KR20190018397A - Compound containing nitrogen and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a nitrogen-containing cyclic compound capable of improving low driving voltage and/or lifetime characteristics in an organic light emitting device; and an organic light emitting device including the compound. The nitrogen-containing cyclic compound is represented by chemical formula 1 in which X1 to X3 are the same or different, and are each independently N or CR, at least two of X1 to X3 are N, R is hydrogen or a substituted or unsubstituted aryl group, and R2 and R3 are the same or different, and are each independently a substituted or unsubstituted aryl group.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing heterocyclic ring compound and an organic light-

This specification claims the benefit of Korean Patent Application No. 10-2017-0102992, filed on August 14, 2017, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD The present disclosure relates to nitrogen-containing ring compounds and organic light-emitting devices comprising the same.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, 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 may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Publication No. 2000-0051826

Nitrogen ring compounds and organic light emitting devices containing them are described in this specification.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X1 to X3 are the same or different and each independently N or CR, and at least two of X1 to X3 are N,

R is hydrogen; Or a substituted or unsubstituted aryl group,

R2 and R3 are the same or different and are each independently a substituted or unsubstituted aryl group,

R 1 is a carbazole group substituted with an alkyl group or a silyl group; A triazinyl group substituted with an aryl group; Or a pyrimidinyl group substituted with an aryl group,

n is 4 or 5, and 4 or 5 R1's are the same or different from each other.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can emit a high-luminance light in the organic light emitting device, and can improve the efficiency, the low driving voltage and / or the lifetime characteristics. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron suppressing, luminescence, hole blocking, electron transporting, or electron injecting materials.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
Fig. 2 is a cross-sectional view showing the structure of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, 9) and a cathode (4).

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

The present invention provides a compound represented by the following formula (1). The compound represented by the following formula (1) has a small energy difference between the triplet and the singlet, so that the exciton migration (RISC) from the triplet to the singlet occurs efficiently. Therefore, When used for an organic material layer, not only the efficiency of the organic light emitting device is improved, but also a low driving voltage and an excellent lifetime characteristic.

[Chemical Formula 1]

In Formula 1,

X1 to X3 are the same or different and each independently N or CR, and at least two of X1 to X3 are N,

R is hydrogen; Or a substituted or unsubstituted aryl group,

R2 and R3 are the same or different and are each independently a substituted or unsubstituted aryl group,

R 1 is a carbazole group substituted with an alkyl group or a silyl group; A triazinyl group substituted with an aryl group; Or a pyrimidinyl group substituted with an aryl group,

n is 4 or 5, and 4 or 5 R1's are the same or different from each other.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

는 다른 치환기 또는 화합물에 결합되는 부위를 의미한다.In the present specification,

Quot; means a moiety bonded to another substituent or compound.

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl (TMS), triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups But is not limited thereto.

In the present specification, the boron group may be represented by the formula of -BR _d R _e , wherein R _d and R _e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, Hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-tert-butylpentyl group, 1-methylbutyl group, Methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, , tert-octyl group, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is 1 to 40 carbon atoms and, according to one embodiment, has 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, But are not limited to, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, .

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazoline group, a naphthobenzofuran group, or a benzoimidazophenanthridine group, but the present invention is not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In this specification, " adjacent " The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. 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, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

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

In the present specification, the explanation about the aryl group except the aromatic hydrocarbon ring is divalent can be applied.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.

In the present specification, X1 to X3 are the same or different and each independently N or CR, and at least two of X1 to X3 are N.

In another embodiment, X1 to X3 are N.

According to yet another embodiment, X1 and X2 are N and X3 is CR.

In another embodiment, X2 and X3 are N and X1 is CR.

In one embodiment of the present disclosure, R is selected from the group consisting of hydrogen; Or a substituted or unsubstituted aryl group.

In another embodiment, R is selected from the group consisting of hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, R is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R is selected from the group consisting of hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, R is selected from the group consisting of hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to another embodiment, R is hydrogen; A phenyl group; Or a biphenyl group.

In another embodiment, R is hydrogen.

In one embodiment of the present invention, R 2 and R 3 are the same or different and each independently a substituted or unsubstituted aryl group.

