KR102196624B1 - Organic light emitting device - Google Patents

Abstract

The present application is a positive electrode; A negative electrode provided opposite to the positive electrode; And an organic material layer between the anode and the cathode,
The organic material layer includes a light emitting layer comprising a compound represented by the following formula (2),
It is provided between the light emitting layer and the anode, and relates to an organic light emitting device further comprising an organic material layer comprising a compound represented by the following formula (1).

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present application relates to an organic light emitting device.

This application claims the interests of the filing date of the Korean Patent Application No. 10-2018-0005888 filed with the Korean Intellectual Property Office on January 17, 2018, all of which are included in the specification.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

International Patent Application Publication No. 2003-012890

The present application is to provide an organic light emitting device.

The present invention is a positive electrode; A negative electrode provided opposite to the positive electrode; And an organic material layer between the anode and the cathode,

The organic material layer includes a light emitting layer comprising a compound represented by the following formula (2),

It is provided between the light emitting layer and the anode, and provides an organic light emitting device further comprising an organic material layer containing a compound represented by the following formula (1).

Provides.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 8, and when m is 2 or more, R1 is the same as or different from each other,

n is an integer from 0 to 7, and when n is 2 or more, R2 is the same as or different from each other,

R3 and R4 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L2 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

Ar3 is a tricyclic or more heterocyclic group containing two substituted or unsubstituted N,

R10 to R19 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two groups adjacent to each other may be bonded to each other to form a ring.

The organic light-emitting device according to the exemplary embodiment of the present application has a low driving voltage, and can improve lifespan characteristics of the device by thermal stability of the compound.

1 to 5 illustrate examples of an organic light-emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

The present specification is a positive electrode; A negative electrode provided opposite to the positive electrode; And an organic material layer between the anode and the cathode,

The organic material layer includes a light emitting layer comprising a compound represented by the following formula (2),

It is provided between the light emitting layer and the anode, and provides an organic light emitting device further comprising an organic material layer containing a compound represented by the following formula (1).

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 8, and when m is 2 or more, R1 is the same as or different from each other,

n is an integer from 0 to 7, and when n is 2 or more, R2 is the same as or different from each other,

R3 and R4 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

L2 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

Ar3 is a tricyclic or more heterocyclic group containing two substituted or unsubstituted N,

R10 to R19 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two groups adjacent to each other may be bonded to each other to form a ring.

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

In the exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 is a hole transport layer.

In an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 is an electron suppressing layer.

In an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 is a hole transport and electron suppression layer.

According to an exemplary embodiment of the present specification, the thickness of the organic material layer including the compound represented by Formula 1 is 100 Å to 2000 Å.

According to an exemplary embodiment of the present specification, the thickness of the organic material layer including the compound represented by Formula 1 is 100 Å to 1500 Å.

According to an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 is a hole transport layer, and the thickness of the hole transport layer is 300 Å to 2000 Å.

According to an exemplary embodiment of the present specification, the organic material layer including the compound represented by Formula 1 is an electron-storing layer, and the thickness of the electron-suppressing layer is 30 Å to 400 Å.

According to the exemplary embodiment of the present specification, the thickness of the emission layer is 100 Å to 500 Å.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Alkoxy group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" 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 connected.

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, and the number of carbon atoms 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, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and 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. Does not.

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

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 24 carbon atoms. Specifically, 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 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,

,

,

And the like, but is not limited thereto.

), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기; 벤조실롤기; 디벤조실롤기; 페난트롤리닐기(phenanthrolinyl group), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대,

,

등이 있다.In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups 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, acridyl group, hydroacridyl group (for example,

), pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzo Furanyl group; Benzosilol group; Dibenzosilol group; There are phenanthrolinyl group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenooxazinyl group, and condensation structures thereof. , It is not limited to these. In addition, as an example of a heterocyclic group, a heterocyclic structure including a sulfonyl group, for example,

,

Etc.

In the present specification, the "adjacent" group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, or another substituent substituted on an atom where the corresponding substituent is substituted. 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 to each other.

