KR20200025382A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to: a novel compound having excellent thermal stability, electron transporting ability, and luminescent ability; and to an organic electroluminescent device having improved properties such as luminous efficiency, driving voltage, lifespan, etc., by containing the compound in at least one organic material layer. The organic electroluminescent device containing the compound in an organic material layer of the present invention has significantly improved aspects such as luminous performance, driving voltage, lifespan, efficiency, etc., thereby being able to be effectively applied to a full color display panel, etc.

Description

Organic compound and organic electroluminescent device using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability and electron transport ability, and including the same in one or more organic material layers, such as characteristics such as luminous efficiency, driving voltage and lifetime. This improved organic electroluminescent device.

The study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene monocrystals in 1965, based on Bernanose's observation of organic thin film emission in the 1950s. By (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed. Since then, in order to make high-efficiency, high-life organic EL devices, the development has been made in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emission color. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, a host / dopant system may be used as the light emitting material in order to increase luminous efficiency through an increase in color purity and energy transfer. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve the luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.

Until now, as the hole injection layer, the hole transport layer, the hole blocking layer, the electron transport layer, NPB, BCP, Alq3 and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. . Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) _2, such as blue, green, and red dopant materials. 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but are not satisfactory in terms of lifespan in organic EL devices due to low glass transition temperature and very poor thermal stability. Therefore, development of the organic material layer material which is excellent in performance is calculated | required.

Republic of Korea Patent Publication No. 2015-0031649

An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and can be used as a phosphorescent material and / or a highly efficient electron transport layer material having excellent thermal stability and luminescence performance.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage, high luminous efficiency, and has an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

In Chemical Formula 1,

X is O or S,

l is an integer of 1 to 3,

R ₁ to R ₅ are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ ˜C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ aryl of C ₆₀ boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or they form a contiguous group fused ring You can,

Ar ₁ to Ar ₃ are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ ˜C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ is selected from the group consisting of C ₆₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,

Provided that at least one of Ar ₁ to Ar ₃ is an aryl group of C ₆ to C ₆₀ ,

The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups and arylsilyls of Ar ₁ to Ar ₃ and R ₁ to R ₅ A group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl amine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ In If selected, and may be substituted with one or more substituents, wherein the substituents have the plurality, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is represented by the formula (1) It provides an organic electroluminescent device comprising a compound.

Since the compound of the present invention has excellent thermal stability, electron transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifespan, and efficiency are greatly improved.

Hereinafter, the present invention will be described in detail.

<New organic compound>

The present invention provides a novel compound that can be used as a phosphorescent light emitting material having excellent thermal stability and light emitting ability, and at the same time have excellent electron transporting ability and can be used as a highly efficient electron transporting layer material.

Specifically, the novel compound according to the present invention comprises two dibenzoic moieties that are the same or different from each other, and at least one arylene-based linker (L) and a triazine ring are bonded between them to form a basic skeleton. In particular, a diazinefuran and / or a dibenzothiophene as a basic skeleton, and a triazine ring, which is an electron withdrawing group (EWG), is bonded to an intermediate core therebetween, and the triazine is centered. In one side is a substituted or unsubstituted dibenzofuran is a linker (L) is bonded at position 4, the opposite side is a structure in which a substituted or unsubstituted dibenzofuran or dibenzothiophene bonded directly without a linker Has This results in asymmetry based on the long axis of the molecule.

The compound of the present invention described above has high triplet energy (T1) because dibenzofuran is not directly bonded to triazine, which is a kind of EWG group having high electron absorbing properties. The high triplet energy as described above can prevent the exciton generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. In addition, the number of excitons contributing to light emission in the light emitting layer may be increased, and thus, the light emitting efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. In the present invention, by using a high T1 (triplet) and a core having excellent electron transporting ability, the electron and hole can be easily transferred, and the luminous efficiency can be greatly enhanced.

