WO2020091522A1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device comprising same.

Description

Compound and organic light emitting device comprising same

The present application relates to a compound and an organic light emitting device comprising the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0133609 filed with the Korean Intellectual Property Office on November 2, 2018, the entire contents of which are incorporated herein.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including a first electrode, a second electrode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, 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. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected in the first electrode and electrons are injected into the organic material layer in the second electrode, and excitons are formed when the injected holes meet the electrons. , When this exciton falls back to ground, it glows.

The development of new materials for such organic light-emitting devices continues to be required.

The present application is to provide a compound and an organic light emitting device comprising the same.

The present application provides a compound represented by Formula 1 below.

[Formula 1]

X1 is NR, X2 is a direct bond; Or X1 is a direct bond, X2 is NR,

A is benzene,

R is represented by the following formula (2),

[Formula 2]

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar is any one selected from the following structural formulae,

R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

x is an integer from 0 to 5,

y is an integer from 0 to 7,

When x or y is 2 or more, the substituents in parentheses are the same or different from each other,

a is 1 or 2,

When a is 2, the substituents in parentheses are the same as or different from each other.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer provides an organic light emitting device comprising the above-described compound.

The organic light emitting device using the compound according to an exemplary embodiment of the present application may have a low driving voltage, high luminous efficiency, or long life.

1 shows an example of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked.

2, the substrate 1, the first electrode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, the electron transport layer 7 and the second electrode 4 are sequentially stacked An example of an organic light emitting device is shown.

3 shows a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 8, a light emitting layer 3, a hole blocking layer 9, electron injection and An example of an organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated.

[Description of codes]

1: Substrate

2: first electrode

3: light emitting layer

4: Second electrode

5: hole injection layer

6: hole transport layer

7: electron transport layer

8: Electronic restraint layer

9: Hole bottom layer

10: electron injection and transport layer

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

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

According to the exemplary embodiment of the present application, the compound represented by Chemical Formula 1 has an advantage of controlling triplet energy by having the core structure as described above, and may exhibit characteristics of long life and high efficiency.

Examples of the substituent in this specification are described below, but are not limited thereto.

The term "substitution" 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 to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" 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 straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 50. Specific examples are 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 is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 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 is not limited thereto. Does not.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be, but is not limited to this.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but 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 preferable that it has 10 to 24 carbon atoms. 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 combine with each other to form a ring.

,

,

및

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

,

,

And

And the like, but is not limited thereto.

In the present specification, the heteroaryl group includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, and the like, but are not limited thereto.

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

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

According to an exemplary embodiment of the present application, X1 is NR, X2 is a direct bond; Or X1 is a direct bond and X2 is NR. That is, both X1 and X2 are direct bonds, or both X1 and X2 are not NR, one of X1 and X2 is a direct bond, and the other is NR.

According to an exemplary embodiment of the present application, A is a benzene ring.

According to an exemplary embodiment of the present application, R is represented by the following formula (2).

[Formula 2]

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; It is an arylene group of 6 to 20 carbon atoms unsubstituted or substituted with an aryl group of 6 to 20 carbon atoms.

According to an exemplary embodiment of the present application, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted biphenylylene group.

According to an exemplary embodiment of the present application, L is a direct bond; A phenylene group unsubstituted or substituted with an aryl group; A naphthylene group unsubstituted or substituted with an aryl group; Or a biphenylylene group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present application, L is a direct bond; A phenylene group unsubstituted or substituted with a phenyl group; A naphthylene group unsubstituted or substituted with a phenyl group; Or a biphenylylene group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a heteroaryl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; An aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a tricyclic ring heteroaryl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to an exemplary embodiment of the present application, "substituted or unsubstituted" of R 'means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups.

According to an exemplary embodiment of the present application, "substituted or unsubstituted" of R 'means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, methyl group, and phenyl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A naphthyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A terphenyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Triphenylene group unsubstituted or substituted with deuterium, alkyl group, or aryl group; A dibenzofuran group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A dibenzothiophene group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; Or a carbazole group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A naphthyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A terphenyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Triphenylene group unsubstituted or substituted with deuterium, alkyl group, or aryl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Naphthyl group unsubstituted or substituted with deuterium, methyl group, or phenyl group; A biphenyl group unsubstituted or substituted with deuterium, methyl group, or phenyl group; A terphenyl group unsubstituted or substituted with a deuterium, methyl group, or phenyl group; Phenanthrene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Fluorene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Triphenylene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present application, R 'is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium; Deuterium, or a naphthyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with deuterium; A terphenyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A triphenylene group unsubstituted or substituted with deuterium; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to one embodiment of the present application, x is an integer from 0 to 5, y is an integer from 0 to 7, and when x or y is 2 or more, substituents in parentheses are the same or different.