In the present specification, the meaning of adjacent groups being bonded to each other to form a ring means that adjacent groups are bonded to each other as described above to form a 5 to 8 membered hydrocarbon ring or a 5 to 8 membered heterocycle, and , It may be monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-3 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The L1, Ar1, Ar2, R3 and R4 are as defined in Chemical Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-7 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,

The L2 and Ar3 are as defined in Chemical Formula 2.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzonaphthofuran group; Or a substituted or unsubstituted benzonaphthothiophene group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a cyano group, a halogen group, a silyl group, an alkyl group, an aryl group, or a phenyl group unsubstituted or substituted with a heterocyclic group; Biphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Terphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Quarterphenyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Naphthyl group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Triphenylene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Anthracene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Phenanthrene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; A fluorenyl group unsubstituted or substituted with deuterium, a cyano group, a halogen group, a silyl group, an alkyl group or an aryl group; Dibenzofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Dibenzothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Carbazole group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Benzonaphthofuran group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group; Or a benzonaphthothiophene group unsubstituted or substituted with deuterium, cyano group, halogen group, silyl group, alkyl group or aryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium, cyano group, F, trimethylsilyl group, methyl group, butyl group, phenyl group, naphthyl group, fluorene group, dibenzo A phenyl group unsubstituted or substituted with a furan group or a dibenzothiophene group; Biphenyl group; Terphenyl group; Quarter phenyl group; Naphthyl group; Triphenylene group; Phenanthren group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzothiophene group; Or a dibenzofuran group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the following structural formulas.

In the above structural formula, a dotted line means a position bonded to N in Formula 1.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylylene group; A substituted or unsubstituted quiterphenylylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted dimethylfluorenylene group; A substituted or unsubstituted divalent phenanthrene group; A substituted or unsubstituted divalent pyrene group; Or a substituted or unsubstituted divalent triphenylene group.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylylene group; Quiterphenylylene group; Naphthylene group; Anthracenylene group; Dimethylfluorenylene group; A divalent phenanthren group; Divalent pyrene group; Or a divalent triphenylene group.

In the exemplary embodiment of the present specification, L1 is a direct bond or a phenylene group.

In the exemplary embodiment of the present specification, L1 is a direct bond or a para-phenylene group.

In the exemplary embodiment of the present specification, L2 is a direct bond; Phenylene group; Or it is a naphthylene group.

In an exemplary embodiment of the present specification, Ar3 is represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3, the dotted line means a position bonded to L2,

X is S, O or C(R25)(R26),

R20 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, X is S.

In the exemplary embodiment of the present specification, X is O.

In the exemplary embodiment of the present specification, X is C(R25)(R26), R25 and R26 are the same as or different from each other, and each independently an alkyl group.

In the exemplary embodiment of the present specification, X is C(R25)(R26), and R25 and R26 are methyl groups.

In the exemplary embodiment of the present specification, R20 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted benzofluorenyl group.

In the exemplary embodiment of the present specification, R20 is a phenyl group; Naphthyl group; A carbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; A benzocarbazole group unsubstituted or substituted with a phenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a methyl group or a phenyl group substituted or unsubstituted benzofluorenyl group.

In the exemplary embodiment of the present specification, R20 is a phenyl group; Naphthyl group; A carbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Dibenzothiophene group; A benzocarbazole group unsubstituted or substituted with a phenyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Or a benzofluorenyl group unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, R21 to R24 are hydrogen.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following structural formulas.

In an exemplary embodiment of the present specification, the compound represented by Formula 2 is selected from the following structural formulas.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is 30% by weight to 100% by weight based on the total weight of the emission layer.

Materials that can be used in the light emitting layer together with the compound represented by the above formula (2) include, for example, naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenyl. Condensed polycyclic aromatic compounds such as cyclopentadiene, pentaphenylcyclopentadiene, fluorene, and spirofluorene, and derivatives thereof, organic metal complexes such as tris(8-quinolinolate)aluminum, triarylamine derivatives, styrylamine Derivatives, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives, Quinacridone derivatives and the like may be mentioned, but are not limited thereto.

In the organic light-emitting device, in addition to the light-emitting material, a light-emitting dopant (a phosphorescent dopant and/or a fluorescent dopant) may be contained in the light-emitting layer. In addition, an emission layer including these dopants may be stacked on the emission layer including the compound represented by Formula 2 above.

