TW201414697A - Organic electroluminescence element - Google Patents

Abstract

This organic electroluminescence element is characterized by being provided with a positive electrode, a negative electrode disposed opposite of the positive electrode, and an organic layer disposed between the positive electrode and the negative electrode and including at least a light-emitting layer, wherein said light-emitting layer contains an anthracene derivative represented by general formula (1) and a fluoranthene derivative represented by general formula (21). Z1 in general formula (1) is represented in general formula (2).

Description

Organic electroluminescent element

The present invention relates to organic electroluminescent elements.

An organic electroluminescence device (hereinafter referred to simply as an organic EL device) using an organic substance is expected to be used as a solid-state light-emitting large-area full-color display element, and many developments are underway. In general, an organic EL device is composed of a light-emitting layer and a counter electrode having a pair of the light-emitting layers. If an electric field is applied between the two electrodes, electrons can be injected from the cathode side, and holes can be injected from the anode side. Furthermore, the electrons are re-bonded to the holes in the light-emitting layer to generate an excited state, and when the excited state returns to the base state, energy is released as light.

The conventional organic EL device has a higher driving voltage, lower luminance, and lower luminous efficiency than the inorganic light-emitting diode. Moreover, the deterioration of characteristics is also remarkable, and it has not reached the stage of practical use. Recently, organic EL elements have been slowly improved, but they are required to have high luminous efficiency, long life, and improved color reproducibility.

The performance of the organic EL element is slowly improved by the improvement of the luminescent material for organic EL. Especially the color of the blue organic EL element is pure The upward direction (short wavelength of the emission wavelength) is an important technique for improving the color reproducibility of the display.

In the document 1 (International Publication No. 2007/100010), an organic EL device having a light-emitting layer containing an alkadiene ruthenium derivative as a dopant material and an aryl-substituted fluorene derivative as a host material is disclosed. In addition, in the literature 1, it is disclosed that the organic EL device having the light-emitting layer can obtain a long life and a blue light emission with high light-emitting efficiency.

However, the organic EL device described in Document 1 is not sufficient in efficiency and life. When an organic EL device is used as a light source of an electronic device such as an illumination device or a display device, the efficiency is required to be improved and the life is longer.

Accordingly, an object of the present invention is to provide an organic electroluminescence device which emits light with low voltage, high efficiency, and long life.

[1]

An organic electroluminescence device according to an aspect of the present invention includes an anode, a cathode disposed opposite to the anode, an organic layer provided with at least a light-emitting layer between the anode and the cathode, and the light-emitting layer The layer contains an anthracene derivative represented by the following general formula (1) and an alkadiene ruthenium derivative represented by the following general formula (21).

[In the above general formula (1), any one of R ¹⁰¹ ~ R ¹¹⁰ c is a single bond, a bond to L ^1, is not bonded to L ¹ for the R ¹⁰¹ ~ R ¹¹⁰ each independently represent a selected a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substitution or The unsubstituted ring forms an aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, an arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, and an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring which forms any one of 5 to 30 atomic groups, L ^{1 is} selected from a single bond or a linking group, and the aforementioned linking group forms a carbon from a substituted or unsubstituted ring. The 6 to 30 aromatic hydrocarbon ring structure removes the (a+1)-valent residue formed by (a+1) hydrogen atoms, and the substituted or unsubstituted ring forms a heterocyclic structure of 5 to 30 atoms. a (a+1)-valent residue formed by (a+1) hydrogen atoms or a structure in which at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure is bonded to 2 to 4 (a+1) valence of (a+1) hydrogen atoms removed Residues, and a, b, and c each represent an integer of 1 to 4.

Z ¹ represents the structure shown by the following general formula (2). ]

[R ¹¹⁹ to R ¹²⁰ in the above general formula (2) each independently represents an alkyl group selected from a hydrogen atom, a substituted or unsubstituted carbon number of 1 to 20, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An alkyl group, a substituted or unsubstituted arylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring forming atomic number 5 to 30. Any one of R heterocyclic groups, R ¹¹¹ to R ¹¹⁸ is a single bond for bonding with L ¹ , and R ¹¹¹ to R ¹¹⁸ not used for bonding with L ¹ are independently represented and Not used synonymous with R ¹⁰¹ ~ R ¹¹⁰ bonded to L ¹ .

Further, among the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ , at least one of the adjacent two groups The substituent has a ring structure represented by the following general formula (3). ]

[In the above general formula (3), y ¹ and y ² represent the bonding positions of the adjacent groups among R ¹¹¹ to R ¹¹⁸ of the above general formula (2).

R ¹²¹ to R ¹²⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon. The alkoxy group of 1 to 20, the substituted or unsubstituted ring forms an aryloxy group having 6 to 20 carbon atoms, and the substituted or unsubstituted ring forms an arylthio group having 6 to 20 carbon atoms, and a substituted or unsubstituted ring is formed. The aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted ring forms any one of 5 to 30 heterocyclic groups.

In the above general formula (2), any one of R ¹¹¹ to R ¹¹⁸ which does not form a ring, and any one of R ¹²¹ to R ¹²⁴ of the above general formula (3) is a single bond, and is used for the general formula (1). ) L ¹ bond. ]

[In the above general formula (21), R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ each independently represent a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a decyl group, a carboxyl group, a substitution or no Substituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number 7~ 30 arylalkyl, substituted or unsubstituted ring to form an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form an arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number of 2 to 50 The alkoxycarbonyl group, the substituted or unsubstituted ring forms an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted ring-forming atom. The first group of 5 to 30 heterocyclic groups is selected.

The R ²³ system is selected from the group consisting of a second group of hydrogen atoms removed from the first group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ .

The R ²⁴ system is selected from the group consisting of the first group of aromatic hydrocarbon groups and heterocyclic groups represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ .

R ²⁷ and R ³² each independently represent a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a decyl group and the like, which are removed from the first group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ . The fourth group consisting of carboxyl groups is selected.

Further, R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , And R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring, and in the case where a saturated or unsaturated ring is not formed, the ring system is substituted or unsubstituted.

R ²¹ to R ²³ and R ²⁵ to R ³² are excluded from the monovalent group derived from benzo[k]propadienyl fluorene.

R ²³ is different from R ²⁴ .

Any of R ²³ and R ²⁴ is excluded from the α-naphthyl group. ]

According to the present invention, it is possible to provide an organic electroluminescence element which is driven at a low voltage and emits light with high efficiency and long life.

1‧‧‧Organic EL components

2‧‧‧Substrate

3‧‧‧Anode

4‧‧‧ cathode

5‧‧‧Lighting layer

6‧‧‧ hole transport layer

7‧‧‧Electronic transport layer

10‧‧‧Organic layer

Fig. 1 is a view showing an example of a schematic configuration of an organic electroluminescence device according to an embodiment of the present invention.

Form of implementing the invention

(Elements of organic EL elements)

Hereinafter, the element configuration of the organic EL device of the present invention will be described.

The organic EL device of the present invention has an organic layer between a pair of electrodes. The organic layer has at least one layer of an organic compound. The organic layer may contain an inorganic compound.

In the organic EL device of the present invention, at least one of the organic layers has a light-emitting layer. Therefore, the organic layer may be composed of, for example, a light-emitting layer of one layer, or may be provided in an organic EL device such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer. The layer used.

A representative element configuration of the organic EL element is exemplified

(a) anode / luminescent layer / cathode

(b) Anode/hole injection ‧ Transport layer / luminescent layer / cathode

(c) Anode / luminescent layer / electron injection ‧ transport layer / cathode

(d) Anode/hole injection ‧ Transport layer / luminescent layer / Electron injection ‧ Transport layer / Cathode

(e) Anode/hole injection ‧ transport layer / luminescent layer / barrier layer / electron injection ‧ transport layer / cathode, etc.

Among the above, the configuration of (d) is preferably used, and of course, it is not limited thereto.

Further, the above-mentioned "light-emitting layer" is an organic layer having an illuminating function, and when a doping system is used, it contains a host material and a dopant material. At this time, the host material mainly has a function of causing the electrons to re-bond with the holes and enclosing the excitons in the light-emitting layer, and the doping material has a function of causing the excitons obtained by the re-bonding to emit light more efficiently. In the case of a calendering element, the host material mainly has a function of encapsulating the excitons generated by doping into the luminescent layer.

The above-mentioned "hole injection ‧ transport layer" means "at least one of a hole injection layer and a hole transport layer", and "electron injection ‧ transport layer" means "at least one of an electron injection layer and an electron transport layer" One." Here, when the hole injection layer and the hole transport layer are provided, the hole injection layer is preferably provided on the anode side. Further, when the electron injecting layer and the electron transporting layer are provided, the electron injecting layer is preferably provided on the cathode side.

In the present invention, the term "electron transport layer" means an organic layer having the highest electron mobility among the organic layers of the electron transporting region existing between the light-emitting layer and the cathode. When the electron transporting region is composed of one layer, the layer is an electron transporting layer. In addition, as shown in the configuration (e), the organic EL device of the luminescent type is used for preventing diffusion of excitation energy generated in the luminescent layer, and is used for a barrier layer having a high degree of electron mobility. The organic layer adjacent to the light-emitting layer and the electron-transport layer does not necessarily correspond to the electron transport layer.