According to another embodiment, R 2 and R 3 are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R 2 and R 3 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R 2 and R 3 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, R 2 and R 3 are the same or different and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to another embodiment, R 2 and R 3 are the same or different and are each independently a phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

R1 and n are the same as defined in the above formula (1)

R11 is hydrogen; Or a substituted or unsubstituted aryl group,

R12 to R15 are the same or different and each independently represents a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, R11 is selected from the group consisting of hydrogen; Or a substituted or unsubstituted aryl group.

In another embodiment R11 is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, R11 is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment R11 is hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment R11 is hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to another embodiment, R11 is hydrogen; A phenyl group; Or a biphenyl group.

In another embodiment, R11 is hydrogen.

In one embodiment of the present invention, R12 to R15 are the same or different and each independently a substituted or unsubstituted aryl group.

According to another embodiment, R12 to R15 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R12 to R15 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R12 to R15 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, R12 to R15 are the same or different and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to another embodiment, R12 to R15 are the same or different and are each independently a phenyl group; Or a biphenyl group.

In one embodiment of the present invention, n is 4 or 5, and when n is 4, 4 R1's are the same or different, and when n is 5, 5 R1's are the same or different from each other.

In one embodiment of the present specification, R 1 is a carbazolyl group substituted with an alkyl group or a silyl group; A triazinyl group substituted with an aryl group; Or a pyrimidinyl group substituted with an aryl group.

In another embodiment, R 1 is a carbazolyl group substituted with an alkyl group or a silyl group having 1 to 40 carbon atoms; A triazinyl group substituted with an aryl group having 6 to 60 carbon atoms; Or a pyrimidinyl group substituted with an aryl group having 6 to 60 carbon atoms.

According to another embodiment, R 1 is a carbazolyl group substituted with an alkyl group having 1 to 20 carbon atoms or a silyl group; A triazinyl group substituted with an aryl group having 6 to 30 carbon atoms; Or a pyrimidinyl group substituted with an aryl group having 6 to 30 carbon atoms.

In another embodiment, R 1 is a carbazole group substituted with a methyl group, a tert-butyl group or a trimethylsilyl group; A triazinyl group substituted with a phenyl group or a biphenyl group; Or a pyrimidinyl group substituted with a phenyl group or a biphenyl group.

According to another embodiment, R1 may be any of the following structures.

In the above structures,

R21 to R28 are the same or different from each other, and each independently hydrogen; An alkyl group; Or a silyl group, at least one of R21 to R28 is an alkyl group or a silyl group,

R31 and R32 are the same or different from each other, and each independently hydrogen; Or an aryl group, at least one of R31 and R32 is an aryl group,

R33 to R35 are the same or different from each other, and each independently hydrogen; Or an aryl group, and at least one of R33 to R35 is an aryl group.

In one embodiment of the present specification, R21 to R28 are the same or different from each other and each independently hydrogen; An alkyl group having 1 to 40 carbon atoms; Or silyl group, and at least one of R 21 to R 28 is an alkyl group or a silyl group having 1 to 40 carbon atoms.

According to another embodiment, R21 to R28 are the same or different from each other and each independently hydrogen; An alkyl group having 1 to 20 carbon atoms; Or silyl group, and at least one of R 21 to R 28 is an alkyl group having 1 to 20 carbon atoms or a silyl group.

In another embodiment, R21 to R28 are the same or different from each other and each independently hydrogen; Methyl group; tert-butyl group; Or a trimethylsilyl group, and at least one of R21 to R28 is a methyl group; tert-butyl group; Or a trimethylsilyl group.

According to another embodiment, R 23 and R 26 are the same or different from each other and are each independently a methyl group; tert-butyl group; Or a trimethylsilyl group, and R21, R22, R24, R25, R27 and R28 are hydrogen, or R21 is a methyl group; tert-butyl group; Or a trimethylsilyl group, and R22 to R28 are hydrogen.

In one embodiment of the present specification, R31 and R32 are the same or different from each other, and each independently hydrogen; Or an aryl group having 6 to 60 carbon atoms, and at least one of R31 and R32 is an aryl group having 6 to 60 carbon atoms.

In another embodiment, R31 and R32 are the same or different and each independently hydrogen; Or an aryl group having 6 to 30 carbon atoms, and at least one of R31 and R32 is an aryl group having 6 to 30 carbon atoms.

According to another embodiment, R31 and R32 are the same or different and each independently hydrogen; A phenyl group; A biphenyl group; Or a naphthyl group, at least one of R31 and R32 is a phenyl group; A biphenyl group; Or a naphthyl group.

According to another embodiment, R31 and R32 are phenyl groups.