Fluorescent dopants are compounds that can emit light from singlet excitons. Fluorescent dopants are required from amine compounds, aromatic compounds, chelate complexes such as tris(8-quinolinolate)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc. It is preferable that it is a compound selected in accordance with the luminous color to be obtained, a styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable, and an arylamine derivative is still more preferable. These fluorescent dopants may be used alone or in combination of a plurality of them.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is a host material for the emission layer.

According to the exemplary embodiment of the present specification, the emission layer may further contain a dopant material.

According to an exemplary embodiment of the present specification, the dopant material is 1 to 30% by weight based on the total weight of the emission layer.

According to an exemplary embodiment of the present specification, the light emitting layer includes a host material and a dopant material in a weight ratio of 1:99 to 99:1 in the host material.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Formula 2 as a host material of the emission layer, and the emission layer includes the host material and the dopant material in a weight ratio of 1:99 to 99:1.

In the exemplary embodiment of the present specification, the maximum emission wavelength of the dopant is 550 to 700 nm.

According to an exemplary embodiment of the present specification, the dopant is a phosphorescent dopant.

According to an exemplary embodiment of the present specification, the dopant is a fluorescent dopant.

According to an exemplary embodiment of the present specification, the dopant is a metal complex.

According to an exemplary embodiment of the present specification, the dopant is an iridium-based complex.

According to an exemplary embodiment of the present specification, the dopant may be selected from the following structures, but is not limited thereto.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except for including a hole transport layer and an emission layer.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppressing layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to such a 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.

The organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which two or more organic material layers are stacked.

In the exemplary embodiment of the present specification, the organic light emitting device may further include one layer or two or more layers selected from the group consisting of a hole injection layer, an electron transport layer, an electron injection layer, an electron suppression layer, and a hole blocking layer. .

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 2 and the organic material layer including the compound represented by Formula 2 contact each other.

In an exemplary embodiment of the present specification, the light-emitting layer including the compound represented by Formula 2 and the organic material layer including the compound represented by Formula 1 are in contact with each other, and the organic material layer including the compound represented by Formula 1 is a hole transport layer. to be.

In an exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 2 and the organic material layer including the compound represented by Formula 1 are in contact with each other, and the organic material layer including the compound represented by Formula 1 is electron-suppressed. Layer.

In an exemplary embodiment of the present specification, another organic material layer is provided between the emission layer including the compound represented by Formula 2 and the organic material layer including the compound represented by Formula 1.

In an exemplary embodiment of the present specification, another organic material layer is provided between the light emitting layer including the compound represented by Formula 2 and the organic material layer including the compound represented by Formula 1, and the other organic material layer is an electron suppressing layer.

For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1, but is not limited thereto.

In FIG. 1, an anode 201, an organic material layer 301 including a compound represented by Formula 1, an emission layer 401 including a compound represented by Formula 2, and a cathode 501 are sequentially stacked on a substrate 101 The structure of the organic light-emitting device is illustrated. 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

FIG. 2 illustrates a structure of an organic light emitting diode in which an anode 201, a hole transport layer 601, an electron suppression layer 701, a light emitting layer 401, and a cathode 501 are sequentially stacked on a substrate 101. The hole transport layer or the electron suppressing layer includes a compound represented by Formula 1, and the emission layer includes a compound represented by Formula 2.

3 illustrates the structure of an organic light emitting diode in which an anode 201, a hole transport and electron suppression layer 801, a light emitting layer 401, and a cathode 501 are sequentially stacked on a substrate 101. The hole transport and electron suppression layer includes a compound represented by Formula 1, and the emission layer includes a compound represented by Formula 2.

4, an anode 201, a hole transport layer 601, an electron suppression layer 701, a light emitting layer 401, a hole blocking layer 901, an electron injection and transport layer 900, and a cathode 501 on the substrate 101. The structure of the organic light-emitting device stacked sequentially is illustrated. The major transport layer or the electron-suppressing layer includes a compound represented by Chemical Formula 1, and the light emitting layer includes a compound represented by Chemical Formula 2.

5, an anode 201, a hole transport and electron suppression layer 801, a light emitting layer 401, a hole blocking layer 901, an electron injection and transport layer 900, and a cathode 501 are sequentially formed on the substrate 101. The structure of the stacked organic light emitting device is illustrated. The hole transport and electron suppression layer includes a compound represented by Formula 1, and the emission layer includes a compound represented by Formula 2. 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.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SNO2:Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) 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 hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, 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 emission layer, and may be a layer other than the organic material layer including Formula 1 of the present specification. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including 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 a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant material may be an organic compound, a metal or a metal compound.