According to an exemplary embodiment of the present application, x and y is 1.

According to an exemplary embodiment of the present application, the a is 1 or 2; When a is 2, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.

In the above structural formula, R '' is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

x1 is an integer from 0 to 4,

y1 is an integer from 0 to 6,

When x or y is 2 or more, the substituents in parentheses are the same or different from each other,

Ra is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present application, R "is hydrogen or deuterium.

According to an exemplary embodiment of the present application, the Ra is an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a heteroaryl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, the Ra is an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a tricyclic ring heteroaryl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, the Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to an exemplary embodiment of the present application, the "substituted or unsubstituted" of Ra means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups.

According to an exemplary embodiment of the present application, the "substituted or unsubstituted" of Ra means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, methyl group, and phenyl group.

According to an exemplary embodiment of the present application, Ra is a phenyl group unsubstituted or substituted with a deuterium, an alkyl group, or an aryl group; A naphthyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A terphenyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Triphenylene group unsubstituted or substituted with deuterium, alkyl group, or aryl group; A dibenzofuran group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A dibenzothiophene group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; Or a carbazole group unsubstituted or substituted with a deuterium, alkyl group, or aryl group.

According to an exemplary embodiment of the present application, the Ra is deuterium; A phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A naphthyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A terphenyl group unsubstituted or substituted with a deuterium, alkyl group, or aryl group; A phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Triphenylene group unsubstituted or substituted with deuterium, alkyl group, or aryl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present application, the Ra is a deuterium, methyl group, or a phenyl group unsubstituted or substituted with a phenyl group; Naphthyl group unsubstituted or substituted with deuterium, methyl group, or phenyl group; A biphenyl group unsubstituted or substituted with deuterium, methyl group, or phenyl group; A terphenyl group unsubstituted or substituted with a deuterium, methyl group, or phenyl group; Phenanthrene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Fluorene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Triphenylene group unsubstituted or substituted with deuterium, methyl group, or phenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present application, Ra is a phenyl group unsubstituted or substituted with deuterium; Deuterium, or a naphthyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with deuterium; A terphenyl group unsubstituted or substituted with deuterium; A phenanthrene group unsubstituted or substituted with deuterium; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A triphenylene group unsubstituted or substituted with deuterium; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.

Ra of the above structural formula is as described above.

According to an exemplary embodiment of the present application, the formula 1 is represented by the following formula 1-1.

[Formula 1-1]

In Chemical Formula 1-1,

R is as defined above.

According to an exemplary embodiment of the present application, the formula 1 is represented by the following formula 1-2.

[Formula 1-2]

In Chemical Formula 1-2,

R is as defined above.

Further, according to an exemplary embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following structural formulas.

In addition, the present specification provides an organic light emitting device comprising the above-described compound.

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

When a member is referred to as being “on” another member in the present specification, this includes not only the case where one member abuts another member, but also another member between the two members.

In the present specification, when a part “includes” a certain component, this means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppressing layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In one embodiment of the present specification, 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.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.

In one embodiment of the present specification, the compound is included as a host of the light emitting layer.

In one embodiment of the present specification, the compound is included as a red host in the light emitting layer.

In one embodiment of the present specification, the light emitting layer further includes a dopant.

In one embodiment of the present specification, the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and may include other organic compounds, metals, or metal compounds as dopants.

In one embodiment of the present specification, the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and may include an iridium-based dopant.

In an exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and may include a phosphorescent dopant.

In an exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and may include a red or green phosphorescent dopant.

In an exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and may include an iridium-based phosphorescent dopant.

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

According to the exemplary embodiment of the present specification, the light emitting layer includes the compound and the dopant in a weight ratio of 2: 1 to 99: 1.