In one embodiment of the present specification, R33 to R35 are the same or different from each other and each independently hydrogen; Or an aryl group having 6 to 60 carbon atoms, and at least one of R33 to R35 is an aryl group having 6 to 60 carbon atoms.

In another embodiment, R33 to R35 are the same or different and each independently hydrogen; Or an aryl group having 6 to 30 carbon atoms, and at least one of R33 to R35 is an aryl group having 6 to 30 carbon atoms.

According to another embodiment, R33 to R35 are the same or different and each independently hydrogen; A phenyl group; A biphenyl group; Or a naphthyl group, at least one of R33 to R35 is a phenyl group; A biphenyl group; Or a naphthyl group.

In another embodiment R33 is hydrogen and R34 and R35 are phenyl groups.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following structures.

In the above structures, TMS means trimethylsilyl group.

The compound of formula (I) of the present invention can be prepared into a core structure as described in the production example to be described later. Substituent groups may be attached by methods known in the art, and the type, position and number of substituent groups may be varied according to techniques known in the art.

The conjugation length and energy band gap of the compounds of the present invention are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, the HOMO and LUMO energy levels of a compound can be controlled by introducing a carbazole group substituted with an alkyl group or a silyl group, a triazinyl group substituted with an aryl group, or a pyridinyl group substituted with an aryl group into the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention 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 may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a hole blocking layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the above formula (1).

In the organic light emitting device of the present invention, the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.

As another example, the organic material layer may include a light emitting layer, the light emitting layer may include a compound represented by Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host. The dopant may be 100 parts by weight May be 1 to 50 parts by weight. When the content of the dopant satisfies the above range, it is possible to manufacture an organic light emitting device having high efficiency and long life characteristics by transferring triplet energy to a singlet energy.

The compound of Formula 1 may be used as a thermally activated delayed fluorescence (TADF), and the compound of Formula 1 may be a green phosphor having a DELTA E _st value of less than 0.2 eV, When used as a series thermal activation delay fluorescent dopant, it is possible to realize an organic light emitting device capable of emitting light of a high luminance, having a low driving voltage, and having a long life span.

The thermally activated delayed fluorescence means a phenomenon in which transit transition is induced from triplet excited state to singlet excited state due to heat energy and exciton of singlet excited state moves to the ground state to cause fluorescence emission . In addition,? E _st means Singlet energy - Triplet energy value.

In one embodiment of the present invention, the organic layer includes a light-emitting layer, the light-emitting layer includes a compound represented by Formula 1 as a dopant, a fluorescent host or a phosphorescent host, have. The dopant content may be 1 to 50 parts by weight based on 100 parts by weight of the host, and the fluorescent emitter may be 0 to 10 parts by weight based on 100 parts by weight of the host.

In addition, when the light emitting layer further includes a fluorescent emitter, the compound represented by Formula 1 transmits an exciton energy to the fluorescent emitter and causes a luminescence phenomenon in the fluorescent emitter, so that it is possible to emit a high luminance, It is possible to manufacture an organic light emitting device having low and long lifetime characteristics.

As the fluorescent emitter, fluorescent materials such as an anthracene-based compound, a pyrene-based compound, and a boron-based compound may be used, but the present invention is not limited thereto.

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

According to another embodiment, the first electrode is a cathode and the second electrode is a cathode.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

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

2 shows a structure in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injecting and transporting layer 9) and a cathode 4 are sequentially laminated on a transparent substrate. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, or the electron injecting and transporting layer 9.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer and an electron transport layer is formed thereon, and then a substance usable as a cathode is deposited on the organic material layer. . In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The host material of the light emitting layer may be more specifically any one of the following formulas (F-1) to (F-4), but is not limited thereto.

[Formula F-1]

In the above formula (F-1)

Q1 to Q3 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p1 is an integer of 0 to 8, and when p1 is 2 or more, Q1 are the same or different from each other,

[Formula F-2]

In the above formula (F-2)

W1 is O or S,

Q4 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p2 is an integer of 0 to 4, and when p2 is 2 or more, Q4 are the same or different from each other,

Q5 to Q8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and two or more of Q5 to Q8 are bonded to each other to form a substituted or unsubstituted ring Forming,

[Formula F-3]

In Formula F-3,

W2 is O, S or NA '

A ', Q9 and Q10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p3 and p4 are each an integer of 0 to 4, and when p3 and p4 are each 2 or more, the substituents in the parentheses are the same or different from each other,

[Formula F-4]

In the above formula (F-4)

W3 is O or S,

Q11 to Q13 represent hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p5 is an integer of 0 to 4, and when p5 is 2 or more, Q11 are the same or different from each other.

