JP5612359B2 - Organic electroluminescence device - Google Patents

Description

  The present invention relates to an organic electroluminescent element (light emitting element or EL element) that can emit light by converting electric energy into light.

Today, research and development on various display elements are active. Among them, organic electroluminescence (EL) elements are attracting attention as promising display elements because they can emit light with high luminance at a low voltage.
In general, an organic EL element is composed of a light emitting layer or a counter electrode sandwiching a plurality of organic layers including a light emitting layer, and electrons injected from a cathode and holes injected from an anode are recombined in the light emitting layer, One that uses light emission from the generated exciton, or one that uses light emission from the exciton of another molecule generated by energy transfer from the exciton.
However, this organic electroluminescent element has a very low luminous efficiency compared to inorganic LED elements and fluorescent tubes, which is a big problem. Most of the organic electroluminescent devices currently proposed utilize fluorescence emitted from singlet excitons of an organic compound luminescent material. In the mechanism of simple quantum chemistry, in the exciton state, the ratio of singlet excitons that give fluorescence emission and triplet excitons that give phosphorescence emission is 1: 3, as long as fluorescence emission is used. Only 25% of the excitons can be effectively used, resulting in low emission efficiency. On the other hand, if phosphorescence obtained from triplet excitons can be used, the luminous efficiency can be improved. In recent years, a phosphorescent light emitting element using an iridium phenylpyridine complex has been reported (for example, see Non-Patent Document 1). In these reports, the luminous efficiency of 2 to 3 times that of conventional organic light-emitting devices using fluorescence is reported. However, this is still low in terms of energy saving and durability improvement, and further improvement in luminous efficiency and luminance are strongly demanded.

  Although an invention related to a phosphorescent organic EL device using a metal complex as a host material has been disclosed (see, for example, Patent Document 1), luminous efficiency and durability are not yet sufficient, and high luminous luminance and luminous efficiency are achieved. The development of an element that is excellent in durability is shown.

As a phosphorescent light emitting element emitting red light, an element using a platinum porphyrin complex having a cyclic tetradentate ligand as a light emitting material is known (for example, see Non-patent Document 2 and Patent Document 2). Improvements have been sought due to low brightness.
In addition, platinum porphyrin complexes having a chain bipyridine-based or phenanthroline-based tetradentate ligand have been reported (for example, see Non-patent Document 3, Patent Document 3, and Patent Document 4), color purity, and the like. The light emitting characteristics and durability are not compatible, and improvements have been desired. In addition, there has been a demand for the development of green and blue light emitting materials with shorter wavelengths that are further excellent in light emission characteristics and durability.

JP 2004-214179 A US Pat. No. 6,303,231 B1 US Pat. No. 6,653,654 B1 International Publication No. 03 / 093283A1 Pamphlet

Appl. Phys. Lett. , 75 (1999) 4 Nature 395, 151 (1998) Chem. Eur. J. et al. , 9, No. 6,1264 (2003)

  An object of the present invention is to provide an organic EL device that exhibits high luminous efficiency and excellent durability.

( 1) An organic electroluminescence device having an organic compound layer including at least one light emitting layer between a pair of electrodes, the light emitting layer including at least one light emitting material and at least one host material. And the light emitting material is a metal complex having a tridentate or higher ligand, and the host material is a metal complex represented by the following general formula (H-1). element,

(In the formula, X ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, which may have a substituent if possible, and is a constituent atom of another ring. Y ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, and may have a substituent if possible, or may be a constituent atom of another ring. M ¹ represents a metal ion, n ¹ represents an integer of 1 or more, L ^H represents a ligand, m ¹ represents an integer of 0 or more, Q ^H1 represents X ^H1 , Y ^H1 , M ¹ And a group of atoms that form a chelate ring together with a single bond, double bond, triple bond, or coordination bond, but the bond between Q ^{H1 and} X ^H1 And the bond between Q ^{H1 and} Y ^H1 is not a coordination bond.)
(2) The organic electroluminescent element according to item (1), wherein the ligand of the metal complex of the luminescent material is a chain ligand,
(3) At least one selected from the group consisting of platinum ions, iridium ions, rhenium ions, palladium ions, rhodium ions, ruthenium ions, copper ions, europium ions, gadolinium ions, and terbium ions. The organic electroluminescent element according to any one of (1) and (2),
(4) The organic electroluminescent element according to any one of (1) to (3), wherein the metal complex of the luminescent material is a metal complex that emits phosphorescence.
(5) The organic electroluminescent device according to any one of (1) to (4), wherein the metal complex of the luminescent material is a compound represented by the general formula (1),

(M ¹¹ represents a metal ion, and L ¹¹ , L ¹² , L ¹³ , L ¹⁴ , and L ¹⁵ each represent a ligand that coordinates to M ^11. There is an additional atomic group between L ¹¹ and L ^14. L ¹⁵ does not combine with both L ¹¹ and L ¹⁴ to form a cyclic ligand, Y ¹¹ , Y ¹² and Y ¹³ are each a linking group, A 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 , and Y ¹³ and L ¹⁴ represents a single bond or a double bond. Represents a single bond or a double bond, and n ¹¹ represents 0 to 4.)
(6) The organic electroluminescent element according to any one of (1) to (5), wherein the metal complex of the luminescent material is a compound represented by the general formula (2),

(M ²¹ represents a metal ion, 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 represent nitrogen-containing hetero groups, respectively. represents an atomic group forming a ring, the bond between the ring and Y ²¹ which are formed by binding and Q ²² between the ring and Y ²¹ formed by Q ²¹ represents a single bond or a double bond .X ²¹ , X ²² each represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, R ²¹ , R ²² , R ²³ , and R ²⁴ each represent a hydrogen atom or a substituent, and R ^21, R ²² , and R ²³ And R ²⁴ may combine with each other to form a ring, L ²⁵ represents a ligand coordinated to M ²¹ , and n ²¹ represents an integer of 0 to 4.)
(7) The metal complex of the luminescent material is represented by the general formula (2), the rings formed by Q ²¹ and Q ²² are each a pyridine ring, and Y ²¹ represents a linking group composed of one or more atoms. An organic electroluminescent device according to item (6), which is a compound;
(8) The metal complex is represented by the general formula (2), and the rings formed by Q ²¹ and Q ²² are each a pyridine ring, Y ²¹ is a single bond or a double bond, and X ²¹ and X ²² are And an organic electroluminescent device as described in the item (6), which is a compound representing a sulfur atom or a substituted or unsubstituted nitrogen atom,
(9) The organic electric field according to item (6), wherein the metal complex is represented by the general formula (2), and the rings formed by Q ²¹ and Q ²² are each a nitrogen-containing hetero 5-membered ring. Light emitting element,
(10) The metal complex is represented by the general formula (2), and the rings formed by Q ²¹ and Q ²² are each a nitrogen-containing 6-membered ring containing two or more nitrogen atoms (6 ) Organic electroluminescent device according to item
(11) The organic electroluminescent element according to any one of (1) to (5), wherein the metal complex is a compound represented by the general formula (9),

(M ^A1 represents a metal ion, Q ^A1 and Q ^A2 each represent an atomic group forming a nitrogen-containing heterocycle. R ^A1 , R ^A2 , R ^A3 and R ^A4 each represents a hydrogen atom or a substituent, ^A1 and R ^A2 and R ^A3 and R ^A4 may be bonded to each other to form a ring, Y ^A2 and Y ^A3 each represent a linking group or a single bond, and Y ^A1 is two bidentate coordination in parentheses. And represents a linking group, a single bond, or a double bond for linking each child, L ^A5 represents a ligand coordinated to M ^A1 , and n ^A1 represents an integer of 0 to 4.)
(12) The organic electroluminescent element according to item (11), wherein the metal complex of the luminescent material is a compound represented by the general formula (11),

(R ^C1 and R ^C2 each represent a hydrogen atom or a substituent, and R ^C3 , R ^C4 , R ^C5 and R ^C6 each represent a substituent. N ^C3 and n ^C6 represent 0 to 3, n ^C4 and n ^C5 represent represents an integer of 0 to 4, when having a plurality of ^{R C3, R C4, R C5} , R C6 , respectively, the plurality of ^{R C3, R C4, R C5} , R C6 may be the same or different , May be linked to form a ring.)
(13) The organic electroluminescent element according to any one of (1) to (5), wherein the metal complex of the luminescent material is a compound represented by the general formula (10),

(M ^B1 represents a metal ion, Y ^B1 represents a linking group. Y ^B2 and Y ^B3 each represent a linking group or a single bond. X ^B1 and X ^B2 represent an oxygen atom, a sulfur atom, a substituted or unsubstituted group, respectively. Represents a nitrogen atom, and n ^B1 and n ^B2 represent an integer of 0 to 1. R ^B1 , R ^B2 , R ^B3 , R ^B4 , R ^B5 , and R ^B6 each represents a hydrogen atom or a substituent, and R ^B1 and R ^{B B2} and R ^B3 and R ^B4 may be bonded to each other to form a ring, L ^B5 represents a ligand coordinated to M ^B1 , n ^B3 represents an integer of 0 to 4, provided that Y ^B1 Is not linked to R ^B5 or R ^B6 .)
(14) The organic electroluminescent element according to item (13), wherein the metal complex of the luminescent material is a compound represented by the general formula (12),

(R ^D3 and R ^D4 each represent a hydrogen atom or a substituent, and R ^D1 and R ^D2 each represent a substituent. N ^D1 and n ^D2 each represent an integer of 0 to 4, and R ^D1 and R ^D2 each represent a plurality of R ^D1 and R ^D2. In the case of having one, a plurality of R ^D1 and R ^D2 may be the same or different, and may be connected to form a ring, Y ^D1 is a vinyl group substituted at the 1- or 2-position, a phenylene ring, Represents a pyridine ring, a pyrazine ring, a pyrimidine ring or a methylene group having 1 to 8 carbon atoms.)
(15) The organic electroluminescent element according to any one of (1) to (5), wherein the metal complex of the luminescent material is a compound represented by the general formula (8),

(M ⁸¹ represents a metal ion, and L ⁸¹ , L ⁸² , L ⁸³ , and L ⁸⁵ each represent a ligand that coordinates to M ^{81. An} atomic group further exists between L ⁸¹ and L ⁸³ to form a ring or It does not form a tetradentate or higher ligand, L ⁸⁵ does not connect to L ⁸¹ or L ⁸³ without a metal, Y ⁸¹ and Y ⁸² each represent a linking group, a single bond, or a double bond. It represents a bond .n ⁸¹ represents an integer of 0 to 3.)
(16) The metal complex of the luminescent material is represented by the general formula (8), and L ⁸¹ , L ⁸² , and L ⁸³ are carbon atoms and are aromatic hydrocarbon rings or heterocycles coordinated to M ⁸¹ , or nitrogen atoms represents coordinating nitrogen-containing heterocyclic ring M ^81, L ^81, at least one of L ^82, L ⁸³ is characterized in that it is a nitrogen-containing hetero ring (15) the organic electroluminescent device according to claim,
(17) The organic electroluminescent element according to any one of (1) to (5), wherein the metal complex of the luminescent material is represented by the general formula (X1),

(In the general formula ^(X1), M X1 .L is .Q ^X11 to Q ^X16 representing a metal ion represents a atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^{X1 X11} ~L ^X14 Represents a single bond, a double bond or a linking group, that is, an atomic group consisting of Q ^X11 -L ^X11 -Q ^X12 -L ^X12 -Q ^X13 and Q ^X14 -L ^X13 -Q ^X15 -L ^X14 -Q ^X16 Each atomic group is a tridentate ligand. The bond between M ^X1 and Q ^{X11 to} Q ^X16 may be a coordinate bond or a covalent bond.)
(18) The organic electroluminescent element according to item (17), wherein the metal complex represented by the general formula (X1) is represented by the general formula (X2),

(In the general formula (X2), M ^X2 is .Y ^X21 to Y ^X26 representing a metal ion represents a coordinating atom M ^X2, Q ^X21 ~Q ^X26 is an aromatic ring or aromatic with each Y ^X21 to Y ^X26 .L ^X21 ~L ^X24 representing an atom group forming a family heterocycle single bond, the bond between .M ^X2 and Y ^X21 to Y ^X26 representing a double bond or a linking group can be a covalent bond at each coordinate bond Good.)
(19) The organic electroluminescent element according to item (17), wherein the metal complex represented by the general formula (X1) is represented by the general formula (X3),

(In the general formula (X3), M ^X3 represents a metal ion. Y ^X31 to Y ^X36 represent a carbon atom, a nitrogen atom or a phosphorus atom. L ^{X31 to} L ^X34 represent a single bond, a double bond or a linking group. (The bond between M ^X3 and Y ^X31 to Y ^X36 may be a coordinate bond or a covalent bond.)
(20) The organic electroluminescent element according to any one of (1) to (19), wherein the metal complex that functions as a host material is represented by the following general formula (H-2) or (H-3):

(In the formula, X ^H2 represents an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, and may have a substituent if possible. Y ^H2 represents an oxygen atom, a nitrogen atom, or a sulfur atom. if possible may have a substituent group .Z ^H21, Z ^H22 and Z ^H23 represents a carbon atom or a nitrogen atom, if possible may have a substituent group .Q ^H21 and Q ^H22 represents .L ^H ligand is .n ² .M ² is representing a metal ion represents an atomic group necessary for forming a five- or six-membered ring represents an integer of 1 or more, m ² Represents an integer of 0 or more, and the bond type between each atom in the formula may be any of a single bond, a double bond, a triple bond, and a coordination bond, provided that a bond between Z ^{H21 and} X ^H2 and Q ^H21 bond between the bond between the at least one and Z ^H23 -Y ^H2 bond between -X ^H2 is not a coordinate bond.)

