TWI473805B - Organic electroluminescence device - Google Patents

Organic electroluminescence device Download PDF

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TWI473805B
TWI473805B TW98135633A TW98135633A TWI473805B TW I473805 B TWI473805 B TW I473805B TW 98135633 A TW98135633 A TW 98135633A TW 98135633 A TW98135633 A TW 98135633A TW I473805 B TWI473805 B TW I473805B
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Masayuki Hayashi
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Udc Ireland Ltd
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Description

有機電場發光元件Organic electric field light-emitting element

本發明是有關於一種有機電場發光元件(Organic Electroluminescence Device，以下有時稱為有機EL元件)，其可有效用於全彩顯示器(full color display)、背光(back light)、照明光源等的面光源或印表機(printer)等的光源陣列(array)等。The present invention relates to an organic electroluminescence device (hereinafter sometimes referred to as an organic EL device), which can be effectively used for a face of a full color display, a backlight, an illumination source, or the like. A light source array such as a light source or a printer, or the like.

目前，對各種顯示元件的研究開發很活躍，其中，有機EL元件由於可以低電壓獲得高亮度的發光，故而作為有前途的顯示元件而受到關注。At present, research and development of various display elements have been active. Among them, organic EL elements have attracted attention as a promising display element because they can obtain high-luminance light emission at a low voltage.

有機EL元件是由發光層或包含發光層的多層有機層與夾持有機層的對向電極所構成。有機EL元件是用以獲得利用下述發光中之至少一者的發光的元件：來自於自陰極注入的電子與自陽極注入的電洞在有機層進行再結合而生成的激子的發光；以及來自於自上述激子進行能量轉移(energy transfer)而生成的其他分子的激子的發光。The organic EL element is composed of a light-emitting layer or a plurality of organic layers including a light-emitting layer and a counter electrode sandwiching the organic layer. The organic EL element is an element for obtaining light emission using at least one of light emission from the following: light emission from excitons generated by recombination of electrons injected from the cathode and holes injected from the anode in an organic layer; The luminescence of excitons from other molecules generated by energy transfer from the above excitons.

迄今為止，有機EL元件使用將功能分離的積層結構，藉此亮度及元件效率得到較大改善而得以發展。例如經常使用：積層著電子傳輸層與發光層、或者電洞傳輸層與發光層的兩層積層型元件；積層著電洞傳輸層、發光層以及電子傳輸層的三層積層型元件；以及積層著電洞傳輸層、發光層、電洞阻止層以及電子傳輸層的四層積層型元件。Heretofore, the organic EL element has been developed using a laminated structure in which functions are separated, whereby brightness and element efficiency are greatly improved. For example, it is often used: a two-layer laminated type element in which an electron transport layer and a light-emitting layer or a hole transport layer and a light-emitting layer are laminated; a three-layer laminated type element in which a hole transport layer, a light-emitting layer, and an electron transport layer are laminated; and a laminate A four-layer laminated element of a hole transport layer, a light-emitting layer, a hole stop layer, and an electron transport layer.

然而，為了將有機EL元件實用化，而進一步謀求驅動電壓的降低及發光效率的提高。However, in order to put the organic EL element into practical use, it is further required to reduce the driving voltage and improve the luminous efficiency.

例如進行了以下材料的探索：用以促進自陰極注入電子及傳輸電子的電子傳輸材料、及用以促進自陽極注入電洞及傳輸電洞的電洞傳輸材料。尤其揭示有一種可自陰極快速地注入電子且電子傳輸性優異的電子傳輸材料。例如揭示有特定結構的含氮雜環衍生物作為電子傳輸材料並作為電子傳輸性優異的電子傳輸材料(例如參照專利文獻1)。一般認為專利文獻1中所揭示的以通式(1)所表示的含氮雜環衍生物作為電子傳輸材料而包含於發光層、電子注入層、電子傳輸層等中，可以低電壓獲得高發光效率。發光材料揭示有作為螢光發光材料的4',4"-雙(2,2-二苯乙烯基)-9,10-二苯基蒽。For example, the following materials have been explored: an electron transport material for promoting electron injection from a cathode and electron transport, and a hole transport material for promoting injection of a hole from an anode and a transmission hole. In particular, there is disclosed an electron transporting material which can rapidly inject electrons from a cathode and is excellent in electron transport property. For example, a nitrogen-containing heterocyclic derivative having a specific structure is disclosed as an electron transporting material and is an electron transporting material excellent in electron transport property (for example, see Patent Document 1). It is considered that the nitrogen-containing heterocyclic derivative represented by the general formula (1) disclosed in Patent Document 1 is contained in the light-emitting layer, the electron injecting layer, the electron transporting layer or the like as an electron transporting material, and high light emission can be obtained at a low voltage. effectiveness. The luminescent material reveals 4',4"-bis(2,2-distyryl)-9,10-diphenylfluorene as a fluorescent luminescent material.

另一方面，亦進行了發光效率高的發光材料的探索。尤其是磷光發光材料可期待量子產率比螢光發光材料高，因此繼續進行探索。例如揭示有四牙以上的多牙鉑錯合物作為具有高發光效率且驅動耐久性優異的發光材料(例如參照專利文獻2)。On the other hand, the exploration of a light-emitting material having high luminous efficiency has also been conducted. In particular, phosphorescent materials are expected to have higher quantum yields than fluorescent materials, and therefore continue to be explored. For example, a multi-dental platinum complex having four or more teeth is disclosed as a light-emitting material having high luminous efficiency and excellent driving durability (for example, see Patent Document 2).

然而，使用磷光發光材料，不易構成具有充分的遷移率、同時實現高發光效率與耐久性且在實用上有用的有機EL元件，仍存在較多的問題。However, the use of a phosphorescent material is not easy to constitute an organic EL device having sufficient mobility and achieving high luminous efficiency and durability and being practically useful, and there are still many problems.

[先行技術文獻][Advanced technical literature] [專利文獻][Patent Literature]

[專利文獻1]日本專利特開2004-217547號公報[Patent Document 1] Japanese Patent Laid-Open Publication No. 2004-217547

[專利文獻2]日本專利特開2006-93542號公報[Patent Document 2] Japanese Patent Laid-Open Publication No. 2006-93542

本發明的目的在於提供一種低電壓且高發光效率的有機電場發光元件。An object of the present invention is to provide an organic electric field light-emitting element having low voltage and high luminous efficiency.

本發明的上述課題利用下述手段來達成。The above problems of the present invention are achieved by the following means.

＜1＞一種有機電場發光元件，在基板上包括一對電極與在該些電極間包含發光層及電子傳輸層的有機層，上述發光層包含電子傳輸性磷光發光材料，且在上述發光層與陰極之間包含上述電子傳輸層，上述電子傳輸層含有以下述通式(1)所表示的含氮雜環化合物：<1> An organic electroluminescent device comprising: a pair of electrodes and an organic layer including a light-emitting layer and an electron transport layer between the electrodes; wherein the light-emitting layer comprises an electron-transporting phosphorescent material, and the light-emitting layer and the light-emitting layer The electron transport layer is contained between the cathodes, and the electron transport layer contains a nitrogen-containing heterocyclic compound represented by the following formula (1):

(通式(1)中，A1 ～A3 相互獨立為氮原子或碳原子；Ar1 為經取代或未經取代的核碳數6～60的芳基、或者經取代或未經取代的核碳數3～60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基；其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基；L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60的伸芳基、經取代或未經取代的核碳數3～60的雜伸芳基、或者經取代或未經取代的伸芴基；R為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基，n為0～5的整數，當n大於等於2時，多個R可相同亦可不同，且鄰接的多個R基彼此亦可鍵結而形成碳環式脂肪族環或碳環式芳香族環)。(In the formula (1), A 1 to A 3 are each independently a nitrogen atom or a carbon atom; and Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or substituted or unsubstituted. a heteroaryl group having 3 to 60 carbon atoms, Ar 2 being a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 60 carbon atoms. a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; wherein any of Ar 1 and Ar 2 is substituted Or an unsubstituted fused ring group having a nuclear carbon number of 10 to 60, or a substituted or unsubstituted monoheterocyclic ring group having a core carbon number of 3 to 60; and L 1 and L 2 are each independently a single bond and substituted Or an unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, or a substituted or unsubstituted hydrazine group; R is hydrogen Atom, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, substituted or unsubstituted carbon number 1 to 20 Alkyl, or substituted or unsubstituted The number of alkoxy groups is from 1 to 20, and n is an integer of from 0 to 5. When n is 2 or more, a plurality of R groups may be the same or different, and a plurality of adjacent R groups may be bonded to each other to form a carbocyclic ring. Aliphatic ring or carbocyclic aromatic ring).

＜2＞如＜1＞所述之有機電場發光元件，其中含有至少一種金屬錯合物來作為上述電子傳輸性磷光發光材料，該金屬錯合物具有三牙以上的配位基，且該配位基為鏈狀配位基並具有以下述通式(2)所表示的部分結構：<2> The organic electroluminescent device according to <1>, wherein at least one metal complex is contained as the electron transporting phosphorescent material, and the metal complex has a ligand of three or more teeth, and the compound The group is a chain ligand and has a partial structure represented by the following formula (2):

(通式(2)中，M11 表示金屬離子，L11 、L12 、L13 、L14 、L15 相互獨立表示配位在M11 上的配位基；在L11 、L14 之間並不進一步存在原子群而形成環狀配位基；L15 並不與L11 及L14 兩者鍵結形成環狀配位基；Y11 、Y12 、Y13 相互獨立表示連結基、單鍵或者雙鍵；L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵表示單鍵或雙鍵；n11 表示0～4)。(In the formula (2), M 11 represents a metal ion, and L 11 , L 12 , L 13 , L 14 and L 15 independently of each other represent a ligand coordinated to M 11 ; between L 11 and L 14 The atomic group is not further formed to form a cyclic ligand; L 15 is not bonded to both L 11 and L 14 to form a cyclic ligand; Y 11 , Y 12 and Y 13 are independent of each other to represent a linking group, Key or double bond; L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L 14 represent a single bond or a double bond ;n 11 means 0 to 4).

＜3＞如＜2所述之有機電場發光元件，其中上述電子傳輸性磷光發光材料為鉑錯合物。<3> The organic electroluminescence device according to <2, wherein the electron transporting phosphorescent material is a platinum complex.

＜4＞如＜1＞至＜3＞中任一項所述之有機電場發光元件，其中以上述通式(1)所表示的含氮雜環化合物為以下述通式(3)所表示的含氮雜環化合物：The organic electroluminescent device of any one of the above-mentioned general formula (1), wherein the nitrogen-containing heterocyclic compound represented by the above formula (1) is represented by the following formula (3). Nitrogen-containing heterocyclic compounds:

(通式(3)中，A1 ～A3 、Ar1 、Ar2 、L1 以及L2 與上述通式(1)中同義；R'與上述通式(1)中的R同義)。(In the formula (3), A 1 to A 3 , Ar 1 , Ar 2 , L 1 and L 2 have the same meanings as in the above formula (1); R' has the same meaning as R in the above formula (1)).

＜5＞如＜1＞至＜3＞中任一項所述之有機電場發光元件，其中以上述通式(1)所表示的含氮雜環化合物為以下述通式(4)所表示的含氮雜環化合物：The organic electroluminescent device of any one of the above-mentioned general formula (1), wherein the nitrogen-containing heterocyclic compound represented by the above formula (1) is represented by the following formula (4). Nitrogen-containing heterocyclic compounds:

(通式(4)中，A1 、A2 、Ar1 、Ar2 、L1 以及L2 與上述通式(1)中同義；R'、R"與上述通式(1)中的R同義，且相互可相同亦可不同)。(In the formula (4), A 1 , A 2 , Ar 1 , Ar 2 , L 1 and L 2 are synonymous with the above formula (1); R', R" and R in the above formula (1) Synonymous, and the same or different from each other).

＜6＞如＜1＞至＜5＞中任一項所述之有機電場發光元件，其中以上述通式(1)、(3)～(4)所表示的含氮雜環化合物中，上述L1 及L2 相互獨立為選自以下述化學式所表示的二價基組群中的基：The organic electroluminescent device according to any one of the above-mentioned general formulas (1), (3) to (4), wherein the above-mentioned nitrogen-containing heterocyclic compound represented by the above formula (1), (3) to (4), L 1 and L 2 are each independently a group selected from the group of divalent groups represented by the following chemical formula:

＜7＞如＜1＞至＜6＞中任一項所述之有機電場發光元件，其中以上述通式(1)、(3)～(4)所表示的含氮雜環化合物中，上述Ar1 及Ar2 的至少一者為以下述通式(5)～(14)所表示的基：The organic electroluminescent device of any one of the above-mentioned general formula (1), (3) - (4), the said At least one of Ar 1 and Ar 2 is a group represented by the following general formulae (5) to (14):

(式中，R1 ～R92 相互獨立為氫原子、鹵素原子、經取代或未經取代的碳數1～20的烷基、經取代或未經取代的碳數1～20的烷氧基、經取代或未經取代的核碳數6～40的芳氧基、經取代或未經取代的核碳數12～80的二芳胺基、經取代或未經取代的核碳數6～40的芳基、經取代或未經取代的核碳數3～40的雜芳基、或者經取代或未經取代的核碳數18～120的二芳胺基芳基，L3 為選自由單鍵及以下述化學式所表示的二價基所組成組群中的基：(wherein R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 80 carbon atoms, a substituted or unsubstituted nucleus carbon number 6 to An aryl group of 40, a substituted or unsubstituted heteroaryl group having a core carbon number of 3 to 40, or a substituted or unsubstituted diarylaminoaryl group having a core number of 18 to 120, and L 3 is selected from A single bond and a group consisting of a divalent group represented by the following chemical formula:

＜8＞如＜1＞至＜7＞中任一項所述之有機電場發光元件，其中上述電子傳輸性磷光發光材料包含以下述通式(15)所表示的部分結構：The organic electroluminescent light-emitting device according to any one of <1> to <7> wherein the electron-transporting phosphorescent material comprises a partial structure represented by the following formula (15):

(通式(15)中，M21 表示金屬離子，Y21 表示連結基、單鍵或者雙鍵；Y22 、Y23 相互獨立表示單鍵或連結基；Q21 、Q22 相互獨立表示形成含氮雜環的原子群，由Q21 所形成的環與Y21 之間的鍵及由Q22 所形成的環與Y21 之間的鍵表示單鍵或雙鍵；X21 、X22 相互獨立表示氧原子、硫原子、經取代或未經取代的氮原子；R21 、R22 、R23 、R24 相互獨立表示氫原子或取代基，R21 及R22 以及R23 及R24 亦可分別鍵結而形成環；L25 表示配位在M21 上的配位基；n21 表示0～4的整數)。(In the formula (15), M 21 represents a metal ion, Y 21 represents a linking group, a single bond or a double bond; and Y 22 and Y 23 each independently represent a single bond or a linking group; and Q 21 and Q 22 independently represent each other to form a The atomic group of the nitrogen heterocycle, the bond between the ring formed by Q 21 and Y 21 and the bond formed between Q 22 and Y 21 represent a single bond or a double bond; X 21 and X 22 are independent of each other And an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom; R 21 , R 22 , R 23 , and R 24 each independently represent a hydrogen atom or a substituent, and R 21 and R 22 and R 23 and R 24 may also Each of the bonds is bonded to form a ring; L 25 represents a ligand coordinated to M 21 ; n 21 represents an integer of 0 to 4).

＜9＞如＜8＞所述之有機電場發光元件，其中包含四牙配位基的至少一種鉑錯合物來作為上述電子傳輸性磷光發光材料，該鉑錯合物包含以下述通式(16)所表示的部分結構：<9> The organic electroluminescent device according to <8>, wherein at least one platinum complex comprising a tetradentate ligand is used as the electron transporting phosphorescent material, and the platinum complex comprises the following formula ( 16) Part of the structure represented:

(通式(16)中，Z1 表示以氮原子而配位在鉑上的含氮雜環；L1 表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基)。(In the formula (16), Z 1 represents a nitrogen-containing heterocyclic ring coordinated to platinum by a nitrogen atom; L 1 represents a single bond or a linking group; and R 1 , R 3 and R 4 independently of each other represent a hydrogen atom or a substituent. A group, R 2 represents a substituent).

＜10＞如＜9＞所述之有機電場發光元件，其中包含以上述通式(16)所表示的部分結構的四牙配位基的鉑錯合物為以下述通式(17)所表示的鉑錯合物：<10> The organic electroluminescent device according to <9>, wherein the platinum complex comprising a tetradentate ligand having a partial structure represented by the above formula (16) is represented by the following formula (17) Platinum complex:

(通式(17)中，Z1 及Z2 相互獨立表示以氮原子而配位在鉑上的含氮雜環；Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基)。(In the formula (17), Z 1 and Z 2 independently of each other represent a nitrogen-containing heterocyclic ring coordinated to a platinum atom; and Q 2 represents a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom; a group bonded to platinum; L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group; R 1 , R 3 and R 4 independently of each other represent a hydrogen atom or a substituent, and R 2 represents a substituent).

＜11＞如＜10＞所述之有機電場發光元件，其中以上述通式(17)所表示的鉑錯合物為以下述通式(18)所表示的鉑錯合物：<11> The organic electroluminescent device according to <10>, wherein the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (18):

(通式(18)中，Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0～3的整數)。(In the formula (18), Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom; and L 1 , L 2 and L 3 independently represent a single bond or a linkage; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3).

＜12＞如＜10＞所述之有機電場發光元件，其中以上述通式(17)所表示的鉑錯合物為以下述通式(19)所表示的鉑錯合物：<12> The organic electroluminescent device according to <10>, wherein the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (19):

(通式(19)中，Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0～3的整數)。(In the formula (19), Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom; and L 1 , L 2 and L 3 independently of each other represent a single bond or A linking group; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3).

＜13＞如＜12＞所述之有機電場發光元件，其中以上述通式(19)所表示的鉑錯合物為以下述通式(20)所表示的化合物：<13> The organic electroluminescent device according to <12>, wherein the platinum complex represented by the above formula (19) is a compound represented by the following formula (20):

(通式(20)中，L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基；n、m相互獨立表示0～3的整數；R5 、R7 、R8 相互獨立表示氫原子或取代基，R6 表示取代基)。(In the formula (20), L 1 , L 2 and L 3 each independently represent a single bond or a linking group; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a R b and independently represent a substituent; n and m each independently represent an integer of 0 to 3; R 5 , R 7 and R 8 each independently represent a hydrogen atom or a substituent, and R 6 represents a substituent).

＜14＞如＜1＞至＜13＞中任一項所述之有機電場發光元件，其中上述發光層包含電洞傳輸性主體材料(host material)。The organic electroluminescence device according to any one of <1> to <13> wherein the light-emitting layer comprises a hole transporting host material.

＜15＞如＜1＞至＜14＞中任一項所述之有機電場發光元件，其中上述含有含氮雜環化合物的電子傳輸層包含還原性摻雜劑(dopant)。The organic electroluminescence device according to any one of <1> to <14> wherein the electron transport layer containing the nitrogen-containing heterocyclic compound contains a reducing dopant.

＜16＞如＜1＞至＜15＞中任一項所述之有機電場發光元件，其中上述還原性摻雜劑為選自由鹼金屬、鹼土金屬、稀土金屬、鹼金屬的氧化物、鹼金屬的鹵化物、鹼土金屬的氧化物、鹼土金屬的鹵化物、稀土金屬的氧化物、稀土金屬的鹵化物、鹼金屬的有機錯合物、鹼土金屬的有機錯合物以及稀土金屬的有機錯合物所組成組群中的至少一種。The organic electroluminescent device according to any one of <1>, wherein the reducing dopant is an oxide selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal, and an alkali metal. Halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and organic misalignments of rare earth metals At least one of the group consisting of objects.

[發明之效果][Effects of the Invention]

根據本發明，提供一種低電壓且高發光效率的有機電場發光元件。According to the present invention, an organic electric field light-emitting element of low voltage and high luminous efficiency is provided.

專利文獻1中記載的特定結構的含氮雜環衍生物，其電子傳輸性優異，且該含氮雜環衍生物與螢光發光材料的發光層的組合可獲得確實地降低驅動電壓的效果。然而，在發光層中使用磷光發光材料的情況下，明顯存在導致發光效率降低的弊端。上述情況的機制並不明確，推測如下。在將通常使用的電洞傳輸性材料作為主體(host)的情況下，由於磷光發光材料亦大多為電洞傳輸性，故而若在電子傳輸層中使用含氮雜環衍生物而使電子至發光層的注入過高，則在發光層內電子的流動停滯。因此，電子與電洞的載子平衡(carrier balance)破壞，而引起發光效率的降低。The nitrogen-containing heterocyclic derivative having a specific structure described in Patent Document 1 is excellent in electron transport property, and the combination of the nitrogen-containing heterocyclic derivative and the light-emitting layer of the fluorescent material can obtain an effect of reliably lowering the driving voltage. However, in the case where a phosphorescent material is used in the light-emitting layer, there is a clear disadvantage that the luminous efficiency is lowered. The mechanism of the above situation is not clear, and it is presumed as follows. In the case where a commonly used hole transporting material is used as a host, since the phosphorescent material is mostly hole-transporting, electron-to-luminescence is used if a nitrogen-containing heterocyclic derivative is used in the electron transporting layer. When the implantation of the layer is too high, the flow of electrons in the light-emitting layer is stagnant. Therefore, the carrier balance of the electrons and the holes is broken, resulting in a decrease in luminous efficiency.

經推測，藉由本發明中的電子傳輸性高的磷光發光材料，可提高發光層的電子的流動，電洞與電子的載子平衡，從而可同時實現低電壓化與高效率。尤其在使用四牙配位基的鉑錯合物的情況下，可實現高效率與低驅動電壓。It is presumed that the phosphorescent material having high electron transport property in the present invention can increase the flow of electrons in the light-emitting layer, and the balance between the hole and the electron carrier can achieve low voltage and high efficiency at the same time. Particularly in the case of a platinum complex using a tetradentate ligand, high efficiency and low driving voltage can be achieved.

為讓本發明之上述特徵和優點能更明顯易懂，下文特舉實施例，並配合所附圖式作詳細說明如下。The above described features and advantages of the present invention will be more apparent from the following description.

以下，對本發明的有機電場發光元件(以下，有時適當稱為「有機EL元件」)進行詳細說明。Hereinafter, the organic electroluminescence device (hereinafter sometimes referred to as "organic EL device" as appropriate) of the present invention will be described in detail.

本發明的有機EL元件在基板上具有陰極與陽極，且在兩電極之間具有包含有機發光層(以下，有時僅稱為「發光層」)的有機層。自發光元件的性質考慮，較好的是陽極及陰極中的至少一個電極為透明。The organic EL device of the present invention has a cathode and an anode on a substrate, and an organic layer including an organic light-emitting layer (hereinafter sometimes referred to simply as a "light-emitting layer") between the electrodes. In view of the nature of the self-luminous element, it is preferred that at least one of the anode and the cathode be transparent.

本發明中的有機層可為單層或積層的任一種。作為積層時的態樣，較好的是自陽極側起依序積層著電洞傳輸層、發光層、電子傳輸層的態樣。而且，亦可在電洞傳輸層與發光層之間、或者在發光層與電子傳輸層之間具有電荷阻擋層等。亦可在陽極與電洞傳輸層之間具有電洞注入層，且亦可在陰極與電子傳輸層之間具有電子注入層。另外，亦可將各層分為多層次級層。The organic layer in the present invention may be either a single layer or a laminate. As a state in which the layer is laminated, it is preferred that the layers of the hole transport layer, the light-emitting layer, and the electron transport layer are sequentially stacked from the anode side. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light emitting layer or between the light emitting layer and the electron transport layer. A hole injection layer may also be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Alternatively, the layers can be divided into multiple layers of secondary layers.

有機EL元件在基板上具有一對電極與在該些電極間包含發光層及電子傳輸層的有機層，上述發光層含有電子傳輸性磷光發光材料，且在上述發光層與陰極之間包含上述電子傳輸層，上述電子傳輸層含有以下述通式(1)所表示的含氮雜環化合物。The organic EL device has a pair of electrodes on the substrate, and an organic layer including a light-emitting layer and an electron transport layer between the electrodes, wherein the light-emitting layer contains an electron-transporting phosphorescent material, and the electrons are contained between the light-emitting layer and the cathode. In the transport layer, the electron transport layer contains a nitrogen-containing heterocyclic compound represented by the following formula (1).

通式(1)中，A1 ～A3 相互獨立為氮原子或碳原子。Ar1 為經取代或未經取代的核碳數6～60的芳基、或者經取代或未經取代的核碳數3～60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60的伸芳基、經取代或未經取代的核碳數3～60的雜伸芳基、或者經取代或未經取代的伸芴基。R為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基，n為0～5的整數，當n大於等於2時，多個R可相同亦可不同，而且，鄰接的多個R基彼此亦可鍵結而形成碳環式脂肪族環或碳環式芳香族環。In the formula (1), A 1 to A 3 are each independently a nitrogen atom or a carbon atom. Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and Ar 2 is a hydrogen atom, substituted or not a substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or Unsubstituted alkoxy group having 1 to 20 carbon atoms. Wherein, any one of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or a substituted or unsubstituted monoheterocyclic group having 3 to 60 carbon atoms; . L 1 and L 2 are each independently a single bond, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, or Substituted or unsubstituted thiol. R is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number of 1 ～20 alkyl, or substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is 2 or more, a plurality of R may be the same or different, and Adjacent plurality of R groups may also be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.

較好的是含有至少一種金屬錯合物來作為上述電子傳輸性磷光發光材料，該金屬錯合物具有三牙以上的配位基，且該配位基為鏈狀配位基並具有以下述通式(2)所表示的部分結構。It is preferred to contain at least one metal complex as the electron transporting phosphorescent material, the metal complex having a ligand of three or more teeth, and the ligand is a chain ligand and has the following Partial structure represented by the formula (2).

通式(2)中，M11 表示金屬離子，L11 、L12 、L13 、L14 、L15 相互獨立表示配位在M11 上的配位基。在L11 、L14 之間並不進一步存在原子群而形成環狀配位基。L15 並不與L11 及L14 兩者鍵結形成環狀配位基。Y11 、Y12 、Y13 相互獨立表示連結基、單鍵、或者雙鍵。L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵表示單鍵或雙鍵。n11 表示0～4。In the formula (2), M 11 represents a metal ion, and L 11 , L 12 , L 13 , L 14 and L 15 each independently represent a ligand coordinated to M 11 . There is no further atomic group between L 11 and L 14 to form a cyclic ligand. L 15 is not bonded to both L 11 and L 14 to form a cyclic ligand. Y 11 , Y 12 and Y 13 independently represent a linking group, a single bond, or a double bond. The bond between L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L 14 represents a single bond or a double bond. n 11 represents 0 to 4.

較好的是上述電子傳輸性磷光發光材料為鉑錯合物。It is preferred that the above electron transporting phosphorescent material is a platinum complex.

較好的是以上述通式(1)所表示的含氮雜環化合物為以下述通式(3)所表示的含氮雜環化合物。The nitrogen-containing heterocyclic compound represented by the above formula (1) is preferably a nitrogen-containing heterocyclic compound represented by the following formula (3).

通式(3)中，A1 ～A3 、Ar1 、Ar2 、L1 以及L2 與上述通式(1)中同義。R'與上述通式(1)中的R同義。In the formula (3), A 1 to A 3 , Ar 1 , Ar 2 , L 1 and L 2 are synonymous with the above formula (1). R' is synonymous with R in the above formula (1).

較好的是以上述通式(1)所表示的含氮雜環化合物為以下述通式(4)所表示的含氮雜環化合物。The nitrogen-containing heterocyclic compound represented by the above formula (1) is preferably a nitrogen-containing heterocyclic compound represented by the following formula (4).

通式(4)中，A1 、A2 、Ar1 、Ar2 、L1 以及L2 與上述通式(1)中同義。R'、R"與上述通式(1)中的R同義，且相互可相同亦可不同。In the formula (4), A 1 , A 2 , Ar 1 , Ar 2 , L 1 and L 2 have the same meanings as in the above formula (1). R' and R" are synonymous with R in the above formula (1), and may be the same or different from each other.

較好的是在以上述通式(1)、(3)～(4)所表示的含氮雜環化合物中，上述L1 及L2 相互獨立為選自以下述化學式所表示的二價基組群中的基。In the nitrogen-containing heterocyclic compound represented by the above formulas (1) and (3) to (4), the above-mentioned L 1 and L 2 are each independently selected from a divalent group represented by the following chemical formula. The base in the group.

較好的是在以上述通式(1)、(3)～(4)所表示的含氮雜環化合物中，上述Ar1 及Ar2 的至少一者為以下述通式(5)～(14)所表示的基。In the nitrogen-containing heterocyclic compound represented by the above formulas (1) and (3) to (4), at least one of Ar 1 and Ar 2 is preferably a compound of the following formula (5) to (5). 14) The base indicated.

式中，R1 ～R92 相互獨立為氫原子、鹵素原子、經取代或未經取代的碳數1～20的烷基、經取代或未經取代的碳數1～20的烷氧基、經取代或未經取代的核碳數6～40的芳氧基、經取代或未經取代的核碳數12～80的二芳胺基、經取代或未經取代的核碳數6～40的芳基、經取代或未經取代的核碳數3～40的雜芳基、或者經取代或未經取代的核碳數18～120的二芳胺基芳基，L3 為選自由單鍵及以下述化學式所表示的二價基所組成組群中的基。In the formula, R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 80 carbon atoms, substituted or unsubstituted nucleocarbon number 6 to 40 An aryl group, a substituted or unsubstituted heteroaryl group having a core carbon number of 3 to 40, or a substituted or unsubstituted diarylaminoaryl group having a core number of 18 to 120, and L 3 is selected from the group consisting of A bond and a group in a group consisting of a divalent group represented by the following chemical formula.

較好的是上述電子傳輸性磷光發光材料包含以下述通式(15)所表示的部分結構。It is preferred that the electron transporting phosphorescent material contains a partial structure represented by the following formula (15).

