11＞所述的芳香族化合物，其中a1、a2及a3相同。<12> The aromatic compound according to <11>, wherein a1, a2, and a3 are the same.

＜13＞如＜9＞至＜12＞中任一項所述的芳香族化合物，其中Ar ¹及Ar ²、與n為1以上時的Ar ⁵或n為2以上時的至少一個Ar ⁵由所述式（2）或所述式（3）表示。 <13> The aromatic compound according to any one of <9> to <12>, wherein Ar ¹ and Ar ² , and Ar ⁵ when n is 1 or more or at least one Ar ⁵ when n is 2 or more are composed of Said formula (2) or said formula (3) represents.

＜14＞如＜9＞至＜13＞中任一項所述的芳香族化合物，其中L ¹～L ⁵各自獨立地為可具有取代基的伸苯基或將伸苯基連結兩個以上而成的基。 <14> The aromatic compound according to any one of <9> to <13>, wherein L ¹ to L ⁵ are each independently an optionally substituted phenylene group or two or more phenylene groups linked together. into the base.

＜15＞如＜14＞所述的芳香族化合物，其中L ¹～L ⁵各自獨立地為可具有取代基的1,3-伸苯基。 <15> The aromatic compound according to <14>, wherein L ¹ to L ⁵ are each independently a 1,3-phenylene group which may have a substituent.

＜16＞如＜9＞至＜15＞中任一項所述的芳香族化合物，其中分子量為1200以上。<16> The aromatic compound according to any one of <9> to <15>, which has a molecular weight of 1200 or more.

＜17＞一種組成物，含有如＜9＞至＜16＞中任一項所述的芳香族化合物及有機溶劑。<17> A composition containing the aromatic compound and an organic solvent according to any one of <9> to <16>.

＜18＞如＜17＞所述的組成物，更含有磷光發光材料及電荷傳輸材料。<18> The composition according to <17>, further comprising a phosphorescent material and a charge transport material.

＜19＞如＜18＞所述的組成物，其中所述電荷傳輸材料包含下述式（250）所表示的化合物及/或下述式（240）所表示的化合物。<19> The composition according to <18>, wherein the charge transport material contains a compound represented by the following formula (250) and/or a compound represented by the following formula (240).

[化6]

[chemical 6]

（式（250）中， W各自獨立地表示CH或N，至少一個W為N。 Xa ¹、Ya ¹、及Za ¹各自獨立地表示可具有取代基的碳數6～30的二價芳香族烴基、或可具有取代基的碳數3～30的二價芳香族雜環基。 Xa ²、Ya ²及Za ²各自獨立地表示氫原子、可具有取代基的碳數6～30的一價芳香族烴基、或可具有取代基的碳數3～30的一價芳香族雜環基。 g11、h11、及j11各自獨立地表示0～6的整數， g11、h11、j11的至少一個為1以上的整數。於g11為2以上的情況下，存在多個的Xa ¹可相同亦可不同。於h11為2以上的情況下，存在多個的Ya ¹可相同亦可不同。於j11為2以上的情況下，存在多個的Za ¹可相同亦可不同。 R ³¹表示氫原子或取代基，四個R ³¹可相同亦可不同。其中，於g11、h11、或j11為0的情況下，分別對應的Xa ²、Ya ²、Za ²不為氫原子。） (In formula (250), W each independently represents CH or N, and at least one W is N. Xa ¹ , Ya ¹ , and Za ¹ each independently represent a divalent aromatic group having 6 to 30 carbon atoms that may have a substituent A hydrocarbon group ^, ^or a divalent ^aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent. An aromatic hydrocarbon group, or a monovalent aromatic heterocyclic group having 3 to 30 carbon atoms that may have a substituent. g11, h11, and j11 each independently represent an integer of 0 to 6, and at least one of g11, h11, and j11 is 1 An integer of the above. When g11 is 2 or more, plural Xa ^1s may be the same or different. When h11 is 2 or more, plural Ya ^1s may be the same or different. When j11 is 2 In the above case, there are multiple Za ^1s that may be the same or different. R ³¹ represents a hydrogen atom or a substituent, and the four R ^31s may be the same or different. Among them, when g11, h11, or j11 is 0 , the corresponding Xa ² , Ya ² , Za ² are not hydrogen atoms.)

[化7]

[chemical 7]

（式（240）中， Ar ⁶¹¹、Ar ⁶¹²各自獨立地表示可具有取代基的碳數6～50的一價芳香族烴基。 R ⁶¹¹、R ⁶¹²各自獨立地表示氘原子、鹵素原子、或可具有取代基的碳數6～50的一價芳香族烴基。 G表示單鍵、或可具有取代基的碳數6～50的二價芳香族烴基。 n ⁶¹¹、n ⁶¹²各自獨立地為0～4的整數。） (In formula (240), Ar ⁶¹¹ and Ar ⁶¹² each independently represent a monovalent aromatic hydrocarbon group with 6 to 50 carbon atoms that may have substituents. R ⁶¹¹ and R ⁶¹² each independently represent a deuterium atom, a halogen atom, or a A monovalent aromatic hydrocarbon group with a carbon number of 6 to 50 having a substituent. G represents a single bond or a divalent aromatic hydrocarbon group with a carbon number of 6 to 50 that may have a substituent. n ⁶¹¹ and n ⁶¹² are each independently 0 to Integer of 4.)

＜20＞如＜19＞所述的組成物，其中所述式（250）中的三個W中的至少兩個為N。<20> The composition according to <19>, wherein at least two of the three Ws in the formula (250) are N.

＜21＞如＜20＞所述的組成物，其中所述式（250）中的W全部為N。<21> The composition according to <20>, wherein all W in the formula (250) are N.

＜22＞如＜19＞所述的組成物，其中所述式（240）中的Ar ⁶¹¹及Ar ⁶¹²各自獨立地為可具有取代基的多個苯環以鏈狀或分支的方式鍵結而成的一價基。 <22> The composition according to <19>, wherein Ar ⁶¹¹ and Ar ⁶¹² in the formula (240) are each independently a plurality of benzene rings which may have substituents bonded in a chain or branched form. into a monovalent basis.

＜23＞如＜19＞所述的組成物，其中所述式（240）中的R ⁶¹¹及R ⁶¹²各自獨立地為可具有取代基的碳數6～30的一價芳香族烴基。 <23> The composition according to <19>, wherein R ⁶¹¹ and R ⁶¹² in the formula (240) are each independently a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent.

＜24＞如＜19＞所述的組成物，其中所述式（240）中的n ⁶¹¹及n ⁶¹²各自獨立地為0或1。 <24> The composition according to <19>, wherein n ⁶¹¹ and n ⁶¹² in the formula (240) are 0 or 1 each independently.

＜25＞一種薄膜形成方法，具有利用濕式成膜法將如＜17＞至＜24＞中任一項所述的組成物成膜的步驟。<25> A thin film forming method comprising the step of forming a film of the composition according to any one of <17> to <24> by a wet film forming method.

＜26＞一種有機電場發光元件的製造方法，其中所述有機電場發光元件於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件的製造方法中，具有使用如＜17＞至＜24＞中任一項所述的組成物並利用濕式成膜法形成所述有機層的步驟。 <26> A method for manufacturing an organic electroluminescent element, wherein the organic electroluminescent element has an anode and a cathode on a substrate, and an organic layer is provided between the anode and the cathode, and the method for manufacturing the organic electroluminescent element middle, There is a step of forming the organic layer by a wet film-forming method using the composition described in any one of <17> to <24>.

＜27＞如＜26＞所述的有機電場發光元件的製造方法，其中所述有機層為發光層。<27> The method for producing an organic electroluminescence device according to <26>, wherein the organic layer is a light-emitting layer.

＜28＞一種有機電場發光元件的製造方法，其中所述有機電場發光元件於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件的製造方法中，所述有機層包含發光層與電子傳輸層，包括：使用如＜17＞至＜24＞中任一項所述的組成物並利用濕式成膜法形成所述發光層的步驟；以及使用包含電子傳輸材料及溶劑的電子傳輸層形成用組成物並利用濕式成膜法形成所述電子傳輸層的步驟。 <28> A method for manufacturing an organic electroluminescent element, wherein the organic electroluminescent element has an anode and a cathode on a substrate, and an organic layer is provided between the anode and the cathode, and the method for manufacturing the organic electroluminescent element middle, The organic layer includes a light emitting layer and an electron transport layer, Including: using the composition described in any one of <17> to <24> and using a wet film-forming method to form the light-emitting layer; and A step of forming the electron transport layer by a wet film-forming method using a composition for forming an electron transport layer including an electron transport material and a solvent.

＜29＞如＜28＞所述的有機電場發光元件的製造方法，其中所述電子傳輸層形成用組成物中包含的溶劑為醇系溶劑。<29> The method for producing an organic electroluminescence device according to <28>, wherein the solvent contained in the composition for forming an electron transport layer is an alcohol-based solvent.

＜30＞一種有機電場發光元件，於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件中，所述有機層包含發光層，所述發光層包含如＜9＞至＜16＞中任一項所述的芳香族化合物、磷光發光材料及電荷傳輸材料，所述電荷傳輸材料包含下述式（250）所表示的化合物及/或下述式（240）所表示的化合物。 <30> An organic electroluminescence element having an anode and a cathode on a substrate, an organic layer between the anode and the cathode, and in the organic electroluminescence element, The organic layer comprises a light-emitting layer, The light-emitting layer comprises an aromatic compound, a phosphorescent material and a charge transport material as described in any one of <9> to <16>, The charge transport material includes a compound represented by the following formula (250) and/or a compound represented by the following formula (240).

[化8]

[chemical 8]

[化9]

[chemical 9]

＜31＞如＜30＞所述的有機電場發光元件，其中所述式（250）中的三個W中的至少兩個為N。<31> The organic electroluminescent device according to <30>, wherein at least two of the three Ws in the formula (250) are N.

＜32＞如＜31＞所述的有機電場發光元件，其中所述式（250）中的W全部為N。 [發明的效果] <32> The organic electroluminescent device according to <31>, wherein all W in the formula (250) are N. [Effect of the invention]

根據本發明，可提供一種耐熱性、溶劑溶解性優異、並且帶隙大的芳香族化合物。本發明的芳香族化合物的針對薄膜中的醇系溶劑的耐溶劑性亦優異。因此，亦能夠利用濕式成膜法於包含本發明的芳香族化合物的膜上積層形成其他層。 According to the present invention, an aromatic compound having excellent heat resistance and solvent solubility and a large band gap can be provided. The aromatic compound of the present invention is also excellent in solvent resistance to alcohol-based solvents in the film. Therefore, it is also possible to form another layer by laminating on the film containing the aromatic compound of the present invention by a wet film-forming method.

根據本發明，可提供具有該芳香族化合物的有機電場發光元件、具有該有機電場發光元件的顯示裝置及照明裝置、含有該化合物及溶劑的組成物、薄膜形成方法及有機電場發光元件的製造方法。According to the present invention, there can be provided an organic electroluminescent device having the aromatic compound, a display device and a lighting device having the organic electroluminescent device, a composition containing the compound and a solvent, a method for forming a thin film, and a method for producing an organic electroluminescent device .

以下，對本發明的實施方式進行詳細說明。本發明並不限定於以下的實施方式，可於其主旨的範圍內進行各種變形來實施。Hereinafter, embodiments of the present invention will be described in detail. The present invention is not limited to the following embodiments, and various modifications can be made within the scope of the gist.

於本發明中，所謂「可具有取代基」，是指可具有一個以上的取代基。In the present invention, "may have a substituent" means that it may have one or more substituents.

[本發明的芳香族化合物] 本發明的有機電場發光元件所具有的有機層中包含的芳香族化合物為下述式（1）所表示的芳香族化合物（以下，有時稱為「芳香族化合物（1）」）。 [Aromatic compound of the present invention] The aromatic compound contained in the organic layer included in the organic electroluminescence device of the present invention is an aromatic compound represented by the following formula (1) (hereinafter, may be referred to as "aromatic compound (1)").

[化10]

[chemical 10]

[化11]

[chemical 11]

＜芳香族化合物（1）的作用機理＞於本發明中，藉由芳香族化合物（1）而獲得有效的效果的作用機理推測如以下般。＜Aromatic compound (1) mechanism of action＞ In the present invention, the mechanism by which the effective effect is obtained by the aromatic compound (1) is presumed as follows.

芳香族化合物（1）由於具有一個以上的式（2）或式（3）所表示的於對位進行了鍵結的三聯苯基，因此玻璃轉移溫度高。式（2）或式（3）所表示的於對位進行了鍵結的三聯苯基於鄰位或間位與式（1）鍵結，藉此抑制π共軛系的擴展，帶隙變大，激發三重態能階（T1）變高，溶解性高而結晶性變低。 Since the aromatic compound (1) has one or more terphenyl groups bonded at the para position represented by the formula (2) or the formula (3), it has a high glass transition temperature. The terphenyl group bonded at the para position represented by formula (2) or formula (3) is bonded to formula (1) at the ortho or meta position, thereby suppressing the expansion of the π conjugated system and increasing the band gap , the excited triplet energy level (T1) becomes higher, the solubility is higher and the crystallinity becomes lower.

藉由式（1）所表示的芳香族烴結構具有式（2）或式（3）所表示的於對位進行了鍵結的三聯苯基，可提高薄膜的對醇系溶劑的耐溶劑性。藉由式（1）所表示的芳香族烴結構具有式（2）或式（3）所表示的於對位進行了鍵結的三聯苯基，最高佔有分子軌域（highest occupied molecular orbital，HOMO）、最低未佔有分子軌域（lowest unoccupied molecular orbital，LUMO）容易局部存在於式（2）或式（3）所表示的於對位進行了鍵結的三聯苯基，可提高耐久性。 The aromatic hydrocarbon structure represented by formula (1) has a terphenyl group bonded at the para position represented by formula (2) or formula (3), which can improve the solvent resistance of the film to alcohol-based solvents . The aromatic hydrocarbon structure represented by formula (1) has a terphenyl group bonded at the para position represented by formula (2) or formula (3), and the highest occupied molecular orbital (highest occupied molecular orbital, HOMO ), the lowest unoccupied molecular orbital (lowest unoccupied molecular orbital, LUMO) tends to partially exist in the terphenyl group bonded to the para position represented by formula (2) or formula (3), and durability can be improved.

使用芳香族化合物（1），可容易地提供驅動穩定性優異、且能夠以低驅動電壓及高效率驅動的有機電場發光元件。Using the aromatic compound (1) can easily provide an organic electroluminescent device that is excellent in drive stability and can be driven with low drive voltage and high efficiency.

包含芳香族化合物（1）的本發明的有機電場發光元件的電化學穩定性優異，驅動電壓低且為高效率。因此，可考慮將本發明的有機電場發光元件應用於平板顯示器（例如，辦公室自動化（office automation，OA）電腦用顯示器或壁掛電視機）、車載顯示元件、行動電話顯示或活用作為面發光體的特徵的光源（例如，複印機的光源、液晶顯示器或儀表類的背光光源）、顯示板、標識燈，其技術價值大。The organic electroluminescent device of the present invention containing the aromatic compound (1) has excellent electrochemical stability, low driving voltage, and high efficiency. Therefore, it is conceivable to apply the organic electroluminescent element of the present invention to flat panel displays (for example, office automation (office automation, OA) computer monitors or wall-mounted TVs), vehicle display elements, mobile phone displays, or as surface light emitters. Characteristic light sources (for example, light sources of copiers, backlights of liquid crystal displays or instruments), display panels, and identification lights have great technical value.

＜Ar ¹、Ar ²、Ar ⁵＞ Ar ¹、Ar ²及Ar ⁵各自獨立地為氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基。 Ar ¹、Ar ²及Ar ⁵的至少一個由下述式（2）或下述式（3）表示。就穩定性的觀點而言，Ar ¹、Ar ²及Ar ⁵較佳為各自獨立地為式（3）所表示的結構。 <Ar ¹ , Ar ² , Ar ⁵ > Ar ¹ , Ar ^{2 ,} and Ar ⁵ are each independently a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent. At least one of Ar ¹ , Ar ² and Ar ⁵ is represented by the following formula (2) or the following formula (3). From the viewpoint of stability, Ar ¹ , Ar ² , and Ar ⁵ are each independently preferably a structure represented by formula (3).

[化12]

[chemical 12]

就化合物的溶解性、耐久性的觀點而言，Ar ¹、Ar ²及Ar ⁵較佳為氫原子、苯環的一價基、萘環的一價基、所述式（2）或式（3）所表示的結構，更佳為氫原子、苯環的一價基、所述式（2）或式（3）所表示的結構，進而佳為氫原子、苯環的一價基、所述式（3）所表示的結構，最佳為所述式（3）所表示的結構。 In terms of the solubility and durability of the compound, Ar ¹ , Ar ² and Ar ⁵ are preferably a hydrogen atom, a monovalent group of a benzene ring, a monovalent group of a naphthalene ring, the formula (2) or the formula ( 3) The structure represented is more preferably a hydrogen atom, a monovalent group of a benzene ring, the structure represented by the formula (2) or formula (3), further preferably a hydrogen atom, a monovalent group of a benzene ring, the The structure represented by the above formula (3) is preferably the structure represented by the above formula (3).

就耐久性的觀點而言，Ar ¹及Ar ²、與n為1以上時的Ar ⁵或n為2以上時的至少一個Ar ⁵較佳為所述式（2）或所述式（3）所表示的結構，該些特佳為所述式（3）所表示的結構。 From the viewpoint of durability, Ar ¹ and Ar ² , and Ar ⁵ when n is 1 or more, or at least one Ar ⁵ when n is 2 or more are preferably the formula (2) or the formula (3) Among the structures represented, these structures are particularly preferably represented by the formula (3).

＜Ar ³、Ar ⁴＞ Ar ³及Ar ⁴各自獨立地表示氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基。 <Ar ³ , Ar ⁴ > Ar ³ and Ar ⁴ each independently represent a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.

作為一價的碳數6以上且60以下的芳香族烴基的例子，可列舉苯環、萘環、蒽環、菲環、四伸苯環、䓛環、芘環、苯並蒽環、苝環、聯苯環、或三聯苯環的一價基。Examples of monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, tetraphenylene rings, phenanthrene rings, pyrene rings, benzoanthracene rings, and perylene rings. , a biphenyl ring, or a monovalent group of a terphenyl ring.

就化合物的溶解性、耐久性的觀點而言，Ar ³、Ar ⁴較佳為各自獨立地為氫原子、苯環的一價基、萘環的一價基，更佳為氫原子、苯環的一價基。 From the viewpoint of the solubility and durability of the compound, Ar ³ and Ar ⁴ are each independently preferably a hydrogen atom, a monovalent group of a benzene ring, or a monovalent group of a naphthalene ring, more preferably a hydrogen atom, a benzene ring, or a monovalent group of a naphthalene ring. the one-price basis.

＜L ¹～L ⁵＞ L ¹～L ⁵各自獨立地表示可具有取代基的二價的碳數6以上且60以下的芳香族烴基。 <L ¹ to L ⁵ > L ¹ to L ⁵ each independently represent a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.

作為二價的碳數6以上且60以下的芳香族烴環的例子，可列舉苯環、萘環、蒽環、四伸苯環、菲環、䓛環、芘環、苯並蒽環、或苝環、或者該些芳香族烴環的兩個以上藉由直接鍵結而連結的二價基。Examples of divalent aromatic hydrocarbon rings having 6 to 60 carbon atoms include benzene rings, naphthalene rings, anthracene rings, tetraphenylene rings, phenanthrene rings, phenanthrene rings, pyrene rings, benzanthracene rings, or A perylene ring, or a divalent group in which two or more of these aromatic hydrocarbon rings are linked by direct bonding.

L ¹～L ⁵較佳為各自獨立地為可具有取代基的伸苯基或伸苯基藉由兩個以上、例如兩個～五個直接鍵結而連結的二價基，就溶解性的觀點而言，更佳為可具有取代基的1,3-伸苯基。 L ¹ to L ⁵ are each independently preferably a phenylene group which may have a substituent or a divalent group in which the phenylene group is linked by two or more, for example, two to five direct bonds. From a viewpoint, a 1,3-phenylene group which may have a substituent is more preferable.

＜R＞ R各自獨立地表示烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。關於該些取代基的具體例及較佳的結構，於後述揭示的取代基群組Z中記載。 <R> R each independently represent an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, silyloxy group , Aralkyl, or aromatic hydrocarbon. Specific examples and preferred structures of these substituents are described in Substituent Group Z disclosed later.

就耐熱性及耐久性的觀點而言，R較佳為各自獨立地為烷基、烯基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、芳香族烴基，更佳為烷基、烷氧基、芳烷基、芳香族烴基，進而佳為碳數10以下的烷基、碳數30以下的芳烷基、碳數30以下的芳香族烴基，特佳為苯環或苯環藉由兩個～五個直接鍵結而連結的基。In terms of heat resistance and durability, R is preferably each independently an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, Siloxyl group, aralkyl group, aromatic hydrocarbon group, more preferably alkyl group, alkoxyl group, aralkyl group, aromatic hydrocarbon group, further preferably alkyl group having 10 or less carbon atoms, aralkyl group having 30 or less carbon atoms, The aromatic hydrocarbon group having 30 or less carbon atoms is particularly preferably a benzene ring or a group in which benzene rings are linked by two to five direct bonds.

＜m1～m5＞ m1、m2及m5各自獨立地表示0～5的整數， m3、m4各自獨立地表示1～5的整數。＜m1～m5＞ m1, m2, and m5 each independently represent an integer of 0 to 5, m3 and m4 each independently represent the integer of 1-5.

就化合物的溶解性、及耐久性的觀點而言，m1、m2及m5較佳為4以下，更佳為3以下，進而佳為2以下，特佳為1以下，最佳為0。From the viewpoint of the solubility and durability of the compound, m1, m2, and m5 are preferably 4 or less, more preferably 3 or less, still more preferably 2 or less, particularly preferably 1 or less, most preferably 0.

就化合物的溶解性、及耐久性的觀點而言，m3、m4為1以上，較佳為4以下，進而佳為3以下，特佳為2以下。From the viewpoint of the solubility and durability of the compound, m3 and m4 are 1 or more, preferably 4 or less, further preferably 3 or less, particularly preferably 2 or less.

於m1為2以上的情況下，多個L ¹可相同亦可不同。於m2為2以上的情況下，多個L ²可相同亦可不同。於m3為2以上的情況下，多個L ³可相同亦可不同。於m4為2以上的情況下，多個L ⁴可相同亦可不同。於m5為2以上的情況下，多個L ⁵可相同亦可不同。 When m1 is 2 or more, a plurality of ^L1 may be the same or different. When m2 is 2 or more, a plurality of ^L2 may be the same or different. When m3 is 2 or more, a plurality of ^L3 may be the same or different. When m4 is 2 or more, a plurality of ^L4 may be the same or different. When m5 is 2 or more, a plurality of ^L5 may be the same or different.

＜Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ⁵-(L ⁵) _m5-＞就化合物的耐久性的觀點而言，Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ⁵-(L ⁵) _m5-較佳為至少一個為所述式（2）或式（3）所表示的結構，更佳為至少一個為所述式（3）所表示的結構，進而佳為至少兩個為所述式（3）所表示的結構，進而更佳為至少三個為所述式（3）所表示的結構，特佳為全部為所述式（3）所表示的結構。 Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ³-(L ³) _m3-、Ar ⁴-(L ⁴) _m4-均不成為氫原子。 <Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ⁵ -(L ⁵ ) _m5 -> From the viewpoint of the durability of the compound, Ar ¹ -(L ¹ ) _m1 - , Ar ² -(L ² ) _m2 -, Ar ⁵ -(L ⁵ ) _m5 - preferably at least one of the structures represented by the formula (2) or formula (3), more preferably at least one of the structures represented by the The structure represented by the formula (3), preferably at least two structures represented by the formula (3), more preferably at least three structures represented by the formula (3), particularly preferably all It is the structure represented by said formula (3). Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ³ -(L ³ ) _m3 -, and Ar ⁴ -(L ⁴ ) _m4 - do not become hydrogen atoms.

＜(L ³) _m3、(L ⁴) _m4＞就化合物的溶解性及耐久性的觀點而言，(L ³) _m3、及(L ⁴) _m4的至少一者較佳為具有選自下述式（11）所表示的部分結構、下述式（12）所表示的部分結構、及下述式（13）所表示的部分結構中的至少一個部分結構。 <(L ³ ) _m3 , (L ⁴ ) _m4 > From the viewpoint of compound solubility and durability, at least one of (L ³ ) _m3 and (L ⁴ ) _m4 preferably has a compound selected from the following: At least one partial structure among the partial structure represented by formula (11), the partial structure represented by the following formula (12), and the partial structure represented by the following formula (13).

[化13]

[chemical 13]

於所述式（11）～式（13）各個中，*表示與鄰接的結構的鍵或Ar ³、Ar ⁴為氫原子時的該氫原子。存在兩個的*中的至少一個表示與鄰接的結構的鍵結位置。於以後的記載中，只要無特別說明，則*的定義亦相同。 In each of the formulas (11) to (13), * represents a bond to an adjacent structure or a hydrogen atom when Ar ³ and Ar ⁴ are hydrogen atoms. At least one of two * indicates a bonding position with an adjacent structure. In the following description, unless otherwise specified, the definition of * is also the same.

更佳為(L ³) _m3及(L ⁴) _m4的至少一者具有式（11）所表示的部分結構或式（12）所表示的部分結構。進而佳為(L ³) _m3及(L ⁴) _m4分別具有式（11）所表示的部分結構或式（12）所表示的部分結構。特佳為(L ³) _m3及(L ⁴) _m4分別具有式（11）所表示的部分結構及式（12）所表示的部分結構。 More preferably, at least one of (L ³ ) _m3 and (L ⁴ ) _m4 has a partial structure represented by formula (11) or a partial structure represented by formula (12). Further preferably, (L ³ ) _m3 and (L ⁴ ) _m4 each have a partial structure represented by formula (11) or a partial structure represented by formula (12). Most preferably, (L ³ ) _m3 and (L ⁴ ) _m4 have a partial structure represented by formula (11) and a partial structure represented by formula (12), respectively.

作為式（12）所表示的部分結構，較佳為下述式（12-2）所表示的部分結構。The partial structure represented by the formula (12) is preferably a partial structure represented by the following formula (12-2).

[化14]

[chemical 14]

作為式（12）所表示的部分結構，進而更佳為下述式（12-3）所表示的部分結構。The partial structure represented by the formula (12) is more preferably a partial structure represented by the following formula (12-3).

[化15]

[chemical 15]

就化合物的溶劑溶解性及耐久性的觀點而言，作為(L ³) _m3及(L ⁴) _m4的至少一者較佳具有的部分結構，可列舉具有式（11）所表示的部分結構及式（12）所表示的部分結構的部分結構。 From the viewpoint of solvent solubility and durability of the compound, at least one of (L ³ ) _m3 and (L ⁴ ) _m4 preferably has a partial structure that has a partial structure represented by formula (11) and The partial structure of the partial structure represented by Formula (12).

作為具有式（11）所表示的部分結構及式（12）所表示的部分結構的部分結構，進而佳為包含多個選自式（11）所表示的部分結構及式（12）所表示的部分結構中的結構的結構、即選自下述式（14）～下述式（18）中的至少一個所表示的部分結構。As the partial structure having the partial structure represented by the formula (11) and the partial structure represented by the formula (12), it is preferable to include a plurality of partial structures selected from the partial structure represented by the formula (11) and the partial structure represented by the formula (12). The structure of the structure in the partial structure is a partial structure represented by at least one selected from the following formula (14) to the following formula (18).

[化16]

[chemical 16]

所謂包含多個選自式（11）所表示的部分結構及式（12）所表示的部分結構中的結構的結構，例如式（14）所表示的部分結構如下述式（14a）般，為可視為具有一個式（11）所表示的部分結構與兩個式（12）所表示的部分結構的部分結構。The so-called structure including a plurality of structures selected from the partial structure represented by the formula (11) and the partial structure represented by the formula (12), for example, the partial structure represented by the formula (14) is like the following formula (14a), which is It can be regarded as a partial structure having one partial structure represented by formula (11) and two partial structures represented by formula (12).

[化17]

[chemical 17]

進而佳為(L ³) _m3及(L ⁴) _m4的至少一者至少具有式（14）所表示的部分結構或式（15）所表示的部分結構。 Further preferably, at least one of (L ³ ) _m3 and (L ⁴ ) _m4 has at least a partial structure represented by formula (14) or a partial structure represented by formula (15).

作為式（14）所表示的部分結構，較佳為下述式（14-2）所表示的部分結構。As the partial structure represented by the formula (14), a partial structure represented by the following formula (14-2) is preferable.

[化18]

[chemical 18]

作為式（14）所表示的部分結構，進而佳為下述式（14-3）所表示的部分結構。The partial structure represented by the formula (14) is further preferably a partial structure represented by the following formula (14-3).

[化19]

[chemical 19]

作為式（15）所表示的部分結構，較佳為下述式（15-2）所表示的部分結構。As the partial structure represented by the formula (15), a partial structure represented by the following formula (15-2) is preferable.

[化20]

[chemical 20]

作為式（15）所表示的部分結構，進而佳為下述式（15-3）所表示的部分結構。The partial structure represented by the formula (15) is further preferably a partial structure represented by the following formula (15-3).