(In the formula, X ^H3 represents an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, and may have a substituent if possible. Y ^H3 represents an oxygen atom, a nitrogen atom, or a sulfur atom. Z ^H31 , Z ^H32 and Z ^{H33 each} represents a carbon atom or a nitrogen atom, and if possible, may have a substituent, Q ^H31 and Q ^H32 .L ^H is .M ³ represent the atoms necessary to form a five- or six-membered ring representing a .n ³ is an integer of 1 or more representing a metal ion represents a ligand, m ³ Represents an integer of 0 or more, and the bond type between each atom in the formula may be any of a single bond, a double bond, a triple bond, and a coordination bond, provided that a bond between Z ^{H31 and} X ^H3 and Q ^H31 coupling between at least one of the coupling between the -X ^H3 and Z ^H32 -Y ^H3 is not a coordinate bond.)
(21) The organic electroluminescent element according to any one of (1) to (20), wherein the metal complex that functions as a host material is represented by the following general formula (H-4):

(In the formula, X ^H41 and X ^H42 each represent a carbon atom or a nitrogen atom. The bond between X ^H41 and the nitrogen atom, and the bond between X ^H42 and the carbon atom represents a single bond or a double bond. Q ^H41 and Q ^H42 are Each represents a group of atoms necessary for forming a 5-membered or 6-membered ring, M ⁴ represents a metal ion, n ⁴ represents an integer of 1 or more, L ^H represents a ligand, and m ⁴ represents 0 or more. Represents an integer.)
(22) The organic electroluminescent element according to any one of (1) to (21), wherein the metal complex that functions as a host material is represented by the following general formula (H-5):

(In the formula, R ^H51 and R ^H52 represent a hydrogen atom or a substituent. Z ^H5 represents an oxygen atom, a sulfur atom, —C (R ^H53 ) R ^H54 —, or —NR ^H55 —. R ^H53 , R ^H54 And R ^H55 represents a hydrogen atom or a substituent, Q ^H5 represents an atomic group necessary to form a 5-membered ring or a 6-membered ring, M ⁵ represents a metal ion, and n ⁵ represents an integer of 1 or more. L ^H represents a ligand, and m ⁵ represents an integer greater than or equal to 0. The bond type between each atom in the formula may be any of a single bond, a double bond, a triple bond, and a coordination bond.
(23) The organic electroluminescent element according to any one of (1) to (22), wherein the metal complex that functions as a host material is represented by the following general formula (H-6):

（一般式（Ｘ３）中、Ｍ ^X3 は金属イオンを表す。Ｙ ^X31 〜Ｙ ^X36 は、炭素原子、窒素原子、リン原子を表す。Ｌ ^X31 〜Ｌ ^X34 は単結合、二重結合または連結基を表す。Ｍ ^X3 とＹ ^X31 〜Ｙ ^X36 との結合は、それぞれ配位結合でも共有結合でもよい。）

（式中、Ｒ^H51、Ｒ^H52は水素原子または置換基を表す。Ｚ^H5は酸素原子、硫黄原子、−Ｃ（Ｒ^H53）Ｒ^H54−、または−ＮＲ^H55−を表す。Ｒ^H53、Ｒ^H54およびＲ^H55は水素原子または置換基を表す。Ｑ^H5は５員環または６員環を形成するのに必要な原子群を表す。Ｍ⁵は金属イオンを表す。ｎ⁵は１以上の整数を表す。Ｌ^Hは配位子を表し、ｍ⁵は０以上の整数を表す。式中の各原子間の結合種は単結合、二重結合、三重結合、配位結合のいずれでもよい。）
（２）前記一般式（Ｘ３）におけるＹ ^Ｘ３１ 〜Ｙ ^Ｘ３６ が、炭素原子または窒素原子である（１）に記載の有機電界発光素子。
（３）前記一般式（Ｘ３）におけるＹ ^Ｘ３１ 、Ｙ ^Ｘ３３ 、Ｙ ^Ｘ３５ が窒素原子であり、Ｙ ^Ｘ３２ 、Ｙ ^Ｘ３４ およびＹ ^Ｘ３６ が、炭素原子である（１）または（２）に記載の有機電界発光素子。
（４）ホスト材料として機能する金属錯体が、下記一般式（Ｈ−６）で表される（１）〜（３）のいずれか１項に記載の有機電界発光素子。

（式中、Ｚ^H6は酸素原子、硫黄原子、−Ｃ（Ｒ^H63）Ｒ^H64−、または−ＮＲ^H65−を表す。Ｒ^H63、Ｒ^H64およびＲ^H65は水素原子または置換基を表す。Ｑ^H61は５員環または６員環を形成するのに必要な原子群を表す。Ｑ^H62はヘテロ環を形成するのに必要な原子群を表す。Ｍ⁶は金属イオンを表す。ｎ⁶は１以上の整数を表す。Ｌ^Hは配位子を表し、ｍ⁶は０以上の整数を表す。式中の各原子間の結合種は単結合、二重結合、三重結合、配位結合のいずれでもよい。）
（５）前記一般式（Ｘ３）における中心金属Ｍ ^x3が、イリジウムである（１）〜（４）のいずれか１項に記載の有機電界発光素子。
（６）一対の電極間に少なくとも一層の発光層を含む有機電界発光素子であって、正孔輸送層と発光層に加え、励起子ブロック層、正孔注入層、正孔ブロック層および電子輸送層からなる群から選ばれる少なくとも一つの層を有することを特徴とする（１）〜（５）のいずれか１項に記載の有機電界発光素子。
本明細書中の鎖状配位子とは、環状配位子（例えばポルフィリン、フタロシアニンなど）でない配位子である。一般式(８)を例にとると、Ｌ^８１、Ｌ^８３がＹ^８１、Ｌ^８２、Ｙ^８２、Ｍ^８１を介さずに連結することがない配位子のことをいう。Ｌ^８１、Ｙ^８１、Ｌ^８２、Ｙ^８２、Ｌ^８３に環構造（例えばベンゼン、ピリジン、キノリンなど）が含まれていても、Ｌ^８１とＬ^８３がＹ^８１、Ｌ^８２、Ｙ^８２、Ｍ^８１を介さずに連結していなければ、その配位子を鎖状配位子と呼ぶ。Ｌ^８１とＹ^８１の間、Ｙ^８１とＬ^８２の間、Ｌ^８２とＹ^８２の間、Ｙ^８２とＬ^８３の間にさらに原子群が存在して環を形成しても良い。
(In the formula, Z ^H6 represents an oxygen atom, a sulfur atom, —C (R ^H63 ) R ^H64 —, or —NR ^H65 —. R ^H63 , R ^H64 and R ^H65 represent a hydrogen atom or a substituent. Q ^H61 Represents an atomic group necessary to form a 5-membered ring or a 6-membered ring, Q ^H62 represents an atomic group necessary to form a heterocycle, M ⁶ represents a metal ion, and n ⁶ represents 1 or more. L ^H represents a ligand, m ⁶ represents an integer of 0 or more, and the bond type between each atom in the formula is any of a single bond, a double bond, a triple bond, and a coordination bond. And (24) an organic electroluminescent device including at least one light emitting layer between a pair of electrodes, in addition to a hole transport layer and a light emitting layer, an exciton block layer, a hole injection layer, a hole (1) to (23) characterized by having at least one layer selected from the group consisting of a block layer and an electron transport layer The organic electroluminescence device according to 1, wherein Zureka.
Specific means for solving the problems of the present invention are shown below.
(1) An organic electroluminescent element having an organic compound layer including at least one light emitting layer between a pair of electrodes, the light emitting layer including at least one light emitting material and at least one host material. The light emitting material is a metal complex compound represented by the following general formula ( X3 ) that emits phosphorescence, and the metal complex that functions as a host material is an organic electric field represented by the following general formula (H-5) Light emitting element.

(In the general formula ^{(X3), .Y X31 ~Y X36} M X3 is representative of the metal ions is a carbon atom, a nitrogen atom, .L ^X31 ~L ^X34 representing the phosphorus atom is a single bond, a double bond or a linking group binding of .M ^X3 and Y ^X31 to Y ^X36 representing may be a covalent bond at each coordinate bond.)

(In the formula, R ^H51 and R ^H52 represent a hydrogen atom or a substituent. Z ^H5 represents an oxygen atom, a sulfur atom, —C (R ^H53 ) R ^H54 —, or —NR ^H55 —. R ^H53 , R ^H54 And R ^H55 represents a hydrogen atom or a substituent, Q ^H5 represents an atomic group necessary to form a 5-membered ring or a 6-membered ring, M ⁵ represents a metal ion, and n ⁵ represents an integer of 1 or more. L ^H represents a ligand, and m ⁵ represents an integer greater than or equal to 0. The bond type between each atom in the formula may be any of a single bond, a double bond, a triple bond, and a coordination bond.
(2) ^Y X31 ^{to Y X36} in the general formula (X3) The organic electroluminescent device according to a carbon atom or a nitrogen atom (1).
(3) The organic electric field according to (1) or (2), wherein Y ^X31 , Y ^X33 and Y ^X35 in the general formula (X3) are nitrogen atoms, and Y ^X32 , Y ^X34 and Y ^X36 are carbon atoms. Light emitting element.
(4) The organic electroluminescent element according to any one of (1) to (3), wherein the metal complex that functions as a host material is represented by the following general formula (H-6).

(In the formula, Z ^H6 represents an oxygen atom, a sulfur atom, —C (R ^H63 ) R ^H64 —, or —NR ^H65 —. R ^H63 , R ^H64 and R ^H65 represent a hydrogen atom or a substituent. Q ^H61 Represents an atomic group necessary to form a 5-membered ring or a 6-membered ring, Q ^H62 represents an atomic group necessary to form a heterocycle, M ⁶ represents a metal ion, and n ⁶ represents 1 or more. L ^H represents a ligand, m ⁶ represents an integer of 0 or more, and the bond type between each atom in the formula is any of a single bond, a double bond, a triple bond, and a coordination bond. Good.)
(5) center metals M ^x3 in formula (X3) is iridium (1) The organic electroluminescent device according to any one of - (4).
(6) An organic electroluminescent device including at least one light emitting layer between a pair of electrodes, in addition to a hole transport layer and a light emitting layer, an exciton block layer, a hole injection layer, a hole block layer, and an electron transport It has at least 1 layer chosen from the group which consists of layers, The organic electroluminescent element of any one of (1)-(5) characterized by the above-mentioned.
The chain ligand in the present specification is a ligand that is not a cyclic ligand (for example, porphyrin, phthalocyanine, etc.). Taking the general formula (8) as an example, it means a ligand in which L ⁸¹ and L ⁸³ are not linked without interposing Y ⁸¹ , L ⁸² , Y ⁸² and M ⁸¹ . Even if L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² , and L ⁸³ contain a ring structure (eg, benzene, pyridine, quinoline, etc.), L ⁸¹ and L ⁸³ are Y ⁸¹ , L ⁸² , Y ⁸² , M ⁸¹ If they are not linked without intervening, the ligand is called a chain ligand. An atomic group may exist between L ⁸¹ and Y ⁸¹ , between Y ⁸¹ and L ⁸² , between L ⁸² and Y ⁸² , and between Y ⁸² and L ⁸³ to form a ring.

  The organic EL device of the present invention exhibits high luminous efficiency and is excellent in durability. The light emitting device of the present invention can be suitably used in the fields of display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like.

-Organic electroluminescence device-
Hereinafter, the organic electroluminescent element of the present invention (hereinafter sometimes referred to as “the element of the present invention” as appropriate) will be described in detail.
The element of the present invention has at least one organic compound layer including an organic light emitting layer between a pair of electrodes (may be a layer made of only an organic compound or an organic layer containing an inorganic compound). An organic electroluminescent device having the following general formula (X3) in which the organic light emitting layer includes at least one light emitting material and at least one host material, and the light emitting material emits phosphorescence. The host material is a metal complex represented by the following general formula (H-5).

(In the general formula (X3), M ^X3 Represents a metal ion. Y ^X31 ~ Y ^X36 Represents a carbon atom, a nitrogen atom, or a phosphorus atom. L ^X31 ~ L ^X34 Represents a single bond, a double bond or a linking group. M ^X3 And Y ^X31 ~ Y ^X36 Each of the bonds may be a coordinate bond or a covalent bond.
In general formula (H-5), R ^H51 , R ^H52 Represents a hydrogen atom or a substituent. Z ^H5 Is an oxygen atom, a sulfur atom, -C (R ^H53 ) R ^H54 -, Or -NR ^H55 -Represents. R ^H53 , R ^H54 And R ^H55 Represents a hydrogen atom or a substituent. Q ^H5 Represents an atomic group necessary to form a 5-membered ring or a 6-membered ring. M ^Five Represents a metal ion. n ^Five Represents an integer of 1 or more. L ^H Represents a ligand, m ^Five Represents an integer of 0 or more. The bond type between each atom in the formula may be a single bond, a double bond, a triple bond, or a coordination bond. )

-Metal complexes that function as luminescent materials-
First, contained in the luminescent layer of the element, a metal complex having a tridentate or higher-dentate ligand containing metal complexes of the present invention (hereinafter, have in metallic complexes E is referred to as a metal complex E which need use the light-emitting layer Will be described in detail.
In the present invention, the light-emitting material contained in the light-emitting layer is a metal complex having a tridentate ligand represented by the general formula (X3).
The metal complex E used in the light emitting layer has a tridentate or higher ligand, but is preferably a chain ligand. The metal complex E used in the light-emitting layer is preferably a metal complex having a chain ligand of 3 to 8 seats, more preferably a metal complex having a chain ligand of 4 to 8 seats. A metal complex having a chain ligand of 6 or less hexadentate is more preferable.

The above-mentioned chain ligand is a nitrogen-containing heterocycle coordinated by nitrogen to the central metal {for example, M ¹¹ in the case of the general formula (1)} (for example, pyridine ring, quinoline ring, pyrrole ring, etc.) It is preferable to have at least one.

The metal complex E used in the light emitting layer preferably emits phosphorescence (more preferably emits phosphor at −30 ° C. or more, more preferably emits phosphor at −10 ° C. or more, more preferably 0 ° C. or more). In the case of using a phosphorescent compound, fluorescence may be emitted simultaneously. However, the phosphorescence intensity at 20 ° C. is 2 as compared with the fluorescence intensity. The compound which is more than twice is preferable, the compound which is more than 10 times is more preferable, and the compound which is more than 100 times is more preferable.

The concentration of the metal complex E used in the luminescent layer, relative to the weight of the light-emitting layer, more preferably preferably from 0.1% to 20 wt%, 0.5 wt% to 10 wt% .

Preferred embodiments other than the present invention of a metal complex having a tetradentate or more ligands in element, said in formula (1). Preferred forms of the general formula (1) are the general formula (2), the following general formula (5), the general formula (9), and the general formula (10).

  A preferred form of the general formula (2) is the following general formula (3).

Preferred forms of the general formula (9) are the following general formulas (6) and (7), and a preferred form of the following general formula (7) is the general formula (11).
A preferred form of the general formula (10) is the general formula (12).

The general formula (1) will be described. M ¹¹ represents a metal ion. Although it does not specifically limit as a metal ion, A bivalent or trivalent metal ion is preferable. As the divalent or trivalent metal ions, platinum ions, iridium ions, rhenium ions, palladium ions, rhodium ions, ruthenium ions, copper ions, europium ions, gadolinium ions, and terbium ions are preferable, and platinum ions, iridium ions, and europium ions. Ions are more preferable, platinum ions and iridium ions are more preferable, and platinum ions are particularly preferable.

L ¹¹ , L ¹² , L ¹³ and L ¹⁴ each represent a ligand coordinated to M ¹¹ . As an atom contained in L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ and coordinated to M ¹¹ , a nitrogen atom, an oxygen atom, a sulfur atom, and a carbon atom are preferable, and a nitrogen atom, an oxygen atom, and a carbon atom are included. More preferred.

The bond formed by M ¹¹ and L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ may be a covalent bond, an ionic bond, or a coordinate bond. The ligand composed of L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , and L ¹⁴ may be an anionic ligand (a ligand in which at least one anion binds to a metal). preferable. 1-3 are preferable, as for the number of anions in an anionic ligand, 1 and 2 are more preferable, and 2 is further more preferable.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a carbon atom are not particularly limited. However, imino ligands and aromatic hydrocarbon ring ligands (for example, benzene ligands and naphthalene coordinations) Children, anthracene ligands, phenanthracene ligands, etc.), heterocyclic ligands (eg thiophene ligands, pyridine ligands, pyrazine ligands, pyrimidine ligands, thiazole ligands, oxazole ligands) A ligand, a pyrrole ligand, an imidazole ligand, a pyrazole ligand, and a condensed ring containing them (for example, a quinoline ligand, a benzothiazole ligand, and the like). .

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by a nitrogen atom are not particularly limited, but nitrogen-containing heterocyclic ligands {eg, pyridine ligand, pyrazine ligand, pyrimidine coordination Ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxadiazole ligand, Thiadiazole ligands, condensed rings containing them (for example, quinoline ligands, benzoxazole ligands, benzimidazole ligands, etc.), and tautomers thereof (in the present invention, normal isomerism) The following examples are also defined as tautomers, for example, 5-membered heterocyclic ligand of compound (24), 5-membered heterocyclic ligand of compound (64), compound (145) 5-membered heterocycle coordination Are also defined as pyrrole tautomers, etc.}, amino ligands {alkylamino ligands (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms). Such as methylamino), arylamino ligands (such as phenylamino), acylamino ligands (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). Particularly preferably having 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino ligand (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, especially Preferably having 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino ligands (preferably Or 7 to 20 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino and the like, and a sulfonylamino ligand (preferably carbon number). 1-30, more preferably 1-20 carbon atoms, particularly preferably 1-12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc.), imino ligands, etc.}. These ligands may be further substituted.

