KR102066794B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic electroluminescent device including the same.

Description

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification relates to a compound and an organic electroluminescent device including the same.

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2017-0083558 filed with the Korea Intellectual Property Office on June 30, 2017, the contents of which are incorporated herein in their entirety.

The electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as necessary. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of the material of the organic thin film is continuously required.

Korean Laid-Open Patent Publication 2000-0051826

The present specification provides a compound and an organic electroluminescent device including the same.

The present application provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

X and Y are the same as each other and are O, S, NR, PR 'or P (= 0) R ",

A and B are the same as each other, a benzene ring or a naphthalene ring,

R1 and R2 are the same as each other, a substituted or unsubstituted bicyclic or more aryl group,

R, R ', and R "are the same as or different from each other, and are each independently a methyl group, an ethyl group, or a phenyl group.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

The compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve light efficiency, and improve device life characteristics by thermal stability of the compound.

1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows an organic electric field in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7 and a cathode 4 are sequentially stacked. An example of a light emitting element is shown.
3 is a mass spectrum of Compound 8 according to one embodiment of the present invention.
4 is a mass spectrometry spectrum of Compound 28 according to an embodiment of the present invention.
5 is a mass spectrometry spectrum of the compound 96 according to an exemplary embodiment of the present invention.
6 is a mass spectrometry spectrum of Compound 98 according to an embodiment of the present invention.
7 is a mass spectrometry spectrum of the compound 102 according to an exemplary embodiment of the present invention.
8 is a mass spectrum of a compound 106 according to an exemplary embodiment of the present invention.
9 is a mass spectrum of a compound 116 according to one embodiment of the present invention.
10 is a mass spectrum of Compound 124 according to one embodiment of the present invention.
11 is a mass spectrum of a compound 139 according to one embodiment of the present invention.
12 is a mass spectrum of Compound 239 according to one embodiment of the present invention.
13 is a mass spectrum of a compound 244 according to one embodiment of the present invention.
14 is a mass spectrum of a compound 252 according to one embodiment of the present invention.
15 is a mass spectrum of a compound 297 according to one embodiment of the present invention.
16 is a mass spectrum of a compound 384 according to one embodiment of the present invention.
17 is a mass spectrum of a compound 532 according to one embodiment of the present invention.
18 is a mass spectrum of a compound 534 according to one embodiment of the present invention.
19 is a mass spectrum of a compound 535 according to one embodiment of the present invention.
20 is a mass spectrum of Compound 537 according to an exemplary embodiment of the present invention.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a compound represented by Chemical Formula 1.

Examples of substituents herein are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Silyl groups; Amine group; Substituted or unsubstituted phosphine oxide group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

In addition, the substituent to which two or more substituents are linked may be a biphenyl group, and may be a terphenyl group. Dimethylfluorene group or diphenyltriazine group can also be interpreted as a substituent to which two or more different substituents are linked.

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

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50. Specific examples 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 60 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 are not limited thereto. Do not.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and N-9-methyl-anthracenyl Amine group, diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-biphenylfluorenylamine group, N-phenylfluorenylamine Group, N-phenylspirobifluorenylamine group, N-biphenylspirobifluorenylamine group, N-biphenyl dibenzofuranylamine group, N-phenylphenanthrenylamine group, N-biphenylphenan Trenylamine group, N-phenyldibenzofuranylamine group, N-phenylbiphenylamine group, N-phenylcarbazolylamine group, N-biphenylcarbazolylamine group, N-biphenyldibenzothiophenylamine group , N-phenyldibenzothiophenylamine group, N-biphenylnaphthylamine group, N-biphenylterphenylamine group, N-phenylterphenylamine group, N-phenylnaphthylamine group, N-quaterphenyl Luorenylamine group, N-terphenylfluorenylamine group, difluorenylamine group, N-phenylbenzocarbazolylamine group, N-biphenylbenzocarbazolylamine group, N-fluorenylcarbazolylamine And the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

Etc., but is not limited thereto.

