KR102202765B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Compound and organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

The present invention relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0064868 filed with the Korean Intellectual Property Office on June 5, 2018, the entire contents of which are incorporated herein.

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

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

Korean Patent Application Publication No. 10-2017-0058579

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

In addition, the present specification provides an organic light-emitting device having a low driving voltage, high efficiency, excellent lifespan, or high color purity by including the compound represented by Formula 1 above.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

,

또는

이며,Ar1 is

,

or

Is,

X is O, S, Se, SO ₂ , Ge or SiPh ₂ ,

L1 is a direct bond; Or an arylene group, n1 is an integer of 0 to 3, and when n1 is 2 or more, L1 is the same as or different from each other,

L2 is a direct bond; Or an arylene group, n2 is an integer of 0 to 3, and when n2 is 2 or more, L2 is the same as or different from each other,

X1 to X3 are the same as or different from each other, each independently N or CH, and at least one of X1 to X3 is N,

X4 and X5 are the same as or different from each other, and each independently O or S,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Aryl group; Or a heteroaryl group, b3 is an integer of 0 to 4, b5 is an integer of 0 to 4, and when b3 is 2 or more, R3 is the same as or different from each other, and when b5 is 2 or more, R5 is the same or different from each other,

G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Or an aryl group, or by bonding with an adjacent group to form a ring unsubstituted or substituted with deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group or aryl group,

a1 is an integer of 0 to 3, a2 and a3 are each independently an integer of 0 to 4, a4 is an integer of 0 to 6, when a1 is 2 or more, G1 is the same as or different from each other, and a2 is 2 or more G2 is the same or different from each other, when a3 is 2 or more, G3 is the same or different from each other, and when a4 is 2 or more, G4 is the same or different from each other.

Another exemplary embodiment of the present specification is an organic light-emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer is represented by the above-described formula (1). It provides an organic light-emitting device comprising a compound.

The compound represented by Formula 1 according to the present specification may be used as a hole injection, hole transport, electron injection, electron transport, or light emitting material of an organic light emitting device.

In some exemplary embodiments, an organic light-emitting device including the compound represented by Formula 1 in the organic material layer may improve efficiency, decrease a driving voltage, or improve lifespan characteristics. Among them, when the compound of the present invention is included in the light-emitting layer, energy dissipation such as change in color purity and extinction is suppressed, so that the luminous efficiency of the device can be particularly increased.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron transport layer 9, and an electron injection layer 10. And an example of an organic light-emitting device including the cathode 4 is shown.
3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 8, an electron transport layer 9, an electron injection layer 10 and a cathode 4 An example of an organic light emitting device is shown.

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

An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

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

In the present specification, terms such as'include' or'have' mean that the features or elements described in the specification exist, and to exclude the possibility of adding one or more other features or elements in advance no.

In the present specification, when a portion such as a region or a layer is provided on or on another portion, it includes not only the case immediately above the other portion, but also the case in which another region, layer, etc. is interposed therebetween.

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

In the present specification, an alkyl group refers to a linear or branched saturated hydrocarbon. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chain or cyclic.

Specific examples of the chain alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl , Isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

The number of carbon atoms in the cyclic alkyl group (cycloalkyl group) is not particularly limited, but is preferably 3 to 40 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 24 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 14 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 8. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethyl Cyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, an aryl group means a substituted or unsubstituted monocyclic or polycyclic ring that is wholly or partially unsaturated. According to an exemplary embodiment, the aryl group has 6 to 36 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 25 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 18 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 13 carbon atoms. According to an exemplary embodiment, the aryl group has 12 carbon atoms.

The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a quarterphenyl group. Examples of the polycyclic aryl group include naphthyl group, anthracenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, tetracenyl group, chrysenyl group, fluorenyl group, indenyl group, Acenaphthyl group, benzofluorenyl group, and the like, but are not limited thereto.

