KR20200050893A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device comprising the same. The compound according to an embodiment of the present specification can be used in the organic light emitting device, to lower a driving voltage and improve light efficiency of the organic light emitting device.

Description

A compound and an organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0133636 filed with the Korean Intellectual Property Office on November 02, 2018, all of which is included in this specification.

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 an anode and a cathode 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, or the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

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

International Patent Application Publication No. 2003-012890

The present specification is intended to provide a compound and an organic light emitting device including the same.

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

In Chemical Formula 1,

* Is a position condensed with * in Chemical Formula 1-1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; Or deuterium,

a1 is an integer from 0 to 8, and when a1 is 2 or more, R1 is the same as or different from each other,

a2 is an integer from 0 to 2, and when a2 is 2, R2 is the same or different from each other,

In Chemical Formula 1-1,

X1 to X3 are the same as or different from each other, and each independently N; Or CH, and 2 or more of X1 to X3 are N,

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 heteroaryl group,

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

R3 is hydrogen; Or deuterium,

a3 is an integer of 0 to 6, and when a3 is 2 or more, R3 is the same or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

The compound according to one embodiment of the present specification is used in an organic light emitting device, so that the driving voltage of the organic light emitting device can be lowered, and light efficiency can be improved. In addition, the lifespan characteristics of the small intestine can be improved by the thermal stability of the compound.

1 to 3 show an example 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.

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

In the compound represented by Chemical Formula 1, a pyrimidine / triazine substituted with an aryl group / heteroaryl group is connected to a core structure in which benzoindol groups are condensed on carbons 1 and 2 of the triphenylene group. When the compound of Formula 1 is used as a host for a light emitting layer, stability to electrons and holes is high, and the balance of electrons and holes can be well balanced, thereby improving the voltage, luminous efficiency, and lifetime of the device.

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

는 연결되는 부위를 의미한다.In this specification,

Means the site to be connected.

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" as used herein refers to deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine group; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups containing one or more of N, O, and S atoms, or substituted with a substituent connected by two or more of the exemplified substituents, or have no substituents. It means not.

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 the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1- Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl Propyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3 , 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, and the like, 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 is 10-50 carbon atoms, and 10-30 is more preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, 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.

When the fluorenyl group is substituted, the substituent of carbon 9 may form a ring to form a spiro structure. Spirobifluorenyl group and the like, but is not limited thereto.

In the present specification, the heteroaryl group is a heteroatom containing at least one of N, O, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 carbon atoms. Do. Examples of the heteroaryl group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyrido pyrimidine group, pyrido pyrimidine group pyrazine), pyrazino pyrazine, isoquinoline group, indole group, pyrido indole, indo pyrimidine, 5H-indeno pyrimidine, carbazole group, benzoxazole group, benzimidazole group , Benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group and Thiadiazolyl groups, and the like, but are not limited to these.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.

In the present specification, the heterocycle is a non-carbon atom, and contains one or more heteroatoms. Specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In one embodiment of the present specification, * in Chemical Formula 1 is a position condensed with * in Chemical Formula 1-1.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, 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.

In one embodiment of the present specification, L is a direct bond; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 2 to 20 carbon atoms. The arylene group or heteroarylene group is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent carbazole group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; Or a substituted or unsubstituted divalent triazine group. In another exemplary embodiment, the 'substituted or unsubstituted' is an alkyl group having 1 to 5 carbon atoms; An aryl group having 6 to 20 carbon atoms; Or it is substituted or unsubstituted with a heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L is a direct bond; It is an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or nitrile groups.

In one embodiment of the present specification, L is a direct bond; It is an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with a nitrile group.

In one embodiment of the present specification, L is a direct bond; A phenylene group unsubstituted or substituted with a nitrile group; Biphenylene group; Or a naphthylene group.

In one embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group.

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

In one embodiment of the present specification, X1 to X3 are the same as or different from each other, and each independently N; Or CH, and 2 or more are N.

In one embodiment of the present specification, X1 and X2 are N, and X3 is CH.

In one embodiment of the present specification, X1 and X3 are N, and X2 is CH.

In one embodiment of the present specification, X2 and X3 are N, and X1 is CH.

In one embodiment of the present specification, X1 to X3 are N.