[化21]

[chem 21]

作為式（17）所表示的部分結構，較佳為下述式（17-2）所表示的部分結構。As the partial structure represented by the formula (17), a partial structure represented by the following formula (17-2) is preferable.

[化22]

[chem 22]

作為式（18）所表示的部分結構，較佳為下述式（18-2）所表示的部分結構。As the partial structure represented by the formula (18), a partial structure represented by the following formula (18-2) is preferable.

[化23]

[chem 23]

(L ³) _m3及(L ⁴) _m4的至少一者更佳為具有下述式（19）所表示的部分結構或下述式（20）所表示的部分結構作為包含式（13）所表示的部分結構的部分結構。 At least one of (L ³ ) _m3 and (L ⁴ ) _m4 preferably has a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) as including the partial structure represented by the formula (13) The partial structure of the partial structure.

[化24]

[chem 24]

於所述式（14）～式（20）各個中，*表示與鄰接的結構的鍵、或Ar ³、Ar ⁴為氫原子時的該氫原子。存在兩個的*中的至少一個表示與鄰接的結構的鍵結位置。 In each of the formulas (14) to (20), * represents a bond to an adjacent structure, or a hydrogen atom when Ar ³ and Ar ⁴ are hydrogen atoms. At least one of two * indicates a bonding position with an adjacent structure.

式（14）～式（20）所表示的部分結構中，較佳為式（14-3）所表示的部分結構及式（15-3）所表示的部分結構，進而佳為式（14-3）。Among the partial structures represented by formula (14) to formula (20), the partial structure represented by formula (14-3) and the partial structure represented by formula (15-3) are preferred, and the partial structure represented by formula (14- 3).

＜L ¹～L ⁵的較佳的部分結構＞式（1）中，L ¹～L ⁵較佳為具有式（12-3）所表示的部分結構、式（14-3）所表示的部分結構或式（15-3）所表示的部分結構。 <Preferable partial structures of L ¹ to L ⁵ > In formula (1), L ¹ to L ⁵ preferably have a partial structure represented by formula (12-3) or a moiety represented by formula (14-3). Structure or partial structure represented by formula (15-3).

＜n＞ n表示0～10的整數。就化合物的溶解性、及耐久性的觀點而言，n較佳為1以上，更佳為2以上，且較佳為6以下，更佳為5以下，特佳為4以下。 <n> n represents an integer of 0-10. From the viewpoint of the solubility and durability of the compound, n is preferably 1 or more, more preferably 2 or more, and is preferably 6 or less, more preferably 5 or less, particularly preferably 4 or less.

＜a1～a4＞ a1及a2各自獨立地表示0～3的整數。 a3表示0～4的整數。 a4表示0或1的整數。其中，於a3為4的情況下a4為0。就化合物的溶解性、及耐久性的觀點而言，a1～a4較佳為以下的組合。 a1=a2=a4=0、且a3=0～4的整數； a1=a2=a4=0、且a3=0或1； a1=a2=a3=a4=0； a4=1、且a1=a2=a3； a4=1、且a1～a3各自獨立地為0～3的整數； a4=1、且a1～a3各自獨立地為0或1； a4=1、且a1=a2=a3=0或1；進而佳為 a1=a2=a3=a4=0； a4=1、且a1=a2=a3=0。即，就化合物的溶解性、及耐久性的觀點而言，a1～a3較佳為各自獨立地為0或1，最佳為0。＜a1～a4＞ a1 and a2 each independently represent the integer of 0-3. a3 represents an integer of 0-4. a4 represents an integer of 0 or 1. However, when a3 is 4, a4 is 0. From the viewpoint of solubility and durability of the compound, a1 to a4 are preferably the following combinations. a1=a2=a4=0, and a3=an integer from 0 to 4; a1=a2=a4=0, and a3=0 or 1; a1=a2=a3=a4=0; a4=1, and a1=a2=a3; a4=1, and a1～a3 are each independently an integer of 0～3; a4=1, and a1～a3 are each independently 0 or 1; a4=1, and a1=a2=a3=0 or 1; Further better a1=a2=a3=a4=0; a4=1, and a1=a2=a3=0. That is, from the viewpoint of the solubility and durability of the compound, a1 to a3 are preferably each independently 0 or 1, most preferably 0.

＜R ¹～R ²⁶＞ R ¹～R ²⁶各自獨立地表示氫原子、烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。關於該些取代基的具體例及較佳的結構，於後述揭示的取代基群組Z中記載。 <R ¹ to R ²⁶ > R ¹ to R ²⁶ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, Alkylthio, arylthio, silyl, siloxy, aralkyl, or aromatic hydrocarbon. Specific examples and preferred structures of these substituents are described in Substituent Group Z disclosed later.

就耐久性的觀點而言，R ¹～R ²⁶較佳為各自獨立地為氫原子、烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基，更佳為氫原子、或芳香族烴基，特佳為氫原子。 From the viewpoint of durability, R ¹ to R ²⁶ are preferably each independently a hydrogen atom, an alkyl group, an alkenyl group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, A siloxy group, an aralkyl group, or an aromatic hydrocarbon group, more preferably a hydrogen atom, or an aromatic hydrocarbon group, particularly preferably a hydrogen atom.

＜取代基＞於Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基各自獨立地為烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基，較佳為各自獨立地為烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基。 <Substituents> Substituents that Ar ¹ to Ar ⁵ may have are monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms, and divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms in L ¹ to L ⁵ The substituents that the hydrocarbon group may have are each independently an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, A silyl group, a siloxyl group, an aralkyl group, or an aromatic hydrocarbon group, preferably each independently an alkyl group, an alkenyl group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, Siloxy, aralkyl, or aromatic hydrocarbon.

作為所述Ar ¹～Ar ⁵、L ¹～L ⁵可具有的取代基、所述R、及R ¹～R ²⁶，具體而言，可列舉下述取代基群組Z中記載的取代基。 As the substituents Ar ¹ to Ar ⁵ and L ¹ to L ⁵ may have, the R, and R ¹ to R ²⁶ , specifically, the substituents described in the following substituent group Z are exemplified.

＜取代基群組Z＞取代基群組Z為包含烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、氰基、芳烷基、及芳香族烴基的取代基群組。 <Substituent group Z> The substituent group Z includes alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkoxycarbonyl, acyl, halogen atom, haloalkyl, alkylthio, arylthio, silyl, silicon Substituent groups of oxy group, cyano group, aralkyl group, and aromatic hydrocarbon group.

作為烷基，例如可列舉：甲基；乙基；分支、直鏈或環狀的丙基；分支、直鏈或環狀的丁基；分支、直鏈或環狀的戊基；分支、直鏈或環狀的己基；分支、直鏈或環狀的辛基；分支、直鏈或環狀的壬基；分支、直鏈或環狀的十二烷基等碳數通常為1以上、較佳為4以上且通常為24以下、較佳為10以下的直鏈、分支、或環狀的烷基。就化合物的穩定性的觀點而言，較佳為甲基、乙基、分支、直鏈或環狀的丙基、分支、直鏈或環狀的丁基，特佳為分支的丙基。As the alkyl group, for example, a methyl group; an ethyl group; a branched, straight chain or cyclic propyl group; a branched, straight chain or cyclic butyl group; a branched, straight chain or cyclic pentyl group; Chain or cyclic hexyl; branched, straight-chain or cyclic octyl; branched, straight-chain or cyclic nonyl; Straight-chain, branched, or cyclic alkyl groups preferably at least 4 and usually at most 24, preferably at most 10. From the viewpoint of compound stability, methyl, ethyl, branched, linear or cyclic propyl, branched, linear or cyclic butyl are preferred, and branched propyl is particularly preferred.

作為烯基，例如可列舉乙烯基等碳數通常為2以上且通常為24以下、較佳為12以下的烯基。Examples of the alkenyl group include, for example, an alkenyl group having a carbon number of usually 2 or more and usually 24 or less, preferably 12 or less, such as a vinyl group.

作為炔基，例如可列舉乙炔基等碳數通常為2以上且通常為24以下、較佳為12以下的炔基。Examples of the alkynyl group include, for example, an alkynyl group having a carbon number of usually 2 or more and usually 24 or less, preferably 12 or less, such as an ethynyl group.

作為烷氧基，例如可列舉甲氧基、乙氧基等碳數通常為1以上且通常為24以下、較佳為12以下的烷氧基。Examples of the alkoxy group include alkoxy groups having a carbon number of usually 1 or more and usually 24 or less, preferably 12 or less, such as a methoxy group and an ethoxy group.

作為芳氧基，例如可列舉苯氧基、萘氧基、吡啶氧基等碳數通常為4以上、較佳為5以上且通常為36以下、較佳為24以下的芳氧基或雜芳氧基。Examples of the aryloxy group include aryloxy or heteroaryl groups having a carbon number of usually 4 or more, preferably 5 or more, and usually 36 or less, preferably 24 or less, such as phenoxy, naphthyloxy, and pyridyloxy. Oxygen.

作為烷氧基羰基，例如可列舉甲氧基羰基、乙氧基羰基等碳數通常為2以上且通常為24以下、較佳為12以下的烷氧基羰基。Examples of the alkoxycarbonyl group include alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl having a carbon number of usually 2 or more and usually 24 or less, preferably 12 or less.

作為醯基，例如可列舉乙醯基、苯甲醯基等碳數通常為2以上且通常為24以下、較佳為12以下的醯基。Examples of the acyl group include acyl groups having a carbon number of usually 2 or more and usually 24 or less, preferably 12 or less, such as an acetyl group and a benzoyl group.

作為鹵素原子，例如可列舉氟原子、氯原子等鹵素原子。As a halogen atom, halogen atoms, such as a fluorine atom and a chlorine atom, are mentioned, for example.

作為鹵代烷基，例如可列舉三氟甲基等碳數通常為1以上且通常為12以下、較佳為6以下的鹵代烷基。Examples of the haloalkyl group include, for example, a haloalkyl group having a carbon number of usually 1 or more and usually 12 or less, preferably 6 or less, such as trifluoromethyl.

作為烷硫基，例如可列舉甲硫基、乙硫基等碳數通常為1以上且通常為24以下、較佳為12以下的烷硫基。As the alkylthio group, for example, an alkylthio group having a carbon number of usually 1 or more and usually 24 or less, preferably 12 or less, such as a methylthio group and an ethylthio group, can be mentioned.

作為芳硫基，例如可列舉苯硫基、萘硫基、吡啶硫基等碳數通常為4以上、較佳為5以上且通常為36以下、較佳為24以下的芳硫基或雜芳硫基。Examples of the arylthio group include arylthio or heteroaryl having a carbon number of usually 4 or more, preferably 5 or more, and usually 36 or less, preferably 24 or less, such as phenylthio, naphthylthio, and pyridylthio. Sulfur base.

作為矽烷基，例如可列舉三甲基矽烷基、三苯基矽烷基等碳數通常為2以上、較佳為3以上且通常為36以下、較佳為24以下的矽烷基。Examples of the silyl group include trimethylsilyl groups, triphenylsilyl groups and other silyl groups having a carbon number of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less.

作為矽氧基，例如可列舉三甲基矽氧基、三苯基矽氧基等碳數通常為2以上、較佳為3以上且通常為36以下、較佳為24以下的矽氧基。As the siloxy group, for example, a siloxy group having a carbon number of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less, such as trimethylsilyloxy and triphenylsilyloxy, can be mentioned.

作為芳烷基，例如可列舉苄基、2-苯基乙基、2-苯基丙基-2-基、2-苯基丁基-2-基、3-苯基戊基-3-基、3-苯基-1-丙基、4-苯基-1-丁基、5-苯基-1-戊基、6-苯基-1-己基、7-苯基-1-庚基、8-苯基-1-辛基等碳數通常為7以上、較佳為9以上且通常為30以下、較佳為18以下、進而佳為10以下的芳烷基。Examples of the aralkyl group include benzyl, 2-phenylethyl, 2-phenylpropyl-2-yl, 2-phenylbutyl-2-yl, 3-phenylpentyl-3-yl , 3-phenyl-1-propyl, 4-phenyl-1-butyl, 5-phenyl-1-pentyl, 6-phenyl-1-hexyl, 7-phenyl-1-heptyl, An aralkyl group having a carbon number of usually 7 or more, preferably 9 or more, and usually 30 or less, preferably 18 or less, and more preferably 10 or less, such as 8-phenyl-1-octyl.

作為芳香族烴基，例如可列舉苯環、萘環、蒽環、四伸苯環、菲環、䓛環、芘環、苯並蒽環、或苝環等的碳數通常為6以上且通常為30以下、較佳為18以下、進而佳為10以下的芳香族烴基。Examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a phenylene ring, a phenanthrene ring, a phenanthracene ring, a pyrene ring, a benzoanthracene ring, or a perylene ring, etc. The carbon number is usually 6 or more and usually 6 or more. 30 or less, preferably 18 or less, more preferably 10 or less aromatic hydrocarbon groups.

所述取代基群組Z中，較佳為烷基、烷氧基、芳烷基、芳香族烴基，更佳為碳數10以下的烷基、碳數30以下的芳烷基、碳數30以下的芳香族烴基，進而佳為碳數30以下的芳香族烴基，特佳為不具有取代基。In the substituent group Z, it is preferably an alkyl group, an alkoxy group, an aralkyl group, and an aromatic hydrocarbon group, and more preferably an alkyl group with 10 or less carbons, an aralkyl group with 30 or fewer carbons, or an aralkyl group with 30 or fewer carbons. The following aromatic hydrocarbon groups are more preferably aromatic hydrocarbon groups having 30 or less carbon atoms, and particularly preferably have no substituent.

所述取代基群組Z的各取代基亦可更具有取代基。作為該些的進一步的取代基，可使用與所述取代基（取代基群組Z）相同的取代基。所述取代基群組Z的取代基較佳為不具有進一步的取代基。Each substituent of the substituent group Z may further have a substituent. As these further substituents, the same substituents as those described above (substituent group Z) can be used. The substituents of the substituent group Z preferably have no further substituents.

＜分子量＞芳香族化合物（1）的分子量較佳為1000以上，更佳為1100以上，特佳為1200以上，最佳為1300以上，且較佳為5000以下，更佳為4000以下，特佳為3000以下，最佳為2000以下。＜Molecular Weight＞ The molecular weight of the aromatic compound (1) is preferably at least 1,000, more preferably at least 1,100, most preferably at least 1,200, most preferably at least 1,300, and is preferably at most 5,000, more preferably at most 4,000, and most preferably at most 3,000 , preferably below 2000.

＜具體例＞以下示出芳香族化合物（1）的具體例，但本發明並不限定於該些。＜Concrete example＞ Specific examples of the aromatic compound (1) are shown below, but the present invention is not limited thereto.

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＜芳香族化合物（1）的製造方法＞芳香族化合物（1）例如可按照實施例中記載的方法來製造。＜Method for producing aromatic compound (1)＞ The aromatic compound (1) can be produced, for example, according to the method described in the Examples.

＜芳香族化合物（1）的用途＞芳香族化合物（1）較佳為用於有機電場發光元件的有機層，作為該有機層，較佳為發光層。於將芳香族化合物（1）用於發光層的情況下，較佳為用作發光層的主體材料。＜Applications of aromatic compounds (1)＞ The aromatic compound (1) is preferably used in an organic layer of an organic electroluminescent device, and the organic layer is preferably a light-emitting layer. When the aromatic compound (1) is used for the light-emitting layer, it is preferably used as a host material of the light-emitting layer.

包含芳香族化合物（1）的有機層可利用蒸鍍法形成，亦可利用濕式成膜法形成。包含芳香族化合物（1）的有機層可形成更均勻的膜，因此特佳為利用濕式成膜法來形成。The organic layer containing the aromatic compound (1) may be formed by a vapor deposition method, or may be formed by a wet film-forming method. Since an organic layer containing an aromatic compound (1) can form a more uniform film, it is especially preferable to form it by the wet film-forming method.

[本發明的芳香族化合物] 本發明的芳香族化合物是下述式（1）所表示的芳香族化合物，是芳香族化合物（1）的一形態。 [Aromatic compound of the present invention] The aromatic compound of the present invention is an aromatic compound represented by the following formula (1), and is an aspect of the aromatic compound (1).

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本發明的芳香族化合物中，式（1）中的R、Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基、式（2）、式（3）中的R ¹～R ²⁶較芳香族化合物（1）中的該些而言更受限定，除此以外，與芳香族化合物（1）相同，適用所述芳香族化合物（1）中的說明。關於本發明的芳香族化合物的較佳形態、具體例亦與芳香族化合物（1）中的較佳形態、具體例相同。 In the aromatic compound of the present invention, R in formula (1), a substituent that a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms among Ar ¹ to Ar ⁵ may have, and two of L ¹ to L ⁵ The substituents that an aromatic hydrocarbon group with a valence of 6 to 60 carbon atoms may have, R ¹ to R ²⁶ in formula (2) and formula (3) are more popular than those in aromatic compound (1). Except for the limitation, the same as the aromatic compound (1), and the description in the above-mentioned aromatic compound (1) applies. The preferred form and specific examples of the aromatic compound of the present invention are also the same as those of the aromatic compound (1).

[組成物] 於對包含本發明的芳香族化合物的有機層進行濕式成膜法的情況下，至少對包含所述式（1）所表示的本發明的芳香族化合物及有機溶劑的組成物進行濕式成膜。本發明的組成物至少包含本發明的芳香族化合物及有機溶劑。本發明的組成物中可僅包含本發明的芳香族化合物中的一種，亦可包含兩種以上。本發明的組成物較佳為更包含發光材料，較佳為磷光發光材料與電荷傳輸材料。本發明的組成物可較佳地用作有機電場發光元件的發光層形成用組成物。 [composition] In the case of performing a wet film-forming method on the organic layer containing the aromatic compound of the present invention, at least the composition containing the aromatic compound of the present invention represented by the formula (1) and an organic solvent is wet-formed. membrane. The composition of the present invention contains at least the aromatic compound of the present invention and an organic solvent. The composition of the present invention may contain only one kind of aromatic compounds of the present invention, or may contain two or more kinds thereof. The composition of the present invention preferably further includes a luminescent material, preferably a phosphorescent luminescent material and a charge transport material. The composition of the present invention can be suitably used as a composition for forming a light-emitting layer of an organic electroluminescent device.

＜有機溶劑＞本發明的組成物中所含有的有機溶劑是用於利用濕式成膜來形成包含本發明的芳香族化合物的層的、具有揮發性的液體成分。＜Organic solvent＞ The organic solvent contained in the composition of the present invention is a volatile liquid component for forming a layer containing the aromatic compound of the present invention by wet film formation.

該有機溶劑只要是作為溶質的本發明的芳香族化合物及後述的發光材料良好地溶解的有機溶劑，則並無特別限定。The organic solvent is not particularly limited as long as it is an organic solvent in which the aromatic compound of the present invention as a solute and the light-emitting material described later are well dissolved.

作為較佳的有機溶劑，例如可列舉：正癸烷、環己烷、乙基環己烷、十氫萘、雙環己烷等烷烴類；甲苯、二甲苯、均三甲苯、苯基環己烷、四氫萘、甲基萘等芳香族烴類；氯苯、二氯苯、三氯苯等鹵化芳香族烴類；1,2-二甲氧基苯、1,3-二甲氧基苯、苯甲醚、苯***、2-甲氧基甲苯、3-甲氧基甲苯、4-甲氧基甲苯、2,3-二甲基苯甲醚、2,4-二甲基苯甲醚、二苯醚等芳香族醚類；乙酸苯酯、丙酸苯酯、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸正丁酯等芳香族酯類；環己酮、環辛酮、葑酮（fenchone）等脂環族酮類；環己醇、環辛醇等脂環族醇類；甲基乙基酮、二丁基酮等脂肪族酮類；丁醇、己醇等脂肪族醇類；乙二醇二甲醚、乙二醇二***、丙二醇-1-單甲醚乙酸酯（propylene glycol-1-monomethyl ether acetate，PGMEA）等脂肪族醚類等。As preferred organic solvents, for example, alkanes such as n-decane, cyclohexane, ethylcyclohexane, decahydronaphthalene, bicyclohexane; toluene, xylene, mesitylene, phenylcyclohexane , tetrahydronaphthalene, methylnaphthalene and other aromatic hydrocarbons; chlorobenzene, dichlorobenzene, trichlorobenzene and other halogenated aromatic hydrocarbons; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene , anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole , diphenyl ether and other aromatic ethers; phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, n-butyl benzoate and other aromatic esters; cyclohexanone, cyclic Alicyclic ketones such as octanone and fenchone; Alicyclic alcohols such as cyclohexanol and cyclooctanol; Aliphatic ketones such as methyl ethyl ketone and dibutyl ketone; Butanol and hexanol Aliphatic alcohols such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA) and other aliphatic ethers, etc.

該些中，就黏度與沸點的觀點而言，較佳為烷烴類、芳香族烴類、芳香族醚類、芳香族酯類，進而佳為芳香族烴類、芳香族醚類及芳香族酯類，特佳為芳香族烴類及芳香族酯類。Among them, from the viewpoint of viscosity and boiling point, preferred are alkanes, aromatic hydrocarbons, aromatic ethers, and aromatic esters, and more preferred are aromatic hydrocarbons, aromatic ethers, and aromatic esters. Classes, particularly preferably aromatic hydrocarbons and aromatic esters.

該些有機溶劑可單獨使用一種，另外亦可以任意的組合、及比率使用兩種以上。One of these organic solvents may be used alone, or two or more of them may be used in any combination and ratio.

所使用的有機溶劑的沸點通常為80℃以上，較佳為100℃以上，更佳為120℃以上，通常為380℃以下，較佳為350℃以下，更佳為330℃以下。若有機溶劑的沸點低於該範圍，則於濕式成膜時，由於自組成物中的溶劑蒸發，存在成膜穩定性降低的可能性。若有機溶劑的沸點超過該範圍，則於濕式成膜時，由於成膜後的溶劑殘留，存在成膜穩定性降低的可能性。The boiling point of the organic solvent used is usually above 80°C, preferably above 100°C, more preferably above 120°C, usually below 380°C, preferably below 350°C, more preferably below 330°C. If the boiling point of the organic solvent is lower than this range, the film formation stability may decrease due to evaporation of the solvent from the composition during wet film formation. If the boiling point of the organic solvent exceeds this range, the film formation stability may decrease due to the solvent remaining after film formation during wet film formation.

特別是藉由與兩種以上的所述有機溶劑中的沸點為150℃以上的有機溶劑組合，可製作均勻的塗佈膜。認為若沸點150℃以上的有機溶劑為一個以下，則於塗佈時有時無法形成均勻的膜。In particular, a uniform coating film can be produced by combining two or more organic solvents having a boiling point of 150° C. or higher. When there is one or less organic solvents having a boiling point of 150° C. or higher, a uniform film may not be formed at the time of coating.

＜發光材料＞本發明的組成物較佳為發光層形成用組成物。於該情況下，較佳為更含有發光材料。所謂發光材料，是指於本發明的組成物中主要發光的成分，相當於有機電場發光器件中的摻雜劑成分。＜Luminescent material＞ The composition of the present invention is preferably a composition for forming a light-emitting layer. In this case, it is preferable to further contain a light-emitting material. The so-called luminescent material refers to the component that mainly emits light in the composition of the present invention, which is equivalent to the dopant component in the organic electroluminescence device.

作為發光材料，能夠適用公知材料，可將螢光發光材料或磷光發光材料單獨使用或混合多種來使用。就內部量子效率的觀點而言，較佳為磷光發光材料。As the luminescent material, known materials can be used, and a fluorescent luminescent material or a phosphorescent luminescent material can be used alone or in combination. From the viewpoint of internal quantum efficiency, a phosphorescent material is preferable.

（磷光發光材料）所謂磷光發光材料是指自激發三重態狀態顯示出發光的材料。例如，具有Ir、Pt、Eu等的金屬錯合物化合物為其代表例，作為材料的結構，較佳為包含金屬錯合物者。 (phosphorescent luminescent material) The term "phosphorescent material" refers to a material that exhibits light emission from an excited triplet state. For example, a metal complex compound having Ir, Pt, Eu, etc. is a representative example, and the structure of the material preferably includes a metal complex compound.

於金屬錯合物中，作為經由三重態狀態而發光的磷光發光性有機金屬錯合物，可列舉包含選自長週期型週期表（以下，只要無特別限制，則於提及「週期表」的情況下，是指長週期型週期表）第7族～第11族中的金屬作為中心金屬的維爾納（Werner）型錯合物或有機金屬錯合物化合物。作為此種磷光發光材料，較佳為下述式（201）所表示的化合物、或後述的式（205）所表示的化合物，更佳為下述式（201）所表示的化合物。Among the metal complexes, phosphorescent organometallic complexes that emit light through a triplet state include those selected from the long-period periodic table (hereinafter, unless otherwise specified, when referring to the "periodic table") In the case of , it refers to a Werner type complex or an organometallic complex compound in which a metal in Groups 7 to 11 of the long-period periodic table is used as the central metal. Such a phosphorescent material is preferably a compound represented by the following formula (201) or a compound represented by the below-mentioned formula (205), more preferably a compound represented by the following formula (201).

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於所述式（201）中，M是選自週期表第7族～第11族中的金屬，例如可列舉：釕、銠、鈀、銀、錸、鋨、銥、鉑、金、銪。In the formula (201), M is a metal selected from Groups 7 to 11 of the periodic table, for example, ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, gold, and europium.

環A1表示可具有取代基的芳香族烴環結構或可具有取代基的芳香族雜環結構。環A2表示可具有取代基的芳香族雜環結構。 Ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent. Ring A2 represents an aromatic heterocyclic structure which may have a substituent.

R ²⁰¹、R ²⁰²各自獨立地為所述式（202）所表示的結構，「*」表示與環A1或環A2的鍵結位置。R ²⁰¹、R ²⁰²可相同亦可不同。於R ²⁰¹、R ²⁰²分別存在多個的情況下，該些可相同亦可不同。 R ²⁰¹ and R ²⁰² are each independently a structure represented by the formula (202), and "*" represents a bonding position with ring A1 or ring A2. R ²⁰¹ and R ²⁰² may be the same or different. When a plurality of R ²⁰¹ and R ²⁰² exist, these may be the same or different.

式（202）中，Ar ²⁰¹、Ar ²⁰³各自獨立地表示可具有取代基的芳香族烴環結構、或可具有取代基的芳香族雜環結構。 Ar ²⁰²表示可具有取代基的芳香族烴環結構、可具有取代基的芳香族雜環結構、或可具有取代基的脂肪族烴結構。與環A1鍵結的取代基彼此、與環A2鍵結的取代基彼此、或與環A1鍵結的取代基和與環A2鍵結的取代基彼此可相互鍵結而形成環。 In formula (202), Ar ²⁰¹ and Ar ²⁰³ each independently represent an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent. Ar ²⁰² represents an optionally substituted aromatic hydrocarbon ring structure, an optionally substituted aromatic heterocyclic structure, or an optionally substituted aliphatic hydrocarbon structure. The substituents bonded to ring A1, the substituents bonded to ring A2, or the substituents bonded to ring A1 and the substituent bonded to ring A2 may bond to each other to form a ring.

B ²⁰¹-L ²⁰⁰-B ²⁰²表示陰離子性的二齒配位體。B ²⁰¹及B ²⁰²分別獨立地表示碳原子、氧原子或氮原子。該些原子可為構成環的原子。L ²⁰⁰表示單鍵、或與B ²⁰¹及B ²⁰²一起構成二齒配位體的原子團。於存在多個B ²⁰¹-L ²⁰⁰-B ²⁰²的情況下，該些可相同亦可不同。 B ²⁰¹ -L ²⁰⁰ -B ²⁰² represent anionic bidentate ligands. B ²⁰¹ and B ²⁰² each independently represent a carbon atom, an oxygen atom or a nitrogen atom. These atoms may be atoms constituting a ring. L ²⁰⁰ represents a single bond, or an atomic group constituting a bidentate ligand together with B ²⁰¹ and B ²⁰² . When there are a plurality of B ²⁰¹ -L ²⁰⁰ -B ²⁰² , these may be the same or different.

於式（201）、式（202）中， i1、i2分別獨立地表示0以上且12以下的整數。 i3為將能夠於Ar ²⁰²進行取代的數設為上限的0以上的整數。 j為將能夠於Ar ²⁰¹進行取代的數設為上限的0以上的整數。 k1、k2分別獨立地為將能夠於環A1、環A2進行取代的數設為上限的0以上的整數。 m為1～3的整數。 In Formula (201) and Formula (202), i1 and i2 each independently represent an integer of 0 or more and 12 or less. i3 is an integer of 0 or more whose upper limit is the number that can be substituted with Ar ²⁰² . j is an integer of 0 or more whose upper limit is the number that can be substituted with Ar ²⁰¹ . k1 and k2 are each independently an integer of 0 or more whose upper limit is the number that can be substituted in ring A1 and ring A2. m is an integer of 1-3.

作為環A1中的芳香族烴環，較佳為碳數6～30的芳香族烴環，具體而言，較佳為苯環、萘環、蒽環、三苯基環、苊萘環、螢蒽環、芴環。The aromatic hydrocarbon ring in ring A1 is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms, specifically, a benzene ring, a naphthalene ring, an anthracene ring, a triphenyl ring, an acenaphthylene ring, a fluorine ring, or a naphthalene ring. Anthracycline, fluorene ring.