Fig. 1 shows a schematic configuration of an example of an organic EL device in an embodiment of the present invention.

The organic EL element 1 is a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.

The organic layer 10 has a light-emitting layer 5 containing a host material and a dopant material. Further, the organic layer 10 is between the light-emitting layer 5 and the anode 3, and has a hole Transport layer 6. Further, the organic layer 10 is provided between the light-emitting layer 5 and the cathode 4, and has an electron transport layer 7.

(lighting layer)

‧Main material

As the host material used in the organic EL device of the present invention, an anthracene derivative represented by the following general formula (1) can be used.

In the above general formula (1), any of R ¹⁰¹ to R ¹¹⁰ is a single bond, and is used for bonding with L ¹ .

In the above general formula (1), R ¹⁰¹ to R ^{110 which} are not used for bonding with L ¹ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substitution or a no Substituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring forming aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted ring formed The arylthio group having 6 to 20 carbon atoms, the substituted or unsubstituted ring may form an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring may form any one of heterocyclic groups having 5 to 30 carbon atoms.

In the above general formula (1), L ^{1 is} selected from either a single bond or a linking group.

In the above general formula (1), the linking group is formed by a substituted or unsubstituted ring forming an aromatic hydrocarbon ring having 6 to 30 carbon atoms to form (a+1) a hydrogen atom. a residue having a ring number of 5 to 30 formed by a substituted or unsubstituted ring to remove (a+1) a residue of (a+1) a hydrogen atom, or a ring of the above aromatic hydrocarbon At least one of the structure and the heterocyclic structure is bonded to the (a+1)-valent residue obtained by removing (a+1) hydrogen atoms in the formed structure of 2 to 4.

In the above general formula (1), a, b, and c each represent an integer of 1 to 4. The a of the above general formula (1) is preferably 1 or 2. The b of the above general formula (1) is preferably one.

In the above general formula (1), Z ¹ represents a structure represented by the following general formula (2).

[R ¹¹⁹ to R ¹²⁰ in the above general formula (2) each independently represents an alkyl group selected from a hydrogen atom, a substituted or unsubstituted carbon number of 1 to 20, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An alkyl group, a substituted or unsubstituted arylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring forming atomic number 5 to 30. Any one of the heterocyclic groups, any of R ¹¹¹ to R ¹¹⁸ is a single bond for bonding with L ¹ , and R ¹¹¹ to R ¹¹⁸ not used for bonding with L ¹ are independently represented and Not used synonymous with R ¹⁰¹ ~ R ¹¹⁰ bonded to L ¹ .

Further, among the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ , at least one of the adjacent two groups The substituent has a ring structure represented by the following general formula (3). ]

In the above general formula (3), y ¹ and y ² represent the bonding positions of the adjacent groups among R ¹¹¹ to R ¹¹⁸ of the above general formula (2).

R ¹²¹ to R ¹²⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon. The alkoxy group of 1 to 20, the substituted or unsubstituted ring forms an aryloxy group having 6 to 20 carbon atoms, and the substituted or unsubstituted ring forms an arylthio group having 6 to 20 carbon atoms, and a substituted or unsubstituted ring is formed. The aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted ring forms any one of 5 to 30 heterocyclic groups.

In the above general formula (2), any one of R ¹¹¹ to R ¹¹⁸ which does not form a ring, and any one of R ¹²¹ to R ¹²⁴ of the above general formula (3) is a single bond, and is used for the general formula (1). ) L ¹ bond.

Further, it is preferable that Z ¹ in the above general formula (1) is represented by any ^one of the following general formulas (2-4), (2-5), and (2-6).

Ar ¹⁶¹ to Ar ¹⁶² in the above general formula (2-4), Ar ¹⁷¹ to Ar ¹⁷² in the above general formula (2-5), and Ar ¹⁸¹ to Ar ¹⁸² in the above general formula (2-6) are each independently The expression is synonymous with R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Any one of R ¹⁶¹ to R ¹⁷⁰ in the above general formula (2-4) has a single bond for bonding with L ¹ , and R ¹⁶¹ to R ^{170 which} are not used for bonding with L ¹ are independently represented. And is not synonymous with R ¹⁰¹ ~ R ^{110 which is} not bonded to L ¹ .

Any one of R ¹⁷¹ to R ¹⁸⁰ in the above general formula (2-5) is a single bond for bonding with L ¹ , and R ¹⁷¹ to R ¹⁸⁰ not used for bonding with L ¹ are each independently represented. And is not synonymous with R ¹⁰¹ ~ R ^{110 which is} not bonded to L ¹ .

Any one of R ¹⁸¹ to R ¹⁹⁰ in the above general formula (2-6) has a single bond for bonding with L ¹ , and R ¹⁸¹ to R ¹⁹⁰ not used for bonding with L ¹ are independently represented. And is not synonymous with R ¹⁰¹ ~ R ^{110 which is} not bonded to L ¹ .

At least one of R ¹⁰⁹ and R ¹¹⁰ of the above general formula (1) is preferably a single bond used in the bonding of L ¹ .

Alternatively, at least either of R ¹⁰¹ to R ¹⁰⁴ of the above general formula (1) is preferably a single bond used in the bonding of L ¹ .

Alternatively, R ¹⁰² of the above general formula (1) is preferably a single bond used in the bonding of L ¹ .

R ¹⁰⁹ of the above general formula (1) is formed by a ring selected from a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted ring to form a heterocyclic group having 5 to 30 atoms. Good.

Then, R ¹⁰⁹ of the above general formula (1) is preferably as shown by the following general formula (11).

In the above general formula (11), Ar ¹ represents a group selected from a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring to form a heterocyclic group having 5 to 30 atoms. .

In the above general formula (11), each of the Ra systems is synonymous with R ¹⁰¹ to R ^{110 which} are not used for the L ¹ bonding in the above general formula (1).

In the above general formula (11), d represents an integer of 1 to 4.

In the above general formula (11), when d is 2 to 4, the plural Ra may be the same or different.

Further, it is preferred that the R ^109- substituted or unsubstituted ring of the above general formula (1) forms a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms.

Further, the R ¹⁰⁹ -substituted or unsubstituted ring of the above (1) forms a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms, and the above-mentioned R ¹¹⁰ of the general formula (1) is a single bond for bonding with L ¹ . Good.

Further, in the above general formula (1), a is 1 and the linking group is formed by a ring of a substituted or unsubstituted ring, and an aromatic hydrocarbon ring having 6 to 30 carbon atoms is used to remove two hydrogen atoms. Preferably, the substituted or unsubstituted ring forms a divalent residue of the aromatic hydrocarbon ring structure having 6 to 10 carbon atoms. Better and better phenyl.

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (4) or the following general formula (5).

In the above general formula (4) and the above general formula (5), R ¹⁰¹ to R ¹⁰⁸ and R ¹¹⁰ to R ¹¹⁸ each independently represent R ¹⁰¹ which is not used for bonding with L ¹ in the above general formula (1). ~R ^{110 is} synonymous.

In the above general formula (4) and the above general formula (5), R ¹¹⁹ to R ¹²⁰ each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

In the above general formula (4) and the above general formula (5), the L ¹ system is synonymous with L ¹ in the above general formula (1).

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formulas (6) to (9).

In the above general formulas (6) to (9), R ¹⁰¹ to R ¹⁰⁸ and R ¹¹⁰ to R ¹¹⁸ each independently represent R ¹⁰¹ to R ^{110 which are} not used for bonding with L ¹ in the above general formula (1). Synonymous.

In the above general formulas (6) to (9), R ¹¹⁹ to R ¹²⁰ each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Further, in the above general formula (6) and the above general formula (7), the anthracene ring and the anthracene ring system are bonded to a carbon atom of a 6-membered ring constituting the benzene ring.

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (12).

In the above general formula (12), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁷¹ , and R ¹⁷³ to R ¹⁸⁰ each independently represent R ¹⁰¹ ~ which is not used for bonding with L ¹ in the above general formula (1). R ^{110 is} synonymous.

In the above general formula (12), Ar ¹⁷¹ to Ar ¹⁷² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

In the above general formula (12), the L ¹ system is synonymous with L ¹ in the above general formula (1).

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (13) or the following general formula (14).

In the above general formula (13) or the above general formula (14), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁷¹ , and R ¹⁷³ to R ¹⁸⁰ are each independently represented and are not used in the above general formula (1). R ¹⁰¹ to R ^{110 of the} L ¹ bond are synonymous.

In the above general formula (13) or the above general formula (14), Ar ¹⁷¹ to Ar ¹⁷² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Further, in the above general formula (13), the anthracene ring and the benzofluorene ring system are bonded to the carbon atom of the 6-membered ring constituting the benzene ring.

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (15).

In the above general formula (15), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁶¹ , and R ¹⁶³ to R ¹⁷⁰ each independently represent R ¹⁰¹ ~ which is not used for bonding with L ¹ in the above general formula (1). R ^{110 is} synonymous.

In the above general formula (15), Ar ¹⁶¹ to Ar ¹⁶² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

In the above general formula (15), the L ¹ system is synonymous with L ¹ in the above general formula (1).

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (16) or the following general formula (17).