According to one embodiment of the present disclosure, Q1 is hydrogen.

In one embodiment of the present specification, Q2 and Q3 are the same or different and each independently represents a substituted or unsubstituted aryl group.

According to another embodiment, Q2 and Q3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Q2 and Q3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Q2 and Q3 are the same or different and each independently represent an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a substituted or unsubstituted heteroaryl group.

According to another embodiment, Q2 and Q3 are the same or different and each independently represent an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a heteroaryl group substituted with an aryl group.

In another embodiment, Q2 and Q3 are the same or different and are each independently a phenyl group substituted or unsubstituted with a heteroaryl group substituted with an aryl group.

According to another embodiment, Q2 and Q3 are the same or different and each independently a phenyl group substituted or unsubstituted with an aryl group-substituted triazinyl group.

In another embodiment, Q2 and Q3 are the same or different and each independently a phenyl group substituted or unsubstituted with a diphenyltriazinyl group.

In another embodiment, any one of Q2 and Q3 is a phenyl group, and the other is a phenyl group substituted with a diphenyltriazinyl group.

According to one embodiment of the present disclosure, p1 is 0 or 1.

In one embodiment of the present specification, p2 is 0 or 1.

According to one embodiment of the present disclosure, Q4 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another embodiment, Q4 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another embodiment, Q4 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted carbazole group.

In another embodiment, Q4 is selected from the group consisting of hydrogen; heavy hydrogen; A phenyl group substituted with a 2-methylpropenyl group; A biphenyl group; A terphenyl group; Or a carbazole group.

According to one embodiment of the present disclosure, Q5 to Q8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and two or more of Q5 to Q8 are bonded to each other to form a substituted or unsubstituted ring.

In another embodiment, Q5 to Q8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and two or more of Q5 to Q8 are bonded to each other to form a substituted or unsubstituted ring.

According to another embodiment, Q5 to Q8 are the same or different and each independently hydrogen; Or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and two or more of Q5 to Q8 are bonded to each other to form a substituted or unsubstituted ring.

In another embodiment, Q5 to Q8 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted heterocycle, and two or more of Q5 to Q8 are bonded to each other to form a substituted or unsubstituted heterocycle.

According to one embodiment of the present disclosure, Q5 and Q6; Q6 and Q7; Or Q7 and Q8 are bonded to each other to form a substituted or unsubstituted aromatic heterocycle, the remaining substituents being hydrogen; Or a substituted or unsubstituted phenyl group.

According to yet another embodiment, Q5 and Q6; Q6 and Q7; Or Q7 and Q8 are benzofuran substituted or unsubstituted by bonding to each other; Or substituted or unsubstituted benzothiophene, the remaining substituents being hydrogen; Or a substituted or unsubstituted phenyl group.

In yet another embodiment, Q5 and Q6; Q6 and Q7; Or Q7 and Q8 are bonded to each other to form an aryl group; Or benzofuran substituted or unsubstituted with a heterocyclic group; Or an aryl group; Or substituted or unsubstituted benzothiophene with a heterocyclic group, the remaining substituents being hydrogen; Or a substituted or unsubstituted phenyl group.

According to yet another embodiment, Q5 and Q6; Q6 and Q7; Or Q7 and Q8 are a phenyl group which is bonded to each other to be substituted with a 2-methylpropenyl group; A biphenyl group; A terphenyl group; Or benzofuran substituted or unsubstituted with a carbazole group; Or a 2-methylpropenyl group; A biphenyl group; A terphenyl group; Or benzothiophene substituted or unsubstituted with a carbazole group, and the remaining substituents are hydrogen; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, A 'is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another embodiment, A 'is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, A 'is a substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.

In another embodiment, A 'is a biphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A terphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A pyrimidine group substituted or unsubstituted with an aryl group or a heteroaryl group; A dibenzofurane group substituted or unsubstituted with an aryl group or a heteroaryl group; Or a dibenzothiophene group substituted or unsubstituted with an aryl group or a heteroaryl group.