作為環A1中的芳香族雜環，較佳為包含氮原子、氧原子、或硫原子中的任一者作為雜原子的碳數3～30的芳香族雜環，進而佳為呋喃環、苯並呋喃環、噻吩環、苯並噻吩環。The aromatic heterocyclic ring in ring A1 is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing any one of a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, further preferably a furan ring, a benzene Furan ring, thiophene ring, benzothiophene ring.

作為環A1，更佳為苯環、萘環、芴環，特佳為苯環或芴環，最佳為苯環。The ring A1 is more preferably a benzene ring, a naphthalene ring, and a fluorene ring, particularly preferably a benzene ring or a fluorene ring, most preferably a benzene ring.

作為環A2中的芳香族雜環，較佳為包含氮原子、氧原子、或硫原子中的任一者作為雜原子的碳數3～30的芳香族雜環，具體而言，可列舉：吡啶環、嘧啶環、吡嗪環、三嗪環、咪唑環、噁唑環、噻唑環、苯並噻唑環、苯並噁唑環、苯並咪唑環、喹啉環、異喹啉環、喹噁啉環、喹唑啉環、萘啶環、啡啶環，更佳為吡啶環、吡嗪環、嘧啶環、咪唑環、苯並噻唑環、苯並噁唑環、喹啉環、異喹啉環、喹噁啉環、喹唑啉環，進而佳為吡啶環、咪唑環、苯並噻唑環、喹啉環、異喹啉環、喹噁啉環、喹唑啉環，最佳為吡啶環、咪唑環、苯並噻唑環、喹啉環、喹噁啉環、喹唑啉環。 The aromatic heterocyclic ring in ring A2 is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing any one of a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, oxazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring , isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, phenanthridine ring, More preferably pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, benzothiazole ring, benzoxazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, Further preferred are pyridine ring, imidazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, Most preferred are pyridine ring, imidazole ring, benzothiazole ring, quinoline ring, quinoxaline ring, and quinazoline ring.

作為環A1與環A2的較佳的組合，若以（環A1-環A2）表述，則為（苯環-吡啶環）、（苯環-喹啉環）、（苯環-喹噁啉環）、（苯環-喹唑啉環）、（苯環-咪唑環）、（苯環-苯並噻唑環）。As a preferred combination of ring A1 and ring A2, if expressed as (ring A1-ring A2), it is (benzene ring-pyridine ring), (benzene ring-quinoline ring), (benzene ring-quinoxaline ring ), (benzene ring-quinazoline ring), (benzene ring-imidazole ring), (benzene ring-benzothiazole ring).

環A1、環A2可具有的取代基可任意地選擇，較佳為選自後述的取代基群組S中的一種或多種取代基。The substituents that ring A1 and ring A2 may have can be arbitrarily selected, and are preferably one or more substituents selected from substituent group S described later.

於Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³的任一者為可具有取代基的芳香族烴環結構的情況下，作為芳香族烴環結構，較佳為碳數6～30的芳香族烴環，具體而言，較佳為苯環、萘環、蒽環、三苯基環、苊萘環、螢蒽環、芴環，更佳為苯環、萘環、芴環，最佳為苯環。 When any one of Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ is an aromatic hydrocarbon ring structure which may have a substituent, the aromatic hydrocarbon ring structure is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms, specifically For benzene ring, naphthalene ring, anthracene ring, triphenyl ring, acenaphthylene ring, fluoranthene ring, and fluorene ring are preferred, benzene ring, naphthalene ring, and fluorene ring are more preferred, and benzene ring is most preferred.

於Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³的任一者為可具有取代基的芴環的情況下，芴環的9位及9'位較佳為具有取代基或與鄰接的結構鍵結。 When any one of Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ is a fluorene ring which may have a substituent, the 9-position and 9'-position of the fluorene ring preferably have a substituent or bond to an adjacent structure.

於Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³的任一者為可具有取代基的苯環的情況下，較佳為至少一個苯環於鄰位或間位與鄰接的結構鍵結，更佳為至少一個苯環於間位與鄰接的結構鍵結。 When any one of Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ is a benzene ring that may have a substituent, it is preferable that at least one benzene ring is bonded to the adjacent structure at the ortho or meta position, more preferably at least one The benzene ring is bonded to the adjacent structure at the meta position.

於Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³的任一者為可具有取代基的芳香族雜環結構的情況下，作為芳香族雜環結構，較佳為包含氮原子、氧原子、或硫原子中的任一者作為雜原子的碳數3～30的芳香族雜環，具體而言，可列舉：吡啶環、嘧啶環、吡嗪環、三嗪環、咪唑環、噁唑環、噻唑環、苯並噻唑環、苯並噁唑環、苯並咪唑環、喹啉環、異喹啉環、喹噁啉環、喹唑啉環、萘啶環、啡啶環、咔唑環、二苯並呋喃環、二苯並噻吩環，較佳為吡啶環、嘧啶環、三嗪環、咔唑環、二苯並呋喃環、二苯並噻吩環。 When any one of Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ is an aromatic heterocyclic structure that may have a substituent, the aromatic heterocyclic structure preferably includes a nitrogen atom, an oxygen atom, or a sulfur atom. Aromatic heterocyclic rings having 3 to 30 carbon atoms as heteroatoms, specifically, pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, imidazole rings, oxazole rings, thiazole rings, benzene Thiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, phenanthridine ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, preferably pyridine ring, pyrimidine ring, triazine ring, carbazole ring, dibenzofuran ring, and dibenzothiophene ring.

於Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³的任一者為可具有取代基的咔唑環的情況下，咔唑環的N位較佳為具有取代基或與鄰接的結構鍵結。 When any of Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ is a carbazole ring which may have a substituent, the N-position of the carbazole ring preferably has a substituent or is bonded to an adjacent structure.

於Ar ²⁰²為可具有取代基的脂肪族烴結構的情況下，作為脂肪族烴結構，為具有直鏈、分支鏈、或環狀結構的脂肪族烴結構，較佳為碳數為1以上且24以下的脂肪族烴，更佳為碳數為1以上且12以下的脂肪族烴，進而佳為碳數為1以上且8以下的脂肪族烴。 When Ar ²⁰² is an aliphatic hydrocarbon structure that may have a substituent, the aliphatic hydrocarbon structure is an aliphatic hydrocarbon structure having a straight chain, branched chain, or cyclic structure, preferably having 1 or more carbon atoms and The aliphatic hydrocarbon having 24 or less is more preferably an aliphatic hydrocarbon having 1 or more and 12 or less carbon atoms, and still more preferably an aliphatic hydrocarbon having 1 or more and 8 or less carbon atoms.

i1、i2分別獨立地為0～12的整數，較佳為1～12的整數，更佳為1～8的整數，進而佳為1～6的整數。藉由為該範圍，可預見溶解性提高、電荷傳輸性提高。i1 and i2 are each independently an integer of 0-12, preferably an integer of 1-12, more preferably an integer of 1-8, further preferably an integer of 1-6. By setting it as this range, improvement of solubility and improvement of charge transportability are expected.

i3較佳為0～5的整數，更佳為0～2的整數，進而佳為0或1。i3 is preferably an integer of 0-5, more preferably an integer of 0-2, still more preferably 0 or 1.

j較佳為表示0～2的整數，更佳為0或1。j is preferably an integer representing 0-2, more preferably 0 or 1.

k1、k2分別獨立地較佳為0～3的整數，更佳為1～3的整數，進而佳為1或2，特佳為1。k1 and k2 are each independently preferably an integer of 0-3, more preferably an integer of 1-3, still more preferably 1 or 2, particularly preferably 1.

Ar ²⁰¹、Ar ²⁰²、Ar ²⁰³可具有的取代基可任意地選擇，但較佳為選自後述的取代基群組S中的一種或多種取代基，更佳為氫原子、烷基、芳基，特佳為氫原子、烷基，最佳為未經取代（氫原子）。 Ar ²⁰¹ , Ar ²⁰² , and Ar ²⁰³ may have substituents that can be selected arbitrarily, but are preferably one or more substituents selected from the substituent group S described later, more preferably hydrogen atoms, alkyl groups, and aryl groups , particularly preferably a hydrogen atom, an alkyl group, most preferably unsubstituted (hydrogen atom).

於無特別說明的情況下，作為取代基，較佳為選自以下的取代基群組S中的基。Unless otherwise specified, the substituent is preferably a group selected from the substituent group S below.

＜取代基群組S＞ ·烷基，較佳為碳數1～20的烷基，更佳為碳數1～12的烷基，進而佳為碳數1～8的烷基，特佳為碳數1～6的烷基。 ·烷氧基，較佳為碳數1～20的烷氧基，更佳為碳數1～12的烷氧基，進而佳為碳數1～6的烷氧基。 ·芳氧基，較佳為碳數6～20的芳氧基，更佳為碳數6～14的芳氧基，進而佳為碳數6～12的芳氧基，特佳為碳數6的芳氧基。 ·雜芳氧基，較佳為碳數3～20的雜芳氧基，更佳為碳數3～12的雜芳氧基。 ·烷基胺基，較佳為碳數1～20的烷基胺基，更佳為碳數1～12的烷基胺基。 ·芳基胺基，較佳為碳數6～36的芳基胺基，更佳為碳數6～24的芳基胺基。 ·芳烷基，較佳為碳數7～40的芳烷基，更佳為碳數7～18的芳烷基，進而佳為碳數7～12的芳烷基。 ·雜芳烷基，較佳為碳數7～40的雜芳烷基，更佳為碳數7～18的雜芳烷基。 ·烯基，較佳為碳數2～20的烯基，更佳為碳數2～12的烯基，進而佳為碳數2～8的烯基，特佳為碳數2～6的烯基。 ·炔基，較佳為碳數2～20的炔基，更佳為碳數2～12的炔基。 ·芳基，較佳為碳數6～30的芳基，更佳為碳數6～24的芳基，進而佳為碳數6～18的芳基，特佳為碳數6～14的芳基。 ·雜芳基，較佳為碳數3～30的雜芳基，更佳為碳數3～24的雜芳基，進而佳為碳數3～18的雜芳基，特佳為碳數3～14的雜芳基。 ·烷基矽烷基，較佳為烷基的碳數為1～20的烷基矽烷基，更佳為烷基的碳數為1～12的烷基矽烷基。 ·芳基矽烷基，較佳為芳基的碳數為6～20的芳基矽烷基，更佳為芳基的碳數為6～14的芳基矽烷基。 ·烷基羰基，較佳為碳數2～20的烷基羰基。 ·芳基羰基，較佳為碳數7～20的芳基羰基。以上的基中一個以上的氫原子經氟原子取代，或者一個以上的氫原子亦可經氘原子取代。 ·氫原子、氘原子、氟原子、氰基、或-SF ₅。 <Substituent Group S> An alkyl group, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 8 carbon atoms, particularly preferably An alkyl group with 1 to 6 carbon atoms. - An alkoxy group is preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 12 carbon atoms, and still more preferably an alkoxy group having 1 to 6 carbon atoms. Aryloxy group, preferably an aryloxy group with 6 to 20 carbon atoms, more preferably an aryloxy group with 6 to 14 carbon atoms, further preferably an aryloxy group with 6 to 12 carbon atoms, particularly preferably 6 carbon atoms of aryloxy groups. · Heteroaryloxy group, preferably a heteroaryloxy group having 3 to 20 carbon atoms, more preferably a heteroaryloxy group having 3 to 12 carbon atoms. · An alkylamine group, preferably an alkylamine group having 1 to 20 carbon atoms, more preferably an alkylamine group having 1 to 12 carbon atoms. · An arylamine group, preferably an arylamine group having 6 to 36 carbon atoms, more preferably an arylamine group having 6 to 24 carbon atoms. · Aralkyl, preferably an aralkyl group having 7 to 40 carbons, more preferably an aralkyl group having 7 to 18 carbons, still more preferably an aralkyl group having 7 to 12 carbons. ·Heteroaralkyl group, preferably a heteroaralkyl group having 7 to 40 carbon atoms, more preferably a heteroaralkyl group having 7 to 18 carbon atoms. Alkenyl, preferably alkenyl having 2 to 20 carbons, more preferably alkenyl having 2 to 12 carbons, still more preferably alkenyl having 2 to 8 carbons, particularly preferably alkenyl having 2 to 6 carbons base. - An alkynyl group, preferably an alkynyl group having 2 to 20 carbon atoms, more preferably an alkynyl group having 2 to 12 carbon atoms. Aryl, preferably aryl with 6 to 30 carbons, more preferably aryl with 6 to 24 carbons, further preferably aryl with 6 to 18 carbons, particularly preferably aryl with 6 to 14 carbons base. Heteroaryl, preferably a heteroaryl group with 3 to 30 carbons, more preferably a heteroaryl group with 3 to 24 carbons, further preferably a heteroaryl group with 3 to 18 carbons, especially preferably 3 carbons ~14 heteroaryl. · An alkylsilyl group, preferably an alkylsilyl group having 1 to 20 carbon atoms in the alkyl group, more preferably an alkylsilyl group having 1 to 12 carbon atoms in the alkyl group. - An arylsilyl group, preferably an arylsilyl group having 6 to 20 carbon atoms in the aryl group, more preferably an arylsilyl group having 6 to 14 carbon atoms in the aryl group. Alkylcarbonyl, preferably an alkylcarbonyl having 2 to 20 carbons. - An arylcarbonyl group, preferably an arylcarbonyl group having 7 to 20 carbon atoms. In the above groups, one or more hydrogen atoms may be substituted by fluorine atoms, or one or more hydrogen atoms may be substituted by deuterium atoms. A hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, or -SF ₅ .

只要無特別說明，則芳基是芳香族烴，雜芳基是芳香族雜環。Unless otherwise specified, an aryl group is an aromatic hydrocarbon, and a heteroaryl group is an aromatic heterocyclic ring.

（取代基群組S中的較佳的基）於該些取代基群組S中，較佳為烷基、烷氧基、芳氧基、芳基胺基、芳烷基、烯基、芳基、雜芳基、烷基矽烷基、芳基矽烷基、該些基的一個以上的氫原子經氟原子取代的基、氟原子、氰基、或-SF ₅，更佳為烷基、芳基胺基、芳烷基、烯基、芳基、雜芳基、該些基的一個以上的氫原子經氟原子取代的基、氟原子、氰基、或-SF ₅，進而佳為烷基、烷氧基、芳氧基、芳基胺基、芳烷基、烯基、芳基、雜芳基、烷基矽烷基、芳基矽烷基，特佳為烷基、芳基胺基、芳烷基、烯基、芳基、雜芳基，最佳為烷基、芳基胺基、芳烷基、芳基、雜芳基。 (Preferable group in substituent group S) In these substituent group S, preferably alkyl, alkoxy, aryloxy, arylamino, aralkyl, alkenyl, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, group in which one or more hydrogen atoms of these groups are replaced by fluorine atom, fluorine atom, cyano group, or -SF ₅ , more preferably alkyl, aryl Amino group, aralkyl group, alkenyl group, aryl group, heteroaryl group, group in which one or more hydrogen atoms of these groups are substituted by fluorine atom, fluorine atom, cyano group, or -SF ₅ , further preferably alkyl group , alkoxy, aryloxy, arylamino, aralkyl, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, particularly preferably alkyl, arylamino, aryl Alkyl, alkenyl, aryl, heteroaryl, most preferably alkyl, arylamino, aralkyl, aryl, heteroaryl.

該些取代基群組S亦可更具有選自取代基群組S中的取代基作為取代基。可具有的取代基的較佳的基、更佳的基、進而佳的基、特佳的基、最佳的基與取代基群組S中的較佳的基等相同。The substituent groups S may further have a substituent selected from the substituent group S as a substituent. A preferable group, a more preferable group, a further preferable group, a particularly preferable group, and the most preferable group of the optional substituent are the same as the preferable group in the substituent group S, and the like.

（式（201）的較佳的結構）所述式（201）中的所述式（202）所表示的結構中，較佳為（i）具有連結有苯環的基的結構、（ii）具有在環A1或環A2上鍵結有烷基或芳烷基的芳香族烴基或芳香族雜環基的結構、（iii）於環A1或環A2上鍵結有樹突的結構。 (better structure of formula (201)) Among the structures represented by the formula (202) in the formula (201), it is preferable that (i) have a structure having a group connected to a benzene ring, (ii) have a structure having a group bonded to the ring A1 or ring A2 A structure of an alkyl or aralkyl aromatic hydrocarbon group or an aromatic heterocyclic group, (iii) a structure in which a dendron is bonded to ring A1 or ring A2.

（i）具有連結有苯環的基的結構中，Ar ²⁰¹為苯環結構，i1為1～6，至少一個所述苯環於鄰位或間位與鄰接的結構鍵結。藉由為該結構，可期待提高溶解性，且提高電荷傳輸性。 (i) In the structure having a group connected to a benzene ring, Ar ²⁰¹ is a benzene ring structure, i1 is 1 to 6, and at least one of the benzene rings is bonded to the adjacent structure at the ortho or meta position. By having this structure, it is expected that the solubility will be improved and the charge transport property will be improved.

（ii）具有在環A1或環A2上鍵結有烷基或芳烷基的芳香族烴基或芳香族雜環基的結構中，Ar ²⁰¹為芳香族烴結構或芳香族雜環結構，i1為1～6，Ar ²⁰²為脂肪族烴結構，i2為1～12，較佳為3～8，Ar ²⁰³為苯環結構，i3為0或1。於該結構的情況下，較佳為Ar ²⁰¹為所述芳香族烴結構，進而佳為連結有一個～五個苯環的結構，更佳為一個苯環。藉由為該結構，可期待提高溶解性，且提高電荷傳輸性。 (ii) In the structure having an aromatic hydrocarbon group or an aromatic heterocyclic group with an alkyl or aralkyl group bonded to ring A1 or ring A2, Ar ²⁰¹ is an aromatic hydrocarbon structure or an aromatic heterocyclic structure, and i1 is 1-6, Ar ²⁰² is an aliphatic hydrocarbon structure, i2 is 1-12, preferably 3-8, Ar ²⁰³ is a benzene ring structure, i3 is 0 or 1. In the case of this structure, Ar ²⁰¹ is preferably the above-mentioned aromatic hydrocarbon structure, more preferably a structure in which one to five benzene rings are connected, more preferably one benzene ring. By having this structure, it is expected that the solubility will be improved and the charge transport property will be improved.

（iii）於環A1或環A2上鍵結有樹突的結構中，Ar ²⁰¹、Ar ²⁰²為苯環結構，Ar ²⁰³為聯苯或三聯苯結構，i1、i2為1～6，i3為2，j為2。藉由為該結構，可期待提高溶解性，且提高電荷傳輸性。 (iii) In the structure with dendrites bonded to ring A1 or ring A2, Ar ²⁰¹ and Ar ²⁰² are benzene ring structures, Ar ²⁰³ is biphenyl or terphenyl structure, i1 and i2 are 1 to 6, and i3 is 2 , j is 2. By having this structure, it is expected that the solubility will be improved and the charge transport property will be improved.

於所述式（201）中，於B ²⁰¹-L ²⁰⁰-B ²⁰²所表示的結構中，較佳為下述式（203）或式（204）所表示的結構。 In the formula (201), among the structures represented by B ²⁰¹ -L ²⁰⁰ -B ²⁰² , the structure represented by the following formula (203) or formula (204) is preferable.

[化39]

[chem 39]

所述式（203）中，R ²¹¹、R ²¹²、R ²¹³表示取代基。該取代基並無特別限定，但較佳為選自所述取代基群組S中的基。 In the formula (203), R ²¹¹ , R ²¹² , and R ²¹³ represent substituents. The substituent is not particularly limited, but is preferably a group selected from the group S of substituents.

[化40]

[chemical 40]

所述式（204）中，環B3表示可具有取代基的包含氮原子的芳香族雜環結構。環B3較佳為吡啶環。環B3可具有的取代基並無特別限定，較佳為選自所述取代基群組S中的基。 In the formula (204), the ring B3 represents an aromatic heterocyclic structure containing a nitrogen atom which may have a substituent. Ring B3 is preferably a pyridine ring. The substituent that ring B3 may have is not particularly limited, and is preferably a group selected from the substituent group S described above.

作為所述式（201）所表示的磷光發光材料，並無特別限定，具體而言可列舉以下的結構。以下中，Me是指甲基，Ph是指苯基。 The phosphorescent light-emitting material represented by the formula (201) is not particularly limited, but specifically, the following structures are exemplified. Hereinafter, Me means a methyl group, and Ph means a phenyl group.

[化41]

[chem 41]

[化42]

[chem 42]

[化43]

[chem 43]

[化44]

[chem 44]

接下來，對下述式（205）所表示的化合物進行說明。Next, a compound represented by the following formula (205) will be described.

[化45]

[chem 45]

式（205）中，M ²表示金屬。T表示碳原子或氮原子。R ⁹²～R ⁹⁵分別獨立地表示取代基。其中，於T為氮原子的情況下，不存在R ⁹⁴及R ⁹⁵。 In formula (205), M ² represents a metal. T represents a carbon atom or a nitrogen atom. R ⁹² to R ⁹⁵ each independently represent a substituent. However, when T is a nitrogen atom, R ⁹⁴ and R ⁹⁵ do not exist.

式（205）中，M ²表示金屬。作為具體例，可列舉選自週期表第7族～第11族中的金屬。其中，較佳為可列舉釕、銠、鈀、銀、錸、鋨、銥、鉑或金，特佳為可列舉鉑、鈀等二價金屬。 In formula (205), M ² represents a metal. Specific examples include metals selected from Groups 7 to 11 of the periodic table. Among them, ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, or gold are preferable, and divalent metals such as platinum and palladium are particularly preferable.

式（205）中，R ⁹²及R ⁹³分別獨立地表示氫原子、鹵素原子、烷基、芳烷基、烯基、氰基、胺基、醯基、烷氧基羰基、羧基、烷氧基、烷基胺基、芳烷基胺基、鹵代烷基、羥基、芳氧基、芳香族烴基或芳香族雜環基。 In formula (205), R ⁹² and R ⁹³ independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, a cyano group, an amino group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxy group , alkylamino group, aralkylamino group, haloalkyl group, hydroxyl group, aryloxy group, aromatic hydrocarbon group or aromatic heterocyclic group.

進而，於T為碳原子的情況下，R ⁹⁴及R ⁹⁵分別獨立地表示與R ⁹²及R ⁹³相同的例示物所表示的取代基。於T為氮原子的情況下，不存在與該T直接鍵結的R ⁹⁴或R ⁹⁵。 Furthermore, when T is a carbon atom, R ⁹⁴ and R ⁹⁵ each independently represent a substituent represented by the same example as R ⁹² and R ⁹³ . When T is a nitrogen atom, there is no R ⁹⁴ or R ⁹⁵ directly bonded to T.

R ⁹²～R ⁹⁵亦可更具有取代基。作為該取代基，可設為作為R ⁹²及R ⁹³而列舉的所述取代基。進而，R ⁹²～R ⁹⁵中任意的兩個以上的基可相互連結而形成環。 R ⁹² to R ⁹⁵ may further have substituents. As this substituent, the substituents mentioned above as ^R92 and ^R93 can be used. Furthermore, arbitrary two or more groups among R ⁹² to R ⁹⁵ may be linked to each other to form a ring.

（分子量）磷光發光材料的分子量較佳為5000以下，進而佳為4000以下，特佳為3000以下。磷光發光材料的分子量通常為1000以上，較佳為1100以上，進而佳為1200以上。認為藉由為該分子量範圍，磷光發光材料彼此不會凝聚而與本發明的化合物及/或其他電荷傳輸材料均勻地混合，可獲得發光效率高的發光層。 (molecular weight) The molecular weight of the phosphorescent material is preferably at most 5,000, more preferably at most 4,000, and most preferably at most 3,000. The molecular weight of the phosphorescent material is generally 1000 or more, preferably 1100 or more, and more preferably 1200 or more. It is considered that by using this molecular weight range, the phosphorescent materials are uniformly mixed with the compound of the present invention and/or other charge transport materials without agglomerating each other, and a light emitting layer with high luminous efficiency can be obtained.

就Tg或熔點、分解溫度等高、磷光發光材料及所形成的發光層的耐熱性優異的方面、以及不易發生由氣體產生、再結晶化及分子的遷移等引起的膜質的降低或者伴隨材料的熱分解而來的雜質濃度的上升等方面而言，磷光發光材料的分子量較佳為大。就容易進行有機化合物的精製的方面而言，磷光發光材料的分子量較佳為小。In terms of high Tg, melting point, decomposition temperature, etc., excellent heat resistance of the phosphorescent luminescent material and the formed luminescent layer, and the reduction of film quality caused by gas generation, recrystallization, and molecular migration, etc. The molecular weight of the phosphorescent light-emitting material is preferably large in view of an increase in impurity concentration due to thermal decomposition. The molecular weight of the phosphorescent light-emitting material is preferably small in terms of ease of purification of the organic compound.

＜電荷傳輸材料＞於本發明的組成物為發光層形成用組成物的情況下，較佳為除了含有本發明的芳香族化合物以外，更含有電荷傳輸材料作為進一步的主體材料。＜Charge transport materials＞ When the composition of the present invention is a composition for forming a light-emitting layer, it is preferable to further contain a charge transport material as a further host material in addition to the aromatic compound of the present invention.

用作發光層的主體材料的電荷傳輸材料是具有電荷傳輸性優異的骨架的材料，較佳為自電子傳輸性材料、電洞傳輸性材料及能夠傳輸電子與電洞兩者的兩極性材料中選擇。The charge-transporting material used as the host material of the light-emitting layer is a material having a skeleton excellent in charge-transporting properties, and is preferably selected from among electron-transporting materials, hole-transporting materials, and bipolar materials capable of transporting both electrons and holes. choose.

作為電荷傳輸性優異的骨架，具體而言，可列舉：芳香族結構、芳香族胺結構、三芳基胺結構、二苯並呋喃結構、萘結構、菲結構、酞菁結構、卟啉結構、噻吩結構、苄基苯基結構、芴結構、喹吖啶酮結構、三伸苯結構、咔唑結構、芘結構、蒽結構、啡啉結構、喹啉結構、吡啶結構、嘧啶結構、三嗪結構、噁二唑結構或咪唑結構等。Specific examples of the skeleton having excellent charge transport properties include aromatic structures, aromatic amine structures, triarylamine structures, dibenzofuran structures, naphthalene structures, phenanthrene structures, phthalocyanine structures, porphyrin structures, and thiophene structures. Structure, benzylphenyl structure, fluorene structure, quinacridone structure, triphenylene structure, carbazole structure, pyrene structure, anthracene structure, morpholine structure, quinoline structure, pyridine structure, pyrimidine structure, triazine structure, Oxadiazole structure or imidazole structure, etc.

作為電子傳輸性材料，更佳為電子傳輸性優異且結構比較穩定的具有吡啶結構、嘧啶結構、及/或三嗪結構的化合物，進而佳為具有嘧啶結構、及/或三嗪結構的化合物。特佳為後述的式（250）所表示的化合物。The electron transport material is more preferably a compound having a pyridine structure, a pyrimidine structure, and/or a triazine structure, which is excellent in electron transport property and has a relatively stable structure, and is further preferably a compound having a pyrimidine structure and/or a triazine structure. Particularly preferred is a compound represented by the formula (250) described below.

電洞傳輸性材料為具有電洞傳輸性優異的結構的化合物，於所述電荷傳輸性優異的骨架中，作為電洞傳輸性優異的結構，較佳為咔唑結構、二苯並呋喃結構、三芳基胺結構、萘結構、菲結構或芘結構，進而佳為咔唑結構、二苯並呋喃結構或三芳基胺結構。特佳為後述的式（240）所表示的化合物。The hole-transporting material is a compound having a structure excellent in hole-transporting properties, and in the skeleton having excellent charge-transporting properties, the structure having excellent hole-transporting properties is preferably a carbazole structure, a dibenzofuran structure, A triarylamine structure, a naphthalene structure, a phenanthrene structure or a pyrene structure, and more preferably a carbazole structure, a dibenzofuran structure or a triarylamine structure. Particularly preferred is a compound represented by the formula (240) described below.

於本發明的組成物為發光層形成用組成物的情況下，較佳為除了含有本發明的芳香族化合物以外，更含有後述的式（250）所表示的化合物、及/或後述的式（240）所表示的化合物作為進一步的主體材料。就發光層內的電荷平衡調整的觀點及發光效率的觀點而言，較佳為包含此種材料作為進一步的主體材料。When the composition of the present invention is a composition for forming a light-emitting layer, it is preferable to contain, in addition to the aromatic compound of the present invention, a compound represented by the formula (250) described later, and/or the formula ( 240) as a further host material. From the viewpoint of charge balance adjustment in the light-emitting layer and the viewpoint of luminous efficiency, it is preferable to include such a material as a further host material.

