KR20220142919A - Compound, Organic EL Device and Display Device - Google Patents

Abstract

According to the present invention, a compound applicable to an electron transport layer or a hole blocking layer of an organic electroluminescent device, the organic electroluminescent device using such a compound, and a display apparatus including the organic electroluminescent device are provided. In particular, when the novel compound represented by chemical formula 1 of the present invention is used as a material for the electron transport layer and/or the hole blocking layer, a full color display panel with greatly improved performance and lifespan can be manufactured.

Description

Compound, Organic EL Device and Display Device

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device, an organic electroluminescent device including the same, and a display device.

Recently, as a full-color flat panel display, a display using an organic electroluminescent element is attracting attention, and is used in display devices such as smartphones, TVs, automobiles, and VR (Virtual Reality) head mounted devices.

An organic electroluminescent element has a structure which consists of a pair of electrodes which consist of an anode and a cathode, and one layer or a plurality of layers disposed between the pair of electrodes and containing an organic compound. The layer containing the organic compound includes a light emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

In order to further broaden the field of application of displays using organic electroluminescent elements, reduction of power consumption of elements (lower voltage and improvement of external quantum efficiency) and longer lifespan are required.

In particular, lower power consumption and longer lifespan of blue light emitting devices are required, and for this purpose, various materials for electron transport/injection layers are being studied.

For example, as described in Patent Document 1, it is known that an organic EL device can be driven at a low voltage by using a pyridine derivative or a bipyridine derivative as a material for an electron transport/injection layer.

Further, studies have been made to use benzimidazole or benzothiazole derivatives as materials for electron transport/injection layers in organic electroluminescent devices (see Patent Documents 2 to 4).

As another conventional material for an electron transport/injection layer, a pyrimidine derivative and a triazine derivative are also known (Patent Document 5).

However, in the case of such a conventional electron transport/injection layer material, further improvement is required in terms of luminous efficiency, driving voltage, and lifetime.

In addition, in the conventional organic electroluminescent device, excitons and/or holes generated in the light emitting layer diffuse into the electron transport layer and emit light at the interface with the electron transport layer, resulting in reduced luminous efficiency and reduced lifetime.

Japanese Patent Laid-Open No. 2003-123983 US Patent Publication 2003/215667 International Publication 2003/060956 International Publication 2008/117976 Registered Patent Publication No. 2084906

The present invention provides a compound that has high stability and high electron mobility with respect to electrons, and can suppress the diffusion of excitons and/or holes into the electron transport layer. An object of the present invention is to provide an organic electroluminescent device and a display device using the same.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X ₁ and X ₂ are the same or different from each other, and are each independently selected from the group consisting of a direct bond, CR _a R _b , O, S or NR _c , and both X ₁ and X ₂ are not a direct bond,

R ₁ to R ₄ , R _a to R _c are the same as or different from each other, and each independently hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group , substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ - C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or Unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ selected from the group consisting of an arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring,

m, n, o and p are integers from 0 to 4,

L ₁ is a direct bond, a substituted or unsubstituted C ₃ -C ₃₀ arylene group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group is selected from the group consisting of,

A is represented by the following [Formula 2],

[Formula 2]

Y ₁ To Y ₁₀ Are the same as or different from each other, each independently N or CR _d , Y ₁ To Y ₁₀ At least one of N,

one of R _d of CR _d is bonded to L ₁ ,

R _d is hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted a C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₂₀ hetero Alkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ arylsilyl group, and substituted or unsubstituted C ₃ -C ₃₀ is selected from the group consisting of a heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring.

In addition, the present invention provides an organic electroluminescent device including the compound represented by Formula 1 in an organic material layer, and a display device including the organic electroluminescent device.

In particular, when the novel compound represented by Formula 1 of the present invention is used as a material for an electron transport layer and/or a hole blocking layer, an organic electroluminescent device having superior light emitting performance, low driving voltage, high efficiency and long lifespan compared to conventional materials In addition, it is possible to manufacture a full-color display panel with greatly improved performance and lifespan.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

<Description of the compound of the present invention>

The compound according to the present invention is a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X ₁ and X ₂ are the same or different from each other, and are each independently selected from the group consisting of a direct bond, CR _a R _b , O, S or NR _c , and both X ₁ and X ₂ are not a direct bond,

R ₁ to R ₄ , R _a to R _c are the same as or different from each other, and each independently hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group , substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ - C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or Unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ selected from the group consisting of an arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring,

m, n, o and p are integers from 0 to 4,

L ₁ is a direct bond, a substituted or unsubstituted C ₃ -C ₃₀ arylene group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group is selected from the group consisting of,

A is represented by the following [Formula 2],

[Formula 2]

Y ₁ To Y ₁₀ Are the same as or different from each other, each independently N or CR _d , Y ₁ To Y ₁₀ At least one of N,

one of R _d of CR _d is bonded to L ₁ ,

R _d is hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted a C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₂₀ hetero Alkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ arylsilyl group, and substituted or unsubstituted C ₃ -C ₃₀ is selected from the group consisting of a heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring.

Hereinafter, the substituent in this invention is demonstrated in detail.

A position to which a substituent is not bonded to the compound described herein may be hydrogen or deuterium may be bonded.