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

The substituted fluorenyl group may be, for example, any one selected from the following structures, but is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include a thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, Diazinyl group, triazinyl group, acridinyl group, carbonyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group , Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl Group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, iso There are oxazolyl group, thiadiazolyl group, phenoxazinyl group, phenothiazinyl group, and the like, but are not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these. The hydrocarbon ring refers to a ring consisting of only carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle refers to a ring containing at least one heteroatom, and the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

The aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

The aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto.

The aliphatic heterocycle refers to an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.

The aromatic heterocycle refers to an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, acridine, phenane Tridin, diazanaphthalene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarba Sol, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

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

In the compound of Formula 1, L1 is substituted on carbon 1 of triphenylene. The structure in which L1 is substituted on carbon 1 of triphenylene has a more curved structure than the structure in which L1 is substituted on carbon 2 of triphenylene. As a result, steric hindrance between molecules increases, and when a compound is packed for device deposition, efficiency reduction due to intermolecular interaction can be prevented.

In addition, since the compound of Formula 1 has a bent structure, it is possible to secure more triplet energy.

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

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

The definitions of X, L1, L2, X1 to X5, G1 to G4, R1 to R5, a1 to a4, n1, n2, b3 and b5 are the same as defined in Formula 1.

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

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

In the exemplary embodiment of the present specification, X1 to X3 are the same as or different from each other, each independently N or CH, and at least two of X1 to X3 are N.

In the exemplary embodiment of the present specification, X1 is N, and X2 and X3 are each independently N or CH.

In the exemplary embodiment of the present specification, X3 is N, and X1 and X2 are each independently N or CH.

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

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

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

In the exemplary embodiment of the present specification, X4 is O.

In the exemplary embodiment of the present specification, X4 is S.

In the exemplary embodiment of the present specification, X5 is O.

In the exemplary embodiment of the present specification, X5 is S.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it is a C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; An alkyl group having 1 to 8 carbon atoms; Aryl group having 6 to 25 carbon atoms; Or it is a C2-C25 heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; An alkyl group having 1 to 6 carbon atoms; Aryl group having 6 to 18 carbon atoms; Or it is a C2-C18 heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; An alkyl group having 1 to 4 carbon atoms; Aryl group having 6 to 13 carbon atoms; Or a C2-C13 heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Aryl group; Monocyclic heteroaryl group; A bicyclic heteroaryl group containing 3 or more N; A bicyclic heteroaryl group including O or S; Or a tricyclic or more heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Aryl group; Monocyclic heteroaryl group; A bicyclic heteroaryl group including O or S; Or a tricyclic or more heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; An alkyl group having 1 to 6 carbon atoms; Aryl group having 6 to 18 carbon atoms; A monocyclic heteroaryl group having 2 to 5 carbon atoms; A C 5 to C 7 bicyclic heteroaryl group containing 3 or more N; A bicyclic heteroaryl group containing O or S having 6 to 11 carbon atoms; Or a C 9 to C 16 tricyclic or more heteroaryl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, when n1 is 0 and n2 is 0, at least one of R1 and R2 is an aryl group having 10 or more carbon atoms.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently a methyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently an aryl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or a naphthyl group.

In an exemplary embodiment of the present specification, R3 is hydrogen; Or an aryl group having 6 to 18 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; Or an aryl group having 6 to 12 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; Or an aryl group having 6 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; Or a phenyl group.

In the exemplary embodiment of the present specification, R4 is hydrogen; Alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, R4 is hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; An alkyl group having 1 to 6 carbon atoms; Or an aryl group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; An alkyl group having 1 to 4 carbon atoms; Or an aryl group having 6 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; Methyl group; Or a phenyl group.

In the exemplary embodiment of the present specification, R5 is hydrogen.

In the exemplary embodiment of the present specification, G1 is hydrogen.

In the exemplary embodiment of the present specification, G2 is hydrogen.

In the exemplary embodiment of the present specification, G3 is hydrogen.

In the exemplary embodiment of the present specification, G4 is hydrogen.

In the exemplary embodiment of the present specification, L1 is a direct bond; Or an arylene group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L1 is a direct bond; Or an arylene group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, L1 is a direct bond; Or an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L1 is a direct bond; Or an arylene group having 6 to 14 carbon atoms.