,

등이 있다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl Group, acridil group, hydroacridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazin Ginopyrazinyl group, isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzo Thiophenyl group, benzofuranyl group, dibenzofuranyl group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenooxazinyl group, and Although there are condensation structures and the like, but only those no. In addition, examples of heterocyclic groups include heterocyclic structures including a sulfonyl group, for example,

,

Etc.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, the definitions of X, Y, R1, and R2 are the same as those of Formula 1.

In one embodiment of the present specification, the bonding positions of R1 and R2 of the compound represented by Formula 1 are point symmetric with each other. In the case of point-symmetrical compounds, it is asymmetric or easier to synthesize than the line-symmetrical compound, and the deposition structure of molecules is dense during deposition, resulting in efficient transfer of electrons and holes, and it is possible to manufacture high-performance organic light emitting devices. Do.

In one embodiment of the present specification, the point symmetry means that the two figures completely overlap when the center of Formula 1 is rotated 180 °. Specifically, when the compound is rotated 180 ° in the a direction about * in the following structural formula, it means that it overlaps completely with the figure before rotation.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Chemical Formulas 1-1 to 1-8, the definitions of X, Y, R1, and R2 are the same as the definitions of Chemical Formula 1.

In one embodiment of the present specification, X and Y are the same.

In one embodiment of the present specification, X and Y are O.

In one embodiment of the present specification, X and Y are S.

In one embodiment of the present specification, X and Y are NR, and R is a methyl group, an ethyl group, or a phenyl group.

In one embodiment of the present specification, X and Y are NR, and R is a methyl group or a phenyl group.

In one embodiment of the present specification, X and Y are PR ', and R' is a methyl group, an ethyl group or a phenyl group.

In one embodiment of the present specification, X and Y are PR ', and R' is a methyl group or an ethyl group.

In one embodiment of the present specification, X and Y are P (= 0) R ″, and R ″ is a methyl group, an ethyl group, or a phenyl group.

In one embodiment of the present specification, X and Y are P (= 0) R ″, and R ″ is a methyl group or an ethyl group.

In one embodiment of the present specification, R1 and R2 are the same.

In one embodiment of the present specification, R1 and R2 are substituted or unsubstituted aryl groups having 10 to 30 carbon atoms.

In one embodiment of the present specification, R1 and R2 are substituted or unsubstituted naphthyl groups; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted pyrene group; Substituted or unsubstituted fluoranthene group; Or a substituted or unsubstituted triphenylene group.

In one embodiment of the present specification, R1 and R2 are substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group Or an unsubstituted naphthyl group; Anthracene groups unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group; Phenanthrene groups unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group; Pyrene groups unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group; A fluoranthene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group; Or a triphenylene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a silyl group, and an amine group.

In one embodiment of the present specification, R1 and R2 are selected from the following structural formulas.

In the above structural formula, R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted silyl group; Or a substituted or unsubstituted amine group.

In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Profile group; Butyl group; Cyclohexyl group; Cyclopentyl group; Trimethylsilyl group; Butyl dimethyl silyl group; Butyl diphenyl silyl group; Triphenylsilyl group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted diphenylamine group.

In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Profile group; Butyl group; Cyclohexyl group; Cyclopentyl group; Trimethylsilyl group; Butyl dimethyl silyl group; Butyl diphenyl silyl group; Triphenylsilyl group; A phenyl group unsubstituted or substituted with deuterium; Naphthyl group; Biphenyl group; Dibenzofuran group; Pyrene group; Or a diphenylamine group.

In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently hydrogen, deuterium, F, cyano group, methyl group, ethyl group, propyl group, butyl group, cyclohexyl group, cyclopentyl group, Trimethylsilyl group, butyldimethylsilyl group, butyldiphenylsilyl group, triphenylsilyl group, phenyl group, naphthyl group, anthracene group, fluorene tan group, phenanthrene group, triphenylene group, fluorene group, dibenzofuran group, di Benzothiophene group, carbazole group, spirobifluorene group, dibenzonaphthofuran group, dibenzonaphthothiophene group, quinazoline group, triazine group, quinoxaline group, and diphenylamine group It is one or more substituents.