As used herein, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent is substitutable, 2 In the case of more than one substitution, two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; cyano group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; and substituted or unsubstituted by one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted in which two or more substituents among the exemplified substituents are connected. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BR _a R _b , wherein R _a and R _b are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group is an alkynyl group having 2 to 20 carbon atoms, and more preferably, the alkynyl group is an unsaturated aliphatic hydrocarbyl group including a triple bond such as an ethynyl group, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and 9-methyl-anthracenylamine. group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, and the like, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the aryl amine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenyl amine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group, but is not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the aryl heteroarylamine group refers to an amine group substituted with an aryl group and a heterocyclic group.

In the present specification, examples of the aryl phosphine group include a substituted or unsubstituted monoaryl phosphine group, a substituted or unsubstituted diaryl phosphine group, or a substituted or unsubstituted triaryl phosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

spirofluorenyl groups such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

,

,

등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but it is preferably from 1 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 1 to 30 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyran group, thiopyran group, pyrazine group, oxazine group, thiazine group, dioxine group, triazine group, tetrazine group, quinoline group, isoquinoline group, Quinazoline group, quinoxaline group, naphthyridine group, acridine group, xanthene group, phenanthridine group, diazanaphthalene group, triazaindene group, indole group, indoline group, indolizine group, phthalazine group, pyridopyrimi Dean group, pyridopyrazine group, pyrazino pyrazine group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, dibenzosilol group, Carbazole group, benzocarbazole group, dibenzocarbazole group, indolocarbazole group, indenocarbazole group, phenazine group, imidazopyridine group, phenoxazine group, phenanthridine group, phenanthroline group, phenothiazine ) group, an imidazopyridine group, and an imidazophenanthridine group. a benzimidazoquinazoline group, or a benzimidazophenanthridine group;

,

,

and the like, but are not limited thereto.

In the present specification, the nitrogen-containing heterocyclic group is a heterocyclic group including at least one nitrogen atom as a ring member, and the number of atoms constituting the ring may be 5, 6, or 7 or more.

Specifically, examples of the monocyclic nitrogen-containing heterocyclic group include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a pyrazole group, an oxazole group, a thiazole group, a triazole group, an oxadiazole group, and a thiadiazole group. there is In addition, examples of the polycyclic nitrogen-containing heterocyclic group include a benzimidazole group, a benzoxazole group, a benzothiazole group, a phenazinyl group, a phenoxazine group, a phenanthridine group, a phenanthroline group, a phenothiazine group, an imidazopyridine group, and an imidazophenanthridine group, a benzimidazoquinazoline group, and a benzimidazophenanthridine group.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, and arylheteroarylamine group is described above. The description of one aryl group may apply.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group among the alkylthioxy group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group, and the alkylamine group.

In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group among the heteroaryl group, the heteroarylamine group, and the arylheteroarylamine group is aromatic.

In the present specification, the description of the above-described alkenyl group may be applied to the alkenyl group among the aralkenyl groups.

In the present specification, the description of the above-described aryl group may be applied except that the arylene group is a divalent group.

In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene group is a divalent group of the aromatic heterocyclic group.

In the present specification, "adjacent group" refers to a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted at the atom in which the substituent is substituted. can mean For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent groups".

In the present specification, a ring formed by bonding adjacent groups to each other may be monocyclic or polycyclic, and may be a condensed ring of aliphatic, aromatic or aliphatic and aromatic, and may form a hydrocarbon ring.

In one embodiment of the present invention, at least two of Y ₁ to Y ₁₀ are N.

In one embodiment of the present invention, A has the following structure.

As such, the compound of the present invention includes a benzoquinazoline group having higher electron mobility than a triazine group or a pyrimidine group, which is an electron withdrawing or electron accepting group of a conventional electron transport material, thereby improving driving voltage and efficiency effect can be obtained.

In one embodiment of the present invention, X ₂ is a direct bond.

In one embodiment of the present invention, X ₁ is O.

In one embodiment of the present invention, X ₁ is a direct bond.

In one embodiment of the present invention, L ₁ is a direct bond.

In one embodiment of the present invention, L1 is a substituted or unsubstituted C ₃ -C ₃₀ arylene group. The compound of the present invention introducing a linker of an arylene group can implement the characteristics of the hole blocking layer that prevents the passing of holes to the electron transport layer as well as the electron transport layer.

In one embodiment of the present invention, the compound of Formula 1 is any one of the following compounds.

Hereinafter, an organic electroluminescent device according to an embodiment of the present invention will be described in detail with reference to the drawings. 1 is a schematic cross-sectional view showing an organic electroluminescent device according to an embodiment of the present invention.

<Organic electroluminescent device>

The organic electroluminescent device 1 shown in FIG. 1 includes an anode 110 (first electrode) provided on a substrate 100 , a hole injection layer 120 provided on the anode 110 , and a hole injection layer 120 . ) provided on the hole transport layer 130 , the light emitting layer 140 provided on the hole transport layer 130 , the electron transport layer 150 provided on the light emitting layer 140 , and the electron injection layer provided on the electron transport layer 150 . 160 and a cathode 170 (second electrode) provided on the electron injection layer 160 . Here, the layers between the anode 110 and the cathode 170 constitute an organic material layer.