通式(15)中，M21 表示金屬離子，Y21 表示連結基、單鍵或者雙鍵。Y22 、Y23 相互獨立表示單鍵或連結基。Q21 、Q22 相互獨立表示形成含氮雜環的原子群，由Q21 所形成的環與Y21 之間的鍵及由Q22 所形成的環與Y21 之間的鍵表示單鍵或雙鍵。X21 、X22 相互獨立表示氧原子、硫原子、經取代或未經取代的氮原子。R21 、R22 、R23 、R24 相互獨立表示氫原子或取代基，R21 及R22 以及R23 及R24 亦可分別鍵結而形成環。L25 表示配位在M21 上的配位基。n21 表示0～4的整數。In the formula (15), M 21 represents a metal ion, and Y 21 represents a linking group, a single bond or a double bond. Y 22 and Y 23 independently of each other represent a single bond or a linking group. Q 21 and Q 22 independently of each other represent a group of atoms forming a nitrogen-containing hetero ring, and a bond between a ring formed by Q 21 and Y 21 and a bond formed between Q 22 and Y 21 represents a single bond or Double key. X 21 and X 22 independently represent an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom. R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom or a substituent, and R 21 and R 22 and R 23 and R 24 may be bonded to each other to form a ring. L 25 represents a ligand coordinated to M 21 . n 21 represents an integer of 0 to 4.

較好的是包含四牙配位基的至少一種鉑錯合物來作為上述電子傳輸性磷光發光材料，該鉑錯合物包含以下述通式(16)所表示的部分結構。Preferred is at least one platinum complex containing a tetradentate ligand as the above electron transporting phosphorescent material, and the platinum complex comprises a partial structure represented by the following formula (16).

通式(16)中，Z1 表示以氮原子而配位在鉑上的含氮雜環。L1 表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。In the formula (16), Z 1 represents a nitrogen-containing hetero ring which is coordinated to platinum by a nitrogen atom. L 1 represents a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent.

較好的是包含以上述通式(16)所表示的部分結構的四牙配位基的鉑錯合物為以下述通式(17)所表示的鉑錯合物。It is preferred that the platinum complex containing a tetradentate ligand having a partial structure represented by the above formula (16) is a platinum complex represented by the following formula (17).

通式(17)中，Z1 及Z2 相互獨立表示以氮原子而配位在鉑上的含氮雜環。Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。L1 、L2 以及L3 相互獨立表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。In the formula (17), Z 1 and Z 2 each independently represent a nitrogen-containing hetero ring which is coordinated to platinum by a nitrogen atom. Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent.

較好的是以上述通式(17)所表示的鉑錯合物為以下述通式(18)所表示的鉑錯合物。It is preferred that the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (18).

通式(18)中，Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。L1 、L2 以及L3 相互獨立表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0～3的整數。In the formula (18), Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent. R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3.

較好的是以上述通式(17)所表示的鉑錯合物為以下述通式(19)所表示的鉑錯合物。It is preferred that the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (19).

通式(19)中，Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基。L1 、L2 、L3 、R1 、R3 、R4 、R2 、Ra 、Rb 、以及n、m與上述通式(18)中同義。In the formula (19), Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom. L 1 , L 2 , L 3 , R 1 , R 3 , R 4 , R 2 , R a , R b , and n, m are synonymous with the above formula (18).

較好的是以上述通式(19)所表示的鉑錯合物為以下述通式(20)所表示的化合物。It is preferred that the platinum complex represented by the above formula (19) is a compound represented by the following formula (20).

通式(20)中，L1 、L2 、L3 、R1 ～R4 、Ra 、Rb 、以及n、m與上述通式(18)中同義。R5 、R7 、R8 相互獨立表示氫原子或取代基，R6 表示取代基。In the formula (20), L 1 , L 2 , L 3 , R 1 to R 4 , R a , R b , and n, m are synonymous with the above formula (18). R 5 , R 7 and R 8 each independently represent a hydrogen atom or a substituent, and R 6 represents a substituent.

較好的是上述發光層含有電洞傳輸性主體材料。It is preferred that the light-emitting layer contains a hole transporting host material.

較好的是上述含有含氮雜環化合物的電子傳輸層含有還原性摻雜劑。較好的是上述還原性摻雜劑為選自由鹼金屬、鹼土金屬、稀土金屬、鹼金屬的氧化物、鹼金屬的鹵化物、鹼土金屬的氧化物、鹼土金屬的鹵化物、稀土金屬的氧化物、稀土金屬的鹵化物、鹼金屬的有機錯合物、鹼土金屬的有機錯合物以及稀土金屬的有機錯合物所組成組群中的至少一種。It is preferred that the electron transport layer containing the nitrogen-containing heterocyclic compound contains a reducing dopant. Preferably, the reducing dopant is selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, and a rare earth metal. At least one of a group consisting of a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal.

2.有機電場發光元件的構成要素2. Components of an organic electric field light-emitting element

其次，對構成本發明的發光元件的要素進行詳細說明。Next, the elements constituting the light-emitting element of the present invention will be described in detail.

(基板)(substrate)

本發明中使用的基板較好的是不會使自有機層發出的光散射或衰減的基板。該基板的具體例可舉出：釔穩定氧化鋯(yttrium stabilized zirconia，YSZ)、玻璃(glass)等的無機材料；聚對苯二甲酸乙二酯(polyethylene terephthalate)、聚鄰苯二甲酸丁二酯(polybutylene phthalate)、聚萘二甲酸乙二酯(polyethylene naphthalate)等的聚酯(polyester)，聚苯乙烯(polystyrene)、聚碳酸酯(polycarbonate)、聚醚碸(polyether sulfone)、聚芳酯(polyarylate)、聚醯亞胺(polyimide)、聚環烯烴(polycycloolefin)、降冰片烯樹脂(norbornene resin)以及聚(氯三氟乙烯)(poly(chlorotrifluoroethylene))等的有機材料。The substrate used in the present invention is preferably a substrate which does not scatter or attenuate light emitted from the organic layer. Specific examples of the substrate include inorganic materials such as yttrium stabilized zirconia (YSZ) and glass; polyethylene terephthalate and polybutylene phthalate; Polybutylene phthalate, polyethylene naphthalate, polyester, polystyrene, polycarbonate, polyether sulfone, polyarylate (polyarylate), polyimide, polycycloolefin, norbornene resin, and poly(chlorotrifluoroethylene) organic materials.

例如當使用玻璃作為基板時，為了減少來自玻璃的溶出離子，該玻璃的材質較好的是使用無鹼玻璃(nonalkali glass)。另外，當使用鈉鈣玻璃(soda lime glass)時，較好的是使用實施有二氧化矽(silica)等的阻隔塗佈(barrier coat)的玻璃。當使用有機材料時，較好的是耐熱性、尺寸穩定性、耐溶劑性、電氣絕緣性以及加工性優異。For example, when glass is used as the substrate, in order to reduce eluted ions from the glass, the material of the glass is preferably nonalkali glass. Further, when soda lime glass is used, it is preferred to use a glass which is subjected to barrier coating with silica or the like. When an organic material is used, it is preferably excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and processability.

基板的形狀、結構、大小等並無特別限制，可根據發光元件的用途、目的等進行適當選擇。通常，基板的形狀較好的是板狀。基板的結構可為單層結構，亦可為積層結構，而且，可由單個構件所形成，亦可由兩個以上的構件所形成。The shape, structure, size, and the like of the substrate are not particularly limited, and may be appropriately selected depending on the use, purpose, and the like of the light-emitting element. Generally, the shape of the substrate is preferably a plate shape. The structure of the substrate may be a single layer structure or a laminated structure, and may be formed by a single member or by two or more members.

基板可為無色透明，亦可為有色透明，就不會使自有機發光層發出的光散射或衰減等的方面而言，較好的是無色透明。The substrate may be colorless and transparent, or may be colored and transparent, and is preferably colorless and transparent in terms of scattering or attenuating light emitted from the organic light-emitting layer.

可在基板的表面或背面設置防透濕層(氣體阻隔層(gas barrier layer))。A moisture barrier layer (gas barrier layer) may be provided on the surface or the back surface of the substrate.

防透濕層(氣體阻隔層)的材料適宜使用氮化矽、氧化矽等的無機物。防透濕層(氣體阻隔層)例如可利用高頻濺鍍法(high frequency sputtering)等而形成。As the material of the moisture-proof layer (gas barrier layer), an inorganic substance such as tantalum nitride or ruthenium oxide is preferably used. The moisture-proof layer (gas barrier layer) can be formed, for example, by high frequency sputtering or the like.

當使用熱塑性基板時，亦可進一步視需要而設置硬塗層(hard coat)、底塗層(under coat)等。When a thermoplastic substrate is used, a hard coat, an under coat, or the like may be further provided as needed.

(陽極)(anode)

陽極通常只要具有作為對有機層供給電洞的電極的功能即可，該陽極的形狀、結構、大小等並無特別限制。可根據發光元件的用途、目的，自公知的電極材料中適當選擇。如上所述，陽極通常設為透明陽極。The anode usually has a function as an electrode for supplying a hole to the organic layer, and the shape, structure, size, and the like of the anode are not particularly limited. It can be suitably selected from well-known electrode materials according to the use and purpose of a light-emitting element. As mentioned above, the anode is typically set to be a transparent anode.

陽極的材料例如適宜舉出金屬、合金、金屬氧化物、導電性化合物、或者該些材料的混合物。上述陽極材料的具體例，可舉出：摻雜著銻或氟等的氧化錫(antimony doped tin oxide，ATO；fluorine doped tin oxide，FTO)、氧化錫、氧化鋅、氧化銦、氧化銦錫(indium tin oxide，ITO)、氧化鋅銦(indium zinc oxide，IZO)等的導電性金屬氧化物；金、銀、鉻、鎳等的金屬，以及該些金屬與導電性金屬氧化物的混合物或積層物；碘化銅、硫化銅等的無機導電性物質；聚苯胺、聚噻吩、聚吡咯等的有機導電性材料；以及該些有機導電性材料與ITO的積層物等。其中，較好的是導電性金屬氧化物，尤其就生產性、高導電性、透明性等方面而言，較好的是ITO。The material of the anode is preferably, for example, a metal, an alloy, a metal oxide, a conductive compound, or a mixture of these materials. Specific examples of the anode material include an antimony doped tin oxide (ATO) (fluorine doped tin oxide (FTO), tin oxide, zinc oxide, indium oxide, and indium tin oxide doped with antimony or fluorine (ATO; Indium tin oxide (ITO), conductive metal oxides such as indium zinc oxide (IZO); metals such as gold, silver, chromium, nickel, and mixtures or laminates of the metals and conductive metal oxides An inorganic conductive material such as copper iodide or copper sulfide; an organic conductive material such as polyaniline, polythiophene or polypyrrole; and a laminate of the organic conductive material and ITO. Among them, a conductive metal oxide is preferred, and ITO is preferred in terms of productivity, high electrical conductivity, transparency, and the like.

陽極例如可依照考慮到與構成陽極的材料的適應性而自下述方式中適當選擇的方法來形成於上述基板上，上述方式為：印刷方式、塗佈方式等的濕式方式；真空蒸鍍法(vacuum evaporation method)、濺鍍法(sputtering method)、離子電鍍法(ion plating method)等的物理方式；化學氣相沈積(chemical vapor deposition，CVD)、電漿CVD法(plasma chemical vapor deposition)等的化學方式等。例如當選擇ITO作為陽極的材料時，陽極的形成可依照直流或高頻濺鍍法、真空蒸鍍法、離子電鍍法等而進行。The anode can be formed on the substrate by, for example, a method appropriately selected from the following aspects in consideration of adaptability to a material constituting the anode, and the above-described manner is a wet method such as a printing method or a coating method; vacuum evaporation Physical methods such as vacuum evaporation method, sputtering method, ion plating method, etc.; chemical vapor deposition (CVD), plasma chemical vapor deposition (plasma chemical vapor deposition) Chemical methods, etc. For example, when ITO is selected as the material of the anode, the formation of the anode can be carried out in accordance with a direct current or high frequency sputtering method, a vacuum evaporation method, an ion plating method, or the like.

本發明的有機電場發光元件中，陽極的形成位置並無特別限制。可根據發光元件的用途、目的進行適當選擇，較好的是形成在上述基板上。在該情況下，陽極可形成在基板的其中一表面的全部上，亦可形成在該表面的一部分上。In the organic electroluminescence device of the present invention, the position at which the anode is formed is not particularly limited. It can be suitably selected according to the use and purpose of the light-emitting element, and it is preferable to form it on the said board|substrate. In this case, the anode may be formed on all of one surface of the substrate or may be formed on a portion of the surface.

另外，形成陽極時的圖案化(patterning)可藉由利用光微影(photolithography)等的化學蝕刻(etching)而進行，亦可藉由利用雷射(laser)等的物理蝕刻而進行。而且，可重疊罩幕(mask)後進行真空蒸鍍或濺鍍等而進行，亦可利用舉離法(lift-off method)或印刷法而進行。Further, patterning at the time of forming an anode can be performed by chemical etching using photolithography or the like, or by physical etching using a laser or the like. Further, it may be carried out by superposing a mask, vacuum vapor deposition, sputtering, or the like, or by a lift-off method or a printing method.

陽極的厚度可根據構成陽極的材料而進行適當選擇，無法一概規定，通常為10nm～50μm左右，較好的是50nm～20μm。The thickness of the anode can be appropriately selected depending on the material constituting the anode, and it is not always specified, and is usually about 10 nm to 50 μm, preferably 50 nm to 20 μm.

陽極的電阻值較好的是小於等於103 Ω/□，更好的是小於等於102 Ω/□。在陽極為透明的情況下，可為無色透明亦可為有色透明。為了自透明陽極側出射發光，該陽極的透射率較好的是大於等於60%，更好的是大於等於70%。The resistance value of the anode is preferably 10 3 Ω/□ or less, more preferably 10 2 Ω/□ or less. In the case where the anode is transparent, it may be colorless and transparent or colored and transparent. In order to emit light from the transparent anode side, the transmittance of the anode is preferably 60% or more, more preferably 70% or more.

另外，關於透明陽極，在澤田豐主編的「透明電極膜的新展開」CMC出版(1999)中有詳述，可將其中所記載的事項應用於本發明。當使用耐熱性低的塑膠(plastic)基材時，較好的是使用ITO或IZO而於150℃以下的低溫下成膜的透明陽極。In addition, the transparent anode is described in detail in "New Development of Transparent Electrode Film" edited by Sawada, CMC Publishing (1999), and the matters described therein can be applied to the present invention. When a plastic substrate having low heat resistance is used, a transparent anode formed by using ITO or IZO at a low temperature of 150 ° C or lower is preferred.

(陰極)(cathode)

陰極通常只要具有作為對有機層注入電子的電極的功能即可，該陰極的形狀、結構、大小等並無特別限制。可根據發光元件的用途、目的，自公知的電極材料中適當選擇。The cathode usually has a function as an electrode for injecting electrons into the organic layer, and the shape, structure, size, and the like of the cathode are not particularly limited. It can be suitably selected from well-known electrode materials according to the use and purpose of a light-emitting element.

構成陰極的材料例如可舉出金屬、合金、金屬氧化物、導電性化合物、該些材料的混合物等。上述陰極材料的具體例可舉出：鹼金屬(例如Li、Na、K、Cs等)、鹼土金屬(例如Mg、Ca等)、金、銀、鉛、鋁、鈉-鉀合金、鋰-鋁合金、鎂-銀合金、銦、以及鐿等的稀土金屬等。該些金屬可單獨使用一種，就同時實現穩定性與電子注入性的觀點而言，可適當地併用兩種以上。Examples of the material constituting the cathode include a metal, an alloy, a metal oxide, a conductive compound, a mixture of these materials, and the like. Specific examples of the cathode material include alkali metals (for example, Li, Na, K, and Cs), alkaline earth metals (for example, Mg, Ca, etc.), gold, silver, lead, aluminum, sodium-potassium alloy, and lithium-aluminum. Alloys, magnesium-silver alloys, indium, and rare earth metals such as ruthenium. These metals may be used singly or in combination of two or more kinds in view of achieving stability and electron injectability at the same time.

上述材料中，構成陰極的材料就電子注入性方面而言，較好的是鹼金屬或鹼土金屬，就保存穩定性優異的方面而言，較好的是以鋁為主體的材料。Among the above materials, the material constituting the cathode is preferably an alkali metal or an alkaline earth metal in terms of electron injectability, and is preferably a material mainly composed of aluminum in terms of excellent storage stability.

所謂以鋁為主體的材料，是指鋁單獨、鋁與0.01wt%(重量百分比)～10wt%的鹼金屬或鹼土金屬的合金、或者該些材料的混合物(例如鋰-鋁合金、鎂-鋁合金等)。The term "aluminum-based material" refers to an alloy of aluminum alone, aluminum with 0.01 wt% to 10 wt% of an alkali metal or alkaline earth metal, or a mixture of such materials (for example, lithium-aluminum alloy, magnesium-aluminum Alloy, etc.).

另外，關於陰極的材料，在日本專利特開平2-15595號公報、日本專利特開平5-121172號公報中進行了詳述，該些公報中記載的材料亦可應用於本發明。In addition, the material of the cathode is described in detail in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei.

對陰極的形成方法並無特別限制，可依照公知的方法進行。The method of forming the cathode is not particularly limited and can be carried out in accordance with a known method.

例如可依照考慮到與上述構成陰極的材料的適應性而自下述方式中適當選擇的方法來形成，上述方式為：印刷方式、塗佈方式等的濕式方式；真空蒸鍍法、濺鍍法、離子電鍍法等的物理方式；CVD、電漿CVD法等的化學方式等。例如當選擇金屬等作為陰極的材料時，將該材料的一種或者兩種以上同時或依次依照濺鍍法等來進行。For example, it can be formed by a method appropriately selected from the following aspects in consideration of the compatibility with the material constituting the cathode described above, which is a wet method such as a printing method or a coating method; vacuum evaporation method, sputtering Physical methods such as methods and ion plating methods; chemical methods such as CVD and plasma CVD. For example, when a metal or the like is selected as the material of the cathode, one or two or more of the materials are simultaneously or sequentially subjected to a sputtering method or the like.

形成陰極時的圖案化可藉由利用光微影等的化學蝕刻而進行，亦可藉由利用雷射等的物理蝕刻而進行。而且，可重疊罩幕後進行真空蒸鍍或濺鍍等而進行，亦可利用舉離法或印刷法而進行。The patterning at the time of forming the cathode can be performed by chemical etching using photolithography or the like, or by physical etching using laser or the like. Further, it may be carried out by vacuum deposition or sputtering after superimposing the mask, or by a lift-off method or a printing method.

本發明中，陰極形成位置並無特別限制，可形成在有機層上的全部上，亦可形成在該有機層的一部分上。In the present invention, the position at which the cathode is formed is not particularly limited and may be formed on all of the organic layer or may be formed on a part of the organic layer.

另外，在陰極與上述有機層之間亦可***厚度為0.1nm～5nm的由鹼金屬或鹼土金屬的氟化物、氧化物等所形成的介電質層(dielectric layer)。亦可將該介電質層視為一種電子注入層。介電質層例如可利用真空蒸鍍法、濺鍍法或者離子電鍍法等而形成。Further, a dielectric layer formed of a fluoride or an oxide of an alkali metal or an alkaline earth metal having a thickness of 0.1 nm to 5 nm may be interposed between the cathode and the organic layer. The dielectric layer can also be considered as an electron injecting layer. The dielectric layer can be formed, for example, by a vacuum deposition method, a sputtering method, an ion plating method, or the like.

陰極的厚度可根據構成陰極的材料而進行適當選擇，無法一概規定，通常為10nm～5μm左右，較好的是50nm～1μm。The thickness of the cathode can be appropriately selected depending on the material constituting the cathode, and it is not always specified, and is usually about 10 nm to 5 μm, preferably 50 nm to 1 μm.

另外，陰極可為透明，亦可為不透明。另外，透明的陰極可藉由使陰極的材料較薄地成膜為1nm～10nm的厚度，進而積層ITO或IZO等的透明導電性材料而形成。Alternatively, the cathode can be transparent or opaque. Further, the transparent cathode can be formed by laminating a material of the cathode to a thickness of 1 nm to 10 nm, and further laminating a transparent conductive material such as ITO or IZO.

(有機層)(organic layer)

對本發明中的有機層進行說明。The organic layer in the present invention will be described.

本發明的有機EL元件具有包含發光層的至少一層有機化合物層，上述發光層含有電子傳輸性磷光發光材料，且在上述發光層與陰極之間具有含有以通式(1)所表示的含氮雜環化合物的電子傳輸層。The organic EL device of the present invention has at least one organic compound layer containing a light-emitting layer containing an electron-transporting phosphorescent material and having a nitrogen-containing compound represented by the general formula (1) between the light-emitting layer and the cathode. An electron transport layer of a heterocyclic compound.

除發光層以外的其他有機層，如上所述可舉出電洞傳輸層、電子傳輸層、電荷阻擋層、電洞注入層、電子注入層等的各層。As the organic layer other than the light-emitting layer, as described above, each layer such as a hole transport layer, an electron transport layer, a charge block layer, a hole injection layer, and an electron injection layer may be mentioned.

本發明的有機EL元件中，構成有機層的各層可利用蒸鍍法或濺鍍法等的乾式製膜法、濕式塗佈方式、轉印法、印刷法、噴墨(ink-Jet)方式等的任一方法而適當地形成。In the organic EL device of the present invention, each of the layers constituting the organic layer can be a dry film forming method such as a vapor deposition method or a sputtering method, a wet coating method, a transfer method, a printing method, or an ink-jet method. It is formed as appropriate by any of the methods.

(發光層)(lighting layer)

有機發光層為具有如下功能的層，即，當電場施加時，自陽極、電洞注入層或者電洞傳輸層接收電洞，且自陰極、電子注入層或者電子傳輸層接收電子，提供電洞與電子的再結合的場所而使其發光。The organic light-emitting layer is a layer having a function of receiving a hole from an anode, a hole injection layer, or a hole transport layer when an electric field is applied, and receiving electrons from a cathode, an electron injection layer, or an electron transport layer to provide a hole It is illuminated by a place where it is recombined with electrons.

本發明中的發光層至少含有電子傳輸性磷光發光材料作為發光材料。較好的是電子傳輸性磷光發光材料為下述金屬錯合物的至少一種，該金屬錯合物具有三牙以上的配位基，且該配位基為鏈狀配位基並具有以下述通式(2)所表示的部分結構。The light-emitting layer in the present invention contains at least an electron-transporting phosphorescent material as a light-emitting material. Preferably, the electron-transporting phosphorescent material is at least one of the following metal complexes having a ligand of three or more teeth, and the ligand is a chain-like ligand and has the following Partial structure represented by the formula (2).

通式(2)中，M11 表示金屬離子，L11 、L12 、L13 、L14 、L15 相互獨立表示配位在M11 上的配位基。在L11 、L14 之間並不進一步存在原子群而形成環狀配位基。L15 並不與L11 及L14 兩者鍵結形成環狀配位基。Y11 、Y12 、Y13 相互獨立表示連結基、單鍵或者雙鍵。L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵表示單鍵或雙鍵。n11 表示0～4。In the formula (2), M 11 represents a metal ion, and L 11 , L 12 , L 13 , L 14 and L 15 each independently represent a ligand coordinated to M 11 . There is no further atomic group between L 11 and L 14 to form a cyclic ligand. L 15 is not bonded to both L 11 and L 14 to form a cyclic ligand. Y 11 , Y 12 and Y 13 independently represent a linking group, a single bond or a double bond. The bond between L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L 14 represents a single bond or a double bond. n 11 represents 0 to 4.

較好的是上述電子傳輸性磷光發光材料為鉑錯合物。It is preferred that the above electron transporting phosphorescent material is a platinum complex.

較好的是上述電子傳輸性磷光發光材料包含以下述通式(15)所表示的部分結構。It is preferred that the electron transporting phosphorescent material contains a partial structure represented by the following formula (15).

通式(15)中，M21 表示金屬離子，Y21 表示連結基、單鍵或者雙鍵。Y22 、Y23 相互獨立表示單鍵或連結基。Q21 、Q22 相互獨立表示形成含氮雜環的原子群，由Q21 所形成的環與Y21 之間的鍵及由Q22 所形成的環與Y21 之間的鍵表示單鍵或雙鍵。X21 、X22 相互獨立表示氧原子、硫原子、經取代或未經取代的氮原子。R21 、R22 、R23 、R24 相互獨立表示氫原子或取代基，R21 及R22 以及R23 及R24 亦可分別鍵結而形成環。L25 表示配位在M21 上的配位基。n21 表示0～4的整數。In the formula (15), M 21 represents a metal ion, and Y 21 represents a linking group, a single bond or a double bond. Y 22 and Y 23 independently of each other represent a single bond or a linking group. Q 21 and Q 22 independently of each other represent a group of atoms forming a nitrogen-containing hetero ring, and a bond between a ring formed by Q 21 and Y 21 and a bond formed between Q 22 and Y 21 represents a single bond or Double key. X 21 and X 22 independently represent an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom. R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom or a substituent, and R 21 and R 22 and R 23 and R 24 may be bonded to each other to form a ring. L 25 represents a ligand coordinated to M 21 . n 21 represents an integer of 0 to 4.

較好的是上述電子傳輸性磷光發光材料為四牙配位基的鉑錯合物的至少一種，該鉑錯合物包含以下述通式(16)所表示的部分結構。It is preferable that the electron-transporting phosphorescent material is at least one of platinum-based complexes having a tetradentate ligand, and the platinum complex comprises a partial structure represented by the following formula (16).

通式(16)中，Z1 表示以氮原子而配位在鉑上的含氮雜環。L1 表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。In the formula (16), Z 1 represents a nitrogen-containing hetero ring which is coordinated to platinum by a nitrogen atom. L 1 represents a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent.

較好的是包含以上述通式(16)所表示的部分結構的四牙配位基的鉑錯合物為以下述通式(17)所表示的鉑錯合物。It is preferred that the platinum complex containing a tetradentate ligand having a partial structure represented by the above formula (16) is a platinum complex represented by the following formula (17).

通式(17)中，Z1 及Z2 相互獨立表示以氮原子而配位在鉑上的含氮雜環。Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。L1 、L2 以及L3 相互獨立表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。In the formula (17), Z 1 and Z 2 each independently represent a nitrogen-containing hetero ring which is coordinated to platinum by a nitrogen atom. Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent.

較好的是以上述通式(17)所表示的鉑錯合物為以下述通式(18)所表示的鉑錯合物。It is preferred that the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (18).

通式(18)中，Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。L1 、L2 以及L3 相互獨立表示單鍵或連結基。R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基。Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0～3的整數。In the formula (18), Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group. R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent. R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3.

較好的是以上述通式(17)所表示的鉑錯合物為以下述通式(19)所表示的鉑錯合物。It is preferred that the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (19).

通式(19)中，Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基。L1 、L2 、L3 、R1 、R3 、R4 、R2 、Ra 、Rb 、以及n、m與上述通式(18)中同義。In the formula (19), Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom. L 1 , L 2 , L 3 , R 1 , R 3 , R 4 , R 2 , R a , R b , and n, m are synonymous with the above formula (18).

較好的是以上述通式(19)所表示的鉑錯合物為以下述通式(20)所表示的化合物。It is preferred that the platinum complex represented by the above formula (19) is a compound represented by the following formula (20).

通式(20)中，L1 、L2 、L3 、R1 ～R4 、Ra 、Rb 、以及n、m與上述通式(18)中同義。R5 、R7 、R8 相互獨立表示氫原子或取代基，R6 表示取代基。In the formula (20), L 1 , L 2 , L 3 , R 1 to R 4 , R a , R b , and n, m are synonymous with the above formula (18). R 5 , R 7 and R 8 each independently represent a hydrogen atom or a substituent, and R 6 represents a substituent.

本發明中所使用的鉑錯合物在發光層中的含量較好的是大於等於0.1wt%且小於等於50wt%，更好的是大於等於0.2wt%且小於等於30wt%，進而較好的是大於等於0.3wt%且小於等於20wt%，最好的是大於等於0.5wt%且小於等於10wt%。The content of the platinum complex used in the present invention in the light-emitting layer is preferably 0.1% by weight or more and 50% by weight or less, more preferably 0.2% by weight or more and 30% by weight or less, and further preferably It is 0.3% by weight or more and 20% by weight or less, preferably 0.5% by weight or more and 10% by weight or less.

較好的是本發明中的發光層含有電洞傳輸性主體材料。亦可更含有電子傳輸性主體材料。It is preferred that the light-emitting layer of the present invention contains a hole transporting host material. It may also contain an electron transporting host material.

所謂主體材料，是在發光層中主要承擔電荷的注入、傳輸的化合物，且該主體材料本身為實質上不發光的化合物。本說明書中，所謂「實質上不發光」，是指來自該實質上不發光的化合物的發光量較好的是小於等於元件整體的總發光量的5%，更好的是小於等於3%，進而較好的是小於等於1%。The host material is a compound that mainly bears charge injection and transport in the light-emitting layer, and the host material itself is a compound that does not substantially emit light. In the present specification, the term "substantially does not emit light" means that the amount of light emitted from the substantially non-light-emitting compound is preferably 5% or less, more preferably 3% or less, based on the total amount of light emitted from the entire device. Further preferably, it is 1% or less.

發光層中的主體材料的濃度並無特別限定，較好的是於發光層中為主成分(含量最多的成分)，更好的是大於等於50wt%且小於等於99.9wt%，進而較好的是大於等於70wt%且小於等於99.8wt%，最好的是大於等於80wt%且小於等於99.7wt%。The concentration of the host material in the light-emitting layer is not particularly limited, and is preferably a main component (a component having the highest content) in the light-emitting layer, more preferably 50% by weight or more and 99.9% by weight or less, and further preferably It is 70% by weight or more and 99.8% by weight or less, preferably 80% by weight or more and 99.7% by weight or less.

主體材料的玻璃轉移點較好的是大於等於100℃且小於等於500℃，更好的是大於等於110℃且小於等於300℃，進而較好的是大於等於120℃且小於等於250℃。The glass transition point of the host material is preferably 100 ° C or more and 500 ° C or less, more preferably 110 ° C or more and 300 ° C or less, and further preferably 120 ° C or more and 250 ° C or less.