In the exemplary embodiment of the present specification, L2 is a direct bond; Or an arylene group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, L2 is a direct bond; Or an arylene group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, L2 is a direct bond; Or an arylene group having 6 to 13 carbon atoms.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or it is a naphthalene group.

In this specification, the naphthalene group means a divalent naphthyl group.

In the exemplary embodiment of the present specification, L1 is a direct bond; Phenylene group; Or it is a naphthalene group.

In the exemplary embodiment of the present specification, L2 is a phenylene group.

In the exemplary embodiment of the present specification, L2 is an m-phenylene group; Or p-phenylene group.

In the exemplary embodiment of the present specification, n1 is 0.

In the exemplary embodiment of the present specification, n2 is 0.

In the exemplary embodiment of the present specification, n2 is 1.

In the exemplary embodiment of the present specification, the sum of n1 and n2 is 0 or 1.

In the exemplary embodiment of the present specification, b3 is 0 or 1.

In the exemplary embodiment of the present specification, b5 is 0 or 1.

는 하기 구조들 중에서 선택된 어느 하나이다.In an exemplary embodiment of the present specification, the

Is any one selected from the following structures.

In the above structures, two * are sites connected to L1 and L2, respectively,

The definitions of G4 and a4 are the same as those defined in Chemical Formula 1.

는 하기 구조들 중에서 선택된 어느 하나이다.In an exemplary embodiment of the present specification, the

Is any one selected from the following structures.

In the above structures, two * are sites connected to L1 and L2, respectively,

The definitions of G4 and a4 are the same as those defined in Chemical Formula 1.

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

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 described above may be prepared according to the following General Formula 1 or 2.

[General Formula 1]

[General Formula 2]

An example of synthesizing the compound of Formula 1 can be easily prepared by a synthesis method commonly used in the art, that is, Suzuki reaction (a coupling reaction between halogen and acid or boron ester).

In the general formulas 1 and 2, the definitions of X, L1, L2, n1, n2, G1 to G4, a1 to a4, and Ar1 are the same as those defined in Chemical Formula 1.

The general formulas 1 and 2 are an example of a method of forming the compound of formula 1, and the synthesis method of formula 1 is not limited to the general formulas 1 and 2, and may be performed by methods known in the art. .

The present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1. The meaning that the organic light-emitting device includes the compound represented by Formula 1 means that the organic light-emitting device includes one or two or more compounds represented by Formula 1. When the organic light-emitting device includes two or more compounds represented by Formula 1, the two or more compounds may be the same or different from each other.

An exemplary embodiment of the present specification is an organic light-emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer is represented by the above-described formula (1). It provides an organic light-emitting device comprising a compound.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention is an organic material layer, a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a hole control layer, a light-emitting layer, an electron control layer, an electron transport layer, an electron injection layer, and an electron transport and injection at the same time. It may have a structure including a layer or the like.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above.

In the present specification, the meaning that the compound represented by Formula 1 is included in the M or N layer means that the compound represented by Formula 1 is included only in the M layer, only in the N layer, or in both the M layer and the N layer. It means everything that is included. When the compound represented by Formula 1 is included in two or more different organic material layers, the compounds represented by Formula 1 included in the plurality of organic material layers may be the same or different from each other.

In the exemplary embodiment of the present specification, the organic material layer includes a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, or a layer controlling a hole, and performing the hole transport layer, the hole injection layer, and the hole transporting and injection at the same time. The layer or hole control layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons or an electron controlling layer, and performing the electron transport layer, the electron injection layer, and the electron transporting and injecting simultaneously The layer or electron control layer includes the compound represented by Formula 1.

In the exemplary embodiment of the present specification, the emission layer further includes a dopant.

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

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

In the exemplary 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.

The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.

The organic light emitting device according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4, as shown in FIG. 1. In one embodiment, the compound of Formula 1 is included in the organic material layer (3).