In the above general formula (16) or the above general formula (17), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁶¹ , and R ¹⁶³ to R ¹⁷⁰ are each independently represented and are not used in the above general formula (1). R ¹⁰¹ to R ^{110 of the} L ¹ bond are synonymous.

In the above general formula (16) or the above general formula (17), Ar ¹⁶¹ to Ar ¹⁶² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Further, in the above general formula (16), the anthracene ring and the benzofluorene ring system are bonded to the carbon atom of the 6-membered ring constituting the benzene ring.

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (18).

In the above general formula (18), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁸¹ , and R ¹⁸³ to R ¹⁹⁰ each independently represent R ¹⁰¹ ~ which is not used for bonding with L ¹ in the above general formula (1). R ^{110 is} synonymous.

In the above general formula (18), Ar ¹⁸¹ to Ar ¹⁸² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

In the above general formula (18), the L ¹ system is synonymous with L ¹ in the above general formula (1).

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (19) or the following general formula (20).

In the above general formula (19) or the above general formula (20), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁸¹ , and R ¹⁸³ to R ¹⁹⁰ are each independently represented and are not used in the above general formula (1). R ¹⁰¹ to R ^{110 of the} L ¹ bond are synonymous.

In the above general formula (19) or the above general formula (20), Ar ¹⁸¹ to Ar ¹⁸² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Further, in the above general formula (19), the anthracene ring and the benzofluorene ring system are bonded to the carbon atom of the 6-membered ring constituting the benzene ring.

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (31).

In the above general formula (31), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁸¹ to R ¹⁸⁸ and R ¹⁹⁰ each independently represent R ¹⁰¹ ~ which is not used for bonding with L ¹ in the above general formula (1). R ^{110 is} synonymous.

In the above general formula (31), Ar ¹⁸¹ to Ar ¹⁸² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

In the above general formula (31), the L ¹ system is synonymous with L ¹ in the above general formula (1).

In the present embodiment, the compound represented by the above formula (1) is preferably a compound represented by the following general formula (32) or the following general formula (33).

In the above general formula (32) or the above general formula (33), R ¹⁰¹ to R ¹⁰⁸ , R ¹¹⁰ , R ¹⁸¹ to R ¹⁸⁸ , and R ¹⁹⁰ are each independently represented and are not used in the above general formula (1). R ¹⁰¹ to R ^{110 of the} L ¹ bond are synonymous.

In the above general formula (32) or the above general formula (33), Ar ¹⁸¹ to Ar ¹⁸² each independently represent the same as R ¹¹⁹ to R ¹²⁰ in the above general formula (2).

Further, in the above general formula (32), the anthracene ring and the benzofluorene ring system are bonded to the carbon atom of the 6-membered ring constituting the benzene ring.

R ¹¹⁰ of the above general formulas (4) to (9), (12) to (20), and (31) to (32) is an aromatic hydrocarbon group having 6 to 30 carbon atoms selected from a ring selected from a substituted or unsubstituted ring. It is preferred that the substituted or unsubstituted ring form a base of a heterocyclic group having 5 to 30 atoms.

Further, R ¹¹⁰ of the above general formulae (4) to (9), (12) to (20), and (31) to (32) form a carbon number of 6 to 30 aromatic hydrocarbon group by a substituted or unsubstituted ring. Preferably, a substituted or unsubstituted ring is formed to form a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms.

Next, each substituent described in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33) will be described.

Specific examples of the substituents described in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33) may be mentioned. a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20, a linear chain, a branched chain or Cyclic alkyl, substituted or unsubstituted, linear, branched or cyclic haloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted, linear or branched chain having 1 to 20 carbon atoms shape Or a cyclic alkoxy group, a substituted or unsubstituted, linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms A substituted, unsubstituted ring forms an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, an arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, and a carbon number of 6 to 30. The hydrocarbon group, the substituted or unsubstituted ring forms a heterocyclic group having 5 to 30 atoms.

Examples of the halogen atom in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33) include fluorine and chlorine. , bromine, iodine, etc., with fluorine is better.

The substituted or unsubstituted amine group in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33), The amine group substituted with each substituent is preferably an amine group substituted with an aromatic hydrocarbon group, more preferably an amino group substituted with a phenyl group. The aromatic hydrocarbon group substituted on the amine group may, for example, form an aromatic hydrocarbon group having 6 to 30 carbon atoms.

In the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33), the alkyl groups having 1 to 20 carbon atoms are It may be any of a straight chain, a branched chain or a cyclic group, and an alkyl group of a straight chain or a branched chain may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group or an s- group. Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-fluorenyl, n-fluorenyl, n-undecyl, n- Dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl , 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methyl Pentyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3- Dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl , 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-Bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodine Methyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t- Butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl , 1,3-diaminoisopropyl, 2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2 - cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1, 2,3-Tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 1,2-dinitroethyl 2,3-Dinitro-t-butyl, 1,2,3-trinitropropyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,1,1,3,3 , 3-hexafluoro-2-propyl and the like.

Examples of the cyclic alkyl group (cycloalkyl group) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 4-methylcyclohexyl group, and 3, 5-tetramethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like.

Among the above alkyl groups, an alkyl group having 1 to 10 carbon atoms is preferred, an alkyl group having 1 to 8 carbon atoms is more preferred, and an alkyl group having 1 to 4 carbon atoms is particularly preferred. Among them, methyl, isopropyl, t-butyl and cyclohexyl are preferred.

a linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms The surface may be, for example, one in which the alkyl group having 1 to 20 carbon atoms is substituted with one or more halogen atoms. Specific examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.

In the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33), the linear number of carbon atoms is 1 to 20, A branched or cyclic alkoxy group can be represented by -OY ¹ . Examples of the Y ¹ include the above-mentioned alkyl groups having 1 to 20 carbon atoms. The alkoxy group may, for example, be a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group or a hexyloxy group. Among the above alkoxy groups, an alkoxy group having 1 to 10 carbon atoms is preferred, and an alkoxy group having 1 to 8 carbon atoms is more preferred. Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.

a straight chain, branched chain or cyclic haloalkoxy group having 1 to 20 carbon atoms in the above general formulas (1) to (3), (2-4) to (2-6), and (11) In the above, for example, the alkoxy group having 1 to 20 carbon atoms may be substituted with one or more halogen groups.

The aralkyl group having 7 to 30 carbon atoms in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33) may be used. Expressed as -R ^X -R ^Y . Examples of the R ^X include an alkylene group corresponding to the above alkyl group having 1 to 30 carbon atoms. Examples of the R ^Y include an example in which the following ring forms an aromatic hydrocarbon group having 6 to 30 carbon atoms. In the aralkyl group, the aromatic hydrocarbon group has a carbon number of 6 to 30, preferably 6 to 20, more preferably 6 to 12. Further, in the aralkyl group, the alkyl moiety has a carbon number of from 1 to 30, preferably from 1 to 20, more preferably from 1 to 10, still more preferably from 1 to 6. The aralkyl group may, for example, be benzyl, 2-phenylpropan-2-yl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl or 2-phenyliso Propyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α- Naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl , 1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, M-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o -iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl , p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1 -Hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl.

The ring in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33) forms an aromatic oxygen having a carbon number of 6 to 30. The base can be expressed as -OZ ² . In the case of the Z ² , the following ring forms an aromatic hydrocarbon group having 6 to 30 carbon atoms. As the aryloxy group, for example, a phenoxy group can be mentioned.

The ring in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33) forms an aromatic sulfur having a carbon number of 6 to 30 The base can be expressed as -SZ ³ . In the case of the Z ³ , the following ring forms an aromatic hydrocarbon group having 6 to 30 carbon atoms.

The ring in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), and (31) to (33) forms an aromatic having a carbon number of 6 to 30. Examples of the hydrocarbon group include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, and more specifically, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, and the like. Biphenyl, triphenyl, tetraphenyl, propadienyl fluorenyl, fluorenyl, triphenylene, phenanthryl, anthracenyl, 9,9-dimethylindenyl, benzo[c]phenanthrene Benzo, benzo[a]-tri-phenyl, naphtho[1,2-c]phenanthryl, naphtho[1,2-a]-triphenyl, dibenzo[a,c]-linked Phenyl, benzo[b]propadienyl fluorenyl and the like. Among the above aromatic hydrocarbon groups, an aromatic hydrocarbon group having 6 to 20 carbon atoms and a ring-forming aromatic hydrocarbon group having 6 to 12 carbon atoms are particularly preferable.

The ring in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33) forms a heterocyclic ring having an atomic number of 5 to 30. Examples of the base include a non-condensed hetero ring and a condensed hetero ring, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridyl group, a decyl group, an isodecyl group, a furyl group, a benzofuranyl group, and the like. Isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, oxazolyl, phenanthryl, acridinyl, phenanthryl, thienyl And a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an anthracene ring, a quinoline ring, an acridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine. Ring, piperazine ring, oxazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring a group formed by a benzimidazole ring, a pyran ring, a dibenzofuran ring, or a benzo[c]dibenzofuran ring. Among the above heterocyclic groups, a heterocyclic group having 5 to 20 atomic groups in the ring group and a heterocyclic group having 5 to 12 atoms in the ring are particularly preferable.