According to another embodiment, A 'is a biphenyl group substituted or unsubstituted with at least one of a dibenzofurane group, a dibenzothiophene group, a carbazole group, and a dibenzoimidazolothiazole group; A terphenyl group substituted or unsubstituted with at least one of a carbazole group, a dibenzothiophene group and a dibenzofurane group; A pyrimidine group substituted or unsubstituted with a carbazole group; A dibenzofurane group substituted or unsubstituted with a dibenzofurane group; Or a dibenzothiophene group substituted or unsubstituted with a dibenzothiophene group.

In one embodiment of the present specification, p3 and p4 are 0 or 1.

According to one embodiment of the present disclosure, Q9 and Q10 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, Q9 and Q10 are the same or different and are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, Q9 and Q10 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, Q9 and Q10 are the same or different and are each independently selected from the group consisting of hydrogen; An aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with an aryl group or a heteroaryl group; Or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with an aryl group or a heteroaryl group.

According to another embodiment, Q9 and Q10 are the same or different from each other, and each independently hydrogen; A phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A terphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A carbazolyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A dibenzofurane group substituted or unsubstituted with an aryl group or a heteroaryl group; A dibenzothiophene group substituted or unsubstituted with an aryl group or a heteroaryl group; Or the following structure.

"는 결합부를 의미한다.In the above structure,

&Quot; means a joining part.

In another embodiment, Q9 and Q10 are the same or different and are each independently selected from the group consisting of hydrogen; A phenyl group substituted or unsubstituted with at least one of a carbazole group, a triphenylenyl group, a dibenzothiophene group and a dibenzofurane group; A biphenyl group substituted or unsubstituted with at least one of a dibenzofurane group and a dibenzothiophene group; Carbazole group; A dibenzofurane group; A dibenzothiophene group; Or the following structure.

According to one embodiment of the present disclosure, p5 is 0 or 1.

In one embodiment of the present disclosure, Q11 is hydrogen.

According to one embodiment of the present disclosure, Q12 is a substituted or unsubstituted aryl group.

According to another embodiment, Q12 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Q12 is a substituted or unsubstituted triphenylenyl group.

According to another embodiment, Q12 is a triphenylenyl group.

In one embodiment of the present specification, Q13 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another embodiment, Q13 is an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with a heteroaryl group; Or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with an aryl group.

According to another embodiment, Q13 is a phenyl group substituted or unsubstituted with a heteroaryl group; A dibenzofurane group substituted or unsubstituted with an aryl group; Or a dibenzothiophene group substituted or unsubstituted with an aryl group.

In another embodiment, Q13 is a phenyl group substituted with a dibenzofurane group or a dibenzothiophene group; A dibenzofurane group; Or a dibenzothiophene group.

According to one embodiment of the present invention, the formulas F-1 to F-4 may be represented by any one of the following structures.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron blocking layer is a layer which prevents electrons from reaching the anode, and a material known in the art such as an amine compound may be used.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

< Manufacturing example >

The process for preparing the material of the present invention begins with the reaction of introducing a silyl group from a variety of halides substituted benzenes as follows. A silyl group is introduced through a halide using LDA (lithium diisopropylamide), the silyl group is substituted with iodine through iodine monochloride, and then the stepwise substituted carbazole is introduced according to the reactivity of the halide . After the step of introducing the substituted carbazole, the final chloride was converted into the boronic ester, and the triazine group was introduced to finally synthesize the compounds of the specific examples.

Manufacturing example  1-1: Synthesis of Compound 1-A

[Reaction Scheme 1-1]

50 g (219.8 mmol) of 1-bromo-5-chloro-2,4-difluorobenzene and 500 mL of tetrahydrofuran were mixed and cooled to -78 deg. 219.8 mmol of lithium diisopropylamide was added, followed by stirring at -78 캜 for 2 hours. 219.8 mmol of trimethylsilyl chloride was added at 0 ° C, and the mixture was stirred at room temperature for 20 hours. After the reaction, ethanol was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. The solid was purified by column chromatography (developing solvent: chloroform / hexane) and then purified by recrystallization with toluene / ethanol (1: 1) to obtain 59.3 g of 1-A (yield: 90%).