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, and a light emitting layer, as shown in FIG. (8), the electron transport layer 9, the electron injection layer 10 and may be made of a cathode (4). In one embodiment, the compound of Formula 1 is included in the light emitting layer (8). In another embodiment, the compound of Formula 1 is included in the hole transport layer 5, the hole transport layer 6, or the hole control layer 7. In another exemplary embodiment, the compound of Formula 1 is included in the electron transport layer 9 or the electron injection layer 10.

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 8, an electron transport layer 9, as shown in FIG. It may be made of an electron injection layer 10 and a cathode 4. In one embodiment, the compound of Formula 1 is included in the light emitting layer (8).

However, the structure of the organic light-emitting device according to the exemplary embodiment of the present specification is not limited to FIGS. 1 to 3 and may be any one of the following structures.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Anode

(3) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(5) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode

(6) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(7) Anode/hole transport layer/hole control layer/light-emitting layer/electron transport layer/cathode

(8) Anode/hole transport layer/hole control layer/light emitting layer/electron transport layer/electron injection layer/cathode

(9) Anode/hole injection layer/hole transport layer/hole control layer/light emitting layer/electron transport layer/cathode

(10) Anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(11) Anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/light-emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

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 may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition method (PVD, physical vapor deposition) such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition, the compound of 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

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

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes received from an electrode into a light emitting layer or a layer adjacent to the light emitting layer. The hole injection material has the ability to transport holes and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and has excellent thin film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

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

The hole control layer is a layer that prevents the flow of electrons into the light emitting layer to the anode and controls the flow of holes flowing into the light emitting layer to control the performance of the entire device. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light-emitting layer to the anode and to control the flow of holes injected into the light-emitting layer or the light-emitting material. In one embodiment, an aryl amine-based organic material may be used for the hole control layer, but is not limited thereto.

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

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

Examples of the dopant material for the light emitting layer include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex or a platinum complex, but is not limited thereto.

The electron control layer is a layer that blocks the inflow of holes from the emission layer to the cathode and controls the electrons flowing into the emission layer to control the performance of the entire device. The electron controlling material is preferably a compound having the ability to prevent the inflow of holes from the light-emitting layer to the cathode and to control electrons injected into the light-emitting layer or the light-emitting material. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control layer is located between the emission layer and the cathode, and is preferably provided in direct contact with the emission layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used according to the prior art. In one embodiment, the negative electrode material is a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium, and an aluminum layer or a silver layer may be formed on the layer after forming a layer with the material.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has an ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and prevents movement of excitons generated in the light emitting layer to the hole injection layer In addition, it is preferable to use a compound excellent in thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

Hereinafter, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited by the examples presented below.

Synthesis of compound 1

4-bromodibenzo[b,d]furan) 10g (40.66mmol), 4,4,5,5-tetramethyl-2-(triphenylen-1-yl) -1,3,2-dioxaborolane (4,4,5,5-tetramethyl-2-(triphenylen-1-yl)-1,3,2-dioxaborolane) 14.4 g (40.66 mmol) and tetrakistri Add 2 mol% of phenylphosphine palladium (Tetrakis(triphenylphosphine) palladium) to 120 ml of tetrahydrofuran, and dissolve 121.98 mmol of potassium carbonate in 60 ml of water and mix. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. This was filtered through a silica pad, and the solution was concentrated under reduced pressure, followed by column purification, to give 12.9 g (yield 81%) of compound 1-1.

After dissolving 12.9 g (32.73 mmol) of Compound 1-1 in 90 ml of tetrahydrofuran under a nitrogen atmosphere, 30.6 ml of 1.6M n-BuLi was slowly added dropwise by lowering the temperature to -78°C. After stirring at low temperature for 3 hours, raising the temperature to room temperature, stirring for an additional 2 hours, lowering the temperature to -78°C again, and then adding 18.3 g of Triisopropyl borate. The reaction was terminated by stirring at low temperature for an hour, raising the temperature to room temperature, and stirring for an additional 3 hours, and 50 ml of an aqueous ammonium chloride solution was added to separate the layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. Filtered through a silica pad, concentrated the solution under reduced pressure, and purified by column to give 9.2 g (yield 64%) of compound 1-2.