In addition, the organic electroluminescent element 1 has a laminated structure reversed (so-called inverted element), for example, a cathode provided on the substrate 100, an electron injection layer provided on the cathode, and an electron injection layer on An electron transport layer provided on the , a light emitting layer provided on the electron transport layer, a hole transport layer provided on the light emitting layer, a hole injection layer provided on the hole transport layer, and an anode provided on the hole injection layer may be configured.

In the organic electroluminescent device of the present invention, all of the above layers are not essential, and the minimum structural unit is composed of an anode 110 , a light emitting layer 140 , and a cathode 170 , and a hole injection layer 120 , a hole At least one of the transport layer 130 , the electron transport layer 150 , and the electron injection layer 160 may be omitted.

For example, in addition to the configuration of "anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode" described above for the laminate structure of the organic electroluminescent element, "anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer/cathode", "anode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/cathode", "anode/hole injection layer/hole transport layer/light emitting layer/electron injection layer/cathode", "anode/hole injection layer/ "Hole transport layer / light emitting layer / electron transport layer / cathode", "anode / light emitting layer / electron transport layer / electron injection layer / cathode", "anode / hole transport layer / light emitting layer / electron injection layer / cathode", "anode / hole transport layer / light emitting layer / electrons Transport layer/cathode”, “Anode/hole injection layer/light-emitting layer/electron injection layer/cathode”, “anode/hole injection layer/light-emitting layer/electron transport layer/cathode”, “anode/light-emitting layer/electron transport layer/cathode”, “anode/ light emitting layer/electron injection layer/cathode".

In addition, for the purpose of adjusting the balance of the concentrations of holes and electrons in the light emitting layer 140 , the region (hole transport region) between the anode 110 and the light emitting layer 140 and between the light emitting layer 140 and the cathode 170 . A separate layer (eg, a hole blocking layer and/or an electron blocking layer, etc.) may be added to the region (electron transport region) of .

In this case, the organic electroluminescent device 1 is "anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode", "anode / hole injection layer / hole transport layer / light emitting layer / It can have a stacked structure such as hole blocking layer/electron transport layer/electron injection layer/cathode”, “anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode” have.

In addition, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

Hereinafter, each layer constituting the substrate 10 and the organic EL device 1 used for manufacturing the organic EL device 1 will be described in detail.

The substrate 100 is a support for supporting the organic electroluminescent device 1 , and usually glass, metal, polymer, semiconductor (silicon), or the like is used. The substrate 100 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, metal foil, a polymer film, a polymer sheet, or the like is used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate and polysulfone are preferable. In the case of manufacturing a flexible display, as the substrate 100 , a polymer material having high thermal stability and flexibility (eg, polyimide) coated on a glass plate (also referred to as carrier glass) may be used.

If it is a glass substrate, soda-lime glass, an alkali free glass, etc. are used, and since thickness also needs just to have sufficient thickness to maintain mechanical strength, what is necessary is just 0.2 mm or more, for example. As an upper limit of thickness, it is 2 mm or less, for example, Preferably it is 1 mm or less. As for the material of the glass, since it is preferable that there are few ions eluted from the glass, an alkali _- free glass is preferable. In addition, in order to improve gas barrier properties, a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate 100. In particular, when a polymer plate, film or sheet having low gas barrier properties is used as the substrate 100 , It is preferable to provide a gas barrier film.

The anode 110 is an electrode for injecting holes, and the anode material is preferably a material having a large work function so that holes can be smoothly injected into the organic material layer.

Examples of the material for forming the anode 110 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, vanadium, copper, zinc, etc.) or alloys thereof, metal oxides (indium oxide, tin oxide, indium-tin oxide ( ITO), indium-zinc oxide (IZO), etc.), ZnO:Al or _SNO2 : a combination of metal and oxide such as Sb, metal halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass or nesa glass, etc. can Examples of the organic compound include polythiophene such as poly(3-methylthiophene) and poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, etc. A conductive polymer etc. are mentioned. In addition, it can select and use suitably from the material used as an anode of an organic electroluminescent element.

The hole injection layer 120 serves to efficiently inject holes moving from the anode 110 into the light emitting layer 140 or the hole transport layer 130 . The hole transport layer 130 serves to efficiently transport holes injected from the anode 110 or holes injected from the anode 110 through the hole injection layer 120 to the emission layer 140 . The hole injection layer 120 and the hole transport layer 130 are formed by laminating and mixing one or more types of hole injection and transport materials, respectively, or a mixture of a hole injection and transport material and a polymer binder. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

As the hole injection/transport material, it is preferable that the hole injection efficiency is high and the injected hole is efficiently transported. For this purpose, it is preferable that the ionization potential is small, the hole mobility is large, the stability is excellent, and it is a material that is difficult to generate trap impurities during manufacture and use.

As a material for forming the hole injection layer 120 and the hole transport layer 130, a compound conventionally used as a charge transport material for holes in a photoconductive material, a p-type semiconductor, a hole injection layer of an organic electroluminescent device, and Any compound can be selected and used from the well-known compounds used for a hole transport layer.

These specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) biscarbazole derivatives, and triarylamine derivatives. (Polymer having aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3- methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N, N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl- 1,1'-diamine, N ⁴ ,N ^{4 '} -diphenyl-N ⁴ ,N ^{4 '} -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]- 4,4'-diamine, N ⁴ ,N ⁴ ,N ^{4 '} ,N 4'-tetra ^[ 1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4 Triphenylamine derivatives such as '-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene) -2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate having the above-mentioned monomers in the side chain, styrene derivatives, polyvinylcarps, etc. Bazole, polysilane, etc. are preferable, but if it is a compound which can form the thin film required for manufacture of a light emitting element, can inject a hole from an anode, and can also transport a hole, it will not specifically limit.

Moreover, it is also known that the electroconductivity of an organic semiconductor is strongly influenced by the doping. Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a good electron accepting compound. For doping of the electron donor material, a strong electron acceptor such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) is used. known (eg, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998) and J. Blochwitz , M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron-donating type base material (hole-transporting material). Depending on the number and mobility of holes, the conductivity of the base material changes significantly. As a matrix material having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc) etc.) are known (Japanese Patent Laid-Open 2005) -167175 publication).

An additional hole buffer layer may be provided between the hole injection layer 120 and the hole transport layer 130 , and may include hole injection or transport materials known in the art.

The light emitting layer 140 is a layer that emits light by recombination of holes injected from the anode 110 and electrons injected from the cathode 170 between electrodes to which an electric field is applied. The material for forming the light emitting layer 140 may be a compound that emits light by being excited by recombination of holes and electrons (a light emitting compound), and a stable thin film shape can be formed, and strong light emission (fluorescence) efficiency in a solid state It is preferable that it is a visible compound.

The light emitting mechanism of the light emitting layer 140 is divided into fluorescence and phosphorescence. Fluorescence is a mechanism in which excitons in a singlet state come down to the ground state among excitons generated by the combination of holes and electrons and emit light while phosphorescence is a mechanism in which excitons in a triplet state emit light as they descend to the ground state. 25% of singlet excitons and 75% of triplet excitons are generated by the combination of holes and electrons. Unlike fluorescence, where only 25% of singlet excitons contribute to light emission, in phosphorescence, 75% of triplet excitons and Since 25% of singlet excitons that can be converted to triplet excitons through intercalation all contribute to light emission, it is theoretically possible to realize 100% internal quantum efficiency.

The light emitting layer 140 may be a single layer or a plurality of layers, and may include a host and a dopant to improve color purity and quantum efficiency. In the light emitting layer 140 having such a structure, excitons generated in the host are transferred to the dopant to emit light. The number of host material and the dopant material may be one, respectively, or a plurality of combinations may be sufficient as them. The dopant material may be contained in the whole host material, or may be contained partially. As a doping method, although it can form by the co-evaporation method with a host material, you may vapor-deposit simultaneously after pre-mixing with a host material, or you may form into a film by the wet film-forming method after pre-mixing with a host material with an organic solvent.

The usage-amount of a host material changes with the kind of host material, and what is necessary is just to set it according to the characteristic of the host material. The standard of the usage-amount of a host material becomes like this. Preferably it is 50-99.999 weight% of the whole material for light emitting layer, More preferably, it is 80-99.95 weight%, More preferably, it is 90-99.9 weight%.

The usage-amount of a dopant material changes with the kind of dopant material, and what is necessary is just to set it according to the characteristic of the dopant material. The standard of the usage-amount of dopant material becomes like this. Preferably it is 0.001 to 50 weight% of the whole material for light emitting layer, More preferably, it is 0.05 to 20 weight%, More preferably, it is 0.1 to 10 weight%. If it is the said range, it is preferable at the point which can prevent the density-quenching phenomenon, for example.

Examples of the host material include a condensed aromatic ring derivative or a compound containing a heterocyclic ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) , a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the dopant. , but is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant is a phosphor such as (4,6-F2ppy)2Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), or PFO. A fluorescent material such as a polymer-based polymer or a PPV-based polymer may be used, but is not limited thereto.

For example, as the blue light emitting dopant, a polyaromatic compound represented by the following formula (BD-YX2) or a multimer of a polyaromatic compound having a plurality of structures represented by the following formula (BD-YX2) may be used.

In the formula (BD-YX2), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;

Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl;

X1 and X2 are each independently >O, >NR, >C(-R) ₂ , >S or >Se, wherein R of >NR is optionally substituted aryl, optionally substituted heteroaryl, or substituted optionally alkyl or optionally substituted cycloalkyl;

and R in >C(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >NR and >C(-R) At least one of R of ₂ may be bonded to at least one of the A ring, the B ring and the C ring by a linking group or a single bond,

At least one hydrogen in the compound or structure represented by the formula (BD-YX2) may be substituted with deuterium, cyano or halogen,

In the compound or structure represented by the formula (BD-YX2), at least one of ring A, ring B, ring C, aryl and heteroaryl may be condensed with at least one cycloalkane, At least one hydrogen may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

In particular, the aryl ring or heteroaryl ring as ring A, ring B and ring C in the formula (BD-YX2) is a 5-membered ring or It is preferable that it is a 6-membered ring.

The electron injection layer 160 serves to efficiently inject electrons moving from the cathode 170 into the emission layer 140 or the electron transport layer 150 .