MS [M + H] &lt; + &gt; = 300

Manufacturing example  1-2: Synthesis of Compound 1-B

[Reaction Scheme 1-2]

50 g (219.8 mmol) of 1-bromo-5-chloro-2,4-difluorobenzene and 500 mL of tetrahydrofuran were mixed and cooled to -78 deg. 439.6 mmol of lithium diisopropylamide was added, followed by stirring at -78 캜 for 2 hours. Trimethylsilyl chloride (439.6 mmol) was added at 0 ° C, and the mixture was stirred at room temperature for 20 hours. After the reaction, ethanol was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. The solid was purified by column chromatography (developing solvent: chloroform / hexane) and purified by recrystallization with toluene / ethanol (1: 1) to obtain 69.5 g of 1-B (yield: 85%).

MS [M + H] &lt; + &gt; = 371

Manufacturing example  2-1: Synthesis of Compound 2-A

[Reaction Scheme 2-1]

55.4 g (185 mmol) of 1-A and 500 mL of chloroform are mixed and cooled to 0 ° C. 370 mmol of iodine monochloride was added, followed by stirring at 0 캜 for 4 hours. After the reaction, the organic layer was extracted with an aqueous solution of sodium cyanosulfate and purified by column chromatography (developing solvent: chloroform / hexane) and then purified by recrystallization with toluene / ethanol (1: 1) g (95% yield).

MS [M + H] &lt; + &gt; = 353

Manufacturing example  2-2: Synthesis of Compound 2-B

[Reaction Scheme 2-2]

68.8 g (185 mmol) of 1-B and 500 mL of chloroform are mixed and cooled to 0 ° C. 740 mmol of iodine monochloride was added, followed by stirring at 0 캜 for 4 hours. After the reaction, the organic layer was extracted with an aqueous solution of sodium cyanosulfate and purified by column chromatography (developing solvent: chloroform / hexane), followed by recrystallization with toluene / ethanol (1: 1) g (yield: 93%).

MS [M + H] &lt; + &gt; = 479

Manufacturing example  3-1: Synthesis of Compound 3-A

[Reaction Scheme 3-1]

586 g (166 mmol) of 2-A and 166.5 mol of 3,6-dimethyl-9H-carbazole were completely dissolved in 500 mL of toluene, 332 mol of sodium tert-butoxide was added, and tetrakis triphenylphosphine palladium 0.83 mmol, and the mixture was stirred at 80 ° C for 6 hours. The temperature was lowered to room temperature, the salt was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) and column chromatography with tetrahydrofuran: hexane = 1: 5 to obtain 57.9 g of 3-A Yield: 83%).

MS [M + H] &lt; + &gt; = 420

In the above reaction scheme 3-1, various kinds of intermediates other than 3-A were synthesized by using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  3-2: Synthesis of Compound 3-B

[Reaction Scheme 3-2]

79.5 g (166 mmol) of 2-B and 335 mol of 3,6-dimethyl-9H-carbazole were completely dissolved in 500 mL of toluene, 664 mol of sodium tert-butoxide was added, and tetrakis triphenylphosphine palladium 0.83 mmol, and the mixture was stirred at 80 ° C for 6 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) by column with tetrahydrofuran: hexane = 1: 5 to obtain 86.6 g of 3-B Yield: 85%).

MS [M + H] &lt; + &gt; = 613

In the above reaction scheme 3-2, various kinds of intermediates other than 3-B were synthesized by using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  4-1: Synthesis of compound 4-A

[Reaction Scheme 4-1]

3-A 54.7 g (130 mmol) of 3,6-dimethyl-9H-carbazole were dissolved in 450 mL of toluene, 260 mol of sodium tert-butoxide was added, and tetrakis triphenylphosphine palladium 0.65 mmol, and the mixture was stirred at 100 캜 for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by recrystallization from toluene / ethanol (1: 1) to obtain 64.7 g of 4-A Yield: 93%).

MS [M + H] &lt; + &gt; = 535

In the above Scheme 4-1, various kinds of intermediates other than 4-A were synthesized by using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  4-2: Synthesis of compound 4-B

[Reaction Scheme 4-2]

(130 mmol) of 3-B and 130.5 mol of 3,6-dimethyl-9H-carbazole were completely dissolved in 450 mL of toluene, 260 mol of sodium tert-butoxide was added, and tetrakis triphenylphosphine palladium 0.65 mmol, and the mixture was stirred at 100 캜 for 6 hours. After the temperature was lowered to room temperature, the salt was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) and column chromatography with tetrahydrofuran: hexane = 1: 5 to obtain 85.2 g of 4-B Yield 90%).