Organic compounds as dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, and fluoranthene compounds. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted A compound in which at least one arylvinyl group is substituted on the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, a general metal or metal compound may be used as the metal or metal compound, and specifically, a metal complex may be used. Examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, 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, etc., but are not limited thereto.

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

In addition, the organic light emitting device according to the present specification may have a normal type in which a lower electrode is an anode and an upper electrode is a cathode, and may have an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.

The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

The core structure of the compound represented by Formulas 1 and 2 according to an exemplary embodiment of the present specification may be prepared through Reaction Schemes 1 and 2-1 to 2-7 as follows, but is not limited thereto.

[Scheme 1]

[Scheme 2-1]

[Reaction Scheme 2-2]

[Scheme 2-3]

[Scheme 2-4]

[Scheme 2-5]

[Scheme 2-6]

[Scheme 2-7]

In Reaction Scheme 1, R3, R4, Ar1, Ar2 and L1 are the same as defined in Formula 1,

In Reaction Schemes 2-1 to 2-7, the definitions of R10 to R19 and L2 are the same as those in Chemical Formula 2, and R20 and X are the same as those in Chemical Formula 3.

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

Preparation Example 1_Synthesis of Compound 1-1

After completely dissolving Compound A and Compound a1 in 220 mL of Xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, NaOtBu was added, bis (tri-tert-butylphosphine) palladium (0) was added, followed by heating and stirring for 4 hours. I did. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 1-1. MS[M+H] ⁺ = 718

Preparation Example 2_ Synthesis of Compound 1-2

After completely dissolving Compound B and Compound a2 in xylene in a round bottom flask in a nitrogen atmosphere, NaOtBu was added, bis (tri-tert-butylphosphine) palladium (0) (0.06 g, 0.12 mmol) was added, and then 3 Heated and stirred for hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 1-2.

MS[M+H] ⁺ = 718

Preparation Example 3_ Synthesis of Compound 1-3

After completely dissolving Compound A and Compound a3 in tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, 2M aqueous potassium carbonate solution was added, and tetrakis-(triphenylphosphine)palladium (0.66 g, 0.57 mmol) was added. After heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate to prepare compound 1-3.

MS[M+H] ⁺ = 794

Preparation Example 4_Synthesis of Compound 1-4

After completely dissolving compound C and compound a4) in xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu was added, bis(tri-tert-butylphosphine)palladium (0) was added, followed by heating and stirring for 3 hours. . After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 1-4. MS[M+H] ⁺ = 802

In addition, Compounds 2-1 to 2-4 may be prepared by appropriately controlling the substituents in Schemes 2-1 to 2-7, and may be prepared by a conventional method for preparing a red host.

Preparation Example 5_Synthesis of Compound 2-1

Compound D (7.29g, 27.32mmol), d1 (7.50g, 26.79mmol) was completely dissolved in 160ml of xylene in a nitrogen atmosphere, and sodium-tert-butoxide (3.86g, 40.18mmol) was added. Then, bis (tri-tert-butylphosphine) palladium (0) (0.14 g, 0.27 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 2-1 (9.75g, 71%). MS[M+H] ⁺ = 512

Preparation Example 6_Synthesis of Compound 2-2

Compound E (7.50g, 34.56mmol) and e1 (16.29g, 35.25mmol) were completely dissolved in 160ml of xylene in a nitrogen atmosphere, and sodium tert-butoxide (4.98g, 51.84mmol) was added thereto, and then, After adding bis(tri-tert-butylphosphine)palladium(0) (0.18g, 0.35mmol), the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 2-2 (12.67g, 57%).

MS[M+H]+= 644

Preparation Example 7_ Synthesis of Compound 2-3

Compound E (5.50g, 25.35mmol) and e2 (11.92g, 25.85mmol) were completely dissolved in 160ml of xylene in a nitrogen atmosphere, and sodum tert-butoxide (3.65g, 38.02mmol) was added thereto, and After adding bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.25 mmol), the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 2-3 (9.42g, 58%).