In one embodiment of the present specification, the iridium-based dopant may be selected from the following structures, but is not limited thereto.

In one embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound.

In one embodiment of the present specification, the organic material layer may include a hole injection layer, a hole transport layer, or an electron suppressing layer.

In one embodiment of the present specification, the organic material layer may include a hole injection layer, a hole transport layer, and an electron suppressing layer.

In one embodiment of the present specification, the organic layer is a hole blocking layer; Or it may include an electron injection and transport layer.

In one embodiment of the present specification, the organic layer is a hole blocking layer; And an electron injection and transport layer.

In one embodiment of the present specification, the organic light emitting device is a layer 1 or 2 selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, an electron suppressing layer and a hole blocking layer It contains more layers.

In one embodiment of the present application, the organic light emitting device includes 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. It includes two 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, and at least one of the two or more organic material layers comprises the compound. In an exemplary embodiment of the present application, 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 one 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 contains 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, or may be included in each of the two or more electron transport layers.

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

In one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer comprising a compound containing an arylamino group, a carbazole group, or a benzocarbazole group in addition to the organic material layer containing the compound.

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

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a second electrode, one or more organic material layers, and a first electrode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked. In this structure, the compound may be included in the light emitting layer (3).

2, the substrate 1, the first electrode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, the electron transport layer 7 and the second electrode 4 are sequentially stacked The structure of the organic light emitting element is illustrated. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

3 shows a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 8, a light emitting layer 3, a hole blocking layer 9, electron injection and Structural history of the organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated, and the compound may be included in the light emitting layer 3, but is not limited thereto.

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

The organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, 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.

 The organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1.

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

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to this method, an organic light emitting device may be made by sequentially depositing an organic material layer and a first electrode material from a second electrode 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 specification, 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 first electrode material, a material having a large work function is preferably used to facilitate hole injection into the organic material layer. Specific examples of the first electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the second electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, and thus has a hole injection effect in the first electrode, an excellent hole injection effect for a light emitting layer or a light emitting material, and a light emitting layer A compound that prevents migration of the excitons generated in the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first 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 matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

In one embodiment of the present application, the organic material layer includes a hole injection layer, and the hole injection layer is p-doped.

In one embodiment of the present application, the organic material layer includes a hole injection layer, and the hole injection layer is p-doped.

In one embodiment of the present specification, the hole injection layer further includes a p-doped material.

In the present specification, the p-doped material means a material that makes the host material have p-semiconductor properties. The p-semiconductor property refers to a property in which holes are injected or transported at a HOMO (highest occupied molecular orbital) energy level, that is, a property of a material having a large hole conductivity. As a layer for transporting, as a hole transporting material, a material capable of receiving holes from a first electrode or a hole injection layer and transporting holes to a light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. 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 compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the second electrode and transferring them to the light emitting layer, which has high mobility for electrons The material is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; 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 those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

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 second electrode, an excellent electron injection effect on the light emitting layer or the light emitting material, and excitons generated in the light emitting layer A compound that prevents migration to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that blocks the arrival of the second electrode 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 complex, and the like, but are not limited thereto.

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

The method of manufacturing the compound of Formula 1 and the production of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

The compounds of the present invention were prepared using Buchwald-Hartwig coupling reaction, Suzuki coupling reaction, Heck coupling reaction, and the like as representative reactions.

Preparation Example 1.

10-0.0g (1.0 eq) of 1-bromotriphenylene, 60.04 g (1.1 eq) of (2-nitrophenyl) boronic acid was dissolved in 1000 ml of tetrahydrofuran (THF), followed by 90.33 g of K ₂ CO _{3 in} 300 ml of water ( 2.0 eq). Pd ( t -Bu ₃ P) ₂ 1.59 g (0.005 eq) was added and refluxed and stirred. When the reaction was completed, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent, and subjected to column chromatography to obtain 84.42 g of Compound A-1, yield 74%). [M + H] ⁺ = 350

Formula A-1 84.42 g (1.0 eq) was added to 200 mL of triethylphosphite and stirred under reflux. After 2 hours, the reaction was terminated and the reaction was poured into 2 L of ethanol to drop a solid. The solid was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and the solution was concentrated under reduced pressure and purified by column chromatography. Compound A 48.31 g, yield 63%) was obtained. [M + H] ⁺ = 318

Preparation Example 2.