In one embodiment of the present specification, 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 heteroaryl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently 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.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. The aryl group or heteroaryl group is substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

In one 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 naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group. In another exemplary embodiment, the 'substituted or unsubstituted' is an alkyl group having 1 to 5 carbon atoms; An aryl group having 6 to 20 carbon atoms; Or it is substituted or unsubstituted with a heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or a methyl group; Or a heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Dimethylfluorenyl group; Dibenzofuran group; Dibenzothiophene group; N-phenylcarbazole group; Or a carbazole group, wherein Ar1 and Ar2 are substituted with deuterium or unsubstituted.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Dibenzofuran group; Dibenzothiophene group; N-phenylcarbazole group; Or a carbazole group, wherein Ar1 and Ar2 are substituted with deuterium or unsubstituted.

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

The structure is substituted or unsubstituted with deuterium,

In one embodiment of the present specification, Ar1 and Ar2 are different from each other.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Or deuterium.

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

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

In one embodiment of the present specification, a1 is an integer from 0 to 8, and when a1 is 2 or more, R1 is the same or different from each other.

In one embodiment of the present specification, a2 is an integer from 0 to 2, and when a2 is 2, R2 is the same or different from each other.

In one embodiment of the present specification, a3 is an integer from 0 to 6, and when a3 is 2 or more, R3 is the same or different from each other.

In one embodiment of the present specification, a1 to a3 are 0.

In one embodiment of the present specification, a1 is 8.

In one embodiment of the present specification, a2 is 2,

In one embodiment of the present specification, a3 is 6.

In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3-1 or 3-2.

[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2,

X1 to X3, Ar1, Ar2, L, R1 to R3 and a1 to a3 are defined as defined in Chemical Formula 1.

In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-6.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Chemical Formulas 2-1 to 2-6,

X1 to X3, Ar1, Ar2, L, R1 to R3 and a1 to a3 are defined as defined in Chemical Formula 1.

In one embodiment of the present specification, Chemical Formula 3-1 is represented by any one of Chemical Formulas 2-1 to 2-3.

In one embodiment of the present specification, Chemical Formula 3-2 is represented by any one of Chemical Formulas 2-4 to 2-6.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later. Representative examples are described in the manufacturing examples described below, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change starting materials, reactants, reaction conditions, and the like.

For example, the compound represented by Chemical Formula 1 may have a core structure as shown in General Formula 1 or 2 below. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art. Substituents may be bonded as in the following general formula 1 or 2, but are not limited thereto.

[Formula 1]

 [Formula 2]

After preparing the core structure according to the general formulas 1 and 2 as described above, the compounds of the present invention can be connected to a substituent using a Buchwald-Hartwig coupling reaction, Suzuki coupling reaction, Heck coupling reaction and the like.

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 an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

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

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, rather than excluding other components, unless otherwise specified.

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, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by Chemical Formula 1, and a light emitting layer including a compound represented by Chemical Formula 1 is red.

According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer is a compound represented by the formula (1); And dopants.

According to an exemplary embodiment of the present specification, the content of the dopant is 0.01 parts by weight to 20 parts by weight, more preferably 0.1 parts by weight to 10 parts by weight based on 100 parts by weight of the compound represented by Chemical Formula 1 above. In the above range, energy transfer from the host to the dopant occurs well.

According to an exemplary embodiment of the present specification, the emission wavelength of the dopant is not limited, and the dopant may be a phosphorescent dopant or a fluorescent dopant.

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

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

In one embodiment of the present specification, the organic material layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Chemical Formula 1. The light emitting layer including the compound represented by Chemical Formula 1 has a red color, and the light emitting layer not containing the compound represented by Chemical Formula 1 may include a blue, red or green light emitting compound known in the art.

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 the hole transport layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further includes at least one layer or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And 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 includes a compound represented by Chemical Formula 1.

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

In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 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 specification, when the compound represented by Chemical Formula 1 is included in each of the two or more electron transport layers, other materials except the compound represented by Chemical Formula 1 may be the same or different from each other. have.

When the organic material layer including the compound represented by Chemical Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may use those known in the art, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Chemical Formula 1 may further include LiQ (Lithium Quinolate).

In one embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in one layer of the two or more hole transport layers, or may be included in each of the two or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by Chemical Formula 1 is included in each of the two or more hole transport layers, other materials except the compound represented by Chemical Formula 1 may be the same or different from each other. have.