Compound 1-2 9.2g (20.9mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 5.6g (20.9mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 2mol% were added to 60ml of tetrahydrofuran, and 62.7mmol of potassium carbonate was dissolved in 30ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified, and 9.4 g (yield 72%) of compound 1 was obtained.

MS: [M+H] ⁺ = 626

Synthesis of compound 2

Compound 1-2 10g (22.82mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2-(3-bromophenyl)-4,6-diphenyl- Except for using 1,3,5-triazine) 8.8g (22.82mmol), 13.3g (yield 83%) of compound 2 was obtained in the same manner as in the synthesis of compound 1 above.

MS: [M+H] ⁺ = 702

Synthesis of compound 3

Compound 1-2 10g (22.82mmol) and 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyridine (4-([1,1'-biphenyl]-3 Except for using -yl)-2-chloro-6-phenylpyridine) 7.8g (22.82mmol), 10.9g (yield 68%) of Compound 3 was obtained in the same manner as in the synthesis of Compound 1.

MS: [M+H] ⁺ = 700

Synthesis of compound 4

Compound 1-2 10g (22.82mmol) and 4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine (4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine) 7.2g Except for using (22.82 mmol), 10.2 g of compound 4 (66% yield) was obtained in the same manner as in the synthesis of compound 1 above.

MS: [M+H] ⁺ = 675

Synthesis of compound 5

4-bromodibenzo[b,d]thiophene) 10g (38.18mmol), 4,4,5,5-tetramethyl-2-(triphenylen-1-yl) )-1,3,2-dioxaborolane (4,4,5,5-tetramethyl-2-(triphenylen-1-yl)-1,3,2-dioxaborolane) 13.5g (38.18mmol) and tetrakis Add 2 mol% of triphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) to 120 ml of tetrahydrofuran, and dissolve 114.54 mmol of potassium carbonate in 60 ml of water and mix. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and purified by column, and 12.1 g (yield 77%) of compound 5-1 was obtained.

After dissolving 12.1g (29.5mmol) of compound 5-1 in 90ml of tetrahydrofuran under a nitrogen atmosphere, 27.6ml of 1.6M n-BuLi was slowly added dropwise by lowering the temperature to -78°C. After stirring at low temperature for 3 hours, raising the temperature to room temperature, stirring for an additional 2 hours, lowering the temperature to -78°C, and adding 17.6 g of Triisopropyl borate. After stirring at low temperature for 1 hour, raising the temperature to room temperature and stirring for an additional 3 hours, the reaction was terminated, and 50 ml of an aqueous ammonium chloride solution was added to separate layers. Anhydrous magnesium sulfate was added to the separated organic material layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 8 g (yield 60%) of intermediate 5-2 was obtained.

Compound 5-2 8g (17.62mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 4.7 g (17.62 mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 2 mol% was added to 50 ml of tetrahydrofuran, and 52.86 mmol of potassium carbonate was dissolved in 25 ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified, and 7.1 g (yield 63%) of compound 5 was obtained.

MS: [M+H] ⁺ = 642

Synthesis of compound 6

Compound 5-2 10g (22.02mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2-(3-bromophenyl)-4,6-diphenyl- Except for using 1,3,5-triazine) 8.5g (22.02mmol), compound 6 12g (yield 76%) was obtained by the same method as the synthesis of compound 5 above.

MS: [M+H] ⁺ = 718

Synthesis of compound 7

Compound 5-2 10g (22.02mmol) and 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyridine (4-([1,1'-biphenyl]-3 Except for using -yl)-2-chloro-6-phenylpyridine) 7.5g (22.02mmol), 10.7g (yield 68%) of compound 7 was obtained in the same manner as in the synthesis of compound 5 above.

MS: [M+H] ⁺ = 716

Synthesis of compound 8

Compound 5-2 10g (22.02mmol) and 4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine (4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine) 7.0g Except for using (22.02 mmol), 11.1 g (yield 73%) of compound 8 was obtained in the same manner as in the synthesis of compound 5 above.