100.0 g (1.0 eq) of 2-chloroaniline and 240.9 g (1.1 eq) of 1-bromotriphenylene were dissolved in 1000 ml of toluene and 151.33 g (2.0 eq) of NaOtBu was added together. Pd ( t -Bu ₃ P) ₂ 4.02 g (0.01 eq) was added and refluxed and stirred. When the reaction was completed, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent, and subjected to column chromatography to obtain 205.71 g of Compound B-1 (yield: 74%). [M + H] ⁺ = 354

After dissolving 205.0 g (1.0 eq) of Compound B-1 in 1000 ml of dimethylacetamide (DMAc), add K ₃ PO ₄ 247.33 g (2.0 eq), Pd ( t -Bu ₃ P) ₂ 2.97 g (0.01 eq) It was stirred at reflux. After the reaction was completed, it was cooled, poured into water, stirred and solidified, and filtered. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent, and subjected to column chromatography to obtain Compound B 136.7 g, yield 74%). [M + H] ⁺ = 318

< Synthetic example >

Synthetic example  One

Compound A 10.0 g (1.0 eq), 3-([1,1'-biphenyl] -4-yl) -2-chlorobenzene [4,5] thieno [2,3-b] pyrazine 12.90 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 1 (15.03 g, yield 73%). [M + H] ⁺ = 654

Synthetic example  2

Compound A 10.0 g (1.0 eq), 3-chloro-2- (9-phenyl-9H-carbazol-2-yl) benzo [4,5] thieno [2,3-b] pyrazine 15.99 g (1.1 eq ), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 2 (16.38 g, yield 70%). [M + H] ⁺ = 743

Synthetic example  3

Compound A 10.0 g (1.0 eq), 2- (9H-carbazole-9-yl) -3-chlorobenzofuro [2,3-b] pyrazine 12.80 g (1.1 eq), Pd (t-Bu ₃ P ) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 3 (13.12 g, yield 64%). [M + H] ⁺ = 651

Synthetic example  4

Compound A 10.0 g (1.0 eq), 3-([1,1'-biphenyl] -3-yl) -2-chloro-9,9-dimethyl-9H-indeno [1,2-b] pyrazine 13.25 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 4 (12.75 g, yield 61%). [M + H] ⁺ = 664

Synthetic example  5

Compound A 10.0 g (1.0 eq), 2-chloro-9,9-dimethyl-3- (9-phenyl-9H-carbazol-4-yl) -9H-indeno [1,2-b] pyrazine 16.34 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 5 (14.94 g, yield 63%). [M + H] ⁺ = 753

Synthetic example  6

Compound A 10.0 g (1.0 eq), 2-chloro-4- (dibenzo [b, d] thiophen-1-yl) benzo [h] quinazolin 13.73 g (1.1 eq), Pd (t-Bu ₃ P ) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 6 (13.02 g, yield 61%). [M + H] ⁺ = 678

Synthetic example  7

Compound A 10.0 g (1.0 eq), 3-chloro-1- (phenanthren-2-yl) benzo [f] quinazolin 13.53 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq ), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 7 (13.75 g, yield 65%). [M + H] ⁺ = 672

Synthetic example  8

Compound A 10.0 g (1.0 eq), 3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -1-chlorobenzo [f] quinazoline 15.33 g (1.1 eq) , Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 8 (13.91 g, yield 61%). [M + H] ⁺ = 724

Synthetic example  9

Compound A 10.0 g (1.0 eq), 2-chloro-3- (naphthalen-1-yl) benzo [f] quinoxaline 11.79 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq) , K ₃ PO ₄ 13.39 g (2.0 eq) was put in 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 9 (13.12 g, yield 67%). [M + H] ⁺ = 622

Synthetic example  10

Compound A 10.0 g (1.0 eq), 2-([1,1 ': 4', 1 ''-terphenyl] -4-yl) -3-chlorobenzo [f] quinoxaline 15.33 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 10 (14.14 g, yield 62%). [M + H] ⁺ = 724

Synthetic example  11

Compound A 10.0 g (1.0 eq), 2-chloro-3- (4-phenylnaphthalen-1-yl) quinoxaline 12.69 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq) , K ₃ PO ₄ 13.39 g (2.0 eq) was put in 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 11 (13.87 g, yield 68%). [M + H] ⁺ = 648