In one embodiment of the present specification, the organic material layer further comprises a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 It can contain.

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

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

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

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode 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 to 3. 1 to 3 illustrate an organic light emitting device and are not limited thereto.

1, a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101 is illustrated. The compound represented by Chemical Formula 1 is included in the light emitting layer.

2 illustrates a structure of an organic light emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 may be included in the light emitting layer, but is not limited thereto.

3, the anode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, the electron injection and transport layer on the substrate 101 ( 108) and the structure of the organic light emitting device in which the cathode 110 is sequentially stacked is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 may be included in the light emitting layer, but is not limited thereto.

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.

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

For example, the organic light emitting device of the present 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 positive electrode is deposited 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. It can be produced by forming 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 cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as 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 thereto.

In addition to this method, an organic light emitting device may also be formed by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. 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 cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. 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 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 dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having arylamine groups. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

In the present specification, when the compound represented by Chemical Formula 1 is included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and combined with holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxyquinoline aluminum complex (Alq3); 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; And rubrene, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.

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 well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex 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 negative electrode material, as used according to the prior art. Particularly, a suitable negative electrode material has a low work function and is a common material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

The electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents exciton generated in the light emitting layer from moving to the hole injection 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 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, and bis (8-hydroxyquinolinato) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. , But is not limited thereto.

The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.

The hole blocking layer is a layer that blocks reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, 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.

Hereinafter, examples and comparative examples will be described in detail to specifically describe the present specification. However, the examples and comparative examples according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the examples and comparative examples described below. The examples and comparative examples in the present specification are provided to more fully describe the present specification to those skilled in the art.

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.

2-nitronaphthalen-1-yl trifluoromethanesulfonate 100.0 g (1.0 eq), triphenylen-1-ylboronic acid 93.17 g (1.1 eq) was dissolved in 1000 ml of THF, and 86.05 g (2.0 eq) of K ₂ CO ₃ dissolved in 300 ml of water was added together. gave. 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 90.77 g of Compound A-1 (yield 73%). [M + H] = 400

Formula A-1 90.77g (1.0 eq) Triethylphosphite was added to 200 mL 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 53.44 g (yield 63%) was obtained. [M + H] = 218

Preparation Example 2.

In Preparation Example 1, instead of 2-nitronaphthalen-1-yl trifluoromethanesulfonate, 3-nitronaphthalen-2-yl trifluoromethanesulfonate was used to synthesize Formula B in the same manner as in Formula A.

Preparation Example 3.

In Preparation Example 1, instead of 2-nitronaphthalen-1-yl trifluoromethanesulfonate, 3-C- 1-nitronaphthalen-2-yl trifluoromethanesulfonate was used to synthesize Formula C in the same manner as in Formula A.

Preparation Example 4.

100.0 g (1.0 eq) of 1-chloronaphthalen-2-amine and 190.13 g (1.1 eq) of 1-bromotriphenylene were dissolved in 1000 ml of toluene, and then NaOtBu 108.58 g (2.0 eq) was added together. Pd ( t -Bu ₃ P) ₂ 2.88 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 152.56 g of Compound D-1 (yield 67%). [M + H] = 404

After dissolving 152.56 g (1.0 eq) of Compound D-1 in 1000 ml of DMAc, K ₃ PO ₄ 160.67 g (2.0 eq), Pd ( t -Bu ₃ P) ₂ 1.93 g (0.01 eq) was added and refluxed and stirred. 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. This was subjected to column chromatography, thereby obtaining Compound D 94.48 g (68% yield). [M + H] = 368

Preparation Example 5.

In Preparation Example 4, 3-chloronaphthalen-2-amine was used instead of 1-chloronaphthalen-2-amine to synthesize Formula E in the same manner as in Formula D.

Preparation Example 6.

In Preparation Example 4, instead of 1-chloronaphthalen-2-amine, 2-chloronaphthalen-1-amine was used to synthesize Formula F in the same manner as in Formula D.