L ¹¹ , L ¹² , L ¹³ , and L ¹⁴ coordinated to M ¹¹ by an oxygen atom are not particularly limited, but are alkoxy ligands (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly Preferably it is C1-C10, for example, methoxy, ethoxy, butoxy, 2-ethylhexyloxy etc.), an aryloxy ligand (preferably C6-C30, more preferably C6-C6). 20, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), heterocyclic oxy ligands (preferably 1 to 30 carbon atoms, more preferably Is a C1-C20, particularly preferably C1-C12, for example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like. An acyloxy ligand (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), silyloxy ligand ( Preferably it has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy, triphenylsilyloxy, etc.), carbonyl ligands (for example ketones) Ligands, ester ligands, amide ligands, etc.), ether ligands (eg, dialkyl ether ligands, diaryl ether ligands, furyl ligands, etc.).

L ¹¹ , L ¹² , L ¹³ and L ¹⁴ coordinated to M ¹¹ by a sulfur atom are not particularly limited, but are alkylthio ligands (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly Preferably it is C1-C12, for example, methylthio, ethylthio etc. are mentioned), an arylthio ligand (preferably C6-C30, more preferably C6-C20, especially preferably C6-C6). 12 such as phenylthio), a heterocyclic thio ligand (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, for example, pyridylthio. , 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), thiocarbonyl ligands (for example, thioketone ligands) Etc. thioester ligand), a thioether ligands (e.g. dialkyl thioether ligands, diaryl thioether ligands, etc. thiofuryl ligand), and the like. These substituted ligands may be further substituted.

L ¹¹ and L ¹⁴ are aromatic hydrocarbon ring ligands, alkyloxy ligands, aryloxy ligands, ether ligands, alkylthio ligands, arylthio ligands, alkylamino ligands, arylamino Ligand, acylamino ligand, nitrogen-containing heterocyclic ligand (eg pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole Ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxadiazole ligands, thiadiazole ligands, and condensed ligand bodies containing them (for example, quinoline) Ligands, benzoxazole ligands, benzimidazole ligands, and the like, and tautomers thereof) are preferred, aromatic carbocyclic ligands, aryloxy ligands , Arylthio ligands, arylamino ligands, and pyridine ligands, pyrazine ligands, imidazole ligands, and condensed ligand bodies containing them (for example, quinoline ligands, quinoxaline ligands) Benzimidazole ligand and the like, and tautomers thereof are more preferable, aromatic carbocyclic ligands, aryloxy ligands, arylthio ligands, arylamino ligands are more preferable, aromatic A group carbocyclic ligand and an aryloxy ligand are particularly preferred.

L ¹² and L ¹³ are preferably ligands that form a coordinate bond with M ¹¹ . Examples of the ligand that forms a coordination bond with M ¹¹ include a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, and a condensed ring containing them (for example, Quinoline ring, benzoxazole ring, benzimidazole ring, indolenine ring, etc.) and tautomers thereof, and pyridine ring, pyrazine ring, pyrimidine ring, pyrrole ring, and condensed ring containing them (for example, Quinoline ring, benzpyrrole, etc.) and tautomers thereof are more preferable, pyridine ring, pyrazine ring, pyrimidine ring, and condensed ring containing them (for example, quinoline ring, etc.) are more preferable, pyridine ring And a condensed ring containing a pyridine ring (such as a quinoline ring) is particularly preferable.

L ¹⁵ represents a ligand coordinated to M ¹¹ . L ¹⁵ is preferably a 1-4-dentate ligand, and more preferably a 1-4-dentate anionic ligand. Although it does not specifically limit as an anionic ligand of 1-4 tetradentate, The monoanionic property 2 containing a halogen ligand, a 1, 3- diketone ligand (for example, acetylacetone ligand etc.), and a pyridine ligand. Formed with a bidentate ligand (eg, picolinic acid ligand, 2- (2-hydroxyphenyl) -pyridine ligand, etc.), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , L ¹⁴ The tetradentate ligand is preferably a 1,3-diketone ligand (such as an acetylacetone ligand), a monoanionic bidentate ligand containing a pyridine ligand (such as a picolinic acid ligand, 2- (2-hydroxyphenyl) -pyridine ligands, etc.), L ¹¹ , Y ¹² , L ¹² , Y ¹¹ , L ¹³ , Y ¹³ , L ¹⁴ and more preferably tetradentate ligands. , 3-diketone ligand (eg acetylacetone ligand), Monoanionic bidentate ligands containing lysine ligands (eg, picolinic acid ligands, 2- (2-hydroxyphenyl) -pyridine ligands, etc.) are more preferred, and 1,3-diketone ligands Particularly preferred are (eg acetylacetone ligands). The number of coordination sites and the number of ligands do not exceed the coordination number of the metal. L ¹⁵ does not combine with 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. The linking group is not particularly limited, but for example, a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, a silicon atom linking group, and Examples thereof include a linking group composed of these combinations. The bonds 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 , and Y ¹³ and L ¹⁴ represent a single bond or a double bond.

Y ¹¹ , Y ¹² and Y ¹³ are each preferably a single bond, a double bond, a carbonyl linking group, an alkylene linking group or an alkenylene group, and Y ¹¹ is more preferably a single bond or an alkylene group, further preferably an alkylene group. Y ¹² and Y ¹³ are more preferably a single bond or an alkenylene group, and even more preferably a single bond.

Ring formed by Y ¹² , L ¹¹ , L ¹² , M ¹¹ , Ring formed by Y ¹¹ , L ¹² , L ¹³ , M ¹¹ , Ring formed by Y ¹³ , L ¹³ , L ¹⁴ , M ¹¹ Are preferably 4 to 10 ring members, more preferably 5 to 7 ring members, and still more preferably 5 or 6 ring members.

n ¹¹ represents the 0-4. When M ¹¹ is a metal having a coordination number of 4, n ¹¹ is 0. When M ¹¹ is a metal having a coordination number of 6, n ¹¹ is preferably 1, 2, and more preferably 1. When M ¹¹ is coordination number 6 and n ¹¹ is 1, L ¹⁵ represents a bidentate ligand, and when M ¹¹ is coordination number 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 1 to 4, more preferably 1 or 2, and more preferably 1. When M ¹¹ is coordination number 8 and n ¹¹ is 1, L ¹⁵ represents a tetradentate ligand, and when n ¹¹ is 2, L ¹⁵ represents a bidentate ligand. When n ¹¹ is plural, the plural L ¹⁵ may be the same or different.

The general formula (2) will be described. M ²¹ has the same meaning as M ¹¹ , and the preferred range is also the same.

Q ²¹ and Q ²² each represent an atomic group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ²¹ ). The nitrogen-containing heterocycle 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 triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, and Examples of the condensed ring include quinoline ring, benzoxazole ring, benzimidazole ring, indolenine ring, and the like and tautomers thereof.

The nitrogen-containing heterocycle formed by Q ²¹ and Q ²² is preferably a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrazole ring, imidazole ring, oxazole ring, pyrrole ring, benzazole ring, and A condensed ring containing them (for example, quinoline ring, benzoxazole ring, benzimidazole ring, etc.) and tautomers thereof, more preferably pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, pyrrole ring, And a condensed ring containing them (for example, quinoline ring and the like) and tautomers thereof, more preferably a pyridine ring and a condensed ring thereof (for example, quinoline ring), A pyridine ring is preferred.

X ²¹ and X ²² are each preferably an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom, more preferably an oxygen atom, a sulfur atom, or a substituted nitrogen atom, still more preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom. preferable.

Y ²¹ has the same meaning as Y ¹¹ , and the preferred range is also the same.

Y ²² and Y ²³ each represent a single bond or a linking group, and preferably a single bond. The linking group is not particularly limited, and includes, for example, a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, and a combination thereof. Examples thereof include a linking group.

  The linking group is preferably a carbonyl linking group, an alkylene linking group, or an alkenylene linking group, more preferably a carbonyl linking group or an alkenylene linking group, and even more preferably a carbonyl linking group.

R ²¹ , R ²² , R ²³ and R ²⁴ each represent a hydrogen atom or a substituent. Although it does not specifically limit as a substituent, For example, it is an alkyl group (preferably C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, methyl, ethyl, iso-propyl. , Tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl. Preferably it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl and the like, and an amino group (preferably). Has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. Examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino. ),

An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), A heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like.) An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably carbon number) -12, for example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms). For example, methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, particularly preferably having 7 to 12 carbon atoms, such as phenyl And oxycarbonyl).

An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), an acylamino group (preferably having a carbon number) 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino and the like, and aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably carbon atoms). 7 to 20, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonylamino ), Sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc. A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, Famoyl etc.),

A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like), alkylthio. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), an arylthio group (preferably having 6 to 6 carbon atoms). 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). -20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolyl E, 2-benzoxazolylthio, 2-benzthiazolylthio, etc.), sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, mesyl, tosyl, etc.), sulfinyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzene And ureido groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include ureido, methylureido, and phenylureido. ),

A phosphoric acid amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide); Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic ring A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom and a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl and thienyl. , Piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl , An azepinyl group, etc.), a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl and triphenylsilyl). ), A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy). Is mentioned. These substituents may be further substituted.

R ²¹ , R ²² , R ²³ , and R ²⁴ are each an alkyl group, an aryl group, R ²¹ and R ^22, or R ²³ and R ²⁴ bonded to form a ring structure (for example, a benzo condensed ring, a pyridine condensed ring, etc.). And a group in which R ²¹ and R ²² or R ²³ and R ²⁴ are combined to form a ring structure (for example, a benzo-fused ring, a pyridine-fused ring, etc.) is more preferred.

L ²⁵ has the same meaning as L ¹⁵ described above, and the preferred range is also the same.
n ²¹ has the same meaning as n ¹¹ , and the preferred range is also the same.

In the general formula (2), when the ring formed by Q ²¹ and Q ²² is a pyridine ring, Y ²¹ is a metal complex representing a linking group, or the ring formed by Q ²¹ and Q ²² is a pyridine ring, ²¹ is a single bond or a double bond, and X ²¹ and X ²² are a sulfur atom, a substituted or unsubstituted nitrogen atom, or a ring formed by Q ²¹ and Q ²² is a nitrogen-containing hetero 5-membered A metal complex representing a ring or a nitrogen-containing 6-membered ring containing two or more nitrogen atoms is preferable.

The general formula (3) will be described. M ³¹ has the same meaning as M ¹¹ , and the preferred range is also the same.

Z ³¹ , Z ³² , Z ³³ , Z ³⁴ , Z ³⁵ and Z ³⁶ each represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom is more preferred. Examples of the substituent on the carbon include the groups described above for R ²¹ , 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 condensed ring (for example, benzo condensed ring, pyridine condensed ring, etc.). Z ³¹ and T ³¹ , Z ³⁶ and T ³⁸ are bonded via a linking group, and A ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) may be formed.

  As the substituent on the carbon, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) or a halogen atom is preferable. A group that forms a group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, a group that forms an aryl group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, A group that forms a benzo-fused ring, a pyridine-fused ring, etc.) is particularly preferred.

T ³¹ , T ³² , T ³³ , T ³⁴ , T ³⁵ , T ³⁶ , T ³⁷ , and T ³⁸ represent a substituted or unsubstituted carbon atom and a nitrogen atom, respectively, and a substituted or unsubstituted carbon atom is more preferable. Examples of the substituent on the carbon include the groups described for R ²¹ , 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 condensed ring (for example, a benzo-condensed ring).

The substituent on the carbon is preferably an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group that forms a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.), or a halogen atom. A group that forms (for example, a benzo-fused ring, a pyridine-fused ring, etc.) and a halogen atom are more preferred, an aryl group and a halogen atom are more preferred, and an aryl group is particularly preferred.
X ³¹ and X ³² have the same meanings as X ²¹ and X ²² , respectively, and preferred ranges are also the same.

The general formula (5) will be described. M ⁵¹ has the same meaning as M ¹¹ , and the preferred range is also the same.

Q ⁵¹ and Q ⁵² are synonymous with Q ²¹ and Q ²² , respectively, and preferred ranges are also the same.
Q ⁵³ and Q ⁵⁴ each represent a group forming a nitrogen-containing heterocycle (a ring containing a nitrogen coordinated to M ⁵¹ ). The nitrogen-containing heterocycle formed by Q ⁵³ and Q ⁵⁴ is not particularly limited, but a tautomer of a pyrrole derivative, a tautomer of an imidazole derivative (for example, a hetero 5-membered ring ligand of compound (29), etc.) ), A tautomer of a thiazole derivative (such as a hetero 5-membered ring ligand of the compound (30)), a tautomer of a oxazole derivative (such as a hetero 5-membered ring ligand of the compound (31)), and the like. Preferably, tautomers of pyrrole derivatives, tautomers of imidazole derivatives, tautomers of thiazole derivatives are more preferable, tautomers of pyrrole derivatives, tautomers of imidazole derivatives are more preferable, pyrrole derivatives The tautomers are particularly preferred.

Y ⁵¹ has the same meaning as Y ¹¹ , and the preferred range is also the same.
L ⁵⁵ has the same meaning as the L ^15, and the preferred range is also the same.
n ⁵¹ has the same meaning as n ¹¹ , and the preferred range is also the same.

W ⁵¹ and W ⁵² each represent a substituted or unsubstituted carbon atom or a nitrogen atom, preferably an unsubstituted carbon atom or a nitrogen atom, and more preferably an unsubstituted carbon atom.

The general formula (9) will be described. M ^A1 , Q ^A1 , Q ^A2 , Y ^A1 , Y ^A2 , Y ^A3 , R ^A1 , R ^A2 , R ^A3 , R ^A4 , L ^A5 , n ^A1 are M ²¹ , Q ²¹ , Q in the general formula (2). ²² , Y ²¹ , Y ²² , Y ²³ , R ²¹ , R ²² , R ²³ , R ²⁴ , L ²⁵ , n ²¹ , and the preferred range is also the same.

The general formula (6) will be described. M ⁶¹ has the same meaning as M ¹¹ , and the preferred range is also the same.

Q ⁶¹ and Q ⁶² each 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 a condensed ring thereof. A ring.

The ring formed by Q ⁶¹ and Q ⁶² is preferably a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring, or a condensed ring thereof, and more preferably a benzene ring, a pyridine ring, or a condensed ring thereof. More preferred are benzene rings and condensed rings thereof.

Y ⁶¹ has the same meaning as Y ¹¹ , and the preferred range is also the same.
Y ⁶² and Y ⁶³ each represent a linking group or a single bond. The linking group is not particularly limited, and includes, for example, a carbonyl linking group, a thiocarbonyl linking group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom linking group, a nitrogen atom linking group, and combinations thereof. Examples thereof include a linking group.

Y ⁶² and Y ⁶³ are each preferably a single bond, a carbonyl linking group, an alkylene linking group or an alkenylene group, more preferably a single bond or an alkenylene group, and even more preferably a single bond.

L ⁶⁵ has the same meaning as L ¹⁵ described above, and the preferred range is also the same.
n ⁶¹ has the same meaning as n ¹¹ , and the preferred range is also the same.

Z ⁶¹ , Z ⁶² , Z ⁶³ , Z ⁶⁴ , Z ⁶⁵ , Z ⁶⁶ , Z ⁶⁷ and Z ⁶⁸ each represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom is preferred. Examples of the substituent on the carbon include the groups described above for R ²¹ , 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 condensed ring (for example, a benzo condensed ring, a pyridine condensed 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.

  As the substituent on the carbon, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (for example, a benzo condensed ring, a pyridine condensed ring, etc.) or a halogen atom is preferable. A group that forms a group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, a group that forms an aryl group or a condensed ring (for example, a benzo-condensed ring, a pyridine-condensed ring, etc.) is more preferable, A group that forms a benzo-fused ring, a pyridine-fused ring, etc.) is particularly preferred.