MS[M+H]+= 643

Preparation Example 8_Synthesis of Compound 2-4

Compound E (6.50g, 29.95mmol) and e2 (12.89g, 30.55mmol) were completely dissolved in 160ml of xylene in a nitrogen atmosphere, and sodium tert-butoxide (4.32g, 44.92mmol) was added thereto, and then After adding bis(tri-tert-butylphosphine)palladium(0) (0.15g, 0.30mmol), it was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate to prepare compound 2-4 (13.25g, 73%).

MS[M+H]+= 604

Comparative Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 Å, but the following compound A-1 was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, an electron suppressing layer was formed by vacuum depositing the following EB-1 compound with a film thickness of 150 Å on the hole transport layer. Subsequently, the following RH-1 compound and the following RD-1 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film to form a red light emitting layer having a thickness of 360 Å. A hole blocking layer was formed by vacuum depositing the following HB-1 compound with a thickness of 30 Å on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) at a thickness of 12 Å and aluminum at a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 ⁻ Maintaining ⁷ ~ 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

Experimental example 1-1 Experimental example 1-32

In the organic light-emitting device of Comparative Example 1-1, the organic light-emitting device was prepared in the same manner as in Comparative Example 1-1, except that the compounds shown in Table 1 below were used instead of HT-1, EB-1, and RH-1. Was prepared.

Experimental example 1-33 to Experimental example 1-36

In the organic light-emitting device of Comparative Example 1-1, except for forming a hole transport and electron-suppressing layer having a thickness of 950 Å using one compound of Table 1 instead of HT-1 and EB-1 by vacuum deposition. An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1.

Comparative example 1-2 to 1-9 and Comparative example 1-14 to 1-17

In the organic light-emitting device of Comparative Example 1-1, the organic light-emitting device was prepared in the same manner as in Comparative Example 1-1, except that the compounds shown in Table 1 below were used instead of HT-1, EB-1, and RH-1. Was prepared.

Comparative example 10 to Comparative example 13

In the organic light-emitting device of Comparative Example 1-1, except for forming a hole transport and electron-suppressing layer having a thickness of 950 Å using one compound of Table 1 instead of HT-1 and EB-1 by vacuum deposition. An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1.

Experimental example

When a current was applied to the organic light emitting devices prepared in Experimental Examples 1-1 to 1-36 and Comparative Examples 1-1 to 1-17, voltage, efficiency, color coordinates, and lifetime were measured, and the result It is shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (5000 nit) to 95%.