＜電子傳輸性磷光發光材料＞<Electron transporting phosphorescent materials>

對本發明中的電子傳輸性磷光發光材料進行更詳細地說明。The electron-transporting phosphorescent material of the present invention will be described in more detail.

本發明中的電子傳輸性磷光發光材料較好的是以下詳述的以通式(2)所表示的金屬錯合物。The electron transporting phosphorescent material in the present invention is preferably a metal complex represented by the formula (2) described in detail below.

通式(2)中，M11 表示金屬離子，L11 ～L15 分別表示配位在M11 上的配位基。在L11 與L14 之間亦可進一步存在原子群而形成環狀配位基。L15 亦可與L11 及L14 兩者鍵結形成環狀配位基。Y11 、Y12 、Y13 分別表示連結基、單鍵或者雙鍵。而且，當Y11 、Y12 或者Y13 為連結基時，L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵分別獨立表示單鍵或雙鍵。n11 表示0～4。M11 與L11 ～L15 的鍵可分別為配位鍵、離子鍵、共價鍵的任一種。In the formula (2), M 11 represents a metal ion, and L 11 to L 15 each represent a ligand coordinated to M 11 . Further, an atomic group may be present between L 11 and L 14 to form a cyclic ligand. L 15 may also be bonded to both L 11 and L 14 to form a cyclic ligand. Y 11 , Y 12 and Y 13 each represent a linking group, a single bond or a double bond. Moreover, when Y 11 , Y 12 or Y 13 is a linking group, L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L The keys between 14 independently represent single or double keys. n 11 represents 0 to 4. The bond of M 11 and L 11 to L 15 may be any of a coordinate bond, an ionic bond, and a covalent bond, respectively.

對以通式(2)所表示的化合物進行詳細說明。The compound represented by the formula (2) will be described in detail.

通式(2)中，M11 表示金屬離子。金屬離子並無特別限定，較好的是二價或三價的金屬離子。二價或三價的金屬離子較好的是鉑離子、銥離子、錸離子、鈀離子、銠離子、釕離子、銅離子、銪離子、釓離子、鋱離子，更好的是鉑離子、銥離子、銪離子，進而較好的是鉑離子、銥離子，尤其好的是鉑離子。In the formula (2), M 11 represents a metal ion. The metal ion is not particularly limited, and a divalent or trivalent metal ion is preferred. The divalent or trivalent metal ion is preferably a platinum ion, a cerium ion, a cerium ion, a palladium ion, a cerium ion, a cerium ion, a copper ion, a cerium ion, a cerium ion, a cerium ion, more preferably a platinum ion or a cerium ion. The ion and the cerium ion are further preferably a platinum ion or a cerium ion, and particularly preferably a platinum ion.

通式(2)中，L11 、L12 、L13 以及L14 分別獨立表示配位在M11 上的配位基。包含於L11 、L12 、L13 以及L14 中且配位在M11 上的原子，較好的是氮原子、氧原子、硫原子、碳原子或者磷原子，更好的是氮原子、氧原子、硫原子或者碳原子，進而較好的是氮原子、氧原子或者碳原子。In the formula (2), L 11 , L 12 , L 13 and L 14 each independently represent a ligand coordinated to M 11 . The atom contained in L 11 , L 12 , L 13 and L 14 and coordinated to M 11 is preferably a nitrogen atom, an oxygen atom, a sulfur atom, a carbon atom or a phosphorus atom, more preferably a nitrogen atom, An oxygen atom, a sulfur atom or a carbon atom is further preferably a nitrogen atom, an oxygen atom or a carbon atom.

由M11 與L11 、L12 、L13 以及L14 所分別形成的鍵可分別獨立為共價鍵，可為離子鍵，亦可為配位鍵。所謂本發明中的配位基，為了便於說明，不僅指配位鍵，亦可用於由其他的離子鍵、共價鍵而形成的情況。The bonds formed by M 11 and L 11 , L 12 , L 13 and L 14 respectively may be independently a covalent bond, and may be an ionic bond or a coordinate bond. The ligand in the present invention may be used not only for a coordinate bond but also for forming another ionic bond or a covalent bond for convenience of explanation.

由L11 、Y12 、L12 、Y1l 、L13 、Y13 以及L14 所形成的配位基較好的是陰離子性配位基(至少一個陰離子與金屬鍵結而成的配位基)。陰離子性配位基中的陰離子數較好的是1～3，更好的是1、2，進而較好的是2。The ligand formed by L 11 , Y 12 , L 12 , Y 1l , L 13 , Y 13 and L 14 is preferably an anionic ligand (at least one anion-metal-bonded ligand) ). The number of anions in the anionic ligand is preferably from 1 to 3, more preferably 1, 2, and still more preferably 2.

以碳原子而配位在M11 上的L11 、L12 、L13 以及L14 並無特別限定，可分別獨立舉出：亞胺基配位基、芳香族碳環配位基(例如苯(benzene)配位基、萘(naphthalene)配位基、蒽(anthracene)配位基、菲(phenanthracene)配位基等)、雜環配位基(例如呋喃(furan)配位基、噻吩(thiophene)配位基、吡啶(pyridine)配位基、吡嗪(pyrazine)配位基、嘧啶(pyrimidine)配位基、噻唑(thiazole)配位基、噁唑(oxazole)配位基、吡咯(pyrrole)配位基、咪唑(imidazole)配位基、吡唑(pyrazole)配位基、以及含有該些配位基的稠環(例如喹啉(quinoline)配位基、苯幷噻唑(benzothiazole)配位基等)及該些稠環的互變異構物(tautomer))。L 11 , L 12 , L 13 and L 14 which are coordinated to each other on the carbon atom by M 11 are not particularly limited, and may independently be an imino ligand or an aromatic carbocyclic ligand (for example, benzene). (benzene) ligand, naphthalene ligand, anthracene ligand, phenanthracene ligand, etc., heterocyclic ligand (eg furan ligand, thiophene ( Thiophene) ligand, pyridine ligand, pyrazine ligand, pyrimidine ligand, thiazole ligand, oxazole ligand, pyrrole Pyrrole) a ligand, an imidazole ligand, a pyrazole ligand, and a fused ring containing such a ligand (eg, a quinoline ligand, benzothiazole) A ligand, etc.) and a tautomer of the fused ring.

以氮原子而配位在M11 上的L11 、L12 、L13 以及L14 並無特別限定，可分別獨立舉出：含氮雜環配位基(例如吡啶配位基、吡嗪配位基、嘧啶配位基、噠嗪(pyridazine)配位基、三嗪(triazine)配位基、噻唑配位基、噁唑配位基、吡咯配位基、咪唑配位基、吡唑配位基、***(triazole)配位基、噁二唑(oxadiazole)配位基、噻二唑(thiadiazole)配位基、以及含有該些配位基的稠環(例如喹啉配位基、苯幷噁唑配位基、苯幷咪唑配位基等)及該些稠環的互變異構物(另外，本發明中除通常的異構物以外，將如下的例子亦定義為互變異構物。例如將日本專利特開2007-103493化合物編號「化24」中記載的例示化合物(24)的五員雜環配位基、化合物編號「化28」中記載的例示化合物(64)的末端五員雜環配位基、化合物編號「化37」中記載的例示化合物(145)的五員雜環配位基亦定義為吡咯互變異構物)等；胺基配位基(烷胺基配位基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出甲胺基等)、芳胺基配位基(例如可舉出苯基胺基等)、醯基胺基配位基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯基胺基、苯甲醯基胺基等)、烷氧基羰基胺基配位基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～12，例如可舉出甲氧基羰基胺基等)、芳氧基羰基胺基配位基(較好的是碳數為7～30，更好的是碳數為7～20，尤其好的是碳數為7～12，例如可舉出苯氧基羰基胺基等)、磺醯基胺基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲磺醯基胺基、苯磺醯基胺基等)、亞胺基配位基等)。該些配位基亦可經進一步取代。L 11 , L 12 , L 13 and L 14 which are coordinated to M 11 with a nitrogen atom are not particularly limited, and may independently be a nitrogen-containing heterocyclic ligand (for example, a pyridine ligand or a pyrazine). Site group, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole a terminal group, a triazole ligand, an oxadiazole ligand, a thiadiazole ligand, and a fused ring containing the ligand (eg, a quinoline ligand, a benzoxazole ligand, a benzoimidazole ligand, etc.) and a tautomer of the fused ring (in addition, in the present invention, in addition to the usual isomer, the following example is also defined as tautomerism For example, the end of the exemplified compound (64) of the exemplified compound (24) described in the compound number "24" of the Japanese Patent Publication No. 2007-103493, and the compound compound (64) described in the compound number "Chem. 28". The five-membered heterocyclic ligand and the five-membered heterocyclic ligand of the exemplified compound (145) described in the compound number "Chemical 37" are also defined as pyrrolemutation. An amine ligand; an alkylamino ligand (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 10, For example, a methylamino group or the like, an arylamine group (for example, a phenylamine group), and a mercaptoamine group (preferably, a carbon number of 2 to 30) is more preferable. The carbon number is 2 to 20, particularly preferably the carbon number is 2 to 10, and examples thereof include an ethyl hydrazino group and a benzhydrylamino group, and an alkoxycarbonylamino group (preferably). The carbon number is 2 to 30, more preferably the carbon number is 2 to 20, particularly preferably the carbon number is 2 to 12, for example, a methoxycarbonylamino group, etc., and an aryloxycarbonylamino group. a ligand (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, for example, a phenoxycarbonylamino group) a sulfonylamino group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 12, for example, a methylsulfonyl group; An amine group, a phenylsulfonylamino group, etc., an imido ligand, etc.). These ligands may also be further substituted.

以氧原子而配位在M11 上的L11 、L12 、L13 以及L14 並無特別限定，可分別獨立舉出：烷氧基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲氧基、乙氧基、丁氧基、2-乙基己氧基等)、芳氧基配位基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯氧基、1-萘氧基、2-萘氧基等)、雜環氧基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶氧基、吡嗪氧基、嘧啶氧基、喹啉氧基等)、醯氧基配位基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯氧基、苯甲醯氧基等)、矽烷氧基配位基(較好的是碳數為3～40，更好的是碳數為3～30，尤其好的是碳數為3～24，例如可舉出三甲基矽烷氧基、三苯基矽烷氧基等)、羰基配位基(例如酮配位基、酯配位基、醯胺基配位基等)、醚配位基(例如二烷基醚配位基、二芳基醚配位基、呋喃基配位基等)等。該些配位基亦可經進一步取代。L 11 , L 12 , L 13 and L 14 which are coordinated to each other on the M 11 by an oxygen atom are not particularly limited, and each of them may independently be an alkoxy ligand (preferably, the carbon number is from 1 to 30). More preferably, the carbon number is from 1 to 20, and particularly preferably, the carbon number is from 1 to 10, and examples thereof include a methoxy group, an ethoxy group, a butoxy group, a 2-ethylhexyloxy group, and the like. The oxy ligand (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number of 6 to 12, and examples thereof include a phenoxy group and a 1-naphthalene group. Oxyl group, 2-naphthyloxy group, etc.), heterocyclic oxy ligand (preferably, the number of carbon atoms is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 20 carbon atoms). 12, for example, a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group, a quinolyloxy group or the like), a decyloxy ligand (preferably, the carbon number is 2 to 30, more preferably the carbon number). 2 to 20, particularly preferably a carbon number of 2 to 10, for example, an ethoxycarbonyl group, a benzhydryloxy group or the like, and a decyloxy ligand (preferably, the carbon number is 3 to 40). More preferably, the carbon number is from 3 to 30, and particularly preferably, the carbon number is from 3 to 24, and examples thereof include trimethyldecyloxy group and triphenylsulfonyloxy group. Etc., a carbonyl ligand (eg, a ketone ligand, an ester ligand, a guanamine ligand, etc.), an ether ligand (eg, a dialkyl ether ligand, a diaryl ether ligand, Furanyl ligand, etc.). These ligands can also be further substituted.

以硫原子而配位在M11 上的L11 、L12 、L13 以及L14 並無特別限定，可分別獨立舉出：烷硫基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲硫基、乙硫基等)、芳硫基配位基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯硫基等)、雜環硫基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶硫基、2-苯幷咪唑硫基、2-苯幷噁唑硫基、2-苯幷噻唑硫基等)、硫羰基配位基(例如硫酮配位基、硫酯配位基等)、或者硫醚配位基(例如二烷基硫醚配位基、二芳基硫醚配位基、硫基呋喃基配位基等)等。該些配位基亦可經進一步取代。L 11 , L 12 , L 13 and L 14 which are coordinated to M 11 by a sulfur atom are not particularly limited, and each of them may be independently an alkylthio ligand (preferably, the carbon number is from 1 to 30). More preferably, the carbon number is from 1 to 20, particularly preferably from 1 to 12 carbon atoms, for example, a methylthio group or an ethylthio group, and an arylthio group (preferably a carbon number). It is 6 to 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, a phenylthio group, etc., a heterocyclic thiol ligand (preferably carbon) The number is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, and examples thereof include pyridylthio group, 2-phenylimidazoliumthio group, and 2-benzoxazole. a thio group, a 2-phenylhydrazinylthio group or the like, a thiocarbonyl ligand (for example, a thiol ligand, a thioester ligand, etc.), or a thioether ligand (for example, a dialkyl sulfide ligand) , a diaryl sulfide ligand, a thiofuranyl ligand, etc.). These ligands can also be further substituted.

以磷原子而配位在M11 上的L11 、L12 、L13 以及L14 並無特別限定，可分別獨立舉出二烷基膦基配位基、二芳基膦基配位基、三烷基膦配位基、三芳基膦配位基、phosphinine配位基等。該些配位基亦可經進一步取代。L 11 , L 12 , L 13 and L 14 which are coordinated to the M 11 by a phosphorus atom are not particularly limited, and a dialkylphosphino ligand or a diarylphosphino ligand may be independently mentioned. a trialkylphosphine ligand, a triarylphosphine ligand, a phosphinine ligand, and the like. These ligands can also be further substituted.

L11 及Ll4 較好的是分別獨立為：芳香族碳環配位基、烷氧基配位基、芳氧基配位基、醚配位基、烷硫基配位基、芳硫基配位基、烷胺基配位基、芳胺基配位基、醯基胺基配位基、含氮雜環配位基(例如吡啶配位基、吡嗪配位基、嘧啶配位基、噠嗪配位基、三嗪配位基、噻唑配位基、噁唑配位基、吡咯配位基、咪唑配位基、吡唑配位基、***配位基、噁二唑配位基、噻二唑配位基、或者含有該些配位基的稠環配位體(例如喹啉配位基、喹噁啉(quinoxaline)配位基、酞嗪(phthalazine)配位基、苯幷噁唑配位基、苯幷咪唑配位基等)或該些稠環配位體的互變異構物等)，更好的是芳香族碳環配位基、芳氧基配位基、芳硫基配位基、芳胺基配位基、以及吡啶配位基、吡嗪配位基、吡唑配位基、咪唑配位基、或者含有該些配位基的稠環配位體(例如喹啉配位基、喹噁啉配位基、酞嗪配位基、苯幷咪唑配位基等)或該些稠環配位體的互變異構物，進而較好的是芳香族碳環配位基、芳氧基配位基、芳硫基配位基、芳胺基配位基、以及吡啶配位基、吡嗪配位基、吡唑配位基、咪唑配位基、或者含有該些配位基的稠環配位體，尤其好的是芳香族碳環配位基、芳氧基配位基、以及吡啶配位基、吡嗪配位基、吡唑配位基、咪唑配位基、或者含有該些配位基的稠環配位體。L 11 and L l4 are preferably independently: an aromatic carbocyclic ligand, an alkoxy ligand, an aryloxy ligand, an ether ligand, an alkylthio ligand, an arylthio group. Ligand, alkylamino ligand, arylamine ligand, mercaptoamine ligand, nitrogen-containing heterocyclic ligand (eg pyridine ligand, pyrazine ligand, pyrimidine ligand) , pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxadiazole a thiodiazole ligand, or a fused ring ligand containing the ligand (eg, a quinoline ligand, a quinoxaline ligand, a phthalazine ligand, a benzoxazole ligand, a benzoimidazole ligand, or the like, or a tautomer of the fused ring ligand, etc.), more preferably an aromatic carbocyclic ligand or an aryloxy ligand , an arylthio ligand, an arylamine ligand, and a pyridine ligand, a pyrazine ligand, a pyrazole ligand, an imidazole ligand, or a fused ring coordination containing the ligand Body (eg quinoline ligand, quinoxaline coordination) , a pyridazine ligand, a benzoimidazole ligand, etc.) or a tautomer of the fused ring ligand, and more preferably an aromatic carbocyclic ligand, an aryloxy ligand, or an aromatic a thio-based ligand, an arylamine-based ligand, and a pyridine ligand, a pyrazine ligand, a pyrazole ligand, an imidazole ligand, or a fused ring ligand containing the ligand, Particularly preferred are aromatic carbocyclic ligands, aryloxy ligands, and pyridine ligands, pyrazine ligands, pyrazole ligands, imidazole ligands, or those containing such ligands. A fused ring ligand.

L12 及L13 較好的是分別獨立為與M11 形成配位鍵的配位基，與M11 形成配位鍵的配位基較好的是吡啶環、吡嗪環、嘧啶環、三嗪環、噻唑環、噁唑環、吡咯環、***環、以及含有該些配位基的稠環(例如喹啉環、喹噁啉配位基、酞嗪配位基、苯幷噁唑環、苯幷咪唑環、假吲哚(indolenine)環等)及該些稠環的互變異構物，更好的是吡啶環、吡嗪環、嘧啶環、吡咯環、以及含有該些配位基的稠環(例如喹啉環、喹噁啉環、酞嗪環、吲哚環等)及該些稠環的互變異構物，進而較好的是吡啶環、吡嗪環、嘧啶環、以及含有該些配位基的稠環(例如喹啉環等)，尤其好的是吡啶環及含有吡啶環的稠環(例如喹啉環等)。L 12 and L 13 preferably is a ligand and M 11 are independently forming a coordination bond with the ligand forming a coordination bond M 11 is preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, three a azine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, and a fused ring containing the ligand (for example, a quinoline ring, a quinoxaline ligand, a pyridazine ligand, a benzoxazole) a ring, a benzoimidazole ring, an indolenine ring, etc.) and a tautomer of the fused ring, more preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrrole ring, and the like a fused ring of a group (for example, a quinoline ring, a quinoxaline ring, a pyridazine ring, an anthracene ring, etc.) and a tautomer of the fused ring, and more preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, And a fused ring containing such a ligand (for example, a quinoline ring or the like), and particularly preferably a pyridine ring and a fused ring containing a pyridine ring (for example, a quinoline ring or the like).

通式(2)中，L15 表示配位在M11 上的配位基。L15 較好的是單牙至四牙的配位基，更好的是單牙至四牙的陰離子性配位基。單牙至四牙的陰離子性配位基並無特別限定，較好的是鹵素配位基，1,3-二酮配位基(例如乙醯丙酮配位基等)，含有吡啶配位基的單陰離子性雙牙配位基(例如吡啶甲酸(picolinic acid)配位基、2-(2-羥苯基)-吡啶配位基等)，由L11 、Y12 、L12 、Y11 、L13 、Y13 、L14 所形成的四牙配位基；更好的是1,3-二酮配位基(例如乙醯丙酮配位基等)，含有吡啶配位基的單陰離子性雙牙配位基(例如吡啶甲酸配位基、2-(2-羥苯基)-吡啶配位基等)，由L11 、Y12 、L12 、Y11 、L13 、Y13 、L14 所形成的四牙配位基；進而較好的是1,3-二酮配位基(例如乙醯丙酮配位基等)、含有吡啶配位基的單陰離子性雙牙配位基(例如吡啶甲酸配位基、2-(2-羥苯基)-吡啶配位基等)，尤其好的是1,3-二酮配位基(例如乙醯丙酮配位基等)。配位點(coordination site)的數量及配位基的數量不超過金屬的配位數。其中，L15 並不與L11 及L14 兩者鍵結形成環狀配位基。In the formula (2), L 15 represents a ligand coordinated to M 11 . L 15 is preferably a mono to tetradentate ligand, more preferably an anionic ligand from a single tooth to a tetradentate. The anionic ligand of the single to tetradentate is not particularly limited, and a halogen ligand, a 1,3-diketone ligand (for example, an acetamidine ligand, etc.), and a pyridine ligand are preferable. Monoanionic bidentate ligand (for example, picolinic acid ligand, 2-(2-hydroxyphenyl)-pyridine ligand, etc.), from L 11 , Y 12 , L 12 , Y 11 a tetradentate ligand formed by L 13 , Y 13 , L 14 ; more preferably a 1,3-diketone ligand (e.g., an acetone acetone ligand, etc.), a monoanion containing a pyridine ligand a bidentate ligand (for example, a picolinic acid ligand, a 2-(2-hydroxyphenyl)-pyridine ligand, etc.), which is composed of L 11 , Y 12 , L 12 , Y 11 , L 13 , Y 13 , a tetradentate ligand formed by L 14 ; further preferably a 1,3-diketone ligand (e.g., an acetone acetone ligand, etc.), a monoanionic bidentate ligand having a pyridine ligand (e.g., a picolinic acid ligand, a 2-(2-hydroxyphenyl)-pyridine ligand, etc.), particularly preferably a 1,3-diketone ligand (e.g., an acetoacetone ligand, etc.). The number of coordination sites and the number of ligands do not exceed the coordination number of the metal. Wherein L 15 is not bonded to both L 11 and L 14 to form a cyclic ligand.

通式(2)中，Y11 、Y12 以及Y13 分別獨立表示連結基、單鍵或者雙鍵。連結基並無特別限定，例如較好的是含有選自碳原子、氮原子、氧原子、硫原子、矽原子、磷原子中的原子而構成的連結基。此種連結基的具體例例如可舉出下述連結基。In the formula (2), Y 11 , Y 12 and Y 13 each independently represent a linking group, a single bond or a double bond. The linking group is not particularly limited, and for example, a linking group containing an atom selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom or a phosphorus atom is preferred. Specific examples of such a linking group include the following linking groups.

另外，當Y11 、Y12 或者Y13 為連結基時，L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵分別獨立表示單鍵或雙鍵。In addition, when Y 11 , Y 12 or Y 13 is a linking group, L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L The keys between 14 independently represent single or double keys.

Y11 、Y12 以及Y13 較好的是分別獨立為單鍵、雙鍵、羰基連結基、伸烷基連結基、伸烯基、胺基連結基。Y11 更好的是單鍵、伸烷基、胺基連結基，進而較好的是伸烷基。Y12 及Y13 更好的是單鍵、伸烯基，進而較好的是單鍵。Y 11 , Y 12 and Y 13 are preferably each independently a single bond, a double bond, a carbonyl linking group, an alkylene group, an alkenyl group or an amine group. More preferably, Y 11 is a single bond, an alkylene group, an amine group, and more preferably an alkyl group. Y 12 and Y 13 are more preferably a single bond or an extended alkenyl group, and more preferably a single bond.

由Y12 、L11 、L12 以及M11 所形成的環，由Y11 、L12 、L13 以及M11 所形成的環，由Y13 、L13 、L14 以及M11 所形成的環分別較好的是環員數為4～10，更好的是環員數為5～7，進而較好的是環員數為5或6。a ring formed of Y 12 , L 11 , L 12 , and M 11 , a ring formed of Y 11 , L 12 , L 13 , and M 11 , a ring formed of Y 13 , L 13 , L 14 , and M 11 Preferably, the ring number is 4 to 10, and more preferably the ring number is 5 to 7, and further preferably the ring number is 5 or 6.

通式(2)中，n11 表示0～4。當M11 為配位數為4的金屬時，n11 為0，當M11 為配位數為6的金屬時，n11 較好的是1、2，更好的是1。當M11 的配位數為6且n11 為1時，L15 表示雙牙配位基，當M11 的配位數為6且n11 為2時，L15 表示單牙配位基。當M11 為配位數為8的金屬時，n11 較好的是1～4，更好的是1、2，更好的是1。當M11 的配位數為8且n11 為1時，L15 表示四牙配位基，當M11 的配位數為8且n11 為2時，L15 表示雙牙配位基。當n11 為多個時，多個L15 可相同亦可不同。In the formula (2), n 11 represents 0 to 4. When M 11 is a metal having a coordination number of 4, n 11 is 0, and when M 11 is a metal having a coordination number of 6, n 11 is preferably 1, 2, more preferably 1. When the coordination number of M 11 is 6 and n 11 is 1, L 15 represents a bidentate ligand, and when the coordination number of M 11 is 6 and n 11 is 2, L 15 represents a monodentate ligand. When M 11 is a metal having a coordination number of 8, n 11 is preferably from 1 to 4, more preferably 1, 2, more preferably 1. When the coordination number of M 11 is 8 and n 11 is 1, L 15 represents a tetradentate ligand, and when the coordination number of M 11 is 8 and n 11 is 2, L 15 represents a bidentate ligand. When n 11 is plural, a plurality of L 15 may be the same or different.

以上述通式(2)所表示的化合物的較佳形態為以下所舉出的以通式(15)、通式(15-2)、通式(15-3)、通式(15-4)以及通式(15-5)所表示的各化合物。Preferred examples of the compound represented by the above formula (2) are the following formula (15), formula (15-2), formula (15-3), and formula (15-4). And each compound represented by the formula (15-5).

對以通式(15)所表示的化合物進行說明。The compound represented by the formula (15) will be described.

通式(15)中，M21 表示金屬離子，Y21 表示連結基、單鍵或者雙鍵。Y22 、Y23 分別表示單鍵或連結基。Q21 、Q22 分別表示形成含氮雜環的原子群，由Q21 所形成的環與Y21 之間的鍵及由Q22 所形成的環與Y21 之間的鍵表示單鍵或雙鍵。X21 、X22 分別獨立表示氧原子、硫原子、經取代或未經取代的氮原子。R21 、R22 、R23 以及R24 分別獨立表示氫原子或取代基，R21 及R22 以及R23 及R24 亦可分別鍵結而形成環。L25 表示配位在M21 上的配位基。n21 表示0～4的整數。In the formula (15), M 21 represents a metal ion, and Y 21 represents a linking group, a single bond or a double bond. Y 22 and Y 23 each represent a single bond or a linking group. Q 21 and Q 22 respectively represent a group of atoms forming a nitrogen-containing hetero ring, and a bond between a ring formed by Q 21 and Y 21 and a bond formed between Q 22 and Y 21 represent a single bond or a double bond. key. X 21 and X 22 each independently represent an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom. R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom or a substituent, and R 21 and R 22 and R 23 and R 24 may be bonded to each other to form a ring. L 25 represents a ligand coordinated to M 21 . n 21 represents an integer of 0 to 4.

對通式(15)進行詳細說明。The general formula (15) will be described in detail.

通式(15)中，M21 與上述通式(2)中的M11 同義，且較佳範圍亦相同。In the formula (15), M 21 is synonymous with M 11 in the above formula (2), and the preferred range is also the same.

Q21 、Q22 分別獨立表示形成含氮雜環(含有配位在M21 上的氮的環)的原子群。由Q21 、Q22 所形成的含氮雜環並無特別限定，例如可舉出吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吡唑環、咪唑環、噻唑環、噁唑環、吡咯環、***環、以及含有該些含氮雜環的稠環(例如喹啉環、喹噁啉環、酞嗪環、吲哚環、苯幷噁唑環、苯幷咪唑環、假吲哚環等)及該些稠環的互變異構物。Q 21 and Q 22 each independently represent an atomic group forming a nitrogen-containing hetero ring (a ring containing nitrogen coordinated to M 21 ). The nitrogen-containing hetero ring formed by Q 21 and Q 22 is not particularly limited, and examples thereof include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrazole ring, an imidazole ring, and a thiazole ring. An oxazole ring, a pyrrole ring, a triazole ring, and a fused ring containing the nitrogen-containing heterocyclic ring (eg, quinoline ring, quinoxaline ring, pyridazine ring, anthracene ring, benzoxazole ring, benzoimidazole) Rings, false anthracene rings, etc.) and tautomers of the fused rings.

由Q21 、Q22 所形成的含氮雜環，較好的是吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吡唑環、咪唑環、噁唑環、吡咯環、以及含有該些含氮雜環的稠環(例如喹啉環、喹噁啉環、酞嗪環、吲哚環、苯幷噁唑環、苯幷咪唑環等)及該些稠環的互變異構物，更好的是吡啶環、吡嗪環、嘧啶環、咪唑環、吡咯環、以及含有該些配位基的稠環(例如喹啉環等)及該些稠環的互變異構物，進而較好的是吡啶環及該吡啶環的稠環(例如喹啉環等)，尤其好的是吡啶環。The nitrogen-containing heterocyclic ring formed by Q 21 and Q 22 is preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrazole ring, an imidazole ring, an oxazole ring or a pyrrole ring. And a fused ring containing the nitrogen-containing heterocyclic ring (for example, a quinoline ring, a quinoxaline ring, a pyridazine ring, an anthracene ring, a benzoxazole ring, a benzoimidazole ring, etc.) and a mutual mutation of the fused rings More preferably, the structure is a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, a pyrrole ring, and a fused ring containing the ligand (for example, a quinoline ring, etc.) and tautomers of the fused ring. Further, a pyridine ring and a fused ring of the pyridine ring (e.g., a quinoline ring or the like) are preferred, and a pyridine ring is particularly preferred.

X21 、X22 分別獨立為氧原子、硫原子、經取代或未經取代的氮原子，更較好的是氧原子、硫原子、經取代的氮原子，進而較好的是氧原子、硫原子，尤其好的是氧原子。Y21 與上述通式(2)中的Y11 同義，且較佳範圍亦相同。X 21 and X 22 are each independently an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, more preferably an oxygen atom, a sulfur atom, a substituted nitrogen atom, and more preferably an oxygen atom or sulfur. Atoms, especially good are oxygen atoms. Y 21 is synonymous with Y 11 in the above formula (2), and the preferred range is also the same.