The general formula (7) will be described. M ⁷¹ has the same meaning as the M ^11, and the preferred range is also the same.

Y ⁷¹ , Y ⁷² , and Y ⁷³ have the same meanings as Y ⁶² , and preferred ranges are also the same.
L ⁷⁵ has the same meaning as L ¹⁵ described above, and the preferred range is also the same.
n ⁷¹ has the same meaning as the n ^11, and the preferred range is also the same.

Z ⁷¹ , Z ⁷² , Z ⁷³ , Z ⁷⁴ , Z ⁷⁵ and Z ⁷⁶ each represent a substituted or unsubstituted carbon atom or a nitrogen atom, and a substituted or unsubstituted carbon atom is preferred. Examples of the substituent on carbon include the groups described for R ²¹ . Z ⁷¹ and Z ⁷² , Z ⁷³ and Z 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 are synonymous with the substituents of R ^{21 to} R ^{24 in} the general formula (2), and the preferred range is also the same.

The general formula (11) will be described.
R ^C1 and R ^C2 each represent a hydrogen atom or a substituent, and the substituent represents the alkyl group or aryl group described as the substituent for R ²¹ to R ^{24 in} the general formula (2). The substituents represented by R ^C3 , R ^C4 , R ^C5 and R ^C6 are also synonymous with the substituents of R ²¹ to R ^{24 in} the general formula (2). n ^C3 and n ^C6 each represents an integer of 0 to 3, n ^C4 and n ^C5 each represent an integer of 0 to 4, and when each of R ^C3 , R ^C4 , R ^C5 and R ^C6 has a plurality of R ^C3 , 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 and a halogen atom.

Next, the general formula (10) will be described.
M ^B1 , Y ^B2 , Y ^B3 , R ^B1 , R ^B2 , R ^B3 , R ^B4 , L ^B5 , n ^B3 , X ^B1 , X ^B2 are M ²¹ , Y ²² , Y ²³ , R in the general formula (2). ²¹ , R ²² , R ²³ , R ²⁴ , L ²⁵ , n ²¹ , X ²¹ , X ²² are synonymous and preferred ranges are also the same. Y ^B1 represents a linking group and is the same as Y ^{21 in the} general formula (2), preferably a vinyl group substituted at the 1,2-position, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring or a carbon number of 2 8 represents a methylene group. R ^B5 and R ^B6 represent a hydrogen atom or a substituent, and the substituent represents the alkyl group, aryl group, or heterocyclic group described as the substituent of R ²¹ to R ^{24 in} the general formula (2). However, Y ^B1 is not linked to R ^B5 or R ^B6 . n ^B1 and n ^B2 each represents an integer of 0 to 1.

Next, the general formula (12) will be described.
The substituents represented by R ^D1 , R ^D2 , R ^D3 , and R ^D4 are the same as the substituents represented by R ^B5 and R ^{B6 in} the general formula (10), and the preferred ranges are also the same. n ^D1 and n ^D2 represent an integer of 0 to 4.
Y ^D1 represents a vinyl group, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, or a methylene group having 1 to 8 carbon atoms substituted at the 1 and 2 positions.

  A preferred form of the metal complex having a tridentate ligand used in the present invention is the general formula (8).

The general formula (8) will be described. M ⁸¹ has the same meaning as M ¹¹ , and the preferred range is also the same.

L ⁸¹ , L ⁸² , and L ⁸³ are synonymous with L ¹¹ , L ¹² , and L ¹⁴ , respectively, and preferred ranges are also the same.
Y ⁸¹ and Y ⁸² have the same meanings as Y ¹¹ and Y ¹² , respectively, and preferred ranges are also the same.

L ⁸⁵ represents a ligand coordinated to M ⁸¹ . L ⁸⁵ is preferably a 1 to 3 ligand, more preferably a 1 to 3 anionic ligand. No particular limitation is imposed on the anionic ligand 1-3 seat, tridentate ligand formed by halogen ^{ligand, L 81, Y 81, L} 82, Y 82, L 83 is preferably, L ⁸¹ , Y ⁸¹ , L ⁸² , Y ⁸² and L ⁸³ are more preferable. Never L ⁸⁵ is connected to the L ^81, L ⁸³ without passing through the metal. The number of coordination sites and the number of ligands do not exceed the coordination number of the metal.

n ⁸¹ represents 0 to 5. When M ⁸¹ is a metal having a coordination number of 4, n ⁸¹ is 1 and L ⁸⁵ represents a monodentate ligand. When M ⁸¹ is a metal having a coordination number of 6, n ⁸¹ is preferably 1 to 3, more preferably 1, 3 and even more preferably 1. When M ⁸¹ is coordination number 6 and n ⁸¹ is 1, L ⁸⁵ represents a tridentate ligand, and when M ⁸¹ is coordination number 6 and n ⁸¹ is 2, L ⁸⁵ is one monodentate ligand and bidentate. ligand one of the stands, when L ⁸⁵ of n ⁸¹ in M ⁸¹ is coordination number of 6 3 represents a monodentate ligand. When M ⁸¹ is a metal having a coordination number of 8, n ⁸¹ is preferably 1 to 5, more preferably 1 or 2, and more preferably 1. When M ⁸¹ is coordination number 8 and n ⁸¹ is 1, L ⁸⁵ represents a pentadentate ligand, and when n ⁸¹ is 2, L ⁸⁵ represents one tridentate ligand and one bidentate ligand. , N ⁸¹ is 3, L ⁸⁵ represents one tridentate ligand and two monodentate ligands, or two bidentate ligands and one monodentate ligand, and when n ⁸¹ is 4, L ⁸⁵ Represents one bidentate ligand and three monodentate ligands, and when n ⁸¹ is 5, L ⁸⁵ represents five monodentate ligands. When ⁿ⁸¹ is plural, the plural ^L85s may be the same or different.

A preferable form of the general formula (8) is an aromatic carbocyclic or heterocyclic ring in which L ⁸¹ , L ⁸² and L ^{83 in the} general formula (8) are carbon atoms and coordinate to M ⁸¹ , or a nitrogen atom and M ⁸¹ Represents a nitrogen-containing heterocycle that is coordinated to each other, and at least one of L ⁸¹ , L ⁸² , and L ⁸³ is a nitrogen-containing heterocycle. Aromatic carbocycles, heterocycles and nitrogen-containing heterocycles coordinated by nitrogen atoms coordinate with these carbon atoms are ligands and nitrogen atoms coordinated with carbon atoms to M ¹¹ described in the general formula (1). Examples of coordination are given, and the preferred range is also the same. Y ⁸¹ and Y ⁸² preferably represent a single bond or a methylene group.
Other preferable forms of the general formula (8) are the following general formula (13) and the following general formula (14).

The general formula (13) will be described. M ⁹¹ has the same meaning as M ⁸¹ , and the preferred range is also the same.

Q ⁹¹ and Q ⁹² represent a group that forms a nitrogen-containing heterocycle (a ring containing nitrogen coordinated to M ⁹¹ ). The nitrogen-containing heterocycle formed by Q ⁹¹ and Q ⁹² is not particularly limited. For example, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, thiazole ring, oxazole ring, pyrrole ring, pyrazole ring, imidazole Examples thereof include a ring, a triazole ring, and a condensed ring containing them (for example, a quinoline ring, a benzoxazole ring, a benzimidazole ring, an indolenine ring, and the like) and tautomers thereof.

The nitrogen-containing heterocycle formed by Q ⁹¹ and Q ⁹² is preferably a pyridine ring, a pyrazole ring, a thiazole ring, an imidazole ring, a pyrrole ring, and a condensed ring containing them (for example, a quinoline ring, a benzthiazole ring, Benzimidazole ring, indolenine ring, etc.) and tautomers thereof, more preferably pyridine ring, pyrrole ring, and condensed ring containing them (for example, quinoline ring, etc.), and these A tautomer, more preferably a pyridine ring, and a condensed ring containing them (for example, a quinoline ring), particularly preferably a pyridine ring.

Q ⁹³ represents a group forming a (ring containing coordinating nitrogen M ⁹¹⁾ nitrogen-containing heterocyclic ring. No particular limitation is imposed on the nitrogen-containing heterocyclic ring formed by Q ^93, a pyrrole ring, an imidazole ring, tautomers of the triazole ring, and a condensed ring body thereof (for example, benzopyrrole, etc.) are preferred, a pyrrole ring And tautomers of condensed rings containing a pyrrole ring (for example, benzpyrrole) are more preferable.

W ⁹¹ and W ⁹² are synonymous with W ⁵¹ and W ⁵² , respectively, and preferred ranges are also the same.
L ⁹⁵ has the same meaning as the L ^85, and the preferred range is also the same.
n ⁹¹ has the same meaning as the n ^81, and the preferred range is also the same.

The general formula (14) will be described. M ¹⁰¹ has the same meaning as M ⁸¹ , and the preferred range is also the same.
Q ¹⁰² has the same meaning as the Q ^21, and the preferred range is also the same.
Q ¹⁰¹ has the same meaning as Q ⁹¹ , and the preferred range is also the same.
Q ¹⁰³ represents a group that forms an aromatic ring. The aromatic ring formed by Q ¹⁰³ is not particularly limited, but a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, and a condensed ring containing them (for example, a naphthalene ring) are preferable. The condensed ring containing (for example, naphthalene ring etc.) is more preferable, and a benzene ring is particularly preferable.

Y ¹⁰¹ and Y ¹⁰² each have the same meaning as Y ²² described above, and the preferred range is also the same.
L ¹⁰⁵ has the same meaning as the L ^85, and their preferable ranges are also the same.
n ¹⁰¹ has the same meaning as the n ^81, and the preferred range is also the same.
X ¹⁰¹ has the same meaning as X ²¹ , and the preferred range is also the same.

The metal complex E used in the light emitting layer may be a low molecular compound, and is an oligomer compound or polymer compound (weight average molecular weight (polystyrene conversion) is preferably 1000 to 5000000, more preferably 2000 to 1000000, still more preferably. 3,000 to 100,000). In the case of a polymer compound, the structure represented by the general formula (1) may be included in the polymer main chain, or may be included in the polymer side chain. In the case of a polymer compound, it may be a homopolymer compound or a copolymer. The compound used for the light emitting layer is preferably a low molecular compound.

Another embodiment of the metal complex having a tridentate ligand used in the light emitting layer is a metal complex represented by the general formula (X1). Of the metal complex represented by the general formula (X1), preferably a metal complex represented by the general formula (X2), Ri metal complexes der more preferably represented by the general formula (X3) In the present invention, a metal complex represented by the general formula (X3) is used .

The general formula (X1) will be described.
M ^X1 represents a metal ion. The metal ion is not particularly limited, but a monovalent to trivalent metal ion is preferable, a divalent or trivalent metal ion is more preferable, and a trivalent metal ion is more preferable. Specifically, platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, copper ion, europium ion, gadolinium ion, terbium ion are preferable, platinum ion, iridium ion, europium ion are more preferable, platinum ion Further, iridium ions are more preferable, and iridium ions are particularly preferable.
Q ^X11 to Q ^X16 represents an atomic group containing an atom coordinating to an atom or M ^X1 coordinating to M ^X1. When Q ^{X11 to} Q ^X16 represent an atom coordinated to M ^X1 , specific atoms include a carbon atom, a nitrogen atom, an oxygen atom, a silicon atom, a phosphorus atom, a sulfur atom, and preferably nitrogen. An atom, an oxygen atom, a sulfur atom, and a phosphorus atom, more preferably a nitrogen atom and an oxygen atom.
When Q ^{X11 to} Q ^X16 represent an atomic group including an atom coordinated to M ^X1 , examples of those coordinated by a carbon atom include an imino group, an aromatic hydrocarbon ring group (benzene, naphthalene, etc.), hetero Examples thereof include ring groups (thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole and the like) and condensed rings containing them, and tautomers thereof.

  Examples of those coordinated by a nitrogen atom include nitrogen-containing heterocyclic groups (pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, imidazole, pyrazole, triazole, etc.), amino groups (preferably alkylamino groups (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, such as methylamino), arylamino groups (eg phenylamino), etc.), acylamino groups (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2 carbon atoms). To 30, more preferably 2 to 20 carbon atoms, particularly preferably A prime number of 2 to 12, for example, methoxycarbonylamino, etc.), an aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, and particularly preferably having 7 to 12 carbon atoms). Yes, for example, phenyloxycarbonylamino, etc.), a sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino) , Benzenesulfonylamino, etc.), and imino groups. These groups may be further substituted.

  As the one coordinated by an oxygen atom, an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2- Ethylhexyloxy, etc.), aryloxy groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy , 2-naphthyloxy, etc.), heterocyclic oxy groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, etc. , Pyrimidyloxy, quinolyloxy, etc.), acyloxy groups (preferably having 2 to 30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, such as acetoxy and benzoyloxy), silyloxy groups (preferably 3-40 carbon atoms, more preferably 3-30 carbon atoms, especially Preferably, it has 3 to 24 carbon atoms, and examples include trimethylsilyloxy, triphenylsilyloxy, etc.), carbonyl group (for example, ketone group, ester group, amide group, etc.), ether group (for example, dialkyl ether group, diaryl ether). Group, furyl group, etc.).

  The thing coordinated with a sulfur atom is an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like. ), An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio), a heterocyclic thio group (preferably carbon 1-30, more preferably 1-20 carbon atoms, particularly preferably 1-12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like. ), Thiocarbonyl groups (for example, thioketone groups, thioester groups, etc.), thioether groups (for example, dialkylthioethers). Group, diaryl thioether, etc. thiofuryl group).

  Examples of those coordinated by a phosphorus atom include a dialkylphosphino group, a diarylphosphino group, a trialkylphosphine, a triarylphosphine, and a phosphinin group. These groups may be further substituted.

As an atomic group represented by Q ^{X11 to} Q ^X16 , an aromatic hydrocarbon ring group coordinated with carbon, an aromatic heterocyclic group coordinated with carbon, and a nitrogen-containing aromatic heterocyclic group coordinated with nitrogen An alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, a dialkylphosphino group, more preferably an aromatic hydrocarbon ring group coordinated with carbon, an aromatic heterocyclic group coordinated with carbon, and nitrogen. It is a nitrogen-containing aromatic heterocyclic group to be coordinated.

L ^{X11 to} L ^X14 represent a single bond, a double bond or a linking group. Although it does not specifically limit as a coupling group, The coupling group which consists of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom is preferable, Although a specific example is shown below, it is not limited to these.

These linking groups may be further substituted, and as the substituent, those exemplified as the substituents represented by R ^{21 to} R ²⁴ in the general formula (2) can be applied, and the preferred ranges are also the same. L ^{X11 to} L ^X14 are preferably a single bond, a dimethylmethylene group, or a dimethylsilylene group.

The metal complex represented by the general formula (X1) is more preferably a metal complex represented by the general formula (X2). Next, the general formula (X2) will be described.
M ^X2 has the same meaning as M ^X1 in formula (X1), and the preferred range is also the same. Y ^X21 to Y ^X26 represent an atom coordinating to M ^X2. The bond between Y ^{X21 to} Y ^X26 and M ^X2 may be a coordinate bond or a covalent bond. Y ^{X21 to} Y ^X26 include a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom, preferably a carbon atom and a nitrogen atom. Q ^X21 to Q ^X26 represents an atomic group forming an aromatic hydrocarbon ring or aromatic heterocyclic ring each include Y ^X21 to Y ^X26. The aromatic hydrocarbon ring and aromatic heterocycle formed in this case are benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrole ring, pyrazole ring, imidazole ring, triazole ring, oxazole ring. , Thiazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring, preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyrazole ring, imidazole ring, triazole ring, more preferably benzene. A ring, a pyridine ring, a pyrazine ring, a pyrazole ring and a triazole ring, and particularly preferably a benzene ring and a pyridine ring. These may further have a condensed ring or a substituent.