In addition to the unsubstituted alkylene group in the above general formulas (1) to (9), (2-4) to (2-6), (11) to (20), (31) to (33) In addition, examples thereof include an alkylalkyl group having 1 to 30 carbon atoms and An arylalkyl group having 6 to 60 carbon atoms.

Examples of the alkyl fluorenyl group having 1 to 30 carbon atoms include a trialkylsulfanyl group having an alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, and specific examples thereof include a trimethyldecyl group. Triethyldecyl, tri-n-butyldecyl, tri-n-octyldecyl, tributyldecyl, dimethylethyldecyl, dimethylisopropyldecyl, dimethyl -n-propyldecyl, dimethyl-n-butyldecyl, dimethyl-t-butyldecyl, diethylisopropylalkyl, vinyl dimethylalkyl, propyl Methyl decyl, tripropyl decyl, and the like. The three alkyl groups may each be the same or different.

The ring may form an arylalkylalkyl group having 6 to 60 carbon atoms, and examples thereof include an arylalkylene group, an alkylarylalkylene group, a dialkylarylalkylene group, a diarylalkylalkyl group, and an alkyldiarylalkyl group. , triaryl decyl group. The plurality of aryl groups may be the same or different from each other or the alkyl groups.

The dialkylarylalkylene group may, for example, be a dialkyl aryl group having two alkyl groups exemplified in the above-mentioned alkyl group having 1 to 20 carbon atoms and having one aryl group having 6 to 30 carbon atoms. Base to alkyl. The carbon number of the dialkylaryl decyl group is preferably from 8 to 30. The two alkyl groups may each be the same or different.

The alkyl diaryl decyl group may, for example, be an alkyl diaryl group having an alkyl group exemplified as an alkyl group having 1 to 20 carbon atoms and having two aryl groups having 6 to 30 carbon atoms. Base to alkyl. The alkyl diaryl decyl group has a carbon number of from 13 to 30. The two aryl groups may each be the same or different.

The triarylsulfanyl group may, for example, be a triarylsulfanyl group having three aryl groups having 6 to 30 carbon atoms in the above ring. The carbon number of the triarylsulfonyl group is preferably from 18 to 30. The three aryl groups may each be the same or different.

Examples of such an arylalkyl group include phenyldimethylalkylalkyl, diphenylmethyldecylalkyl, diphenyl-t-butyldecylalkyl, and triphenylsulfanylalkyl.

In the above general formula (1), R ¹⁰¹ to R ^{110 which} are not bonded to L ¹ are preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

When R ¹⁰⁹ is a ring to form a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms, more preferably 1-naphthyl, 2-naphthyl, 1-indenyl, 2-indenyl, 9-fluorenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-fused tetraphenyl, 2-fused tetraphenyl, 9-fused tetraphenyl, 1-indenyl, 2-indenyl 4-mercapto, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl and 4-methyl-1-indenyl.

In the above general formulas (1), (4), (5), (12), (15), (18), and (31), when L ¹ is a linking group, a substituted or unsubstituted ring may be used to form carbon. The (a+1)-valent aromatic hydrocarbon group having 6 to 30, the substituted or unsubstituted (a+1)-valent ring forming a heterocyclic group having 5 to 10 atomic atoms, or the aromatic hydrocarbon group or the like The ring group bonds 2 to 4 of the formed divalent groups.

Specific examples of the aromatic hydrocarbon group having a (a+1)-valent carbon number of 6 to 30 carbon atoms are exemplified as the (a+1) valence of the aromatic hydrocarbon group having 6 to 30 carbon atoms listed as the above ring. The base.

Further, specific examples of the heterocyclic group having a (a+1)-valent valence of 5 to 30 atoms in the ring include (a+1) which is a heterocyclic group having 5 to 30 atoms in the ring. The base of the price.

When L ¹ is a ring-forming aromatic hydrocarbon group having a carbon number of 6 to 30 (a+1), a more preferable aromatic hydrocarbon group is phenyl, biphenyl, naphthyl, 9,9-di. The methyl fluorenyl group is a divalent group.

When L ¹ is a (he+1)-valent heterocyclic group having a ring number of 6 to 30, a more preferable heterocyclic group is a pyridyl group, a pyrimidinyl group, a dibenzofuranyl group or a carbazolyl group. For the 2 price base.

In the above general formula (2), R ¹¹¹ to R ^{118 which} are not bonded to L ¹ are preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

In the above general formula (2), R ¹¹⁹ to R ¹²⁰ are preferably those having an alkyl group, and more preferably a methyl group and both R ¹¹⁹ and R ¹²⁰ are methyl groups.

In the above general formula (3), in the case of R ¹²¹ to R ¹²⁴ , a hydrogen atom or an alkyl group is preferred, and a hydrogen atom is particularly preferred.

In the above general formula (11), in terms of Ar ¹ , a phenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group or a biphenyl group is particularly preferable.

In the Ra aspect, it is particularly preferable to use a hydrogen atom, an aryl group or a heterocyclic group.

In the present invention, "ring-forming carbon" means a carbon atom constituting a saturated ring, an unsaturated ring or an aromatic ring. The "ring-forming atom" means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

Further, in the present invention, the hydrogen atom means an isotope having a different number of neutrons, that is, a mixture of Protium, Deuterium, and Tritium.

Also, the substituents in the case of "substituted or unsubstituted" The surface may, for example, be an aromatic hydrocarbon group, a heterocyclic group, an alkyl group (linear or branched alkyl group, cycloalkyl group, haloalkyl group), alkoxy group, aryloxy group or aralkyl group as described above. Haloalkoxy, alkylalkylalkyl, dialkylarylalkyl, alkyldiarylalkyl, triarylalkyl, halogen, cyano, hydroxy, nitro, and carboxyl. Other examples include alkenyl or alkynyl groups.

Among the substituents exemplified herein, an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkyl decyl group, an aryl decyl group, a cyano group are preferred, and further, each is substituted. It is preferred that the preferred substituents are preferred in the description.

"Unsubstituted" in the case of "substituted or unsubstituted" means not substituted by the aforementioned substituent, and bonded to a hydrogen atom.

In addition, in the present specification, the "carbon number a to b" in the expression "substituted or unsubstituted carbon number a to b XX group" means that the XX group is a carbon number in the case of no substitution, and the XX group cannot be substituted. The carbon number of the substituent.

In the case of the compound described below or part of its structure, the case of "substituted or unsubstituted" is also the same as described above.

Although specific examples of the anthracene derivatives represented by the general formula (1) are shown below, the invention is not limited to the compounds exemplified herein.

‧Doping materials

As the dopant material used in the organic EL device of the present invention, the alkadiene ruthenium derivative represented by the following general formula (21) can be used.

In the above general formula (21), R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ each independently represent a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a decyl group, a carboxyl group, a substituted or an unsubstituted group. Alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted carbon numbers 7 to 30 The aralkyl group, the substituted or unsubstituted ring forms an aryloxy group having 6 to 30 carbon atoms, and the substituted or unsubstituted ring forms an arylthio group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 50. The alkoxycarbonyl group, the substituted or unsubstituted ring forms an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted ring forming atomic number. The first group of 5 to 30 heterocyclic groups is selected.

In the above general formula (21), the R ²³ system is selected from the second group consisting of the first group of hydrogen-removing atoms represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ . That is, the second group is a hydroxyl group, a cyano group, a nitro group, a decyl group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted ring, an aryloxy group having 6 to 30 carbon atoms, a substitution or The unsubstituted ring forms an arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted ring, and an arylamino group having 6 to 30 carbon atoms. Or an unsubstituted ring forms an aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted ring to form a heterocyclic group having 5 to 30 atoms.

In the above general formula (21), R ²⁴ is a third group consisting of the above-mentioned first group-removed aromatic hydrocarbon group and heterocyclic group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ Selected from the group. That is, the third group consists of a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a decyl group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 20 A cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted ring, and an aryloxy group having 6 to 30 carbon atoms. a substituted or unsubstituted ring which forms an arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, and a substituted or unsubstituted ring to form an aryl group having 6 to 30 carbon atoms. Amine based.

In the above general formula (21), R ²⁷ and R ³² each independently represent a hydrogen atom or a hydroxyl group removed from the first group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ . The fourth group consisting of cyano, nitro, decyl and carboxyl groups is selected. That is, the fourth group consists of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 20 carbon atoms. An oxy group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted ring, an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, and an aromatic sulfur having 6 to 30 carbon atoms. a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted ring, an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, and a carbon number of 6 to 30. The hydrocarbon group and the substituted or unsubstituted ring form a heterocyclic group having 5 to 30 atoms.

Further, in the above general formula (21), R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , and R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring, and in the case where a saturated or unsaturated ring is not formed, the ring is substituted or unsubstituted. .

However, in the above general formula (21), R ²¹ to R ²³ and R ²⁵ to R ³² exclude the case of a monovalent group derived from benzo[k]propadienyl fluorene.

Further, in the above general formula (21), R ²³ is different from R ²⁴ .

Further, in the above general formula (21), any of R ²³ and R ²⁴ is excluded from the α-naphthyl group.

The above R ²⁴ of the general formula (21) is preferably a hydrogen atom.

The substituted or unsubstituted ring of R ²⁷ and R ^{32 in the} above general formula (21) preferably forms an aromatic hydrocarbon group having 6 to 30 carbon atoms. Further, R ²⁷ and R ³² of the above general formula (21) are preferably substituted or unsubstituted phenyl groups.