The electron transport layer 150 serves to efficiently transport electrons injected from the cathode 170 or electrons injected from the cathode 170 through the electron injection layer 160 to the emission layer 140 . As the material of the electron transport layer 150, a compound having electron accepting properties and high electron mobility is suitable. In addition, it must have a lowest unoccupied molecular orbital (LUMO) energy level suitable for injecting electrons into the emission layer 140 , and the HOMO of the emission layer 140 in order to prevent holes from passing from the emission layer 140 to the electron transport layer 150 . (Highest Occupied Molecular Orbital) It is preferable that the difference from the energy level is large.

The electron transport layer 150 and the electron injection layer 160 are each formed by laminating and mixing one or two or more types of electron transporting/injecting materials.

The electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting electrons, and it is preferable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferable that the material is a material having high electron affinity, high electron mobility, excellent stability, and difficult to generate trap impurities during manufacture and use. The electron injection/transport layer in this embodiment may have the function of the layer which can block|block the movement of a hole efficiently. As a material for forming the electron transport layer 150 or the electron injection layer 160, a compound conventionally used as an electron transport compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic electroluminescent device. It can be used arbitrarily selected from among the compounds. In the present invention, as the electron transport material and/or the electron injection material, the compound represented by the formula (1) can be used.

Generally, as a material used for an electron transport layer or an electron injection layer, a compound consisting of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, a pyrrole derivative, and a condensation thereof It is preferable to contain at least 1 sort(s) chosen from a ring derivative and the metal complex which has electron-accepting nitrogen. Specifically, condensed ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives , quinone derivatives such as anthraquinone and diphenoquinone, phosphate derivatives, carbazole derivatives, and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex, and benzoquinoline metal complex. Although these materials are used individually, you may mix and use with other materials.

Further, as specific examples of other electron transport compounds, pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinones Derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N- naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles Compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives , oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene, etc.), naphthyridine derivatives ( bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphoroxide derivatives, bisstyryl derivatives, etc. can be heard

A metal complex having electron-accepting nitrogen can also be used. For example, a hydroxyazole complex such as a quinolinol-based metal complex or a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, or a flavonol metal complex. and a benzoquinoline metal complex.

Although the above-mentioned materials are used individually, you may use it in mixture with other materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, Phenanthroline derivatives and quinolinol-based metal complexes are preferred.

The electron transport layer or the electron injection layer may further contain a material capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances are used as long as they have a certain reducing property, for example, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metals. At least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes can be preferably used.

Preferred reducing substances include alkali metals such as Li (work function 2.3 eV), Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV) or Cs (work function 1.95 eV); alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 to 2.5 eV) or Ba (work function 2.52 eV) are exemplified, and those having a work function of 2.9 eV or less are particularly preferable. Among these, a more preferable reducing substance is an alkali metal of K, Rb, or Cs, More preferably, it is Rb or Cs, Most preferably, it is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to a material for forming the electron transport layer or the electron injection layer, the luminance of light emission in the organic EL device and the lifespan of the alkali metal can be improved. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and A combination of Na and K is preferred. By containing Cs, the reducing ability can be exhibited efficiently, and the improvement of the light emission luminance in an organic electroluminescent element and life extension are attained by addition to the material which forms an electron transport layer or an electron injection layer.

The cathode 170 serves to inject electrons into the emission layer 140 through the electron injection layer 160 and the electron transport layer 150 .

The material for forming the cathode 170 is preferably a material having a small work function so that electrons can be efficiently injected into the organic material layer. Specific examples of the negative electrode material include metals such as tin, indium, calcium, aluminum, silver, lithium, sodium, potassium, titanium, yttrium, gadolinium, lead, cesium and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy). , an aluminum-lithium alloy such as lithium fluoride/aluminum, etc.) are preferable. In order to increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, these low work function metals are generally unstable in the atmosphere in many cases. In order to improve this point, for example, a method of using an electrode with high stability by doping a trace amount of lithium, cesium, or magnesium into an organic material layer is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

The organic material layer may further include an electron blocking layer between the hole transport layer 130 and the emission layer 140 , and may further include a hole blocking layer between the electron transport layer 150 and the emission layer 140 .

In the electron blocking layer and the hole blocking layer, excitons generated in the light emitting layer 140 diffuse into the electron transport layer 150 or the hole transport layer 130 adjacent to the light emitting layer 140, or do not recombine in the light emitting layer 140. The hole transport layer ( 130) or the electron transport layer 150 is a layer that prevents electrons or holes from passing over. Due to this, the number of excitons contributing to light emission in the light emitting layer is increased, so that the light emission efficiency of the device can be improved and the driving voltage can be lowered. In addition, by preventing an irreversible decomposition reaction due to oxidation by diffusion of holes into the electron transport layer 150 that moves electrons by reduction (electron acceptor), the durability and stability of the device are improved and the lifespan of the device is effectively increased can be increased.

Materials known in the art may be used for the electron blocking layer or the hole blocking layer, and the compound represented by Formula 1 of the present invention may be preferably used as a material for the hole blocking layer.

The organic layer may further include a light emitting auxiliary layer (not shown) between the electron blocking layer and the light emitting layer 140 . The light emitting auxiliary layer may serve to transport holes to the light emitting layer 140 and to adjust the thickness of the organic material layer. For the light emitting auxiliary layer, a material known in the art may be used as a hole transport material.