In addition, in the present invention, as the linker is introduced at position 4, which is an active site of dibenzofuran, the stability of the molecule may be increased, and the steric hindrance of the compound may cause thermal stability. May increase. In particular, when at least one aryl group is introduced at position 6 of the dibenzo-based moiety such as dibenzofuran and dibenzothiophene, it may exhibit a synergy effect in thermal stability. Specifically, when at least one aryl group is introduced at position 6 of the dibenzoic moiety, structural steric hindrance may occur structurally. Such tilted structures have a relatively high thermal stability effect. In addition, the decomposition temperature (Td) is lowered to be purified at a relatively low temperature during sublimation purification has excellent thermal stability.

In addition, the compound represented by Chemical Formula 1 includes two dibenzo-based moieties, and at least one linker (L) and a triazine ring are bonded between them to form a basic skeleton, all of which are meta-meta (meta- meta) position. These meta-meta bonds have a twisted structure based on the long axis of the molecule, thus extending the distance between these moieties to minimize the interaction between them and the physical and electrochemical properties of the compound itself. Increase stability. In addition, the meta-meta bond is effective in inhibiting crystallization of the organic layer, compared to the linking group connected by ortho-para, or meta-para, and the like. An organic electroluminescent device comprising can greatly improve durability and lifespan characteristics.

Furthermore, the compound represented by Chemical Formula 1 has structural asymmetry as the linker (L) is present only on one side. Such asymmetry of the molecule may inhibit crystallization to improve processability of the compound represented by Formula 1 and durability of the device.

In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent green n-type host and / or a phosphorescent red host, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer life than a conventional light emitting host material is manufactured. In addition, it is possible to manufacture a full color display panel with improved efficiency and long life.

As described above, the compound represented by Chemical Formula 1 may be used as one of materials of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic material layers of the organic electroluminescent device, because of excellent light emission characteristics. It is preferably used as a material of the light emitting layer of green phosphorescence and red phosphorescence, or an electron transport layer material. Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green, red, blue phosphorescent host material), electron transport layer / injection layer material, light emitting auxiliary layer material, It can be used as an electron transport auxiliary layer material, more preferably a light emitting layer material, an electron transport layer material, an electron transport auxiliary layer material. The organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

Compound represented by the formula (1) according to the present invention, at least one arylene linker and triazine is bonded between two dibenzo moieties that are the same or different from each other, the above-mentioned two dibenzo moieties and triazine groups It is characterized by a structure in which at least one or more aryl groups are introduced.

In Formula 1, X introduced into the dibenzoic moiety may be O or S. For example, it may be a dibenzofuran (X = O) moiety or a dibenzothiophene (X = S) moiety.

In addition, in the compound of Formula 1, Ar ₁ to Ar ₃ may be introduced into two dibenzo-based moieties and triazine rings, respectively. The Ar ₁ to Ar ₃ are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, nuclear atom 5-60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C group _{of 6} to arylboronic of C _60, C ₁ ~ C ₄₀ there may be selected from phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and the group consisting of C ₆ to C ₆₀ with an aryl amine of the. However, at least one of Ar ₁ to Ar ₃ has a C ₆ ~ C ₆₀ aryl group.

For example, when at least one of Ar ₁ to Ar ₃ is an aryl group, they may be the same as or different from each other, and each of them may be selected from the following structural formulas.

Although not represented in the above-described structural formula, at least one or more substituents known in the art (eg, the same as defined in R ₁ to R ₅ ) may be substituted.

In addition, R ₁ to R ₅ introduced in Formula 1 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 Heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of these It may be combined with adjacent groups to form conventional condensed rings known in the art. Specifically, R ₁ to R ₅ are the same as or different from each other, and each independently composed of hydrogen, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms It is preferably selected from the group.

l is an integer of 1-3, Preferably it is 1 or 2. For example, it may be a phenylene group or a biphenylene group.

The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups and arylsilyls of Ar ₁ to Ar ₃ and R ₁ to R ₅ A group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl amine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ In If selected, and may be substituted with one or more substituents, wherein the substituents have the plurality, they may be the same or different from each other.