用作發光層的主體材料的電荷傳輸材料較佳為具有三環以上的縮合環結構的化合物，進而佳為具有兩個以上的三環以上的縮合環結構的化合物或具有至少一個五環以上的縮合環的化合物。藉由為該些化合物，而容易獲得如下效果：分子的剛直性增加，並抑制響應熱的分子運動的程度。進而，就電荷傳輸性及材料的耐久性的方面而言，較佳為三環以上的縮合環及五環以上的縮合環具有芳香族烴環或芳香族雜環。The charge transport material used as the host material of the light-emitting layer is preferably a compound having a condensed ring structure of three or more rings, more preferably a compound having two or more condensed ring structures of three or more rings or a compound having at least one five or more rings. Compounds with condensed rings. By using these compounds, the effects of increasing the rigidity of molecules and suppressing the degree of molecular motion in response to heat are easily obtained. Furthermore, it is preferable that the condensed ring having three or more rings and the condensed ring having five or more rings have an aromatic hydrocarbon ring or an aromatic heterocycle in terms of charge transport properties and durability of the material.

作為三環以上的縮合環結構，具體而言，可列舉：蒽結構、菲結構、芘結構、䓛結構、稠四苯結構、三伸苯結構、芴結構、苯並芴結構、茚並芴結構、吲哚並芴結構、咔唑結構、茚並咔唑結構、吲哚並咔唑結構、二苯並呋喃結構、二苯並噻吩結構等。Concrete examples of the condensed ring structure having three or more rings include: anthracene structure, phenanthrene structure, pyrene structure, pyrene structure, fused tetraphenyl structure, triphenylene structure, fluorene structure, benzofluorene structure, and indenofluorene structure , indolofluorene structure, carbazole structure, indenocarbazole structure, indolocarbazole structure, dibenzofuran structure, dibenzothiophene structure, etc.

就電荷傳輸性以及溶解性的觀點而言，較佳為選自由菲結構、芴結構、茚並芴結構、咔唑結構、茚並咔唑結構、吲哚並咔唑結構、二苯並呋喃結構及二苯並噻吩結構所組成的群組中的至少一種。就相對於電荷而言的耐久性的觀點而言，進而佳為咔唑結構或吲哚並咔唑結構。From the viewpoint of charge transportability and solubility, it is preferably selected from the group consisting of phenanthrene structure, fluorene structure, indenofluorene structure, carbazole structure, indenocarbazole structure, indolocarbazole structure, and dibenzofuran structure. and at least one of the group consisting of dibenzothiophene structures. From the viewpoint of durability against charge, a carbazole structure or an indolocarbazole structure is more preferable.

就可撓性優異的觀點而言，用作發光層的主體材料的電荷傳輸材料較佳為高分子材料。使用可撓性優異的材料而形成的發光層較佳為作為形成於柔性基板上的有機電場發光元件的發光層。於用作發光層中包含的主體材料的電荷傳輸材料為高分子材料的情況下，分子量較佳為5,000以上且1,000,000以下，更佳為10,000以上且500,000以下，進而佳為10,000以上且100,000以下。From the viewpoint of excellent flexibility, the charge transport material used as the host material of the light emitting layer is preferably a polymer material. A light-emitting layer formed using a material excellent in flexibility is preferable as a light-emitting layer of an organic electroluminescence element formed on a flexible substrate. When the charge transport material used as the host material contained in the light-emitting layer is a polymer material, the molecular weight is preferably from 5,000 to 1,000,000, more preferably from 10,000 to 500,000, still more preferably from 10,000 to 100,000.

就合成及精製的容易性、電子傳輸性能及電洞傳輸性能的設計容易性、溶解於溶媒中時的黏度調整的容易性的觀點而言，用作發光層的主體材料的電荷傳輸材料較佳為低分子。於用作發光層中包含的主體材料的電荷傳輸材料為低分子材料的情況下，分子量較佳為5,000以下，更佳為4,000以下，特佳為3,000以下，最佳為2,000以下，通常為600以上，較佳為800以上。於利用濕式成膜法形成與發光層上相接而形成的層的情況下，低分子電荷傳輸材料的分子量較佳為1000以上，更佳為1100以上，特佳為1200以上。From the viewpoint of ease of synthesis and purification, ease of design of electron transport performance and hole transport performance, and ease of viscosity adjustment when dissolved in a solvent, the charge transport material used as the host material of the light-emitting layer is preferable. for low molecular weight. When the charge transport material used as the host material contained in the light emitting layer is a low molecular weight material, the molecular weight is preferably 5,000 or less, more preferably 4,000 or less, particularly preferably 3,000 or less, most preferably 2,000 or less, usually 600 Above, preferably above 800. When forming a layer in contact with the light-emitting layer by a wet film-forming method, the molecular weight of the low-molecular charge transport material is preferably at least 1000, more preferably at least 1100, and particularly preferably at least 1200.

＜式（250）所表示的化合物＞ [化46]

<Compound represented by formula (250)> [Chem. 46]

式（250）所表示的化合物較佳為電荷傳輸性化合物，即電荷傳輸性主體材料。The compound represented by formula (250) is preferably a charge-transporting compound, that is, a charge-transporting host material.

（W）式（250）中的W表示CH或N，其中至少一個為N。就電子傳輸性及電子耐久性的觀點而言，較佳為W的至少兩個為N，更佳為全部為N。 (W) W in formula (250) represents CH or N, at least one of which is N. From the viewpoint of electron transport properties and electron durability, at least two of W are preferably N, more preferably all of them are N.

＜Xa ¹、Ya ¹、Za ¹、Xa ²、Ya ²、Za ²＞作為於式（250）中的Xa ¹、Ya ¹、Za ¹為可具有取代基的碳數6～30的二價芳香族烴基的情況、及Xa ²、Ya ²、Za ²為可具有取代基的碳數6～30的一價芳香族烴基的情況下的、碳數6～30的芳香族烴基的芳香族烴環，較佳為六員環的單環、或二縮合環～五縮合環。具體而言，可列舉：苯環、萘環、蒽環、菲環、芴環、苝環、稠四苯環、芘環、苯並芘環、䓛環、三伸苯環、螢蒽環、茚並芴環等。其中，較佳為苯環、萘環、蒽環、菲環、或芴環，更佳為苯環、萘環、菲環或芴環，進而佳為苯環、萘環或芴環。 <Xa ¹ , Ya ¹ , Za ¹ , Xa ² , Ya ² , Za ² > Xa ¹ , Ya ¹ , Za ¹ in formula (250) are divalent aromatic compounds having 6 to 30 carbon atoms that may have substituents. In the case of an aromatic hydrocarbon group, and in the case where Xa ² , Ya ² , and Za ² are monovalent aromatic hydrocarbon groups having 6 to 30 carbon atoms which may have substituents, the aromatic hydrocarbon ring of an aromatic hydrocarbon group having 6 to 30 carbon atoms , preferably a six-membered monocyclic ring, or a dicondensed ring to a pentacondensed ring. Specifically, examples include: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, perylene ring, fused tetraphenyl ring, pyrene ring, benzopyrene ring, pyrene ring, triphenylene ring, fluoranthracene ring, Indenofluorene ring etc. Among them, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring is preferable, a benzene ring, a naphthalene ring, a phenanthrene ring, or a fluorene ring is more preferable, and a benzene ring, a naphthalene ring, or a fluorene ring is still more preferable.

作為於式（250）中的Xa ¹、Ya ¹、Za ¹為可具有取代基的碳數3～30的二價芳香族雜環基的情況、及Xa ²、Ya ²、Za ²為可具有取代基的碳數3～30的一價芳香族雜環基的情況下的、碳數3～30的芳香族雜環基的芳香族雜環，較佳為五員環或六員環的單環、或者二縮合環～五縮合環。具體而言，可列舉：呋喃環、苯並呋喃環、二苯並呋喃環、噻吩環、苯並噻吩環、二苯並噻吩環、吡咯環、吡唑環、咪唑環、噁二唑環、吲哚環、咔唑環、吲哚並咔唑環、茚並咔唑環、吡咯並咪唑環、吡咯並吡唑環、吡咯並吡咯環、噻吩並吡咯環、噻吩並噻吩環、呋喃並吡咯環、呋喃並呋喃環、噻吩並呋喃環、苯並異噁唑環、苯並異噻唑環、苯並咪唑環、吡啶環、吡嗪環、噠嗪環、嘧啶環、三嗪環、喹啉環、異喹啉環、噌啉環、喹噁啉環、呸啶環、喹唑啉環、喹唑啉酮環等。其中，較佳為噻吩環、吡咯環、咪唑環、吡啶環、嘧啶環、三嗪環、喹啉環、喹唑啉環、咔唑環、二苯並呋喃環、二苯並噻吩環、吲哚並咔唑環、啡啉環、或茚並咔唑環，更佳為吡啶環、嘧啶環、三嗪環、喹啉環、喹唑啉環、咔唑環、二苯並呋喃環或二苯並噻吩環，進而佳為咔唑環、二苯並呋喃環或二苯並噻吩環。 In the case where Xa ¹ , Ya ¹ , and Za ¹ in the formula (250) are divalent aromatic heterocyclic groups having 3 to 30 carbon atoms that may have substituents, and Xa ² , Ya ² , and Za ² may have In the case of a monovalent aromatic heterocyclic group having 3 to 30 carbon atoms in the substituent, the aromatic heterocyclic ring of an aromatic heterocyclic group having 3 to 30 carbon atoms is preferably a five-membered ring or a six-membered ring ring, or two to five condensed rings. Specifically, a furan ring, a benzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, Indole ring, carbazole ring, indolocarbazole ring, indenocarbazole ring, pyrrolopyrrole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, pyhidine ring, quinazoline ring, quinazolinone ring, etc. Among them, thiophene ring, pyrrole ring, imidazole ring, pyridine ring, pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, ind Indocarbazole ring, phenanthroline ring, or indenocarbazole ring, more preferably pyridine ring, pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran ring or bis The benzothiophene ring is more preferably a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring.

式（250）中的Xa ¹、Ya ¹、Za ¹、Xa ²、Ya ²、及Za ²中，特佳的芳香族烴環為苯環、萘環或菲環。特佳的芳香族雜環為咔唑環、二苯並呋喃環或二苯並噻吩環。 Among Xa ¹ , Ya ¹ , Za ¹ , Xa ² , Ya ² , and Za ² in formula (250), a particularly preferable aromatic hydrocarbon ring is a benzene ring, a naphthalene ring, or a phenanthrene ring. A particularly preferable aromatic heterocycle is a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring.

（g11、h11、j11） g11、h11、及j11各自獨立地表示0～6的整數，g11、h11、j11的至少一個為1以上的整數。就電荷傳輸性及耐久性的觀點而言，較佳為g11為2以上、或者h11及j11中至少一者為3以上。 (g11, h11, j11) g11, h11, and j11 each independently represent an integer of 0 to 6, and at least one of g11, h11, and j11 is an integer of 1 or more. From the viewpoint of charge transportability and durability, g11 is preferably 2 or more, or at least one of h11 and j11 is 3 or more.

就電荷傳輸性、耐久性及於有機溶劑中的溶解性的觀點而言，式（250）所表示的化合物較佳為亦包括中心具有三個W的環在內，合計具有8個～18個該些環。From the viewpoint of charge transportability, durability, and solubility in organic solvents, the compound represented by formula (250) preferably has a total of 8 to 18 W rings including a ring having three W in the center. the rings.

（R ³¹）關於作為取代基時的R ³¹，較佳為可具有取代基的碳數6～30的芳香族烴基或可具有取代基的碳數3～30的芳香族雜環基。就耐久性提高及電荷傳輸性的觀點而言，R ³¹更佳為可具有取代基的芳香族烴基。於存在多個作為取代基時的R ³¹的情況下，可相互不同。 (R ³¹ ) R ³¹ as a substituent is preferably an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms or an optionally substituted aromatic heterocyclic group having 3 to 30 carbon atoms. R ³¹ is more preferably an aromatic hydrocarbon group which may have a substituent from the viewpoint of durability improvement and charge transportability. When a plurality of R ³¹ are present as substituents, they may be different from each other.

作為所述碳數6～30的芳香族烴基可具有的取代基、碳數3～30的芳香族雜環基可具有的取代基、作為取代基的R ³¹可具有的取代基，可自下述取代基群組Z2中選擇。 As the substituent that the aromatic hydrocarbon group having 6 to 30 carbon atoms may have, the substituent that the aromatic heterocyclic group having 3 to 30 carbon atoms may have, and the substituent that ^R31 may have as a substituent may be selected from the following: selected from the above-mentioned substituent group Z2.

（取代基群組Z2）取代基群組Z2為包含烷基、烷氧基、芳氧基、雜芳氧基、烷氧基羰基、二烷基胺基、二芳基胺基、芳基烷基胺基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、氰基、芳香族烴基、及芳香族雜環基的群組。該些取代基亦可包含直鏈、分支及環狀的任一結構。 (substituent group Z2) The substituent group Z2 includes alkyl, alkoxy, aryloxy, heteroaryloxy, alkoxycarbonyl, dialkylamine, diarylamine, arylalkylamine, acyl, Groups of halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, cyano groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups. These substituents may also include any structure of linear, branched and cyclic.

作為取代基群組Z2，更具體而言，可列舉以下的結構。例如甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正己基、環己基、十二烷基等碳數通常為1以上、較佳為4以上且通常為24以下、較佳為12以下、更佳為8以下、進而佳為6以下的直鏈、分支、或環狀的烷基；例如甲氧基、乙氧基等碳數通常為1以上且通常為24以下、較佳為12以下的烷氧基；例如苯氧基、萘氧基、吡啶氧基等碳數通常為4以上、較佳為5以上且通常為36以下、較佳為24以下的芳氧基或雜芳氧基；例如甲氧基羰基、乙氧基羰基等碳數通常為2以上且通常為24以下、較佳為12以下的烷氧基羰基；例如二甲基胺基、二乙基胺基等碳數通常為2以上且通常為24以下、較佳為12以下的二烷基胺基；例如二苯基胺基、二甲苯基胺基等碳數通常為10以上、較佳為12以上且通常為36以下、較佳為24以下的二芳基胺基；例如苯基甲基胺基等碳數通常為7以上且通常為36以下、較佳為24以下的芳基烷基胺基；例如乙醯基、苯甲醯基等碳數通常為2以上且通常為24以下、較佳為12的醯基；例如氟原子、氯原子等鹵素原子；例如三氟甲基等碳數通常為1以上且通常為12以下、較佳為6以下的鹵代烷基；例如甲硫基、乙硫基等碳數通常為1以上且通常為24以下、較佳為12以下的烷硫基；例如苯硫基、萘硫基、吡啶硫基等碳數通常為4以上、較佳為5以上且通常為36以下、較佳為24以下的芳硫基；例如三甲基矽烷基、三苯基矽烷基等碳數通常為2以上、較佳為3以上且通常為36以下、較佳為24以下的矽烷基；例如三甲基矽氧基、三苯基矽氧基等碳數通常為2以上、較佳為3以上且通常為36以下、較佳為24以下的矽氧基；氰基；例如苯基、萘基等碳數通常為6以上且通常為36以下、較佳為24以下的芳香族烴基；例如乙炔基、吡啶基等碳數通常為3以上、較佳為4以上且通常為36以下、較佳為24以下的芳香族雜環基。 More specifically, the substituent group Z2 includes the following structures. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second-butyl, third-butyl, n-hexyl, cyclohexyl, dodecyl, etc. usually have 1 or more carbon atoms , preferably 4 or more and usually 24 or less, preferably 12 or less, more preferably 8 or less, and further preferably 6 or less straight-chain, branched, or cyclic alkyl; For example, alkoxy groups such as methoxy, ethoxy and the like are usually more than 1 and usually less than 24, preferably less than 12; For example, aryloxy or heteroaryloxy groups with a carbon number of usually 4 or more, preferably 5 or more, and usually 36 or less, preferably 24 or less, such as phenoxy, naphthyloxy, and pyridyloxy; For example, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl and the like are usually more than 2 and usually less than 24, preferably less than 12; For example, a dialkylamine group with a carbon number of more than 2 and usually less than 24, preferably less than 12, such as a dimethylamino group and a diethylamino group; For example, a diarylamine group with a carbon number of usually more than 10, preferably more than 12, and usually less than 36, preferably less than 24, such as diphenylamino and xylylamino; For example, an arylalkylamine group whose carbon number is usually more than 7 and usually less than 36, preferably less than 24, such as a phenylmethylamine group; For example, an acyl group with a carbon number of more than 2 and usually less than 24, preferably 12, such as acetyl and benzoyl; For example, halogen atoms such as fluorine atoms and chlorine atoms; For example, a haloalkyl group with a carbon number of usually more than 1 and usually less than 12, preferably less than 6, such as trifluoromethyl; For example, methylthio, ethylthio and other alkylthio groups with a carbon number of usually more than 1 and usually less than 24, preferably less than 12; For example, arylthio groups such as phenylthio, naphthylthio, pyridylthio and the like are usually 4 or more, preferably 5 or more, and usually 36 or less, preferably 24 or less; For example, trimethylsilyl, triphenylsilyl, and other silyl groups with carbon numbers of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less; For example, trimethylsilyloxy, triphenylsilyloxy and other silyloxy groups with a carbon number of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less; cyano; For example, phenyl, naphthyl and other aromatic hydrocarbon groups with a carbon number of usually more than 6 and usually less than 36, preferably less than 24; For example, an aromatic heterocyclic group having a carbon number of usually 3 or more, preferably 4 or more, and usually 36 or less, preferably 24 or less, such as ethynyl and pyridyl.

所述取代基群組Z2中，較佳為烷基、烷氧基、二芳基胺基、芳香族烴基、或芳香族雜環基。就電荷傳輸性的觀點而言，作為取代基，更佳為芳香族烴基或芳香族雜環基，進而佳為芳香族烴基，特佳為不具有取代基。就提高溶解性的觀點而言，作為取代基，較佳為烷基或烷氧基。In the substituent group Z2, it is preferably an alkyl group, an alkoxy group, a diarylamine group, an aromatic hydrocarbon group, or an aromatic heterocyclic group. From the viewpoint of charge transport properties, the substituent is more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, more preferably an aromatic hydrocarbon group, and particularly preferably has no substituent. From the viewpoint of improving solubility, the substituent is preferably an alkyl group or an alkoxy group.

所述取代基群組Z2的各取代基亦可更具有取代基。作為該些取代基，可列舉與所述取代基（取代基群組Z2）相同的取代基。所述取代基群組Z2可具有的各取代基較佳為碳數8以下的烷基、碳數8以下的烷氧基、或苯基，更佳為碳數6以下的烷基、碳數6以下的烷氧基、或苯基。就電荷傳輸性的觀點而言，所述取代基群組Z2的各取代基更佳為不具有進一步的取代基。Each substituent of the substituent group Z2 may further have a substituent. Examples of these substituents include the same substituents as those described above (substituent group Z2). Each substituent that the substituent group Z2 may have is preferably an alkyl group having 8 or less carbons, an alkoxy group having 8 or fewer carbons, or a phenyl group, more preferably an alkyl group having 6 or fewer carbons, or an alkyl group having 6 or fewer carbons. 6 or less alkoxy, or phenyl. From the viewpoint of charge transportability, each substituent of the substituent group Z2 preferably has no further substituent.

（分子量）式（250）所表示的化合物為低分子材料。式（250）所表示的化合物的分子量較佳為3,000以下，更佳為3,000以下，進而佳為2,000以下，特佳為1,500以下。該化合物的分子量的下限通常為300以上，較佳為350以上，更佳為400以上。 (molecular weight) The compound represented by formula (250) is a low molecular weight material. The molecular weight of the compound represented by formula (250) is preferably 3,000 or less, more preferably 3,000 or less, still more preferably 2,000 or less, particularly preferably 1,500 or less. The lower limit of the molecular weight of the compound is usually 300 or more, preferably 350 or more, more preferably 400 or more.

（式（250）所表示的化合物的具體例）式（250）所表示的化合物並無特別限定，例如可列舉以下的化合物。 (Specific examples of compounds represented by formula (250)) The compound represented by formula (250) is not particularly limited, and examples thereof include the following compounds.

[化47]

[chem 47]

[化48]

[chem 48]

於本發明的組成物中可僅包含式（250）所表示的化合物中的一種，亦可包含兩種以上。The composition of the present invention may contain only one kind of compounds represented by formula (250), or may contain two or more kinds thereof.

＜式（240）所表示的化合物＞ [化49]

<Compound represented by formula (240)> [Chem. 49]

（Ar ⁶¹¹、Ar ⁶¹²） Ar ⁶¹¹、Ar ⁶¹²各自獨立地表示可具有取代基的碳數6～50的一價芳香族烴基。芳香族烴基的碳數通常為6～50，較佳為6～30，更佳為6～18。作為芳香族烴基，具體而言，可列舉苯環、萘環、蒽環、四伸苯環、菲環、䓛環、芘環、苯並蒽環、或苝環等碳數通常為6以上且通常為30以下、較佳為18以下、進而佳為14以下的芳香族烴結構的一價基、或選自該些結構中的多個結構以鏈狀或分支的方式鍵結的結構的一價基。於芳香族烴環連結多個的情況下，通常可列舉連結兩個～八個的結構，較佳為連結兩個～五個的結構。於芳香族烴環連結多個的情況下，可連結相同的結構，亦可連結不同的結構。 (Ar ⁶¹¹ , Ar ⁶¹² ) Ar ⁶¹¹ and Ar ⁶¹² each independently represent a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. The carbon number of an aromatic hydrocarbon group is 6-50 normally, Preferably it is 6-30, More preferably, it is 6-18. Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a phenylenyl ring, a phenanthrene ring, a phenanthrene ring, a pyrene ring, a benzoanthracene ring, or a perylene ring, etc., which have a carbon number of usually 6 or more and Usually 30 or less, preferably 18 or less, and more preferably 14 or less, a monovalent group of an aromatic hydrocarbon structure, or a structure in which a plurality of structures selected from these structures are bonded in a chain or branched manner price base. When a plurality of aromatic hydrocarbon rings are linked, usually two to eight structures are mentioned, preferably two to five structures. When a plurality of aromatic hydrocarbon rings are linked, the same structure may be linked or different structures may be linked.

Ar ⁶¹¹、Ar ⁶¹²較佳為各自獨立地為苯基、多個苯環以鏈狀或分支的方式鍵結而成的一價基，一個或多個苯環及至少一個萘環以鏈狀或分支的方式鍵結而成的一價基，一個或多個苯環及至少一個菲環以鏈狀或分支的方式鍵結而成的一價基、或者一個或多個苯環及至少一個四伸苯環以鏈狀或分支的方式鍵結而成的一價基，該些亦可具有取代基。進而佳為多個苯環以鏈狀或分支的方式鍵結而成的一價基。於任一情況下，鍵結的順序均無問題。 Ar ⁶¹¹、Ar ⁶¹²特佳為各自獨立地為可具有取代基的多個苯環以鏈狀或分支的方式鍵結而成的一價基，最佳為各自獨立地為多個苯環以鏈狀或分支的方式鍵結多個而成的一價基。 Ar ⁶¹¹ and Ar ⁶¹² are each independently preferably a phenyl group, a monovalent group in which multiple benzene rings are chained or branched, and one or more benzene rings and at least one naphthalene ring are chained or A monovalent group bonded in a branched manner, a monovalent group formed by one or more benzene rings and at least one phenanthrene ring bonded in a chain or branched manner, or one or more benzene rings and at least one tetra A monovalent group in which phenylene rings are chained or branched, and these may have a substituent. Furthermore, it is preferably a monovalent group in which a plurality of benzene rings are bonded in a chain or branched manner. In either case, the order of the bonds is not a problem. Ar ⁶¹¹ and Ar ⁶¹² are preferably each independently a monovalent group in which a plurality of benzene rings that may have substituents are bonded in a chain or a branched manner, and are most preferably each independently a plurality of benzene rings in a chain. A monovalent group formed by bonding multiple groups in the form of a shape or a branch.

所鍵結的苯環、萘環、菲環及四伸苯環的數量如所述般，通常為2～8，較佳為2～5。其中，較佳為連結有一個～四個苯環的一價基、連結有一個～四個苯環及萘環的一價基、連結有一個～四個苯環及菲環的一價基、或者連結有一個～四個苯環及四伸苯環的一價基。The number of bonded benzene rings, naphthalene rings, phenanthrene rings and phenylene rings is usually 2-8, preferably 2-5, as described above. Among them, preferred are monovalent groups with one to four benzene rings, monovalent groups with one to four benzene rings and naphthalene rings, monovalent groups with one to four benzene rings and phenanthrene rings, Or a monovalent group with one to four benzene rings and four extended phenyl rings linked.

該些芳香族烴基亦可具有取代基。芳香族烴基可具有的取代基可自所述取代基群組Z2中選擇。較佳的取代基為所述取代基群組Z2中的較佳的取代基。These aromatic hydrocarbon groups may have a substituent. The substituent which the aromatic hydrocarbon group may have can be selected from the said substituent group Z2. Preferred substituents are preferred substituents in the substituent group Z2.

就化合物的溶解性及耐久性的觀點而言，Ar ⁶¹¹、Ar ⁶¹²的至少一者較佳為具有選自下述式（72-1）～式（72-7）中的至少一個部分結構。 From the viewpoint of the solubility and durability of the compound, at least one of Ar ⁶¹¹ and Ar ⁶¹² preferably has at least one partial structure selected from the following formulas (72-1) to (72-7).

[化50]

[chemical 50]

於所述式（72-1）～式（72-7）各個中，*表示與鄰接的結構的鍵或氫原子。存在兩個的*中的至少一者表示與鄰接的結構的鍵結位置。於以後的記載中，只要無特別說明，則*的定義亦相同。In each of the formulas (72-1) to (72-7), * represents a bond to an adjacent structure or a hydrogen atom. At least one of two * indicates a bonding position with an adjacent structure. In the following description, unless otherwise specified, the definition of * is also the same.

更佳為Ar ⁶¹¹、Ar ⁶¹²的至少一者具有選自式（72-1）～式（72-4）及式（72-7）中的至少一個部分結構。進而佳為Ar ⁶¹¹、Ar ⁶¹²分別具有選自式（72-1）～式（72-3）及式（72-7）中的至少一個部分結構。特佳為Ar ⁶¹¹、Ar ⁶¹²分別具有選自式（72-1）、式（72-2）及式（72-7）中的至少一個部分結構。 More preferably, at least one of Ar ⁶¹¹ and Ar ⁶¹² has at least one partial structure selected from formula (72-1) to formula (72-4) and formula (72-7). Further preferably, Ar ⁶¹¹ and Ar ⁶¹² each have at least one partial structure selected from formula (72-1) to formula (72-3) and formula (72-7). Most preferably, Ar ⁶¹¹ and Ar ⁶¹² each have at least one partial structure selected from formula (72-1), formula (72-2) and formula (72-7).

作為式（72-2），較佳為下述式（72-2-2）。As formula (72-2), the following formula (72-2-2) is preferable.

[化51]

[Chemical 51]

作為式（72-2），更佳為下述式（72-2-3）。As formula (72-2), the following formula (72-2-3) is more preferable.

[化52]

[Chemical 52]

另外，就化合物的溶解性及耐久性的觀點而言，作為Ar ⁶¹¹、Ar ⁶¹²的至少一個較佳具有的部分結構，可列舉式（72-1）所表示的部分結構及式（72-2）所表示的部分結構。 In addition, from the viewpoint of the solubility and durability of the compound, at least one of Ar ⁶¹¹ and Ar ⁶¹² preferably has a partial structure including the partial structure represented by formula (72-1) and formula (72-2 ) represents the partial structure.

（R ⁶¹¹、R ⁶¹²） R ⁶¹¹、R ⁶¹²各自獨立地為氘原子、氟原子等鹵素原子、可具有取代基的碳數6～50的一價芳香族烴基。較佳為可具有取代基的碳數6～50的一價芳香族烴基。作為芳香族烴基，可列舉進而佳為碳數6～30、更佳為6～18、特佳為6～10的芳香族烴環的一價基。作為一價芳香族烴基，具體而言與所述Ar ⁶¹¹相同，較佳的芳香族烴基亦相同，特佳為苯基。該些芳香族烴基亦可具有取代基。芳香族烴基可具有的取代基如所述般，具體而言，可自所述取代基群組Z2中選擇。較佳的取代基為所述取代基群組Z2中的較佳的取代基。 (R ⁶¹¹ , R ⁶¹² ) R ⁶¹¹ and R ⁶¹² are each independently a halogen atom such as a deuterium atom or a fluorine atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. It is preferably a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. The aromatic hydrocarbon group is further preferably a monovalent group having 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 10 aromatic hydrocarbon rings. The monovalent aromatic hydrocarbon group is specifically the same as Ar ⁶¹¹ , and the preferred aromatic hydrocarbon group is also the same, particularly preferably a phenyl group. These aromatic hydrocarbon groups may have a substituent. The substituents that the aromatic hydrocarbon group may have are as described above, specifically, they can be selected from the substituent group Z2. Preferred substituents are preferred substituents in the substituent group Z2.

（n ⁶¹¹、n ⁶¹²） n ⁶¹¹、n ⁶¹²各自獨立地為0～4的整數。n ⁶¹¹、n ⁶¹²各自獨立地較佳為0～2，進而佳為0或1。 (n ⁶¹¹ , n ⁶¹² ) n ⁶¹¹ , n ⁶¹² are each independently an integer of 0-4. n ⁶¹¹ and n ⁶¹² are each independently preferably 0-2, more preferably 0 or 1.