<Synthesis example>

Synthesis Example 1

Compound A 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 8.00 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.22 g of a compound 1 (75% yield). [M + H] = 599

Synthesis Example 2

Compound A 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 10.69 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 13.30 g of compound 2 (yield 71%). [M + H] = 689

Synthesis Example 3

Compound B 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 9.49 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.88 g of a compound 3 (yield 73%). [M + H] = 649

Synthesis Example 4

Compound B 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.49 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 13.65 g of Compound 4 (yield 67%). [M + H] = 749

Synthesis Example 5

Compound B 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.97 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 15.19 g of Compound 5 (yield 73%). [M + H] = 765

Synthesis Example 6

Compound C 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.56 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.46 g of a compound 6 (yield 61%). [M + H] = 751

Synthesis Example 7

Compound C 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.67 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.94 g of Compound 7 (63% yield). [M + H] = 755

Synthesis Example 8

Compound C 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.94 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.68 g of a compound 8 (yield 61%). [M + H] = 764

Synthesis Example 9

Compound A 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 12.34 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.37 g of Compound 9 (65% yield). [M + H] = 700

Synthesis Example 10

Compound A 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 13.09 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.03 g of a compound 10 (yield 61%). [M + H] = 725

Synthesis Example 11

Compound A 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 13.24 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 13.30 g of compound 11 (yield 67%). [M + H] = 730

Synthesis Example 12

Compound C 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 14.29 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 13.32 g of compound 12 (yield 64%). [M + H] = 765

Synthesis Example 13

Compound D 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.55 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.26 g of a compound 13 (60% yield). [M + H] = 751

Synthesis Example 14

Compound D 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 12.94 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 13.09 g of compound 14 (63% yield). [M + H] = 764

Synthesis Example 15

Compound E 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 10.99 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 11.41 g of compound 15 (yield 60%). [M + H] = 699

Synthesis Example 16

Compound E 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 11.18 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 10.93 g of Compound 16 (yield 57%). [M + H] = 705

Synthesis Example 17

Compound E 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 11.32 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 10.62 g of Compound 17 (yield 55%). [M + H] = 710

Synthesis Example 18

Compound F 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 10.99 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.13 g (0.01 eq), K ₃ PO ₄ 11.56 g (2.0 eq) It 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 10.84 g of a compound 18 (yield 57%). [M + H] = 699

Synthesis Example 19

Compound D 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 12.34 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 9.71 g (Yield 51%) of Compound 19. [M + H] = 700

Synthesis Example 20

Compound D 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 19.59 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.69 g of a compound 20 (50% yield). [M + H] = 933

Synthesis Example 21

Compound E 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 17.05 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 15.86 g of a compound 21 (68% yield). [M + H] = 857

Synthesis Example 22

Compound E 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 17.05 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 12.36 g of Compound 22 (yield 53%). [M + H] = 857

Synthesis Example 23

Compound E 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 20.31 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 15.51 g of a compound 23 (59% yield). [M + H] = 966

Synthesis Example 24

Compound F 10.0 g (1.0 eq), 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline 16.57 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.14 g (0.01 eq) , NaOtBu 5.23 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. After that, the mixture was completely dissolved in CHCl ₃ , washed with water, and then reduced again to remove about 50% of the solvent. Ethyl acetate was added again under reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography, thereby obtaining 14.64 g of Compound 24 (Yield 64%). [M + H] = 841

<Experimental Example>

Comparative Example 1

A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,000 에 was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. product 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 with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then 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 blocking layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum deposited on the EB-1 deposition film at a weight ratio of 98: 2 to form a red light emitting layer having a thickness of 400 Pa. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound with a thickness of 30 Pa 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 a vapor deposition rate of 0.4 to 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 10 2 X ^{- An} organic light emitting device was manufactured by maintaining ⁷ to 5 X 10 ^-6 torr.

Examples 1 to 24

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 Examples 2 to 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.