Or, R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ -based hydrogen atoms of the above general formula (21), and R ²³ , R ²⁷ and R ³² of the above general formula (21) are substituted or The unsubstituted ring is preferably formed by forming an aromatic hydrocarbon group having 6 to 30 carbon atoms.

The hydrogen atoms of R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ in the above general formula (21), and the substituted or unsubstituted ring of R ²⁷ and R ³² of the above general formula (21) form a carbon number. 6 to 30 aromatic hydrocarbon groups, R ²³ -Ar ²¹ -Ar ^{22 of the} above general formula (21), and Ar ²¹ and Ar ²² each independently represent a substituted or unsubstituted ring to form an aromatic having 6 to 30 carbon atoms. Hydrocarbon based is good.

In this case, the Ar ²¹ or the Ar ²² is preferably an aromatic hydrocarbon group having a cyano group as a substituent.

Or, R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ -based hydrogen atoms of the above general formula (21), and R ²⁷ and R ³² of the above general formula (21) are substituted or unsubstituted. The ring forms an aromatic hydrocarbon group having 6 to 30 carbon atoms, R ²³ -Ar ²¹ -Ar ²² -Ar ^{23 of the} above general formula (21), and Ar ²¹ , Ar ²² and Ar ²³ each independently represent a substituted or unsubstituted group. It is preferred that the ring form an aromatic hydrocarbon group having 6 to 30 carbon atoms.

In this case, the Ar ²¹ , the Ar ²² or the Ar ²³ described above is preferably an aromatic hydrocarbon group having a cyano group as a substituent.

Specific examples of the groups listed in the first group to the fourth group selected from R ²¹ to R ^{32 in the} above general formula (21) can be exemplified by the above general formulas (1) to (9). (2-4) ~ (2-6), (11) ~ (20), (31) ~ (33) are illustrated in the description.

Although specific examples of the allene-substituted hydrazine derivative represented by the general formula (21) are shown below, the present invention is not limited to the compounds exemplified above.

The content of the light-emitting layer of the doping material is not particularly limited, and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1% by mass or more and 70% by mass or less, more preferably 1% by mass or more and 30% by mass or less. Doping material When the amount is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration extinction can be avoided.

‧Combination of host material and doping material

In the organic EL device of the present embodiment, an anthracene derivative substituted with an anthracene ring is used as a host material, and an alkadiene fluorene derivative represented by the formula (21) is used as a dopant. When the ruthenium derivative having such a structure is used as the host material, from the planarity of the anthracene ring, it is predicted that the accumulation property between the molecules will rise upward and the charge mobility will become high. At this time, the electric charge leaks from the light-emitting layer, which may cause a decrease in efficiency and life. Therefore, it is considered that by using a dopant having electron or hole trapping property and having a condensed ring structure, the carrier can be enclosed in the light-emitting layer to achieve high efficiency and long life.

The alkadiene oxime derivative is considered to have electron-trapping property and has a condensed ring structure. Therefore, when the host material is used as a dopant material, it is expected to have high efficiency and long life of the organic EL device. .

(hole injection, transport layer)

The hole injection/transport layer is a layer that assists in injecting holes into the light-emitting layer and transporting them to the light-emitting region, and a compound having a large hole mobility and a small ionization energy can be used.

In terms of forming a material for hole injection and transport layer, a material capable of transporting holes to the light-emitting layer at a lower electric field strength is preferable, and for example, an aromatic amine compound is preferably used.

(Electronic injection, transport layer)

The electron injection/transport layer is a layer that assists injection of electrons into the light-emitting layer and transports it to the light-emitting region, and a compound having a large electron mobility can be used.

For the electron injection and the compound to be used in the transport layer, for example, an aromatic heterocyclic compound containing one or more hetero atoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. The nitrogen-containing cyclic derivative is preferably a heterocyclic compound having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton.

In the organic EL device of the present invention, the organic layer other than the light-emitting layer can be used by selecting any compound from among the materials used in the conventional organic EL device, in addition to the above-exemplified compounds.

(substrate)

The organic EL device of the present invention is fabricated on a light-transmissive substrate. The light-transmitting substrate described above is a substrate supporting an organic EL element, and preferably has a light transmittance of 50% or more in a visible region of 400 nm to 700 nm, and is preferably a smooth substrate.

Specifically, a glass plate, a polymer plate, etc. are mentioned.

Examples of the glass plate include those in which sodium carbonate lime glass, glass containing ruthenium, lead glass, aluminum silicate glass, borosilicate glass, borosilicate glass, quartz, or the like is used as a raw material.

Further, examples of the polymer sheet include polycarbonate, acrylate, polyethylene terephthalate, polyether sulfide, and polyfluorene.

(anode and cathode)

The anode of the organic EL element serves as a hole for injecting a hole into the hole injection layer, the hole transport layer or the light-emitting layer, and is effective for a work function of 4.5 eV or more.

Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.

In the anode, these electrode materials are produced by forming a thin film by a vapor deposition method or a sputtering method.

As in the present embodiment, when the light emission from the light-emitting layer is taken out from the anode, it is preferable that the light transmittance of the visible region of the anode is more than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω/□ (ohm/square) or less. The film thickness of the anode is usually selected from the range of 10 nm to 1 μm, preferably 10 nm to 200 nm, depending on the material.

The cathode is preferably a material having a small work function for the purpose of injecting electrons into the electron injecting layer, the electron transporting layer or the light emitting layer.

The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-niobium-lithium alloy, magnesium-silver alloy, or the like can be used.

Similarly to the anode, the cathode can be produced by forming a thin film by a method such as a vapor deposition method or a sputtering method. Further, a state in which light is emitted from the cathode side can be taken. Further, a state in which light emitted from the light-emitting layer is taken out from the cathode side can be employed. When the light from the luminescent layer is taken out from the cathode side, the visible region of the cathode The light transmittance is preferably greater than 10%.

The sheet resistance of the cathode is preferably several hundred Ω / □ or less.

The thickness of the cathode depends on the material, but is usually selected from the range of 10 nm or more and 1 μm or less, preferably 50 nm or more and 200 nm or less.

(Method of forming each layer of an organic EL element)

The method for forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known method of forming a vacuum vapor deposition method, a spin coating method, or the like can be used. The organic layer used in the organic EL device of the present invention may be subjected to a vacuum deposition method, a molecular vapor deposition method (MBE method, MBE: Molecular Beam Epitaxy), or a solution in which the solution is dissolved in a solvent to be impregnated or spin-coated. A coating method such as a method, a casting method, a bar coating method, or a roll coating method is formed by a known method.

(Thickness of each layer of the organic EL element)

The film thickness of the light-emitting layer is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. When the film thickness of the light-emitting layer is 5 nm or more, it is easy to form a light-emitting layer, and it is easy to adjust the chromaticity. On the other hand, when the film thickness of the light-emitting layer is 50 nm or less, the increase in the driving voltage can be suppressed.

The film thickness of each of the other organic layers is not particularly limited, but is usually in the range of several nm to 1 μm. By making such a film thickness range, it is possible to prevent defects such as pinholes caused by excessive film thickness, and to suppress an increase in driving voltage caused by an excessively thick film thickness, and to prevent deterioration of efficiency. .

[Modification of Embodiment]

Further, the present invention is not limited to the above-described embodiments, and modifications, improvements, etc., which are made within the scope of the invention can be included in the present invention.

The light-emitting layer is not limited to one layer, and may be laminated by a plurality of light-emitting layers. When the organic EL device has a plurality of light-emitting layers, at least one of the light-emitting layers may contain a compound represented by the above formula (1) and a compound represented by the above formula (21), and the other light-emitting layer may be a fluorescent light-emitting type. The light emitting layer may also be a light emitting layer of a neon light emitting type.

Further, when the organic EL element has a plurality of light-emitting layers, the light-emitting layers may be provided adjacent to each other, and a plurality of light-emitting units may be laminated through the intermediate layer, in other words, may be a series-connected organic EL element.

In the present invention, it is preferred that the light-emitting layer further contains a charge injection auxiliary material.

When a light-emitting layer is formed using a host material having a wide energy level, the difference between the ionization potential (Ip) of the host material and the Ip of the hole injection, the transport layer, and the like becomes large, and it is difficult to inject into the hole of the light-emitting layer to obtain The drive voltage of sufficient brightness will rise.

In such a case, it is possible to facilitate the injection of holes into the light-emitting layer and reduce the driving voltage by including a hole injection and a charge-injecting auxiliary agent for transporting the light-emitting layer.

As the charge injection auxiliary agent, for example, general hole injection, transportation material, or the like can be used.

Specific examples thereof include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolium derivative, and a phenylenediamine derivative. An arylamine derivative, an amine-substituted chalcone derivative, an oxazole derivative, an anthrone derivative, an anthracene derivative, a stilbene derivative, a decazane derivative, a polydecane-based, an aniline-based copolymer, A conductive polymer oligomer (particularly a thiophene oligomer) or the like.

The material for the hole injecting property is preferably the porphyrin compound, the aromatic tertiary amine compound, and the styrylamine compound, particularly the aromatic tertiary amine compound.