In one embodiment of the present specification, R3 and R4 are selected from the following structural formulas.

In one embodiment of the present specification, R3 or R4 is deuterium; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; An amine group substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R3 or R4 is deuterium, F, cyano group, methyl group, ethyl group, propyl group, butyl group, cyclohexyl group, cyclopentyl group, trimethylsilyl group, butyldimethylsilyl group, butyldiphenyl Silyl group, triphenylsilyl group, phenyl group, naphthyl group, anthracene group, fluorene tan group, phenanthrene group, triphenylene group, fluorene group, dibenzofuran group, dibenzothiophene group, carbazole group, spirobifluorene Group, a dibenzonaphthofuran group, a dibenzonaphthothiophene group, a quinazoline group, a triazine group, and a quinoxaline group, and an amine group substituted with one or more substituents.

In one embodiment of the present specification, R3 or R4 is -NR5R6, R5 and R6 are the same as or different from each other, and are each independently selected from the following structural formulas.

In one embodiment of the present specification, R1 and R2 are substituted or unsubstituted aryl groups having 10 to 30 carbon atoms.

In one embodiment of the present specification, the compound of Formula 1 is selected from the following structural formulas.

In addition, the present specification provides an organic electroluminescent device comprising the compound described above.

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic EL device of the present invention, the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a blue light emitting host.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer includes the compound of Formula 1.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, the hole injection layer, a hole transport layer or a hole injection and transport layer comprises a compound of formula (1).

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of Formula 1.

In an exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer or an electron injection and transport layer, and the electron injection layer, an electron transport layer or an electron injection and transport layer includes the compound of Formula 1.

In an exemplary embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound of Formula 1.

In one embodiment of the present application, the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. 2 or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the compound of Formula 1.

In an exemplary embodiment of the present application, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.

In an exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in an exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, other materials except for the compound may be the same or different from each other.

In an exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

 In another exemplary embodiment, the organic EL device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic electric field in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7 and a cathode 4 are sequentially stacked. The structure of the light emitting element is illustrated. In such a structure, the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.

The organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include dibenzofuran derivatives, ladder type furan compounds, and pyrides. Midine derivatives and the like, but is not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic electroluminescent device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

The preparation of the compound represented by Chemical Formula 1 and the organic electroluminescent device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Synthesis Example

Preparation Example 1 Synthesis of Intermediate A

                                                        Intermediate A

1,6-Dibromodibenzodioxine (20 g, 58.48 mmol), bis (pinacol) diboron (37.1 g, 146.2 mmol) and potassium acetate (28.7 g, 292.4 mmol) were placed in a round bottom flask and dioxane It was dissolved in 500 mL and refluxed. Bis (dibenzylideneacetone) palladium (0) (Pd (dba) 2; 705 mg, 1.22 mmol) and tricyclohexylphosphine (PCy3; 668 mg, 2.45 mmol) were dissolved in 30 mL of dioxane and stirred for 30 minutes. Then added. After refluxing for 24 hours, cooled and filtered, then 500 mL of water was added. The mixture was extracted three times with 300 mL of toluene and the organic layer was concentrated under reduced pressure. Intermediate A was obtained via column chromatography (21.4 g, 49.1 mmol).

Preparation Example 2 Synthesis of Intermediate B

                                                   Intermediate B

Intermediate B was obtained by the same method as the intermediate A, except that 2,7-dibromobenzodioxine was used instead of 1,6-dibromobenzodioxin.

Preparation Example 3 Synthesis of Intermediate C

                                                    Intermediate C

Intermediate C was obtained in the same manner as in Intermediate A, except that 5,12-dibromodinaphthodioxin was used instead of 1,6-dibromobenzodioxin.

Preparation Example 4 Synthesis of Intermediate D

                                                   Intermediate D

Intermediate D was obtained in the same manner as in Intermediate A, except that 2,7-dibromothianthrene was used instead of 1,6-dibromobenzodioxin.