The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarryl) Bazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS Used by dispersing in solvent-soluble resins such as resins and polyurethane resins, phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. It is also possible to

<Method for manufacturing organic electroluminescent device>

Each layer constituting the organic electroluminescent device is formed by depositing the material to be composed of each layer by vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular lamination, printing, spin coating or casting, coating method, etc. It can form by setting it as a thin film. There is no limitation in particular about the film thickness of each layer formed in this way, Although it can set suitably according to the property of a material, Usually, it is the range of 2 nm - 5000 nm. The film thickness can be usually measured with a crystal oscillation type film thickness measuring device or the like. In the case of thin film formation using the vapor deposition method, the deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. The deposition conditions are generally: heating temperature of the crucible for deposition +50~+400℃, vacuum degree ^10-6 ~ ^10-3Pa , deposition rate 0.01~50nm/sec, substrate temperature -150~+300℃, film thickness 2nm It is preferable to set suitably in the range of -5 micrometers.

Next, as an example of a method for manufacturing an organic electroluminescent device, an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode consisting of a host material and a dopant material. explain about

On a suitable substrate, a thin film of an anode material is formed by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for a cathode is formed by vapor deposition or the like to form a cathode. Thereby, a desired organic electroluminescent element is obtained. In addition, in the manufacture of the above-mentioned organic electroluminescent device, it is also possible to produce in the order of the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, the anode by reversing the manufacturing order.

<Application example of organic electroluminescent device>

Further, the present invention can also be applied to a display device including an organic electroluminescent device or a lighting device including an organic electroluminescent device.

A display device or a lighting device including an organic electroluminescent element is manufactured in the present embodiment by a known method such as connecting such an organic electroluminescent element and a known driving device (eg, a drain electrode or a source electrode of a thin film transistor). It can be driven by suitably using known driving methods such as DC driving, pulse driving, and AC driving.

As a display apparatus, flexible displays, such as panel displays, such as a color flat panel display, and a flexible color organic electroluminescence (EL) display, etc. are mentioned, for example (For example, Unexamined-Japanese-Patent No. 10-335066, See Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281706, etc.). Moreover, as a display method of a display, a matrix and/or a segment method etc. are mentioned, for example. In addition, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally, such as a grid shape or a mosaic shape, and a character or an image is displayed by a set of pixels. The shape or size of the pixel is determined depending on the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on PCs, monitors, and televisions, and in the case of large displays such as display panels, pixels with a side of the order of mm are used. do. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are displayed in a row. In this case, there are typically a delta type and a stripe type. Incidentally, as a driving method of this matrix, either a linear driving method or an active matrix may be used. Although line-sequential driving has an advantage in that it has a simple structure, an active matrix may be excellent when the operating characteristics are considered, so it is necessary to use this differently depending on the purpose.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is made to emit light. For example, time and temperature display in a digital watch or thermometer, operation state display of an audio device, an electronic cooker, etc., and a panel display of an automobile, etc. are mentioned.

Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, and the like (for example, Japanese Patent Laid-Open Nos. 2003-257621, 2003-277741, Japanese Patents See Publication No. 2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used in a liquid crystal display device, a watch, an audio device, an automobile panel, a display panel, a cover, and the like. In particular, as a backlight for a liquid crystal display device, especially a PC for which thinning is a problem, the backlight using the light emitting element according to the present embodiment is thin, considering that it is difficult to reduce the thickness because the conventional method consists of a fluorescent lamp or a light guide plate. , is characterized by light weight.

<Example>

The present invention will be more specifically described below by way of Examples, but the present invention is not limited thereto.

[Synthesis example of the compound of the present invention]

[Synthesis Example 1] Synthesis Example of Compound 2

Core 1 (5.5 g, 10.0 mmol), [1,1'-Biphenyl]-4-ylboronic acid (2.0 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O were added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified through silica column chromatography to obtain 5.5 g of the target compound (yield: 83%). [LCMS]: 662

[Synthesis Example 2] Synthesis example of compound 6

Core 1 (5.5 g, 10.0 mmol), (4-(Naphthalen-1-yl)phenyl)boronic acid (2.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 5.3 g (yield: 74%) of the target compound. [LCMS]: 712

[Synthesis Example 3] Synthesis example of compound 8

Core 1 (5.5 g, 10.0 mmol), (4'-Cyano-[1,1'-biphenyl]-3-yl)boronic acid (2.2 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were put into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O were added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 6.1 g (yield: 88%) of the target compound. [LCMS]: 687

[Synthesis Example 4] Synthesis Example of Compound 10

Core-1 (5.5 g, 10.0 mmol), 2-Naphthyl boronic acid (1.7 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) in a round bottom flask After putting it all in, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.7 g (yield: 74%) of the target compound. [LCMS]: 636

[Synthesis Example 5] Synthesis of compound 30

Core-2 (5.5 g, 10.0 mmol), (4-(naphthalen-1-yl)phenyl)boronic acid (2.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was put into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O were added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 6.2 g (yield: 88%) of the target compound. [LCMS]: 712