（取代基）於Ar ⁶¹¹、Ar ⁶¹²、R ⁶¹¹、R ⁶¹²為一價或二價的芳香族烴基的情況下，可具有的取代基較佳為選自所述取代基群組Z2中的取代基。 (Substituents) When Ar ⁶¹¹ , Ar ⁶¹² , R ⁶¹¹ , and R ⁶¹² are monovalent or divalent aromatic hydrocarbon groups, the optional substituents are preferably those selected from the substituent group Z2. base.

（G） G表示單鍵、或可具有取代基的碳數6～50的二價芳香族烴基。 (G) G represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.

G中的芳香族烴基的碳數通常為6～50，較佳為6～30，更佳為6～18。作為芳香族烴基，具體而言，可列舉苯環、萘環、蒽環、四伸苯環、菲環、䓛環、芘環、苯並蒽環、或苝環等碳數通常為6以上且通常為30以下、較佳為18以下、進而佳為14以下的芳香族烴結構的二價基、或選自該些結構中的多個結構以鏈狀或分支的方式鍵結的結構的二價基。於芳香族烴環連結多個的情況下，通常可列舉連結兩個～八個的結構，較佳為連結兩個～五個的結構。於芳香族烴環連結多個的情況下，可連結相同的結構，亦可連結不同的結構。The carbon number of the aromatic hydrocarbon group in G is 6-50 normally, Preferably it is 6-30, More preferably, it is 6-18. Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a phenylenyl ring, a phenanthrene ring, a phenanthrene ring, a pyrene ring, a benzoanthracene ring, or a perylene ring, etc., which have a carbon number of usually 6 or more and Usually 30 or less, preferably 18 or less, and more preferably 14 or less divalent groups of aromatic hydrocarbon structures, or divalent groups selected from these structures in which multiple structures are bonded in chains or branches. price base. When a plurality of aromatic hydrocarbon rings are linked, usually two to eight structures are mentioned, preferably two to five structures. When a plurality of aromatic hydrocarbon rings are linked, the same structure may be linked or different structures may be linked.

G較佳為單鍵、伸苯基、多個苯環以鏈狀或分支的方式鍵結而成的二價基，一個或多個苯環及至少一個萘環以鏈狀或分支的方式鍵結而成的二價基，一個或多個苯環及至少一個菲環以鏈狀或分支的方式鍵結而成的二價基、或者一個或多個苯環及至少一個四伸苯環以鏈狀或分支的方式鍵結而成的二價基，進而佳為多個苯環以鏈狀或分支的方式鍵結而成的二價基。於任一情況下，鍵結的順序均無問題。 G is preferably single bond, phenylene, A divalent group in which multiple benzene rings are bonded in chains or branches, A divalent group formed by one or more benzene rings and at least one naphthalene ring bonded in a chain or branched manner, A divalent group formed by one or more benzene rings and at least one phenanthrene ring bonded in a chain or branched manner, or A divalent group formed by one or more benzene rings and at least one four-strand phenylene ring bonded in a chain or branched manner, Furthermore, a divalent group in which a plurality of benzene rings are chained or branched is preferable. In either case, the order of the bonds is not a problem.

所鍵結的苯環、萘環、菲環及四伸苯環的數量如所述般，通常為2～8，較佳為2～5。其中，進而佳為連結有一個～四個苯環的二價基、連結有一個～四個苯環及萘環的二價基、連結有一個～四個苯環及菲環的二價基、或者連結有一個～四個苯環及四伸苯環的二價基。The number of bonded benzene rings, naphthalene rings, phenanthrene rings and phenylene rings is usually 2-8, preferably 2-5, as described above. Among them, a divalent group with one to four benzene rings connected, a divalent group with one to four benzene rings and a naphthalene ring connected, a divalent group with one to four benzene rings and a phenanthrene ring connected, Or a divalent group with one to four benzene rings and four phenylene rings linked.

（分子量）所述式（240）所表示的化合物為低分子材料，其分子量較佳為3,000以下，更佳為2,500以下，進而佳為2,000以下，特佳為1,500以下，且通常為300以上，較佳為350以上，更佳為400以上。 (molecular weight) The compound represented by the formula (240) is a low-molecular material, and its molecular weight is preferably 3,000 or less, more preferably 2,500 or less, further preferably 2,000 or less, particularly preferably 1,500 or less, and usually 300 or more, preferably More than 350, more preferably more than 400.

（式（240）所表示的化合物的具體例）以下示出式（240）所表示的化合物的較佳的具體例，但本發明並不限定於該些。 (Specific examples of compounds represented by formula (240)) Preferred specific examples of the compound represented by the formula (240) are shown below, but the present invention is not limited thereto.

[化53]

[Chemical 53]

於本發明的組成物中可僅包含式（240）所表示的化合物中的一種，亦可包含兩種以上。The composition of the present invention may contain only one kind of compounds represented by formula (240), or may contain two or more kinds thereof.

＜其他成分＞本發明的組成物除了包含所述有機溶劑及發光材料以外，視需要亦可包含各種其他溶劑。作為此種其他溶劑，例如可列舉：N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類、二甲基亞碸等。＜Other ingredients＞ The composition of the present invention may contain various other solvents as needed, in addition to the above-mentioned organic solvent and luminescent material. Examples of such other solvents include amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethylsulfoxide, and the like.

本發明的組成物亦可包含調平劑或消泡劑等各種添加劑。本發明的組成物於利用濕式成膜法積層兩層以上的層時，為了防止該些層相溶，出於在成膜後使其硬化而不溶化的目的，亦可含有光硬化性樹脂或熱硬化性樹脂。 The composition of the present invention may also contain various additives such as a leveling agent or an antifoaming agent. When the composition of the present invention laminates two or more layers by a wet film-forming method, in order to prevent these layers from being compatible, for the purpose of making it harden and insoluble after film formation, it may also contain a photocurable resin or Thermosetting resin.

＜調配比＞本發明的組成物中的固體成分濃度（包含本發明的芳香族化合物、發光材料、本發明的芳香族化合物以外的主體材料及視需要能夠添加的成分（調平劑等）等的全部固體成分的濃度）通常為0.01質量%以上，較佳為0.05質量%以上，更佳為0.1質量%以上，進而佳為0.5質量%以上，最佳為1質量%以上，且通常為80質量%以下，較佳為50質量%以下，更佳為40質量%以下，進而佳為30質量%以下，最佳為20質量%以下。若固體成分濃度為該範圍，則容易以均勻的厚度形成所需的膜厚的薄膜而較佳。＜Mix ratio＞ Solid content concentration in the composition of the present invention (including the aromatic compound of the present invention, the luminescent material, host materials other than the aromatic compound of the present invention, and components that can be added if necessary (leveling agent, etc.) The concentration) is usually 0.01 mass % or more, preferably 0.05 mass % or more, more preferably 0.1 mass % or more, further preferably 0.5 mass % or more, most preferably 1 mass % or more, and usually 80 mass % or less, Preferably it is 50 mass % or less, More preferably, it is 40 mass % or less, More preferably, it is 30 mass % or less, Most preferably, it is 20 mass % or less. When the solid content concentration is within this range, it is easy to form a thin film having a desired film thickness with a uniform thickness, which is preferable.

本發明的芳香族化合物及發光材料相對於本發明的組成物中包含的全部主體材料的較佳的調配比、即本發明的化合物及發光材料相對於使用本發明的組成物而形成的發光層（以下，有時稱為「本發明的發光層」）中包含的全部主體材料的較佳的調配比如以下般。再者，所謂全部主體材料是指本發明的芳香族化合物及本發明的芳香族化合物以外的全部主體材料。The preferred compounding ratio of the aromatic compound and light-emitting material of the present invention to all the host materials contained in the composition of the present invention, that is, the compound of the present invention and the light-emitting material to the light-emitting layer formed using the composition of the present invention (Hereinbelow, it may be referred to as "the light-emitting layer of the present invention"). A preferable formulation ratio of all the host materials contained in it is as follows. In addition, the term "all host materials" refers to the aromatic compound of the present invention and all host materials other than the aromatic compound of the present invention.

本發明的組成物及本發明的發光層中本發明的芳香族化合物相對於全部主體材料的質量100而言的質量比通常為1以上，較佳為5以上，更佳為10以上，進而佳為15以上，且通常為90以下，較佳為80以下，更佳為70以下，特佳為50以下。In the composition of the present invention and the light-emitting layer of the present invention, the mass ratio of the aromatic compound of the present invention to the mass 100 of all host materials is usually 1 or more, preferably 5 or more, more preferably 10 or more, and even more preferably 15 or more, and usually 90 or less, preferably 80 or less, more preferably 70 or less, most preferably 50 or less.

本發明的組成物及本發明的發光層中本發明的芳香族化合物相對於全部主體材料的莫耳比通常為1莫耳%以上，較佳為5莫耳%以上，更佳為10莫耳%以上，特佳為15莫耳%以上，且通常為90莫耳%以下，較佳為80莫耳%以下，更佳為70莫耳%以下，特佳為60莫耳%以下。The molar ratio of the aromatic compound of the present invention to the entire host material in the composition of the present invention and the light-emitting layer of the present invention is usually 1 mol% or more, preferably 5 mol% or more, more preferably 10 mol% % or more, preferably more than 15 mol%, and usually less than 90 mol%, preferably less than 80 mol%, more preferably less than 70 mol%, especially preferably less than 60 mol%.

本發明的組成物及本發明的發光層中發光材料相對於全部主體材料的質量100而言的質量比通常為0.1以上，較佳為0.5以上，更佳為1以上，特佳為2以上，且通常為100以下，較佳為60以下，更佳為50以下，特佳為40以下。若該比低於所述下限、或超過所述上限，則發光效率有可能明顯降低。The mass ratio of the luminescent material in the composition of the present invention and the luminescent layer of the present invention relative to the mass of all host materials 100 is usually 0.1 or more, preferably 0.5 or more, more preferably 1 or more, and most preferably 2 or more, And it is usually 100 or less, preferably 60 or less, more preferably 50 or less, particularly preferably 40 or less. When the ratio is lower than the lower limit or exceeds the upper limit, there is a possibility that the luminous efficiency will significantly decrease.

＜組成物的製備方法＞本發明的組成物藉由使包含本發明的芳香族化合物、視需要的所述磷光發光材料等發光材料、電荷傳輸材料、及本發明的芳香族化合物以外的主體材料、以及視需要能夠添加的調平劑或消泡劑等各種添加成分的溶質溶解於所述適當的有機溶劑中來製備。＜How to prepare the composition＞ The composition of the present invention is made by including the aromatic compound of the present invention, light-emitting materials such as the above-mentioned phosphorescent luminescent material, charge transport material, and host materials other than the aromatic compound of the present invention, and optionally added The solute of various additive components such as a leveling agent and an antifoaming agent is prepared by dissolving in the above-mentioned appropriate organic solvent.

為了縮短該溶解步驟所需的時間，以及為了將本發明的組成物中的溶質濃度保持為均勻，通常一邊攪拌液體一邊溶解溶質。溶解步驟可於常溫下進行，但於溶解速度慢的情況下亦可加熱使其溶解。於溶解步驟結束後，視需要亦可經由過濾等過濾步驟。In order to shorten the time required for this dissolving step and to keep the concentration of the solute in the composition of the present invention uniform, the solute is usually dissolved while stirring the liquid. The dissolving step can be carried out at normal temperature, but it can also be heated to dissolve when the dissolution rate is slow. After completion of the dissolving step, a filtration step such as filtration may be performed if necessary.

＜組成物的性狀、物性等＞（水分濃度）於利用使用本發明的組成物的濕式成膜法形成層來製造有機電場發光元件的情況下，若於組成物中存在水分，則水分會混入至所形成的膜中而損害膜的均勻性。因此，本發明的組成物中的水分含量較佳為盡可能少。另外，一般而言，於有機電場發光元件中大多使用陰極等因水分而明顯劣化的材料，因此認為於組成物中存在水分的情況下，水分會殘留於乾燥後的膜中，有可能降低元件的特性，從而欠佳。＜Properties, physical properties, etc. of the composition＞ (moisture concentration) In the case of manufacturing an organic electroluminescent element by forming a layer by a wet film-forming method using the composition of the present invention, if moisture is present in the composition, the moisture will be mixed into the formed film to impair the uniformity of the film. . Therefore, the moisture content in the composition of the present invention is preferably as small as possible. In addition, in general, materials that are significantly degraded by moisture, such as cathodes, are often used in organic electroluminescent devices. Therefore, it is considered that when moisture exists in the composition, the moisture will remain in the dried film, which may degrade the device. characteristics, which are not good.

具體而言，本發明的組成物中包含的水分量通常為1質量%以下，較佳為0.1質量%以下，更佳為0.01質量%以下。Specifically, the amount of moisture contained in the composition of the present invention is usually 1% by mass or less, preferably 0.1% by mass or less, more preferably 0.01% by mass or less.

作為組成物中的水分濃度的測定方法，較佳為日本工業標準「化學製品的水分測定法」（日本工業標準（Japanese Industrial Standards，JIS）K0068：2001）中記載的方法。例如，可藉由卡耳-費雪試劑（Karl Fischer's reagent）法（JIS K0211-1348）等進行分析。The method for measuring the water concentration in the composition is preferably the method described in the Japanese Industrial Standard "Method for Measuring Moisture in Chemical Products" (Japanese Industrial Standards (JIS) K0068:2001). For example, it can be analyzed by the Karl Fischer's reagent method (JIS K0211-1348) or the like.

（均勻性）為了提高濕式成膜製程中的穩定性、例如噴墨成膜法中的自噴嘴的噴出穩定性，本發明的組成物較佳為於常溫下為均勻的液狀。所謂於常溫下均勻的液狀是指組成物為包含均勻相的液體，且組成物中不含有粒徑0.1 μm以上的粒子成分。 (Uniformity) In order to improve the stability in the wet film forming process, such as the ejection stability from the nozzle in the inkjet film forming method, the composition of the present invention is preferably in a uniform liquid state at room temperature. The term "homogeneous liquid at normal temperature" means that the composition is a liquid containing a homogeneous phase, and the composition does not contain particle components having a particle diameter of 0.1 μm or more.

（物性）於本發明的組成物的黏度為極低的黏度的情況下，例如容易發生由成膜步驟中的過度的液膜流動引起的塗面不均勻、噴墨成膜中的噴嘴噴出不良等。於本發明的組成物的黏度為極高的黏度的情況下，容易發生噴墨成膜中的噴嘴堵塞等。因此，本發明的組成物於25℃下的黏度通常為2 mPa·s以上，較佳為3 mPa·s以上，更佳為5 mPa·s以上，且通常為1000 mPa·s以下，較佳為100 mPa·s以下，更佳為50 mPa·s以下。 (physical properties) In the case where the viscosity of the composition of the present invention is extremely low, for example, uneven coating due to excessive liquid film flow in the film forming step, nozzle ejection failure in inkjet film forming, and the like tend to occur. When the viscosity of the composition of the present invention is extremely high, nozzle clogging and the like during inkjet film formation tend to occur. Therefore, the viscosity of the composition of the present invention at 25°C is usually above 2 mPa·s, preferably above 3 mPa·s, more preferably above 5 mPa·s, and usually below 1000 mPa·s, preferably 100 mPa·s or less, more preferably 50 mPa·s or less.

於本發明的組成物的表面張力高的情況下，有時會產生如下問題：相對於基板的潤濕性降低，液膜的調平性差，乾燥時容易引起成膜面混亂等。因此，本發明的組成物於20℃下的表面張力通常未滿50 mN/m，較佳為未滿40 mN/m。 When the surface tension of the composition of the present invention is high, there may be problems such as reduced wettability to the substrate, poor leveling of the liquid film, and easy disturbance of the film-forming surface during drying. Therefore, the surface tension of the composition of the present invention at 20° C. is usually less than 50 mN/m, preferably less than 40 mN/m.

於本發明的組成物的蒸氣壓高的情況下，有時容易引起由有機溶劑的蒸發所致的溶質濃度變化等問題。因此，本發明的組成物於25℃下的蒸氣壓通常為50 mmHg以下，較佳為10 mmHg以下，更佳為1 mmHg以下。 When the vapor pressure of the composition of the present invention is high, problems such as changes in solute concentration due to evaporation of the organic solvent may easily occur. Therefore, the vapor pressure of the composition of the present invention at 25° C. is usually below 50 mmHg, preferably below 10 mmHg, more preferably below 1 mmHg.

[薄膜形成方法] 本發明的薄膜形成方法中的利用本發明的組成物的成膜方法為濕式成膜法。濕式成膜法是指塗佈組成物形成液膜並進行乾燥而去除有機溶劑來形成膜的方法。於本發明的組成物包含發光材料的情況下，可利用該方法來形成發光層。是指如下方法：例如採用利用旋塗法、浸塗法、模塗法、棒塗法、刮塗法、輥塗法、噴塗法、毛細管塗佈法、噴墨法、噴嘴印刷法、網版印刷法、凹版印刷法、柔版印刷法等濕式來成膜的方法作為塗佈方法，並使塗佈膜乾燥而進行膜形成。該些成膜方法中，較佳為旋塗法、噴塗法、噴墨法、噴嘴印刷法等。於製造包括有機電場發光元件的有機EL顯示裝置的情況下，較佳為噴墨法或噴嘴印刷法，特佳為噴墨法。 [Film Formation Method] The film forming method using the composition of the present invention in the thin film forming method of the present invention is a wet film forming method. The wet film-forming method refers to a method of forming a film by applying a composition to form a liquid film and drying it to remove an organic solvent. When the composition of the present invention contains a light-emitting material, this method can be used to form a light-emitting layer. Refers to methods such as spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet, nozzle printing, screen printing, etc. A wet film-forming method such as a printing method, a gravure printing method, and a flexographic printing method is used as a coating method, and the coating film is dried to form a film. Among these film forming methods, spin coating method, spray coating method, inkjet method, nozzle printing method and the like are preferable. In the case of manufacturing an organic EL display device including an organic electroluminescence element, an inkjet method or a nozzle printing method is preferable, and an inkjet method is particularly preferable.

乾燥方法並無特別限定，可適宜使用自然乾燥、減壓乾燥、加熱乾燥、或一邊加熱一邊減壓乾燥。加熱乾燥亦可於自然乾燥或減壓乾燥後，為了進一步去除殘留有機溶劑而實施。The drying method is not particularly limited, and natural drying, drying under reduced pressure, drying under reduced pressure, or drying under reduced pressure while heating can be suitably used. Drying by heating may also be carried out in order to further remove residual organic solvents after natural drying or drying under reduced pressure.

較佳為於減壓乾燥中，減壓至本發明的組成物中包含的有機溶劑的蒸氣壓以下。It is preferable to reduce the pressure to below the vapor pressure of the organic solvent contained in the composition of the present invention in the reduced-pressure drying.

於進行加熱乾燥的情況下，加熱方法並無特別限定，可使用利用加熱板進行的加熱、烘箱內的加熱、紅外線加熱等。加熱溫度通常為80℃以上，較佳為100℃以上，更佳為110℃以上，另外較佳為200℃以下，更佳為150℃以下。加熱時間通常為1分鐘以上，較佳為2分鐘以上，且通常為60分鐘以下，較佳為30分鐘以下，更佳為20分鐘以下。 When heat drying is performed, the heating method is not particularly limited, and heating with a hot plate, heating in an oven, infrared heating, and the like can be used. The heating temperature is usually above 80°C, preferably above 100°C, more preferably above 110°C, and preferably below 200°C, more preferably below 150°C. The heating time is usually not less than 1 minute, preferably not less than 2 minutes, and usually not more than 60 minutes, preferably not more than 30 minutes, more preferably not more than 20 minutes.

如後述般，於有機電場發光元件中，於發光層上形成電子傳輸層。本發明中，較佳為使用本發明的組成物並利用濕式成膜法形成發光層，與該發光層上相接並利用濕式成膜法形成電子傳輸層等層。As will be described later, in the organic electroluminescent device, the electron transport layer is formed on the light emitting layer. In the present invention, it is preferable to form a light-emitting layer by a wet film-forming method using the composition of the present invention, and form layers such as an electron-transporting layer in contact with the light-emitting layer by a wet film-forming method.

與發光層相接並利用濕式成膜法形成電子傳輸層時使用的電子傳輸層形成用組成物至少包含電子傳輸層材料及溶劑。作為該電子傳輸層形成用組成物的溶劑，就難溶本發明的芳香族化合物且耐溶劑性優異而言，較佳為醇系溶劑（具有醇性羥基的溶劑）。另外，作為電子傳輸層形成用組成物的電子傳輸層材料，較佳為可溶於此種醇系溶劑的電子傳輸性材料。The composition for forming an electron transport layer used when the electron transport layer is formed in contact with the light-emitting layer by a wet film-forming method contains at least an electron transport layer material and a solvent. The solvent of the composition for forming an electron transport layer is preferably an alcoholic solvent (a solvent having an alcoholic hydroxyl group) since it hardly dissolves the aromatic compound of the present invention and has excellent solvent resistance. In addition, the electron-transporting layer material as the electron-transporting layer-forming composition is preferably an electron-transporting material soluble in such an alcohol-based solvent.

作為醇系溶劑，較佳為碳數3以上的脂肪族醇。就容易溶解電子傳輸性材料的方面及具有適度高的沸點、容易形成平坦的膜的方面而言，更佳為碳數6以上的脂肪族醇。 The alcohol-based solvent is preferably an aliphatic alcohol having 3 or more carbon atoms. The aliphatic alcohol having 6 or more carbon atoms is more preferable in terms of easily dissolving the electron transport material, having a moderately high boiling point, and being easy to form a flat film.

關於作為醇系溶劑而較佳的脂肪族醇，可列舉：1-丁醇、異丁醇、2-己醇、1-己醇、1-庚醇、2-甲基-2-戊醇、4-甲基-3-庚醇、3-甲基-2-戊醇、4-甲基-1-戊醇、4-庚醇、1-甲氧基-2-丙醇、3-甲基-1-戊醇、4-辛醇、3-(甲基胺基)-1-丙醇等。該些醇系溶劑亦可將兩種以上混合而使用。Preferable aliphatic alcohols as alcoholic solvents include: 1-butanol, isobutanol, 2-hexanol, 1-hexanol, 1-heptanol, 2-methyl-2-pentanol, 4-Methyl-3-heptanol, 3-methyl-2-pentanol, 4-methyl-1-pentanol, 4-heptanol, 1-methoxy-2-propanol, 3-methyl - 1-pentanol, 4-octanol, 3-(methylamino)-1-propanol and the like. These alcohol-based solvents may be used in combination of two or more.

利用濕式成膜法的電子傳輸層形成方法較佳為使用所述發光層的成膜方法中敘述的濕式成膜法。The method for forming the electron transport layer by a wet film-forming method is preferably the wet film-forming method described in the film-forming method using the light-emitting layer.

[有機電場發光元件] 作為本發明的有機電場發光元件的結構的一例，於圖1中表示有機電場發光元件8的結構例的示意圖（剖面）。於圖1中，1表示基板，2表示陽極，3表示電洞注入層，4表示電洞傳輸層，5表示發光層，6表示電子傳輸層，7表示陰極。 [Organic electroluminescence device] As an example of the structure of the organic electroluminescent element of the present invention, a schematic view (cross section) of a structural example of the organic electroluminescent element 8 is shown in FIG. 1 . In FIG. 1 , 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transport layer, 5 denotes a light-emitting layer, 6 denotes an electron transport layer, and 7 denotes a cathode.

＜基板＞基板1為有機電場發光元件的支撐體，通常可使用石英或玻璃的板、金屬板或金屬箔、塑膠膜或片等。該些中，較佳為玻璃板、或聚酯、聚甲基丙烯酸酯、聚碳酸酯、聚碸等透明的合成樹脂的板。就不易發生由外部氣體引起的有機電場發光元件的劣化而言，基板較佳為設為阻氣性高的材質。因此，特別是於使用合成樹脂製的基板等般阻氣性低的材質的情況下，較佳為於基板的至少單面設置緻密的矽氧化膜等來提高阻氣性。＜Substrate＞ The substrate 1 is the support body of the organic electroluminescent element, usually a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, etc. can be used. Among these, a glass plate, or a plate of transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polyester is preferable. The substrate is preferably made of a material with a high gas barrier property in terms of being less likely to cause degradation of the organic electroluminescent element due to external air. Therefore, especially when a material with low gas barrier properties such as a synthetic resin substrate is used, it is preferable to provide a dense silicon oxide film or the like on at least one surface of the substrate to improve the gas barrier properties.

＜陽極＞陽極2承擔對發光層5側的層注入電洞的功能。＜Anode＞ The anode 2 has the function of injecting holes into the layer on the light emitting layer 5 side.

陽極2通常包含：鋁、金、銀、鎳、鈀、鉑等金屬；銦及/或錫的氧化物等金屬氧化物；碘化銅等鹵化金屬；碳黑及聚(3-甲基噻吩)、聚吡咯、聚苯胺等導電性高分子等。The anode 2 usually includes: metals such as aluminum, gold, silver, nickel, palladium, platinum; metal oxides such as indium and/or tin oxides; metal halides such as copper iodide; carbon black and poly(3-methylthiophene) , polypyrrole, polyaniline and other conductive polymers.

陽極2的形成通常大多藉由濺鍍法、真空蒸鍍法等乾式法來進行。於使用銀等金屬微粒子、碘化銅等微粒子、碳黑、導電性的金屬氧化物微粒子、導電性高分子微粉末等來形成陽極的情況下，亦可藉由分散於適當的黏合劑樹脂溶液並塗佈於基板上來形成。另外，於導電性高分子的情況下，亦可藉由電解聚合直接於基板上形成薄膜、或於基板上塗佈導電性高分子來形成陽極（應用物理快報（Appl. Phys. Lett.），60卷，2711頁，1992年）。Formation of the anode 2 is generally performed by dry methods such as sputtering and vacuum deposition. In the case of using metal particles such as silver, particles such as copper iodide, carbon black, conductive metal oxide particles, conductive polymer fine powder, etc. to form the anode, it can also be dispersed in an appropriate binder resin solution And coated on the substrate to form. In addition, in the case of conductive polymers, it is also possible to form a thin film directly on a substrate by electrolytic polymerization, or to coat a conductive polymer on a substrate to form an anode (Appl. Phys. Lett., 60, pp. 2711, 1992).

陽極2通常為單層結構，但亦可適宜製成積層結構。於陽極2為積層結構的情況下，亦可於第一層的陽極上積層不同的導電材料。The anode 2 is usually a single-layer structure, but it can also be suitably made into a laminated structure. In the case that the anode 2 has a laminated structure, different conductive materials can also be laminated on the anode of the first layer.

陽極2的厚度只要根據所需要的透明性與材質等來決定即可。特別是於需要高的透明性的情況下，較佳為可見光的透過率成為60%以上的厚度，進而佳為可見光的透過率成為80%以上的厚度。於該情況下，陽極2的厚度通常為5 nm以上，較佳為10 nm以上，且通常為1000 nm以下，較佳為500 nm以下。於不需要透明性的情況下，陽極2的厚度只要根據所需的強度等設為任意的厚度即可。於該情況下，陽極2可與基板為相同的厚度。The thickness of the anode 2 may be determined according to required transparency, material, and the like. In particular, when high transparency is required, the thickness is preferably such that the visible light transmittance is 60% or more, and more preferably the visible light transmittance is 80% or more. In this case, the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less. When transparency is not required, the thickness of the anode 2 may be any thickness according to required strength and the like. In this case, the anode 2 may have the same thickness as the substrate.

於在陽極2的表面對其他層進行成膜的情況下，較佳為於成膜前實施紫外線/臭氧、氧電漿、氬電漿等處理，藉此去除陽極2上的雜質，並且調整其游離電位而使電洞注入性提高。In the case of forming other layers on the surface of the anode 2, it is preferable to perform treatment such as ultraviolet light/ozone, oxygen plasma, and argon plasma before the film formation, thereby removing impurities on the anode 2 and adjusting its The free potential improves hole injection.

＜電洞注入層＞承擔自陽極2側向發光層5側傳輸電洞的功能的層通常被稱為電洞注入傳輸層或電洞傳輸層。於承擔自陽極2側向發光層5側傳輸電洞的功能的層存在兩層以上的情況下，有時將更靠近陽極2側的層稱為電洞注入層3。就強化自陽極2側向發光層5側傳輸電洞的功能的方面而言，較佳為形成電洞注入層3。於形成電洞注入層3的情況下，通常電洞注入層3形成於陽極2上。＜Hole injection layer＞ The layer that assumes the function of transporting holes from the anode 2 side to the light emitting layer 5 side is generally called a hole injection transport layer or a hole transport layer. When there are two or more layers that perform the function of transporting holes from the anode 2 side to the light emitting layer 5 side, the layer closer to the anode 2 side may be referred to as a hole injection layer 3 . From the viewpoint of enhancing the function of transporting holes from the anode 2 side to the light emitting layer 5 side, it is preferable to form the hole injection layer 3 . In the case of forming the hole injection layer 3 , the hole injection layer 3 is usually formed on the anode 2 .

電洞注入層3的膜厚通常為1 nm以上，較佳為5 nm以上，且通常為1000 nm以下，較佳為500 nm以下。The film thickness of the hole injection layer 3 is usually not less than 1 nm, preferably not less than 5 nm, and usually not more than 1000 nm, preferably not more than 500 nm.