Preparation Example 5 Synthesis of Intermediate E, F, G

                  Intermediate E Intermediate F Intermediate G

3-bromo-4- (phenylamino) phenol (30 g, 113.58 mmol) and sodium tert-butoxide (21.83 g, 227.2 mmol) were dissolved in 1000 mL of toluene and placed in a round bottom flask to reflux. Bis (tritertbutylphosphine) palladium (0) (BTP; 116 mg, 0.227 mmol) was added and refluxed for 12 hours, cooled to room temperature and 500 mL of water was added. The mixture was extracted three times with 300 mL of toluene and the organic layer was concentrated under reduced pressure. Intermediate E was obtained via column chromatography (14.8 g, 40.32 mmol).

The obtained intermediate E (14.8 g, 40.32 mmol) was dissolved in 300 mL of dichloromethane and 300 mL of pyridine and placed in a round bottom flask and cooled to 0 ° C. Anhydrous triflate (Tf 2 O; 28.4 g, 100.8 mmol) was added slowly and stirred for 12 h. The mixture was washed four times with 500 mL of 2 M HCl aqueous solution to remove pyridine, and the organic layer was concentrated under reduced pressure to obtain Intermediate F (24.2 g, 38.3 mmol).

Intermediate G was obtained by the same method as the intermediate A, except that intermediate F was used instead of 1,6-dibromobenzodioxin.

Preparation Example 6 Synthesis of Intermediate H, I, J

               Intermediate H Intermediate I Intermediate J

1,2-dibromo-4-methoxybenzene (30 g, 112.8 mmol) was dissolved in 500 mL of a tetrahydrofuran and diethyl ether 1: 1 mixed solution and cooled to -78 ^° C. 1.6 M n-butyllithium solution (155 mL, 248.2 mmol) was slowly added dropwise and stirred for 1 hour. Dichloro (ethyl) phosphine (EtPCl2; 36.9 g, 282.0 mmol) was dissolved in 50 mL of tetrahydrofuran and slowly added dropwise, followed by stirring for 5 hours while gradually warming to room temperature. 500 mL of toluene was added to the mixture, washed three times with 300 mL of water, and the organic layer was concentrated under reduced pressure and recrystallized with chloroform to obtain an intermediate H (10.8 g, 32.7 mmol).

Intermediate H (10 g, 30.1 mmol) was dissolved in 200 mL of dichloromethane and cooled to -20 ° C. Boron tribromide (BBr 3; 30 g, 120.3 mmol) was slowly added dropwise and stirred for 3 hours. The mixture was slowly added 300 mL of potassium bicarbonate 2 M solution and the aqueous layer was removed four times. The organic layer was concentrated under reduced pressure and recrystallized from chloroform to obtain Intermediate I (8.52 g, 28.0 mmol).

Intermediate J was obtained in the same manner as the intermediate F and the intermediate G, except that Intermediate I was used instead of Intermediate E.

Preparation Example 7 Synthesis of Intermediates K and L

   Intermediate H Intermediate K Intermediate L

Intermediate H (20 g, 60.2 mmol) was dissolved in 300 mL of dichloromethane and 200 mL of 30% hydrogen peroxide solution was added. After stirring for 3 hours, the aqueous layer was removed and washed twice with 200 mL of water. The organic layer was concentrated under reduced pressure and recrystallized with chloroform to obtain an intermediate K (20.2 g, 55.4 mmol).

Intermediate L was obtained in the same manner as Intermediate J, except that Intermediate K was used instead of Intermediate I.

Preparation Example 8 Synthesis of Compound 8

Intermediate A Compound 8

Intermediate A (10.8 g, 24.85 mmol) and 2-bromotriphenylene (16 g, 52.18 mmol) were dissolved in 500 mL of dioxane. Calcium carbonate (17.2 g, 124.2 mmol) was added in 100 mL of pure water and bis (tritertbutylphosphine) palladium (0) (BTP; 63.5 mg, 0.124 mmol) was added. It was refluxed for 2 hours, cooled and filtered. The filtered solid was recrystallized from toluene to give compound 8 (15.29 g, 19.38 mmol).