Y22 、Y23 分別獨立表示單鍵、連結基，較好的是單鍵。連結基並無特別限定，例如可舉出羰基連結基、硫羰基連結基、伸烷基、伸烯基、伸芳基、雜伸芳基、氧原子連結基、氮原子連結基、硫原子連結基、以及由該些連結基的組合所形成的連結基等。Y 22 and Y 23 each independently represent a single bond or a linking group, and preferably a single bond. The linking group is not particularly limited, and examples thereof include a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenyl group, an aryl group, a heteroaryl group, an oxygen atom linking group, a nitrogen atom linking group, and a sulfur atom linking group. a group and a linking group formed by a combination of the linking groups.

表示為Y22 或Y23 的連結基較好的是羰基連結基、伸烷基連結基、伸烯基連結基，更好的是羰基連結基、伸烯基連結基，進而較好的是羰基連結基。The linking group represented by Y 22 or Y 23 is preferably a carbonyl linking group, an alkylene linking group or an alkenyl linking group, more preferably a carbonyl linking group, an alkenyl linking group, and further preferably a carbonyl group. Linkage base.

R21 、R22 、R23 以及R24 分別獨立表示氫原子或取代基。取代基並無特別限定，例如可舉出：烷基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲基、乙基、異丙基、第三丁基、正辛基、正癸基、正十六烷基、環丙基、環戊基、環己基等)、烯基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙烯基、烯丙基、2-丁烯基、3-戊烯基等)、炔基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出炔丙基、3-戊炔基等)、芳基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯基、對甲基苯基、萘基、蒽基等)、胺基(較好的是碳數為0～30，更好的是碳數為0～20，尤其好的是碳數為0～10，例如可舉出胺基、甲胺基、二甲胺基、二乙胺基、二苄基胺基、二苯基胺基、二甲苯基胺基等)、烷氧基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲氧基、乙氧基、丁氧基、2-乙基己氧基等)、芳氧基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯氧基、1-萘氧基、2-萘氧基等)、雜環氧基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶氧基、吡嗪氧基、嘧啶氧基、喹啉氧基等)、醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出乙醯基、苯甲醯基、甲醯基、特戊醯基等)、烷氧基羰基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～12，例如可舉出甲氧基羰基、乙氧基羰基等)、芳氧基羰基(較好的是碳數為7～30，更好的是碳數為7～20，尤其好的是碳數為7～12，例如可舉出苯氧基羰基等)、醯氧基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯氧基、苯甲醯氧基等)、醯基胺基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯基胺基、苯甲醯基胺基等)、烷氧基羰基胺基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～12，例如可舉出甲氧基羰基胺基等)、芳氧基羰基胺基(較好的是碳數為7～30，更好的是碳數為7～20，尤其好的是碳數為7～12，例如可舉出苯氧基羰基胺基等)、磺醯基胺基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲磺醯基胺基、苯磺醯基胺基等)、胺磺醯基(較好的是碳數為0～30，更好的是碳數為0～20，尤其好的是碳數為0～12，例如可舉出胺磺醯基、甲基胺磺醯基、二甲基胺磺醯基、苯基胺磺醯基等)。R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom or a substituent. The substituent is not particularly limited, and examples thereof include an alkyl group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 10, for example, Illustrative of methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl (preferably The carbon number is 2 to 30, more preferably the carbon number is 2 to 20, and particularly preferably the carbon number is 2 to 10, and examples thereof include a vinyl group, an allyl group, a 2-butenyl group, and a 3-pentyl group. Alkenyl group, etc.), alkynyl group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 10, for example, propargyl group, 3 a pentynyl group or the like, an aryl group (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number of 6 to 12, and examples thereof include a phenyl group, P-methylphenyl, naphthyl, anthryl, etc.), an amine group (preferably having a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, particularly preferably a carbon number of 0 to 10, Examples thereof include an amine group, a methylamino group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a xylylamino group, and the like, and an alkane. The oxy group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 10, and examples thereof include a methoxy group, an ethoxy group, and a butoxy group). a group, a 2-ethylhexyloxy group or the like, an aryloxy group (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number of 6 to 12, for example Examples thereof include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and the like, and a heterocyclic oxy group (preferably, the carbon number is from 1 to 30, more preferably, the carbon number is from 1 to 20, particularly preferably The carbon number is 1 to 12, and examples thereof include a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group, and a quinolyloxy group, and a mercapto group (preferably, the carbon number is 1 to 30, more preferably The carbon number is from 1 to 20, particularly preferably from 1 to 12, and examples thereof include an ethyl hydrazino group, a benzamidine group, a decyl group, a pentylene group, and the like, and an alkoxycarbonyl group. The carbon number is 2 to 30, more preferably the carbon number is 2 to 20, particularly preferably the carbon number is 2 to 12, and examples thereof include a methoxycarbonyl group and an ethoxycarbonyl group, and an aryloxy group. a carbonyl group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, and examples thereof include a phenoxycarbonyl group. ), a decyloxy group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 10, and examples thereof include an ethyl oxy group and a benzoic acid group). a mercapto group or the like, a mercaptoamine group (preferably, the carbon number is 2 to 30, more preferably the carbon number is 2 to 20, and particularly preferably the carbon number is 2 to 10, and for example, acetamidine is exemplified. Alkylamino group, benzhydrylamino group, etc.), alkoxycarbonylamino group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2) ～12, for example, a methoxycarbonylamino group, etc.), an aryloxycarbonylamino group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably carbon) The number is 7 to 12, for example, a phenoxycarbonylamino group or the like, and a sulfonylamino group (preferably, the carbon number is 1 to 30, more preferably the carbon number is 1 to 20, particularly preferably The carbon number is 1 to 12, for example, a methanesulfonylamino group or a benzenesulfonylamino group, and an aminesulfonyl group (preferably, the carbon number is 0 to 30, more preferably the carbon number). It is 0 to 20, and particularly preferably, the carbon number is 0 to 12, and examples thereof include an amine sulfonyl group, a methylamine sulfonyl group, a dimethylamine sulfonyl group, and a phenylamine. Sulfonyl, etc.).

胺甲醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出胺甲醯基、甲基胺甲醯基、二乙基胺甲醯基、苯基胺甲醯基等)、烷硫基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲硫基、乙硫基等)、芳硫基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯硫基等)、雜環硫基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶硫基、2-苯并咪唑硫基、2-苯并噁唑硫基、2-苯并噻唑硫基等)、磺醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲磺醯基、甲苯磺醯基等)、亞磺醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲亞磺醯基、苯亞磺醯基等)、脲基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出脲基、甲基脲基、苯基脲基等)。Aminomethane group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 12, and examples thereof include an amine methyl group and a methyl amine. Mercapto, diethylamine, phenylamine, phenylamine, etc., alkylthio (preferably having a carbon number of from 1 to 30, more preferably from 1 to 20, particularly preferably The carbon number is 1 to 12, for example, a methylthio group or an ethylthio group, and an arylthio group (preferably, the carbon number is 6 to 30, and more preferably the carbon number is 6 to 20, particularly preferably). The carbon number is 6 to 12, for example, a phenylthio group or the like, and a heterocyclic thio group (preferably, the carbon number is 1 to 30, and more preferably the carbon number is 1 to 20, particularly preferably The carbon number is 1 to 12, and examples thereof include a pyridylthio group, a 2-benzimidazolylthio group, a 2-benzoxazolethio group, a 2-benzothiazolylthio group, and the like, and a sulfonyl group (preferably The carbon number is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, for example, a methylsulfonyl group or a toluenesulfonyl group, and a sulfinyl group (for example). Preferably, the carbon number is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, for example, sulfinyl group and phenyl sulfinic acid. a base or the like, a urea group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 12, for example, a urea group or a methyl urea Base, phenylurea group, etc.).

磷醯胺基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出二乙基磷醯胺基、苯基磷醯胺基等)、羥基、巰基、鹵素原子(例如氟原子、氯原子、溴原子、碘原子)、氰基、磺基、羧基、硝基、羥胺酸基(hydroxamic acid group)、亞磺酸基、肼基、亞胺基、雜環基(較好的是碳數為1～30，更好的是碳數為1～12，雜原子例如可舉出氮原子、氧原子、硫原子，該雜環基具體可舉出例如咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基(piperidyl)、嗎啉基(morpholino)、苯幷噁唑基、苯并咪唑基、苯并噻唑基、咔唑基(carbazolyl)、氮雜卓基(azepinyl)等)、矽烷基(較好的是碳數為3～40，更好的是碳數為3～30，尤其好的是碳數為3～24，例如可舉出三甲基矽烷基、三苯基矽烷基等)、矽烷氧基(較好的是碳數為3～40，更好的是碳數為3～30，尤其好的是碳數為3～24，例如可舉出三甲基矽烷氧基、三苯基矽烷氧基等)等。該些取代基亦可經進一步取代。The phosphonium amine group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 12, and examples thereof include diethylphosphonium amino group, Phenylphosphoniumamine, etc., hydroxyl group, mercapto group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, a sulfinic acid group, a fluorenyl group, an imido group or a heterocyclic group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 12, and examples of the hetero atom include a nitrogen atom and an oxygen atom; A sulfur atom, and the heterocyclic group specifically includes, for example, an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a piperidyl group, a morpholino group, a benzoxazolyl group, a benzo group. Imidazolyl, benzothiazolyl, carbazolyl, azepinyl, etc., decylalkyl (preferably having a carbon number of from 3 to 40, more preferably a carbon number of from 3 to 30, Particularly preferably, the carbon number is from 3 to 24, and examples thereof include a trimethyldecyl group and a triphenylsulfanyl group, and a decyloxy group (preferably, the carbon number is from 3 to 40, more preferably the carbon number). 3 to 30, especially good for carbon 3 to 24, and examples thereof include alkoxy trimethyl silicon, silicon triphenyl alkoxy and the like) and the like. These substituents may also be further substituted.

R21 、R22 、R23 以及R24 較好的是分別獨立為烷基、芳基、R21 與R22 或者R23 與R24 鍵結而形成環結構(例如苯幷稠環、吡啶稠環等)的基，更好的是R21 與R22 或R23 與R24 鍵結而形成環結構(例如苯幷稠環、吡啶稠環等)的基。R 21 , R 22 , R 23 and R 24 are preferably independently alkyl, aryl, R 21 and R 22 or R 23 and R 24 are bonded to form a ring structure (for example, a benzoquinone fused ring or a pyridine thick). More preferably, R 21 and R 22 or R 23 are bonded to R 24 to form a ring structure (e.g., a benzoquinone fused ring, a pyridine fused ring, etc.).

L25 與上述通式(2)中的L15 同義，且較佳範圍亦相同。L 25 is synonymous with L 15 in the above formula (2), and the preferred range is also the same.

n 21 與上述通式(2)中的n11 同義，且較佳範圍亦相同。 n 21 is synonymous with n 11 in the above formula (2), and the preferred range is also the same.

通式(15)中較好的是：當Q21 、Q22 所形成的環為吡啶環時Y21 表示連結基的金屬錯合物；Q21 、Q22 所形成的環為吡啶環，Y21 為單鍵或雙鍵且X21 、X22 表示硫原子、經取代或未經取代的氮原子的金屬錯合物；或者Q21 、Q22 所形成的環表示含氮雜五員環、或者含有兩個以上氮原子的含氮六員環的金屬錯合物。Preferably, in the formula (15), when the ring formed by Q 21 and Q 22 is a pyridine ring, Y 21 represents a metal complex of a linking group; and the ring formed by Q 21 and Q 22 is a pyridine ring, Y 21 is a single bond or a double bond, and X 21 and X 22 represent a sulfur atom, a metal complex of a substituted or unsubstituted nitrogen atom; or a ring formed by Q 21 and Q 22 represents a nitrogen-containing five-membered ring, Or a metal complex of a nitrogen-containing six-membered ring containing two or more nitrogen atoms.

以上述通式(15)所表示的化合物的較佳形態為以下述通式(1-A)所表示的化合物。A preferred embodiment of the compound represented by the above formula (15) is a compound represented by the following formula (1-A).

對通式(1-A)進行說明。The general formula (1-A) will be described.

通式(1-A)中，M31 與上述通式(2)中的M11 同義，且較佳範圍亦相同。In the formula (1-A), M 31 is synonymous with M 11 in the above formula (2), and the preferred range is also the same.

Z31 、Z32 、Z33 、Z34 、Z35 以及Z36 分別獨立表示經取代或未經取代的碳原子、氮原子，更好的是經取代或未經取代的碳原子。碳上的取代基可舉出以上述通式(1)中的R21 所說明的基，而且，Z31 與Z32 、Z32 與Z33 、Z33 與Z34 、Z34 與Z35 、Z35 與Z36 可經由連結基而鍵結形成稠環(例如苯幷稠環、吡啶稠環等)，Z31 與T31 、Z36 與T38 可經由連結基而鍵結形成稠環(例如苯幷稠環、吡啶稠環等)。Z 31 , Z 32 , Z 33 , Z 34 , Z 35 and Z 36 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom, more preferably a substituted or unsubstituted carbon atom. The substituent on the carbon may be a group described by R 21 in the above formula (1), and Z 31 and Z 32 , Z 32 and Z 33 , Z 33 and Z 34 , Z 34 and Z 35 , Z 35 and Z 36 may be bonded via a linking group to form a fused ring (for example, a benzoquinone fused ring, a pyridine fused ring, etc.), and Z 31 and T 31 , Z 36 and T 38 may be bonded via a linking group to form a fused ring ( For example, benzoquinone fused ring, pyridine fused ring, etc.).

上述碳上的取代基，較好的是烷基、烷氧基、烷胺基、芳基、形成稠環(例如苯幷稠環、吡啶稠環等)的基、鹵素原子，更好的是烷胺基、芳基、形成稠環(例如苯并稠環、吡啶稠環等)的基，進而較好的是芳基、形成稠環(例如苯并稠環、吡啶稠環等)的基，尤其好的是形成稠環(例如苯并稠環、吡啶稠環等)的基。The substituent on the above carbon is preferably an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a fused ring (e.g., a benzoquinone fused ring, a pyridine fused ring, or the like), a halogen atom, and more preferably An alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzo fused ring, a pyridine fused ring, or the like), and more preferably an aryl group, a group forming a condensed ring (for example, a benzo fused ring, a pyridine fused ring, or the like). Particularly preferred is a group which forms a fused ring (e.g., a benzo fused ring, a pyridine fused ring, etc.).

T31 、T32 、T33 、T34 、T35 、T36 、T37 以及T38 分別獨立表示經取代或未經取代的碳原子、氮原子，更好的是經取代或未經取代的碳原子。碳上的取代基可舉出以上述通式(1)中的R21 所說明的基，而且，T31 與T32 、T32 與T33 、T33 與T34 、T35 與T36 、T36 與T37 、T37 與T38 可經由連結基而鍵結形成稠環(例如苯并稠環、吡啶稠環等)。T 31 , T 32 , T 33 , T 34 , T 35 , T 36 , T 37 and T 38 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom, more preferably a substituted or unsubstituted one. carbon atom. The substituent on the carbon may be a group described by R 21 in the above formula (1), and T 31 and T 32 , T 32 and T 33 , T 33 and T 34 , T 35 and T 36 , T 36 and T 37 , T 37 and T 38 may be bonded via a linking group to form a fused ring (e.g., a benzo fused ring, a pyridine fused ring, etc.).

上述碳上的取代基，較好的是烷基、烷氧基、烷胺基、芳基、形成稠環(例如苯并稠環、吡啶稠環等)的基、鹵素原子，更好的是芳基、形成稠環(例如苯并稠環、吡啶稠環等)的基、鹵素原子，進而較好的是芳基、鹵素原子，尤其好的是芳基。The substituent on the above carbon is preferably an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (e.g., a benzo fused ring, a pyridine fused ring, etc.), a halogen atom, and more preferably The aryl group, a group forming a fused ring (e.g., a benzo fused ring, a pyridine fused ring, etc.), a halogen atom, and more preferably an aryl group or a halogen atom, particularly preferably an aryl group.

X31 、X32 分別獨立與上述通式(15)中的X21 、X22 同義，且較佳範圍亦相同。X 31 and X 32 are each independently synonymous with X 21 and X 22 in the above formula (15), and the preferred ranges are also the same.

對以通式(15-2)所表示的化合物進行說明。The compound represented by the formula (15-2) will be described.

通式(15-2)中，M51 與上述通式(2)中的M11 同義，且較佳範圍亦相同。In the formula (15-2), M 51 is synonymous with M 11 in the above formula (2), and the preferred range is also the same.

Q51 、Q52 分別獨立與上述通式(15)中的Q21 、Q22 同義，且較佳範圍亦相同。Q 51 and Q 52 are each independently synonymous with Q 21 and Q 22 in the above formula (15), and the preferred ranges are also the same.

Q53 、Q54 分別獨立表示形成含氮雜環(含有配位在M51 上的氮的環)的基。由Q53 、Q54 所形成的含氮雜環並無特別限定，較好的是吡咯衍生物的互變異構物(例如日本專利特開2007-103493化合物編號「化24」中記載的例示化合物(24)的五員雜環配位基、化合物編號「化28」中記載的例示化合物(64)的末端五員雜環配位基、化合物編號「化37」中記載的例示化合物(145)的五員雜環配位基等)、咪唑衍生物的互變異構物(例如日本專利特開2007-103493化合物編號「化24」中記載的例示化合物(29)的雜五員環配位基等)、噻唑衍生物的互變異構物(例如日本專利特開2007-103493化合物編號「化24」中記載的例示化合物(30)的雜五員環配位基等)、噁唑衍生物的互變異構物(例如日本專利特開2007-103493化合物編號「化24」中記載的例示化合物(31)的雜五員環配位基等)，更好的是吡咯衍生物的互變異構物、咪唑衍生物的互變異構物、噻唑衍生物的互變異構物，進而較好的是吡咯衍生物的互變異構物、咪唑衍生物的互變異構物，尤其好的是吡咯衍生物的互變異構物。Q 53 and Q 54 each independently represent a group forming a nitrogen-containing hetero ring (a ring containing a nitrogen coordinated to M 51 ). The nitrogen-containing heterocyclic ring formed by Q 53 and Q 54 is not particularly limited, and is preferably a tautomeric product of a pyrrole derivative (for example, an exemplary compound described in JP-A-2007-103493, Compound No. "Chem. 24" The five-membered heterocyclic ligand of (24), the terminal five-membered heterocyclic ligand of the exemplified compound (64) described in the compound number "Chemical Formula 28", and the exemplified compound (145) described in the compound number "Chem. 37" a five-membered heterocyclic ligand, etc.), a tautomer of an imidazole derivative (for example, a heterocyclic five-membered ring ligand of the exemplified compound (29) described in JP-A-2007-103493, Compound No. "Chem. 24" And the tautomer of the thiazole derivative (for example, a heterocyclic ring of the exemplified compound (30) described in the compound No. 2007-103493, No. 24-103493), and an oxazole derivative. A tautomer (for example, a heteroquinone ring ligand of the exemplified compound (31) described in the compound number "Chemical 24" of JP-A-2007-103493), and more preferably a tautomer of a pyrrole derivative. a tautomer of an imidazole derivative, a tautomer of a thiazole derivative, Preferably tautomers, imidazole derivatives tautomer pyrrole derivative, particularly preferably tautomeric pyrrole derivatives.

Y51 與上述通式(2)中的Y11 同義，且較佳範圍亦相同。Y 51 is synonymous with Y 11 in the above formula (2), and the preferred range is also the same.

L55 與上述通式(2)中的L15 同義，且較佳範圍亦相同。L 55 is synonymous with L 15 in the above formula (2), and the preferred range is also the same.

n51 與上述n11 同義，且較佳範圍亦相同。n 51 is synonymous with n 11 above, and the preferred range is also the same.

W51 、W52 分別獨立表示經取代或未經取代的碳原子、氮原子，較好的是未經取代的碳原子、氮原子，更好的是未經取代的碳原子。W 51 and W 52 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom, preferably an unsubstituted carbon atom, a nitrogen atom, more preferably an unsubstituted carbon atom.

對以通式(15-3)所表示的化合物進行說明。The compound represented by the formula (15-3) will be described.

通式(15-3)中，MA1 、QA1 、QA2 、YA1 、YA2 、YA3 、RA1 、RA2 、RA3 、RA4 、LA5 以及nA1 分別與上述通式(1)中的M21 、Q21 、Q22 、Y21 、Y22 、Y23 、R21 、R22 、R23 、R24 、L25 以及n21 同義，且較佳範圍亦相同。In the general formula (15-3), M A1 , Q A1 , Q A2 , Y A1 , Y A2 , Y A3 , R A1 , R A2 , R A3 , R A4 , L A5 and n A1 are respectively the above formula ( M 21 , Q 21 , Q 22 , Y 21 , Y 22 , Y 23 , R 21 , R 22 , R 23 , R 24 , L 25 and n 21 in 1) are synonymous, and the preferred ranges are also the same.

以上述通式(15-3)所表示的化合物的較佳形態為以下述通式(3-B)所表示的化合物。A preferred embodiment of the compound represented by the above formula (15-3) is a compound represented by the following formula (3-B).

對以通式(3-B)所表示的化合物進行說明。The compound represented by the formula (3-B) will be described.

通式(3-B)中，M71 與上述通式(2)中的M11 同義，且較佳範圍亦相同。In the formula (3-B), M 71 is synonymous with M 11 in the above formula (2), and the preferred range is also the same.

Y71 、Y72 以及Y73 分別與通式(15)中的Y21 、Y22 以及Y23 同義，且較佳範圍亦相同。Y 71 , Y 72 and Y 73 are synonymous with Y 21 , Y 22 and Y 23 in the formula (15), respectively, and the preferred ranges are also the same.

L75 與上述通式(2)中的L15 同義，且較佳範圍亦相同。L 75 is synonymous with L 15 in the above formula (2), and the preferred range is also the same.

n71 與上述通式(2)中的n11 同義，且較佳範圍亦相同。n 71 is synonymous with n 11 in the above formula (2), and the preferred range is also the same.

Z71 、Z72 、Z73 、Z74 、Z75 以及Z76 分別獨立表示經取代或未經取代的碳原子、氮原子，較好的是經取代或未經取代的碳原子。碳上的取代基可舉出以上述通式(15)中的R21 所說明的基。而且，R71 與R72 、R73 與R74 可經由連結基而鍵結形成環(例如苯環、吡啶環)。R71 ～R74 與上述通式(15)中的R21 ～R24 的取代基同義，且較佳範圍亦相同。Z 71 , Z 72 , Z 73 , Z 74 , Z 75 and Z 76 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom, preferably a substituted or unsubstituted carbon atom. The substituent on the carbon may be a group described by R 21 in the above formula (15). Further, R 71 and R 72 , R 73 and R 74 may be bonded via a linking group to form a ring (for example, a benzene ring or a pyridine ring). R 71 to R 74 have the same meanings as the substituents of R 21 to R 24 in the above formula (15), and the preferred ranges are also the same.

以上述通式(3-B)所表示的化合物的較佳形態為以下述通式(3-C)所表示的化合物。A preferred embodiment of the compound represented by the above formula (3-B) is a compound represented by the following formula (3-C).

對以通式(3-C)所表示的化合物進行說明。The compound represented by the formula (3-C) will be described.

通式(3-C)中，RC1 、RC2 分別獨立表示氫原子或取代基，取代基是表示作為上述通式(15)中的R21 至R24 的取代基而進行說明的烷基、芳基、雜環基(該些基亦可經進一步取代。此時的取代基例如可使用作為由上述通式(15)中的R21 所表示的取代基而舉出的基)、鹵素原子。RC3 、RC4 、RC5 以及RC6 所表示的取代基亦與上述通式(15)中的R21 至R24 的取代基同義。nC3 、nC6 表示0～3的整數，nC4 、nC5 表示0～4的整數，當分別具有多個RC3 、RC4 、RC5 、RC6 時，多個RC3 、RC4 、RC5 、RC6 可相同亦可不同，亦可連結而形成環。RC3 、RC4 、RC5 、RC6 較好的是烷基、芳基、雜芳基、氰基、鹵素原子。In the formula (3-C), R C1 and R C2 each independently represent a hydrogen atom or a substituent, and the substituent is an alkyl group which is described as a substituent of R 21 to R 24 in the above formula (15). And an aryl group or a heterocyclic group (the group may be further substituted. The substituent at this time may be, for example, a group exemplified as the substituent represented by R 21 in the above formula (15)), and a halogen. atom. The substituent represented by R C3 , R C4 , R C5 and R C6 is also synonymous with the substituent of R 21 to R 24 in the above formula (15). n C3 and n C6 represent integers of 0 to 3, n C4 and n C5 represent integers of 0 to 4, and when there are a plurality of R C3 , R C4 , R C5 , and R C6 , respectively, a plurality of R C3 and R C4 , R C5 and R C6 may be the same or different, and may be linked to form a ring. R C3 , R C4 , R C5 and R C6 are preferably an alkyl group, an aryl group, a heteroaryl group, a cyano group or a halogen atom.

對以通式(15-4)所表示的化合物進行說明。The compound represented by the formula (15-4) will be described.

通式(15-4)中，MB1 、YB2 、YB3 、RB1 、RB2 、RB3 、RB4 、LB5 、nB3 、XB1 以及XB2 分別與上述通式(15)中的M21 、Y22 、Y23 、R21 、R22 、R23 、R24 、L25 、n21 、X21 以及X22 同義，且較佳範圍亦相同。In the formula (15-4), M B1 , Y B2 , Y B3 , R B1 , R B2 , R B3 , R B4 , L B5 , n B3 , X B1 and X B2 are respectively in the above formula (15) M 21 , Y 22 , Y 23 , R 21 , R 22 , R 23 , R 24 , L 25 , n 21 , X 21 and X 22 are synonymous, and the preferred ranges are also the same.

YB1 表示連結基，且與上述通式(15)中的Y21 相同，較好的是表示在1、2位取代的乙烯基、伸苯基環、吡啶環、吡嗪環、嘧啶環或者碳數2～8的伸烷基。Y B1 represents a linking group, and is the same as Y 21 in the above formula (15), and preferably represents a vinyl group, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or a substituted at the 1,2 position. An alkyl group having 2 to 8 carbon atoms.

RB5 、RB6 分別獨立表示氫原子或取代基，取代基是表示作為上述通式(15)中的R21 至R24 的取代基進行說明的烷基、芳基、雜環基。其中，YB1 不與RB5 或RB6 連結。nB1 、nB2 分別獨立表示0或1的整數。R B5 and R B6 each independently represent a hydrogen atom or a substituent, and the substituent is an alkyl group, an aryl group or a heterocyclic group which is described as a substituent of R 21 to R 24 in the above formula (15). Wherein Y B1 is not linked to R B5 or R B6 . n B1 and n B2 each independently represent an integer of 0 or 1.

以上述通式(15-4)所表示的化合物的較佳形態為以下述通式(4-A)所表示的化合物。A preferred embodiment of the compound represented by the above formula (15-4) is a compound represented by the following formula (4-A).

對以通式(4-A)所表示的化合物進行說明。The compound represented by the formula (4-A) will be described.

通式(4-A)中，RD3 、RD4 分別獨立表示氫原子或取代基，RD1 、RD2 分別表示取代基。RD1 、RD2 、RD3 以及RD4 所表示的取代基與上述通式(15-4)中的RB5 、RB6 所表示的取代基同義，且較佳範圍亦相同。nD1 、nD2 表示0～4的整數，當具有分別為多個的RD1 、RD2 時，多個RD1 、RD2 可相同亦可不同，亦可連結而形成環。YD1 表示在1、2位取代的乙烯基、伸苯基環、吡啶環、吡嗪環、嘧啶環或者碳數1～8的伸烷基。In the formula (4-A), R D3 and R D4 each independently represent a hydrogen atom or a substituent, and R D1 and R D2 each represent a substituent. The substituent represented by R D1 , R D2 , R D3 and R D4 has the same meaning as the substituent represented by R B5 and R B6 in the above formula (15-4), and the preferred range is also the same. n D1 and n D2 represent an integer of 0 to 4. When there are a plurality of R D1 and R D2 , respectively, a plurality of R D1 and R D2 may be the same or different, and may be connected to form a ring. Y D1 represents a vinyl group, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or an alkylene group having 1 to 8 carbon atoms substituted at the 1,2 position.

對以通式(15-5)所表示的化合物進行說明。The compound represented by the formula (15-5) will be described.

通式(15-5)中，M61 與上述通式(2)中的M11 同義，且較佳範圍亦相同。In the formula (15-5), M 61 is synonymous with M 11 in the above formula (2), and the preferred range is also the same.

Q61 、Q62 分別獨立表示形成環的基。由Q61 、Q62 所形成的環並無特別限定，例如可舉出苯環、吡啶環、噠嗪環、嘧啶環、噻吩環、異噻唑環、呋喃環、異噁唑環、以及該些環的稠環。Q 61 and Q 62 each independently represent a group forming a ring. The ring formed by Q 61 and Q 62 is not particularly limited, and examples thereof include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a thiophene ring, an isothiazole ring, a furan ring, an isoxazole ring, and the like. The fused ring of the ring.

由Q61 、Q62 所形成的環較好的是苯環、吡啶環、噻吩環、噻唑環以及該些環的稠環，更好的是苯環、吡啶環以及該些環的稠環，進而較好的是苯環及該苯環的稠環。The ring formed by Q 61 and Q 62 is preferably a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring and a fused ring of the rings, more preferably a benzene ring, a pyridine ring and a fused ring of the rings. Further preferred are a benzene ring and a fused ring of the benzene ring.

Y61 與上述通式(2)中的Y11 同義，且較佳範圍亦相同。Y 61 is synonymous with Y 11 in the above formula (2), and the preferred range is also the same.

Y62 、Y63 分別獨立表示連結基或單鍵。連結基並無特別限定，例如可舉出羰基連結基、硫羰基連結基、伸烷基、伸烯基、伸芳基、雜伸芳基、氧原子連結基、氮原子連結基、以及由該些連結基的組合所形成的連結基等。Y 62 and Y 63 each independently represent a linking group or a single bond. The linking group is not particularly limited, and examples thereof include a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenyl group, an extended aryl group, a heteroaryl group, an oxygen atom linking group, a nitrogen atom linking group, and the like. A linking group or the like formed by a combination of these linking groups.