L ^{X21 to} L ^X24 are synonymous with L ^{X11 to} L ^X14 in the general formula (X1), and preferred ranges thereof are also the same.

The metal complex represented by the general formula (X1) is more preferably a metal complex represented by the general formula (X3). Next, the general formula (X3) will be described.
M ^X3 has the same meaning as M ^X1 in formula (X1), and the preferred range is also the same. Y ^{X31 to} Y ^X36 each represent an atom coordinated to M ^X3 . The bond between Y ^{X31 to} Y ^X36 and M ^X3 may be a coordinate bond or a covalent bond. Y ^{X31 to} Y ^X36 include a carbon atom, a nitrogen atom and a phosphorus atom, and preferably a carbon atom and a nitrogen atom. L ^{X31 to} L ^X34 are synonymous with L ^{X11 to} L ^X14 in the general formula (X1), and preferred ranges thereof are also the same.

Next, although the compound example of the compound used for a light emitting layer is shown with the metal complex of this invention, this invention is not limited to the compound example of this invention illustrated below .
Here, the compounds (1) to (101), (103), (105) to (107), (113) to (131), (135) to (140), (143) to (154), (156) ) To (161), (164) to (166), (168), (169), (171) to (173), and (175) to (242) are reference examples.

(Synthesis method of metal complex E used for light emitting layer )
The metal complex E (compound represented by the general formulas (1) to (14) and the general formulas (X1) to (X3)) used in the light emitting layer can be synthesized by various methods.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

The reaction time for synthesizing the metal complex E used in the light emitting layer varies depending on the activity of the reaction raw material and is not particularly limited, but is preferably 1 minute or more and 5 days or less, more preferably 5 minutes or more and 3 days or less, and more preferably 10 minutes or more. One day or less is more preferable.

The reaction temperature for synthesizing the metal complex E used in the light-emitting layer varies depending on the activity of the reaction, and is not particularly limited. Further preferred.

The metal complex E used for the light emitting layer is selected from the above-described general formulas (1) to (14) and the general formula (X1) to The compound represented by (X3) can be synthesized. For example, when synthesizing the compound represented by the general formula (3), a 6,6′-bis (2-hydroxyphenyl) -2,2′-bipyridyl ligand or a derivative thereof (for example, 2,9-bis (2-hydroxyphenyl) -1,10-phenanthroline ligand, 2,9-bis (2-hydroxyphenyl) -4,7-diphenyl-1,10-phenanthroline ligand, 6,6′-bis ( 2-hydroxy-5-tert-butylphenyl) -2,2′-bipyridyl ligand and the like are preferably 0.1 equivalents to 10 equivalents, more preferably 0.3 equivalents to 6 equivalents with respect to the metal compound. It can be synthesized by adding an equivalent amount, more preferably 0.5 equivalent to 4 equivalents. In the method for synthesizing the compound represented by the general formula (3), each of the reaction solvent, the reaction time, and the reaction temperature is the same as that described in the method for synthesizing the metal complex used in the light emitting layer .

  Derivatives of 6,6'-bis (2-hydroxyphenyl) -2,2'-bipyridyl ligand can be synthesized using various known methods. For example, a 2,2′-bipyridyl derivative (such as 1,10-phenanthroline) and an anisole derivative (such as 4-fluoroanisole) are reacted by the method described in Journal of Organic Chemistry, 741, 11, (1946). Can be synthesized. In addition, halogenated 2,2′-bipyridyl derivatives (eg, 2,9-dibromo-1,10-phenanthroline) and 2-methoxyphenylboronic acid derivatives (eg, 2-methoxy-5-fluorophenylboron) After the Suzuki coupling reaction using an acid or the like as a starting material, the methyl group is deprotected (the method described in Journal of Organic Chemistry, 741, 11, (1946), the method of heating in pyridine hydrochloride, etc. Can be synthesized. In addition, 2,2′-bipyridylboronic acid derivatives (eg, 6,6′-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolyl) -2,2′-bipyridyl) and halogens After the Suzuki coupling reaction using a modified anisole derivative (such as 2-bromoanisole) as a starting material, the methyl group is deprotected (the method described in Journal of Organic Chemistry, 741, 11, (1946), Alternatively, it can also be synthesized by using a method such as heating in pyridine hydrochloride.

-Metal complexes that function as host materials-
A metal complex that functions as a host material (hereinafter sometimes referred to as a metal complex H used in the present invention) functions as a host material. Among the materials contained in the light-emitting layer, a phosphorescent material (phosphorescent material) is used. Materials), and the following various functions (the above-mentioned various functions):
A function of dispersing and holding the light emitting material (phosphorescent material in the present invention) in the layer;
The function of receiving holes from the anode and hole transport layer,
The ability to receive electrons from the cathode, electron transport layer, etc.
The function of transporting holes and / or electrons,
The ability to provide a field for recombination of holes and electrons,
At least one of a function of transferring the energy of excitons generated by recombination to the light emitting material and a function of transporting holes and / or electrons to the light emitting material;
Means a material having

  Among the various functions described above, the material is preferably a material having at least one function of transporting holes and / or electrons and transferring exciton energy generated by recombination to the light emitting material. More preferably, the material has one function. Furthermore, the metal complex used in the present invention may have various functions other than the function of transporting holes and / or electrons and the function of transferring the energy of excitons generated by recombination to the light emitting material.

  The metal complex H used in the present invention is preferably a main component in the light emitting layer in order to function as a host material. The content of the metal complex of the present invention in the light emitting layer is preferably 50% to 99.9% by mass, more preferably 60% to 99% by mass. However, when a plurality of types of the metal complex H of the present invention are contained in the light emitting layer, the above content is preferable as the total amount of the metal complex H of the present invention.

In the present invention, the metal complex H used as a host material is preferably highly stable against electrochemical oxidation and reduction because it can be electrochemically oxidized or reduced when performing the above functions. In other words, those in which oxidizing species (for example, radical cation species) and reducing species (for example, radical anion species) are very stable are preferable.
In addition, when recombination is performed with the metal complex H used in the present invention, first, excitons of the host material are generated. Therefore, the excited state of the metal complex H used in the present invention is decomposed or thermally deactivated. It is preferably stable without causing. This also means that the metal complex H used in the present invention which is stable to light is preferable.

  In the organic EL element, the metal complex H used in the present invention is not decomposed by heat and maintains a stable amorphous film up to a high temperature because the film breakage and the material decomposition due to heat generation during driving are the major factors of deterioration. It is preferable that the material be made.

  In consideration of durability of the light emitting device, the glass transition temperature (Tg) of the metal complex H used in the present invention is preferably 130 ° C. or higher and 400 ° C. or lower, more preferably 135 ° C. or higher and 400 ° C. or lower. Further, it is preferably 140 ° C. or higher and 400 ° C. or lower, particularly preferably 150 ° C. or higher and 400 ° C. or lower, and most preferably 160 ° C. or higher and 400 ° C. or lower. Tg can be confirmed by thermal measurement such as differential scanning calorimetry (DSC) and differential thermal analysis (DTA), X-ray diffraction (XRD), and polarization microscope observation.

  Although the metal species of the metal complex H used for this invention is not specifically limited, The metal of the 2nd-4th period is preferable, More preferably, Li, Be, Na, Mg, Al, K, Ca, Sc, Ti, V , Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Ge, more preferably Li, Be, Na, Mg, Al, Ti, Fe, Co, Ni, Cu, Zn, Ga. Further, Be, Mg, Al, Fe, Ni, Cu, and Zn are more preferable, Be, Mg, Al, Cu, and Zn are more preferable, and Al and Zn are particularly preferable.

  The metal complex H used in the present invention may be a so-called binuclear complex having a plurality of metal ions in the same molecule. Moreover, the binuclear complex which consists of multiple types of metals may be sufficient. Moreover, you may have multiple types of ligand. The metal complex used in the present invention is preferably a neutral metal complex.

Metal complexes H used in the present invention is a metal complex represented by is preferably a chelate complex having a bidentate or more ligands, before following general formula (H- 5).
First, the metal complex represented by the general formula (H-1) will be described.
In General Formula (H-1), X ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, and may have a substituent if possible, or may have another ring structure It may be an atom. Y ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, and may have a substituent if possible, or may be a constituent atom of another ring. M ¹ represents a metal ion. n ¹ represents an integer of 1 or more. L ^H represents a ligand, and m ¹ represents an integer of 0 or more. Q ^H1 represents an atomic group that forms a chelate ring together with X ^H1 , Y ^H1 , and M ¹ . The bond type between each atom in the formula may be a single bond, a double bond, a triple bond, or a coordination bond. However, the bond between Q ^{H1 and} X ^H1 and the bond between Q ^{H1 and} Y ^H1 are not coordination bonds.

The metal complex represented by the general formula (H-1) will be described in detail. X ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, and may have a substituent if possible, or may be a constituent atom of another ring. X ^H1 is preferably an oxygen atom, a nitrogen atom or a sulfur atom, more preferably a nitrogen atom. When X ^H1 is substituted with a substituent, examples of the substituent include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms such as methyl, And ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably carbon. 2 to 12, particularly preferably 2 to 8 carbon atoms such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 20 carbon atoms, more preferably carbon 2 to 12, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl), an aryl group (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, and the like, and a substituted carbonyl group (preferably C1-C20, More preferably, it is C1-C16, Most preferably, it is C1-C12, for example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, etc. are mentioned. ), Substituted sulfonyl groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), heterocyclic groups ( An aliphatic heterocyclic group or an aromatic heterocyclic group, preferably an oxygen atom, a sulfur atom or a nitrogen atom; Preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl groups and the like. And the like. These substituents may be further substituted.

When X ^H1 is a constituent atom of another ring, the other ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrole ring, a thiophene ring, a furan ring, and an oxazole ring. , An isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a tetrazole ring, and a ring in which the aromatic ring is all or partly reduced. These rings may be further condensed with other rings, or may have a substituent. As the substituent, those ^{exemplified as} the substituent for X ^H1 can be applied.

Y ^H1 represents an oxygen atom, a nitrogen atom, a sulfur atom, a carbon atom, or a phosphorus atom, and if possible, may have a substituent or may be a constituent atom of another ring. Y ^H1 is preferably an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, more preferably an oxygen atom or a nitrogen atom, and still more preferably an oxygen atom. When a substituent is substituted on Y ^H1 , those ^{exemplified as} the substituent of X ^H1 can be applied as the substituent.

Q ^H1 represents an atomic group necessary for forming a ring together with X ^H1 , M ¹ and Y ^H1 . The ring composed of Q ^H1 , X ^H1 , M ¹ and Y ^H1 is preferably a 5-membered ring or a 6-membered ring. Q ^H1 may have a substituent, and examples of the substituent include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms). For example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 20 carbon atoms, More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl. (Preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, etc.), substituted carbonyl groups (preferably Has 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and the like. Amino group (preferably having 0 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as dimethylamino, methylcarbonylamino, ethylsulfonylamino, dimethylaminocarbonyl Amino group, phthalimide group, etc.), sulfoni Group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfo group, carboxyl group, heterocyclic group (There are an aliphatic heterocyclic group and an aromatic heterocyclic group. Preferably, it contains any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, especially Preferably it is C2-C12, for example, imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, a triazolyl group etc.), a hydroxy group, an alkoxy group (preferably C1-C20, more) Preferably it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include a methoxy group and a benzyloxy group. Xyl group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include a phenoxy group and a naphthyloxy group. ), Halogen atoms (preferably fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), thiol groups, alkylthio groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 1 carbon atoms). 12 such as a methylthio group, and an arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as a phenylthio group). ), Cyano group, silyl group (preferably having 0 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 18 carbon atoms, such as trimethylsilyl group, triphenylsilyl group, t-butyldiphenyl And a silyl group). These substituents may be further substituted.

M ¹ represents a metal ion. The metal ion is not particularly limited, but is preferably a metal ion included in the second to sixth periods of the periodic table (long period type), more preferably a divalent or trivalent metal ion, More preferably, Be ²⁺ , Mg ²⁺ , Al ³⁺ , Cu ²⁺ , Zn ²⁺ , Ga ³⁺ , Pd ²⁺ , In ³⁺ , Ir ³⁺ , Pt ²⁺ , and more preferably Al ³⁺ , Zn ²⁺ and Ga ³⁺ .

L ^H represents a monodentate or polydentate ligand. Examples of the ligand include a halogen ion (for example, Cl ⁻ , Br ⁻ , I ^{− and the} like), a perchlorate ion, and an alkoxy ion (preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 5, for example, methoxy ion, ethoxy ion, isopropoxy ion, acetylacetonate ion and the like, aryloxy ion (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atom, for example, phenoxy Ions, quinolinol ions, 2- (2-hydroxyphenyl) benzoazole ions, etc.), nitrogen-containing heterocycles (preferably having 1 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, more preferably 3 to 8 carbon atoms). Phenanthrene, bipyridyl, etc.), acyloxy ions (preferably A prime number of 1 to 20, more preferably 2 to 10, more preferably 3 to 8, including acetoxy ion and the like, a silyloxy ion (preferably having a carbon number of 3 to 50, more preferably 3 to 40, still more preferably Is 3 to 25, and examples thereof include triphenylsilyloxy ions), ether compounds (preferably having 2 to 20, carbon atoms, particularly preferably 3 to 10, more preferably 3 to 8, and tetrahydrofuran and the like. ), Hydroxy ions and the like. More preferred are alkoxy ions, silyloxy ions, and aryloxy ions, still more preferred are silyloxy ions and aryloxy ions, and particularly preferred are aryloxy ions.

n ¹ represents an integer of 1 or more, and m ¹ represents an integer of 0 or more. The preferred range of n ¹ and m ¹ varies depending on the metal ion and is not particularly limited, but n ¹ is preferably ¹ to 4, more preferably 1 to 3, and particularly preferably 2 or 3. m ¹ is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. The combination of the numbers of n ¹ and m ¹ is preferably a combination of numbers in which the metal complex represented by the general formula (H-1) becomes a neutral complex.

  In the general formula (H-1), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bond is a single bond. The species is not limited.

  The metal complex represented by the general formula (H-1) is more preferably a metal complex represented by the general formula (H-2) or the general formula (H-3).

In General Formula (H-2), X ^H2 represents an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, and if possible, may have a substituent. The above-mentioned substituents for X ^{H1 in} the above can be applied. X ^H2 is preferably a nitrogen atom. Y ^H2 represents an oxygen atom, a nitrogen atom, or a sulfur atom, and if possible, may have a substituent. ^Examples of the substituent include those listed as the substituent for X ^H1 in formula (H-1). Applicable. Y ^H2 is preferably an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom, more preferably an oxygen atom or a substituted nitrogen atom, and still more preferably an oxygen atom. Z ^H21 , Z ^H22 and Z ^H23 each represent a carbon atom or a nitrogen atom. Z ^H21 , Z ^H22 and Z ^H23 are preferably carbon atoms.

Q ^H21 represents an atomic group necessary for bonding with X ^H2 and Z ^H21 to form a ring. The ring formed by Q ^H21 is preferably a 5-membered ring or a 6-membered ring, more preferably an aromatic 5-membered ring or an aromatic 6-membered ring, still more preferably a nitrogen-containing aromatic hetero 5-membered ring, A nitrogen-containing aromatic hetero 6-membered ring, more preferably a nitrogen-containing aromatic hetero 6-membered ring.
Specific examples of the ring formed by Q ^H21 include benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrole ring, thiophene ring, furan ring, oxazole ring, isoxazole ring, thiazole ring, Examples include a thiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a tetrazole ring and a ring in which the above aromatic rings are all or partly reduced, preferably a pyridine ring or a pyrimidine ring. , A pyridazine ring, a pyrazine ring, an oxazole ring and an imidazole ring, more preferably a pyridine ring, a pyrazine ring, an oxazole ring and an imidazole ring, and still more preferably an imidazole ring. The ring formed by Q ^H21 may further form a condensed ring with another ring, and may have a substituent. As the substituent, those ^{exemplified as} the substituent for Q ^{H1 in} formula (H-1) can be used.