When current was applied to the organic light emitting devices manufactured in Examples 1 to 24 and Comparative Examples 1 to 21, voltage, efficiency, and life 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 4.47 35.6 168 Red Example 1 Compound 1 3.97 46.5 238 Red Example 2 Compound 2 3.92 48.6 261 Red Example 3 Compound 3 3.95 46.9 242 Red Example 4 Compound 4 3.90 46.5 240 Red Example 5 Compound 5 3.93 47.1 267 Red Example 6 Compound 6 3.88 48.3 281 Red Example 7 Compound 7 4.10 42.3 221 Red Example 8 Compound 8 4.16 43.5 203 Red Example 9 Compound 9 3.99 48.5 251 Red Example 10 Compound 10 3.87 51.3 283 Red Example 11 Compound 11 3.85 51.5 321 Red Example 12 Compound 12 4.01 47.8 303 Red Example 13 Compound 13 3.98 47.5 223 Red Example 14 Compound 14 3.95 48.5 251 Red Example 15 Compound 15 4.13 47.1 225 Red Example 16 Compound 16 4.15 43.5 289 Red Example 17 Compound 17 4.04 43.7 261 Red Example 18 Compound 18 3.85 47.0 257 Red Example 19 Compound 19 4.27 50.2 243 Red Example 20 Compound 20 4.23 46.1 206 Red Example 21 Compound 21 4.01. 41.7 214 Red Example 22 Compound 22 4.25 48.5 279 Red Example 23 Compound 23 4.29 40.2 227 Red Example 24 Compound 24 3.86 45.3 221 Red Comparative Example 2 C-1 5.00 18.4 15 Red Comparative Example 3 C-2 4.96 19.9 21 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 4.90 18.9 23 Red Comparative Example 8 C-7 5.01 17.8 23 Red Comparative Example 9 C-8 5.03 28.4 28 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 4.37 34.5 199 Red Comparative Example 13 C-12 4.23 33.6 179 Red Comparative Example 14 C-13 4.70 35.5 210 Red Comparative Example 15 C-14 4.88 31.9 125 Red Comparative Example 16 C-15 4.43 32.1 230 Red Comparative Example 17 C-16 4.75 24.3 74 Red Comparative Example 18 C-17 4.51 37.1 158 Red Comparative Example 19 C-18 4.47 38.6 167 Red Comparative Example 20 C-19 4.68 28.5 61 Red Comparative Example 21 C-20 4.50 34.4 139 Red

When current was applied to the organic light emitting devices manufactured by Examples 1 to 24 and Comparative Examples 1 to 21, the results of Table 1 were obtained. 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 lower than 30% compared to the comparative example material, and the efficiency was also increased by 30% or more, so that the host was red. It was found that the energy transfer to the dopant was well achieved. In addition, it was found that while maintaining high efficiency, the lifespan characteristics could be greatly improved. It can be judged that this is because the compound of the present invention has higher stability to electrons and holes than the comparative example compound, and the balance of electron and hole movement in the OLED Red device is well balanced. 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.

101: substrate
102: anode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: emitting layer
107: hole blocking layer
108: electron injection and transport layer
110: cathode

Claims (13)

Compound represented by the formula (1):

In Chemical Formula 1,
* Is a position condensed with * in Chemical Formula 1-1,
R1 and R2 are the same as or different from each other, and each independently hydrogen; Or deuterium,
a1 is an integer from 0 to 8, and when a1 is 2 or more, R1 is the same as or different from each other,
a2 is an integer from 0 to 2, and when a2 is 2, R2 is the same or different from each other,
In Chemical Formula 1-1,
X1 to X3 are the same as or different from each other, and each independently N; Or CH, and 2 or more of X1 to X3 are N,
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 heteroaryl group,
L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R3 is hydrogen; Or deuterium,
a3 is an integer of 0 to 6, and when a3 is 2 or more, R3 is the same or different from each other. The method according to claim 1, wherein Formula 1 is a compound represented by the following Formula 3-1 or 3-2:
[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2,
X1 to X3, Ar1, Ar2, L, R1 to R3 and a1 to a3 are defined as defined in Chemical Formula 1. Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2-1 to 2-6:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Chemical Formulas 2-1 to 2-6,
X1 to X3, Ar1, Ar2, L, R1 to R3 and a1 to a3 are defined as defined in Chemical Formula 1. The method according to claim 1,
L is a direct bond; A compound having an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or nitrile groups. The method according to claim 1,
X1 to X3 are N compounds. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms, the aryl group or heteroaryl group being substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. compound. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. 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, wherein at least one layer of the organic material layer comprises the compound according to any one of claims 1 to 7. Light emitting element. The method according to claim 8, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer. The method according to claim 8, The organic material layer comprises 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 8, The organic layer comprises an electron injection layer or an electron transport layer, the electron injection layer or the electron transport layer is an organic light emitting device comprising the compound. The method according to claim 8, The organic layer is a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer selected from the group consisting of more than one layer or more organic Light emitting element.

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