The compound of Formula 1 according to the present invention may be variously modified depending on the bonding position of the R ₃ containing compound, which is an arylene-based linker, and a dibenzo-based moiety including Ar ₃ . According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be embodied in any one of the following Chemical Formulas 2 to 9.

In Chemical Formulas 2 to 9,

X, R ₁ to R ₅ and Ar ₁ to Ar ₃ are the same as defined in Chemical Formula 1.

In addition, the compound of Formula 1 according to the present invention can be variously modified depending on the position of Ar ₁ introduced into the dibenzofuran moiety. According to an embodiment of the present invention, the compound represented by Chemical Formula 1 may be embodied in any one of the following Chemical Formulas 10 to 13.

X, R ₁ to R ₅ , Ar ₁ to Ar ₃ and l are the same as defined in Chemical Formula 1.

Among the compounds represented by the above Chemical Formulas 10 to 13, a linker (eg, an R ₃ -containing arylene group) is introduced at position 4 of dibenzofuran, and at the same time, the compound represented by Formula 10 having Ar ₁ introduced at position 6 Compounds are preferred.

Specifically, position 6 of dibenzofuran is the active site. Since the compound represented by the above formula (10) blocks the active position of dibenzofuran through substitution, it shows an excellent effect in terms of structural stability compared to the compound substituted at other positions (eg, formulas 11 to 13). In addition, when the substitution at the sixth position, because the steric hindrance is the largest it can have a high thermal stability.

Meanwhile, the compound represented by Chemical Formula 1 of the present invention may have a meta-meta (meta-meta) bonding structure in a molecular structure. Specifically, for the triazine ring containing Ar ₂ , the ring containing X and the ring containing R ₃ are bonded to each other in a meta position, and with respect to the ring containing R ₃ , Ar ₂ The triazine ring and the ring including Ar ₁ may be bonded to each other in a meta position. As described above, the compound having a meta-meta-bonded structure has a twisted structure that is zigzag-shaped based on the long axis of the molecule, thereby minimizing the interaction between these moieties and the physical properties of the compound itself. It can increase the electrochemical stability. Such compounds may be more embodied by the following formula (14).

In Chemical Formula 14,

X, R ₁ to R ₅ , Ar ₁ to Ar ₃ and l are the same as defined in Chemical Formula 1.

As a preferable example of the compound represented by any one of Formulas 2 to 14, X may be O or S.

At least one of Ar ₁ to Ar ₃ may be a C ₆ ~ C ₆₀ aryl group, specifically, two or more of Ar ₁ to Ar ₃ , or all three may be an aryl group. In this case, when at least two or more of Ar ₁ to Ar ₃ is an aryl group, a plurality of aryl groups may be the same or different from each other.

R ₁ to R ₅ may each independently be selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, in particular an arylene-based R ₃ introduced into the linker (L) may be a C ₆ ~ C ₆₀ aryl group, or a heteroaryl group having 5 to 60 nuclear atoms. L may also be 1 or 2.

The compound represented by the general formula (1) of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by P-1 to P-188. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.

"Alkyl" as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

In the present invention, "arylamine" refers to an amine substituted with aryl having 6 to 40 carbon atoms.

"Cycloalkyl" as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" as used herein means monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 Compound. Specifically, the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, an electron transport auxiliary layer.

The light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, wherein the host material may include the compound of Formula 1 above. In addition, the light emitting layer of the present invention may further include a compound known in the art other than the compound of Formula 1 as a host.

When the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light emitting layer is increased, and thus the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved. Specifically, the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of the light emitting layer having high efficiency.

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a light emitting layer, more preferably a phosphorescent host May include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic EL device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1 above. have.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like.

In addition, the positive electrode material may use any positive electrode material known in the art without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

In addition, the negative electrode material may use any negative electrode material known in the art without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art can be used without limitation.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following Examples are merely to illustrate the invention, the present invention is not limited by the following Examples.