Q ^H22 represents an atomic group necessary for bonding with Z ^H22 and Z ^H23 to form a ring. The ring formed by Q ^H21 is preferably a 5-membered ring or a 6-membered ring, more preferably an aromatic 5-membered ring or an aromatic 6-membered ring. Specific examples of the ring formed by Q ^H22 include cyclopentene ring, cyclohexene ring, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring, perylene ring, pyridine ring, quinoline ring, furan ring, thiophene ring, pyrazine Ring, pyrimidine ring, thiazole ring, benzothiazole ring, naphthothiazole ring, oxazole ring, benzoxazole ring, naphthoxazole ring, isoxazole ring, imidazole ring, benzimidazole ring, isoquinoline ring, pyrazole ring, and triazole ring. Is benzene, naphthalene, pyridine, thiophene, pyrazine or pyrimidine, more preferably naphthalene or benzene, and even more preferably benzene. The ring formed by Q ^H22 may further form a condensed ring with another ring, and may have a substituent. As the substituent, those ^{exemplified as} the substituent for Q ^{H1 in} formula (H-1) can be used.

M ² , n ² and m ² have the same meanings as M ¹ , n ¹ and m ¹ , respectively, and preferred ranges are also the same.

  In the general formula (H-2), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bond is a single bond. The species is not limited.

In general formula (H-3), X ^H3 may have an oxygen atom, nitrogen atom, sulfur atom, carbon atom, and, if possible, a substituent, and the substituent in general formula (H-1) is What was mentioned as a substituent of ^XH1 is applicable. X ^H3 is preferably an oxygen atom, a sulfur atom or a nitrogen atom, more preferably a nitrogen atom. Y ^H3 represents an oxygen atom, a nitrogen atom, or a sulfur atom, and may have a substituent if possible, and the substituents listed are those listed as the substituent for X ^H1 in the general formula (I). it can. Y ^H3 is preferably an oxygen atom, a sulfur atom, or a substituted or unsubstituted nitrogen atom, more preferably an oxygen atom or a substituted nitrogen atom, and still more preferably an oxygen atom. Z ^H31 , Z ^H32 and Z ^H33 each represent a carbon atom or a nitrogen atom, and if possible, may have a substituent. Z ^H31 , Z ^H32 and Z ^H33 are preferably carbon atoms.

Q ^H31 represents an atomic group necessary for bonding with X ^H3 and Z ^H33 to form a ring. The ring formed by Q ^H31 is preferably a 5-membered ring or a 6-membered ring, more preferably an aromatic 5-membered ring or an aromatic 6-membered ring, still more preferably a nitrogen-containing aromatic hetero 5-membered ring, A nitrogen-containing aromatic hetero 6-membered ring, more preferably a nitrogen-containing aromatic hetero 6-membered ring. Specific examples of the ring formed by ^QH31 include benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrole ring, thiophene ring, furan ring, oxazole ring, isoxazole ring, thiazole ring, Examples include a thiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a tetrazole ring and a ring in which the above aromatic rings are all or partly reduced, preferably a pyridine ring or a pyrimidine ring. , A pyridazine ring and a pyrazine ring, more preferably a pyridine ring and a pyrazine ring, and still more preferably a pyridine ring. The ring formed by Q ^H31 may further form a condensed ring with another ring, and may have a substituent. As the substituent, those ^{exemplified as} the substituent for Q ^{H1 in} formula (H-1) can be used.

Q ^H32 represents an atomic group necessary for bonding with Z ^H32 or Z ^H33 to form a ring. The ring formed by Q ^H32 is preferably a 5-membered ring or a 6-membered ring, more preferably an aromatic 5-membered ring or an aromatic 6-membered ring. Specific examples of the ring formed by Q ^H32 include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrole ring, a thiophene ring, a furan ring, an oxazole ring, an isoxazole ring, a thiazole ring, Examples include a thiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a tetrazole ring and a ring in which the above aromatic rings are all or partially reduced, preferably a benzene ring, a pyridine ring. And a pyrazine ring, more preferably a benzene ring and a pyridine ring, and still more preferably a benzene ring. The ring formed by Q ^H32 may further form a condensed ring with another ring, and may have a substituent. As the substituent, those ^{exemplified as} the substituent for Q ^{H1 in} formula (H-1) can be used.

M ³ , n ³ and m ³ have the same meanings as M ¹ , n ¹ and m ¹ , respectively, and preferred ranges are also the same.

  In the general formula (H-3), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bond is a single bond. The species is not limited.

  Of the metal complexes represented by the general formula (H-2), a metal complex represented by the general formula (H-4) is more preferable.

In general formula (H-4), X ^H41 and X ^H42 each represent a carbon atom or a nitrogen atom. The bond between X ^H41 and the nitrogen atom and between X ^H42 and the carbon atom may be a single bond or a double bond. Q ^H41 and Q ^H42 each represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring. M ⁴ represents a metal ion. n ⁴ represents an integer of 1 or more. L ^H represents a ligand, and m ⁴ represents an integer of 0 or more.

In the general formula (H-4), the bond between X ^H41 and the nitrogen atom and between X ^H42 and the carbon atom is drawn with two lines, a solid line and a dotted line. It represents that it may be a double bond.

Q ^H41 represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring including X ^H41 and a nitrogen atom. The ring containing Q ^H41 may have a substituent, and examples of the substituent include the following substituent group A.

(Substituent group A)
An alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n- Decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, For example, vinyl, aryl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, For example, propargyl, 3-pentynyl and the like are mentioned), an aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 6 carbon atoms) 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.), a substituted carbonyl group (preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, Particularly preferred are those having 1 to 12 carbon atoms, such as acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, etc.), amino groups (preferably having 0 to 20 carbon atoms, and more). Preferably it is C1-C16, Most preferably, it is C1-C12, for example, a dimethylamino, methylcarbonylamino, an ethylsulfonylamino, a dimethylaminocarbonylamino group, a phthalimide group etc.), a sulfonyl group (preferably). 1 to 20 carbons, more preferably 1 carbons 16, particularly preferably having 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfo group, carboxyl group, heterocyclic group (aliphatic heterocyclic group, aromatic heterocyclic group. , An oxygen atom, a sulfur atom, or a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as imidazolyl, pyridyl, furyl, Piperidyl, morpholino, benzoxazolyl, triazolyl group, etc.),

A hydroxy group, an alkoxy group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as a methoxy group and a benzyloxy group), and aryloxy. A group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, such as a phenoxy group and a naphthyloxy group), a halogen atom (preferably fluorine). Atom, chlorine atom, bromine atom, iodine atom), thiol group, alkylthio group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio group) An arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, and particularly preferably 6 to 12 carbon atoms). For example, a phenylthio group), a cyano group, a silyl group (preferably having 0 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 18 carbon atoms. A phenylsilyl group, a t-butyldiphenylsilyl group, etc.). These substituents may be further substituted. The ring containing Z ¹¹ may form a condensed ring with other rings.

Examples of the ring containing Q ^H41 include pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine ring, phenazine ring, phenanthroline. Ring, naphthyridine ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzoselenazole ring, indazole ring , Isothiazole ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imidazopyridine ring, purine Ring, imidazoline ring and the like, preferably pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole A ring, a thiazole ring, a benzothiazole ring, a triazole ring, a benzotriazole ring, and an imidazopyridine ring, and more preferably an imidazopyridine ring.

Q ^H42 represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring including X ^H42 and a carbon atom (a carbon atom bonded to an oxygen atom in the formula). The ring containing Q ^H42 may have a substituent, and as the substituent, those ^exemplified as the substituent of the ring containing Q ^H41 can be applied, and the preferred range is also the same.

Examples of the ring containing Q ^H42 include cyclopentene, cyclohexene, benzene, naphthalene, anthracene, phenanthrene, pyrene, perylene, pyridine, quinoline, furan, thiophene, pyrazine, pyrimidine, thiazole, benzothiazole, naphthothiazole, oxazole, and benzoxazole. Naphthoxazole, isoxazole, selenazole, benzoselenazole, naphthoselenazole, imidazole, benzimidazole, naphthimidazole, isoquinoline, pyrazole, triazole and the like. The ring containing Q ^H42 is preferably an aromatic ring. For example, benzene, naphthalene, anthracene, pyridine, thiophene, pyrazine, and pyrimidine are preferable, benzene and naphthalene are more preferable, and benzene is more preferable. The substituent of Q ^{H41 and} the substituent of Q ^H42 may be bonded to form a ring.

M ⁴ , n ⁴ and m ⁴ have the same meanings as M ¹ , n ¹ and m ¹ , respectively, and preferred ranges are also the same.

Metal complex represented by the general formula (H-4) is more preferably a metal complex der represented by the general formula (H-5) is, for use in the present invention.

In general formula (H-5), R ^H51 and R ^H52 represent a hydrogen atom or a substituent. As the substituent, for example, those exemplified as the substituent for Q ^{H1 in} formula (H-1) can be applied. R ^H51 and R ^H52 may combine to form a ring. Examples of the ring formed by combining R ^H51 and R ^H52 include a cycloalkene ring, a benzene ring, and a hetero ring (for example, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrole ring, a thiophene ring, and a furan ring. , Oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, pyrazole ring, triazole ring, oxadiazole ring, thiadiazole ring, tetrazole ring, etc.) It may be condensed with a ring and may further have a substituent.

R ^H51 and R ^H52 are preferably a hydrogen atom, an alkyl group, an aryl group, an aromatic heterocyclic group, or a group that combines with each other to form an aromatic ring, and more preferably a hydrogen atom, an alkyl group, or an aryl group. The group is preferably a group that is bonded to each other to form an aromatic heterocyclic group, and more preferably a hydrogen atom, an aryl group, or a group that is bonded to each other to form an aromatic heterocyclic group.

Z ^H5 represents an oxygen atom, a sulfur atom, —C (R ^H53 ) R ^H54 —, or —NR ^H55 —. R ^H53 and R ^H54 each represent a hydrogen atom or a substituent, and examples of the substituent include those ^{exemplified as} the substituent for X ^{H1 in} formula (H-1). R ^H55 represents a hydrogen atom or a substituent, and examples of the substituent for R ^H55 include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms). For example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include vinyl, aryl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably having 2 to 20 carbon atoms, More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl. An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.), a substituted carbonyl group; (Preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, etc. A substituted sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), hetero A cyclic group (an aliphatic heterocyclic group or an aromatic heterocyclic group, preferably an oxygen atom, a sulfur atom, a nitrogen atom) 1 to 50, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl And a triazolyl group). These substituents may be further substituted. R ^H55 is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and more preferably an alkyl group or an aryl group.

Q ^H5 represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring. The ring containing Q ^H5 may further have a substituent, and may form a condensed ring with other rings. As the substituent, those ^{exemplified as} the substituent for Q ^H1 in formula (H-1) can be used. Examples of the ring containing Q ^H5 include cyclopentene ring, cyclohexene ring, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring, perylene ring, pyridine ring, quinoline ring, furan ring, thiophene ring, pyrazine ring, pyrimidine Ring, thiazole ring, benzothiazole ring, naphthothiazole ring, oxazole ring, benzoxazole ring, naphthoxazole ring, isoxazole ring, imidazole ring, benzimidazole ring, naphthimidazole ring, isoquinoline ring, pyrazole ring, triazole ring, etc. It is done. The ring containing Q ^H5 is preferably an aromatic ring. Preferred are a benzene ring, naphthalene ring, anthracene ring, pyridine ring, thiophene ring, pyrazine ring and pyrimidine ring, more preferred are a benzene ring and a naphthalene ring, and even more preferred is a benzene ring.

M ⁵ , n ⁵ , and m ⁵ are synonymous with M ¹ , n ¹ , and m ¹ , respectively, and preferred ranges are also the same.

  In the general formula (H-5), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bond is a single bond. The species is not limited.

  The metal complex represented by the general formula (H-5) is more preferably a metal complex represented by the general formula (H-6).

In the general formula (H-6), Z ^H6 , M ⁶ , n ⁶ , m ⁶ and Q ^H61 have the same ^{meanings as} Z ^H5 , M ⁵ , n ⁵ , m ⁵ and Q ^{H5 in the} general formula (H-5), respectively. There are also preferred ranges.

Q ^H62 includes a hetero ring (including an aliphatic hetero ring and an aromatic hetero ring. The hetero atom is preferably an oxygen atom, a sulfur atom or a nitrogen atom, preferably 2 to 20 carbon atoms, more preferably 3 to 15 carbon atoms. Particularly preferably 4 to 10 carbon atoms, such as pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrole ring, thiophene ring, furan ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, An imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a tetrazole ring, etc.). The heterocyclic ring formed by Q ^H62 may have a substituent, and examples of the substituent include those ^{listed as} the substituent for Q ^{H1 in} formula (H-1).

  In the general formula (H-6), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bond is a single bond. The species is not limited.

  As the metal complex of the host material in the present invention, for example, a metal complex of an imidazopyridine derivative described in JP-A-2000-302754, JP-A-8-301877, JP-A-8-306489, JP-A-9-279134, JP-A-7- 133348, JP-A 2000-2000684, JP-A 2000-252066, JP-A 2000-247972, JP-A 2000-173777, etc., metal complexes of benzoxazole derivatives, JP-A 2000-302754, JP-A 2000-252067, etc. Metal complexes of oxazole derivatives described in JP-A-8-113576, JP-A-2000-200654, JP-A-2000-247964, JP-A-10-45722, JP-T-2000-515926, etc., JP 2001 131162, JP-A 2000-302754, JP-A 2000-252067, etc., thiazole derivative metal complexes, JP-A 2000-200684, JP-A 10-265478, etc., metal complexes, JP-A 2000 -302754, metal complexes of imidazole derivatives described in JP-A-2000-252067, metal complexes of benzotriazole derivatives and metal complexes of benzopyrazole derivatives described in JP-A-9-111234, JP-A 2000-357588, Metal complexes of hydroxyphenyl-substituted pyridine derivatives described in JP-A-9-176629, etc., metal complexes of hydroxy-substituted benzoquinoline derivatives described in JP-A-9-20886, JP-A 2000-12222, etc., and JP-A-9-20855 Description A metal complex of a hydroxy-substituted pyridoquinoline derivative, a metal complex of a hydroxyphenyl-substituted triazole derivative described in JP-A No. 2000-100570, a metal complex of a hydroxyphenyl-substituted oxadiazole or thiadiazole derivative described in JP-A No. 10-259372, A metal complex of hydroxyphenyl-substituted imidazopyridine described in JP-A No. 2001-57292 and the like, and a metal complex of 8-quinolinol described in JP-A No. 2003-152264 and the like can also be suitably used.

Although the specific example of the metal complex represented by general formula (H-5) of the host material in this invention is enumerated below, this invention is not limited to these.
Here, Exemplified compounds 16, 46, 61 and 68 to 123 are reference examples.

-Configuration of organic EL element-
Next, the configuration of the organic EL element of the present invention will be described.
The organic EL device of the present invention is configured to have an organic compound layer including at least one light emitting layer between a pair of electrodes of an anode and a cathode provided on a substrate. Examples of the organic compound layer other than the light emitting layer include a hole transport layer, a hole injection layer, an electron injection layer, an electron transport layer, and a protective layer.
In addition, each of these layers may have other functions, and the same layer may be laminated. Various materials can be used for forming each layer.