Further, it is possible to exemplify that there are two condensed aromatic rings in the molecule, for example, 4,4'-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter abbreviated as NPD), There may be mentioned 4,4',4"-parado (N-(3-methylphenyl)-N-phenylamino)triphenylamine in which triphenylamine units are linked into three starburst types (hereinafter Referred to as MTDATA).

Further, a hexaazatriazine derivative or the like can also be suitably used as a material for hole injection.

Further, an inorganic compound such as p-type Si or p-type SiC can also be used as a hole injecting material.

The organic EL device of the present invention can be applied to an electronic device such as a display device such as a television, a portable telephone, or a personal computer, or a light-emitting device such as an illumination or a vehicle lamp.

Example

Next, the present invention will be described in more detail by way of examples and comparative examples. However, the present invention is not limited to the contents of the embodiments.

[Synthesis Example of Compound]

(Intermediate Synthesis Example 1) Synthesis of Intermediate 1

The synthetic scheme of Intermediate 1 is shown below.

In the argon atmosphere, the synthesized boric acid A (11.5 g), 4-bromoiodobenzene (11.3 g), and cesium (three) were carried out in the same manner as the method described in Korean Patent Publication No. 10-2009-0117326. A mixture of phenylphosphine)palladium(0) (1.39 g), 2M aqueous sodium carbonate (60 mL) and toluene (120 mL) was stirred at 90 ° C for 8 hours.

The reaction mixture was cooled to room temperature, the reaction solution was extracted with toluene, and the aqueous layer was removed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel chromatography and recrystallization to give Intermediate 1 (8.15 g). The yield was 51%.

(Intermediate Synthesis Example 2) Synthesis of Intermediate 2

The synthetic scheme of Intermediate 2 is shown below.

In the intermediate synthesis example 1, the intermediate 2 was obtained in the same manner as in the intermediate synthesis example 1 except that 3-bromoiodobenzene was used instead of 4-bromoiodobenzene.

(Intermediate Synthesis Example 3) Synthesis of Intermediate 3

The synthetic scheme of Intermediate 3 is shown below.

In the argon atmosphere, the synthesized boric acid B (11.5 g), 4-bromoiodobenzene (11.3 g), and cesium (three) were carried out in the same manner as the method described in Korean Patent Publication No. 10-2009-0117326. A mixture of phenylphosphine)palladium(0) (1.39 g), 2M aqueous sodium carbonate (60 mL) and toluene (120 mL) was stirred at 90 ° C for 8 hours.

The reaction mixture was cooled to room temperature, the reaction solution was extracted with toluene, and the aqueous layer was removed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel chromatography and recrystallization to afford Intermediate 3 (8.79 g). The yield was 55%.

(Intermediate Synthesis Example 4) Synthesis of Intermediate 4

The synthetic scheme of Intermediate 4 is shown below.

In the intermediate synthesis example 3, the intermediate 4 was obtained in the same manner as in the intermediate synthesis example 3 except that 3-bromoiodobenzene was used instead of 4-bromoiodobenzene.

(Intermediate Synthesis Example 5) Synthesis of Intermediate 5

The synthetic scheme of Intermediate 5 is shown below.

In the argon atmosphere, the synthesized boric acid C (11.5 g), 4-bromoiodobenzene (11.3 g), and cesium (three) were carried out in the same manner as the method described in Korean Patent Publication No. 10-2009-0117326. A mixture of phenylphosphine)palladium(0) (1.39 g), 2M aqueous sodium carbonate (60 mL) and toluene (120 mL) was stirred at 90 ° C for 8 hours.

The reaction mixture was cooled to room temperature, the reaction solution was extracted with toluene, and the aqueous layer was removed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated. The resulting residue was chromatographed with cerium oxide colloid Purification by recrystallization gave Intermediate 5 (7.19 g). The yield was 45%.

(Intermediate Synthesis Example 6) Synthesis of Intermediate 6

The synthetic scheme of Intermediate 6 is shown below.

In the intermediate synthesis example 5, the intermediate 6 was obtained in the same manner as in the intermediate synthesis example 5 except that 3-bromoiodobenzene was used instead of 4-bromoiodobenzene.

(Synthesis Example 1) Synthesis of Compound 1

The synthetic scheme of Compound 1 is shown below.

Intermediate 1 (3.99 g) obtained in Intermediate Synthesis Example 1 was obtained under the argon atmosphere, 9-phenylindole-10-ylboronic acid (3.28 g) obtained by a known method, and tris(triphenylphosphine). A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>>

The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue thus obtained was purified by a short-filled ruthenium dioxide colloid chromatography and recrystallization to give Compound 1 (2.80 g). The yield was 49%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 2) Synthesis of Compound 2

The synthetic scheme of Compound 2 is shown below.

In Synthesis Example 1, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 1 was carried out. The operation gave Compound 2. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 3) Synthesis of Compound 3

The synthetic scheme of Compound 3 is shown below.

In Synthesis Example 1, except that 9-(2-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 1 was carried out. The operation gave Compound 3. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 4) Synthesis of Compound 4

The synthetic scheme of Compound 4 is shown below.

In Synthesis Example 1, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 4. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 5) Synthesis of Compound 5

The synthetic scheme of Compound 5 is shown below.

In Synthesis Example 1, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used in place of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 5. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 6) Synthesis of Compound 6

The synthetic scheme of Compound 6 is shown below.

In Synthesis Example 1, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, Compound 6 was obtained in the same manner as in Synthesis Example 1. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 7) Synthesis of Compound 7

The synthetic scheme of Compound 7 is shown below.

In Synthesis Example 1, except that 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, Compound 7 was obtained in the same manner as in Synthesis Example 1. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 8) Synthesis of Compound 8

The synthetic scheme of Compound 8 is shown below.

Intermediate 2 (3.99 g) obtained in Intermediate Synthesis Example 2, 9-phenylindole-10-ylboronic acid (3.28 g) obtained by a known method, hydrazine (triphenylphosphine) under an argon atmosphere. A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>> The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue was purified by short-filled ruthenium dioxide colloidal chromatography and recrystallization to give Compound 8 (2.52 g). The yield was 44%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 9) Synthesis of Compound 9

The synthetic scheme of Compound 9 is shown below.

In Synthesis Example 8, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 8 was carried out. The operation gave Compound 9. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 10) Synthesis of Compound 10

The synthetic scheme of Compound 10 is shown below.

In Synthesis Example 8, except that 9-(2-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 8 was carried out. The operation gave Compound 10. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 11) Synthesis of Compound 11

The synthetic scheme of Compound 11 is shown below.

In Synthesis Example 8, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 11. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 12) Synthesis of Compound 12

The synthetic scheme of Compound 12 is shown below.

In Synthesis Example 8, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 12. The obtained compound was identified by mass spectrometry, for molecular weight 648.28, m/e=648.

(Synthesis Example 13) Synthesis of Compound 13

The synthetic scheme of Compound 13 is shown below.

In Synthesis Example 8, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 8, the compound 13 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 14) Synthesis of Compound 14

The synthetic scheme of Compound 14 is shown below.

In Synthesis Example 8, except that 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, The compound was obtained in the same manner as in Synthesis Example 8. 14. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 15) Synthesis of Compound 15

The synthetic scheme of Compound 15 is shown below.

Intermediate 3 (3.99 g) obtained in Intermediate Synthesis Example 3, 9-phenylindole-10-ylboronic acid (3.28 g) obtained by a known method, hydrazine (triphenylphosphine) under an argon atmosphere. A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>> The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue obtained was purified by short-filled ruthenium dioxide colloidal chromatography and recrystallization to give Compound 15 (3.15 g). The yield was 55%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 16) Synthesis of Compound 16

The synthetic scheme of Compound 16 is shown below.

In Synthesis Example 15, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 15 was carried out. The operation gave Compound 16. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 17) Synthesis of Compound 17

The synthetic scheme of Compound 17 is shown below.

In the synthesis example 15, except that 9-(2-naphthyl)indole-10-ylboronic acid obtained by a known method was used instead of 9-phenylindole-10-ylboronic acid, the same procedure as in Synthesis Example 15 was carried out. The operation gave Compound 17. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 18) Synthesis of Compound 18

The synthetic scheme of Compound 18 is shown below.

In Synthesis Example 15, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 18. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 19) Synthesis of Compound 19

The synthetic scheme of Compound 19 is shown below.

In Synthesis Example 15, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 19. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 20) Synthesis of Compound 20

The synthetic scheme of Compound 20 is shown below.

In Synthesis Example 15, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylfluoren-10-ylboronic acid, In the same manner as in Synthesis Example 15, the compound 20 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 21) Synthesis of Compound 21

The synthetic scheme of Compound 21 is shown below.

In Synthesis Example 15, except that 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used instead of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 15, Compound 21 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 22) Synthesis of Compound 22

The synthetic scheme of Compound 22 is shown below.

Intermediate 4 (3.99 g) obtained in Intermediate Synthesis Example 4, 9-phenylindole-10-ylboronic acid (3.28 g), hydrazine (triphenylphosphine) obtained by a known method under an argon atmosphere. A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>> The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue obtained was purified by short-filled cerium dioxide colloidal chromatography and recrystallization to give Compound 22 (3.21 g). The yield was 56%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 23) Synthesis of Compound 23

The synthetic scheme of Compound 23 is shown below.