Mass spectra of the compound 8 are shown in FIG. 3.

Preparation Example 9 Synthesis of Compound 28

Intermediate A Compound 28

Compound 28 was obtained by the same method as Compound 8, except that 10-bromo-N, N-diphenylanthracene-9-amine was used instead of 2-bromotriphenylene.

Mass spectrometry of the compound 28 is shown in FIG. 4.

Preparation Example 10 Synthesis of Compound 96

   Intermediate B Compound 96

Compound 96 was obtained by the same method as Compound 8, except that Intermediate B and 9-bromo-10- (phenyl-d5) anthracene were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry of the compound 96 is shown in FIG. 5.

Preparation Example 11 Synthesis of Compound 98

  Intermediate B Compound 98

Compound 98 was obtained by the same method as Compound 8, except that Intermediate B and 9-bromo-10- (naphthalen-2-yl) anthracene were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry of the compound 98 is shown in FIG. 6.

Preparation Example 12 Synthesis of Compound 102

Intermediate B Compound 102

Compound 102 was obtained by the same method as Compound 8, except that Intermediate B and 2- (10-bromoanthracene-9-yl) dibenzofuran were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry spectra of the compound 102 are shown in FIG. 7.

Preparation Example 13 Synthesis of Compound 106

Intermediate B Compound 106

Compound 106 was obtained by the same method as Compound 8, except that Intermediate B and 10-bromo-1,8-diphenylanthracene were used instead of Intermediate A and 2-bromotriphenylene.

The mass spectrometry spectrum of the compound 106 is shown in FIG. 8.

Preparation Example 14 Synthesis of Compound 116

Intermediate B Compound 116

Synthesis by the same method as Compound 8, except that Intermediate B and 10-bromo-N, N-bis (4-tertbutylbutylphenyl) anthracene-9-amine were used in place of Intermediate A and 2-bromotriphenylene Compound 116 was obtained.

Mass spectrometry of the compound 116 is shown in FIG. 9.

Preparation Example 15 Synthesis of Compound 124

Intermediate C Compound 124

Compound 124 was obtained by the same method as Compound 8, except that Intermediate C and 10-bromo-9- (naphthalen-1-yl) anthracene were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry spectra of the compound 124 are shown in FIG. 10.

Preparation Example 16 Synthesis of Compound 139

Intermediate C Compound 139

Compound 139 was obtained by the same method as Compound 8, except that Intermediate C and 1-bromopyrene were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry of the compound 139 is shown in FIG. 11.

Preparation Example 17 Synthesis of Compound 239

Intermediate D Compound 239

Compound 239 was obtained by the same method as Compound 8, except that Intermediate D and 9-bromo-10-phenylanthracene were used instead of Intermediate A and 2-bromotriphenylene.

Mass spectrometry spectra of the compound 239 are shown in FIG. 12.

Preparation Example 18 Synthesis of Compound 244

Intermediate D Compound 244

Synthesis in the same manner as in Compound 8, except that Intermediate D and 9-([1,1'-biphenyl] -4-yl) -10-bromoanthracene were used in place of Intermediate A and 2-bromotriphenylene Compound 244 was obtained.

Mass spectrometry of the compound 244 is shown in FIG. 13.

Preparation Example 19 Synthesis of Compound 252

Intermediate D Compound 252

Compound 252 was obtained by the same method as Compound 8 except for using Intermediate D and 10-bromo-1,8-di (naphthalen-2-yl) anthracene in place of Intermediate A and 2-bromotriphenylene. .

Mass spectrometry spectra of the compound 252 are shown in FIG. 14.

Preparation Example 20 Synthesis of Compound 297

Intermediate G Compound 297

Compound 297 was obtained by the same method as Compound 8, except that Intermediate G and 3-bromofluoranthene were used instead of Intermediate A and 2-bromotriphenylene.