Y62 、Y63 較好的是分別獨立為單鍵、羰基連結基、伸烷基連結基、伸烯基，更好的是單鍵、伸烯基，進而較好的是單鍵。Y 62 and Y 63 are each independently a single bond, a carbonyl linking group, an alkyl group-bonding group, an alkenyl group, and more preferably a single bond or an extended alkenyl group, and more preferably a single bond.

L65 與上述通式(2)中的L15 同義，且較佳範圍亦相同。L 65 is synonymous with L 15 in the above formula (2), and the preferred range is also the same.

n61 與上述通式(2)中的n11 同義，且較佳範圍亦相同。n 61 is synonymous with n 11 in the above formula (2), and the preferred range is also the same.

Z61 、Z62 、Z63 、Z64 、Z65 、Z66 、Z67 以及Z68 分別獨立表示經取代或未經取代的碳原子、氮原子，較好的是經取代或未經取代的碳原子。碳上的取代基可舉出以上述通式(15)中的R21 所說明的基，而且，Z61 與Z62 、Z62 與Z63 、Z63 與Z64 、Z65 與Z66 、Z66 與Z67 、Z67 與Z68 可經由連結基而鍵結形成稠環(例如苯幷稠環、吡啶稠環等)。由Q61 、Q62 所形成的環可經由連結基而分別與Z61 、Z68 鍵結形成環。Z 61 , Z 62 , Z 63 , Z 64 , Z 65 , Z 66 , Z 67 and Z 68 each independently represent a substituted or unsubstituted carbon atom, a nitrogen atom, preferably substituted or unsubstituted. carbon atom. The substituent on the carbon may be a group described by R 21 in the above formula (15), and further, Z 61 and Z 62 , Z 62 and Z 63 , Z 63 and Z 64 , Z 65 and Z 66 , Z 66 and Z 67 , Z 67 and Z 68 may be bonded via a linking group to form a fused ring (e.g., a benzoquinone fused ring, a pyridine fused ring, etc.). The ring formed by Q 61 and Q 62 may be bonded to Z 61 and Z 68 via a linking group to form a ring.

上述碳上的取代基，較好的是烷基、烷氧基、烷胺基、芳基、形成稠環(例如苯幷稠環、吡啶稠環等)的基、鹵素原子，更好的是烷胺基、芳基、形成稠環(例如苯幷稠環、吡啶稠環等)的基，進而較好的是芳基、形成稠環(例如苯幷稠環、吡啶稠環等)的基，尤其好的是形成稠環(例如苯幷稠環、吡啶稠環等)的基。The substituent on the above carbon is preferably an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a fused ring (e.g., a benzoquinone fused ring, a pyridine fused ring, or the like), a halogen atom, and more preferably An alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzoquinone fused ring, a pyridine fused ring, or the like), and more preferably an aryl group, a group forming a fused ring (for example, a benzoquinone fused ring, a pyridine fused ring, or the like). Particularly preferred is a group which forms a fused ring (e.g., a benzoquinone fused ring, a pyridine fused ring, etc.).

本發明中的電子傳輸性磷光發光材料較好的是鉑錯合物。The electron transporting phosphorescent material in the present invention is preferably a platinum complex.

較好的是包含以通式(16)所表示的部分結構的四牙配位基的鉑錯合物。A platinum complex containing a tetradentate ligand having a partial structure represented by the general formula (16) is preferred.

通式(16)中，Z1 表示以氮原子而配位在鉑上的含氮雜環。L1 表示單鍵或連結基。R1 、R3 、R4 表示氫原子或取代基，R2 表示取代基。In the formula (16), Z 1 represents a nitrogen-containing hetero ring which is coordinated to platinum by a nitrogen atom. L 1 represents a single bond or a linking group. R 1 , R 3 and R 4 represent a hydrogen atom or a substituent, and R 2 represents a substituent.

Z1 表示以氮原子而配位在鉑上的含氮雜環。Z1 例如可舉出吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吡唑環、咪唑環、噁唑環、噻唑環、***環、噁二唑環、噻二唑環、以及該些環的苯幷稠環、吡啶幷稠環等，較好的是吡啶環、吡嗪環、嘧啶環、吡唑環、***環，更好的是吡啶環、吡嗪環、嘧啶環，尤其好的是吡啶環。該些環亦可具有取代基，取代基可使用作為後述的L1 的取代基而舉出的取代基。Z 1 represents a nitrogen-containing heterocyclic ring coordinated to platinum by a nitrogen atom. Examples of Z 1 include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a triazole ring, an oxadiazole ring, and a thiadiazole. The ring, and the benzoquinone fused ring, the pyridinium fused ring or the like of the rings are preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrazole ring, a triazole ring, more preferably a pyridine ring or a pyrazine ring. A pyrimidine ring, particularly preferably a pyridine ring. These rings may have a substituent, and a substituent which is a substituent of L 1 to be described later may be used as the substituent.

L1 表示單鍵或連結基。連結基並無特別限定，較好的是由碳原子、氮原子、氧原子、硫原子、矽原子所形成連結基，以下表示具體例，但並不限定於該些連結基。L 1 represents a single bond or a linking group. The linking group is not particularly limited, but a linking group formed of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a ruthenium atom is preferred. Specific examples are shown below, but are not limited to these linking groups.

若可能，該些連結基亦可進一步具有取代基，作為可導入的取代基，取代基可舉出：烷基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲基、乙基、異丙基、第三丁基、正辛基、正癸基、正十六烷基、環丙基、環戊基、環己基等)、烯基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙烯基、烯丙基、2-丁烯基、3-戊烯基等)、炔基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出炔丙基、3-戊炔基等)、芳基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯基、對甲基苯基、萘基、蒽基等)、胺基(較好的是碳數為0～30，更好的是碳數為0～20，尤其好的是碳數為0～10，例如可舉出胺基、甲胺基、二甲胺基、二乙胺基、二苄基胺基、二苯基胺基、二甲苯基胺基等)、烷氧基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲氧基、乙氧基、丁氧基、2-乙基己氧基等)、芳氧基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯氧基、1-萘氧基、2-萘氧基等)、雜環氧基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶氧基、吡嗪氧基、嘧啶氧基、喹啉氧基等)、醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出乙醯基、苯甲醯基、甲醯基、特戊醯基等)、烷氧基羰基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～12，例如可舉出甲氧基羰基、乙氧基羰基等)、芳氧基羰基(較好的是碳數為7～30，更好的是碳數為7～20，尤其好的是碳數為7～12，例如可舉出苯氧基羰基等)、醯氧基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯氧基、苯甲醯氧基等)、醯基胺基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～10，例如可舉出乙醯基胺基、苯甲醯基胺基等)、烷氧基羰基胺基(較好的是碳數為2～30，更好的是碳數為2～20，尤其好的是碳數為2～12，例如可舉出甲氧基羰基胺基等)、芳氧基羰基胺基(較好的是碳數為7～30，更好的是碳數為7～20，尤其好的是碳數為7～12，例如可舉出苯氧基羰基胺基等)、磺醯基胺基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲磺醯基胺基、苯磺醯基胺基等)、胺磺醯基(較好的是碳數為0～30，更好的是碳數為0～20，尤其好的是碳數為0～12，例如可舉出胺磺醯基、甲基胺磺醯基、二甲基胺磺醯基、苯基胺磺醯基等)、胺甲醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出胺甲醯基、甲基胺甲醯基、二乙基胺甲醯基、苯基胺甲醯基等)、烷硫基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲硫基、乙硫基等)、芳硫基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯硫基等)、雜環硫基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶硫基、2-苯并咪唑硫基、2-苯幷噁唑硫基、2-苯幷噻唑硫基等)、磺醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲磺醯基、甲苯磺醯基等)、亞磺醯基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲亞磺醯基、苯亞磺醯基等)、脲基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出脲基、甲基脲基、苯基脲基等)、磷醯胺基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出二乙基磷醯胺、苯基磷醯胺等)、羥基、巰基、鹵素原子(例如氟原子、氯原子、溴原子、碘原子)、氰基、磺基、羧基、硝基、羥胺酸基、亞磺酸基、肼基、亞胺基、雜環基(較好的是碳數為1～30，更好的是碳數為1～12，雜原子例如為氮原子、氧原子、硫原子，該雜環基具體可舉出咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、嗎啉基、苯幷噁唑基、苯幷咪唑基、苯幷噻唑基、咔唑基、氮雜卓基等)、矽烷基(較好的是碳數為3～40，更好的是碳數為3～30，尤其好的是碳數為3～24，例如可舉出三甲基矽烷基、三苯基矽烷基等)、矽烷氧基(較好的是碳數為3～40，更好的是碳數為3～30，尤其好的是碳數為3～24，例如可舉出三甲基矽烷氧基、三苯基矽烷氧基等)等。該些取代基亦可經進一步取代。取代基較好的是烷基、芳基、雜環基、鹵素原子、矽烷基，更好的是烷基、芳基、雜環基、鹵素原子，進而較好的是烷基、芳基、芳香族雜環基、氟原子。If possible, the linking group may further have a substituent. The substituent may be an alkyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 1). 20, particularly preferably, the carbon number is from 1 to 10, and examples thereof include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, an n-octyl group, a n-decyl group, a n-hexadecyl group, and a cyclopropyl group. a cyclopentyl group, a cyclohexyl group or the like, an alkenyl group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 10, for example, ethylene) a base, an allyl group, a 2-butenyl group, a 3-pentenyl group or the like), an alkynyl group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably carbon) The number is 2 to 10, and examples thereof include a propargyl group and a 3-pentynyl group, and an aryl group (preferably, the carbon number is 6 to 30, and more preferably the carbon number is 6 to 20, particularly preferably The carbon number is 6 to 12, for example, a phenyl group, a p-methylphenyl group, a naphthyl group or a fluorenyl group, and an amine group (preferably, the carbon number is 0 to 30, and more preferably the carbon number is 0 to 20, particularly preferably, the carbon number is 0 to 10, and examples thereof include an amine group, a methylamino group, a dimethylamino group, and a diethylamino group. a benzylamino group, a diphenylamino group, a xylylamino group, or the like, an alkoxy group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably carbon) The number is 1 to 10, and examples thereof include a methoxy group, an ethoxy group, a butoxy group, a 2-ethylhexyloxy group, and the like, and an aryloxy group (preferably, the carbon number is 6 to 30, more preferably The carbon number is 6 to 20, particularly preferably the carbon number is 6 to 12, and examples thereof include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and the like, and a heterocyclic oxy group (preferably, The carbon number is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, and examples thereof include a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group, and a quinolinyloxy group. Etc.), mercapto group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, for example, an ethylidene group or a benzamidine group) Alkoxycarbonyl group (preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 12) Examples thereof include a methoxycarbonyl group and an ethoxycarbonyl group, and an aryloxycarbonyl group (preferably, the carbon number is 7 to 30, and more preferably the carbon number is 7 to 20, Preferably, the carbon number is 7 to 12, for example, a phenoxycarbonyl group or the like, and a decyloxy group (preferably, the carbon number is 2 to 30, more preferably the carbon number is 2 to 20, particularly preferably The carbon number is 2 to 10, for example, an ethoxylated group or a benzamidineoxy group, or a mercaptoamine group (preferably, the carbon number is 2 to 30, and more preferably, the carbon number is 2). ～20, particularly preferably a carbon number of 2 to 10, for example, an ethenylamino group or a benzhydrylamino group, or an alkoxycarbonylamino group (preferably having a carbon number of 2 to 30) More preferably, the carbon number is 2 to 20, particularly preferably the carbon number is 2 to 12, for example, a methoxycarbonylamino group or the like, and an aryloxycarbonylamino group (preferably, the carbon number is 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, for example, a phenoxycarbonylamino group, etc.), a sulfonylamino group (preferably carbon) The number is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, for example, a methylsulfonylamino group or a benzenesulfonylamino group, and an amine sulfonate. Sulfhydryl (preferably, the carbon number is 0 to 30, more preferably the carbon number is 0 to 20, and particularly preferably the carbon number is 0 to 12, for example, an amine sulfonate a mercapto group, a methylamine sulfonyl group, a dimethylamine sulfonyl group, a phenylamine sulfonyl group, etc., an amine formazan group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include an amine methyl sulfonyl group, a methylamine methyl fluorenyl group, a diethylamine methyl fluorenyl group, a phenylamine methyl fluorenyl group, and the like, and an alkyl sulfide. The base (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, for example, a methylthio group or an ethylthio group), Sulfur-based (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number of 6 to 12, for example, a phenylthio group, etc.), a heterocyclic sulfur group (preferably, the number of carbon atoms is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably from 1 to 12 carbon atoms, and examples thereof include a pyridylthio group and a 2-benzimidazolylthio group. 2-benzoxazole thiol, 2-benzothiazolylthiol, etc., sulfonyl (preferably, the number of carbon atoms is from 1 to 30, more preferably from 1 to 20 carbon atoms, particularly preferably carbon) The number is 1 to 12, and examples thereof include a methanesulfonyl group and a toluenesulfonyl group, and a sulfinyl group (preferably, the carbon number is 1 to 30, and more preferably the carbon number is 1 to 20). Particularly preferably, the carbon number is 1 to 12, for example, a sulfinyl group or a sulfinyl group, or a urea group (preferably, the carbon number is 1 to 30, and more preferably the carbon number is 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include a urea group, a methylureido group, and a phenylureido group, and a phosphonium amine group (preferably, the carbon number is 1 to 30, More preferably, the carbon number is from 1 to 20, particularly preferably from 1 to 12, and examples thereof include diethylphosphoniumamine, phenylphosphoniumamine, etc., a hydroxyl group, a mercapto group, and a halogen atom (e.g., fluorine). Atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxylamine group, sulfinic acid group, sulfhydryl group, imido group, heterocyclic group (preferably, the carbon number is 1 to 30, more preferably a carbon number of 1 to 12, and a hetero atom is, for example, a nitrogen atom, an oxygen atom or a sulfur atom, and the heterocyclic group may specifically be an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group or a thiophene group. Base, piperidinyl, morpholinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, oxazolyl, azathiol, etc.), decylalkyl (preferably having a carbon number of 3 to 40) More preferably, the carbon number is 3 to 30, and particularly preferably the carbon number is 3. ～24, for example, a trimethyldecyl group or a triphenyldecyl group, or a decyloxy group (preferably having a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, particularly preferably) The carbon number is 3 to 24, and examples thereof include a trimethyldecyloxy group and a triphenyldecyloxy group. These substituents may also be further substituted. The substituent is preferably an alkyl group, an aryl group, a heterocyclic group, a halogen atom or a fluorenyl group, more preferably an alkyl group, an aryl group, a heterocyclic group or a halogen atom, and further preferably an alkyl group or an aryl group. An aromatic heterocyclic group or a fluorine atom.

L1 較好的是單鍵、亞甲基、二甲基亞甲基、二苯基亞甲基。L 1 is preferably a single bond, a methylene group, a dimethylmethylene group or a diphenylmethylene group.

R1 、R3 、R4 表示氫原子或取代基。當R1 、R3 、R4 表示取代基時，取代基可使用作為連結基L1 的取代基而舉出的取代基。R1 、R3 、R4 較好的是氫原子、烷基、芳基、胺基、烷氧基、芳氧基、雜環氧基、醯基、烷氧基羰基、芳氧基羰基、烷硫基、芳硫基、雜環硫基、磺醯基、鹵素原子、氰基、雜環基、矽烷基、矽烷氧基，更好的是氫原子、烷基、芳基、胺基、烷氧基、醯基、烷硫基、磺醯基、鹵素原子、氰基、雜環基、矽烷基，進而較好的是氫原子、烷基、芳基、烷氧基、醯基、磺醯基、氟原子、氰基、雜環基、矽烷基，進而較好的是氫原子、烷基、芳基、磺醯基、氟原子、氰基、雜環基，尤其好的是氫原子、烷基、芳基、氟原子、氰基、雜環基。最好的是氫原子、烷基、氟原子、氟烷基、氰基。該些取代基亦可進一步經其他基所取代。R 1 , R 3 and R 4 represent a hydrogen atom or a substituent. When R 1 , R 3 and R 4 represent a substituent, a substituent which is a substituent of the linking group L 1 may be used as the substituent. R 1 , R 3 and R 4 are preferably a hydrogen atom, an alkyl group, an aryl group, an amine group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a decyl group, an alkoxycarbonyl group or an aryloxycarbonyl group. An alkylthio group, an arylthio group, a heterocyclic thio group, a sulfonyl group, a halogen atom, a cyano group, a heterocyclic group, a decyl group, a decyloxy group, more preferably a hydrogen atom, an alkyl group, an aryl group, an amine group, Alkoxy group, mercapto group, alkylthio group, sulfonyl group, halogen atom, cyano group, heterocyclic group, decyl group, and further preferably a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a decyl group, a sulfonyl group A mercapto group, a fluorine atom, a cyano group, a heterocyclic group, a decyl group, and more preferably a hydrogen atom, an alkyl group, an aryl group, a sulfonyl group, a fluorine atom, a cyano group or a heterocyclic group, and particularly preferably a hydrogen atom. An alkyl group, an aryl group, a fluorine atom, a cyano group or a heterocyclic group. The most preferred are a hydrogen atom, an alkyl group, a fluorine atom, a fluoroalkyl group or a cyano group. These substituents may also be further substituted by other groups.

R2 表示取代基。由R2 所表示的取代基可使用作為由R1 、R3 、R4 所表示的取代基而舉出的取代基。由R2 所表示的取代基較好的是烷基、芳基、胺基、烷氧基、芳氧基、雜環氧基、醯基、烷氧基羰基、芳氧基羰基、烷硫基、芳硫基、雜環硫基、磺醯基、鹵素原子、氰基、雜環基、矽烷基、矽烷氧基，更好的是烷基、芳基、胺基、烷氧基、醯基、烷硫基、磺醯基、鹵素原子、氰基、雜環基、矽烷基，進而較好的是烷基、芳基、烷氧基、醯基、磺醯基、氟原子、氰基、雜環基、矽烷基，進而較好的是烷基、芳基、磺醯基、氟原子、氰基、雜環基，尤其好的是烷基、芳基、氟原子、氰基、雜環基。最好的是烷基、氟原子、氟烷基、氰基。該些取代基亦可經其他基進一步取代。R 2 represents a substituent. As the substituent represented by R 2 , a substituent exemplified as a substituent represented by R 1 , R 3 or R 4 can be used. The substituent represented by R 2 is preferably an alkyl group, an aryl group, an amine group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a decyl group, an alkoxycarbonyl group, an aryloxycarbonyl group or an alkylthio group. , arylthio, heterocyclic thio, sulfonyl, halogen, cyano, heterocyclic, decyl, decyloxy, more preferably alkyl, aryl, amine, alkoxy, fluorenyl , an alkylthio group, a sulfonyl group, a halogen atom, a cyano group, a heterocyclic group, a decyl group, and more preferably an alkyl group, an aryl group, an alkoxy group, a fluorenyl group, a sulfonyl group, a fluorine atom, a cyano group, A heterocyclic group, a decyl group, and more preferably an alkyl group, an aryl group, a sulfonyl group, a fluorine atom, a cyano group or a heterocyclic group, and particularly preferably an alkyl group, an aryl group, a fluorine atom, a cyano group or a heterocyclic ring. base. Most preferred are alkyl groups, fluorine atoms, fluoroalkyl groups, and cyano groups. These substituents may also be further substituted by other groups.

包含以通式(16)所表示的部分結構的四牙配位基的鉑錯合物較好的是以通式(17)所表示的鉑錯合物。The platinum complex containing a tetradentate ligand having a partial structure represented by the general formula (16) is preferably a platinum complex represented by the general formula (17).

通式(17)中，Z1 及Z2 表示以氮原子而配位在鉑上的含氮雜環。Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。L1 、L2 以及L3 表示單鍵或連結基。R1 、R3 、R4 表示氫原子或取代基，R2 表示取代基。In the formula (17), Z 1 and Z 2 each represent a nitrogen-containing heterocyclic ring which is coordinated to platinum by a nitrogen atom. Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 represent a single bond or a linking group. R 1 , R 3 and R 4 represent a hydrogen atom or a substituent, and R 2 represents a substituent.

對通式(17)進行說明。Z1 及Z2 與通式(16)中的Z1 同義，且較佳範圍亦相同。Z1 與Z2 可相同亦可不同。L1 、L2 以及L3 與通式(16)中的L1 同義，且較佳範圍亦相同。L1 、L2 、L3 分別可相同亦可不同。Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基。The general formula (17) will be described. Z 1 and Z 2 are synonymous with Z 1 in the formula (16), and the preferred ranges are also the same. Z 1 and Z 2 may be the same or different. L 1 , L 2 and L 3 are synonymous with L 1 in the formula (16), and the preferred ranges are also the same. L 1 , L 2 and L 3 may be the same or different. Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom.

以碳原子而鍵結在鉑上的Q2 ，例如可舉出亞胺基、芳香族烴基(苯基、萘基等)、芳香族雜環基(吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、***環、咪唑環、吡唑環、噻吩環、呋喃環等)以及含有該些基的稠環。該些基亦可經進一步取代。Examples of Q 2 bonded to platinum by a carbon atom include an imido group, an aromatic hydrocarbon group (such as a phenyl group or a naphthyl group), and an aromatic heterocyclic group (a pyridine ring, a pyrazine ring, a pyrimidine ring, and an anthracene). a azine ring, a triazine ring, a triazole ring, an imidazole ring, a pyrazole ring, a thiophene ring, a furan ring, etc.) and a fused ring containing the same. These groups can also be further substituted.

以氮原子而鍵結在鉑上的Q2 ，例如可舉出含氮雜環基(吡咯環、吡唑環、咪唑環、***環等)、胺基(烷胺基、芳胺基、醯基胺基、烷氧基羰基胺基、芳氧基羰基胺基、磺醯基胺基等)。該些基亦可經進一步取代。Examples of Q 2 bonded to platinum by a nitrogen atom include a nitrogen-containing heterocyclic group (pyrrole ring, pyrazole ring, imidazole ring, triazole ring, etc.), an amine group (alkylamino group, arylamine group, A mercaptoamine group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, etc.). These groups can also be further substituted.

以氧原子而鍵結在鉑上的Q2 ，例如可舉出氧基、羰氧基、烷氧基、芳氧基、雜環氧基、醯氧基、矽烷氧基等。The Q 2 which is bonded to the platinum by an oxygen atom may, for example, be an oxy group, a carbonyloxy group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a decyloxy group or a decyloxy group.

以硫原子而鍵結在鉑上的Q2 ，例如可舉出硫基、烷硫基、芳硫基、雜環硫基、羰硫基等。The Q 2 which is bonded to the platinum by a sulfur atom may, for example, be a sulfur group, an alkylthio group, an arylthio group, a heterocyclic thio group or a carbonylthio group.

以磷原子而鍵結在鉑上的Q2 ，例如可舉出二芳基膦基。The Q 2 which is bonded to the platinum by a phosphorus atom may, for example, be a diarylphosphino group.

由Q2 所表示的基較好的是以碳而鍵結在鉑上的芳香族烴基、以碳而鍵結在鉑上的芳香族雜環基、以氮而鍵結在鉑上的含氮雜環基、芳氧基、羰氧基，更好的是以碳而鍵結在鉑上的芳香族烴基、以碳而鍵結在鉑上的芳香族雜環基、芳氧基、羰氧基，進而較好的是以碳而鍵結在鉑上的芳香族烴基、以碳而鍵結在鉑上的芳香族雜環基、羰氧基。若可能，Q2 亦可具有取代基。取代基可使用作為通式(16)中的連結基L1 的取代基而舉出的取代基。The group represented by Q 2 is preferably an aromatic hydrocarbon group bonded to platinum on carbon, an aromatic heterocyclic group bonded to platinum by carbon, and a nitrogen-containing nitrogen bonded to platinum. a heterocyclic group, an aryloxy group, a carbonyloxy group, more preferably an aromatic hydrocarbon group bonded to platinum on carbon, an aromatic heterocyclic group bonded to platinum on carbon, an aryloxy group, a carbonyloxy group Further, the group is preferably an aromatic hydrocarbon group bonded to platinum by carbon, an aromatic heterocyclic group bonded to platinum with carbon, or a carbonyloxy group. If possible, Q 2 may also have a substituent. As the substituent, a substituent exemplified as the substituent of the linking group L 1 in the formula (16) can be used.

R1 、R2 、R3 以及R4 與通式(16)中的R1 、R2 、R3 以及R4 同義，且較佳範圍亦相同。R 1, R 2, R 3 and R 4 in the general formula (16) R 1, R 2, R 3 and R 4 are synonymous, and preferred ranges are also the same.

以通式(17)所表示的鉑錯合物較好的是以通式(18)所表示的鉑錯合物。The platinum complex represented by the formula (17) is preferably a platinum complex represented by the formula (18).

通式(18)中，Q2 表示以碳原子、氧原子、硫原子、氮原子、磷原子而鍵結在鉑上的基。L1 、L2 以及L3 表示單鍵或連結基。R1 、R3 、R4 表示氫原子或取代基，R2 表示取代基。Ra 、Rb 表示取代基，n、m表示0～3的整數。In the formula (18), Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. L 1 , L 2 and L 3 represent a single bond or a linking group. R 1 , R 3 and R 4 represent a hydrogen atom or a substituent, and R 2 represents a substituent. R a and R b represent a substituent, and n and m represent an integer of 0 to 3.

對通式(18)進行說明。Q2 、L1 、L2 、L3 、R1 、R2 、R3 、R4 與通式(17)中的Q2 、L1 、L2 、L3 、R1 、R2 、R3 、R4 同義，且較佳範圍亦相同。Ra 及Rb 表示氫原子或取代基。取代基可使用作為L1 的取代基而舉出的取代基。Ra 、Rb 較好的是氫原子、烷基、芳基、胺基、烷氧基、氟原子，更好的是烷基、芳基，進而較好的是烷基。n及m表示0～3的整數。The general formula (18) will be described. Q 2 , L 1 , L 2 , L 3 , R 1 , R 2 , R 3 , R 4 and Q 2 , L 1 , L 2 , L 3 , R 1 , R 2 , R in the formula (17) 3 , R 4 is synonymous, and the preferred range is also the same. R a and R b represent a hydrogen atom or a substituent. As the substituent, a substituent which is a substituent of L 1 can be used. R a and R b are preferably a hydrogen atom, an alkyl group, an aryl group, an amine group, an alkoxy group or a fluorine atom, more preferably an alkyl group or an aryl group, and still more preferably an alkyl group. n and m represent an integer of 0 to 3.

以通式(17)所表示的鉑錯合物較好的是以通式(19)所表示的鉑錯合物。The platinum complex represented by the formula (17) is preferably a platinum complex represented by the formula (19).

通式(19)中，Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基。L1 、L2 以及L3 表示單鍵或連結基。R1 、R3 、R4 表示氫原子或取代基，R2 表示取代基。Ra 、Rb 表示取代基，h、m表示0～3的整數。In the formula (19), Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom. L 1 , L 2 and L 3 represent a single bond or a linking group. R 1 , R 3 and R 4 represent a hydrogen atom or a substituent, and R 2 represents a substituent. R a and R b represent a substituent, and h and m represent an integer of 0 to 3.

對通式(19)進行說明。L1 、L2 、L3 、R1 、R2 、R3 、R4 、Ra 、Rb 、n以及m與通式(18)中的L1 、L2 、L3 、R1 、R2 、R3 、R4 、Ra 、Rb 、n以及m同義，且較佳範圍亦相同。Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基。以碳原子而鍵結在鉑上的Q4 ，可舉出苯環、吡啶環、嘧啶環、噠嗪環、吡嗪環、***環、吡唑環、咪唑環、噻吩環、呋喃環、或者該些環的苯幷稠環、吡啶幷稠環等。以氮原子而鍵結在鉑上的Q4 ，可舉出吡咯環、咪唑環、吡唑環、***環、或者該些環的苯幷稠環、吡啶幷稠環等。若可能，Q4 亦可具有取代基。取代基可使用作為通式(16)中的連結基L1 的取代基而舉出的取代基。The general formula (19) will be described. L 1 , L 2 , L 3 , R 1 , R 2 , R 3 , R 4 , R a , R b , n and m and L 1 , L 2 , L 3 , R 1 in the formula (18), R 2 , R 3 , R 4 , R a , R b , n and m are synonymous, and the preferred ranges are also the same. Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom. The Q 4 bonded to the platinum by a carbon atom may, for example, be a benzene ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazole ring, a pyrazole ring, an imidazole ring, a thiophene ring or a furan ring. Or a benzoquinone fused ring, a pyridinium fused ring or the like of the rings. The Q 4 bonded to the platinum by a nitrogen atom may, for example, be a pyrrole ring, an imidazole ring, a pyrazole ring or a triazole ring, or a benzoquinone fused ring or a pyridinium fused ring of the rings. If possible, Q 4 may also have a substituent. As the substituent, a substituent exemplified as the substituent of the linking group L 1 in the formula (16) can be used.

以通式(19)所表示的鉑錯合物中較佳形態之一為以通式(20)所表示的鉑錯合物。One of the preferred forms of the platinum complex represented by the formula (19) is a platinum complex represented by the formula (20).

通式(20)中，L1 、L2 以及L3 表示單鍵或連結基。R1 、R3 、R4 、R5 、R7 、R8 表示氫原子或取代基，R2 、R6 表示取代基。Ra 、Rb 表示取代基，n、m表示0～3的整數。In the formula (20), L 1 , L 2 and L 3 represent a single bond or a linking group. R 1 , R 3 , R 4 , R 5 , R 7 and R 8 represent a hydrogen atom or a substituent, and R 2 and R 6 represent a substituent. R a and R b represent a substituent, and n and m represent an integer of 0 to 3.

對通式(20)進行說明。L1 、L2 、L3 、R1 、R2 、R3 、R4 、Ra 、Rb 、n以及m與通式(19)中的L1 、L2 、L3 、R1 、R2 、R3 、R4 、Ra 、Rb 、n以及m同義，且較佳範圍亦相同。R5 、r6 、R7 、R8 與R1 、R2 、R3 、R4 同義，且較佳範圍亦相同，分別可相同亦可不同。The general formula (20) will be described. L 1 , L 2 , L 3 , R 1 , R 2 , R 3 , R 4 , R a , R b , n and m and L 1 , L 2 , L 3 , R 1 in the formula (19), R 2 , R 3 , R 4 , R a , R b , n and m are synonymous, and the preferred ranges are also the same. R 5 , r 6 , R 7 and R 8 have the same meanings as R 1 , R 2 , R 3 and R 4 , and preferably have the same range, and may be the same or different.