Synthetic example  12

Compound A 10.0 g (1.0 eq), 2-([1,1'-biphenyl] -4-yl) -3- (3'-bromo- [1,1'-biphenyl] -4-yl) Benzo [4,5] thieno [2,3-b] pyrazine 19.70 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) with xylene 250ml It was put in and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 12 (18.02 g, yield 71%). [M + H] ⁺ = 806

Synthetic example  13

Compound A 10.0 g (1.0 eq), 2- (2-bromophenyl) -3- (dibenzo [b, d] furan-1-yl) benzo [4,5] thieno [2,3-b] Pyrazine 17.55 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and stirred under reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 13 (14.45 g, yield 67%). [M + H] ⁺ = 744

Synthetic example  14

Compound A 10.0 g (1.0 eq), 3- (5-bromo- [1,1'-biphenyl] -2-yl) -2- (naphthalen-1-yl) benzofuro [2,3-b ] Pyrazine 18.24 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 14 (17.81 g, yield 74%). [M + H] ⁺ = 764

Synthetic example  15

Compound A 10.0 g (1.0 eq), 4- (4-bromonaphthalen-1-yl) -2- (triphenylen-2-yl) benzo [h] quinazolin 21.16 g (1.1 eq), Pd (t -Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 15 (17.90 g, yield 67%). [M + H] ⁺ = 848

Synthetic example  16

Compound A 10.0 g (1.0 eq), 2- (4-bromonaphthalen-2-yl) -4- (dibenzo [b, d] thiophen-1-yl) benzo [h] quinazolin 19.63 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 16 (15.45 g, yield 61%). [M + H] ⁺ = 804

Synthetic example  17

Compound A 10.0 g (1.0 eq), 2- (2-bromophenyl) -3- (4-phenylnaphthalen-1-yl) quinoxaline 16.86 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 17 (13.00 g, yield 57%). [M + H] ⁺ = 724

Synthetic example  18

Compound B 10.0 g (1.0 eq), 2-chloro-3- (naphthalen-2-yl) benzofuro [2,3-b] pyrazine 11.44 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 18 (11.75 g, yield 61%). [M + H] ⁺ = 612

Synthetic example  19

Compound B 10.0 g (1.0 eq), 3-chloro-2- (dibenzo [b, d] furan-3-yl) -9,9-dimethyl-9H-indeno [1,2-b] pyrazine 13.73 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 19 (12.17 g, yield 57%). [M + H] ⁺ = 678

Synthetic example  20

Compound B 10.0 g (1.0 eq), 3-chloro-9,9-dimethyl-2-phenyl-9H-indeno [1,2-b] pyrazine 10.61 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 20 10.92 g, yield 59%). [M + H] ⁺ = 588

Synthetic example  21

Compound B 10.0 g (1.0 eq), 3- (9H-carbazole-9-yl) -1-chlorobenzo [f] quinazolin 13.14 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g ( 0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 21 (11.24 g, yield 54%). [M + H] ⁺ = 661

Synthetic example  22

Compound B 10.0 g (1.0 eq), 3-chloro-2- (naphthalen-2-yl) benzo [f] quinoxaline 11.79 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq) , K ₃ PO ₄ 13.39 g (2.0 eq) was put in 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 22 (11.16 g, yield 57%). [M + H] = 622

Synthetic example  23

Compound B 10.0 g (1.0 eq), 2-chloro-3- (phenyl-d5) quinoxaline 8.50 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq) was added to 250 ml of xylene and stirred under reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 23 (11.11 g, yield 67%). [M + H] ⁺ = 527

Synthetic example  24

Compound B 10.0 g (1.0 eq), 2-chloro-3-phenylquinoxaline 8.32 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), K ₃ PO ₄ 13.39 g (2.0 eq ) Was put into 250 ml of xylene and stirred under reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 24 (11.34 g, yield 69%). [M + H] ⁺ = 522

Synthetic example  25

Compound B 10.0 g (1.0 eq), 2- (4'-bromo- [1,1'-biphenyl] -4-yl) -3- (4- (naphthalen-2-yl) phenyl) quinoxaline 19.49 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 25 (17.64 g, yield 70%). [M + H] ⁺ = 800