The mass spectrometry spectrum of the compound 297 is shown in FIG. 15.

Preparation Example 21 Synthesis of Compound 384

Intermediate G Compound 384

Compound 384 was obtained by the same method as Compound 8 except for using Intermediate G and 9-bromo-10- (phenyl-d5) anthracene in place of Intermediate A and 2-bromotriphenylene.

The mass spectrometry spectrum of the compound 384 is shown in FIG. 16.

Preparation Example 22 Synthesis of Compound 532

Intermediate L Compound 532

Synthesis in the same manner as in Compound 8, except that Intermediate L and 9-([1,1'-biphenyl] -4-yl) -10-bromoanthracene were used in place of Intermediate A and 2-bromotriphenylene Compound 532 was obtained.

Mass spectrometry spectra of the compound 532 are shown in FIG. 17.

Preparation 23. Synthesis of Compound 534

Intermediate L Compound 534

Compound 534 was obtained by the same method as Compound 8, except that Intermediate L and 2- (10-bromoanthracene-9-yl) dibenzofuran were used instead of Intermediate A and 2-bromotriphenylene.

The mass spectrometry spectrum of the compound 534 is shown in FIG. 18.

Preparation 24. Synthesis of Compound 535

Intermediate J Compound 535

Compound 535 was obtained by the same method as Compound 8 except for using Intermediate J and (4- (10-bromoanthracene-9-yl) phenyl) trimethylsilane in place of Intermediate A and 2-bromotriphenylene .

The mass spectrometry spectrum of the compound 535 is shown in FIG. 19.

Preparation 25. Synthesis of Compound 537

Intermediate J Compound 537

Compound 537 was obtained by the same method as Compound 8, except that Intermediate J and 9-bromo-10-cyclohexylanthracene were used instead of Intermediate A and 2-bromotriphenylene.

The mass spectrometry spectrum of the compound 537 is shown in FIG. 20.

Experimental Example

Comparative Example 1

The glass substrate coated with ITO (indium tin oxide) at a thickness of 1,500 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol was carried out and dried, and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.

(HAT)

(HAT)

4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 kV) of the following formula, which is a material for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. Formed.

(NPB)

(NPB)

Subsequently, 9- (naphthalen-1-yl) -10- (naphthalen-2-yl) anthracene (BH1) of the formula below was vacuum deposited to a light emitting layer host to form a light emitting layer on the hole transport layer.

(BH1)

(BH1)

While depositing the light emitting layer, 4 wt% of the following compound N4, N9-bis (dibenzofuran-4-yl) -N4, N9-di-m-tolylpyrene-4,9-diamine (BD1) was used as a blue light emitting dopant. It was.

(BD1)

(BD1)

Alq ₃ (aluminum tris (8-hydroxyquinoline)) having the following chemical formula was vacuum deposited on the emission layer to form a electron injection and transport layer.

(Alq₃)

(Alq ₃ )

On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited in a thickness of 12 kPa in order to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, aluminum is 2 속도 / sec, the vacuum degree during deposition is 2Х10 ^-7 ˜5Х10 ⁻⁸ torr was maintained.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that 2,7-diphenyldibenzodioxane (BH2) was used instead of BH1 in Comparative Example 1.

Comparative Example 3

In Comparative Example 1, 4,4 '-(thianthrene-2,7-diyl) bis (N, N'-diphenylaniline) (BH3) was used instead of BH1, and the organic light emission was the same as that of Comparative Example 1 The device was produced.

<Comparative Example 4>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that 2,7-di (carbazol-9-yl) dibenzodioxane (BH4) was used instead of BH1 in Comparative Example 1.

Comparative Example 5

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that 2,8-bis (10-phenylanthracene-9-yl) dibenzodioxin (BH5) was used instead of BH1 in Comparative Example 1.

<Example 1>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 8 was used in Comparative Example 1.

<Example 2>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 28 was used in Comparative Example 1.

<Example 3>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 96 was used in Comparative Example 1.

<Example 4>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 98 was used in Comparative Example 1.