Host
(Red) Electronic
Suppression layer Precision
Transport layer Voltage
(V) Luminance
(cd/m2) CIEx
CIEy T95
(hr) Comparative Example 1-1 RH-1 EB-1 HT-1 4.82 5.81 0.662 0.310 285 Comparative Example 1-2 RH-1 1-1 HT-1 4.63 6.23 0.674 0.315 365 Comparative Example 1-3 RH-1 1-2 HT-1 4.65 6.34 0.672 0.317 360 Comparative Example 1-4 RH-1 1-3 HT-1 4.66 6.25 0.673 0.315 365 Comparative Example 1-5 RH-1 1-4 HT-1 4.67 6.31 0.677 0.313 365 Comparative Example 1-6 RH-1 EB-1 1-1 4.19 6.17 0.679 0.319 340 Comparative Example 1-7 RH-1 EB-1 1-2 4.25 6.14 0.678 0.318 345 Comparative Example 1-8 RH-1 EB-1 1-3 4.27 6.11 0.666 0.319 355 Comparative Example 1-9 RH-1 EB-1 1-4 4.26 6.12 0.675 0.315 345 Comparative Example 1-10 RH-1 1-1 4.24 6.31 0.676 0.317 350 Comparative Example 1-11 RH-1 1-2 4.32 6.42 0.678 0.315 355 Comparative Example 1-12 RH-1 1-3 4.31 6.34 0.678 0.313 355 Comparative Example 1-13 RH-1 1-4 4.38 6.38 0.679 0.319 350 Comparative Example 1-14 2-1 EB-1 HT-1 4.33 6.37 0.677 0.318 435 Comparative Example 1-15 2-2 EB-1 HT-1 4.30 6.27 0.678 0.319 425 Comparative Example 1-16 2-3 EB-1 HT-1 4.28 6.22 0.679 0.315 450 Comparative Example 1-17 2-4 EB-1 HT-1 4.29 6.25 0.677 0.317 430 Experimental Example 1-1 2-1 1-1 HT-1 4.54 6.31 0.679 0.317 440 Experimental Example 1-2 2-1 1-2 HT-1 4.59 6.42 0.679 0.315 435 Experimental Example 1-3 2-1 1-3 HT-1 4.55 6.34 0.678 0.313 435 Experimental Example 1-4 2-1 1-4 HT-1 4.56 6.22 0.679 0.319 420 Experimental Example 1-5 2-2 1-1 HT-1 4.54 6.31 0.678 0.318 445 Experimental Example 1-6 2-2 1-2 HT-1 4.59 6.42 0.678 0.313 435 Experimental Example 1-7 2-2 1-3 HT-1 4.58 6.34 0.679 0.319 420 Experimental Example 1-8 2-2 1-4 HT-1 4.55 6.22 0.678 0.318 445 Experimental Example 1-9 2-3 1-1 HT-1 4.59 6.31 0.678 0.318 465 Experimental Example 1-10 2-3 1-2 HT-1 4.51 6.42 0.677 0.315 465 Experimental Example 1-11 2-3 1-3 HT-1 4.57 6.35 0.679 0.317 460 Experimental Example 1-12 2-3 1-4 HT-1 4.56 6.24 0.678 0.315 465 Experimental Example 1-13 2-4 1-1 HT-1 4.52 6.38 0.679 0.15 435 Experimental Example 1-14 2-4 1-2 HT-1 4.52 6.47 0.677 0.317 440 Experimental Example 1-15 2-4 1-3 HT-1 4.54 6.30 0.679 0.315 435 Experimental Example 1-16 2-4 1-4 HT-1 4.55 6.32 0.678 0.313 445 Experimental Example 1-17 2-1 EB-1 1-1 4.13 6.11 0.678 0.319 420 Experimental Example 1-18 2-1 EB-1 1-2 4.36 6.34 0.677 0.318 445 Experimental Example 1-19 2-1 EB-1 1-3 4.04 6.28 0.679 0.313 445 Experimental Example 1-20 2-1 EB-1 1-4 4.29 6.31 0.678 0.319 420 Experimental Example 1-21 2-2 EB-1 1-1 4.15 6.27 0.679 0.318 445 Experimental Example 1-22 2-2 EB-1 1-2 4.23 6.22 0.677 0.315 425 Experimental Example 1-23 2-2 EB-1 1-3 4.12 6.31 0.679 0.317 440 Experimental Example 1-24 2-2 EB-1 1-4 4.29 6.28 0.678 0.315 435 Experimental Example 1-25 2-3 EB-1 1-1 4.11 6.22 0.677 0.315 465 Experimental Example 1-26 2-3 EB-1 1-2 4.25 6.35 0.679 0.317 460 Experimental Example 1-27 2-3 EB-1 1-3 4.12 6.31 0.678 0.315 465 Experimental Example 1-28 2-3 EB-1 1-4 4.22 6.29 0.678 0.313 470 Experimental Example 1-29 2-4 EB-1 1-1 4.11 6.37 0.677 0.319 455 Experimental Example 1-30 2-4 EB-1 1-2 4.21 6.21 0.679 0.318 465 Experimental Example 1-31 2-4 EB-1 1-3 4.13 6.22 0.678 0.319 440 Experimental Example 1-32 2-4 EB-1 1-4 4.15 6.34 0.679 0.315 455 Experimental Example 1-33 2-3 1-1 4.12 6.03 0.677 0.315 500 Experimental Example 1-34 2-3 1-2 4.35 6.05 0.679 0.317 505 Experimental Example 1-35 2-3 1-3 4.32 6.01 0.678 0.315 515 Experimental Example 1-36 2-3 1-4 4.32 6.09 0.678 0.313 520

When a current was applied to the organic light-emitting devices fabricated in Examples 1-1 to 1-36 and Comparative Examples 1-1 to 1-17, the results of Table 1 were obtained. The red organic light-emitting device of Comparative Example 1-1 uses a material that has been widely used in the past, and has a structure using compound [EB-1] as an electron blocking layer and compounds RH-1/RD-1 as a red emission layer.