以下，舉出以通式(16)～(20)所表示的化合物的具體例，但本發明並不限定於該些化合物。Specific examples of the compounds represented by the general formulae (16) to (20) are given below, but the present invention is not limited to these compounds.

＜主體材料＞<main material>

本發明中的發光層較好的是含有主體材料。The light-emitting layer in the present invention preferably contains a host material.

本發明中的發光層較好的是含有電子傳輸性發光材料作為發光材料，且含有電洞傳輸性主體材料作為主體材料。亦可進一步含有電子傳輸性主體材料。The light-emitting layer in the present invention preferably contains an electron-transporting light-emitting material as a light-emitting material and contains a hole transporting host material as a host material. It may further contain an electron transporting host material.

《電洞傳輸性主體材料》"Transmission of the main body of the hole"

作為本發明的有機層中所使用的電洞傳輸性主體材料，就耐久性提高且驅動電壓降低的觀點而言，游離電位(ionization potential)Ip較好的是大於等於5.1eV且小於等於6.4eV，更好的是大於等於5.4eV且小於等於6.2eV，進而較好的是大於等於5.6eV且小於等於6.0eV。另外，就耐久性提高且驅動電壓降低的觀點而言，電子親和力(electron affinity)Ea較好的是大於等於1.2eV且小於等於3.1eV，更好的是大於等於1.4eV且小於等於3.0eV，進而較好的是大於等於1.8eV且小於等於2.8eV。As a hole transporting host material used in the organic layer of the present invention, the ionization potential Ip is preferably 5.1 eV or more and 6.4 eV or less from the viewpoint of improvement in durability and reduction in driving voltage. More preferably, it is 5.4 eV or more and 6.2 eV or less, and further preferably 5.6 eV or more and 6.0 eV or less. Further, from the viewpoint of improvement in durability and reduction in driving voltage, the electron affinity Ea is preferably 1.2 eV or more and 3.1 eV or less, more preferably 1.4 eV or more and 3.0 eV or less. Further preferably, it is 1.8 eV or more and 2.8 eV or less.

作為上述電洞傳輸性主體材料，例如具體可舉出以下材料。Specific examples of the hole transporting host material include the following materials.

可舉出：吡咯、咔唑、氮雜咔唑、吡唑、吲哚、氮雜吲哚、咪唑、聚芳基烷烴(polyarylalkane)、吡唑啉(pyrazoline)、吡唑啉酮(pyrazolone)、苯二胺(phenylenediamine)、芳基胺(arylamine)、經胺基取代的查耳酮(chalcone)、苯乙烯基蒽、芴酮(fluorenone)、腙(hydrazone)、均二苯乙烯(stilbene)、矽氮烷(silazane)、芳香族三級胺化合物、苯乙烯基胺化合物、芳香族二次甲基系化合物、卟啉(porphyrin)系化合物、聚矽烷系化合物、聚(N-乙烯基咔唑)、苯胺系共聚物、噻吩寡聚物(oligomer)、聚噻吩等的導電性高分子寡聚物，有機矽烷，碳膜，以及該些化合物的衍生物等。There may be mentioned: pyrrole, carbazole, azacarbazole, pyrazole, anthracene, azaindole, imidazole, polyarylalkane, pyrazoline, pyrazolone, Phenylenediamine, arylamine, amine-substituted chalcone, styryl fluorene, fluorenone, hydrazone, stilbene, Silazane, aromatic tertiary amine compound, styrylamine compound, aromatic secondary methyl compound, porphyrin compound, polydecane compound, poly(N-vinylcarbazole) An electrically conductive polymer oligomer such as an aniline copolymer, a thiophene oligomer or a polythiophene, an organic decane, a carbon film, or a derivative of these compounds.

其中，較好的是咔唑衍生物、吲哚衍生物、咪唑衍生物、芳香族三級胺化合物或者噻吩衍生物，尤其好的是在分子內具有多個咔唑骨架及/或吲哚骨架及/或芳香族三級胺骨架的化合物。Among them, preferred are carbazole derivatives, anthracene derivatives, imidazole derivatives, aromatic tertiary amine compounds or thiophene derivatives, and it is particularly preferred to have a plurality of carbazole skeletons and/or anthracene skeletons in the molecule. And/or a compound of an aromatic tertiary amine skeleton.

作為此種電洞傳輸性主體材料的具體化合物，例如可舉出下述化合物，但並不限定於該些化合物。Specific examples of such a hole transporting host material include, but are not limited to, the following compounds.

《電子傳輸性主體材料》"Electronic Transmission Subject Material"

本發明的有機EL元件亦可與電洞傳輸性主體材料一併含有電子傳輸性主體材料。The organic EL device of the present invention may contain an electron transporting host material together with the hole transporting host material.

本發明中所使用的電子傳輸性主體材料，就耐久性提高且驅動電壓降低的觀點而言，電子親和力Ea較好的是大於等於2.5eV且小於等於3.5eV，更好的是大於等於2.6eV且小於等於3.4eV，進而較好的是大於等於2.8eV且小於等於3.3eV。另外，就耐久性提高且驅動電壓降低的觀點而言，游離電位Ip較好的是大於等於5.7eV且小於等於7.5eV，更好的是大於等於5.8eV且小於等於7..0eV，進而較好的是大於等於5.9eV且小於等於6.5eV。In the electron-transporting host material used in the present invention, the electron affinity Ea is preferably 2.5 eV or more and 3.5 eV or less, more preferably 2.6 eV or more, from the viewpoint of improvement in durability and reduction in driving voltage. It is 3.4 eV or less, and more preferably 2.8 eV or more and 3.3 eV or less. Further, in terms of improvement in durability and reduction in driving voltage, the free potential Ip is preferably 5.7 eV or more and 7.5 eV or less, more preferably 5.8 eV or more and 7.0.0 eV or less. Preferably, it is 5.9 eV or more and 6.5 eV or less.

此種電子傳輸性主體材料，例如具體可舉出以下材料。Specific examples of such an electron transporting host material include the following materials.

可舉出：吡啶、嘧啶、三嗪、咪唑、吡唑、***、噁唑、噁二唑、芴酮、蒽醌二甲烷(anthraquinodimethane)、蒽酮(anthrone)、聯苯醌(diphenylquinone)、噻喃二氧化物(thiopyrandioxide)、碳二醯亞胺(carbodiimide)、亞芴基甲烷(fluorenylidene methane)、二苯乙烯基吡嗪、經氟取代的芳香族化合物、萘、芘(perylene)等的雜環四羧酸酐，酞菁(phthalocyanine)，以及該些化合物的衍生物(亦可與其他環形成稠環)，8-羥基喹啉(8-quinolinol)衍生物的金屬錯合物，金屬酞菁(metal phthalocyanine)，由將苯幷噁唑或苯幷噻唑作為配位基的金屬錯合物所代表的各種金屬錯合物等。There may be mentioned: pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, anthrone, anthraquinodimethane, anthrone, diphenylquinone, Thiopyrantiioxide, carbodiimide, fluorenylidene methane, distyrylpyrazine, fluorine-substituted aromatic compound, naphthalene, perylene, etc. Heterocyclic tetracarboxylic anhydride, phthalocyanine, and derivatives of these compounds (which may also form fused rings with other rings), metal complexes of 8-quinolinol derivatives, metal ruthenium Metal phthalocyanine, various metal complexes represented by metal complexes containing benzoxazole or benzothiazole as a ligand.

電子傳輸性主體材料較好的是金屬錯合物、唑(azole)衍生物(苯幷咪唑衍生物、咪唑幷吡啶衍生物等)、嗪(azine)衍生物(吡啶衍生物、嘧啶衍生物、三嗪衍生物等)，其中，本發明中就耐久性方面而言，較好的是金屬錯合物。金屬錯合物(A)更好的是具有配位在金屬上的含有至少一個氮原子或氧原子或硫原子的配位基的金屬錯合物。The electron transporting host material is preferably a metal complex, an azole derivative (benzimidazole derivative, imidazolium pyridine derivative, etc.), a azine derivative (pyridine derivative, pyrimidine derivative, A triazine derivative or the like), among which, in the present invention, a metal complex is preferred in terms of durability. More preferably, the metal complex (A) is a metal complex having a ligand coordinated to the metal containing at least one nitrogen atom or an oxygen atom or a sulfur atom.

金屬錯合物中的金屬離子並無特別限定，較好的是鈹離子、鎂離子、鋁離子、鎵離子、鋅離子、銦離子、錫離子、鉑離子或者鈀離子，更好的是鈹離子、鋁離子、鎵離子、鋅離子、鉑離子或者鈀離子，進而較好的是鋁離子、鋅離子或者鈀離子。The metal ion in the metal complex is not particularly limited, and is preferably cerium ion, magnesium ion, aluminum ion, gallium ion, zinc ion, indium ion, tin ion, platinum ion or palladium ion, more preferably cerium ion. Aluminum ion, gallium ion, zinc ion, platinum ion or palladium ion, and more preferably aluminum ion, zinc ion or palladium ion.

上述金屬錯合物中所含的配位基存在各種公知的配位基，例如可舉出「Photochemistry and Photophysics of Coordination Compounds」，Springer-Verlag出版社，H. Yersin著，1987年發行；「有機金屬化學-基礎與應用-」，裳華房出版社，山本明夫著，1982年發行等中記載的配位基。There are various known ligands in the ligand contained in the above metal complex, and examples thereof include "Photochemistry and Photophysics of Coordination Compounds", Springer-Verlag, H. Yersin, issued in 1987; Metal Chemistry - Foundations and Applications -", Sang Hua Fang Publishing House, Yamamoto Akio, Co., Ltd., issued in 1982, etc.

上述配位基較好的是含氮雜環配位基(較好的是碳數為1～30，更好的是碳數為2～20，尤其好的是碳數為3～15，可為單牙配位基，亦可為雙牙以上的配位基。較好的是雙牙以上且六牙以下的配位基。另外，雙牙以上且六牙以下的配位基與單牙的混合配位基亦較佳。The above ligand is preferably a nitrogen-containing heterocyclic ligand (preferably, the carbon number is from 1 to 30, more preferably from 2 to 20 carbon atoms, particularly preferably from 3 to 15 carbon atoms). It is a single-dentate ligand, and may be a ligand above two teeth. It is preferably a ligand of more than two teeth and less than six teeth. In addition, a ligand of more than two teeth and less than six teeth and a single tooth Mixed ligands are also preferred.

作為配位基，例如可舉出：嗪配位基(例如可舉出吡啶配位基、聯吡啶基(bipyridyl)配位基、以及三聯吡啶(terpyridine)配位基等)、羥苯基唑配位基(例如可舉出羥苯基苯幷咪唑配位基、羥苯基苯幷噁唑配位基、羥苯基咪唑配位基、羥苯基咪唑幷吡啶配位基等)、烷氧基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～10，例如可舉出甲氧基、乙氧基、丁氧基以及2-乙基己氧基等)、芳氧基配位基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯氧基、1-萘氧基、2-萘氧基、2,4,6-三甲基苯氧基以及4-聯苯氧基等)。Examples of the ligand include a azine ligand (for example, a pyridine ligand, a bipyridyl ligand, and a terpyridine ligand), and hydroxyphenyl azole. a ligand (for example, a hydroxyphenylbenzimidazole ligand, a hydroxyphenylbenzoxazole ligand, a hydroxyphenylimidazole ligand, a hydroxyphenylimidazolium pyridine ligand, etc.), an alkane The oxy ligand (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 10, and examples thereof include a methoxy group and an ethoxy group. , butoxy group, 2-ethylhexyloxy group, etc.), aryloxy ligand (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number) Examples of 6 to 12 include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 2,4,6-trimethylphenoxy group, and a 4-biphenyloxy group.

雜芳氧基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶氧基、吡嗪氧基、嘧啶氧基以及喹啉氧基等)、烷硫基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出甲硫基、乙硫基等)、芳硫基配位基(較好的是碳數為6～30，更好的是碳數為6～20，尤其好的是碳數為6～12，例如可舉出苯硫基等)、雜芳硫基配位基(較好的是碳數為1～30，更好的是碳數為1～20，尤其好的是碳數為1～12，例如可舉出吡啶硫基、2-苯幷咪唑硫基、2-苯幷噁唑硫基以及2-苯并噻唑硫基等)、矽烷氧基配位基(較好的是碳數為1～30，更好的是碳數為3～25，尤其好的是碳數為6～20，例如可舉出三苯基矽烷氧基、三乙氧基矽烷氧基以及三異丙基矽烷氧基等)、芳香族烴陰離子配位基(較好的是碳數為6～30，更好的是碳數為6～25，尤其好的是碳數為6～20，例如可舉出苯基陰離子、萘基陰離子以及蒽基陰離子等)、芳香族雜環陰離子配位基(較好的是碳數為1～30，更好的是碳數為2～25，尤其好的是碳數為2～20，例如可舉出吡咯陰離子、吡唑陰離子、吡唑陰離子、***陰離子、噁唑陰離子、苯幷噁唑陰離子、噻唑陰離子、苯幷噻唑陰離子、噻吩陰離子以及苯幷噻吩陰離子等)、假吲哚陰離子配位基等，較好的是含氮雜環配位基、芳氧基配位基、雜芳氧基或者矽烷氧基配位基，進而較好的是含氮雜環配位基、芳氧基配位基、矽烷氧基配位基、芳香族烴陰離子配位基或者芳香族雜環陰離子配位基。a heteroaryloxy ligand (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number of from 1 to 12, and examples thereof include a pyridyloxy group and a pyridyl group; Alkoxy group, or an alkylthio group (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 1 to 20, particularly preferably a carbon number) 1 to 12, for example, a methylthio group or an ethylthio group, and an arylthio group (preferably, the carbon number is 6 to 30, more preferably the carbon number is 6 to 20, particularly preferably The carbon number is 6 to 12, for example, a phenylthio group or the like, and a heteroarylthio ligand (preferably, the number of carbon atoms is 1 to 30, and more preferably the carbon number is 1 to 20, especially Preferably, the carbon number is from 1 to 12, and examples thereof include a pyridylthio group, a 2-phenylimidazoliumthio group, a 2-benzoxazolethio group, a 2-benzothiazolylthio group, and the like, and a decyloxy group. The base (preferably having a carbon number of from 1 to 30, more preferably a carbon number of from 3 to 25, particularly preferably a carbon number of from 6 to 20, and examples thereof include a triphenyldecyloxy group and a triethoxy group. Alkoxy group and triisopropyldecyloxy group, an aromatic hydrocarbon anion ligand (preferably, the carbon number is 6 to 30, more preferably The carbon number is 6 to 25, particularly preferably the carbon number is 6 to 20, and examples thereof include a phenyl anion, a naphthyl anion, and a fluorenyl anion, and an aromatic heterocyclic anion ligand (preferably The carbon number is from 1 to 30, more preferably from 2 to 25 carbon atoms, particularly preferably from 2 to 20 carbon atoms, and examples thereof include pyrrole anion, pyrazole anion, pyrazole anion, triazole anion, and oxazole. Anion, benzoxazole anion, thiazole anion, benzothiazole anion, thiophene anion, benzoquinone anion, etc.), pseudoanthracene anion ligand, etc., preferably a nitrogen-containing heterocyclic ligand, aryloxy group a ligand, a heteroaryloxy or a decyloxy ligand, more preferably a nitrogen-containing heterocyclic ligand, an aryloxy ligand, a decyloxy ligand, an aromatic hydrocarbon anionic ligand Or an aromatic heterocyclic anion ligand.

金屬錯合物電子傳輸性主體材料的例子，例如可舉出日本專利特開2002-235076、日本專利特開2004-214179、日本專利特開2004-221062、日本專利特開2004-221065、日本專利特開2004-221068、日本專利特開2004-327313等中記載的化合物。Examples of the metal complex electron-transporting host material include, for example, Japanese Patent Laid-Open No. 2002-235076, Japanese Patent Laid-Open No. 2004-214179, Japanese Patent Laid-Open No. 2004-221062, Japanese Patent Laid-Open No. 2004-221065, and Japanese Patent. The compound described in JP-A-2004-221068, JP-A-2004-327313, and the like.

此種電子傳輸性主體材料，例如具體可舉出以下材料，但並不限定於該些材料。Specific examples of such an electron transporting host material include, but are not limited to, the following materials.

電子傳輸層主體材料較好的是E-1～E-6、E-8、E-9、E-21或者E-22，更好的是E-3、E-4、E-6、E-8、E-9、E-10、E-21或者E-22，進而較好的是E-3、E-4、E-21或者E-22。The electron transport layer host material is preferably E-1 to E-6, E-8, E-9, E-21 or E-22, more preferably E-3, E-4, E-6, E. -8, E-9, E-10, E-21 or E-22, and more preferably E-3, E-4, E-21 or E-22.

＜膜厚＞<film thickness>

作為發光層的膜厚，就亮度不均、驅動電壓、亮度的觀點而言，較好的是厚度小於等於100nm的層，進而較好的是5nm～70nm，尤其好的是10nm～50nm。The film thickness of the light-emitting layer is preferably a layer having a thickness of 100 nm or less, more preferably 5 nm to 70 nm, particularly preferably 10 nm to 50 nm, from the viewpoints of unevenness in luminance, driving voltage, and brightness.

若發光層的膜厚較薄，則可進行高亮度且低電壓的驅動，但由於元件電阻變小，故易受到由電壓降低所造成的亮度變化的影響，結果導致亮度不均的增加。若發光層的膜厚較厚，則驅動電壓變高，導致發光效率的降低，而成為限定用途的原因。When the thickness of the light-emitting layer is thin, high-luminance and low-voltage driving can be performed. However, since the element resistance is small, it is susceptible to a change in luminance caused by a voltage drop, and as a result, uneven brightness is caused. When the film thickness of the light-emitting layer is thick, the driving voltage is increased, resulting in a decrease in luminous efficiency, which is a cause of limited use.

＜層構成＞<layer composition>

發光層可為一層，亦可為兩層以上，各層可以不同的發光色進行發光。而且，當發光層為積層結構時，構成積層結構的各層的膜厚並無特別限定，較好的是各發光層的總計膜厚為上述範圍。The luminescent layer may be one layer or two or more layers, and each layer may emit light in different luminescent colors. Further, when the light-emitting layer has a laminated structure, the thickness of each layer constituting the laminated structure is not particularly limited, and it is preferred that the total thickness of each of the light-emitting layers is within the above range.

(電洞注入層、電洞傳輸層)(hole injection layer, hole transmission layer)

電洞注入層、電洞傳輸層為具有自陽極或陽極側接收電洞並傳輸至陰極側的功能的層。可用於本發明的電洞注入層、電洞傳輸層的材料，除本發明的聯鎖型(interlock)化合物外，可使用其他的電洞注入材料、電洞傳輸材料。該些電洞注入材料、電洞傳輸材料可為低分子化合物，亦可為高分子化合物。The hole injection layer and the hole transport layer are layers having a function of receiving a hole from the anode or the anode side and transmitting it to the cathode side. Materials which can be used in the hole injection layer and the hole transport layer of the present invention can be used in addition to the interlocking compound of the present invention, and other hole injecting materials and hole transporting materials can be used. The hole injecting material and the hole transporting material may be a low molecular compound or a high molecular compound.

具體而言，較好的是含有以下化合物的層：吡咯衍生物、咔唑衍生物、***衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基烷烴衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳基胺衍生物、經胺基取代的查耳酮衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、均二苯乙烯衍生物、矽氮烷衍生物、芳香族三級胺化合物、苯乙烯基胺化合物、芳香族二次甲基系化合物、酞菁系化合物、卟啉系化合物、噻吩衍生物、有機矽烷衍生物、或者碳等。Specifically, a layer containing a pyrrole derivative, a carbazole derivative, a triazole derivative, an oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, or the like is preferable. Pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amine-substituted chalcone derivatives, styrylpurine derivatives, anthrone derivatives, anthracene derivatives , stilbene derivative, decazane derivative, aromatic tertiary amine compound, styrylamine compound, aromatic secondary methyl compound, phthalocyanine compound, porphyrin compound, thiophene derivative , an organic decane derivative, or carbon.

本發明的有機EL元件的電洞注入層或電洞傳輸層中可含有電子接受性摻雜劑。導入至電洞注入層或電洞傳輸層中的電子接受性摻雜劑，只要為電子接受性且具有將有機化合物氧化的性質，則可使用無機化合物，亦可使用有機化合物。The electron injection dopant may be contained in the hole injection layer or the hole transport layer of the organic EL device of the present invention. The electron-accepting dopant introduced into the hole injection layer or the hole transport layer may be an inorganic compound or an organic compound as long as it is electron-accepting and has a property of oxidizing the organic compound.

具體而言，無機化合物可舉出氯化鐵、氯化鋁、氯化鎵、氯化銦、五氯化銻等的鹵化金屬；五氧化釩及三氧化鉬等的金屬氧化物等。Specific examples of the inorganic compound include metal halides such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride; and metal oxides such as vanadium pentachloride and molybdenum trioxide.

在有機化合物的情況下，可適宜使用含有硝基、鹵素、氰基、三氟甲基等作為取代基的化合物，醌系化合物、酸酐系化合物、富勒烯(fullerene)等。In the case of an organic compound, a compound containing a nitro group, a halogen, a cyano group, a trifluoromethyl group or the like as a substituent, an anthraquinone compound, an acid anhydride compound, a fullerene or the like can be suitably used.

除此以外，可適宜使用日本專利特開平6-212153、日本專利特開平11-111463、日本專利特開平11-251067、日本專利特開2000-196140、日本專利特開2000-286054、日本專利特開2000-315580、日本專利特開2001-102175、日本專利特開2001-160493、日本專利特開2002-252085、日本專利特開2002-56985、日本專利特開2003-157981、日本專利特開2003-217862、日本專利特開2003-229278、日本專利特開2004-342614、日本專利特開2005-72012、日本專利特開2005-166637、日本專利特開2005-209643等中記載的化合物。In addition, Japanese Patent Laid-Open No. Hei 6-212153, Japanese Patent Laid-Open No. Hei 11-111463, Japanese Patent Laid-Open No. Hei 11-251067, Japanese Patent Laid-Open No. 2000-196140, Japanese Patent Laid-Open No. 2000-286054, and Japanese Patent No. Japanese Patent Laid-Open No. 2001-102175, Japanese Patent Laid-Open No. 2001-160493, Japanese Patent Laid-Open No. 2002-252085, Japanese Patent Laid-Open No. 2002-56985, Japanese Patent Laid-Open No. 2003-157981, Japanese Patent Laid-Open Publication No. 2003 -217862, a compound described in JP-A-2003-229278, JP-A-2004-342614, JP-A-2005-2012, JP-A-2005-166637, and JP-A-2005-209643.

該些電子接受性摻雜劑可單獨使用，亦可使用兩種以上。電子接受性摻雜劑的使用量根據材料的種類而不同，對於電洞傳輸層材料而言，較好的是0.01wt%～50wt%，進而較好的是0.05wt%～20wt%，尤其好的是0.1wt%～10wt%。These electron accepting dopants may be used singly or in combination of two or more. The amount of the electron-accepting dopant to be used varies depending on the kind of the material, and is preferably 0.01% by weight to 50% by weight, and more preferably 0.05% by weight to 20% by weight, particularly preferably, for the material of the hole transporting layer. It is 0.1 wt% to 10 wt%.

就降低驅動電壓的觀點而言，電洞注入層、電洞傳輸層的厚度分別較好的是小於等於500nm。The thickness of the hole injection layer and the hole transport layer is preferably equal to or less than 500 nm from the viewpoint of lowering the driving voltage.

電洞傳輸層的厚度較好的是1nm～500nm，更好的是5nm～200nm，進而較好的是10nm～100nm。另外，電洞注入層的厚度較好的是0.1nm～200nm，更好的是0.5nm～100nm，進而較好的是1nm～100nm。The thickness of the hole transport layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, still more preferably from 10 nm to 100 nm. Further, the thickness of the hole injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.5 nm to 100 nm, still more preferably from 1 nm to 100 nm.

電洞注入層、電洞傳輸層可為由上述材料的一種或者兩種以上所形成的單層結構，亦可為由相同組成或不同組成的多層所形成的多層結構。The hole injection layer and the hole transport layer may be a single layer structure formed of one or two or more of the above materials, or may be a multilayer structure formed of a plurality of layers of the same composition or different compositions.

(電子注入層、電子傳輸層)(electron injection layer, electron transport layer)

電子注入層及電子傳輸層為具有自陰極或陰極側接收電子並傳輸至陽極側的功能的層。The electron injecting layer and the electron transporting layer are layers having a function of receiving electrons from the cathode or cathode side and transmitting to the anode side.

本發明中的電子傳輸層含有以下述通式(1)所表示的含氮雜環化合物。The electron transporting layer in the present invention contains a nitrogen-containing heterocyclic compound represented by the following formula (1).

通式(1)中，A1 ～A3 相互獨立為氮原子或碳原子。Ar1 為經取代或未經取代的核碳數6～60的芳基、或者經取代或未經取代的核碳數3～60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60的伸芳基、經取代或未經取代的核碳數3～60的雜伸芳基、或者經取代或未經取代的伸芴基。R為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基，n為0～5的整數，當n大於等於2時，多個R可相同亦可不同，而且，鄰接的多個R基彼此亦可鍵結而形成碳環式脂肪族環或碳環式芳香族環。In the formula (1), A 1 to A 3 are each independently a nitrogen atom or a carbon atom. Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and Ar 2 is a hydrogen atom, substituted or not a substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or Unsubstituted alkoxy group having 1 to 20 carbon atoms. Wherein, any one of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or a substituted or unsubstituted monoheterocyclic group having 3 to 60 carbon atoms; . L 1 and L 2 are each independently a single bond, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, or Substituted or unsubstituted thiol. R is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number of 1 ～20 alkyl, or substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is 2 or more, a plurality of R may be the same or different, and Adjacent plurality of R groups may also be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.

本發明中的以通式(1)所表示的含氮雜環衍生物較好的是以下述通式(3)所表示的化合物。The nitrogen-containing heterocyclic derivative represented by the formula (1) in the present invention is preferably a compound represented by the following formula (3).

式中，A1 ～A3 分別獨立為氮原子或碳原子。In the formula, A 1 to A 3 are each independently a nitrogen atom or a carbon atom.

Ar1 為經取代或未經取代的核碳數6～60的芳基、或者經取代或未經取代的核碳數3～60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and Ar 2 is a hydrogen atom, substituted or not a substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or Unsubstituted alkoxy group having 1 to 20 carbon atoms. Wherein, any one of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or a substituted or unsubstituted monoheterocyclic group having 3 to 60 carbon atoms; .

L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60的伸芳基、經取代或未經取代的核碳數3～60的雜伸芳基、或者經取代或未經取代的伸芴基。L 1 and L 2 are each independently a single bond, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, or Substituted or unsubstituted thiol.

R'為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。R' is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number An alkyl group of 1 to 20 or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

本發明中的以通式(3)所表示的含氮雜環衍生物較好的是以下述通式(4)所表示的化合物。The nitrogen-containing heterocyclic derivative represented by the formula (3) in the present invention is preferably a compound represented by the following formula (4).

式中，A1 ～A2 分別獨立為氮原子或碳原子。In the formula, A 1 to A 2 are each independently a nitrogen atom or a carbon atom.

Ar1 為經取代或未經取代的核碳數6～60的芳基、或者經取代或未經取代的核碳數3～60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and Ar 2 is a hydrogen atom, substituted or not a substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or Unsubstituted alkoxy group having 1 to 20 carbon atoms. Wherein, any one of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or a substituted or unsubstituted monoheterocyclic group having 3 to 60 carbon atoms; .

L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60的伸芳基、經取代或未經取代的核碳數3～60的雜伸芳基、或者經取代或未經取代的伸芴基。L 1 and L 2 are each independently a single bond, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, or Substituted or unsubstituted thiol.

R'及R"分別獨立為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基，R'及R"可相同亦可不同。R' and R" are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, substituted or not The substituted alkyl group having 1 to 20 carbon atoms or the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms may have the same or different R' and R".

通式(1)、(3)～(4)中，A1 ～A3 分別獨立為氮原子或碳原子。In the general formulae (1) and (3) to (4), each of A 1 to A 3 is independently a nitrogen atom or a carbon atom.

通式(1)、(3)～(4)中，Ar1 為經取代或未經取代的核碳數6～60(較好的是核碳數6～40)的芳基、或者經取代或未經取代的核碳數3～60(較好的是核碳數3～40)的雜芳基。In the general formulae (1) and (3) to (4), Ar 1 is a substituted or unsubstituted aryl group having a core carbon number of 6 to 60 (preferably, a core carbon number of 6 to 40) or substituted. Or an unsubstituted heteroaryl group having a core carbon number of 3 to 60 (preferably, a core carbon number of 3 to 40).