電洞注入層的形成方法可為真空蒸鍍法，亦可為濕式成膜法。就成膜性優異的方面而言，較佳為藉由濕式成膜法來形成。The method for forming the hole injection layer may be a vacuum evaporation method or a wet film forming method. It is preferably formed by a wet film-forming method in terms of excellent film-forming properties.

以下，對一般的電洞注入層的形成方法進行說明。於本發明的有機電場發光元件中，電洞注入層3較佳為使用以下的電洞注入層形成用組成物並藉由濕式成膜法來形成。Hereinafter, a general method of forming a hole injection layer will be described. In the organic electroluminescence device of the present invention, the hole injection layer 3 is preferably formed by a wet film-forming method using the following composition for forming a hole injection layer.

電洞注入層形成用組成物通常包含形成電洞注入層3的電洞注入層用電洞傳輸性化合物。於濕式成膜法的情況下，電洞注入層形成用組成物通常亦更包含有機溶劑。電洞注入層形成用組成物較佳為電洞傳輸性高，可效率良好地傳輸經注入的電洞者。因此，較佳為電洞遷移率大，製造時或使用時等不易產生會成為陷阱的雜質。另外，較佳為穩定性優異、游離電位小、對可見光的透明性高。特別是於電洞注入層與發光層相接的情況下，較佳為不對來自發光層的發光進行消光者或與發光層形成激發錯合體（exciplex）而不會使發光效率降低者。The composition for forming a hole injection layer generally contains a hole transporting compound for a hole injection layer that forms the hole injection layer 3 . In the case of a wet film-forming method, the composition for forming the hole injection layer usually further includes an organic solvent. The composition for forming the hole injection layer is preferably one that has high hole transport properties and can efficiently transport injected holes. Therefore, it is preferable that the hole mobility is high, and impurities that become traps are less likely to be generated during manufacture or use. In addition, it is preferable that it is excellent in stability, has a small free potential, and has high transparency to visible light. Especially when the hole injection layer is in contact with the light-emitting layer, it is preferable not to quench light from the light-emitting layer or to form an exciplex with the light-emitting layer so as not to lower the light-emitting efficiency.

作為電洞注入層用電洞傳輸性化合物，就自陽極向電洞注入層的電荷注入障壁的觀點而言，較佳為具有4.5 eV～6.0 eV的游離電位的化合物。作為此種電洞傳輸性化合物的例子，可列舉：芳香族胺系化合物、酞菁系化合物、卟啉系化合物、寡聚噻吩系化合物、聚噻吩系化合物、苄基苯基系化合物、以芴基將三級胺連結而成的化合物、腙系化合物、矽氮烷系化合物、喹吖啶酮系化合物等。The hole transporting compound for the hole injection layer is preferably a compound having a free potential of 4.5 eV to 6.0 eV from the viewpoint of the charge injection barrier from the anode to the hole injection layer. Examples of such hole transporting compounds include: aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, fluorene compounds, Compounds formed by linking tertiary amines, hydrazone-based compounds, silazane-based compounds, quinacridone-based compounds, etc.

所述例示化合物中，就非晶質性及可見光透過性的方面而言，較佳為芳香族胺化合物，特佳為芳香族三級胺化合物。此處，所謂芳香族三級胺化合物，亦包含具有芳香族三級胺結構的化合物、即具有源自芳香族三級胺的基的化合物。Among the exemplified compounds, aromatic amine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred in terms of amorphous properties and visible light transmittance. Here, the aromatic tertiary amine compound also includes a compound having an aromatic tertiary amine structure, that is, a compound having a group derived from an aromatic tertiary amine.

芳香族三級胺化合物的種類並無特別限制，就藉由表面平滑化效果而容易獲得均勻的發光的方面而言，較佳為使用重量平均分子量為1000以上且1000000以下的高分子化合物（重複單元相連的聚合型化合物）。The type of aromatic tertiary amine compound is not particularly limited, and it is preferable to use a polymer compound having a weight average molecular weight of 1,000 or more and 1,000,000 or less (repeated A polymeric compound in which units are connected).

於藉由濕式成膜法來形成電洞注入層3的情況下，通常將形成電洞注入層3的材料與可溶解形成電洞注入層3的材料的有機溶劑（電洞注入層用溶劑）混合來製備成膜用的組成物（電洞注入層形成用組成物）。將該電洞注入層形成用組成物塗佈於相當於電洞注入層3的下層的層（通常為陽極2）上進行成膜，並使其乾燥，藉此形成電洞注入層3。In the case of forming the hole injection layer 3 by a wet film-forming method, the material forming the hole injection layer 3 and an organic solvent capable of dissolving the material forming the hole injection layer 3 (solvent for the hole injection layer ) were mixed to prepare a composition for film formation (a composition for forming a hole injection layer). The composition for forming a hole injection layer is applied to a layer corresponding to a lower layer of the hole injection layer 3 (usually the anode 2 ), formed into a film, and dried to form the hole injection layer 3 .

只要不明顯損害本發明的效果，則電洞注入層形成用組成物中的電洞傳輸性化合物的濃度為任意，就膜厚的均勻性的方面而言，較佳為低，就電洞注入層3中不易產生缺陷的方面而言，較佳為高。具體而言，較佳為0.01質量%以上，進而佳為0.1質量%以上，特佳為0.5質量%以上，另一方面，較佳為70質量%以下，進而佳為60質量%以下，特佳為50質量%以下。The concentration of the hole transport compound in the composition for forming a hole injection layer is arbitrary as long as the effect of the present invention is not significantly impaired, but it is preferably low in terms of uniformity of film thickness. Higher is preferable at the point that a defect is less likely to occur in the layer 3 . Specifically, it is preferably at least 0.01% by mass, more preferably at least 0.1% by mass, particularly preferably at least 0.5% by mass, on the other hand, preferably at most 70% by mass, further preferably at most 60% by mass, and most preferably at most 0.5% by mass. 50% by mass or less.

作為有機溶劑，例如可列舉醚系溶劑、酯系溶劑、芳香族烴系溶劑、醯胺系溶劑等。Examples of the organic solvent include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, amide-based solvents, and the like.

作為醚系溶劑，例如可列舉：乙二醇二甲醚、乙二醇二***、丙二醇-1-單甲醚乙酸酯（PGMEA）等脂肪族醚及1,2-二甲氧基苯、1,3-二甲氧基苯、苯甲醚、苯***、2-甲氧基甲苯、3-甲氧基甲苯、4-甲氧基甲苯、2,3-二甲基苯甲醚、2,4-二甲基苯甲醚等芳香族醚等。Examples of ether solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2 , 4-dimethylanisole and other aromatic ethers.

作為酯系溶劑，例如可列舉：乙酸苯酯、丙酸苯酯、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸正丁酯等芳香族酯等。Examples of the ester-based solvent include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.

作為芳香族烴系溶劑，例如可列舉：甲苯、二甲苯、環己基苯、3-異丙基聯苯、1,2,3,4-四甲基苯、1,4-二異丙基苯、環己基苯、甲基萘等。Examples of aromatic hydrocarbon solvents include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, and 1,4-diisopropylbenzene , cyclohexylbenzene, methylnaphthalene, etc.

作為醯胺系溶劑，例如可列舉N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等。Examples of the amide-based solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and the like.

除了可使用該些以外，亦可使用二甲基亞碸等。Other than these, dimethylsulfoxide and the like can also be used.

電洞注入層3的利用濕式成膜法的形成通常是藉由在製備電洞注入層形成用組成物後，將其塗佈成膜至相當於電洞注入層3的下層的層（通常為陽極2）上並進行乾燥來進行。The formation of the hole injection layer 3 by a wet film-forming method is usually performed by applying the composition for forming the hole injection layer to a layer corresponding to the lower layer of the hole injection layer 3 (usually for the anode 2) and carry out drying.

電洞注入層3通常是於成膜後藉由加熱或減壓乾燥等來使塗佈膜乾燥。The hole injection layer 3 is usually dried by heating or drying under reduced pressure after film formation.

於藉由真空蒸鍍法形成電洞注入層3的情況下，通常將電洞注入層3的構成材料的一種或兩種以上放入至設置於真空容器內的坩堝中（於使用兩種以上的材料的情況下，通常分別放入至不同的坩堝中），利用真空泵將真空容器內排氣至10 ^-4Pa左右。之後，對坩堝進行加熱（於使用兩種以上的材料的情況下，通常對各自的坩堝進行加熱），一邊控制坩堝內的材料的蒸發量一邊使其蒸發（於使用兩種以上的材料的情況下，通常分別獨立地一邊控制蒸發量一邊使其蒸發），於面向坩堝放置的基板1上的陽極2上形成電洞注入層3。於使用兩種以上的材料的情況下，亦可將該些的混合物放入至坩堝中，加熱使其蒸發來形成電洞注入層3。 In the case of forming the hole injection layer 3 by a vacuum evaporation method, usually one or more than two kinds of constituent materials of the hole injection layer 3 are put into a crucible provided in a vacuum vessel (when using two or more In the case of different materials, they are usually placed in different crucibles), and the inside of the vacuum container is evacuated to about 10 ^-4 Pa with a vacuum pump. Afterwards, the crucible is heated (in the case of using two or more materials, each crucible is usually heated), and the evaporation amount of the material in the crucible is controlled while evaporating it (in the case of using two or more materials) Next, the holes are formed on the anode 2 on the substrate 1 placed facing the crucible, and the hole injection layer 3 is formed on the anode 2 on the substrate 1 placed facing the crucible. When two or more materials are used, the mixture of these materials may be put into a crucible, heated and evaporated to form the hole injection layer 3 .

只要不明顯損害本發明的效果，則蒸鍍時的真空度並無限定，通常為0.1×10 ^-6Torr（0.13×10 ^-4Pa）以上且9.0×10 ^-6Torr（12.0×10 ^-4Pa）以下。只要不明顯損害本發明的效果，則蒸鍍速度並無限定，通常為0.1 Å/秒以上且5.0 Å/秒以下。只要不明顯損害本發明的效果，則蒸鍍時的成膜溫度並無限定，較佳為10℃以上且50℃以下。 The degree of vacuum during vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, and it is usually 0.1×10 ^-6 Torr (0.13×10 ^-4 Pa) or more and 9.0×10 ^-6 Torr (12.0×10 ^-4 Pa) below. The vapor deposition rate is not limited as long as the effect of the present invention is not significantly impaired, but is usually not less than 0.1 Å/sec and not more than 5.0 Å/sec. The film formation temperature at the time of vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is preferably 10° C. or higher and 50° C. or lower.

電洞注入層3亦可與後述的電洞傳輸層4同樣地交聯。The hole injection layer 3 may also be crosslinked in the same manner as the hole transport layer 4 described later.

＜電洞傳輸層＞電洞傳輸層4是承擔自陽極2側向發光層5側傳輸電洞的功能的層。電洞傳輸層4對於本發明的有機電場發光元件而言並不是必需的層，但就強化自陽極2向發光層5傳輸電洞的功能的方面而言，較佳為形成該層。於形成電洞傳輸層4的情況下，通常電洞傳輸層4形成於陽極2與發光層5之間。於存在所述電洞注入層3的情況下，電洞傳輸層4形成於電洞注入層3與發光層5之間。＜Hole Transport Layer＞ The hole transport layer 4 is a layer that functions to transport holes from the anode 2 side to the light emitting layer 5 side. The hole transport layer 4 is not an essential layer for the organic electroluminescent device of the present invention, but it is preferably formed in terms of enhancing the function of transporting holes from the anode 2 to the light emitting layer 5 . In the case of forming the hole transport layer 4 , usually the hole transport layer 4 is formed between the anode 2 and the light emitting layer 5 . In the presence of the hole injection layer 3 , the hole transport layer 4 is formed between the hole injection layer 3 and the light emitting layer 5 .

作為形成電洞傳輸層4的材料，較佳為電洞傳輸性高且可效率良好地傳輸經注入的電洞的材料。因此，較佳為游離電位小、相對於可見光的光而言透明性高、電洞遷移率大、穩定性優異、製造時或使用時不易產生會成為陷阱的雜質。另外，於大多數情況下，電洞傳輸層4與發光層5相接，因此較佳為不會對來自發光層5的發光進行消光或不會與發光層5之間形成激發錯合體（exciplex）而使效率降低。As a material for forming the hole transport layer 4 , a material having a high hole transport property and capable of efficiently transporting injected holes is preferable. Therefore, it is preferable that the free potential is small, the transparency to visible light is high, the hole mobility is large, the stability is excellent, and impurities that become traps are less likely to be generated during production or use. In addition, in most cases, the hole transport layer 4 is in contact with the light-emitting layer 5, so it is preferable not to quench the light emitted from the light-emitting layer 5 or to form an exciplex with the light-emitting layer 5. ) to reduce the efficiency.

作為此種電洞傳輸層4的材料，只要為先前作為電洞傳輸層的構成材料來使用的材料即可，例如可列舉作為所述電洞注入層3中所使用的電洞傳輸性化合物而例示者。另外，可列舉：芳基胺衍生物、芴衍生物、螺環衍生物、咔唑衍生物、吡啶衍生物、吡嗪衍生物、嘧啶衍生物、三嗪衍生物、喹啉衍生物、啡啉衍生物、酞菁衍生物、卟啉衍生物、噻咯（silole）衍生物、寡聚噻吩衍生物、縮合多環芳香族衍生物、金屬錯合物等。The material of the hole transport layer 4 may be any material that has been previously used as a constituent material of the hole transport layer. For example, the hole transport compound used in the hole injection layer 3 may be mentioned. instantiater. In addition, arylamine derivatives, fluorene derivatives, spiro derivatives, carbazole derivatives, pyridine derivatives, pyrazine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, phenanthroline Derivatives, phthalocyanine derivatives, porphyrin derivatives, silole derivatives, oligothiophene derivatives, condensed polycyclic aromatic derivatives, metal complexes, etc.

作為電洞傳輸層4的材料，另外例如可列舉：聚乙烯基咔唑衍生物、聚芳基胺衍生物、聚乙烯基三苯基胺衍生物、聚芴衍生物、聚伸芳基衍生物、含有四苯基聯苯胺的聚伸芳基醚碸衍生物、聚伸芳基伸乙烯衍生物、聚矽氧烷衍生物、聚噻吩衍生物、聚(對苯乙炔)衍生物等。該些可為交替共聚物、無規聚合體、嵌段聚合體或接枝共聚物的任一者。另外，亦可為於主鏈具有分枝且末端部存在三個以上的高分子、或所謂的樹枝狀聚合物（dendrimer）。As the material of the hole transport layer 4, other examples include: polyvinylcarbazole derivatives, polyarylamine derivatives, polyvinyltriphenylamine derivatives, polyfluorene derivatives, polyarylene derivatives , polyaryl ether derivatives containing tetraphenylbenzidine, polyaryl vinylene derivatives, polysiloxane derivatives, polythiophene derivatives, poly(p-phenylene vinylene) derivatives, etc. These may be any of alternating copolymers, random polymers, block polymers, or graft copolymers. In addition, a polymer having branches in the main chain and three or more terminals present, or a so-called dendrimer may also be used.

其中，較佳為聚芳基胺衍生物或聚伸芳基衍生物。作為聚芳基胺衍生物，較佳為包含下述式（II）所表示的重複單元的聚合體。特佳為由下述式（II）所表示的重複單元組成的聚合體，於該情況下，於各重複單元中，Ar ^a或Ar ^b可不同。 Among them, polyarylamine derivatives or polyarylylene derivatives are preferred. As the polyarylamine derivative, a polymer containing a repeating unit represented by the following formula (II) is preferable. Particularly preferred is a polymer composed of repeating units represented by the following formula (II). In this case, Ar ^a or Ar ^b may be different in each repeating unit.

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（式（II）中，Ar ^a及Ar ^b分別獨立地表示可具有取代基的芳香族烴基或可具有取代基的芳香族雜環基。） (In formula (II), Ar ^a and Ar ^b each independently represent an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.)

作為聚伸芳基衍生物，可列舉於其重複單元中具有可具有取代基的芳香族烴基或可具有取代基的芳香族雜環基等伸芳基的聚合體。Examples of the polyarylene derivative include a polymer having an arylylene group such as an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent in its repeating unit.

作為聚伸芳基衍生物，較佳為具有包含下述式（III-1）及/或下述式（III-2）的重複單元的聚合體。The polyarylene derivative is preferably a polymer having a repeating unit of the following formula (III-1) and/or the following formula (III-2).

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（式（III-1）中，R ^a、R ^b、R ^c及R ^d分別獨立地表示烷基、烷氧基、苯基烷基、苯基烷氧基、苯基、苯氧基、烷基苯基、烷氧基苯基、烷基羰基、烷氧基羰基或羧基。t及s分別獨立地表示0～3的整數。於t或s為2以上的情況下，包含於一分子中的多個R ^a或R ^b可相同亦可不同，鄰接的R ^a或R ^b彼此可形成環。） (In formula (III-1), R ^a , R ^b , R ^c and R ^d independently represent alkyl, alkoxy, phenylalkyl, phenylalkoxy, phenyl, phenoxy, alkane phenyl, alkoxyphenyl, alkylcarbonyl, alkoxycarbonyl or carboxyl. t and s each independently represent an integer of 0 to 3. When t or s is 2 or more, it is contained in one molecule A plurality of R ^a or R ^b may be the same or different, and adjacent R ^a or R ^b may form a ring with each other.)

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（式（III-2）中，R ^e及R ^f分別獨立地與所述式（III-1）中的R ^a、R ^b、R ^c或R ^d為相同含義。r及u分別獨立地表示0～3的整數。於r或u為2以上的情況下，一分子中包含的多個R ^e及R ^f可相同亦可不同，鄰接的R ^e或R ^f彼此可形成環。X表示構成5員環或6員環的原子或原子群組。） (In formula (III-2), R ^e and R ^f independently have the same meaning as R ^a , R ^b , R ^c or R ^d in formula (III-1). r and u independently represent An integer of 0 to 3. When r or u is 2 or more, a plurality of R ^e and R ^f contained in one molecule may be the same or different, and adjacent R ^e or R ^f may form a ring with each other. X represents the composition An atom or group of atoms of a 5-membered or 6-membered ring.)

作為X的具體例，為氧原子、可具有取代基的硼原子、可具有取代基的氮原子、可具有取代基的矽原子、可具有取代基的磷原子、可具有取代基的硫原子、可具有取代基的碳原子或者該些鍵結而成的基。Specific examples of X include an oxygen atom, a boron atom that may have a substituent, a nitrogen atom that may have a substituent, a silicon atom that may have a substituent, a phosphorus atom that may have a substituent, a sulfur atom that may have a substituent, A carbon atom which may have a substituent or a group formed by these bonds.

作為聚伸芳基衍生物，較佳為除了具有包含所述式（III-1）及/或所述式（III-2）的重複單元以外，更具有下述式（III-3）所表示的重複單元。As a polyarylene derivative, it is preferred to have the following formula (III-3) in addition to the repeating unit comprising the formula (III-1) and/or the formula (III-2): repeating unit.

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（式（III-3）中，Ar ^c～Ar ⁱ分別獨立地表示可具有取代基的芳香族烴基或可具有取代基的芳香族雜環基。V及w分別獨立地表示0或1。） (In formula (III-3), Ar ^c to Ar ⁱ each independently represent an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group. V and w each independently represent 0 or 1.)

所述式（III-1）～式（III-3）的具體例及聚伸芳基衍生物的具體例等可列舉日本專利特開2008-98619號公報中記載的具體例等。Specific examples of the formula (III-1) to formula (III-3) and specific examples of the polyarylene derivative include those described in JP-A-2008-98619.

於利用濕式成膜法形成電洞傳輸層4的情況下，與所述電洞注入層3的形成同樣地，製備電洞傳輸層形成用組成物後，於濕式成膜後進行加熱乾燥。In the case of forming the hole transport layer 4 by a wet film formation method, in the same manner as the formation of the hole injection layer 3, after preparing a composition for forming a hole transport layer, heat and dry after wet film formation .

電洞傳輸層形成用組成物除了含有所述電洞傳輸性化合物以外，亦含有有機溶劑。所使用的有機溶劑與所述電洞注入層形成用組成物中使用的有機溶劑相同。成膜條件、加熱乾燥條件等亦與電洞注入層3的形成的情況相同。The composition for forming a hole transport layer contains an organic solvent in addition to the above-mentioned hole transport compound. The organic solvent used is the same as that used in the above-mentioned composition for forming a hole injection layer. Film-forming conditions, heating and drying conditions, and the like are also the same as in the case of forming the hole injection layer 3 .

於利用真空蒸鍍法形成電洞傳輸層4的情況下，其成膜條件等亦與所述電洞注入層3的形成的情況相同。In the case of forming the hole transport layer 4 by the vacuum evaporation method, the film formation conditions and the like are the same as those for the formation of the hole injection layer 3 described above.

電洞傳輸層4除了含有所述電洞傳輸性化合物以外，亦可含有各種發光材料、電子傳輸性化合物、黏合劑樹脂、塗佈性改良劑等。因此，電洞傳輸層形成用組成物除了含有所述電洞傳輸性化合物以外，亦可含有各種發光材料、電子傳輸性化合物、黏合劑樹脂、塗佈性改良劑等。The hole transport layer 4 may contain various light-emitting materials, electron transport compounds, binder resins, coatability improvers, and the like in addition to the hole transport compound described above. Therefore, the composition for forming a hole transport layer may contain various light-emitting materials, electron transport compounds, binder resins, coatability improvers, and the like in addition to the hole transport compound described above.

電洞傳輸層4亦可為將交聯性化合物交聯而形成的層。交聯性化合物是具有交聯性基的化合物，藉由進行交聯而形成網眼狀高分子化合物。The hole transport layer 4 may be a layer formed by crosslinking a crosslinkable compound. The crosslinkable compound is a compound having a crosslinkable group, and forms a network polymer compound by crosslinking.

若列舉該交聯性基的例子，則可列舉源自氧雜環丁烷、環氧等環狀醚的基；源自乙烯基、三氟乙烯基、苯乙烯基、丙烯酸基、甲基丙烯醯基、肉桂醯基等不飽和雙鍵的基；源自苯並環丁烯的基等。Examples of the crosslinkable group include groups derived from cyclic ethers such as oxetane and epoxy; groups derived from vinyl, trifluorovinyl, styrene, acrylic, and methacrylic groups; Unsaturated double bond group such as acyl group and cinnamyl group; group derived from benzocyclobutene, etc.

交聯性化合物可為單體、寡聚物、聚合物的任一種。交聯性化合物可僅具有一種，亦可以任意的組合及比率具有兩種以上。The crosslinkable compound may be any of monomers, oligomers, and polymers. There may be only one type of crosslinkable compound, or two or more types may be used in arbitrary combinations and ratios.

作為交聯性化合物，較佳為使用具有交聯性基的電洞傳輸性化合物。作為具有交聯性基的電洞傳輸性化合物的電洞傳輸性化合物，可列舉所述例示的化合物，作為交聯性化合物，可列舉相對於該些電洞傳輸性化合物而交聯性基鍵結於主鏈或側鏈的化合物。特佳為交聯性基經由伸烷基等連結基而鍵結於主鏈。另外，特別是作為電洞傳輸性化合物，較佳為包含具有交聯性基的重複單元的聚合體，更佳為具有交聯性基直接或經由連結基鍵結於所述式（II）或式（III-1）～式（III-3）所表示的重複單元上的重複單元的聚合體。 As the crosslinkable compound, it is preferable to use a hole transport compound having a crosslinkable group. The hole-transporting compound as the hole-transporting compound having a cross-linking group includes the above-mentioned exemplified compounds, and the cross-linking compound includes a compound having a cross-linking group bond with respect to these hole-transporting compounds. Compounds attached to the main chain or side chains. Particularly preferably, the crosslinkable group is bonded to the main chain via a linking group such as an alkylene group. In addition, especially as a hole-transporting compound, it is preferably a polymer comprising a repeating unit having a cross-linking group, more preferably a polymer having a cross-linking group bonded directly or via a linking group to the formula (II) or A polymer of repeating units on the repeating units represented by formula (III-1) to formula (III-3).

於將交聯性化合物交聯而形成電洞傳輸層4時，通常製備將交聯性化合物溶解或分散於有機溶劑中而成的電洞傳輸層形成用組成物，並利用濕式成膜法進行成膜並使其交聯。When forming the hole transport layer 4 by cross-linking the cross-linkable compound, a composition for forming the hole transport layer in which the cross-linkable compound is dissolved or dispersed in an organic solvent is usually prepared, and a wet film-forming method is used Film formation and crosslinking are performed.

電洞傳輸層4的膜厚通常為5 nm以上，較佳為10 nm以上，且通常為300 nm以下，較佳為100 nm以下。The film thickness of the hole transport layer 4 is usually not less than 5 nm, preferably not less than 10 nm, and usually not more than 300 nm, preferably not more than 100 nm.

＜發光層＞發光層5是承擔於一對電極間被賦予電場時，藉由自陽極2注入的電洞與自陰極7注入的電子再結合而被激發，從而發光的功能的層。發光層5是形成於陽極2與陰極7之間的層。於在陽極2上存在電洞注入層3的情況下，發光層5形成於電洞注入層3與陰極7之間。於在陽極2上存在電洞傳輸層4的情況下，發光層5形成於電洞傳輸層4與陰極7之間。＜Light emitting layer＞ The light-emitting layer 5 is a layer that functions to emit light by being excited by the recombination of holes injected from the anode 2 and electrons injected from the cathode 7 when an electric field is applied between a pair of electrodes. The light emitting layer 5 is a layer formed between the anode 2 and the cathode 7 . In the case where the hole injection layer 3 is present on the anode 2 , the light emitting layer 5 is formed between the hole injection layer 3 and the cathode 7 . In the case where the hole transport layer 4 is present on the anode 2 , the light emitting layer 5 is formed between the hole transport layer 4 and the cathode 7 .

發光層5至少含有具有發光性質的材料（發光材料），並且較佳為含有一種或多種主體材料。如所述般，本發明中的有機電場發光元件的發光層5由本發明的組成物並藉由濕式成膜法來形成。使用本發明的組成物而形成的發光層較佳為包含本發明的芳香族化合物、磷光發光材料及電荷傳輸材料，包含所述式（250）所表示的化合物及/或所述式（240）所表示的化合物作為所述電荷傳輸材料。 The light-emitting layer 5 contains at least a material with light-emitting properties (luminescent material), and preferably contains one or more host materials. As mentioned above, the light-emitting layer 5 of the organic electroluminescence device in the present invention is formed from the composition of the present invention by a wet film-forming method. The light-emitting layer formed using the composition of the present invention preferably contains the aromatic compound, phosphorescent light-emitting material and charge transport material of the present invention, including the compound represented by the formula (250) and/or the formula (240) The indicated compounds serve as the charge transport material.

只要不明顯損害本發明的效果，則發光層5的膜厚為任意，但就膜不易產生缺陷的方面而言較佳為厚，另一方面，就容易形成低驅動電壓的方面而言較佳為薄。發光層5的膜厚較佳為3 nm以上，更佳為5 nm以上，另一方面，較佳為200 nm以下，更佳為100 nm以下。The film thickness of the light-emitting layer 5 is arbitrary as long as the effect of the present invention is not significantly impaired, but it is preferably thicker in terms of less likely to cause defects in the film, and on the other hand, it is preferred in terms of easy formation of a low driving voltage. as thin. The film thickness of the light-emitting layer 5 is preferably at least 3 nm, more preferably at least 5 nm, and on the other hand, preferably at most 200 nm, more preferably at most 100 nm.

＜電洞阻擋層＞亦可於發光層5與後述的電子注入層6之間設置電洞阻擋層。電洞阻擋層是於發光層5上以與發光層5的陰極7側的界面相接的方式積層的層。＜Hole blocking layer＞ A hole blocking layer may also be provided between the light emitting layer 5 and the electron injection layer 6 described later. The hole blocking layer is a layer laminated on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 7 side.

電洞阻擋層具有阻止自陽極2移動而來的電洞到達陰極7的作用及將自陰極7注入的電子效率良好地向發光層5的方向傳輸的作用。作為對構成電洞阻擋層的材料所要求的物性，可列舉電子遷移率高且電洞遷移率低、能隙（HOMO、LUMO之差）大、激發三重態能階（T ₁）高。 The hole blocking layer has a function of preventing holes moving from the anode 2 from reaching the cathode 7 and a function of efficiently transporting electrons injected from the cathode 7 toward the light emitting layer 5 . The physical properties required for the material constituting the hole blocking layer include high electron mobility, low hole mobility, large energy gap (difference between HOMO and LUMO), and high excited triplet energy level (T ₁ ).