MS: [M+H] ⁺ = 691

Synthesis of compound 9

4-bromodibenzo[b,d]furan (4-bromodibenzo[b,d]furan) 10g(40.66mmol), (3-(triphenylen-1-yl)phenyl)boronic acid ((3-(triphenylen) -1-yl)phenyl)boronic acid) 14.2g (40.66mmol) and tetrakistriphenyl phosphine palladium (Tetrakis(triphenylphosphine) palladium) 2mol% in tetrahydrofuran 120ml, potassium carbonate 121.98mmol is dissolved in 60ml of water and mixed. give. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtering a silica pad, the solution was concentrated under reduced pressure and purified by column to give 15.5 g (yield 81%) of compound 9-1.

After dissolving 15.5 g (32.86 mmol) of Compound 9-1 in 90 ml of tetrahydrofuran under a nitrogen atmosphere, 30.8 ml of 1.6M n-BuLi was slowly added dropwise by lowering the temperature to -78°C. After stirring at low temperature for 3 hours, raising the temperature to room temperature, stirring for an additional 2 hours, and then lowering the temperature to -78°C, 18.4 g of Triisopropyl borate is added. After stirring at low temperature for 1 hour, raising the temperature to room temperature and stirring for an additional 3 hours to terminate the reaction, 50 ml of ammonium chloride aqueous solution was added and the layers were separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 10.6 g (yield 63%) of compound 9-2 was obtained.

에서 12시간 교반한 후 반응을 종결하고 상온으로 식혀 물과 유기층을 분리해준다. 분리한 유기층에 무수 황산 마그네슘(anhydrous magnesium sulfate)을 넣고 교반한다. 실리카 패드(silica pad)로 여과 후 감압 하에서 용액을 농축하여 컬럼 정제하였고 화합물 9 10.1g(수율 70%)을 수득하였다.Compound 9-2 10.6g (20.62mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 5.5g (20.62mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 2mol% in tetrahydrofuran 60ml, potassium carbonate 61.86mmol is dissolved in 30ml of water and mixed. 80

After stirring at for 12 hours, the reaction was terminated, cooled to room temperature, and water and the organic layer were separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified to obtain 10.1 g (yield 70%) of compound 9.

MS: [M+H] ⁺ = 702

Synthesis of compound 10

4-bromodibenzo[b,d]thiophene) 10g(38.18mmol), (3-(triphenylen-1-yl)phenyl)boronic acid ((3-( triphenylen-1-yl)phenyl)boronic acid) 13.3g (38.18mmol) and tetrakistriphenylphosphine palladium 2mol% in tetrahydrofuran 120ml, potassium carbonate 114.54mmol dissolved in water 60ml Mix it. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic material layer and stirred. After filtration with a silica pad, the solution was concentrated under reduced pressure and column-purified to give 14.3 g (yield 77%) of compound 10-1.

After dissolving 14.3g (29.42mmol) of compound 10-1 in 90ml of tetrahydrofuran under a nitrogen atmosphere, 27.6ml of 1.6M n-BuLi was slowly added dropwise by lowering the temperature to -78°C. After stirring at low temperature for 3 hours, raising the temperature to room temperature, stirring for an additional 2 hours, lowering the temperature to -78 ℃ again, and then adding 16.4 g of Triisopropyl borate. After stirring at low temperature for 1 hour, raising the temperature to room temperature and stirring for an additional 3 hours to terminate the reaction, 50 ml of ammonium chloride aqueous solution was added and the layers were separated. Anhydrous magnesium sulfate was added to the separated organic material layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified to give 9.2 g (59% yield) of compound 10-2.

Compound 10-2 9.2g (17.35mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 5.9g (17.35mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 2mol% were added to 50ml of tetrahydrofuran, and 52.05mmol of potassium carbonate was dissolved in 25ml of water and mixed. The reaction was terminated by stirring at 80° C. for 12 hours, cooled to room temperature, and water and the organic layer were separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified to obtain 8.9 g (66% yield) of compound 10.