<Anode>
The anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. A material having a work function of 4 eV or more is preferable.
Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide and indium tin oxide (ITO), metals such as gold, silver, chromium and nickel, and these metals and conductive metal oxides. Mixtures or laminates thereof, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene and polypyrrole, and laminates of these with ITO, preferably conductive It is a metal oxide, and ITO is particularly preferable in terms of productivity, high conductivity, transparency, and the like.
The thickness of the anode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 500 nm.

Usually, the anode is formed by layering on the above-mentioned soda-lime glass, non-alkali glass, transparent resin substrate or the like. When glass is used, it is preferable to use non-alkali glass as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. Transparent resin substrates include polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyethylene, polycarbonate, polyethersulfone, polyarylate, allyl diglycol carbonate, polyimide, polycycloolefin, norbornene resin, poly (chlorotrine). Fluoroethylene), Teflon (registered trademark), and polytetrafluoroethylene-polyethylene copolymer.
The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, a thickness of 0.2 mm or more, preferably 0.7 mm or more is usually used.
Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (such as a sol-gel method), a dispersion of indium tin oxide is used. A film is formed by a method such as coating.
The anode can be driven to lower the drive voltage of the element or increase the light emission efficiency by washing or other processing. For example, in the case of ITO, UV-ozone treatment, plasma treatment, etc. are effective.

<Cathode>
The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, etc., and the adhesion, ionization potential, and stability between the negative electrode and the adjacent layer such as the electron injection layer, the electron transport layer, and the light emitting layer. It is selected in consideration of etc.
As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples include alkali metals (for example, Li, Na, K, etc.) and The fluoride or oxide, alkaline earth metal (eg, Mg, Ca, etc.) and the fluoride or oxide thereof, gold, silver, lead, aluminum, sodium-potassium alloy or mixed metal thereof, lithium-aluminum alloy or Examples thereof include mixed metals, magnesium-silver alloys or mixed metals thereof, rare earth metals such as indium and ytterbium, preferably materials having a work function of 4 eV or less, more preferably aluminum, lithium-aluminum alloys or the like. A mixed metal, a magnesium-silver alloy, or a mixed metal thereof.
The cathode can take not only a single layer structure of the above-mentioned compounds and a mixture thereof but also a laminated structure containing the above-mentioned compounds and a mixture thereof. For example, a laminated structure of aluminum / lithium fluoride and aluminum / lithium oxide is preferable.
The thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 1 μm.
For production of the cathode, methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, a coating method, and a transfer method are used, and a metal can be vapor-deposited alone or two or more components can be vapor-deposited simultaneously. Furthermore, a plurality of metals can be vapor-deposited simultaneously to form an alloy electrode, or a previously prepared alloy may be vapor-deposited.
The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

<Organic compound layer>
The organic compound layer in the present invention will be described.
The organic EL device of the present invention has a plurality of organic compound layers including a light emitting layer, and other organic compound layers other than the light emitting layer include a hole transport layer, an electron transport layer, a charge blocking layer, and a hole. Examples thereof include an injection layer and an electron injection layer.
Each layer constituting the organic compound layer is formed by a dry film forming method such as vapor deposition or sputtering, dipping, spin coating, dip coating, casting, die coating, roll coating, bar coating, gravure coating, etc. The film can be suitably formed by any of a wet film forming method, a transfer method, a printing method, and the like.

(Light emitting layer)
The light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.
As the light emitting layer in the present invention, a charge transport function and a light emitting function are separated to obtain better performance, or a phenomenon in which agglomeration occurs in a high concentration light emitting material and the excited state is non-radiatively deactivated (concentration quenching). In order to prevent this, the charge transport material (host material) is doped with the light emitting material as a dopant.

-Charge transport material (host material)-
As the host material applied to the light emitting layer, the compound of the present invention can be used alone, or may be used by mixing with other compounds. Examples of the host material used in combination include carbazole and derivatives thereof (for example, those described in “Applied Physics Letters”, 1999, Vol. 74, No. 3, p. 442), tri Benzazepine and derivatives thereof (JP-A Nos. 10-59943, 10-219241, 10-316875, 10-324680, 10-330365, JP-A 2001-97953), triazole and derivatives thereof ( US Pat. No. 3,121,197), oxazole and derivatives thereof (US Pat. No. 3,257,203), imidazole and derivatives thereof (Japanese Patent Publication No. 37-16096), polyarylalkanes and derivatives thereof (US Pat. Nos. 3,615,402 and 3,820,983). No. 9, No. 3542544, JP-B Nos. 45-555, 51-10983, JP-A Nos. 51-93224, 55-17105, No. 56-4148, No. 55-108667, No. 55-156953 No. 56-36656), polyarylbenzenoids and derivatives thereof (JP-A-10-255985, JP-A-2002-260861), arylamines and derivatives thereof (US Pat. Nos. 3,567,450, 3,180,703, 3,240,597). No. 3,658,520, No. 4,232,103, No. 4,175,961, No. 401,376, Japanese Examined Patent Publication No. 49-35702, No. 39-27777, JP-A Nos. 55-144250, No. 56-119132, No. 56-22437. West German Patent No. 1105518), styryl anthracene Derivatives thereof (Japanese Patent Laid-Open No. 56-46234), stilbenes and derivatives thereof (Japanese Patent Laid-Open Nos. 61-210363, 61-228451, 61-14642, 61-72255, 62-47646, etc.) 62-36674, 62-10652, 62-30255, 60-93445, 60-94462, 60-174749, 60-175052), aromatic tertiary amine compounds and styryl. Amine compounds (Japanese Patent Laid-Open Nos. 63-295695, 53-27033, 54-58445, 54-149634, 54-64299, 55-79450, 55-144250, 56- 119132, 61-295558, 61-98353, JP-A-8-239655, US Patent 4127412), aromatic dimethylidene compounds (JP-A-6-330034), pyrazoline derivatives and pyrazolone derivatives (US Pat. Nos. 3,180,729, 4,278,746, JP-A-55-88064, 55-88065, and 49). No. -105537, No. 55-51086, No. 56-80051, No. 56-88141, No. 57-45545, No. 54-112737, No. 55-74546), Phenylenediamine and its derivatives (US Pat. 3615404, JP-B-51-10105, JP-B-46-3712, JP-B-47-25336, JP-A-54-53435, JP-B-54-110536, JP-B-54-11925), amino-substituted chalcones and their derivatives ( US Pat. No. 3,526,501), fluorenone and its Derivatives (Japanese Patent Laid-Open No. 54-11037), hydrazones and derivatives thereof (US Pat. No. 3,717,462, Japanese Patent Laid-Open Nos. 54-59143, 55-52063, 55-52064, 55-46760, 55) -85495, 57-11350, 57-148799), silazane and derivatives thereof (US Pat. No. 4,950,950), porphyrin compounds (Japanese Patent Laid-Open No. 63-295695), anthraquinodimethane and derivatives thereof, and Anthrone and its derivatives (Japanese Patent Laid-Open Nos. 57-149259, 58-55450, 63-104061, Japanese Patent Laid-Open Nos. 61-225151, 61-233750), diphenoquinone and its derivatives, thiopyran dioxide and Derivatives thereof and carbodiimides and derivatives thereof (" Rimmer Purepurintsu, Japan (Polymer Preprints, Japan) ", 1988, Vol. 37, No. 3, p. 681), fluorenylidenemethane and derivatives thereof (JP-A-60-69657, 61-143765, 61-148159)), distyrylpyrazine and derivatives thereof ("Chemistry Letters", 1990). , P.189, JP-A-2-252793, JP-A-5-178842), heterocyclic tetracarboxylic acid anhydrides and derivatives thereof ("Japanese Journal of Applied Physics", 1988, 27). L269), porphyrin, phthalocyanine and derivatives thereof (Japanese Patent Laid-Open No. 63-295965), metal complexes of 8-quinolinol and derivatives thereof (Journal of the Institute of Electronics, Information and Communication Engineers, 1990, C) -, P.661), metal complexes having benzoxazole and derivatives thereof as ligands, metal complexes having benzothiazole and derivatives thereof as ligands, and the like.

In order to efficiently transfer energy from the triplet excited state of the host material to the light emitting material, the energy level (T ₁ level) of the lowest triplet excited state of the host material is higher than the T ₁ level of the light emitting material. Is preferably high. Since the T ₁ level of the luminescent material becomes higher as the emission wavelength is shorter, a high T ₁ host material is required in the light emitting layer for a short wave light emitting element, while T ₁ is the highest occupied orbit of the host material ( HOMO) and the lowest unoccupied orbit (LUMO), which are related to the ability to inject and transport charges (generally, the larger the energy difference between HOMO and LUMO, the less the charge is injected and the higher the electrical insulation) Therefore, it is important to select an optimal T ₁ level host material.
In particular, the T ₁ level of the light emitting layer host material for a blue light emitting element having an emission maximum wavelength of 500 nm or less is 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less). Preferably, they are 65 kcal / mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).

The light emitting layer in the present invention is preferably formed by a vapor deposition method.
The vapor deposition method is a vacuum vapor deposition method in which a substance is heated and evaporated under high vacuum (10 ⁻² Pa or less) and a gaseous substance is deposited on a target to form a film from an evaporation source. The heating method for evaporation includes a resistance heating method, a high frequency heating method, an electron beam heating method, a laser heating method, etc., but the resistance heating method is the most common. Further, there are a sputtering method, an ion plating method, a molecular beam epitaxy method, and the like as a method for evaporating the material by a method other than heating, which can be properly used depending on the purpose. As a vapor deposition method in a broader sense, there is a CVD method in which a film is formed by a chemical reaction on the target surface, and the vapor deposition method referred to in this specification includes all these vapor deposition techniques. Details of the vapor deposition method are described in Chapter 8 of "New Format / Vacuum Handbook" (edited by ULVAC, Inc.) published by Ohm.

  In the case of forming a film with a mixture of two or more substances, a mixture of a plurality of substances may be put into one evaporation source to evaporate, but in this method, the composition of the substance in the evaporated gas is kept constant. A difficult method is to fly molecules simultaneously from different evaporation sources. There is also known a method (Japanese Patent No. 3362504) in which a plurality of substances are sequentially laminated on a heated substrate to form a uniform film using diffusion by heat.

The light-emitting layer created by the vapor deposition method does not contain impurities, oxygen, and moisture derived from solvents, binders, etc., compared to the case where it is created by a wet film formation method typified by a spin coating method or an inkjet method. A light emitting layer thin film having a desired film thickness can be easily obtained without being concerned about driving durability and without worrying about dissolving an existing lower layer with a solvent.
Further, by performing masking at the time of vapor deposition, different light emitting materials and host materials can be used for each pixel to have different light emitting characteristics, which is suitable for manufacturing a fine color display with high definition and high image quality.

When the light emitting layer is formed by vapor deposition, it is preferable to contain only a material having a molecular weight of 3000 or less as a material constituting the light emitting layer. In particular, polymer materials such as polymers and oligomers are not preferable because they are low in volatility and difficult to deposit, and the materials themselves have a molecular weight distribution, making it difficult to obtain light emission with good reproducibility.
High molecular weight compounds having a molecular weight of 3000 or more are difficult to evaporate by heating even under high vacuum conditions, and thin film formation by vacuum deposition tends to be difficult.
In particular, when a substance outside the range of 200 or more and 2000 or less is selected, a low molecular weight compound having a molecular weight of 200 or less is too volatile and difficult to form a thin layer upon vacuum deposition. This is because it tends to be difficult to evaporate by heating underneath.
Moreover, from the easiness of vapor deposition, it is preferable that the material which comprises a light emitting layer is not an ionic compound but a neutral molecular compound.
The light-emitting layer thin film formed by vapor deposition is preferably a uniform amorphous thin film (amorphous film) free from defects such as peeling and pinholes, and changes in performance of the light-emitting element when recrystallization occurs over time or heat Therefore, the melting point and the glass transition temperature (Tg) are preferably high. The melting point of the material constituting the light emitting layer is preferably 150 ° C. or higher, more preferably 200 ° C. or higher, further preferably 250 ° C. or higher, and Tg is preferably 70 ° C. or higher, more preferably 100 ° C. or higher, and still more preferably 120 ° C. It is above ℃.
As a host material satisfying the above required performance, a carbazole derivative that has a high T ₁ level, is unlikely to cause crystallization, has a long excited state lifetime, and can be expected to have high emission efficiency is most preferable.

-Luminescent material-
In the present invention, the metal complex E is used as described above, but it can also be used in combination with other light emitting materials. The light-emitting material used in combination may be either a fluorescent compound that emits light from singlet excitons or a phosphorescent compound that emits light from triplet excitons.
Examples of light emitting materials that can be used in combination in the present invention include benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives. , Condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidene compounds, metal complexes of 8-quinolinol derivatives and pyromethene derivatives Various metal complexes represented by transition metal complexes such as genus complex, rare earth complex, iridium trisphenylpyridine complex and platinum porphyrin complex, polymer compounds such as polythiophene, polyphenylene and polyphenylene vinylene, and compounds such as organic silane derivatives .

Although the film thickness of a light emitting layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.
There may be one or a plurality of light emitting layers, and each light emitting layer emits light in a different light emission color, for example, may emit white light as a whole, or may emit white light from a single light emitting layer. May be. When there are a plurality of light emitting layers, each light emitting layer may be formed of a single material or may be formed of a plurality of compounds. For example, in the case of a mixed system including a host material and a light emitting material, the host material may be a single material or a mixture of a plurality of types. The light emitting material may be a single material or a mixture of a plurality of materials.

(Hole injection layer, hole transport layer)
The material contained in the hole injection layer and the hole transport layer has one of the function of injecting holes from the anode, the function of transporting holes, or the function of blocking electrons injected from the cathode. If it is.
The materials constituting the hole injection layer and the hole transport layer include tribenzazepine and derivatives thereof, triazole and derivatives thereof, oxazole and derivatives thereof, oxadiazole and derivatives thereof, imidazole and derivatives thereof, polyarylalkane and derivatives thereof. Derivatives, polyarylbenzenes and derivatives thereof, arylamines and derivatives thereof, styrylanthracene and derivatives thereof, stilbenes and derivatives thereof, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, 8-quinolinol and derivatives thereof Metal complexes, pyrazolines and derivatives thereof, pyrazolones and derivatives thereof, phenylenediamines and derivatives thereof, amino-substituted chalcones and derivatives thereof, fluorenones and derivatives thereof, hydrazones And derivatives thereof is preferably at least one selected from the group of silazane and its derivatives and porphyrin compounds. Preferable examples of these compounds include the same examples as the corresponding compounds described in the section of the host material that can be used in combination.

Further, when the hole transport layer is a layer adjacent to the light emitting layer containing the phosphorescent compound, the triplet excitons generated in the light emitting layer are prevented from moving to the hole transport layer. The energy level (T ₁ level) in the lowest triplet excited state is preferably higher than the T ₁ level of the light emitting material or the host material contained in the light emitting layer. In particular, the T ₁ level of a hole transport material for a blue light emitting device having an emission maximum wavelength of 500 nm or less is preferably 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less), and 65 kcal. / Mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).
As a hole transport material satisfying the above physical property values, a hole transport material described in JP-A No. 2002-1000047 is preferable, and a preferable range of the hole transport material described in JP-A No. 2002-100466 is the same as that of the same specification. As described in the book.
Among the above compound groups, tribenzazepine derivatives can be expected to have high luminous efficiency at high T ₁ , and arylamine derivatives can be expected to improve durability due to high stability. More preferred.
In addition, carbazole, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and derivatives thereof as necessary Can be added.