According to Table 1, in Comparative Examples 1-2 to 1-5, the compound represented by Formula 1 was used instead of EB-1, and in Comparative Examples 1-6 to 1-9, the compound represented by Formula 1 was used as HT-1. Instead, in Comparative Examples 1-10 to 1-13, the compound represented by Formula 1 was used as a layer instead of HT-1 and EB-1, and Comparative Examples 1-14 to 1-17 were compounds of Formula 2 Instead of RH-1, an organic light-emitting device including the compounds of Formula 1 and Formula 2 was manufactured.

When Formula 1 is used as a hole transport layer, the driving voltage decreases by 8-10%, and when used as an electron suppression layer, the efficiency increases by 5-7%. When used as a single layer, the characteristics of low voltage and high efficiency are simultaneously I got a visible result.

In addition, when the formula 2 was used as a red light emitting layer, the lifespan was increased by 40 to 60%.

In Experimental Examples 1-1 to 1-36, when the derivatives of Formula 1 were used as an electron suppressing layer or a hole transport layer, or as a single layer, and Formula 2 was used as a host of the red light emitting layer, the driving voltage and light emission of the organic light emitting device It can be seen that the efficiency and longevity characteristics can be improved.

In Experimental Examples 1-9 to 1-12 and 1-25 to 1-28, when 2-3 was used as the host of the light emitting layer, the longest life was obtained. In addition, in Experimental Examples 1-17, 1-21, 1-25, 1-29, and 1-33, when 1-1 was used as the hole transport layer, the driving voltage was the lowest. I got long results. In addition, in Experimental Examples 1-2, 1-6, 1-10, and 1-14, when Formula 1-2 was used as the electron suppressing layer, the luminous efficiency was highest.

Through this, the formula 1 of the present invention (a structure in which an amine is directly connected to a central core or a linker is included) is used as an electron-suppression layer or a hole-transport layer, or as one layer (hole-transport and electron-suppressive layer). And it can be seen that the driving voltage, luminous efficiency, and life characteristics of the red organic light-emitting device can be improved by combining Formula 2 (a structure in which a heterocyclic group including a 5-cyclic ring is connected to benzocarbazole) with a red light-emitting layer material. have.

101: substrate
201: anode
301: organic material layer containing the compound represented by Formula 1
401: light-emitting layer containing a compound represented by Chemical Formula 2
501: cathode
601: hole transport layer
701: electron suppression layer
801: hole transport and electron suppression layer
900: electron injection and transport layer
901: hole block

Claims (8)

anode; A negative electrode provided opposite to the positive electrode; And an organic material layer between the anode and the cathode,
The organic material layer includes a light emitting layer comprising a compound represented by the following formula (2),
An organic light-emitting device that is provided between the light-emitting layer and the anode and further comprises an organic material layer comprising a compound represented by the following Formula 1:
[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,
L1 is a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or heterocyclic group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m is an integer from 0 to 8, and when m is 2 or more, R1 is the same as or different from each other,
n is an integer from 0 to 7, and when n is 2 or more, R2 is the same as or different from each other,
R3 and R4 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
L2 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
Ar3 is a tricyclic or more heterocyclic group containing two substituted or unsubstituted N,
R10 to R19 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two groups adjacent to each other may be bonded to each other to form an aromatic hydrocarbon ring. The organic light-emitting device of claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The L1, Ar1, Ar2, R3 and R4 are as defined in Chemical Formula 1. The organic light-emitting device of claim 1, wherein Formula 2 is represented by any one of the following Formulas 2-1 to 2-7:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,
The L2 and Ar3 are as defined in Chemical Formula 2. The organic light-emitting device of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the following structural formulas:

In the above structural formula, a dotted line means a position bonded to N in Formula 1. The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylylene group; Quiterphenylylene group; Naphthylene group; Anthracenylene group; Dimethylfluorenylene group; A divalent phenanthren group; Divalent pyrene group; Or an organic light-emitting device that is a divalent triphenylene group. The organic light-emitting device of claim 1, wherein Ar3 is represented by the following Formula 3:
[Formula 3]

In Chemical Formula 3, the dotted line means a position bonded to L2,
X is S, O or C(R25)(R26),
R20 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 6, wherein R20 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted fluorenyl group; Or an organic light-emitting device that is a substituted or unsubstituted benzofluorenyl group. The organic light-emitting device of claim 1, wherein the emission layer further comprises a dopant compound having a maximum emission wavelength of 550 to 700 nm.

Images