MS: [M+H] ⁺ = 777

Synthesis of compound 11

Compound 11 in the same manner as in the synthesis of Compound 1 except for using Compound 1-2 10g (22.82mmol) and 2-chlorobenzo[d]thiazole 4.8g (22.82mmol). 7.8 g (65% yield) was obtained.

MS: [M+H] ⁺ = 528

Synthesis of compound 12

Compound 12 in the same manner as in the synthesis of Compound 1 except for using Compound 1-2 10g (22.02mmol) and 2-chlorobenzo[d]oxazole 3.4g (22.02mmol). 8.1 g (70% yield) was obtained.

MS: [M+H] ⁺ = 528

Synthesis of compound 13

4-bromodibenzo[b,d]furan) 10g (40.66mmol), (4-(triphenylen-1-yl)naphthalen-1-yl)boronic acid (( 4-(triphenylen-1-yl)naphthalen-1-yl)boronic acid) 16.2 g (40.66 mmol) and tetrakistriphenyl phosphine palladium (Tetrakis (triphenylphosphine) palladium) 2 mol% in tetrahydrofuran 120 ml potassium carbonate Dissolve 121.98mmol in 60ml of water and mix. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtering a silica pad, the solution was concentrated under reduced pressure and purified by column to give 17.1 g (yield 84%) of compound 13-1.

After dissolving 17.1 g (32.86 mmol) of compound 13-1 in 90 ml of tetrahydrofuran under a nitrogen atmosphere, 30.8 ml of 1.6M n-BuLi was slowly added dropwise by lowering the temperature to -78°C. After stirring at low temperature for 3 hours, raising the temperature to room temperature, stirring for an additional 2 hours, and then lowering the temperature to -78°C, 18.4 g of Triisopropyl borate is added. After stirring at low temperature for 1 hour, raising the temperature to room temperature and stirring for an additional 3 hours to terminate the reaction, 50 ml of ammonium chloride aqueous solution was added and the layers were separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 11.63 g (yield 63%) of compound 13-2 was obtained.

Compound 13-2 11.63g (20.62mmol), 1-chloro-4,6-diphenyltriazine (1-chloro-4,6-diphenyltriazine) 5.5g (20.62mmol) and tetrakistriphenylphosphine palladium ( Tetrakis (triphenylphosphine) palladium) 2 mol% was added to 60 ml of tetrahydrofuran, and 61.86 mmol of potassium carbonate was dissolved in 30 ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction is terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the separated organic layer and stirred. After filtration through a silica pad, the solution was concentrated under reduced pressure and column-purified to obtain 9.92 g (64% yield) of compound 13.

MS: [M+H] ⁺ = 752

Synthesis of compound 14

Except for using Compound 1-2 and 2-chloro-3-methyl-2,3-dihydrobenzo[d]oxazole (2-chloro-3-methyl-2,3-dihydrobenzo[d]oxazole), the above Compound 14 was obtained in the same manner as in the synthesis of compound 1.

MS: [M+H] ⁺ = 528

Synthesis of compound 15

Except for using the compound 9-2 and 2-chloro-3-phenyl-2,3-dihydrobenzo[d]thiazole (2-chloro-3-phenyl-2,3-dihydrobenzo[d]thiazole), the above Compound 15 was obtained in the same manner as in the synthesis of compound 9.

MS: [M+H] ⁺ = 682

<Example 1>

A glass substrate coated with a thin film of ITO (Indium tin oxide) with a thickness of 100 nm was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the prepared ITO transparent electrode, m-MTDATA (hole injection layer; 60 nm) / TCTA (hole transport layer; 80 nm) / 94wt% Formula 1 + 6wt% Ir(ppy) ₃ (light emitting layer; 300 nm) / BCP (electron transport layer; 10 nm) / Alq ₃ (electron injection layer; 30 nm) / LiF (1 nm) / Al (200 nm) (cathode) by depositing an organic material layer in the order to prepare an organic light emitting device.

The structures of m-MTDATA, TCTA, Ir(ppy) _3, Alq ₃ and BCP are as follows, respectively.