[Synthesis Example 6] Synthesis of compound 31

Core-2 (5.5 g, 10.0 mmol), 2-Naphthyl boronic acid (1.7 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) in a round bottom flask After putting it all in, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.9 g (yield: 77%) of the target compound. [LCMS]: 636

[Synthesis Example 7] Synthesis example of compound 33

Core 2 (5.5 g, 10.0 mmol), (Dibenzo[b,d]furan-4-ylboronic acid (2.1 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was put into a round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O were added, and the mixture was heated to reflux for 3 hours at 110° C. After completion of the reaction, the resulting solid was filtered. was dissolved in toluene and purified by silica column chromatography to obtain 5.2 g (yield: 77%) of the target compound. [LCMS]: 676

[Synthesis Example 8] Synthesis of compound 37

Core-3 (5.5 g, 10.0 mmol), (4-cyanophenyl)boronic acid (1.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) After putting everything in the bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. After dissolving the filtered solid in toluene, silica column chromatography was purified to obtain 4.0 g of the target compound (yield: 65%). [LCMS]: 611

[Synthesis Example 9] Synthesis of compound 38

Core-3 (5.5 g, 10.0 mmol), [1,1'-biphenyl]-4-ylboronic acid (2.0 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. After dissolving the filtered solid in toluene, silica column chromatography was purified to obtain 5.0 g of the target compound (yield: 75%). [LCMS]: 662

[Synthesis Example 10] Synthesis Example of Compound 48

Round core 3 (5.5 g, 10.0 mmol), (Phenyl-d ₅ )boronic acid (1.3 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) After putting everything in the bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 3.8 g (yield: 65 %) of the target compound. [LCMS]: 591

[Synthesis Example 11] Synthesis example of compound 73

Core 4 (6.0 g, 10.0 mmol), Phenylboronic acid (1.2 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were all put into a round bottom flask. , 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.8 g (yield: 75%) of the target compound. [LCMS]: 636

[Synthesis Example 12] Synthesis of compound 90

Core-2 (5.5 g, 10.0 mmol), ((4-(naphthalen-2-yl)phenyl)boronic acid (2.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH ( 1.2 g, 30.0 mmol) was put into a round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O were added, and the mixture was heated to reflux for 3 hours at 110° C. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.1 g (yield: 58%) of the target compound [LCMS]: 712

[Synthesis Example 13] Synthesis example of compound 92

Round core 5 (6.0 g, 10.0 mmol), (Phenyl-d ₅ )boronic acid (1.3 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) After putting everything in the bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 3.7 g (yield: 58 %) of the target compound. [LCMS]: 641

[Synthesis Example 14] Synthesis of compound 122

2-Bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-1 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 5.2 g (yield: 71%) of the target compound. [LCMS]: 738

[Synthesis Example 15] Synthesis example of compound 130

2-Bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-1 (4.3 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 5.1 g (yield: 71%) of the target compound. [LCMS]: 712

[Synthesis Example 16] Synthesis of compound 145

4-Bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-2 (3.8 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.2 g (yield: 63%) of the target compound. [LCMS]: 662

[Synthesis Example 17] Synthesis of compound 181

3-Bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-3 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. After dissolving the filtered solid in toluene, silica column chromatography was purified to obtain 6.4 g of the target compound (yield: 86%). [LCMS]: 738

[Synthesis Example 18] Synthesis Example of Compound 183

4-Bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-2 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g , 30.0 mmol) into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.7 g (yield: 63%) of the target compound. [LCMS]: 738

[Synthesis Example 19] Synthesis of compound 189

2'-bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-2 (3.8 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was put into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O were added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 3.9 g (yield: 59%) of the target compound. [LCMS]: 662

[Synthesis Example 20] Synthesis of compound 191

3'-bromospiro[fluorene-9,9'-xanthene] (4.1 g, 10.0 mmol), Sub-4 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was put into a round bottom flask, and then 50 ml of Toluene and 20 ml of H ₂ O were added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.9 g (yield: 66%) of the target compound. [LCMS]: 738

[Synthesis Example 21] Synthesis of compound 201

9-bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.6 g, 10.0 mmol), Sub-2 (3.8 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), After adding NaOH (1.2 g, 30.0 mmol) to the round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 5.3 g (yield: 74%) of the target compound. [LCMS]: 712

[Synthesis Example 22] Synthesis Example of Compound 202

9-Bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.6 g, 10.0 mmol), Sub-3 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), After adding NaOH (1.2 g, 30.0 mmol) to the round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 6.8 g (yield: 86%) of the target compound. [LCMS]: 788

[Synthesis Example 23] Synthesis of compound 218

4-bromospiro[benzo[b]fluorene-11,9'-xanthene] (4.6 g, 10.0 mmol), Sub-1 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), After adding NaOH (1.2 g, 30.0 mmol) to the round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. After dissolving the filtered solid in toluene, silica column chromatography was purified to obtain 5.5 g of the target compound (yield: 70%). [LCMS]: 788

[Synthesis Example 24] Synthesis of compound 224

9-bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.6 g, 10.0 mmol), Sub-5 (4.5 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), After adding NaOH (1.2 g, 30.0 mmol) to the round bottom flask, 50 ml of Toluene and 20 ml of H ₂ O are added. Then, it was heated and refluxed at 110° C. for 3 hours. After completion of the reaction, the resulting solid was filtered. The filtered solid was dissolved in toluene and purified by silica column chromatography to obtain 4.1 g (yield: 52%) of the target compound. [LCMS]: 788

Other compounds of the present invention can be synthesized by a method according to the above-described synthesis example by appropriately changing the raw material compound.