作為滿足此種條件的電洞阻擋層的材料，例如可列舉：雙(2-甲基-8-羥基喹啉)(苯酚)鋁、雙(2-甲基-8-羥基喹啉)(三苯基矽醇)鋁等混合配位體錯合物、雙(2-甲基-8-キノラト)鋁-μ-氧代-雙-(2-甲基-8-キノリラト)鋁二核金屬錯合物等金屬錯合物、二苯乙烯基聯苯衍生物等苯乙烯基化合物（日本專利特開平11-242996號公報）、3-(4-聯苯基)-4-苯基-5-(4-第三丁基苯基)-1,2,4-***等***衍生物（日本專利特開平7-41759號公報）、浴銅靈（bathocuproin）等啡啉衍生物（日本專利特開平10-79297號公報）等。進而，國際公開第2005/022962號中記載的具有至少一個2,4,6位經取代的吡啶環的化合物亦較佳地作為電洞阻擋層的材料。As the material of the hole blocking layer satisfying this condition, for example, bis(2-methyl-8-hydroxyquinoline) (phenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (tri Mixed ligand complexes such as phenylsilanol) aluminum, bis(2-methyl-8-kinolilat)aluminum-μ-oxo-bis-(2-methyl-8-kinolilat)aluminum dinuclear metal complexes Metal complexes such as metal complexes, styryl compounds such as distyryl biphenyl derivatives (Japanese Patent Laid-Open No. 11-242996), 3-(4-biphenyl)-4-phenyl-5- Triazole derivatives such as (4-tert-butylphenyl)-1,2,4-triazole (Japanese Patent Laid-Open Publication No. 7-41759), phenanthroline derivatives such as bathocuproin (Japanese Patent Japanese Patent Application Publication No. 10-79297), etc. Furthermore, compounds having at least one pyridine ring substituted at positions 2, 4, and 6 described in International Publication No. 2005/022962 are also preferably used as materials for the hole blocking layer.

電洞阻擋層的形成方法並無限制。因此，可利用濕式成膜法、蒸鍍法、或其他方法來形成。The method of forming the hole blocking layer is not limited. Therefore, it can be formed by a wet film-forming method, a vapor deposition method, or other methods.

只要不明顯損害本發明的效果，則電洞阻擋層的膜厚為任意，通常為0.3 nm以上，較佳為0.5 nm以上，且通常為100 nm以下，較佳為50 nm以下。As long as the effect of the present invention is not significantly impaired, the film thickness of the hole blocking layer is arbitrary, usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less.

＜電子傳輸層＞為了進一步提高元件的電流效率，電子傳輸層6設置於發光層5與陰極7之間。＜Electron transport layer＞ In order to further improve the current efficiency of the device, the electron transport layer 6 is disposed between the light emitting layer 5 and the cathode 7 .

電子傳輸層6由可於被賦予電場的電極間將自陰極7注入的電子效率良好地傳輸至發光層5的方向的化合物形成。作為電子傳輸層6中所使用的電子傳輸性化合物，需要為自陰極7的電子注入效率高、且具有高的電子遷移率，可效率良好地傳輸經注入的電子的化合物。The electron transport layer 6 is formed of a compound capable of efficiently transporting electrons injected from the cathode 7 to the light emitting layer 5 between electrodes to which an electric field is applied. The electron-transporting compound used in the electron-transporting layer 6 needs to be a compound that has high electron injection efficiency from the cathode 7 , has high electron mobility, and can efficiently transport the injected electrons.

作為電子傳輸層6中使用的電子傳輸性化合物，具體而言，可列舉：8-羥基喹啉的鋁錯合物等金屬錯合物（日本專利特開昭59-194393號公報）、10-羥基苯並[h]喹啉的金屬錯合物、噁二唑衍生物、二苯乙烯基聯苯衍生物、噻咯衍生物、3-羥基黃酮金屬錯合物、5-羥基黃酮金屬錯合物、苯並噁唑金屬錯合物、苯並噻唑金屬錯合物、三苯並咪唑基苯（美國專利第5645948號說明書）、喹噁啉化合物（日本專利特開平6-207169號公報）、啡啉衍生物（日本專利特開平5-331459號公報）、2-第三丁基-9,10-N,N'-二氰基蒽醌二亞胺、n型氫化非晶質碳化矽、n型硫化鋅、n型硒化鋅等。As the electron-transporting compound used in the electron-transporting layer 6, specifically, metal complexes such as aluminum complexes of 8-hydroxyquinoline (Japanese Patent Laid-Open No. 59-194393 ), 10- Metal complexes of hydroxybenzo[h]quinoline, oxadiazole derivatives, distyryl biphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes compounds, benzoxazole metal complexes, benzothiazole metal complexes, tribenzimidazolylbenzene (US Patent No. 5645948 specification), quinoxaline compounds (Japanese Patent Laid-Open Publication No. 6-207169), Phenanthroline derivatives (Japanese Patent Laid-Open No. 5-331459), 2-tert-butyl-9,10-N,N'-dicyanoanthraquinone diimide, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type zinc selenide, etc.

電子傳輸層6藉由與所述同樣地利用濕式成膜法、或真空蒸鍍法積層於電洞阻擋層上來形成。通常使用真空蒸鍍法。於本發明中，如所述般，可利用濕式成膜法於包含本發明的化合物的發光層上形成電子傳輸層6。The electron transport layer 6 is formed by laminating on the hole blocking layer by the wet film-forming method or the vacuum evaporation method in the same manner as described above. Usually a vacuum evaporation method is used. In the present invention, as described above, the electron transport layer 6 can be formed on the light-emitting layer containing the compound of the present invention by a wet film-forming method.

電子傳輸層6的膜厚通常為1 nm以上，較佳為5 nm以上，且通常為300 nm以下，較佳為100 nm以下。The film thickness of the electron transport layer 6 is usually not less than 1 nm, preferably not less than 5 nm, and usually not more than 300 nm, preferably not more than 100 nm.

＜電子注入層＞為了將自陰極7注入的電子效率良好地注入至電子傳輸層6或發光層5，亦可於電子傳輸層6與陰極7之間設置電子注入層。＜Electron injection layer＞ In order to efficiently inject electrons injected from the cathode 7 into the electron transport layer 6 or the light emitting layer 5 , an electron injection layer may be provided between the electron transport layer 6 and the cathode 7 .

為了效率良好地進行電子注入，形成電子注入層的材料較佳為功函數低的金屬。作為例子，可使用鈉或銫等鹼金屬、鋇或鈣等鹼土金屬等。電子注入層的膜厚通常較佳為0.1 nm以上且5 nm以下。 In order to perform electron injection efficiently, the material forming the electron injection layer is preferably a metal with a low work function. As an example, an alkali metal such as sodium or cesium, an alkaline earth metal such as barium or calcium, or the like can be used. The film thickness of the electron injection layer is usually preferably not less than 0.1 nm and not more than 5 nm.

進而，對紅啡啉（bathophenanthroline）等含氮雜環化合物或8-羥基喹啉的鋁錯合物等金屬錯合物所代表的有機電子傳輸材料摻雜鈉、鉀、銫、鋰、銣等鹼金屬（記載於日本專利特開平10-270171號公報、日本專利特開2002-100478號公報、日本專利特開2002-100482號公報等中）時，亦能夠兼具電子注入性、傳輸性提高的優異的膜質，因此較佳。Furthermore, organic electron transport materials represented by nitrogen-containing heterocyclic compounds such as bathophenanthroline or metal complexes such as aluminum complexes of 8-hydroxyquinoline are doped with sodium, potassium, cesium, lithium, rubidium, etc. Alkali metals (described in Japanese Patent Laid-Open No. 10-270171, Japanese Patent Laid-Open No. 2002-100478, Japanese Patent Laid-Open No. 2002-100482, etc.) can also improve electron injection and transport properties Excellent film quality, so better.

電子注入層的膜厚通常為5 nm以上，較佳為10 nm以上，另外通常為200 nm以下，較佳為100 nm以下的範圍。The film thickness of the electron injection layer is usually not less than 5 nm, preferably not less than 10 nm, and is usually not more than 200 nm, preferably not more than 100 nm.

電子注入層藉由利用濕式成膜法或真空蒸鍍法，積層於發光層5或者其上的電洞阻擋層或電子傳輸層6上而形成。濕式成膜法時的詳細情況與所述發光層的情況相同。 The electron injection layer is formed by laminating on the light emitting layer 5 or the hole blocking layer or the electron transport layer 6 thereon by wet film forming method or vacuum evaporation method. The details of the wet film-forming method are the same as those of the light-emitting layer.

亦存在藉由電子傳輸材料與鋰錯合物共摻雜的操作將電洞阻擋層、電子傳輸層、電子注入層形成為一層的情況。There is also a case where the hole blocking layer, the electron transport layer, and the electron injection layer are formed into one layer by co-doping the electron transport material and the lithium complex.

＜陰極＞陰極7發揮將電子注入至發光層5側的層（電子注入層或發光層等）的作用。＜Cathode＞ The cathode 7 plays a role of injecting electrons into a layer (an electron injection layer or a light emitting layer, etc.) on the side of the light emitting layer 5 .

作為陰極7的材料，能夠使用於所述的陽極2中所使用的材料。為了效率良好地進行電子注入，作為陰極7的材料，較佳為使用功函數低的金屬，例如可使用錫、鎂、銦、鈣、鋁、銀等金屬或該些的合金等。作為具體例，例如可列舉：鎂-銀合金、鎂-銦合金、鋁-鋰合金等低功函數的合金電極等。As the material of the cathode 7, the material used for the above-mentioned anode 2 can be used. In order to inject electrons efficiently, it is preferable to use a metal with a low work function as the material of the cathode 7, for example, metals such as tin, magnesium, indium, calcium, aluminum, silver, or alloys of these metals can be used. Specific examples include alloy electrodes with low work functions such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys.

就有機電場發光元件的穩定性的方面而言，較佳為於陰極上積層功函數高、對於大氣而言穩定的金屬層，以保護包含低功函數的金屬的陰極。作為積層的金屬，例如可列舉：鋁、銀、銅、鎳、鉻、金、鉑等金屬。In terms of the stability of the organic electroluminescent device, it is preferable to laminate a metal layer having a high work function and stable to the atmosphere on the cathode to protect the cathode including a metal with a low work function. Examples of metals to be laminated include metals such as aluminum, silver, copper, nickel, chromium, gold, and platinum.

陰極的膜厚通常與陽極相同。The film thickness of the cathode is usually the same as that of the anode.

＜其他層＞只要不明顯損害本發明的效果，則本發明的有機電場發光元件亦可更具有其他層。即，亦可於陽極與陰極之間具有所述的其他任意層。＜Other layers＞ As long as the effects of the present invention are not significantly impaired, the organic electroluminescence device of the present invention may further have other layers. That is, any other layer described above may be provided between the anode and the cathode.

＜其他元件結構＞本發明的有機電場發光元件亦可為與所述說明相反的結構，即，例如亦能夠於基板上按照陰極、電子注入層、電子傳輸層、電洞阻擋層、發光層、電洞傳輸層、電洞注入層、陽極的順序進行積層。＜Other component structure＞ The organic electroluminescent element of the present invention can also be the structure opposite to the above description, that is, for example, a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light emitting layer, a hole transport layer, The hole injection layer and the anode are laminated in this order.

於將本發明的有機電場發光元件適用於有機電場發光裝置的情況下，可用作單一的有機電場發光元件，可製成將多個有機電場發光元件呈陣列狀配置的結構來使用，亦可製成將陽極與陰極呈X-Y矩陣狀配置的結構來使用。When the organic electroluminescent element of the present invention is applied to an organic electroluminescent device, it can be used as a single organic electroluminescent element, or it can be used as a structure in which a plurality of organic electroluminescent elements are arranged in an array. It is used as a structure in which anodes and cathodes are arranged in an X-Y matrix.

[顯示裝置] 本發明的顯示裝置（有機電場發光元件顯示裝置：有機EL顯示裝置）包括本發明的有機電場發光元件。關於本發明的有機EL顯示裝置的型號或結構，並無特別限制，可使用本發明的有機電場發光元件並依照常規方法來進行組裝。 [display device] The display device (organic electroluminescent element display device: organic EL display device) of the present invention includes the organic electroluminescent element of the present invention. There is no particular limitation on the type or structure of the organic EL display device of the present invention, and the organic electroluminescence element of the present invention can be used to assemble according to conventional methods.

例如，可利用「有機EL顯示器」（歐姆社（Ohmsha），2004年8月20日發行，時任靜士、安達千波矢、村田英幸著）中所記載般的方法來形成本發明的有機EL顯示裝置。For example, the method described in "Organic EL Display" (Ohmsha, published on August 20, 2004, written by Seiji Adachi, Chihaya Adachi, and Hideyuki Murata) can be used to form the organic EL display of the present invention. device.

[照明裝置] 本發明的照明裝置（有機電場發光元件照明裝置：有機EL照明裝置）包括本發明的有機電場發光元件。關於本發明的有機EL照明裝置的型號或結構，並無特別限制，可使用本發明的有機電場發光元件並依照常規方法來進行組裝。 [lighting device] The lighting device (organic electroluminescent element lighting device: organic EL lighting device) of the present invention includes the organic electroluminescent device of the present invention. There is no particular limitation on the model or structure of the organic EL lighting device of the present invention, and the organic electroluminescent element of the present invention can be used to assemble according to conventional methods.

本發明的有機電場發光元件被用於有機EL顯示器等顯示裝置或有機EL照明等照明裝置。可藉由本發明的有機電場發光元件，例如利用「有機EL顯示器」（歐姆社（Ohmsha），2004年8月20日發行，時任靜士、安達千波矢、村田英幸著）中所記載般的方法來形成有機EL顯示器或有機EL照明。 [實施例] The organic electroluminescent device of the present invention is used in display devices such as organic EL displays and lighting devices such as organic EL lighting. The organic electroluminescent device of the present invention can be used, for example, by using the method described in "Organic EL Display" (Ohmsha, published on August 20, 2004, written by Seiji Adachi, Chiba Yasuda, and Hideyuki Murata at the time). To form an organic EL display or organic EL lighting. [Example]

以下，藉由實施例對本發明進行更詳細的說明。本發明只要不超過其主旨，則並不限定於以下的實施例。下述實施例中的各種條件或評價結果的值具有作為本發明的實施方式中的上限或下限的較佳的值的含義，較佳的範圍亦可為由所述上限或下限的值與下述實施例的值或實施例彼此的值的組合規定的範圍。 Hereinafter, the present invention will be described in more detail with examples. The present invention is not limited to the following examples unless the gist is exceeded. The values of various conditions or evaluation results in the following examples have the meaning of preferred values as the upper limit or lower limit in the embodiments of the present invention, and the preferred range can also be defined by the value of the upper limit or lower limit and the lower limit. The value of the above-described embodiment or the range specified by the combination of the values of the embodiments.

於本說明書中，Ac是指乙醯基，Ph是指苯基，dppf是指1,1'-雙(二苯基膦基)二茂鐵，DMSO是指二甲基亞碸。比較化合物1、比較化合物2依照所述專利文獻1（國際公開第2007/043357號）中記載的方法來合成。 In this specification, Ac means acetyl, Ph means phenyl, dppf means 1,1'-bis(diphenylphosphino)ferrocene, and DMSO means dimethylsulfoxide. Comparative Compound 1 and Comparative Compound 2 were synthesized according to the method described in Patent Document 1 (International Publication No. 2007/043357).

[合成實施例I-1：化合物（H-1）的合成例] ＜化合物1-c的合成＞ [化58]

[Synthesis Example I-1: Synthesis Example of Compound (H-1)] <Synthesis of Compound 1-c> [Chem. 58]

於氮環境下，於化合物1-a（14.1 g，30.4 mmol）、化合物1-b（7.23 g，20.3 mmol）中依次加入進行了氮起泡的甲苯（130 mL）、乙醇（30 mL）、磷酸三鉀水溶液（2.0 mol/L，30 mL），並加熱至60℃。之後，加入Pd(PPh ₃) ₄（0.23 g，0.20 mmol），於90℃下加熱攪拌3小時。冷卻至室溫後，加入飽和氯化鈉水溶液，並使用甲苯進行萃取。利用飽和氯化鈉水溶液清洗有機層，並利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物1-c（產量9.0 g，收率72%）。 Under nitrogen environment, to compound 1-a (14.1 g, 30.4 mmol) and compound 1-b (7.23 g, 20.3 mmol) were sequentially added toluene (130 mL), ethanol (30 mL), and Tripotassium phosphate aqueous solution (2.0 mol/L, 30 mL), and heated to 60°C. Thereafter, Pd(PPh ₃ ) ₄ (0.23 g, 0.20 mmol) was added, followed by heating and stirring at 90° C. for 3 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added, and extraction was performed using toluene. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound 1-c (yield 9.0 g, yield 72%).

（化合物（H-1）的合成） [化59]

(Synthesis of Compound (H-1)) [Chem. 59]

於氮環境下，於化合物1-c（2.0 g，3.26 mmol）、化合物1-d（0.66 g，1.63 mmol）中依次加入進行了氮起泡的甲苯（40 mL）、乙醇（20 mL）、磷酸三鉀水溶液（2.0 mol/L，20 mL），並加熱至60℃。之後，加入Pd(PPh ₃) ₄（0.23 g，0.20 mmol），於90℃下加熱攪拌5小時。冷卻至室溫後，加入飽和氯化鈉水溶液，並使用甲苯進行萃取。利用飽和氯化鈉水溶液清洗有機層，並利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物（H-1）（產量1.44 g，收率72%）。 Under a nitrogen environment, to compound 1-c (2.0 g, 3.26 mmol) and compound 1-d (0.66 g, 1.63 mmol) were sequentially added toluene (40 mL), ethanol (20 mL), and Tripotassium phosphate aqueous solution (2.0 mol/L, 20 mL), and heated to 60°C. Thereafter, Pd(PPh ₃ ) ₄ (0.23 g, 0.20 mmol) was added, followed by heating and stirring at 90° C. for 5 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added, and extraction was performed using toluene. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound (H-1) (yield: 1.44 g, yield: 72%).

[合成實施例I-2：化合物（H-2）的合成例] ＜化合物2-c的合成＞ [化60]

[Synthesis Example I-2: Synthesis Example of Compound (H-2)] <Synthesis of Compound 2-c> [Chem. 60]

於化合物2-a（10.6 g，26.1 mmol）、化合物2-b（16.2 g，57.4 mmol）中依次加入進行了氮起泡的甲苯（130 mL）、乙醇（65 mL）、磷酸三鉀水溶液（2.0 mol/L，65 mL），並加熱至50℃。之後，加入PdCl ₂(PPh ₃) ₂（0.37 g，0.52 mmol），於65℃下攪拌2小時。冷卻至室溫後，加入飽和氯化鈉水溶液，並使用甲苯進行萃取。利用飽和氯化鈉水溶液清洗有機層，並利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物2-c（產量9.12 g，收率75%）。 To compound 2-a (10.6 g, 26.1 mmol) and compound 2-b (16.2 g, 57.4 mmol), add nitrogen-bubbled toluene (130 mL), ethanol (65 mL), tripotassium phosphate aqueous solution ( 2.0 mol/L, 65 mL), and heated to 50°C. Thereafter, PdCl ₂ (PPh ₃ ) ₂ (0.37 g, 0.52 mmol) was added and stirred at 65° C. for 2 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added, and extraction was performed using toluene. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound 2-c (yield 9.12 g, yield 75%).

＜化合物2-d的合成＞ [化61]

＜Synthesis of Compound 2-d＞ [Chem. 61]

於化合物2-c（9.12 g，19.6 mmol）、雙(頻哪醇合二硼)（15.0 g，58.9 mmol）、乙酸鉀（11.5 g，117.6 mmol）中加入脫水DMSO（200 mL），並加熱至50℃。加入PdCl ₂(dppf)CH ₂Cl ₂（0.80 g，0.98 mmol），於90℃下攪拌3小時。冷卻至室溫後，加入蒸餾水，並進行抽吸過濾。將濾取物溶解於甲苯中，並利用飽和氯化鈉水溶液進行清洗，利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物2-d（產量8.0 g，收率73%）。 Add dehydrated DMSO (200 mL) to compound 2-c (9.12 g, 19.6 mmol), bis(pinacolate diboron) (15.0 g, 58.9 mmol), potassium acetate (11.5 g, 117.6 mmol), and heat to 50°C. PdCl ₂ (dppf)CH ₂ Cl ₂ (0.80 g, 0.98 mmol) was added and stirred at 90°C for 3 hours. After cooling to room temperature, distilled water was added, and suction filtration was performed. The filtrate was dissolved in toluene, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound 2-d (yield 8.0 g, yield 73%).

＜化合物（H-2）的合成＞ [化62]

＜Synthesis of compound (H-2)＞ [Chem. 62]

於氮環境下，於化合物1-c（9.4 g，15.4 mmol）、化合物2-d（3.9 g，6.99 mmol）中依次加入進行了氮起泡的甲苯（60 mL）、乙醇（30 mL）、磷酸三鉀水溶液（2.0 mol/L，30 mL），並加熱至60℃。之後，加入Pd(PPh ₃) ₄（0.081 g，0.070 mmol），於90℃下加熱攪拌3小時。冷卻至室溫後，加入飽和氯化鈉水溶液，並使用甲苯進行萃取。利用飽和氯化鈉水溶液清洗有機層，並利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物（H-2）（產量8.0 g，收率83%）。 Under a nitrogen environment, add toluene (60 mL), ethanol (30 mL), and Tripotassium phosphate aqueous solution (2.0 mol/L, 30 mL), and heated to 60°C. Thereafter, Pd(PPh ₃ ) ₄ (0.081 g, 0.070 mmol) was added, followed by heating and stirring at 90° C. for 3 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added, and extraction was performed using toluene. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound (H-2) (yield 8.0 g, yield 83%).

[合成實施例I-3：化合物（H-3）的合成] ＜化合物3-a的合成＞ [化63]

[Synthesis Example I-3: Synthesis of Compound (H-3)] <Synthesis of Compound 3-a> [Chem. 63]

於化合物1-c（4.60 g，7.5 mmol）、雙(頻哪醇合二硼)（2.85 g，11.2 mmol）、乙酸鉀（2.21 g，22.5 mmol）中加入脫水DMSO（60 mL），並加熱至50℃。加入PdCl ₂(dppf)CH ₂Cl ₂（0.31 g，0.38 mmol），於90℃下攪拌2小時。冷卻至室溫後，加入蒸餾水，並進行抽吸過濾。將濾取物溶解於甲苯中，並利用飽和氯化鈉水溶液進行清洗，利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物3-a（產量4.88 g，收率98%）。 Add dehydrated DMSO (60 mL) to compound 1-c (4.60 g, 7.5 mmol), bis(pinacolate diboron) (2.85 g, 11.2 mmol), potassium acetate (2.21 g, 22.5 mmol), and heat to 50°C. PdCl ₂ (dppf)CH ₂ Cl ₂ (0.31 g, 0.38 mmol) was added and stirred at 90°C for 2 hours. After cooling to room temperature, distilled water was added, and suction filtration was performed. The filtrate was dissolved in toluene, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound 3-a (yield 4.88 g, yield 98%).

＜化合物（H-3）的合成＞ [化64]

＜Synthesis of Compound (H-3)＞ [Chem. 64]

於氮環境下，於化合物3-a（4.88 g，7.39 mmol）、化合物1-a（1.71 g，3.69 mmol）中依次加入進行了氮起泡的甲苯（60 mL）、乙醇（30 mL）、磷酸三鉀水溶液（2.0 mol/L，30 mL），並加熱至60℃。之後，加入Pd(PPh ₃) ₄（0.085 g，0.074 mmol），於90℃下加熱攪拌3小時。冷卻至室溫後，加入飽和氯化鈉水溶液，並使用甲苯進行萃取。利用飽和氯化鈉水溶液清洗有機層，並利用硫酸鎂乾燥後，於減壓下蒸餾去除溶媒。對殘渣進行矽膠管柱層析處理，從而獲得化合物（H-3）（產量3.21 g，收率63%）。 Under a nitrogen environment, add toluene (60 mL), ethanol (30 mL) and Tripotassium phosphate aqueous solution (2.0 mol/L, 30 mL), and heated to 60°C. Thereafter, Pd(PPh ₃ ) ₄ (0.085 g, 0.074 mmol) was added, followed by heating and stirring at 90° C. for 3 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added, and extraction was performed using toluene. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound (H-3) (yield: 3.21 g, yield: 63%).

[各化合物的評價] 對於合成實施例I-1～合成實施例I-3中合成的以下所示的本發明的芳香族化合物即化合物（H-1）、化合物（H-2）及化合物（H-3）、與比較化合物（C-1）及比較化合物（C-2），分別進行以下的評價。 [Evaluation of each compound] The following aromatic compounds of the present invention synthesized in Synthesis Example I-1 to Synthesis Example I-3, that is, compound (H-1), compound (H-2) and compound (H-3), and The comparative compound (C-1) and the comparative compound (C-2) were respectively evaluated as follows.

[化65]

[chem 65]

＜Tg、Ip、Ea、Eg的評價＞藉由差示掃描熱量測定（differential scanning calorimetry，DSC）對各化合物的玻璃轉移溫度（Tg）進行評價。藉由光電子分光法對各化合物的游離電位（Ip）進行評價。藉由從由吸收光譜的吸收端計算出的帶隙（Eg）中減去Ip，來計算出各化合物的電子親和力（Ea）。將結果示於表1。 <Evaluation of Tg, Ip, Ea, Eg> The glass transition temperature (Tg) of each compound was evaluated by differential scanning calorimetry (DSC). The free potential (Ip) of each compound was evaluated by photoelectron spectroscopy. The electron affinity (Ea) of each compound was calculated by subtracting Ip from the band gap (Eg) calculated from the absorption end of the absorption spectrum. The results are shown in Table 1.

[表1] Tg （℃） Ip （eV） Ea （eV） Eg （eV）化合物（H-1） 126 6.30 2.59 3.71 化合物（H-2） 131 6.27 2.56 3.71 化合物（H-3） 134 6.35 2.64 3.71 比較化合物（C-1） 99 - - - 比較化合物（C-2） 87 6.36 2.83 3.53 [Table 1] Tg (°C) Ip (eV) Ea (eV) Eg (eV) Compound (H-1) 126 6.30 2.59 3.71 Compound (H-2) 131 6.27 2.56 3.71 Compound (H-3) 134 6.35 2.64 3.71 Comparative compound (C-1) 99 - - - Comparative compound (C-2) 87 6.36 2.83 3.53

＜溶劑溶解性的評價＞作為各化合物相對於環己基苯（cyclohexyl benzene，CHB）的溶解性的評價，製備1 mL～2 mL左右的環己基苯溶液（各化合物的濃度：2.0質量%），評價各化合物是否溶解於該溶液中。本發明的化合物（H-1）、化合物（H-2）及化合物（H-3）與比較化合物（C-1）及比較化合物（C-2）同樣地，相對於CHB的溶解性為2.0質量%以上，顯示出良好的溶解性。＜Evaluation of solvent solubility＞ As an evaluation of the solubility of each compound with respect to cyclohexylbenzene (CHB), about 1 mL to 2 mL of cyclohexylbenzene solution (concentration of each compound: 2.0 mass %) was prepared, and whether each compound was dissolved in the cyclohexylbenzene (CHB) was evaluated. in solution. Compound (H-1), Compound (H-2) and Compound (H-3) of the present invention have solubility in CHB of 2.0 similarly to Comparative Compound (C-1) and Comparative Compound (C-2). Mass% or more, showing good solubility.

＜耐溶劑性的評價＞如以下般對所獲得的化合物的成膜後的耐溶劑性進行評價。首先，製備使設為試驗對象的化合物以1.5質量%溶解於甲苯中的溶液。於氮手套箱中，將該溶液滴加至玻璃基板上進行旋塗，於加熱板上於100℃下乾燥10分鐘而形成試驗對象的化合物膜。所形成的各化合物膜的膜厚如表2所示般。繼而，將成膜有化合物膜的基板設置於旋塗機上，向基板上滴加150 μL的試驗溶媒，於滴加後靜置60秒鐘而作為耐溶劑性試驗。作為試驗溶媒，使用1-丁醇。之後，使基板以1500 rpm旋轉30秒鐘，繼而以4000 rpm旋轉30秒鐘並使滴加的溶媒旋出。使該基板於加熱板上以100℃乾燥10分鐘。根據各自的膜厚差估算了耐溶劑性試驗前後的膜厚變化。＜Evaluation of solvent resistance＞ The solvent resistance after film formation of the obtained compound was evaluated as follows. First, a solution in which 1.5% by mass of a compound to be tested was dissolved in toluene was prepared. In a nitrogen glove box, this solution was dropped onto a glass substrate, spin-coated, and dried on a hot plate at 100° C. for 10 minutes to form a film of the compound to be tested. The film thickness of each compound film formed is as shown in Table 2. Next, the substrate on which the compound film was formed was set on a spin coater, 150 μL of a test solvent was dropped onto the substrate, and left to stand for 60 seconds after the dropping was used as a solvent resistance test. As a test solvent, 1-butanol was used. Thereafter, the substrate was spun at 1500 rpm for 30 seconds, followed by 4000 rpm for 30 seconds and the added solvent was swirled out. This substrate was dried on a hot plate at 100° C. for 10 minutes. The film thickness changes before and after the solvent resistance test were estimated from the respective film thickness differences.

成膜後的化合物的耐溶劑性基於以下的基準進行評價。 ○：未發現膜厚減少。 ×：發現5 nm以上且未滿15 nm的範圍的膜厚減少。 ××：膜溶解並消失。將耐溶劑性試驗的結果示於表2。 The solvent resistance of the compound after film formation was evaluated based on the following criteria. ◯: No decrease in film thickness was observed. ×: A decrease in film thickness in the range of 5 nm to less than 15 nm was observed. ××: The film dissolves and disappears. Table 2 shows the results of the solvent resistance test.