In Synthesis Example 22, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 22 was carried out. The operation gave Compound 23. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 24) Synthesis of Compound 24

The synthetic scheme of Compound 24 is shown below.

In Synthesis Example 22, except that 9-(2-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 22 was carried out. The operation gave compound 24. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 25) Synthesis of Compound 25

The synthetic scheme of Compound 25 is shown below.

In Synthesis Example 22, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used in place of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 25. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 26) Synthesis of Compound 26

The synthetic scheme of Compound 26 is shown below.

In Synthesis Example 22, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used in place of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 26. The obtained compound was identified by mass spectrometry, for molecular weight 648.28, m/e=648.

(Synthesis Example 27) Synthesis of Compound 27

The synthetic scheme of Compound 27 is shown below.

In Synthesis Example 22, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 22, Compound 27 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 28) Synthesis of Compound 28

The synthetic scheme of Compound 28 is shown below.

In Synthesis Example 22, in place of 9-phenylindole-10-ylboronic acid, 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used. In the same manner as in Synthesis Example 22, the compound 28 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 29) Synthesis of Compound 29

The synthetic scheme of Compound 29 is shown below.

Intermediate 5 (3.99 g) obtained in Intermediate Synthesis Example 5, 9-phenylindole-10-ylboronic acid (3.28 g), hydrazine (triphenylphosphine) obtained by a known method under an argon atmosphere. A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>> The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue was purified by short-packed cerium dioxide colloidal chromatography and recrystallization to give Compound 29 (2.55 g). The yield was 45%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 30) Synthesis of Compound 30

The synthetic scheme of Compound 30 is shown below.

In Synthesis Example 29, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 29 was carried out. The operation gave Compound 30. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 31) Synthesis of Compound 31

The synthetic scheme of Compound 31 is shown below.

In Synthesis Example 29, except that 9-(2-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 29 was carried out. The operation gave Compound 31. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 32) Synthesis of Compound 32

The synthetic scheme of Compound 32 is shown below.

In Synthesis Example 29, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 32. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 33) Synthesis of Compound 33

The synthetic scheme of Compound 33 is shown below.

In Synthesis Example 29, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 33. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 34) Synthesis of Compound 34

The synthetic scheme of Compound 34 is shown below.

In Synthesis Example 29, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used in place of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 29, Compound 34 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 35) Synthesis of Compound 35

The synthetic scheme of Compound 35 is shown below.

In Synthesis Example 29, except that 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used instead of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 29, Compound 35 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 36) Synthesis of Compound 36

The synthetic scheme of Compound 36 is shown below.

Intermediate 6 (3.99 g) obtained in Intermediate Synthesis Example 6 was obtained under an argon atmosphere, 9-phenylindole-10-ylboronic acid (3.28 g) obtained by a known method, and tris(triphenylphosphine). A mixture of palladium (0) (0.35 g), 2M aqueous sodium carbonate (15 mL), <RTI ID=0.0>> The obtained reaction mixture was cooled to room temperature, water was added and stirred, and the precipitated solid was collected by filtration, and washed with water and methanol. The residue was purified by short-packed cerium dioxide colloidal chromatography and recrystallization to give compound 36 (3.49 g). The yield was 61%. The obtained compound was identified by mass spectrometry, and m/e = 572 for a molecular weight of 572.25.

(Synthesis Example 37) Synthesis of Compound 37

The synthetic scheme of Compound 37 is shown below.

In Synthesis Example 36, except that 9-(1-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 36 was carried out. The operation gave compound 37. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 38) Synthesis of Compound 38

The synthetic scheme of Compound 38 is shown below.

In Synthesis Example 36, except that 9-(2-naphthyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, the same procedure as in Synthesis Example 36 was carried out. The operation gave compound 38. The obtained compound was identified by mass spectrometry, and m/e = 622 for a molecular weight of 622.27.

(Synthesis Example 39) Synthesis of Compound 39

The synthetic scheme of Compound 39 is shown below.

In Synthesis Example 36, except that 9-(3-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used in place of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 39. The obtained compound was identified by mass spectrometry, m/e = 648 for a molecular weight of 648.28.

(Synthesis Example 40) Synthesis of Compound 40

The synthetic scheme of Compound 40 is shown below.

In Synthesis Example 36, except that 9-(4-biphenyl)fluoren-10-ylboronic acid obtained by a known method was used instead of 9-phenylfluoren-10-ylboronic acid, The same operation gave Compound 40. The obtained compound was identified by mass spectrometry, for molecular weight 648.28, m/e=648.

(Synthesis Example 41) Synthesis of Compound 41

The synthetic scheme of Compound 41 is shown below.

In Synthesis Example 36, except that 9-[4-(1-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used instead of 9-phenylindole-10-ylboronic acid, In the same manner as in Synthesis Example 36, Compound 41 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

(Synthesis Example 42) Synthesis of Compound 42

The synthetic scheme of Compound 42 is shown below.

In Synthesis Example 36, in place of 9-phenylindole-10-ylboronic acid, 9-[4-(2-naphthyl)phenyl]indole-10-ylboronic acid obtained by a known method was used. In the same manner as in Synthesis Example 36, the compound 42 was obtained. The obtained compound was identified by mass spectrometry, m/e = 698 for a molecular weight of 698.30.

[Production Example of Organic EL Element]

‧Example 1

A glass substrate (manufactured by GEOMATEC Co., Ltd.) having an ITO transparent electrode of 25 mm × 75 mm × 1.1 mm was placed in isopropyl alcohol and washed with ultrasonic waves for 5 minutes, and then washed by UV ozone for 30 minutes. The thickness of the ITO transparent electrode was made 130 nm.

The glass substrate with the ITO transparent electrode wire after the cleaning is mounted on the substrate holder of the vacuum vapor deposition apparatus, and the following compound is first vapor-deposited by coating the transparent electrode on the surface on the side where the ITO transparent electrode line is formed ( HI-1) was formed into a HI-1 film having a film thickness of 5 nm, and a hole injection layer was formed.

Next, on the HI-1 film, the following compound HT-1, which is a first hole transporting material, was deposited to form an HT-1 film having a thickness of 80 nm, and a first hole transporting layer was formed.

Next, on the HT-1 film, the following compound HT-2 was deposited to form a HT-2 film having a film thickness of 15 nm, and a second hole transport layer was formed.

Further, on the HT-2 film, the compound BH-1 was deposited and formed into a light-emitting layer having a film thickness of 25 nm. At the same time, the following compound BD-1 as a fluorescent material was co-evaporated. The concentration of the compound BD-1 was 5.0% by mass. This co-evaporation film functions as a function of the light-emitting layer.

Then, on the light-emitting layer, the following compound ET-1 is vapor-deposited. The film was an ET-1 film having a film thickness of 25 nm, and a first electron transport layer was formed.

Next, LiF was deposited on the ET-1 film at a deposition rate of 0.1 Å/min to form a LiF film having a thickness of 1 nm, and an electron injecting electrode (cathode) was formed.

Then, metal Al was vapor-deposited on this LiF film to form a metal Al film having a film thickness of 80 nm, and a metal Al cathode was formed.

The compound used in the production of the organic EL device is shown below.

‧Comparative examples 1~3

The organic EL elements of Comparative Examples 1 to 3 except the one in Example 1. The at least one of the host material and the doping material of the optical layer was changed to the compound described in Table 1, and the same procedure as in Example 1 was carried out.

[Evaluation of Organic EL Elements]

With respect to the produced organic EL device, a voltage was applied so that the current density was 10 mA/cm ² , and CIE 1931 chromaticity, current efficiency L/J, external quantum efficiency EQE, main peak wavelength λ _p , and lifetime LT90 were evaluated. The results are shown in Table 2. The evaluation items of the driving voltage, the current efficiency L/J, the external quantum efficiency EQE, and the lifetime LT90 were calculated by comparing the values of the evaluation items of the first embodiment and the comparative examples 1 to 3 with the evaluation items of the comparative example 1. The value of the ratio of values.

‧CIE1931 color

When a voltage was applied to the element and the current density was 10 mA/cm ² , the CIE 1931 chromaticity coordinates (x, y) were measured by a spectroradiometer CS-1000 (manufactured by KONICA MINOLTA Co., Ltd.).

‧current efficiency L/J

When a voltage was applied to the element and the current density was 10 mA/cm ² , the spectroradiance spectrum was measured by the spectroradiometer, and the current efficiency (unit: cd/A) was calculated from the obtained spectroradiance spectrum.

‧External quantum efficiency EQE

From the obtained spectral radiance spectrum, it is assumed that the Lambertian light source has been emitted, and the external quantum efficiency EQE (unit: %) is calculated.

‧Main peak wavelength λ _p

From the obtained spectral radiance spectrum, the main peak wavelength λ _{p is obtained} .

‧Life LT90

A voltage was applied to the element so that the current density became 50 mA/cm ² , and the time (unit: h) until the luminance reached 90% with respect to the initial luminance was measured.

As shown in Table 2, the organic EL device of Example 1 is an organic EL device having high luminous efficiency and long life compared to the organic EL devices of Comparative Examples 1 to 3. For example, the organic EL element of Example 1 is compared to comparison The organic EL device of Example 1 has an external quantum efficiency EQE of about 2.6 times and a lifetime LT90 of about 11 times, and is known to have high luminous efficiency and long life.