The thickness of the hole injection layer is not particularly limited, but is usually preferably in the range of 0.2 nm to 1 μm, more preferably 1 nm to 0.2 μm, and further preferably 2 nm to 100 nm. .
The thickness of the hole transport layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and even more preferably 10 nm to 500 nm.
The hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

As a method for forming the hole injection layer and the hole transport layer, a vacuum deposition method, an LB method, a method in which the hole injection transport material is dissolved or dispersed in a solvent, a coating method, an ink jet method, a printing method, or a transfer method is used. It is done.
In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, and the like.

Among the above-described layer forming methods, the hole transport layer is preferably installed by vapor deposition. By installing by the vapor deposition method, a thin film having a uniform and constant film thickness can be formed, and the durability tends to be improved.
When the hole transport layer is installed by vapor deposition, the material of the hole transport layer may be composed of a low molecular organic compound having a molecular weight of 3000 or less and / or a low molecular organic metal compound having a molecular weight of 3000 or less, like the light emitting layer material. preferable.

(Electron injection layer, electron transport layer)
As a material included in the electron injection layer and the electron transport layer, any material having one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode Good.
The organic EL device of the present invention preferably has a layer containing a compound having an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the cathode and the light emitting layer, and has an ionization potential of 5.9 eV or more. It is more preferable to have an electron transport layer.

  Specific examples of materials that can be used for the electron injection layer and the electron transport layer include triazole, oxazole, oxadiazole, imidazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, and fluorenylidenemethane. , Various metal complexes represented by metal complexes of aromatic ring tetracarboxylic acid anhydrides such as styrylpyrazine, naphthalene, and perylene, metal complexes of phthalocyanine, 8-quinolinol, metal phthalocyanine, benzoxazole, and benzothiazole , Organosilanes, and derivatives thereof. Preferable examples of these compounds are the same as the corresponding compounds described in the description of the host material.

  In the organic EL device of the present invention, it is preferable to use a layer containing a compound having an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the cathode and the light emitting layer. It is more preferable to use an electron transport layer having an ionization potential of 5.9 eV or more. By providing a layer (block layer) containing such a compound, it is possible to prevent a decrease in luminous efficiency and deterioration in durability due to holes passing through the light emitting layer and flowing into the electron transport layer.

Further, when the electron transport layer is a layer adjacent to the light emitting layer containing the phosphorescent compound, the lowest triplet of the electron transport material is prevented so that triplet excitons generated in the light emitting layer do not move to the electron transport layer. The energy level (T ₁ level) in the excited state is preferably higher than the T ₁ level of the light emitting material or the light emitting layer host material. In particular, the T ₁ level of a hole transport material for a blue light emitting device having an emission maximum wavelength of 500 nm or less is preferably 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol or less), and 65 kcal. / Mol or more (272 kJ / mol or more) and 80 kcal / mol or less (334 kJ / mol or less).
Examples of other electron transport materials that satisfy the above physical property values include the electron transport materials described in JP-A No. 2002-1000047. A preferable range of the electron transport material described in JP-A No. 2002-1000047 is as described in the same specification.

  In addition, carbazole, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and derivatives thereof as necessary Can be added.

The thickness of the electron injection layer is not particularly limited, but is usually preferably in the range of 0.2 nm to 1 μm, more preferably 1 nm to 0.2 μm, and further preferably 2 nm to 100 nm.
Although the film thickness of an electron carrying layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
As a method for forming the electron injection layer and the electron transport layer, a vacuum deposition method, an LB method, a method in which the electron injection / transport material is dissolved or dispersed in a solvent, a coating method, an ink jet method, a printing method, a transfer method, and the like are used.
In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.
Among the layer forming methods described above, the electron transport layer is preferably installed by vapor deposition. By installing by the vapor deposition method, a thin film having a uniform and constant film thickness can be formed, and the durability tends to be improved.
Moreover, when installing an electron carrying layer by a vapor deposition method, it is preferable that the material of an electron carrying layer also consists of a low molecular organic compound with a molecular weight of 3000 or less and / or a low molecular organometallic compound with a molecular weight of 3000 or less like the light emitting layer material. .

(Protective layer)
The organic EL light-emitting device of the present invention may have a protective layer in order to prevent moisture and oxygen from entering. As a material contained in the protective layer, any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
Specific examples thereof 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, BaO, and Fe ₂ O. ₃ , metal oxides such as Y ₂ O ₃ , TiO ₂ , metal fluorides such as MgF ₂ , LiF, AlF ₃ , CaF ₂ , nitrides such as SiN _x , SiO _x N _y , polyethylene, polypropylene, polymethyl methacrylate A monomer mixture comprising polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer Copolymer obtained by copolymerization, fluorine-containing copolymer having a cyclic structure in the main chain Polymer, 1% by weight of the water absorbing water absorption material, water absorption of 0.1% or less of moisture-proof material, and the like.
There is also no particular limitation on the method for forming the protective layer. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation) (Ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, transfer method can be applied.

<Sealing>
Furthermore, the organic electroluminescent element of this invention may seal the whole element using a sealing container.
Further, a moisture absorbent or an inert liquid may be sealed in a space between the sealing container and the light emitting element. Although it does not specifically limit as a moisture absorber, For example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride Cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, magnesium oxide and the like. The inert liquid is not particularly limited, and examples thereof include fluorinated solvents such as paraffins, liquid paraffins, perfluoroalkanes, perfluoroamines, perfluoroethers, chlorinated solvents, and silicone oils. It is done.

The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Can be obtained.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429, 6023308, and the like can be applied.

  The light-emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, by processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate / ITO layer / organic layer, controlling the film thickness of the substrate / ITO layer / organic layer, etc. It is possible to improve light extraction efficiency and external quantum efficiency.

  The light-emitting element of the present invention may be a so-called top emission type in which light emission is extracted from the anode side.

-Manufacturing method of organic EL element-
As a method for producing the organic EL element of the present invention, a production method suitably used will be described below, but the present invention is not limited thereto.

First, a substrate having an ITO thin film as a transparent electrode is washed with a solvent and then subjected to UV-ozone treatment. Furthermore, a hole injection layer and a hole transport layer are formed in this order on the transparent electrode by a vapor deposition method. A light emitting layer is formed thereon by co-evaporating a metal complex and a host material in a vacuum. The metal complex and the host material are as defined above, and the preferred ranges are also the same. The host material and the metal complex used for the light emitting layer preferably have a molecular weight of 3000 or less, and the material constituting the light emitting layer preferably has a molecular weight of 3000 or less. Vapor deposition is facilitated by setting the molecular weight range to the above range.
As the deposition, a known deposition method can be used. Further thereon, an electron transport layer and an electron injection layer are provided in this order, a patterned mask is placed thereon, and a back electrode (cathode) is deposited by evaporation. A block layer containing an electron transport material can be provided between the electron transport layer and the light emitting layer. A lead wire is connected to each of the anode and the cathode to form a light emitting laminate. The light emitting laminate obtained here is sealed to produce an organic EL element.

  The obtained organic EL element is allowed to emit light by applying a direct current voltage, and a driving durability test is performed with the initial luminance, and the durability can be evaluated by setting the time when the luminance is halved as a half time.

  The light emitting device of the present invention can be suitably used in the fields of display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like. The compounds of the present invention can also be applied to medical uses, fluorescent brighteners, photographic materials, UV absorbing materials, laser dyes, recording media materials, inkjet pigments, color filter dyes, color conversion filters, and the like. is there.

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto.
Preparation of Sample 1 A 150nm thick indium tin oxide (ITO) transparent conductive film deposited on a glass substrate (Geomatic Corp .; electron beam film-formed product; sheet resistance 15Ω) was used with normal photolithography and hydrochloric acid etching. Then, the anode was formed by patterning into stripes having a width of 2 mm. The patterned ITO substrate is cleaned in the order of ultrasonic cleaning with acetone, water with pure water, and ultrasonic cleaning with isopropyl alcohol, then dried with nitrogen blow, and finally with ultraviolet ozone cleaning. installed. After roughly exhausting the apparatus with an oil rotary pump, the apparatus was evacuated with a cryopump until the degree of vacuum in the apparatus was 2 × 10 ⁻⁶ Torr (about 2.7 × 10 ⁻⁴ Pa) or less.

Next, copper phthalocyanine (crystal form is β-type) shown below placed in a molybdenum boat placed in the above apparatus is heated, and the degree of vacuum is 1.4 × 10 ⁻⁶ Torr (about 1.9 × 10 ⁻⁴ Pa), vapor deposition Vapor deposition was performed at a rate of 0.1 nm / second to form a 10 nm-thick hole injection layer (anode buffer layer).

Next, α-NPD ((N, N′-di-α-naphthyl-N, N′-diphenyl) -benzidine) placed in a ceramic crucible disposed in the above apparatus is heated to a tantalum wire around the crucible. The vapor deposition was carried out by heating. A degree of vacuum at the time of vapor deposition was 9.0 × 10 ⁻⁷ Torr (about 1.2 × 10 ⁻⁴ Pa), a vapor deposition rate was 0.2 nm / second, and a 40 nm-thick hole transport layer was formed.

Subsequently, CBP as a light emitting layer host material and iridium complex (Ir (ppy) ₃ ) as a light emitting material were placed in a ceramic crucible, and a film was formed by a binary simultaneous vapor deposition method. The deposition rate of CBP is controlled to 0.1 nm / second, and the deposition rate is controlled so that the iridium complex (Ir (ppy) ₃ ) is contained in an amount of 6% by mass with respect to the host. Laminated on the transport layer. The degree of vacuum during the deposition was 1.3 × 10 ⁻⁶ Torr (about 1.7 × 10 ⁻⁴ Pa).

Further, BAlq ₂ was laminated as a hole blocking layer with a film thickness of 10 nm at a deposition rate of 0.1 nm / second. The degree of vacuum during the deposition was 7.0 × 10 ⁻⁷ Torr (about 0.9 × 10 ⁻⁴ Pa).

Next, Alq ₃ was deposited in the same manner as an electron transport layer on the hole blocking layer. The degree of vacuum during deposition was 6.0 × 10 ⁻⁷ Torr (about 0.8 × 10 ⁻⁴ Pa), the deposition rate was 0.2 nm / second, and the film thickness was 35 nm.

The substrate temperature during vacuum deposition of the hole transport layer, the light emitting layer, the hole blocking layer, and the electron transport layer was maintained at room temperature.

Here, the element on which the electron transport layer has been deposited is once taken out from the vacuum deposition apparatus to the atmosphere, and a 2 mm wide striped shadow mask is orthogonal to the 2 mm anode ITO stripe as a mask for cathode deposition. As in the case of forming an organic layer, the vacuum inside the device is 2 × 10 ^-6 Torr (about 2.7 × 10 ^-4 Pa) or less. It exhausted until it became.

Thereafter, as a cathode, first, magnesium fluoride (MgF ₂ ) is deposited at a deposition rate of 0.1 nm / second using a molybdenum boat at a vacuum degree of 7.0 × 10 ⁻⁶ Torr (about 9.3 × 10 ⁻⁴ Pa) and 1.5 nm. A film was formed on the electron transport layer in a film thickness. Next, aluminum was similarly heated by a molybdenum boat to form an aluminum layer having a thickness of 40 nm at a deposition rate of 0.5 nm / second and a degree of vacuum of 1 × 10 ⁻⁵ Torr (about 1.3 × 10 ⁻³ Pa). Furthermore, in order to increase the conductivity of the cathode, silver is also heated by a molybdenum boat, and the deposition rate is 0.3 nm / second, and the degree of vacuum is 1 × 10 ⁻⁵ Torr (about 1.3 × 10 ⁻³ Pa). Thus, a silver layer having a thickness of 40 nm was formed to complete the cathode. The substrate temperature during the deposition of the above three-layer cathode was kept at room temperature.

  As described above, an organic electroluminescent element having a light emitting area portion having a size of 2 mm × 2 mm was obtained.

Preparation of Samples 2 to 11 In the preparation method of Sample 1, the light emitting layer host material and the light emitting material were changed as shown in Table 1, and Samples 2 to 11 were prepared.

Evaluation was performed by the following method using the light-emitting element obtained above.
Using a KEITHLEY source measure unit type 2400, a direct current voltage was applied to the organic EL element to emit light, and the initial light emission performance was measured.
The light emission efficiency was expressed as the external quantum efficiency (η100) (%) as the light emission efficiency at 100 cd / m ² . In addition, the driving durability is shown in Table 1 in which a driving durability test was performed at an initial luminance of 1000 cd / m ² , and the half time (T _1/2 ) (hr) was the time when the luminance was halved.

  From Table 1, it is understood that the sample using the host material used in the present invention has high external quantum efficiency. Furthermore, it can be seen that a light-emitting element having high external quantum efficiency and excellent driving durability can be obtained by combining the light-emitting materials used in the present invention. Furthermore, the utility of the present invention is understood over a wide range of emission wavelengths.

Claims (6)

An organic electroluminescence device having an organic compound layer including at least one light emitting layer between a pair of electrodes, the light emitting layer including at least one light emitting material and at least one host material, An organic electroluminescent element in which the light-emitting material is a metal complex represented by the following general formula (X3) that emits phosphorescence, and the metal complex that functions as a host material is represented by the following general formula (H-5).

(In the general formula (X3), M ^X3 is a metal ion selected from the group consisting of platinum ion, iridium ion, rhenium ion, palladium ion, rhodium ion, ruthenium ion, copper ion, europium ion, gadolinium ion and terbium ion. Y ^X31 to Y ^{X36 each} represents a carbon atom, a nitrogen atom, or a phosphorus atom, L ^{X31 to} L ^{X34 each} represents a single bond, a double bond, or a linking group, and a bond between M ^X3 and Y ^X31 to Y ^X36. Each may be a coordination bond or a covalent bond.)

(In the general formula (H-5), R ^H51 and R ^H52 represent a hydrogen atom or a substituent. Z ^H5 represents an oxygen atom, a sulfur atom, or —NR ^H55 —. R ^H53 , R ^H54 and R ^H55 represent Represents a hydrogen atom or a substituent, Q ^H5 represents an atomic group necessary to form a 5-membered ring or a 6-membered ring, M ⁵ represents a metal ion, n ⁵ represents an integer of 1 or more, L ^H Represents a ligand, and m ⁵ represents an integer of 0 or more, and the bond type between each atom in the formula may be a single bond, a double bond, a triple bond, or a coordination bond.) The organic electroluminescent element according to claim 1, wherein Y ^{X31 to} Y ^X36 in the general formula (X3) are a carbon atom or a nitrogen atom. ^3. The organic electroluminescent device according to claim 1, wherein Y ^X31 , Y ^X33 and Y ^X35 in the general formula (X3) are nitrogen atoms, and Y ^X32 , Y ^X34 and Y ^X36 are carbon atoms. The organic electroluminescent element of any one of Claims 1-3 by which the metal complex which functions as a host material is represented by the following general formula (H-6).

(Wherein, Z ^H6 is an oxygen atom, a sulfur atom, it was or -NR ^H65 - a representative .R ^H65 is .Q ^H61 represents a hydrogen atom or a substituent necessary for forming a 5-membered or 6-membered ring Q ^H62 represents an atomic group necessary for forming a heterocycle, M ⁶ represents a metal ion, n ⁶ represents an integer of 1 or more, L ^H represents a ligand, m ⁶ represents an integer of 0 or more, and the bond type between each atom in the formula may be a single bond, a double bond, a triple bond, or a coordination bond.) The organic electroluminescent element according to claim 1, wherein the central metal M ^x3 in the general formula (X3) is iridium.   An organic electroluminescent device comprising at least one light emitting layer between a pair of electrodes, comprising an exciton block layer, a hole injection layer, a hole block layer and an electron transport layer in addition to a hole transport layer and a light emitting layer The organic electroluminescent device according to claim 1, comprising at least one layer selected from the group.