Ar1 的經取代或未經取代的芳基的例子，可舉出：苯基、1-萘基、2-萘基、1-蒽基(1-anthryl)、2-蒽基、9-蒽基、1-菲基(1-phenanthryl)、2-菲基、3-菲基、4-菲基、9-菲基、1-稠四苯基(1-naphthacenyl)、2-稠四苯基、9-稠四苯基、1-蒯基(1-chrysenyl)、2-蒯基、6-蒯基、1-芘基(1-pyrenyl)、2-芘基、4-芘基、2-聯苯基、3-聯苯基、4-聯苯基、對聯三苯-4-基、對聯三苯-3-基、對聯三苯-2-基、間聯三苯-4-基、間聯三苯-3-基、間聯三苯-2-基、鄰甲苯基、間甲苯基、對甲苯基、對第三丁基苯基、對(2-苯基丙基)苯基、3-甲基-2-萘基、4-甲基-1-萘基、4-甲基-1-蒽基、4'-甲基聯苯基、4"-第三丁基對聯三苯-4-基、丙二烯合芴基(fluoranthenyl)、芴基(fluorenyl)、由螺二芴(spirobifluorene)所形成的一價基、全氟苯基(perfluorophenyl)、全氟萘基、全氟蒽基、全氟聯苯基、由9-苯基蒽所形成的一價基、由9-(1'-萘基)蒽所形成的一價基、由9-(2'-萘基)蒽所形成的一價基、由6-苯基蒯所形成的一價基、由9-[4-(二苯基胺基)苯基]蒽所形成的一價基等，較好的是苯基、萘基、聯苯基、聯三苯基、9-(10-苯基)蒽基、9-[10-(1'-萘基)]蒽基、9-[10-(2'-萘基)]蒽基等。Examples of the substituted or unsubstituted aryl group of Ar 1 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthhryl group, a 2-mercapto group, and a 9-fluorene group. 1-phenanthryl, 2-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-fused tetraphenyl , 9-fused tetraphenyl, 1-chrysenyl, 2-indenyl, 6-fluorenyl, 1-pyrenyl, 2-indenyl, 4-indenyl, 2- Biphenyl, 3-biphenyl, 4-biphenyl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-triphenyl-4-yl, inter Biphenyl-3-yl, m-triphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 3 -Methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-indenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4 - alkaloid, fluoranthenyl, fluorenyl, monovalent group formed by spirobifluorene, perfluorophenyl, perfluoronaphthyl, perfluorodecyl , perfluorobiphenyl, a monovalent group formed by 9-phenylindole, in the form of 9-(1'-naphthyl)anthracene a monovalent group, a monovalent group formed of 9-(2'-naphthyl)anthracene, a monovalent group formed of 6-phenylindole, and 9-[4-(diphenylamino) A monovalent group formed by phenyl] hydrazine, etc., preferably a phenyl group, a naphthyl group, a biphenyl group, a triphenylene group, a 9-(10-phenyl)fluorenyl group, and a 9-[10-(1' -naphthyl)]fluorenyl, 9-[10-(2'-naphthyl)]fluorenyl, and the like.

Ar1 的經取代或未經取代的雜芳基的例子，可舉出吡咯基(pyrrolyl)、呋喃基、噻吩基、矽雜環戊二烯基(silolyl)、吡啶基、喹啉基、異喹啉基、苯幷呋喃基、咪唑基、嘧啶基、咔唑基、硒吩基(selenophenyl)、噁二唑基、***基等，較好的是吡啶基、喹啉基、異喹啉基。Examples of the substituted or unsubstituted heteroaryl group of Ar 1 include a pyrrolyl group, a furyl group, a thienyl group, a silolyl group, a pyridyl group, a quinolyl group, and a different form. Quinolinyl, benzofuranyl, imidazolyl, pyrimidinyl, oxazolyl, selenophenyl, oxadiazolyl, triazolyl, etc., preferably pyridyl, quinolyl, isoquinoline base.

通式(1)、(3)～(4)中，Ar2 為氫原子、經取代或未經取代的核碳數6～60(較好的是核碳數6～40)的芳基、經取代或未經取代的核碳數3～60(較好的是核碳數3～40)的雜芳基、經取代或未經取代的碳數1～20(較好的是碳數1～6)的烷基、或者經取代或未經取代的碳數1～20(較好的是碳數1～6)的烷氧基。In the general formulae (1) and (3) to (4), Ar 2 is a hydrogen atom, a substituted or unsubstituted aryl group having a core carbon number of 6 to 60 (preferably, a core carbon number of 6 to 40), A substituted or unsubstituted heteroaryl group having a carbon number of from 3 to 60 (preferably, a core carbon number of from 3 to 40), a substituted or unsubstituted carbon number of from 1 to 20 (preferably a carbon number of 1) The alkyl group of ～6), or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms (preferably, 1 to 6 carbon atoms).

Ar2 的經取代或未經取代的芳基的例子，可舉出與上述Ar1 相同的基。Examples of the substituted or unsubstituted aryl group of Ar 2 include the same groups as the above Ar 1 .

Ar2 的經取代或未經取代的雜芳基的例子，可舉出與上述Ar1 相同的基。Examples of the substituted or unsubstituted heteroaryl group of Ar 2 include the same groups as the above Ar 1 .

Ar2 的經取代或未經取代的烷基的例子，可舉出：甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基、正庚基、正辛基、羥基甲基、1-羥基乙基、2-羥基乙基、2-羥基異丁基、1,2-二羥基乙基、1,3-二羥基異丙基、2,3-二羥基第三丁基、1,2,3-三羥基丙基、氯甲基、1-氯乙基、2-氯乙基、2-氯異丁基、1,2-二氯乙基、1,3-二氯異丙基、2,3-二氯第三丁基、1,2,3-三氯丙基、溴甲基、1-溴乙基、2-溴乙基、2-溴異丁基、1,2-二溴乙基、1,3-二溴異丙基、2,3-二溴第三丁基、1,2,3-三溴丙基、碘甲基、1-碘乙基、2-碘乙基、2-碘異丁基、1,2-二碘乙基、1,3-二碘異丙基、2,3-二碘第三丁基、1,2,3-三碘丙基、胺基甲基、1-胺基乙基、2-胺基乙基、2-胺基異丁基、1,2-二胺基乙基、1,3-二胺基異丙基、2,3-二胺基第三丁基、1,2,3-三胺基丙基、氰甲基、1-氰乙基、2-氰乙基、2-氰基異丁基、1,2-二氰乙基、1,3-二氰基異丙基、2,3-二氰基第三丁基、1,2,3-三氰基丙基、硝基甲基、1-硝基乙基、2-硝基乙基、2-硝基異丁基、1,2-二硝基乙基、1,3-二硝基異丙基、2,3-二硝基第三丁基、1,2,3-三硝基丙基、環丙基、環丁基、環戊基、環己基、4-甲基環己基、1-金剛烷基(1-adamantyl)、2-金剛烷基、1-降冰片基(1-norbornyl)、2-降冰片基等，較好的是甲基、乙基、第三丁基。Examples of the substituted or unsubstituted alkyl group of Ar 2 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a second butyl group, an isobutyl group, and a t-butyl group. N-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3 -dihydroxyisopropyl, 2,3-dihydroxy tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl 1,1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromo Ethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2, 3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2 , 3-diiodobutylidene, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1, 2-Diaminoethyl, 1,3-diaminoisopropyl, 2,3-diaminotributyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyano Ethyl, 2 - cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, 1,2,3 -Tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitrate Isopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl , 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc., preferably methyl, ethyl, tert-butyl .

Ar 2 的經取代或未經取代的烷氧基為由-OY所表示的基，Y的例子可舉出：甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基、正庚基、正辛基、羥基甲基、1-羥基乙基、2-羥基乙基、2-羥基異丁基、1,2-二羥基乙基、1,3-二羥基異丙基、2,3-二羥基第三丁基、1,2,3-三羥基丙基、氯甲基、1-氯乙基、2-氯乙基、2-氯異丁基、1,2-二氯乙基、1,3-二氯異丙基、2,3-二氯第三丁基、1,2,3-三氯丙基、溴甲基、1-溴乙基、2-溴乙基、2-溴異丁基、1,2-二溴乙基、1,3-二溴異丙基、2,3-二溴第三丁基、1,2,3-三溴丙基、碘甲基、1-碘乙基、2-碘乙基、2-碘異丁基、1,2-二碘乙基、1,3-二碘異丙基、2,3-二碘第三丁基、1,2,3-三碘丙基、胺基甲基、1-胺基乙基、2-胺基乙基、2-胺基異丁基、1,2-二胺基乙基、1,3-二胺基異丙基、2,3-二胺基第三丁基、1,2,3-三胺基丙基、氰甲基、1-氰乙基、2-氰乙基、2-氰基異丁基、1,2-二氰乙基、1,3-二氰基異丙基、2,3-二氰基第三丁基、1,2,3-三氰基丙基、硝基甲基、1-硝基乙基、2-硝基乙基、2-硝基異丁基、1,2-二硝基乙基、1,3-二硝基異丙基、2,3-二硝基第三丁基、1,2,3-三硝基丙基等，較好的是甲基、乙基、第三丁基。A r 2 by a substituted or unsubstituted alkoxy group by -OY, and examples of Y may be represented include: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butoxy Base, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1 , 2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-tri Chloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3- Dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodobutylidene, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl , 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diaminot-butyl, 1,2,3-triamine Base propyl Cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyanide Tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-di Nitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, etc., preferably methyl or ethyl , the third butyl group.

其中，通式(1)、(3)～(4)中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。In the general formulae (1) and (3) to (4), any of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or substituted or not. A substituted monoheterocyclic ring having 3 to 60 carbon atoms.

通式(1)、(3)～(4)的L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6～60(較好的是核碳數6～40)的伸芳基、經取代或未經取代的核碳數3～60(較好的是核碳數3～40)的雜伸芳基、或者經取代或未經取代的伸芴基。L 1 and L 2 of the general formulae (1) and (3) to (4) are each independently a single bond, a substituted or unsubstituted nucleus having 6 to 60 carbon atoms (preferably, a core carbon number of 6 to 40). An extended aryl group, a substituted or unsubstituted heteroaryl group having a nucleus carbon number of 3 to 60 (preferably, a core carbon number of 3 to 40), or a substituted or unsubstituted hydrazine group.

L1 及L2 的經取代或未經取代的伸芳基的例子，可舉出自與上述Ar1 相同的芳基中進一步去除氫原子而成的二價基。Examples of the substituted or unsubstituted extended aryl group of L 1 and L 2 include a divalent group obtained by further removing a hydrogen atom from the same aryl group as the above Ar 1 .

L1 及L2 的經取代或未經取代的雜伸芳基的例子，可舉出自與上述Ar1 相同的雜芳基中進一步去除氫原子而成的二價基。Examples of the substituted or unsubstituted heteroaryl group of L 1 and L 2 include a divalent group obtained by further removing a hydrogen atom from the same heteroaryl group as the above Ar 1 .

另外，通式(1)、(3)～(4)中，L1 及/或L2 較好的是選自由以下所示的二價基所組成組群中的基。Further, in the general formulae (1) and (3) to (4), L 1 and/or L 2 are preferably a group selected from the group consisting of divalent groups shown below.

而且，通式(1)、(3)～(4)中，上述Ar1 較好的是以下述通式(5)～(14)所表示的基。Further, in the general formulae (1) and (3) to (4), the above Ar 1 is preferably a group represented by the following general formulae (5) to (14).

式中，R1 ～R92 較好的是分別獨立為氫原子、鹵素原子、經取代或未經取代的碳數1～20的烷基、經取代或未經取代的碳數1～20的烷氧基、經取代或未經取代的核碳數6～40的芳氧基、經取代或未經取代的核碳數12～80的二芳胺基、經取代或未經取代的核碳數6～40的芳基、經取代或未經取代的核碳數3～40的雜芳基、或者經取代或未經取代的核碳數18～120的二芳胺基芳基，且L3 為選自由單鍵及以下所示的二價基所組成組群中的基。In the formula, R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon number of 1 to 20 carbon atoms. Alkoxy, substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 80 nucleocarbon groups, substituted or unsubstituted nuclear carbon a 6 to 40 aryl group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or a substituted or unsubstituted diarylaminoaryl group having a core number of 18 to 120, and L 3 is a group selected from the group consisting of a single bond and a divalent group shown below.

通式(1)的R為氫原子、經取代或未經取代的核碳數6～60的芳基、經取代或未經取代的核碳數3～60的雜芳基、經取代或未經取代的碳數1～20的烷基、或者經取代或未經取代的碳數1～20的烷氧基。R of the formula (1) is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, substituted or not A substituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

R的經取代或未經取代的芳基的例子，可舉出與上述Ar1 相同的基。Examples of the substituted or unsubstituted aryl group of R include the same groups as the above Ar 1 .

R的經取代或未經取代的雜芳基的例子，可舉出與上述Ar1 相同的基。Examples of the substituted or unsubstituted heteroaryl group of R include the same groups as the above Ar 1 .

R的經取代或未經取代的烷基的例子，可舉出與上述Ar2 相同的基。Examples of the substituted or unsubstituted alkyl group of R include the same groups as the above Ar 2 .

R的經取代或未經取代的烷氧基的例子，可舉出與上述Ar2 相同的基。Examples of the substituted or unsubstituted alkoxy group of R include the same groups as the above Ar 2 .

另外，n為0～5的整數，較好的是0～3，當n大於等於2時，多個R可相同亦可不同，而且，鄰接的多個R基彼此亦可鍵結而形成碳環式脂肪族環或碳環式芳香族環。Further, n is an integer of 0 to 5, preferably 0 to 3. When n is 2 or more, a plurality of R may be the same or different, and a plurality of adjacent R groups may be bonded to each other to form carbon. A cyclic aliphatic ring or a carbocyclic aromatic ring.

碳環式脂肪族環可舉出環戊烷、環己烷等的環。Examples of the carbocyclic aliphatic ring include a ring of cyclopentane or cyclohexane.

碳環式芳香族環可舉出苯、萘、菲、蒽等的環。Examples of the carbocyclic aromatic ring include a ring of benzene, naphthalene, phenanthrene, anthracene or the like.

通式(3)中，A1 ～A3 分別獨立與上述相同。In the general formula (3), A 1 to A 3 are each independently the same as described above.

通式(3)中，Ar1 及Ar2 分別獨立與上述相同，且Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。In the formula (3), Ar 1 and Ar 2 are each independently the same as described above, and any of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or substituted. Or an unsubstituted monoheterocyclic ring having 3 to 60 carbon atoms.

通式(3)中，L1 及L2 分別獨立與上述相同。In the general formula (3), L 1 and L 2 are each independently the same as described above.

通式(3)中，R'與通式(1)的R相同。In the formula (3), R' is the same as R of the formula (1).

通式(4)中，A1 ～A2 分別獨立與上述相同。In the general formula (4), A 1 to A 2 are each independently the same as described above.

通式(4)中，Ar1 及Ar2 分別獨立與上述相同，且Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10～60的稠環基、或者經取代或未經取代的核碳數3～60的單雜稠環基。In the formula (4), Ar 1 and Ar 2 are each independently the same as described above, and any of Ar 1 and Ar 2 is a substituted or unsubstituted fused ring group having a core number of 10 to 60 or substituted. Or an unsubstituted monoheterocyclic ring having 3 to 60 carbon atoms.

通式(4)中，L1 及L2 分別獨立與上述相同。In the general formula (4), L 1 and L 2 are each independently the same as described above.

通式(4)中，R'及R"分別獨立與通式(1)的R相同，且R'及R"可相同亦可不同。In the formula (4), R' and R" are each independently the same as R of the formula (1), and R' and R" may be the same or different.

以下，表示本發明的以通式(1)、(3)～(4)所表示的含氮雜環衍生物的具體例，但並不限定於該些例示化合物。Specific examples of the nitrogen-containing heterocyclic derivative represented by the general formulae (1) and (3) to (4) of the present invention are shown below, but are not limited to the above-exemplified compounds.

另外，下述表中「\」表示單鍵。In addition, "\" in the following table indicates a single key.

另外，進而較好的是含有上述含氮雜環衍生物的層含有還原性摻雜劑。Further, it is further preferred that the layer containing the nitrogen-containing heterocyclic derivative contains a reducing dopant.

還原性摻雜劑較好的是選自鹼金屬、鹼土金屬、稀土金屬、鹼金屬的氧化物、鹼金屬的鹵化物、鹼土金屬的氧化物、鹼土金屬的鹵化物、稀土金屬的氧化物、稀土金屬的鹵化物、鹼金屬的有機錯合物、鹼土金屬的有機錯合物以及稀土金屬的有機錯合物中的至少一種。The reducing dopant is preferably selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, At least one of a rare earth metal halide, an alkali metal organic complex, an alkaline earth metal organic complex, and an organic complex of a rare earth metal.

鹼金屬可舉出Li(功函數：2.90eV)、Na(功函數：2.36eV)、K(功函數：2.28eV)、銣(Rb)(功函數：2.16eV)、Cs(功函數：1.95eV)等。Examples of the alkali metal include Li (work function: 2.90 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), 铷 (Rb) (work function: 2.16 eV), and Cs (work function: 1.95) eV) and so on.

鹼土金屬可舉出Ca(功函數：2.9eV)、Sr(功函數：2.0eV～2.5eV)、Ba(功函數：2.52eV)等。Examples of the alkaline earth metal include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), and Ba (work function: 2.52 eV).

稀土金屬可舉出Sc、Y、Eu、Tb、Ce等。Examples of the rare earth metal include Sc, Y, Eu, Tb, and Ce.

鹼金屬的氧化物可舉出Li2 O、LiO、NaO等。Examples of the alkali metal oxide include Li 2 O, LiO, NaO, and the like.

鹼金屬的鹵化物可舉出LiF、NaF、KF、LiCl、KCl、NaCl等。Examples of the halide of the alkali metal include LiF, NaF, KF, LiCl, KCl, NaCl, and the like.

鹼土金屬的氧化物可舉出CaO、BaO、SrO等。Examples of the oxide of the alkaline earth metal include CaO, BaO, SrO, and the like.

鹼土金屬的鹵化物可舉出CaF2 、BaF2 、SrF2 以及BeF2 等的氟化物，以及除氟化物以外的鹵化物。The halide of the alkaline earth metal may, for example, be a fluoride such as CaF 2 , BaF 2 , SrF 2 or BeF 2 or a halide other than the fluoride.

較佳的還原性摻雜劑可舉出Li、Na、K、Rb、Cs等的鹼金屬，及Ca、Sr以及Ba等的鹼土金屬；尤其好的是功函數小於等於2.9eV的金屬。該些金屬中，更佳的還原性摻雜劑為選自由K、Rb以及Cs所組成組群中的至少一種鹼金屬，進而較好的是Rb或Cs，最好的是Cs。該些鹼金屬的還原能力特別高，故藉由添加相對少量的該些鹼金屬，即可實現有機EL元件中的發光亮度的提高及長壽命化。另外，功函數小於等於2.9eV的還原性摻雜劑，亦較好的是兩種以上的該些鹼金屬的組合，尤其好的是含有Cs的組合，例如Cs與Na、Cs與K、Cs與Rb，或者Cs、Na及K的組合。藉由組合含有Cs，可有效率地發揮還原能力，從而實現有機EL元件中的發光亮度的提高及長壽命化。Preferred examples of the reducing dopant include alkali metals such as Li, Na, K, Rb, and Cs, and alkaline earth metals such as Ca, Sr, and Ba; and particularly preferably metals having a work function of 2.9 eV or less. Among these metals, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb and Cs, and more preferably Rb or Cs, most preferably Cs. Since these alkali metals have a particularly high reducing ability, it is possible to improve the light-emitting luminance and the life of the organic EL element by adding a relatively small amount of these alkali metals. Further, a reducing dopant having a work function of 2.9 eV or less is preferably a combination of two or more of these alkali metals, and particularly preferably a combination containing Cs, such as Cs and Na, Cs and K, Cs. With Rb, or a combination of Cs, Na and K. By combining the inclusion of Cs, the reducing ability can be efficiently exhibited, and the luminance of the light emitted from the organic EL element can be improved and the life can be extended.

該些還原性摻雜劑可單獨使用，亦可使用兩種以上。還原性摻雜劑的使用量根據材料的種類而不同，對於電子傳輸層材料而言，較好的是0.1wt%～99wt%，進而較好的是1.0wt%～80wt%，尤其好的是2.0wt%～70wt%。These reducing dopants may be used singly or in combination of two or more. The amount of the reducing dopant to be used varies depending on the kind of the material, and is preferably from 0.1% by weight to 99% by weight, more preferably from 1.0% by weight to 80% by weight, particularly preferably the electron transporting layer material. 2.0 wt% to 70 wt%.

本發明中的電子傳輸層可與上述含氮雜環化合物一併使用其他的電子注入材料、電子傳輸材料。該些電子注入材料、電子傳輸材料可為低分子化合物，亦可為高分子化合物。The electron transporting layer in the present invention may be used together with the above-mentioned nitrogen-containing heterocyclic compound in combination with other electron injecting materials and electron transporting materials. The electron injecting material and the electron transporting material may be a low molecular compound or a high molecular compound.

具體而言，較好的是含有以下化合物的層：吡啶衍生物、喹啉衍生物、嘧啶衍生物、吡嗪衍生物、酞嗪衍生物、啡啉(phenanthroline)衍生物、三嗪衍生物、***衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、芴酮衍生物、蒽醌二甲烷衍生物、蒽酮衍生物、聯苯醌衍生物、噻喃二氧化物衍生物、碳二醯亞胺衍生物、亞芴基甲烷衍生物、二苯乙烯基吡嗪衍生物、萘、芘等的芳香環四羧酸酐、酞菁衍生物、8-羥基喹啉衍生物的金屬錯合物或金屬酞菁、由將苯幷噁唑或苯幷噻唑作為配位基的金屬錯合物所代表的各種金屬錯合物、由矽雜環戊二烯所代表的有機矽烷衍生物等。Specifically, a layer containing a pyridine derivative, a quinoline derivative, a pyrimidine derivative, a pyrazine derivative, a pyridazine derivative, a phenanthroline derivative, a triazine derivative, or the like is preferable. Triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, anthrone derivatives, quinodimethane derivatives, anthrone derivatives, biphenyl hydrazine derivatives, thiopyran dioxide derivatives a metal such as a carbodiimide derivative, a mercapto methane derivative, a distyryl pyrazine derivative, an anthracene tetracarboxylic anhydride such as naphthalene or an anthracene, a phthalocyanine derivative or an 8-hydroxyquinoline derivative a complex compound or a metal phthalocyanine, a metal complex represented by a metal complex containing benzoxazole or benzothiazole as a ligand, an organodecane derivative represented by a fluorenylcyclopentadiene Wait.

就降低驅動電壓的觀點而言，電子注入層、電子傳輸層的厚度分別較好的是小於等於500nm。The thickness of the electron injecting layer and the electron transporting layer is preferably equal to or less than 500 nm from the viewpoint of lowering the driving voltage.

電子傳輸層的厚度較好的是1nm～500nm，更好的是5nm～200nm，進而較好的是10nm～100nm。另外，電子注入層的厚度較好的是0.1nm～200nm，更好的是0.2nm～100nm，進而較好的是0.5nm～50nm。The thickness of the electron transporting layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, still more preferably from 10 nm to 100 nm. Further, the thickness of the electron injecting layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, still more preferably from 0.5 nm to 50 nm.

電子注入層、電子傳輸層可為由上述材料的一種或者兩種以上所形成的單層結構，亦可為由相同組成或不同組成的多層所形成的多層結構。The electron injecting layer and the electron transporting layer may be a single layer structure formed of one or two or more of the above materials, or may be a multilayer structure formed of a plurality of layers of the same composition or different compositions.

(電洞阻擋層)(hole blocking layer)

電洞阻擋層為具有防止自陽極側傳輸至發光層的電洞穿過至陰極側的功能的層。本發明中，可設置電洞阻擋層作為在陰極側與發光層鄰接的有機層。The hole blocking layer is a layer having a function of preventing a hole that is transmitted from the anode side to the light emitting layer from passing to the cathode side. In the present invention, a hole blocking layer may be provided as an organic layer adjacent to the light emitting layer on the cathode side.

構成電洞阻擋層的化合物的例子，可舉出雙(2-甲基-8-羥基喹啉)-4-(苯基苯酚)鋁(Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolate)-alum inium(III)，BAlq)等的鋁錯合物、***衍生物、2,9-二甲基-4,7-二苯基-1,10-啡啉(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline，BCP)等的啡啉衍生物等。Examples of the compound constituting the barrier layer of the hole include bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenol)aluminum (Bis-(2-methyl-8-quinolinolato)-4- (phenyl-phenolate)-alum inium (III), BAlq), etc. aluminum complex, triazole derivative, 2,9-dimethyl-4,7-diphenyl-1,10-morpholine (2 , phenanthroline derivatives such as 9-dimethyl-4,7-diphenyl-1, 10-phenanthroline, BCP).

電洞阻擋層的厚度較好的是1nm～500nm，更好的是5nm～200nm，進而較好的是10nm～100nm。The thickness of the hole blocking layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, still more preferably from 10 nm to 100 nm.

電洞阻擋層可為由上述材料的一種或者兩種以上所形成的單層結構，亦可為由相同組成或不同組成的多層所形成的多層結構。The hole blocking layer may be a single layer structure formed of one or two or more of the above materials, or may be a multilayer structure formed of a plurality of layers of the same composition or different compositions.

(電子阻擋層)(electronic barrier layer)

電子阻擋層為具有防止自陰極側傳輸至發光層的電子穿過至陽極側的功能的層。本發明中，可設置電子阻擋層作為在陽極側與發光層鄰接的有機層。The electron blocking layer is a layer having a function of preventing electrons transmitted from the cathode side to the light emitting layer from passing to the anode side. In the present invention, an electron blocking layer may be provided as an organic layer adjacent to the light-emitting layer on the anode side.

構成電子阻擋層的化合物的例子，例如可使用作為上述電洞傳輸材料而舉出的化合物。As an example of the compound constituting the electron blocking layer, for example, a compound exemplified as the above-mentioned hole transporting material can be used.

電子阻擋層的厚度較好的是1nm～500nm，更好的是5nm～200nm，進而較好的是10nm～100nm。The thickness of the electron blocking layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, still more preferably from 10 nm to 100 nm.

電洞阻擋層可為由上述材料的一種或者兩種以上所形成的單層結構，亦可為由相同組成或不同組成的多層所形成的多層結構。The hole blocking layer may be a single layer structure formed of one or two or more of the above materials, or may be a multilayer structure formed of a plurality of layers of the same composition or different compositions.

(保護層)(The protective layer)

本發明中，有機EL元件整體亦可由保護層保護。In the present invention, the entire organic EL element can also be protected by a protective layer.

保護層中所含的材料只要為具有抑制水分或氧等的促進元件劣化的物質進入至元件內的功能的化合物即可。The material contained in the protective layer may be a compound having a function of inhibiting the deterioration of the element such as moisture or oxygen into the element.

該材料的具體例可舉出：In、Sn、Pb、Au、Cu、Ag、Al、Ti或者Ni等的金屬；MgO、SiO、SiO2 、Al2 O3 、GeO、NiO、CaO、BaO、Fe2 O3 、Y2 O3 或者TiO2 等的金屬氧化物；SiNx 、SiNx Oy 等的金屬氮化物；MgF2 、LiF、AlF3 或者CaF2 等的金屬氟化物；聚乙烯、聚丙烯、聚甲基丙烯酸甲酯、聚醯亞胺、聚脲、聚四氟乙烯、聚氯三氟乙烯、聚二氟二氯乙烯、氯三氟乙烯與二氟二氯乙烯的共聚物、使含有四氟乙烯與至少一種共聚單體的單體混合物共聚合而獲得的共聚物、在共聚合主鏈上具有環狀結構的含氟共聚物、吸水率大於等於1%的吸水性物質、吸水率小於等於0.1%的防濕性物質等。Specific examples of the material include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni; MgO, SiO, SiO 2 , Al 2 O 3 , GeO, NiO, CaO, and BaO, a metal oxide such as Fe 2 O 3 , Y 2 O 3 or TiO 2 ; a metal nitride such as SiN x or SiN x O y ; a metal fluoride such as MgF 2 , LiF, AlF 3 or CaF 2 ; a copolymer of polypropylene, polymethyl methacrylate, polyimine, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydifluorodichloroethylene, chlorotrifluoroethylene and difluorodichloroethylene, a copolymer obtained by copolymerizing a monomer mixture containing tetrafluoroethylene and at least one comonomer, a fluorine-containing copolymer having a cyclic structure in a copolymerization main chain, a water-absorbent substance having a water absorption ratio of 1% or more, A moisture-proof substance or the like having a water absorption rate of 0.1% or less.

保護層的形成方法並無特別限定，例如可使用真空蒸鍍法、濺鍍法、反應性濺鍍法、分子束磊晶(molecular beam epitaxy，MBE)法、簇型離子束(cluster ion beam)法、離子電鍍法、電漿聚合法(高頻激發離子電鍍法)、電漿CVD法、雷射CVD法、熱CVD法、氣源(gas source)CVD法、塗佈法、印刷法或者轉印法。The method for forming the protective layer is not particularly limited, and for example, a vacuum deposition method, a sputtering method, a reactive sputtering method, a molecular beam epitaxy (MBE) method, or a cluster ion beam can be used. Method, ion plating method, plasma polymerization method (high frequency excitation ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method or transfer Printed.

(密封)(seal)

另外，本發明的有機電場發光元件亦可使用密封容器來密封元件整體。Further, the organic electroluminescent device of the present invention may use a sealed container to seal the entire device.

而且，亦可在密封容器與發光元件之間的空間內封入水分吸收劑或惰性液體。水分吸收劑並無特別限定，例如可舉出氧化鋇、氧化鈉、氧化鉀、氧化鈣、硫酸鈉、硫酸鈣、硫酸鎂、五氧化磷、氯化鈣、氯化鎂、氯化銅、氟化銫、氟化鈮、溴化鈣、溴化釩、分子篩(molecular sieve)、沸石(zeolite)以及氧化鎂等。惰性液體並無特別限定，例如可舉出石蠟(paraffin)類，液體石蠟(liquid paraffin)類，全氟烷烴、全氟胺、全氟醚等的氟系溶劑，氯系溶劑以及矽油(silicone oil)類。Further, a moisture absorbent or an inert liquid may be enclosed in a space between the sealed container and the light-emitting element. The moisture absorbent is not particularly limited, and examples thereof include cerium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride, and cesium fluoride. , cesium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, and magnesium oxide. The inert liquid is not particularly limited, and examples thereof include paraffin, liquid paraffin, fluorine solvent such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorine solvent, and silicone oil. )class.

(驅動)(drive)

本發明的有機電場發光元件可藉由對陽極與陰極之間施加直流(視需要亦可包含交流成分)電壓(通常為2伏～15伏)或直流電流，而獲得發光。The organic electroluminescent device of the present invention can obtain luminescence by applying a direct current (and optionally an alternating component) voltage (usually 2 volt to 15 volts) or a direct current between the anode and the cathode.