Claims (18)

An organic electroluminescence device comprising: an anode; a cathode disposed opposite to the anode; an organic layer provided with at least a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the following general An anthracene derivative represented by the formula (1) and an alkadiene ruthenium derivative represented by the following general formula (21), [In the above general formula (1), any one of R ¹⁰¹ ~ R ¹¹⁰ c is a single bond, a bond to L ^1, is not bonded to L ¹ for the R ¹⁰¹ ~ R ¹¹⁰ each independently represent a selected a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substitution or The unsubstituted ring forms an aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, an arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, and an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring which forms any one of 5 to 30 atomic groups, and L ^{1 is} selected from a single bond or a linking group which forms a carbon from a substituted or unsubstituted ring. The 6 to 30 aromatic hydrocarbon ring structure removes the (a+1)-valent residue formed by (a+1) hydrogen atoms, and the substituted or unsubstituted ring forms a heterocyclic structure of 5 to 30 atoms. a (a+1)-valent residue formed by (a+1) hydrogen atoms or a structure in which at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure is bonded to 2 to 4 (a+1) valence of (a+1) hydrogen atoms removed Residue, and a, b, and c each represent an integer of 1 to 4, and Z ¹ represents a structure represented by the following general formula (2)] [R ¹¹⁹ to R ¹²⁰ in the above general formula (2) each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 30 trioxane An alkyl, substituted or unsubstituted arylalkylene group having 6 to 60 carbon atoms, a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring forming atomic number 5~ Any one of 30 heterocyclic groups, any of R ¹¹¹ to R ¹¹⁸ is a single bond for bonding with L ¹ , and R ¹¹¹ to R ¹¹⁸ not used for bonding with L ¹ are each independently represented. And R ¹⁰¹ to R ^{110 which are} not used for the L ¹ bond, and R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and Among the combinations of R ¹¹⁷ and R ¹¹⁸ , at least one of the two adjacent substituents has a ring structure represented by the following general formula (3)] [In the above general formula (3), y ¹ and y ² represent the bonding positions of the adjacent groups of R ¹¹¹ to R ¹¹⁸ of the above general formula (2), and R ¹²¹ to R ¹²⁴ each independently represent a hydrogen atom selected from hydrogen atoms. , halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted The ring forms an aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, an arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substitution. Or the unsubstituted ring forms any one of 5 to 30 heterocyclic groups, and in the above general formula (2), any of R ¹¹¹ to R ¹¹⁸ which does not form a ring, and R of the above general formula (3) Any one of ¹²¹ to R ¹²⁴ is a single bond, and is used to bond with the general formula (1) L ¹ ] [In the above general formula (21), R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ each independently represent a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a decyl group, a carboxyl group, a substitution or no Substituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number 6~ 20 arylalkyl, substituted or unsubstituted ring to form an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form an arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number of 2 to 30 The alkoxycarbonyl group, the substituted or unsubstituted ring forms an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted ring-forming atom. The first group selected from the group consisting of 5 to 30 heterocyclic groups, R ²³ is a hydrogen atom removed by the first group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ Among the second group of the constituents, R ²⁴ is the third group consisting of the above-mentioned first group-removed aromatic hydrocarbon group and heterocyclic group represented by R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ²⁸ to R ³¹ . those selected from the group, R ²⁷ and R ³² are each independently It is represented by ^21, the fourth group of R ^22, R ^25, R ²⁶ and R ²⁸ ~ R shown in the first group ³¹ of the removal of a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl silicon and a carboxyl group composed of R Selected, in addition, R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ and R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring, and in the case where a saturated or unsaturated ring is not formed, the ring is substituted or unsubstituted, R ²¹ to R ²³ and R ²⁵ to R ³² are excluded from the monovalent group derived from benzo[k]propadienyl, R ²³ is different from R ²⁴ , and any of R ²³ and R ²⁴ is excluded as The case of α-naphthyl]. The organic electroluminescence device according to claim 1, wherein Z ¹ in the above general formula (1) is any ^one of the following general formulas (2-4), (2-5), and (2-6). Show, [Ar ¹⁶¹ to Ar ¹⁶² in the above general formula (2-4), Ar ¹⁷¹ to Ar ¹⁷² in the above general formula (2-5), and Ar ¹⁸¹ to Ar ¹⁸² in the above general formula (2-6) are independent of each other. The ground representation is synonymous with R ¹¹⁹ to R ¹²⁰ in the above general formula (2), and any one of R ¹⁶¹ to R ¹⁷⁰ in the above general formula (2-4) is a single bond for bonding with L ¹ , and ¹⁷⁰ is not used to represent each independently bonded to L ¹ of R ¹⁶¹ ~ R ¹¹⁰ is not used, and is synonymous bonded to L ¹ of R ¹⁰¹ ~ R, in the foregoing general formula (2-5) R ¹⁷¹ ~ R ¹⁸⁰ in any system in a single bond to bond to L ^1, and not to be bonded to L ¹ of R ¹⁷¹ ~ R ¹⁸⁰ and each independently represents a non-bonded to L ¹ of R ¹⁰¹ ~ R ¹¹⁰ Synonymously, any one of R ¹⁸¹ to R ¹⁹⁰ in the above general formula (2-6) has a single bond for bonding with L ¹ and is not used for R ^{1 181} to R ¹⁹⁰ bonded to L ¹ independently. and ¹¹⁰ represents a non-synonymous bonded to L ¹ of R ¹⁰¹ ~ R]. The organic electroluminescence device according to claim 1, wherein b of the above general formula (1) is 1. The organic electroluminescence device of claim 1, wherein the a of the general formula (1) is 1 or 2. The organic electroluminescence device according to claim 1, wherein at least one of R ¹⁰⁹ and R ¹¹⁰ of the above general formula (1) is used for a single bond bonded to L ¹ . The organic electroluminescence device according to claim 1, wherein at least one of R ¹⁰¹ to R ¹⁰⁴ of the above general formula (1) is used for a single bond bonded to L ¹ . The organic electroluminescence device according to claim 6, wherein R ¹⁰² of the above general formula (1) is used for a single bond bonded to L ¹ . The organic electroluminescence device according to claim 1, wherein the R ¹⁰⁹ of the above general formula (1) is formed by a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted ring. The selected one of the heterocyclic groups having 5 to 30 atoms. The organic electroluminescence device according to claim 8, wherein R ¹⁰⁹ of the above general formula (1) is represented by the following general formula (11), [In the above general formula (11), Ar ¹ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms formed by a substituted or unsubstituted ring, or a heterocyclic group having 5 to 30 atoms in the form of a substituted or unsubstituted ring. The Ra system is synonymous with R ¹⁰¹ ~ R ¹¹⁰ which is not used for L ¹ bonding in the above general formula (1), d represents an integer of 1 to 4, and when d is 2 to 4, the complex Ra may be the same. Or different]. The organic electroluminescence device according to claim 8, wherein the R ^109- substituted or unsubstituted ring of the above general formula (1) forms a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms. The organic electroluminescence device according to any one of the preceding claims, wherein the R ²⁴ hydrogen atom of the general formula (21). The organic electroluminescence device according to any one of claims 1 to 3, wherein the substituted or unsubstituted ring of R ²⁷ and R ³² of the general formula (21) forms an aromatic hydrocarbon group having 6 to 30 carbon atoms. . The organic electroluminescence device according to claim 12, wherein R ²⁷ and R ³² of the above general formula (21) are substituted or unsubstituted phenyl groups. The organic electroluminescence device according to any one of claims 1 to 3, wherein R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ of the general formula (21) are hydrogen atoms, the aforementioned The substituted or unsubstituted ring of R ²³ , R ²⁷ and R ³² of the general formula (21) forms an aromatic hydrocarbon group having 6 to 30 carbon atoms. The organic electroluminescence device according to any one of claims 1 to 3, wherein R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ of the general formula (21) are hydrogen atoms, the aforementioned The R ²⁷ and R ³² substituted or unsubstituted rings of the general formula (21) form an aromatic hydrocarbon group having 6 to 30 carbon atoms, and the R ²³ -Ar ²¹ -Ar ²² , Ar ²¹ and Ar of the above general formula (21) ²² each independently represents a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms. The organic electroluminescence device according to any one of claims 1 to 3, wherein R ²¹ to R ²² , R ²⁴ to R ²⁶ and R ²⁸ to R ³¹ of the general formula (21) are hydrogen atoms, the aforementioned The R ²⁷ and R ³² substituted or unsubstituted rings of the general formula (21) form an aromatic hydrocarbon group having 6 to 30 carbon atoms, and the above-mentioned general formula (21) R ²³ -Ar ²¹ -Ar ²² -Ar ²³ ,Ar ²¹ , Ar ²² and Ar ²³ each independently represent a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms. The organic electroluminescence device according to claim 15, wherein the Ar ²¹ or the Ar ²² is an aromatic hydrocarbon group having a cyano group as a substituent. The organic electroluminescence device according to claim 16, wherein the Ar ²¹ , the Ar ²² or the Ar ²³ is an aromatic hydrocarbon group having a cyano group as a substituent.