[表2] 膜厚（nm）耐溶劑性化合物（H-1） 58 ○ 化合物（H-2） 56 ○ 比較化合物（C-1） 58 × 比較化合物（C-2） 53 ×× [Table 2] Film thickness (nm) Solvent resistance Compound (H-1) 58 ○ Compound (H-2) 56 ○ Comparative compound (C-1) 58 x Comparative compound (C-2) 53 ××

由以上的結果可知，本發明的芳香族化合物是耐熱性、溶劑溶解性優異、並且薄膜中的相對於醇系溶劑的耐溶劑性亦優異、以及帶隙大的化合物。From the above results, it can be seen that the aromatic compound of the present invention is excellent in heat resistance and solvent solubility, also excellent in solvent resistance to alcohol-based solvents in thin films, and has a large band gap.

[元件實施例II-1] 利用以下的方法製作有機電場發光元件。對於將銦錫氧化物（indium tin oxide，ITO）透明導電膜於玻璃基板上堆積為50 nm的厚度而成者（吉奧馬科技（Geomatec）公司製造，濺鍍成膜品），使用通常的光微影技術與鹽酸蝕刻而圖案化為2 mm寬的條紋，從而形成陽極。將以所述方式對ITO進行了圖案形成的基板以利用界面活性劑水溶液的超音波清洗、利用超純水的水洗、利用超純水的超音波清洗、利用超純水的水洗的順序清洗後，利用壓縮空氣使其乾燥，最後進行紫外線臭氧清洗。 [Element Example II-1] An organic electroluminescence element was produced by the following method. For those obtained by depositing an indium tin oxide (ITO) transparent conductive film on a glass substrate to a thickness of 50 nm (manufactured by Geomatec Co., Ltd., sputtered into a film product), use ordinary light The anode was formed by patterning into 2 mm wide stripes by lithography and hydrochloric acid etching. The substrate on which ITO was patterned as described above was washed in the order of ultrasonic cleaning with an aqueous surfactant solution, water washing with ultrapure water, ultrasonic cleaning with ultrapure water, and water washing with ultrapure water. , use compressed air to dry it, and finally perform ultraviolet ozone cleaning.

作為電洞注入層形成用組成物，製備使具有下述式（P-1）的重複結構的電洞傳輸性高分子化合物3.0重量%與電子接受性化合物（HI-1）0.6重量%溶解於苯甲酸乙酯中而成的組成物。As a composition for forming a hole injection layer, 3.0% by weight of a hole-transporting polymer compound having a repeating structure of the following formula (P-1) and 0.6% by weight of an electron-accepting compound (HI-1) were prepared by dissolving in Composition made from ethyl benzoate.

[化66]

[chem 66]

於大氣中將該電洞注入層形成用組成物旋塗於所述基板上，於大氣中利用加熱板以240℃乾燥30分鐘，從而形成膜厚40 nm的均勻薄膜，並設為電洞注入層。The composition for forming a hole injection layer was spin-coated on the substrate in the atmosphere, and dried on a hot plate at 240° C. for 30 minutes in the atmosphere to form a uniform thin film with a film thickness of 40 nm, which was used for hole injection. layer.

接下來，使具有下述式（HT-1）的電荷傳輸性高分子化合物溶解於1,3,5-三甲基苯中，製備2.0重量%的溶液。於氮手套箱中將該溶液旋塗於成膜有所述電洞注入層的基板上，利用氮手套箱中的加熱板以230℃乾燥30分鐘，從而形成膜厚40 nm的均勻薄膜，並設為電洞傳輸層。 Next, a charge-transporting polymer compound having the following formula (HT-1) was dissolved in 1,3,5-trimethylbenzene to prepare a 2.0% by weight solution. The solution was spin-coated on the substrate with the hole injection layer formed into a film in a nitrogen glove box, and dried at 230° C. for 30 minutes using a heating plate in a nitrogen glove box to form a uniform film with a film thickness of 40 nm, and Set as the hole transport layer.

[化67]

[chem 67]

接下來，作為發光層的材料，以合成實施例I-1中合成的本發明的化合物（H-1）為2.3重量%、下述化合物（EH-1）為1.15重量%、下述化合物（EH-2）為1.15重量%、下述化合物（D-1）為1.4重量%的濃度溶解於環己基苯中，製備發光層形成用組成物。Next, as the material of the light-emitting layer, the compound (H-1) of the present invention synthesized in Synthesis Example I-1 was 2.3% by weight, the following compound (EH-1) was 1.15% by weight, and the following compound ( EH-2) was dissolved in cyclohexylbenzene at a concentration of 1.15% by weight and the following compound (D-1) was 1.4% by weight to prepare a composition for forming a light-emitting layer.

[化68]

[chem 68]

於氮手套箱中將發光層形成用組成物旋塗於成膜有所述電洞傳輸層的基板上，利用氮手套箱中的加熱板以120℃乾燥20分鐘，從而形成膜厚40 nm的均勻薄膜，並設為發光層。Spin-coat the light-emitting layer-forming composition on the substrate on which the hole transport layer was formed in a nitrogen glove box, and dry it at 120° C. for 20 minutes on a heating plate in a nitrogen glove box to form a film with a film thickness of 40 nm. Uniform thin film, and set as light-emitting layer.

將成膜至發光層的基板設置於真空蒸鍍裝置，將裝置內排氣至2×10 ^-4Pa以下為止。接下來，利用真空蒸鍍法將下述化合物（ET-1）及8-羥基喹啉鋰以2：3的膜厚比共蒸鍍於發光層上，從而形成膜厚30 nm的電子傳輸層。 The substrate on which the light-emitting layer was formed was placed in a vacuum evaporation device, and the inside of the device was evacuated to 2×10 ^-4 Pa or lower. Next, the following compound (ET-1) and lithium 8-hydroxyquinolate were co-deposited on the light-emitting layer at a film thickness ratio of 2:3 by vacuum evaporation method to form an electron transport layer with a film thickness of 30 nm .

[化69]

[chem 69]

繼而，作為陰極蒸鍍用的遮罩，將2 mm寬的條紋狀陰影遮罩（shadow mask）以與陽極的ITO條紋正交的方式密接於基板，藉由鉬舟對鋁進行加熱，形成膜厚80 nm的鋁層，從而形成陰極。Next, as a mask for cathode evaporation, a 2 mm-wide stripe-shaped shadow mask (shadow mask) is closely attached to the substrate so as to be perpendicular to the ITO stripes of the anode, and the aluminum is heated by a molybdenum boat to form a film 80 nm thick aluminum layer, thus forming the cathode.

如以上般，獲得具有2 mm×2 mm尺寸的發光面積部分的有機電場發光元件。As above, an organic electroluminescent element having a light emitting area portion with a size of 2 mm×2 mm was obtained.

[元件實施例II-2] 作為發光層的材料，使用合成實施例I-2中合成的本發明的化合物（H-2）代替化合物（H-1），除此以外與元件實施例II-1同樣地製作有機電場發光元件。 [Element Example II-2] An organic electroluminescent device was fabricated in the same manner as in Device Example II-1, except that the compound (H-2) of the present invention synthesized in Synthesis Example I-2 was used instead of compound (H-1) as a material for the light-emitting layer. .

[元件實施例II-3] 作為發光層的材料，使用合成實施例I-3中合成的本發明的化合物（H-3）代替化合物（H-1），除此以外與元件實施例II-1同樣地製作有機電場發光元件。 [Element Example II-3] An organic electroluminescent device was produced in the same manner as in Device Example II-1, except that the compound (H-3) of the present invention synthesized in Synthesis Example I-3 was used instead of compound (H-1) as a material for the light-emitting layer. .

[元件比較例II-1] 作為發光層的材料，使用所述揭示的比較化合物（C-2）代替化合物（H-1），除此以外與元件實施例II-1同樣地製作有機電場發光元件。 [Element Comparative Example II-1] An organic electroluminescent device was fabricated in the same manner as in Device Example II-1 except that the comparative compound (C-2) disclosed above was used instead of the compound (H-1) as a material for the light-emitting layer.

[元件的評價] 對使元件實施例II-1～元件實施例II-3、及元件比較例II-1中獲得的有機電場發光元件以1,000 cd/m ²發光時的電流效率（cd/A）、外部量子效率（%）進行測定。另外，於以15 mA/cm ²的電流密度持續對元件通電時，對亮度減少至初始亮度的95%為止的時間（LT95）進行測定。將該些測定結果示於表3。表3中，元件實施例II-1～元件實施例II-3的值表示將元件比較例II-1的值設為1的相對值。由表3的結果判明，於使用了本發明的芳香族化合物的有機電場發光元件中性能提高。 [Evaluation of Elements] The ^current efficiency (cd/A ), external quantum efficiency (%) were measured. In addition, when the element was continuously energized at a current density of 15 mA/cm ² , the time (LT95) until the luminance decreased to 95% of the initial luminance was measured. These measurement results are shown in Table 3. In Table 3, the values of Element Example II-1 to Element Example II-3 represent relative values when the value of Element Comparative Example II-1 is set to 1. From the results in Table 3, it is clear that performance is improved in the organic electroluminescent device using the aromatic compound of the present invention.

[表3] 電流效率外部量子效率 LT95 元件實施例II-1 1.00 1.01 1.46 元件實施例II-2 1.00 1.02 1.57 元件實施例II-3 1.02 1.02 1.44 元件比較例II-1 1.00 1.00 1.00 [table 3] current efficiency external quantum efficiency LT95 Element Example II-1 1.00 1.01 1.46 Element Example II-2 1.00 1.02 1.57 Element Example II-3 1.02 1.02 1.44 Element Comparative Example II-1 1.00 1.00 1.00

使用特定的形態對本發明進行了詳細說明，但本領域技術人員明確，能夠於不脫離本發明的意圖與範圍的情況下進行各種變更。本申請案基於2021年6月4日提出申請的日本專利申請案2021-094593及2021年9月13日提出申請的日本專利申請案2021-148727，並藉由引用而援引其整體。 Although this invention was demonstrated in detail using the specific aspect, it is clear for those skilled in the art that various changes can be made without deviating from the intent and range of this invention. This application is based on Japanese Patent Application No. 2021-094593 filed on June 4, 2021 and Japanese Patent Application No. 2021-148727 filed on September 13, 2021, the entirety of which is incorporated by reference.

1:基板 2:陽極 3:電洞注入層 4:電洞傳輸層 5:發光層 6:電子傳輸層 7:陰極 8:有機電場發光元件 1: Substrate 2: anode 3: Hole injection layer 4: Hole transport layer 5: Luminous layer 6: Electron transport layer 7: Cathode 8: Organic electroluminescence element

圖1是示意性地表示本發明的有機電場發光元件的結構的一例的剖面圖。FIG. 1 is a cross-sectional view schematically showing an example of the structure of the organic electroluminescence device of the present invention.

1:基板 1: Substrate

2:陽極 2: anode

3:電洞注入層 3: Hole injection layer

4:電洞傳輸層 4: Hole transport layer

5:發光層 5: Luminous layer

6:電子傳輸層 6: Electron transport layer

7:陰極 7: Cathode

8:有機電場發光元件 8: Organic electroluminescence element

Claims

一種有機電場發光元件，於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件中，所述有機層具有包含下述式（1）所表示的芳香族化合物的層，

式（1）中， Ar ¹～Ar ⁵各自獨立地為氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基， Ar ¹、Ar ²及Ar ⁵的至少一個由下述式（2）或下述式（3）表示； L ¹～L ⁵各自獨立地為可具有取代基的二價的碳數6以上且60以下的芳香族烴基； R各自獨立地表示烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基； m1、m2及m5各自獨立地表示0～5的整數； m3及m4各自獨立地表示1～5的整數； n表示0～10的整數； a1及a2各自獨立地表示0～3的整數； a3表示0～4的整數； a4表示0或1的整數；其中，於a3為4的情況下a4為0；於Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基各自獨立地為烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基；式（1）中，Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ³-(L ³) _m3-、Ar ⁴-(L ⁴) _m4-均不成為氫原子；

式（2）或式（3）中，星號（*）表示與式（1）的鍵； R ¹～R ²⁶各自獨立地表示氫原子、烷基、烯基、炔基、烷氧基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、烷硫基、芳硫基、矽烷基、矽氧基、芳烷基、或芳香族烴基。 An organic electroluminescence element, which has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode. In the organic electroluminescence element, the organic layer has the following formula (1) layer of aromatic compounds,

In formula (1), Ar ¹ to Ar ⁵ are each independently a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have substituents, and at least one of Ar ¹ , Ar ² and Ar ⁵ is composed of Represented by the following formula (2) or the following formula (3); L ¹ to L ⁵ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms that may have a substituent; R each independently represents an alkane group, alkenyl, alkynyl, alkoxy, aryloxy, alkoxycarbonyl, acyl, halogen atom, haloalkyl, alkylthio, arylthio, silyl, siloxy, aralkyl, or Aromatic hydrocarbon group; m1, m2 and m5 each independently represent an integer of 0 to 5; m3 and m4 each independently represent an integer of 1 to 5; n represent an integer of 0 to 10; a1 and a2 each independently represent an integer of 0 to 3 a3 represents an integer of 0 to 4; a4 represents an integer of 0 or 1; wherein, when a3 is 4, a4 is 0; Ar ¹ to Ar ⁵ have a monovalent carbon number of 6 or more and 60 or less The substituents that the aromatic hydrocarbon group may have, and the substituents that the divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms among L ¹ to L ⁵ are independently alkyl, alkenyl, alkynyl, alkoxy group, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxy group, aralkyl group, or aromatic hydrocarbon group; in formula (1), Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ³ -(L ³ ) _m3 -, Ar ⁴ -(L ⁴ ) _m4 - are not hydrogen atoms;

In formula (2) or formula (3), an asterisk (*) represents a bond with formula (1); R ¹ to R ²⁶ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aromatic Oxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group.

如請求項1所述的有機電場發光元件，其中Ar ¹及Ar ²、與n為1以上時的Ar ⁵或n為2以上時的至少一個Ar ⁵由所述式（2）或所述式（3）表示。 The organic electroluminescence element as claimed in claim 1, wherein Ar ¹ and Ar ² , and Ar ⁵ when n is 1 or more or at least one Ar ⁵ when n is 2 or more are obtained from the formula (2) or the formula (3) Representation.

如請求項1或請求項2所述的有機電場發光元件，其中L ¹～L ⁵各自獨立地為可具有取代基的伸苯基或將伸苯基連結兩個以上而成的基。 The organic electroluminescence device according to claim 1 or claim 2, wherein L ¹ to L ⁵ are each independently a phenylene group which may have a substituent or a group formed by linking two or more phenylene groups.

如請求項3所述的有機電場發光元件，其中L ¹～L ⁵各自獨立地為可具有取代基的1,3-伸苯基。 The organic electroluminescent device according to claim 3, wherein L ¹ to L ⁵ are each independently a 1,3-phenylene group which may have a substituent.

如請求項1至請求項4中任一項所述的有機電場發光元件，其中所述芳香族化合物的分子量為1200以上。The organic electroluminescent device according to any one of claim 1 to claim 4, wherein the molecular weight of the aromatic compound is 1200 or more.

如請求項1至請求項5中任一項所述的有機電場發光元件，其中包含所述芳香族化合物的層為發光層。The organic electroluminescence device according to any one of claim 1 to claim 5, wherein the layer containing the aromatic compound is a light emitting layer.

一種顯示裝置，具有如請求項1至請求項6中任一項所述的有機電場發光元件。A display device comprising the organic electroluminescence element described in any one of claim 1 to claim 6.

一種照明裝置，具有如請求項1至請求項6中任一項所述的有機電場發光元件。A lighting device comprising the organic electroluminescent element described in any one of claim 1 to claim 6.

一種芳香族化合物，由下述式（1）表示，

式（1）中， Ar ¹～Ar ⁵各自獨立地為氫原子或可具有取代基的一價的碳數6以上且60以下的芳香族烴基， Ar ¹、Ar ²及Ar ⁵的至少一個由下述式（2）或下述式（3）表示； L ¹～L ⁵各自獨立地為可具有取代基的二價的碳數6以上且60以下的芳香族烴基； R各自獨立地表示烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基； m1、m2及m5各自獨立地表示0～5的整數； m3及m4各自獨立地表示1～5的整數； n表示0～10的整數； a1及a2各自獨立地表示0～3的整數； a3表示0～4的整數； a4表示0或1的整數；其中，於a3為4的情況下a4為0；於Ar ¹～Ar ⁵中一價的碳數6以上且60以下的芳香族烴基可具有的取代基、及L ¹～L ⁵中二價的碳數6以上且60以下的芳香族烴基可具有的取代基各自獨立地為烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基；式（1）中，Ar ¹-(L ¹) _m1-、Ar ²-(L ²) _m2-、Ar ³-(L ³) _m3-、Ar ⁴-(L ⁴) _m4-均不成為氫原子；

式（2）或式（3）中，星號（*）表示與式（1）的鍵； R ¹～R ²⁶各自獨立地表示氫原子、烷基、烯基、芳氧基、烷氧基羰基、醯基、鹵素原子、鹵代烷基、矽烷基、矽氧基、芳烷基、或芳香族烴基。 An aromatic compound represented by the following formula (1),

In formula (1), Ar ¹ to Ar ⁵ are each independently a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have substituents, and at least one of Ar ¹ , Ar ² and Ar ⁵ is composed of Represented by the following formula (2) or the following formula (3); L ¹ to L ⁵ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms that may have a substituent; R each independently represents an alkane group, alkenyl, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group; m1, m2 and m5 each independently represent 0～ An integer of 5; m3 and m4 each independently represent an integer of 1 to 5; n represents an integer of 0 to 10; a1 and a2 each independently represent an integer of 0 to 3; a3 represents an integer of 0 to 4; An integer of 1; wherein, when a3 is 4, a4 is 0; a substituent that a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms in Ar ¹ to Ar ⁵ may have, and L ¹ to L ⁵ The substituents that the divalent aromatic hydrocarbon group having 6 to 60 carbon atoms are independently alkyl, alkenyl, aryloxy, alkoxycarbonyl, acyl, halogen atom, haloalkyl, silyl , siloxy group, aralkyl group, or aromatic hydrocarbon group; In formula (1), Ar ¹ -(L ¹ ) _m1 -, Ar ² -(L ² ) _m2 -, Ar ³ -(L ³ ) _m3 -, Ar ⁴ -(L ⁴ ) _m4 -does not become hydrogen atoms;

In formula (2) or formula (3), an asterisk (*) represents a bond with formula (1); R ¹ to R ²⁶ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryloxy group, an alkoxycarbonyl group , acyl group, halogen atom, haloalkyl group, silyl group, siloxyl group, aralkyl group, or aromatic hydrocarbon group.

如請求項9所述的芳香族化合物，其中a1、a2及a4為0。The aromatic compound according to claim 9, wherein a1, a2 and a4 are 0.

如請求項9所述的芳香族化合物，其中a4為1，a3為0～3的整數。The aromatic compound according to claim 9, wherein a4 is 1, and a3 is an integer of 0-3.

如請求項11所述的芳香族化合物，其中a1、a2及a3相同。The aromatic compound according to claim 11, wherein a1, a2 and a3 are the same.

如請求項9至請求項12中任一項所述的芳香族化合物，其中Ar ¹及Ar ²、與n為1以上時的Ar ⁵或n為2以上時的至少一個Ar ⁵由所述式（2）或所述式（3）表示。 The aromatic compound as described in any one of claim 9 to claim 12, wherein Ar ¹ and Ar ² , and Ar ⁵ when n is 1 or more or at least one Ar ⁵ when n is 2 or more are represented by the formula (2) or said formula (3).

如請求項9至請求項13中任一項所述的芳香族化合物，其中L ¹～L ⁵各自獨立地為可具有取代基的伸苯基或將伸苯基連結兩個以上而成的基。 The aromatic compound according to any one of claim 9 to claim 13, wherein L ¹ to L ⁵ are each independently a phenylene group that may have a substituent or a group formed by linking two or more phenylene groups. .

如請求項14所述的芳香族化合物，其中L ¹～L ⁵各自獨立地為可具有取代基的1,3-伸苯基。 The aromatic compound according to claim 14, wherein L ¹ to L ⁵ are each independently a 1,3-phenylene group which may have a substituent.

如請求項9至請求項15中任一項所述的芳香族化合物，其中分子量為1200以上。The aromatic compound according to any one of claim 9 to claim 15, wherein the molecular weight is 1200 or more.

一種組成物，含有如請求項9至請求項16中任一項所述的芳香族化合物及有機溶劑。A composition comprising the aromatic compound and an organic solvent as described in any one of claim 9 to claim 16.

如請求項17所述的組成物，更含有磷光發光材料及電荷傳輸材料。The composition as claimed in claim 17 further contains a phosphorescent material and a charge transport material.

如請求項18所述的組成物，其中所述電荷傳輸材料包含下述式（250）所表示的化合物及/或下述式（240）所表示的化合物，

式（250）中， W各自獨立地表示CH或N，至少一個W為N； Xa ¹、Ya ¹、及Za ¹各自獨立地表示可具有取代基的碳數6～30的二價芳香族烴基、或可具有取代基的碳數3～30的二價芳香族雜環基； Xa ²、Ya ²及Za ²各自獨立地表示氫原子、可具有取代基的碳數6～30的一價芳香族烴基、或可具有取代基的碳數3～30的一價芳香族雜環基； g11、h11、及j11各自獨立地表示0～6的整數， g11、h11、j11的至少一個為1以上的整數；於g11為2以上的情況下，存在多個的Xa ¹可相同亦可不同；於h11為2以上的情況下，存在多個的Ya ¹可相同亦可不同；於j11為2以上的情況下，存在多個的Za ¹可相同亦可不同； R ³¹表示氫原子或取代基，四個R ³¹可相同亦可不同；其中，於g11、h11、或j11為0的情況下，分別對應的Xa ²、Ya ²、Za ²不為氫原子；

式（240）中， Ar ⁶¹¹、Ar ⁶¹²各自獨立地表示可具有取代基的碳數6～50的一價芳香族烴基； R ⁶¹¹、R ⁶¹²各自獨立地表示氘原子、鹵素原子、或可具有取代基的碳數6～50的一價芳香族烴基； G表示單鍵、或可具有取代基的碳數6～50的二價芳香族烴基； n ⁶¹¹、n ⁶¹²各自獨立地為0～4的整數。 The composition according to claim 18, wherein the charge transport material comprises a compound represented by the following formula (250) and/or a compound represented by the following formula (240),

In formula (250), W each independently represents CH or N, and at least one W is N; Xa ¹ , Ya ¹ , and Za ¹ each independently represent a divalent aromatic hydrocarbon group with 6 to 30 carbon atoms that may have substituents , or a divalent aromatic heterocyclic group with 3 to 30 carbon atoms that may have a substituent; Xa ² , Ya ² and Za ² each independently represent a hydrogen atom, and a monovalent aromatic heterocyclic group with 6 to 30 carbon atoms that may have a substituent An aromatic hydrocarbon group, or a monovalent aromatic heterocyclic group with 3 to 30 carbon atoms that may have a substituent; g11, h11, and j11 each independently represent an integer of 0 to 6, and at least one of g11, h11, and j11 is 1 or more is an integer; when g11 is 2 or more, multiple Xa ^1s may be the same or different; when h11 is 2 or more, multiple Ya ^1s may be the same or different; j11 is 2 or more In the case of , multiple Za ^1s may be the same or different; R ³¹ represents a hydrogen atom or a substituent, and the four R ^31s may be the same or different; wherein, when g11, h11, or j11 is 0, The corresponding Xa ² , Ya ² , and Za ² are not hydrogen atoms;

In formula (240), Ar ⁶¹¹ and Ar ⁶¹² each independently represent a monovalent aromatic hydrocarbon group with 6 to 50 carbon atoms that may have substituents; R ⁶¹¹ and R ⁶¹² each independently represent a deuterium atom, a halogen atom, or may have A monovalent aromatic hydrocarbon group with a carbon number of 6 to 50 as a substituent; G represents a single bond or a divalent aromatic hydrocarbon group with a carbon number of 6 to 50 that may have a substituent; n ⁶¹¹ and n ⁶¹² are each independently 0 to 4 an integer of .

如請求項19所述的組成物，其中所述式（250）中的三個W中的至少兩個為N。The composition as claimed in item 19, wherein at least two of the three Ws in the formula (250) are N.

如請求項20所述的組成物，其中所述式（250）中的W全部為N。The composition according to claim 20, wherein all W in the formula (250) are N.

如請求項19所述的組成物，其中所述式（240）中的Ar ⁶¹¹及Ar ⁶¹²各自獨立地為可具有取代基的多個苯環以鏈狀或分支的方式鍵結而成的一價基。 The composition as described in claim item 19, wherein Ar ⁶¹¹ and Ar ⁶¹² in the formula (240) are each independently a combination of multiple benzene rings that may have substituents bonded in a chain or branched manner. price base.

如請求項19所述的組成物，其中所述式（240）中的R ⁶¹¹及R ⁶¹²各自獨立地為可具有取代基的碳數6～30的一價芳香族烴基。 The composition according to claim 19, wherein R ⁶¹¹ and R ⁶¹² in the formula (240) are each independently a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have substituents.

如請求項19所述的組成物，其中所述式（240）中的n ⁶¹¹及n ⁶¹²各自獨立地為0或1。 The composition according to claim 19, wherein n ⁶¹¹ and n ⁶¹² in the formula (240) are each independently 0 or 1.

一種薄膜形成方法，具有利用濕式成膜法將如請求項17至請求項24中任一項所述的組成物成膜的步驟。A thin film forming method comprising the step of forming a film of the composition according to any one of claim 17 to claim 24 by a wet film forming method.

一種有機電場發光元件的製造方法，其中所述有機電場發光元件於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件的製造方法中，具有使用如請求項17至請求項24中任一項所述的組成物並利用濕式成膜法形成所述有機層的步驟。 A method for manufacturing an organic electroluminescent element, wherein the organic electroluminescent element has an anode and a cathode on a substrate, and an organic layer is provided between the anode and the cathode. In the method for manufacturing the organic electroluminescent element, There is a step of forming the organic layer using the composition described in any one of claim 17 to claim 24 by a wet film-forming method.

如請求項26所述的有機電場發光元件的製造方法，其中所述有機層為發光層。The method for manufacturing an organic electroluminescence element as claimed in claim 26, wherein the organic layer is a light emitting layer.

一種有機電場發光元件的製造方法，其中所述有機電場發光元件於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件的製造方法中，所述有機層包含發光層與電子傳輸層，包括：使用如請求項17至請求項24中任一項所述的組成物並利用濕式成膜法形成所述發光層的步驟；以及使用包含電子傳輸材料及溶劑的電子傳輸層形成用組成物並利用濕式成膜法形成所述電子傳輸層的步驟。 A method for manufacturing an organic electroluminescent element, wherein the organic electroluminescent element has an anode and a cathode on a substrate, and an organic layer is provided between the anode and the cathode. In the method for manufacturing the organic electroluminescent element, The organic layer includes a light emitting layer and an electron transport layer, Including: using the composition described in any one of Claim 17 to Claim 24 and using a wet film-forming method to form the light-emitting layer; and A step of forming the electron transport layer by a wet film-forming method using a composition for forming an electron transport layer including an electron transport material and a solvent.

如請求項28所述的有機電場發光元件的製造方法，其中所述電子傳輸層形成用組成物中包含的溶劑為醇系溶劑。The method for producing an organic electroluminescence device according to claim 28, wherein the solvent contained in the composition for forming an electron transport layer is an alcohol-based solvent.

一種有機電場發光元件，於基板上具有陽極及陰極，於所述陽極與所述陰極之間具有有機層，所述有機電場發光元件中，所述有機層包含發光層，所述發光層包含如請求項9至請求項16中任一項所述的芳香族化合物、磷光發光材料及電荷傳輸材料，所述電荷傳輸材料包含下述式（250）所表示的化合物及/或下述式（240）所表示的化合物，

式（240）中， Ar ⁶¹¹、Ar ⁶¹²各自獨立地表示可具有取代基的碳數6～50的一價芳香族烴基； R ⁶¹¹、R ⁶¹²各自獨立地表示氘原子、鹵素原子、或可具有取代基的碳數6～50的一價芳香族烴基； G表示單鍵、或可具有取代基的碳數6～50的二價芳香族烴基； n ⁶¹¹、n ⁶¹²各自獨立地為0～4的整數。 An organic electroluminescent element, having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, in the organic electroluminescent element, the organic layer includes a light-emitting layer, and the light-emitting layer includes such as The aromatic compound, phosphorescent material and charge transport material described in any one of claim 9 to claim 16, the charge transport material comprises a compound represented by the following formula (250) and/or the following formula (240 ) represented by the compound,

如請求項30所述的有機電場發光元件，其中所述式（250）中的三個W中的至少兩個為N。The organic electroluminescence element according to claim 30, wherein at least two of the three Ws in the formula (250) are N.

如請求項31所述的有機電場發光元件，其中所述式（250）中的W全部為N。The organic electroluminescence element according to claim 31, wherein all W in the formula (250) are N.