MS [M + H] &lt; + &gt; = 728

In the above Scheme 4-2, various kinds of intermediates other than 4-B were synthesized by using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  5-1: Synthesis of Compound 5-A

[Reaction Scheme 5-1]

4-A 58.8 g (110 mmol) of 3,6-dimethyl-9H-carbazole and 220.5 mol of 3,6-dimethyl-9H-carbazole were completely dissolved in 400 mL of DMFE, 440 mol of cesium carbonate was added and the mixture was stirred at 100 ° C for 6 hours. After filtration at 60 캜 to remove salts, the mixture was concentrated under reduced pressure and purified by recrystallization with toluene / ethanol (1: 1) to obtain 92.5 g of 5-A (95% yield).

MS [M + H] &lt; + &gt; = 885

In the above reaction scheme 5-1, various kinds of intermediates other than 5-A were synthesized using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  5-2: Synthesis of Compound 5-B

[Reaction Scheme 5-2]

80.5 g (110 mmol) of 4-B and 220.5 mol of 3,6-dimethyl-9H-carbazole were completely dissolved in 400 mL of DMF (DMF, dimethylformamide), 440 mol of cesium carbonate was added, Lt; 0 &gt; C. After filtration at 60 ° C to remove salts, the mixture was concentrated under reduced pressure and purified by recrystallization with toluene / ethanol (1: 1) to obtain 113.9 g of 5-B (yield: 96%).

MS [M + H] &lt; + &gt; = 1078

In the above Scheme 5-2, various kinds of intermediates other than 5-B were synthesized using carbazole in which other substituents on the specific examples were introduced instead of 3,6-dimethyl-9H-carbazole.

Manufacturing example  6-1: Synthesis of Compound 6-A

[Reaction Scheme 6-1]

A mixture of 68.1 g (77 mmol) of 5-A, 400 mL of 1,4-dioxane, 154 mmol of potassium acetate, 84.7 mmol of pinacolacto diborane and 0.77 mmol of tetrakis triphenylphosphine palladium was mixed in a reflux condition for 8 hours Lt; / RTI &gt; After the reaction, water was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. The solid was purified by column chromatography (developing solvent: chloroform) and then purified by recrystallization with ethyl acetate (EA, ethyl acetate) to give 63.9 g of 6-A (yield: 85%).

MS [M + H] &lt; + &gt; = 977

Manufacturing example  6-2: Synthesis of Compound 6-B

[Reaction Scheme 6-2]

5-B was mixed with 83.1 g (77 mmol) of 1,4-dioxane, 154 mmol of potassium acetate, 84.7 mmol of pinacolacto diborane and 0.77 mmol of tetrakis triphenylphosphine palladium, and the mixture was refluxed for 8 hours Lt; / RTI &gt; After the reaction, water was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. The solid was purified by column chromatography (developing solvent: chloroform), and then purified by recrystallization with ethyl acetate (EA, ethyl acetate) to obtain 74.8 g of 6-B (yield: 83%).

MS [M + H] &lt; + &gt; = 1170

Manufacturing example  7-1: Synthesis of Compound 1

[Reaction Scheme 7-1]

19.5 g (20 mmol) of 6-A, 22 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 180 mL of tetrahydrofuran and 60 mL of water are mixed and heated to 60 DEG C . 60 mmol of potassium carbonate and 0.2 mmol of tetrakis triphenylphosphine palladium were added and stirred for 3 hours in a reflux state. After the reaction, ethanol was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. This solid was recrystallized three times with toluene and then purified by sublimation to obtain 15.6 g of Compound 1 (yield: 72%).

MS [M + H] &lt; + &gt; = 1082

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the above Reaction Scheme 7-1, triazine or pyrimidine introduced with another substituent on the specific example may be used to synthesize the substance Respectively.

Manufacturing example  7-2: Synthesis of Compound 2

[Reaction Scheme 7-2]

22 mmol of 6-B, 23.4 g (20 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 180 mL of tetrahydrofuran and 60 mL of water are mixed and heated to 60 ° C . 60 mmol of potassium carbonate and 0.2 mmol of tetrakis triphenylphosphine palladium were added and stirred for 3 hours in a reflux state. After the reaction, ethanol was added to the reaction solution returned to room temperature, and the precipitate was washed successively with pure water and ethanol. This solid was recrystallized three times with toluene and then purified by sublimation to obtain 19.6 g of Compound 2 (yield: 77%).

MS [M + H] &lt; + &gt; = 1275

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Scheme 7-2, triazine or pyrimidine with other substituents introduced in the specific examples may be used to synthesize Respectively.