Synthetic example  26

Compound B 10.0 g (1.0 eq), 3- (4-bromonaphthalen-1-yl) -2- (dibenzo [b, d] furan-3-yl) benzo [4,5] thieno [2, 3-b] Pyrazine 19.28 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and stirred at reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 26 (18.00 g, 72% yield). [M + H] ⁺ = 794

Synthetic example  27

Compound B 10.0 g (1.0 eq), 3- (3-bromophenyl) -2- (dibenzo [b, d] thiophen-3-yl) benzo [4,5] thieno [2,3-b ] Pyrazine 18.10 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 27 (16.03 g, yield 67%). [M + H] ⁺ = 760

Synthetic example  28

Compound B 10.0 g (1.0 eq), 3- (4-bromonaphthalen-1-yl) -2- (phenanthren-2-yl) benzofuro [2,3-b] pyrazine 19.08 g (1.1 eq) , Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 28 (15.88 g, yield 64%). [M + H] ⁺ = 788

Synthetic example  29

Compound B 10.0 g (1.0 eq), 3- (3-bromophenyl) -2- (triphenylen-2-yl) benzofuro [2,3-b] pyrazine 19.08 g (1.1 eq), Pd ( t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 29 (17.62 g, yield 71%). [M + H] ⁺ = 788

Synthetic example  30

Compound B 10.0 g (1.0 eq), 3-([1,1'-biphenyl] -4-yl) -2- (4-bromophenyl) benzo [4,5] thieno [2,3-b ] Pyrazine 17.06 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was added to 250 ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove the solvent by 50%. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining Compound 30 (17.01 g, yield 74%). [M + H] ⁺ = 730

< Experimental example >

Comparative example  One

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150Å, but the following A-1 compound 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 mm 2. Subsequently, the following EB-1 compound was vacuum-deposited to a thickness of 150 mm 2 on the hole transport layer to form an electron suppressing layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98: 2 on the EB-1 deposition film to form a 400-nm-thick red light emitting layer. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound with a thickness of 30 mm 2 on the light emitting layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer in a weight ratio of 2: 1 to form an electron injection and transport layer with a thickness of 300 Pa. On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 순차적 were sequentially deposited to form a negative electrode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- An} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ^-6 torr.

Example  1 to Example  30

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound shown in Table 1 instead of RH-1 in the organic light emitting diode of Comparative Example 1.

Comparative example  2 to Comparative example  21

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound shown in Table 1 instead of RH-1 in the organic light emitting diode of Comparative Example 1.

[Comparative Example Compound]

When current was applied to the organic light emitting devices manufactured in Examples 1 to 30 and Comparative Examples 1 to 21, voltage, efficiency, and lifetime were measured and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (10,000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd / A) Life T95 (hr) Emission color Comparative Example 1 RH-1 4.46 35.7 163 Red Example 1 Compound 1 3.93 47.2 310 Red Example 2 Compound 2 3.98 46.1 287 Red Example 3 Compound 3 4.00 42.8 267 Red Example 4 Compound 4 4.10 39.1 224 Red Example 5 Compound 5 4.13 38.8 211 Red Example 6 Compound 6 4.01 42.9 233 Red Example 7 Compound 7 4.03 44.5 271 Red Example 8 Compound 8 4.09 42.1 253 Red Example 9 Compound 9 4.05 45.9 295 Red Example 10 Compound 10 4.12 42.3 287 Red Example 11 Compound 11 3.90 51.7 305 Red Example 12 Compound 12 4.11 38.5 224 Red Example 13 Compound 13 3.97 45.4 209 Red Example 14 Compound 14 3.99 43.5 265 Red Example 15 Compound 15 4.10 44.1 249 Red Example 16 Compound 16 4.16 42.5 233 Red Example 17 Compound 17 3.94 48.3 209 Red Example 18 Compound 18 3.97 46.4 281 Red Example 19 Compound 19 4.05 40.2 290 Red Example 20 Compound 20 4.09 39.1 267 Red Example 21 Compound 21 4.11 38.7 241 Red Example 22 Compound 22 4.01 39.5 194 Red Example 23 Compound 23 3.87 50.4 337 Red Example 24 Compound 24 3.85 50.8 281 Red Example 25 Compound 25 4.17 39.1 199 Red Example 26 Compound 26 4.27 38.6 223 Red Example 27 Compound 27 4.19 39.3 189 Red Example 28 Compound 28 4.11 40.5 241 Red Example 29 Compound 29 4.20 39.7 181 Red Example 30 Compound 30 4.02 43.0 257 Red Comparative Example 2 C-1 5.01 18.7 17 Red Comparative Example 3 C-2 5.05 18.9 25 Red Comparative Example 4 C-3 5.03 19.6 23 Red Comparative Example 5 C-4 4.98 17.3 15 Red Comparative Example 6 C-5 4.95 16.8 28 Red Comparative Example 7 C-6 4.98 18.5 21 Red Comparative Example 8 C-7 5.01 17.8 23 Red Comparative Example 9 C-8 5.07 38.4 18 Red Comparative Example 10 C-9 4.20 37.9 152 Red Comparative Example 11 C-10 4.45 33.5 221 Red Comparative Example 12 C-11 4.28 31.7 182 Red Comparative Example 13 C-12 4.23 34.5 199 Red Comparative Example 14 C-13 4.70 33.5 210 Red Comparative Example 15 C-14 4.96 32.8 118 Red Comparative Example 16 C-15 4.43 32.1 230 Red Comparative Example 17 C-16 4.37 33.1 165 Red Comparative Example 18 C-17 4.31 34.7 163 Red Comparative Example 19 C-18 4.39 31.5 205 Red Comparative Example 20 C-19 4.52 33.9 125 Red Comparative Example 21 C-20 4.39 33.5 141 Red