本發明的有機電場發光元件的驅動方法可使用日本專利特開平2-148687號、日本專利特開平6-301355號、日本專利特開平5-29080號、日本專利特開平7-134558號、日本專利特開平8-234685號、日本專利特開平8-241047號的各公報；日本專利第2784615號、美國專利5828429號、美國專利6023308號的各說明書等中記載的驅動方法。The driving method of the organic electroluminescent device of the present invention can be carried out by using the Japanese Patent Laid-Open No. Hei 2-148687, the Japanese Patent Laid-Open No. Hei No. Hei 6-301355, the Japanese Patent Laid-Open No. Hei 5-29080, the Japanese Patent Laid-Open No. Hei 7-134558, and the Japanese Patent. Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei.

本發明的發光元件可藉由各種公知的方法而提高光出射效率。例如可藉由以下方法來提高光的出射效率且提高外部量子效率：對基板表面形狀進行加工(例如形成微細的凹凸圖案)，對基板、ITO層、有機層的折射率進行控制，對基板、ITO層、有機層的膜厚進行控制等。The light-emitting element of the present invention can improve the light-emitting efficiency by various known methods. For example, the light emission efficiency can be improved and the external quantum efficiency can be improved by processing the surface shape of the substrate (for example, forming a fine uneven pattern), controlling the refractive index of the substrate, the ITO layer, and the organic layer, and the substrate, The film thickness of the ITO layer and the organic layer is controlled.

本發明的發光元件亦可為自陽極側出射發光的所謂頂部發光(top emission)方式。The light-emitting element of the present invention may also be a so-called top emission method in which light is emitted from the anode side.

(本發明的用途)(Use of the present invention)

本發明的有機電場發光元件可適宜用於顯示元件、顯示器(display)、背光、電子照相、照明光源、記錄光源、曝光光源、讀取光源、標識、廣告牌、室內裝飾(interior)、光通訊等。The organic electroluminescent device of the present invention can be suitably used for display elements, displays, backlights, electrophotography, illumination sources, recording sources, exposure sources, reading sources, signs, billboards, interiors, optical communications Wait.

[實例][Example]

使用實例，對本發明進行具體說明，但本發明並不限定於該些實例。The invention will be specifically described by way of examples, but the invention is not limited to the examples.

1.有機EL元件的製作1. Production of organic EL elements

比較例1Comparative example 1

將0.5mm厚、2.5cm見方的玻璃基板放入清洗容器中，在2-丙醇中進行超音波清洗後，進行30分鐘的紫外線臭氧處理(ultraviolet-ozone treatment)。然後利用真空蒸鍍法在該透明陽極上蒸鍍以下的層。本發明的實施例中的蒸鍍速度在無特別說明的情況下為0.2nm/sec。蒸鍍速度是使用晶體振盪器來測定。以下記載的膜厚亦使用晶體振盪器來測定。A 0.5 mm thick, 2.5 cm square glass substrate was placed in a cleaning container, and subjected to ultrasonic cleaning in 2-propanol, followed by ultraviolet-ozone treatment for 30 minutes. Then, the following layers were deposited on the transparent anode by vacuum evaporation. The vapor deposition rate in the examples of the present invention was 0.2 nm/sec unless otherwise specified. The vapor deposition rate was measured using a crystal oscillator. The film thickness described below was also measured using a crystal oscillator.

‧陽極：在玻璃基板上蒸鍍膜厚為100nm的ITO(Indium Tin Oxide)。‧ Anode: ITO (Indium Tin Oxide) having a film thickness of 100 nm was deposited on a glass substrate.

‧電洞注入層：在陽極(ITO)上蒸鍍膜厚為140nm的4,4',4"-三(N-(2-萘基)-N-苯基胺基)三苯基胺(4,4',4"-Tris(N-(2-naphtyl)-N-phenyl-amino)-triphenylamine，2-TNATA)。‧ Hole injection layer: 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (4) was deposited on the anode (ITO) with a thickness of 140 nm. 4',4"-Tris(N-(2-naphtyl)-N-phenyl-amino)-triphenylamine, 2-TNATA).

‧電洞傳輸層：在電洞注入層上蒸鍍膜厚為7nm的雙[N-(1-萘基)-N-苯基]聯苯胺(Bis[N-(1-naphthyl)-N-phenyl]benzidine，α-NPD)。‧ hole transport layer: bis[N-(1-naphthyl)-N-phenyl]benzidine (Bis[N-(1-naphthyl)-N-phenyl) with a thickness of 7 nm deposited on the hole injection layer ]benzidine, α-NPD).

‧第二電洞傳輸層：在電洞傳輸層上蒸鍍厚度為3nm的胺化合物1。‧Second hole transport layer: An amine compound 1 having a thickness of 3 nm was deposited on the hole transport layer.

‧發光層：在第二電洞傳輸層上蒸鍍厚度為30nm的發光層，該發光層中摻雜著電洞傳輸性主體材料N,N'-二咔唑基-3,5-苯(N,N'-dicarbazolyl-3,5-benzene，mCP)與相對於mCP而為6.0wt%的電洞傳輸性磷光發光材料三(2-苯基吡啶)銥(tris(2-phenylpyridine)iridium(III)，Ir(ppy)3 )。‧Light-emitting layer: a light-emitting layer having a thickness of 30 nm is deposited on the second hole transport layer, and the light-emitting layer is doped with a hole transporting host material N,N'-dicarbazolyl-3,5-benzene ( N,N'-dicarbazolyl-3,5-benzene,mCP) and the channel-transmitting phosphorescent material tris(2-phenylpyridine)iridium (6.0% by weight) relative to mCP III), Ir(ppy) 3 ).

‧電子傳輸層：在發光層上蒸鍍厚度為40nm的以通式(1)所表示的電子傳輸性材料含氮雜環衍生物1。‧ Electron transport layer: The electron transporting material nitrogen-containing heterocyclic derivative 1 represented by the formula (1) having a thickness of 40 nm was deposited on the light-emitting layer.

‧電子注入層：在電子傳輸層上蒸鍍厚度為1nm的LiF。‧ Electron injection layer: LiF having a thickness of 1 nm was deposited on the electron transport layer.

‧陰極：在電子傳輸層上設置圖案化的罩幕(發光區域為2mm×2mm的罩幕)，蒸鍍100nm的金屬鋁而成為陰極。‧ Cathode: A patterned mask (a 2 mm × 2 mm mask) was placed on the electron transport layer, and 100 nm of metal aluminum was vapor-deposited to form a cathode.

將所製作的積層體放入以氬氣(argon gas)進行置換的套手工作箱(glove box)內，使用不鏽鋼(stainless steel)製的密封罐及紫外線硬化型的黏接劑(XNR5516HV，Nagase-Ciba(股)製造)進行密封。The produced laminate was placed in a glove box replaced with argon gas, and a stainless steel (stainless steel) sealed can and an ultraviolet curing adhesive (XNR5516HV, Nagase) were used. - Ciba (manufactured)) for sealing.

藉此，製作比較的有機EL元件。Thereby, a comparative organic EL element was produced.

以下，表示實施例中所使用的材料的結構。Hereinafter, the structure of the material used in the examples is shown.

比較例2Comparative example 2

比較例1中，電子傳輸層使用低電子傳輸性材料BAlq(Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolate)-alum inium(III))來代替含氮雜環衍生物1，除此以外，與比較例1同樣地製作比較的有機EL元件。In Comparative Example 1, the electron transport layer uses a low electron transporting material BAlq (Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolate)-alum inium (III)) instead of the nitrogen-containing heterocyclic derivative. 1. A comparative organic EL device was produced in the same manner as in Comparative Example 1, except for the above.

比較例3Comparative example 3

比較例1中，發光層使用以通式(2)所表示的電子傳輸性磷光發光材料四牙配位基鉑錯合物1來代替Ir(ppy)3 ，且電子傳輸層使用低電子傳輸性材料BAlq(Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolate)-alum inium(III))來代替含氮雜環衍生物1，除此以外，與比較例1同樣地製作比較的有機EL元件。In Comparative Example 1, the electron-transporting phosphorescent material tetradentate ligand platinum complex 1 represented by the general formula (2) was used instead of Ir(ppy) 3 , and the electron transport layer used low electron transport property. The material BAlq (Bis-(2-methyl-8-quinolinolato)-4-(phenyl-phenolate)-alum inium (III)) was produced in the same manner as in Comparative Example 1, except that the nitrogen-containing heterocyclic derivative 1 was replaced. Comparative organic EL elements.

實例1Example 1

比較例1中，發光層使用以通式(2)所表示的作為電子傳輸性磷光發光材料的四牙配位基鉑錯合物1來代替Ir(ppy)3 ，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the tetradentate ligand platinum complex 1 which is an electron-transporting phosphorescent material represented by the general formula (2) was used instead of Ir(ppy) 3 in the light-emitting layer, and the comparative example was used. 1 The organic EL device of the present invention was produced in the same manner.

實例2Example 2

比較例1中，發光層使用以通式(2)所表示的電子傳輸性磷光發光材料四牙配位基鉑錯合物1來代替Ir(ppy)3 ，且電子傳輸層使用含氮雜環衍生物2來代替含氮雜環衍生物1，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the electron-transporting phosphorescent material tetradentate ligand platinum complex 1 represented by the general formula (2) was used instead of Ir(ppy) 3 , and the electron transport layer was a nitrogen-containing heterocyclic ring. The organic EL device of the present invention was produced in the same manner as in Comparative Example 1, except that the derivative 2 was used instead of the nitrogen-containing heterocyclic derivative 1.

實例3Example 3

比較例1中，發光層使用以通式(2)所表示的電子傳輸性磷光發光材料四牙配位基鉑錯合物1來代替Ir(ppy)3 ，且電子傳輸層使用含氮雜環衍生物3來代替含氮雜環衍生物1，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the electron-transporting phosphorescent material tetradentate ligand platinum complex 1 represented by the general formula (2) was used instead of Ir(ppy) 3 , and the electron transport layer was a nitrogen-containing heterocyclic ring. The organic EL device of the present invention was produced in the same manner as in Comparative Example 1, except that the derivative 3 was used instead of the nitrogen-containing heterocyclic derivative 1.

實例4Example 4

比較例1中，發光層使用以通式(2)所表示的電子傳輸性磷光發光材料四牙配位基鉑錯合物1來代替Ir(ppy)3 ，且電子傳輸層使用含氮雜環衍生物4來代替含氮雜環衍生物1，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the electron-transporting phosphorescent material tetradentate ligand platinum complex 1 represented by the general formula (2) was used instead of Ir(ppy) 3 , and the electron transport layer was a nitrogen-containing heterocyclic ring. The organic EL device of the present invention was produced in the same manner as in Comparative Example 1, except that the derivative 4 was used instead of the nitrogen-containing heterocyclic derivative 1.

實例5Example 5

比較例1中，發光層使用以通式(2)所表示的電子傳輸性磷光發光材料四牙配位基鉑錯合物2來代替Ir(ppy)3 ，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the same as in Comparative Example 1, except that the electron-transporting phosphorescent material tetradentate ligand platinum complex 2 represented by the formula (2) was used instead of Ir(ppy) 3 . The organic EL device of the present invention was produced.

實例6Example 6

比較例1中，發光層使用通式(2)中所包含的電子傳輸性磷光發光材料四牙配位基鉑錯合物3來代替Ir(ppy)3 ，除此以外，與比較例1同樣地製作本發明的有機EL元件。In Comparative Example 1, the electron-emitting phosphorescent luminescent material tetradentate ligand platinum complex 3 contained in the general formula (2) was used in the same manner as in Comparative Example 1, except that Ir(ppy) 3 was used instead. The organic EL device of the present invention was produced.

實例7Example 7

實例6中，發光層使用下述電洞傳輸性主體材料2來代替mCP作為電洞傳輸性主體材料，除此以外，與實例6同樣地製作本發明的有機EL元件。In the example 6, the organic EL device of the present invention was produced in the same manner as in Example 6 except that the hole-transporting host material 2 was used instead of the mCP as the hole transporting host material.

(性能評價)(Performance evaluation)

根據下述，對所獲得的本發明的有機EL元件及比較的有機EL元件檢測驅動電壓及外部量子效率。The driving voltage and the external quantum efficiency were detected for the obtained organic EL device of the present invention and the comparative organic EL device as described below.

1)驅動電壓1) Driving voltage

使用東陽技術(股)製造的電源量測單元(Source Measure Unit)2400，對各元件施加直流電壓，使各元件發光。測定亮度為1000cd/m2 時的電壓作為驅動電壓。A source voltage measurement unit (Source Measure Unit) 2400 manufactured by Dongyang Technology Co., Ltd. was used to apply a DC voltage to each element to cause each element to emit light. A voltage at a luminance of 1000 cd/m 2 was measured as a driving voltage.

2)外部量子效率2) External quantum efficiency

使用東陽技術(股)製造的電源量測單元2400，對各元件施加直流電壓，使各元件發光。使用Topcon公司製造的亮度計BM-8來測定發光的亮度。發光光譜(emission spectrum)與發光波長是使用浜松光子學(股)製造的頻譜分析儀(spectrum analyzer)PMA-11來測定。根據該些數值，利用亮度換算法來算出亮度為1000cd/m2 時的外部量子效率。A power supply measuring unit 2400 manufactured by Dongyang Technology Co., Ltd. is used to apply a DC voltage to each element to cause each element to emit light. The luminance of the luminescence was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and the emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics Co., Ltd. Based on these numerical values, the external quantum efficiency at a luminance of 1000 cd/m 2 was calculated by a luminance conversion algorithm.

將所獲得的結果示於表1。The results obtained are shown in Table 1.

在將比較例1與比較例2進行比較的情況下，當使用電洞傳輸性磷光發光材料Ir(ppy)3 時，若使電子傳輸層自低電子傳輸性材料BAlq變成高電子傳輸性材料含氮雜環衍生物1，則驅動電壓降低，且外部量子效率降低，無法同時實現磷光發光的高量子效率與低電壓化。In the case of comparing Comparative Example 1 with Comparative Example 2, when the hole transporting phosphorescent material Ir(ppy) 3 is used, if the electron transporting layer is changed from the low electron transporting material BAlq to the high electron transporting material, In the nitrogen heterocyclic derivative 1, the driving voltage is lowered, and the external quantum efficiency is lowered, and high quantum efficiency and low voltage of phosphorescence cannot be simultaneously achieved.

另一方面，若將使用電子傳輸性磷光發光材料四牙配位基鉑錯合物1的比較例3與實例1進行比較，則與電子傳輸層使用BAlq的比較例3相比，使用含氮雜環衍生物1的實例1中，在將外部量子效率維持為較高的狀態下大幅降低驅動電壓。與實例1同樣地使用三種滿足式(1)的含氮雜環衍生物的實例2～4亦獲得相同的效果。實例5～7為改變電子傳輸性磷光發光材料的種類及主體材料的種類而獲得的本發明的元件，仍可獲得相同的效果。On the other hand, when Comparative Example 3 using the electron-transporting phosphorescent material tetradentate ligand platinum complex 1 was compared with Example 1, the nitrogen content was used as compared with Comparative Example 3 in which the electron transport layer used BAlq. In Example 1 of the heterocyclic derivative 1, the driving voltage was drastically lowered in a state where the external quantum efficiency was maintained high. The same effects were obtained as in Example 1 using the three examples of the nitrogen-containing heterocyclic derivatives satisfying the formula (1) as in Example 1. Examples 5 to 7 are elements of the present invention obtained by changing the kind of the electron-transporting phosphorescent material and the kind of the host material, and the same effects can be obtained.

將2008年10月23日申請的日本專利特願2008-273308號說明書的全部內容作為參照而引用入本說明書中。The entire contents of the specification of Japanese Patent Application No. 2008-273308, filed on Jan.

雖然本發明已以實施例揭露如上，然其並非用以限定本發明，任何所屬技術領域中具有通常知識者，在不脫離本發明之精神和範圍內，當可作些許之更動與潤飾，故本發明之保護範圍當視後附之申請專利範圍所界定者為準。Although the present invention has been disclosed in the above embodiments, it is not intended to limit the invention, and any one of ordinary skill in the art can make some modifications and refinements without departing from the spirit and scope of the invention. The scope of the invention is defined by the scope of the appended claims.

Claims (14)

一種有機電場發光元件，在基板上包括一對電極與在該些電極間包含發光層及電子傳輸層的有機層，上述發光層含有電子傳輸性磷光發光材料，且在上述發光層與陰極之間包含上述電子傳輸層，上述電子傳輸層含有以下述通式(4)所表示的含氮雜環化合物，上述電子傳輸性磷光發光材料含有至少一種金屬錯合物，該金屬錯合物具有三牙以上的配位基，且該配位基為鏈狀配位基並具有以下述通式(2)所表示的部分結構： (通式(4)中，A1 及A2 相互獨立為氮原子或碳原子；Ar1 為經取代或未經取代的核碳數6~60的芳基、或者經取代或未經取代的核碳數3~60的雜芳基，Ar2 為氫原子、經取代或未經取代的核碳數6~60的芳基、經取代或未經取代的核碳數3~60的雜芳基、經取代或未經取代的碳數1~20的烷基、或者經取代或未經取代的碳數1~20的烷氧基；其中，Ar1 及Ar2 的任一者為經取代或未經取代的核碳數10~60的稠環基、或者經取代或未經取代的核碳數3~60的單雜稠環基； L1 及L2 分別獨立為單鍵、經取代或未經取代的核碳數6~60的伸芳基、經取代或未經取代的核碳數3~60的雜伸芳基、或者經取代或未經取代的伸芴基；R'及R"各自獨立為氫原子、經取代或未經取代的核碳數6~60的芳基、經取代或未經取代的核碳數3~60的雜芳基、經取代或未經取代的碳數1~20的烷基、或者經取代或未經取代的碳數1~20的烷氧基，且相互可相同亦可不同)； (通式(2)中，M11 表示金屬離子，L11 、L12 、L13 、L14 、L15 相互獨立表示配位在M11 上的配位基；在L11 、L14 之間並不進一步存在原子群而形成環狀配位基；L15 並不與L11 及L14 兩者鍵結形成環狀配位基；Y11 、Y12 、Y13 相互獨立表示連結基、單鍵或者雙鍵；L11 與Y12 、Y12 與L12 、L12 與Y11 、Y11 與L13 、L13 與Y13 、Y13 與L14 之間的鍵表示單鍵或雙鍵；n11 表示0~4)。An organic electroluminescent device comprising a pair of electrodes on a substrate and an organic layer comprising a light-emitting layer and an electron transport layer between the electrodes, wherein the light-emitting layer comprises an electron-transporting phosphorescent material, and between the light-emitting layer and the cathode The electron transporting layer comprising the nitrogen-containing heterocyclic compound represented by the following formula (4), wherein the electron-transporting phosphorescent material contains at least one metal complex having three teeth The above ligand, and the ligand is a chain ligand and has a partial structure represented by the following formula (2): (In the formula (4), A 1 and A 2 are each independently a nitrogen atom or a carbon atom; and Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or substituted or unsubstituted. a heteroaryl group having a carbon number of 3 to 60, Ar 2 being a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 60 carbon atoms. a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; wherein either of Ar 1 and Ar 2 is substituted Or an unsubstituted fused ring group having a nuclear carbon number of 10 to 60, or a substituted or unsubstituted monoheterocyclic ring group having a core number of 3 to 60; L 1 and L 2 are each independently a single bond and substituted Or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, or substituted or unsubstituted exudylene; R' and R" each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having a core number of 3 to 60, substituted or unsubstituted Alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted carbon numbers 1 to 20 Alkoxy groups, which may be the same or different from each other); (In the formula (2), M 11 represents a metal ion, and L 11 , L 12 , L 13 , L 14 and L 15 independently of each other represent a ligand coordinated to M 11 ; between L 11 and L 14 The atomic group is not further formed to form a cyclic ligand; L 15 is not bonded to both L 11 and L 14 to form a cyclic ligand; Y 11 , Y 12 and Y 13 are independent of each other to represent a linking group, Key or double bond; L 11 and Y 12 , Y 12 and L 12 , L 12 and Y 11 , Y 11 and L 13 , L 13 and Y 13 , Y 13 and L 14 represent a single bond or a double bond ;n 11 means 0~4). 如申請專利範圍第1項所述之有機電場發光元件，其 中上述電子傳輸性磷光發光材料為鉑錯合物。 An organic electric field light-emitting element according to claim 1, wherein The above electron transporting phosphorescent material is a platinum complex. 如申請專利範圍第1或2項所述之有機電場發光元件，其中以上述通式(4)所表示的含氮雜環化合物中，上述L1 及L2 相互獨立為選自以下述化學式所表示的二價基組群中的基： The organic electroluminescent device according to claim 1 or 2, wherein, in the nitrogen-containing heterocyclic compound represented by the above formula (4), the above L 1 and L 2 are independently selected from the following chemical formulas. The base in the expressed divalent group: 如申請專利範圍第1或2項所述之有機電場發光元件，其中以上述通式(4)所表示的含氮雜環化合物中，上述Ar1 及Ar2 的至少一者為以下述通式(5)~(14)所表示的基： (式中，R1 ~R92 相互獨立為氫原子、鹵素原子、經取代或未經取代的碳數1~20的烷基、經取代或未經取代的碳數1~20的烷氧基、經取代或未經取代的核碳數6~40的芳氧基、經取代或未經取代的核碳數 12~80的二芳胺基、經取代或未經取代的核碳數6~40的芳基、經取代或未經取代的核碳數3~40的雜芳基、或者經取代或未經取代的核碳數18~120的二芳胺基芳基，L3 為選自由單鍵及以下述化學式所表示的二價基所組成組群中的基： The organic electroluminescent device according to the first or second aspect of the invention, wherein, in the nitrogen-containing heterocyclic compound represented by the above formula (4), at least one of the above Ar 1 and Ar 2 is a general formula (5) The base represented by ~(14): (wherein R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 80 nucleus, substituted or unsubstituted nucleus 6~ An aryl group of 40, a substituted or unsubstituted heteroaryl group having a core carbon number of 3 to 40, or a substituted or unsubstituted diarylaminoaryl group having a core number of 18 to 120, and L 3 is selected from A single bond and a group consisting of a divalent group represented by the following chemical formula: 如申請專利範圍第3項所述之有機電場發光元件，其中以上述通式(4)所表示的含氮雜環化合物中，上述Ar1 及Ar2 的至少一者為以下述通式(5)~(14)所表示的基： (式中，R1 ~R92 相互獨立為氫原子、鹵素原子、經取代或未經取代的碳數1~20的烷基、經取代或未經取代的碳數1~20的烷氧基、經取代或未經取代的核碳數6~40的芳氧基、經取代或未經取代的核碳數 12~80的二芳胺基、經取代或未經取代的核碳數6~40的芳基、經取代或未經取代的核碳數3~40的雜芳基、或者經取代或未經取代的核碳數18~120的二芳胺基芳基，L3 為選自由單鍵及以下述化學式所表示的二價基所組成組群中的基： The organic electroluminescent device according to the third aspect of the invention, wherein, in the nitrogen-containing heterocyclic compound represented by the above formula (4), at least one of the above Ar 1 and Ar 2 is a formula (5) ) The base represented by ~(14): (wherein R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 80 nucleus, substituted or unsubstituted nucleus 6~ An aryl group of 40, a substituted or unsubstituted heteroaryl group having a core carbon number of 3 to 40, or a substituted or unsubstituted diarylaminoaryl group having a core number of 18 to 120, and L 3 is selected from A single bond and a group consisting of a divalent group represented by the following chemical formula: 如申請專利範圍第1項所述之有機電場發光元件，其中上述電子傳輸性磷光發光材料包含以下述通式(15)所表示的部分結構： (通式(15)中，M21 表示金屬離子，Y21 表示連結基、單鍵或者雙鍵；Y22 、Y23 相互獨立表示單鍵或連結基； Q21 、Q22 相互獨立表示形成含氮雜環的原子群，由Q21 所形成的環與Y21 之間的鍵及由Q22 所形成的環與Y21 之間的鍵表示單鍵或雙鍵；X21 、X22 相互獨立表示氧原子、硫原子、經取代或未經取代的氮原子；R21 、R22 、R23 、R24 相互獨立表示氫原子或取代基，R21 及R22 以及R23 及R24 亦可分別鍵結而形成環；L25 表示配位在M21 上的配位基；n21 表示0~4的整數)。The organic electroluminescence device according to claim 1, wherein the electron-transporting phosphorescent material comprises a partial structure represented by the following formula (15): (In the formula (15), M 21 represents a metal ion, Y 21 represents a linking group, a single bond or a double bond; and Y 22 and Y 23 each independently represent a single bond or a linking group; and Q 21 and Q 22 independently represent each other to form a The atomic group of the nitrogen heterocycle, the bond between the ring formed by Q 21 and Y 21 and the bond formed between Q 22 and Y 21 represent a single bond or a double bond; X 21 and X 22 are independent of each other And an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom; R 21 , R 22 , R 23 , and R 24 each independently represent a hydrogen atom or a substituent, and R 21 and R 22 and R 23 and R 24 may also Each of the bonds is bonded to form a ring; L 25 represents a ligand coordinated to M 21 ; n 21 represents an integer of 0 to 4). 如申請專利範圍第6項所述之有機電場發光元件，其中包含四牙配位基的至少一種鉑錯合物來作為上述電子傳輸性磷光發光材料，該鉑錯合物包含以下述通式(16)所表示的部分結構： (通式(16)中，Z1 表示以氮原子而配位在鉑上的含氮雜環；L1 表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基)。An organic electroluminescent device according to claim 6, wherein at least one platinum complex comprising a tetradentate ligand is used as the electron transporting phosphorescent material, and the platinum complex comprises the following formula ( 16) Part of the structure represented: (In the formula (16), Z 1 represents a nitrogen-containing heterocyclic ring coordinated to platinum by a nitrogen atom; L 1 represents a single bond or a linking group; and R 1 , R 3 and R 4 independently of each other represent a hydrogen atom or a substituent. A group, R 2 represents a substituent). 如申請專利範圍第7項所述之有機電場發光元件，其中包含以上述通式(16)所表示的部分結構的四牙配位基的鉑錯合物，為以下述通式(17)所表示的鉑錯合物： (通式(17)中，Z1 及Z2 相互獨立表示以氮原子而配位在鉑上的含氮雜環；Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基)。The organic electroluminescent device according to claim 7, wherein the platinum complex comprising a tetradentate ligand having a partial structure represented by the above formula (16) is represented by the following formula (17) The platinum complex represented: (In the formula (17), Z 1 and Z 2 independently of each other represent a nitrogen-containing heterocyclic ring coordinated to a platinum atom; and Q 2 represents a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom; a group bonded to platinum; L 1 , L 2 and L 3 independently of each other represent a single bond or a linking group; R 1 , R 3 and R 4 independently of each other represent a hydrogen atom or a substituent, and R 2 represents a substituent). 如申請專利範圍第8項所述之有機電場發光元件，其中以上述通式(17)所表示的鉑錯合物，為以下述通式(18)所表示的鉑錯合物： (通式(18)中，Q2 表示以碳原子、氧原子、硫原子、氮原子或者磷原子而鍵結在鉑上的基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0~3的整數)。The organic electroluminescent device according to claim 8, wherein the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (18): (In the formula (18), Q 2 represents a group bonded to platinum by a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom; and L 1 , L 2 and L 3 independently represent a single bond or a linkage; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3). 如申請專利範圍第8項所述之有機電場發光元件，其中以上述通式(17)所表示的鉑錯合物，為以下述通式(19)所表示的鉑錯合物： (通式(19)中，Q4 表示以碳原子或氮原子而鍵結在鉑上的芳香族烴環基或芳香族雜環基；L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0~3的整數)。The organic electroluminescent device according to claim 8, wherein the platinum complex represented by the above formula (17) is a platinum complex represented by the following formula (19): (In the formula (19), Q 4 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group bonded to platinum by a carbon atom or a nitrogen atom; and L 1 , L 2 and L 3 independently of each other represent a single bond or The linking group; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a and R b each independently represent a substituent, and n and m each independently represent an integer of 0 to 3). 如申請專利範圍第10項所述之有機電場發光元件，其中以上述通式(19)所表示的鉑錯合物，為以下述通式(20)所表示的化合物： (通式(20)中，L1 、L2 以及L3 相互獨立表示單鍵或連結基；R1 、R3 、R4 相互獨立表示氫原子或取代基，R2 表示取代基；Ra 、Rb 相互獨立表示取代基，n、m相互獨立表示0~3的整數；R5 、R7 、R8 相互獨立表示氫原子或取代基，R6 表示取代基)。The organic electroluminescent device according to claim 10, wherein the platinum complex represented by the above formula (19) is a compound represented by the following formula (20): (In the formula (20), L 1 , L 2 and L 3 each independently represent a single bond or a linking group; R 1 , R 3 and R 4 each independently represent a hydrogen atom or a substituent, and R 2 represents a substituent; R a R b and independently represent a substituent, and n and m each independently represent an integer of 0 to 3; R 5 , R 7 and R 8 each independently represent a hydrogen atom or a substituent, and R 6 represents a substituent). 如申請專利範圍第1項所述之有機電場發光元件，其中上述發光層包含電洞傳輸性主體材料。 The organic electroluminescent device according to claim 1, wherein the light-emitting layer comprises a hole transporting host material. 如申請專利範圍第1項所述之有機電場發光元件，其中上述含有含氮雜環化合物的電子傳輸層包含還原性摻雜劑。 The organic electroluminescence device according to claim 1, wherein the electron transport layer containing the nitrogen-containing heterocyclic compound contains a reducing dopant. 如申請專利範圍第13項所述之有機電場發光元件，其中上述還原性摻雜劑為選自由鹼金屬、鹼土金屬、稀土金屬、鹼金屬的氧化物、鹼金屬的鹵化物、鹼土金屬的氧化物、鹼土金屬的鹵化物、稀土金屬的氧化物、稀土金屬的鹵化物、鹼金屬的有機錯合物、鹼土金屬的有機錯合物以及稀土金屬的有機錯合物所組成組群中的至少一種。 The organic electroluminescent device according to claim 13, wherein the reducing dopant is selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, and an alkaline earth metal. At least a group of a substance, an alkaline earth metal halide, a rare earth metal oxide, a rare earth metal halide, an alkali metal organic complex, an alkaline earth metal organic complex, and an organic complex of a rare earth metal One.
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