[Example 1]

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was washed with distilled water and ultrasonic waves. After completion of washing with distilled water, ultrasonic washing was performed with a solvent (isopropyl alcohol, acetone, methanol, etc.) and dried. A first hole injection layer was formed by thermal vacuum deposition of HI to a thickness of 40 nm on the prepared ITO transparent electrode. A second hole injection layer was formed by thermal vacuum deposition of HAT-CN to a thickness of 5 nm on the first hole injection layer, and HT, a material for transporting holes, was vacuum deposited on the second hole injection layer to a thickness of 20 nm. A hole transport layer was formed. Then, the host BH and the dopant BD (95:5 by weight) were vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting layer. ET-2 was deposited on the emission layer to a thickness of 10 nm to form an electron control layer, and Compound 2 was formed on the electron control layer to a thickness of 20 nm to form an electron transport layer. An organic light-emitting device was manufactured by sequentially depositing lithium fluoride (LiF) with a thickness of 1 nm on the electron transport layer and depositing aluminum with a thickness of 1,000 Å to form a cathode.

[Examples 2 to 15]

An organic light emitting device was prepared in the same manner as in Example 1, except that Compounds 10, 30, 31, 37, 38, 90, 122, 145, 181, 189, 191, 201, 218, and 224 were used instead of Compound 2 as the electron transport layer. prepared.

[Comparative Examples 1 to 4]

An organic light emitting diode was prepared in the same manner as in Example 1, except that Alq3, BCP, and Compounds A and B were used instead of Compound 2 as the electron transport layer.

As in Examples 1 to 15 and Comparative Examples 1 to 4, the measurement results of the driving voltage, current efficiency, emission peak and lifespan of the organic light emitting device prepared by using each compound as an electron transport layer (or electron control layer) material were [ Table 1].

[Table 1]

As can be seen from the measurement results shown in Table 1, the organic light emitting devices of Examples 1 to 15 using the compound of the present invention as the electron transport layer compared to the organic light emitting devices of Comparative Examples, at least one of driving voltage, current efficiency, and lifespan can be seen to be excellent.

100 boards
110 positive electrode (first electrode)
120 hole injection layer
130 hole transport layer
140 light emitting layer
150 electron transport layer
160 electron injection layer
170 cathode (second electrode)

Claims (14)

A compound represented by the following formula (1)
[Formula 1]

In Formula 1,
X ₁ and X ₂ are the same or different from each other, and are each independently selected from the group consisting of a direct bond, CR _a R _b , O, S or NR _c , and both X ₁ and X ₂ are not a direct bond,
R ₁ to R ₄ , R _a to R _c are the same as or different from each other, and each independently hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group , substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ - C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or Unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ selected from the group consisting of an arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring,
m, n, o and p are integers from 0 to 4,
L ₁ is a direct bond, a substituted or unsubstituted C ₃ -C ₃₀ arylene group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group is selected from the group consisting of,
A is represented by the following [Formula 2],
[Formula 2]

Y ₁ To Y ₁₀ Are the same as or different from each other, each independently N or CR _d , Y ₁ To Y ₁₀ At least one of N,
one of R _d of CR _d is bonded to L ₁ ,
R _d is hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, cyano group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted a C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₂₀ hetero Alkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₃ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₃ -C ₃₀ arylsilyl group, and substituted or unsubstituted C ₃ -C ₃₀ is selected from the group consisting of a heteroarylsilyl group, and adjacent groups may combine to form a substituted or unsubstituted ring. According to claim 1,
A compound wherein at least two of Y ₁ to Y ₁₀ are N. 3. The method of claim 2,
A is a compound having the following structure.

The compound according to claim 1, wherein X ₂ is a direct bond. 6. The compound of claim 5, wherein X ₁ is O. The compound according to claim 1, wherein X ₁ is a direct bond. The compound according to claim 1, wherein L ₁ is a direct bond. The compound according to claim 1, wherein L ₁ is a substituted or unsubstituted C ₃ -C ₃₀ arylene group. According to claim 1,
The compound of Formula 1 is any one of the following compounds.

a first electrode;
a second electrode opposite the first electrode;
An organic material layer interposed between the first electrode and the second electrode,
An organic electroluminescent device comprising the compound of claim 1 in the organic material layer. 11. The method of claim 10,
The first electrode is an anode,
The second electrode is a negative electrode,
The organic layer,
i) a light emitting layer;
ii) a hole transport region interposed between the first electrode and the light emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer;
iii) interposed between the light emitting layer and the second electrode and includes an electron transport region including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer,
wherein the electron transport region comprises the compound of claim 1 ,
Organic electroluminescent device. The organic electroluminescent device according to claim 11, wherein the electron transport layer or the hole blocking layer comprises the compound. The alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, wherein the electron transporting layer and/or the electron injecting layer is An organic electroluminescent device further comprising at least one selected from the group consisting of rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. A display device comprising the organic electroluminescent device of claim 10, wherein a first electrode of the organic electroluminescent device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

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