In the red organic light emitting device of Comparative Example 1, a material widely used in the related art was used. In Comparative Examples 2 to 21, organic light emitting devices were manufactured using C-1 to C-20 instead of RH-1. Looking at the results of Table 1, when the compound of the present invention was used as a host for a red light emitting layer, the driving voltage was significantly lowered by 20% compared to the comparative example material, and the efficiency was also increased by 20% or more. It was found that the energy transfer to the red dopant was well achieved. In addition, it was confirmed that while maintaining high efficiency, the lifespan characteristics were greatly improved over 1.5 times. In the end, the compounds of the present invention do not satisfy the structure of Formula 1 of the present invention (Comparative Examples 10 to 15 and 21), or compounds of the present invention (Comparative Examples 2 to 21) do not satisfy the electrons and holes. It can be judged to be because the stability is high and the balance of electron and hole movement is well within the OLED Red device. In conclusion, it can be seen that when the compound of the present invention is used as a host of a red light emitting layer, it is possible to improve driving voltage, light emission efficiency, and life characteristics of an organic light emitting device.

Claims (9)

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

In Formula 1, X1 is NR, X2 is a direct bond; Or X1 is a direct bond, X2 is NR, A is benzene, R is represented by the following formula (2), [Formula 2]

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, Ar is any one selected from the following structural formulae,

R 'is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, x is an integer from 0 to 5, y is an integer from 0 to 7, When x or y is 2 or more, the substituents in parentheses are the same or different from each other, a is 1 or 2; When a is 2, the substituents in parentheses are the same as or different from each other. The method according to claim 1, Chemical Formula 1 is a compound represented by the following Chemical Formula 1-1: [Formula 1-1]

In Chemical Formula 1-1, R is as defined in claim 1. The method according to claim 1, Formula 1 is a compound represented by the following Formula 1-2: [Formula 1-2]

In Chemical Formula 1-2, R is as defined in claim 1. The method according to claim 1, The compound represented by Formula 1 is a compound selected from the following compounds:

. A first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, At least one layer of the organic material layer is an organic light-emitting device comprising a compound according to any one of claims 1 to 4. The method according to claim 5, The organic layer includes a light emitting layer, The light emitting layer is an organic light emitting device comprising the compound. The method according to claim 5, The organic layer includes a hole injection layer or a hole transport layer, The hole injection layer or the hole transport layer is an organic light emitting device comprising the compound. The method according to claim 5, The organic material layer includes an electron transport layer or an electron injection layer, The electron transport layer or the electron injection layer is an organic light emitting device comprising the compound. The method according to claim 5, The organic light emitting device further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, an electron suppression layer and a hole blocking layer Light emitting element.

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