<Examples 2 to 15>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used instead of compound 1 in Example 1.

<Comparative Examples 1 to 6>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used instead of compound 1 in Example 1.

By applying a current to the organic light emitting device of the above Examples and Comparative Examples, the results of Table 1 were obtained. In Table 1 below, the EL peak means the maximum emission wavelength.

compound
(Host) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) EL peak
(nm) Example 1 One 3.72 45.93 517 Example 2 2 3.82 44.64 516 Example 3 3 3.84 43.82 518 Example 4 4 3.79 44.75 517 Example 5 5 3.81 43.51 515 Example 6 6 3.75 44.53 516 Example 7 7 3.78 45.52 516 Example 8 8 3.69 44.54 517 Example 9 9 3.87 43.58 518 Example 10 10 3.77 42.14 518 Example 11 11 3.83 43.58 518 Example 12 12 3.79 43.14 518 Example 13 13 3.81 44.35 516 Example 14 14 3.78 43.18 518 Example 15 15 3.80 45.04 516 Comparative Example 1 GH1 5.78 38.47 517 Comparative Example 2 GH2 5.90 37.21 517 Comparative Example 3 GH3 5.67 36.11 517 Comparative Example 4 GH4 5.81 38.17 517 Comparative Example 5 GH5 5.64 39.08 518 Comparative Example 6 GH6 5.71 35.42 518

As a result of the experiment, the green organic light-emitting devices of Examples 1 to 15 using the compounds represented by the compounds 1 to 15 according to the present invention as a host material of the emission layer have current efficiency and driving voltage compared to the green organic light-emitting devices of Comparative Examples 1 to 6 Showed excellent performance in terms of.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: hole transport layer
7: hole control layer
8: light emitting layer
9: electron transport layer
10: electron injection layer

Claims (10)

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

In Formula 1,
Ar1 is

,

or

Is,
X is O, S or Se,
L1 is a direct bond; Or an arylene group, n1 is an integer of 0 to 3, and when n1 is 2 or more, L1 is the same as or different from each other,
L2 is a direct bond; Or an arylene group, n2 is an integer of 0 to 3, and when n2 is 2 or more, L2 is the same as or different from each other,
X1 to X3 are the same as or different from each other, each independently N or CH, and at least one of X1 to X3 is N,
X4 and X5 are the same as or different from each other, and each independently O or S,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Aryl group; Or a heteroaryl group, b3 is an integer of 0 to 4, b5 is an integer of 0 to 4, and when b3 is 2 or more, R3 is the same as or different from each other, and when b5 is 2 or more, R5 is the same or different from each other,
G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Alkyl group; Or an aryl group, or by bonding with an adjacent group to form a ring unsubstituted or substituted with deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group or aryl group,
a1 is an integer of 0 to 3, a2 and a3 are each independently an integer of 0 to 4, a4 is an integer of 0 to 6, when a1 is 2 or more, G1 is the same as or different from each other, and a2 is 2 or more G2 is the same or different from each other, when a3 is 2 or more, G3 is the same or different from each other, and when a4 is 2 or more, G4 is the same or different from each other. delete The method of claim 1, wherein

Is any one selected from the following structures:

In the above structures, two * are sites connected to L1 and L2, respectively,
The definitions of G4 and a4 are the same as those defined in Chemical Formula 1. The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a compound that is a naphthalene group. The method according to claim 1, wherein R1 to R5 are the same as or different from each other, and each independently a methyl group; Phenyl group; Biphenyl group; Or a compound that is a naphthyl group. The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer is a chemical formula according to any one of claims 1 and 3 to 6 An organic light-emitting device comprising a compound represented by 1. The organic light-emitting device of claim 7, wherein the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1. The method according to claim 7, wherein the organic material layer comprises a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, or a hole controlling layer, and the hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, or controlling holes The organic light emitting diode layer includes the compound represented by Chemical Formula 1. The method of claim 7, wherein the organic material layer comprises an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons or an electron controlling layer, and the electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, or controlling electrons The organic light emitting diode layer includes the compound represented by Chemical Formula 1.

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