< Experimental Example  1>

In this Experimental Example, an organic light emitting device was fabricated by including the host material (m-CBP) having a triplet value of 2.5 eV or more in Formula 1 according to one embodiment of the present invention to evaluate its characteristics.

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. Each thin film was laminated on the prepared ITO transparent electrode by a vacuum deposition method with a degree of vacuum of 5.0 Х 10 ^{- 4} ㎫. First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 Å to form a hole injection layer.

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

([1,1'-biphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4-yl ) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (EB1) (100 Å) was vacuum deposited thereon to form an electron blocking layer.

Subsequently, the following m-CBP and 4CzIPN were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 70:30 to form a light emitting layer.

Compound HB1 was vacuum deposited on the light emitting layer to a thickness of 100 Å to form a hole blocking layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

Experimental Example  1-1 to 1-10

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound of Table 1 was used instead of the compound 4CzIPN in Experimental Example 1.

[Compound 3] [Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9] [Compound 10]

compare Experimental Example  1-1 to 1-4

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following compounds T1 to T4 were used instead of the compound 4CzIPN in Experimental Example 1.

The results shown in Table 1 below were obtained when current was applied to the organic light-emitting devices manufactured by Experimental Examples 1-1 to 1-10 and Comparative Examples 1-1 to 1-4.

division compound
(Light emitting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 4CzIPN 4.8 25 (0.34, 0.62) Experimental Example 1-1 Compound 1 3.9 35 (0.33, 0.63) Experimental Example 1-2 Compound 2 4.0 33 (0.34, 0.63) Experimental Example 1-3 Compound 3 4.2 30 (0.33, 0.64) Experimental Examples 1-4 Compound 4 4.3 31 (0.33, 0.65) Experimental Examples 1-5 Compound 5 4.2 31 (0.34, 0.61) Experimental Example 1-6 Compound 6 4.4 30 (0.32, 0.62) Experimental Example 1-7 Compound 7 4.1 32 (0.33, 0.64) Experimental Examples 1-8 Compound 8 4.1 31 (0.31, 0.62) Experimental Examples 1-9 Compound 9 4.3 30 (0.32, 0.62) Experimental Example 1-10 Compound 10 4.2 32 (0.33, 0.64) Comparative Example 1-1 T1 5.2 16 (0.35, 0.65) Comparative Example 1-2 T2 5.3 17 (0.39, 0.58) Comparative Example 1-3 T3 5.1 20 (0.38, 0.59) Comparative Example 1-4 T4 5.0 19 (0.36, 0.61)

As shown in Table 1, in all of the devices of Experimental Examples 1-1 to 1-10 using the compound having the structure of Formula 1 as a core, the voltage was lower than that of the device using the compound 4CzIPN in Experimental Example 1, Results were obtained.

Compared with the comparative examples 1-1 to 1-4, the structure of the present invention is more favorable in terms of voltage and efficiency than that of carbazole in which the unsubstituted carbazole is introduced or substituted, It was found to be improved.

As shown in Table 1, it was confirmed that the compound of the present invention is applicable to a delayed fluorescent organic light emitting device because of its excellent light emitting ability and high color purity.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electronic blocking layer
8: hole blocking layer
9: Electron injection and transport layer

Claims (9)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X1 to X3 are the same or different and each independently N or CR, and at least two of X1 to X3 are N,
R is hydrogen; Or a substituted or unsubstituted aryl group,
R2 and R3 are the same or different and are each independently a substituted or unsubstituted aryl group,
R 1 is a carbazole group substituted with an alkyl group or a silyl group; A triazinyl group substituted with an aryl group; Or a pyrimidinyl group substituted with an aryl group,
n is 4 or 5, and 4 or 5 R1's are the same or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the general formulas (2) and (3)
R1 and n are the same as defined in the above formula (1)
R11 is hydrogen; Or a substituted or unsubstituted aryl group,
R12 to R15 are the same or different and each independently represents a substituted or unsubstituted aryl group. The method of claim 2,
R 12 to R 15 are the same or different and each independently represents a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group. The method according to claim 1,
(1) is represented by any one of the following structures:

. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 4. The organic light- Light emitting element. The method of claim 5,
Wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound of the formula (1). The method of claim 5,
Wherein the organic material layer comprises an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound of the formula (1). The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1. [6] The organic light emitting diode according to claim 5, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1 as a dopant.

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