Example 5

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 102 was used in Comparative Example 1.

<Example 6>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 106 was used in Comparative Example 1.

<Example 7>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 116 was used in Comparative Example 1.

<Example 8>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 124 was used in Comparative Example 1.

Example 9

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 139 was used in Comparative Example 1.

<Example 10>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 239 was used in Comparative Example 1.

<Example 11>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 244 was used in Comparative Example 1.

<Example 12>

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 252 was used in Comparative Example 1.

Example 13

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 297 was used in Comparative Example 1.

<Example 14>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 384 was used in Comparative Example 1.

<Example 15>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 532 was used in Comparative Example 1.

<Example 16>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 534 was used in Comparative Example 1.

<Example 17>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 535 was used in Comparative Example 1.

Example 18

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that BH1 Compound 537 was used in Comparative Example 1.

The driving voltage, the luminous efficiency, and the lifetime of the organic light emitting diodes manufactured in Comparative Examples 1 to 5 and Examples 1 to 18 were measured at a current density of 20 mA / cm ² , and are shown in Table 1 below.

Example Host substance Drive voltage (V) Luminous Efficiency (Cd / A) Lifespan T97% (hours) Comparative Example 1 BH1 5.29 6.75 130 Comparative Example 2 BH2 5.03 0.28 3 Comparative Example 3 BH3 5.08 0.12 2 Comparative Example 4 BH4 5.11 1.53 3 Comparative Example 5 BH5 5.15 6.79 92 Example 1 Compound 8 5.13 6.76 126 Example 2 Compound 28 5.01 6.82 146 Example 3 Compound 96 5.10 6.88 168 Example 4 Compound 98 5.09 6.81 160 Example 5 Compound 102 4.99 6.84 173 Example 6 Compound 106 5.04 6.79 159 Example 7 Compound 116 5.00 6.89 149 Example 8 Compound 124 5.12 6.84 154 Example 9 Compound 139 5.19 6.87 129 Example 10 Compound 239 5.17 6.82 107 Example 11 Compound 244 5.20 6.80 112 Example 12 Compound 252 5.14 6.80 118 Example 13 Compound 297 5.14 6.86 120 Example 14 Compound 384 5.10 6.83 159 Example 15 Compound 532 5.04 6.81 149 Example 16 Compound 534 4.98 6.79 157 Example 17 Compound 535 5.07 6.82 129 Example 18 Compound 537 5.08 6.80 138

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron injection and transport layer

Claims (12)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
X and Y are the same as each other and are O, S, NR, PR 'or P (= 0) R ",
A and B are the same as each other, a benzene ring or a naphthalene ring,
R1 and R2 are the same as each other, a substituted or unsubstituted bicyclic or more aryl group,
R, R ', and R "are the same as or different from each other, and are each independently a methyl group, an ethyl group, or a phenyl group,
The bonding positions of R1 and R2 of the compound represented by Formula 1 are point symmetric with each other. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, the definitions of X, Y, R1, and R2 are the same as those of Formula 1. delete The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Chemical Formulas 1-1 to 1-8, the definitions of X, Y, R1, and R2 are the same as the definitions of Chemical Formula 1. The compound of claim 1, wherein R 1 and R 2 are selected from the following structural formulas:

In the above structural formula, R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted silyl group; Or a substituted or unsubstituted amine group. The compound of claim 5, wherein R 3 and R 4 are selected from the following structural formulas:

The method of claim 5, wherein R 3 or R 4 is deuterium; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; And an amine group substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heteroring group. The compound of claim 5, wherein R 3 or R 4 is —NR 5 R 6, wherein R 5 and R 6 are the same as or different from each other, and are each independently selected from the following structural formulas:

A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a compound according to any one of claims 1, 2, and 4 to 8. It comprises an organic electroluminescent device. The organic electroluminescent device according to claim 9, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic electroluminescent device according to claim 9, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer includes the compound. The organic electroluminescent device according to claim 9, wherein the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection and transport layer includes the compound.

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