Preparation Example 1 Synthesis of Core-1

Step 1 Synthesis of 4- (3-bromophenyl) dibenzo [b, d] furan

Dibenzo [b, d] furan-4-ylboronic acid (212 g, 1,000 mmol) with 1-bromo-3-iodobenzene (290 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol), NaOH (120 g, 3,000 mmol) was added to 5,000 ml THF and 2,000 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (3-bromophenyl) dibenzo [b, d] furan (242 g, yield 75%).

¹ H-NMR: δ 7.32 (d, 1H), 7.38 (t, 2H), 7.40 (t, 1H), 7.46 (d, 2H), 7.56 (d, 1H), 7.66 (d, 1H), 7.81 ( d, 1H), 7.85 (d, 1H), 7.89 (d, 1H)

<Step 2> Synthesis of Core-1

4- (3-bromophenyl) dibenzo [b, d] furan (242 g, 748 mmol) and Pd (dppf) Cl ₂ (21.9 g, 30 mmol), Pinacol diboron (227 g, 898 mmol), KOAc (220 g , 2,244 mmol) was added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-1 (250 g, yield 90%).

¹ H-NMR: δ 1.24 (s, 12H), 7.32 (d, 1H), 7.38 (t, 2H), 7.51 (t, 1H), 7.52 (d, 1H), 7.66 (m, 2H), 7.71 ( d, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.89 (d, 1H)

Preparation Example 2 Synthesis of Core-2

<Step 1> Synthesis of 4- (3-bromophenyl) -6-phenyldibenzo [b, d] furan

(6-Phenyldibenzo [b, d] furan-4-yl) boronic acid (288 g, 1,000 mmol) and 1-bromo-3-iodobenzene (290 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol) and NaOH (120 g, 3,000 mmol) were added to 5,000 ml THF and 2,000 ml H ₂ O, and the mixture was stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (3-bromophenyl) -6-phenyldibenzo [b, d] furan (350 g, yield 88%).

¹ H-NMR: δ 7.38 (t, 2H), 7.40 (m, 2H), 7.46 (d, 2H), 7.52 (m, 4H), 7.56 (d, 1H), 7.81 (d, 2H), 7.85 ( d, 2H)

<Step 2> Synthesis of Core-2

4- (3-bromophenyl) dibenzo [b, d] furan (350 g, 877 mmol) and Pd (dppf) Cl ₂ (25.7 g, 35 mmol), Pinacol diboron (244 g, 964 mmol), KOAc (258 g , 2,629 mmol) was added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-2 (340 g, yield 87%).

¹ H-NMR: δ 1.24 (s, 12H), 7.38 (m, 2H), 7.41 (m, 1H), 7.52 (m, 6H), 7.66 (s, 1H), 7.71 (d, 1H), 7.81 ( d, 2H), 7.85 (d, 2H)

Preparation Example 3 Synthesis of Core-3

Step 1 Synthesis of 4- (4-bromophenyl) -6-phenyldibenzo [b, d] furan

(6-Phenyldibenzo [b, d] furan-4-yl) boronic acid (288 g, 1,000 mmol) and 1-bromo-4-iodobenzene (290 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol) and NaOH (120 g, 3,000 mmol) were added to 5,000 ml THF and 2,000 ml H ₂ O, and the mixture was stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (4-bromophenyl) -6-phenyldibenzo [b, d] furan (360 g, 90% yield).

¹ H-NMR: δ 7.38 (t, 2H), 7.40 (m, 1H), 7.52 (m, 4H), 7.53 (d, 2H), 7.66 (d, 2H), 7.81 (d, 2H), 7.85 ( d, 2H)

<Step 2> Synthesis of Core-3

4- (4-bromophenyl) dibenzo [b, d] furan (350 g, 877 mmol) and Pd (dppf) Cl ₂ (25.7 g, 35 mmol), Pinacol diboron (244 g, 964 mmol), KOAc (258 g , 2,629 mmol) was added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-3 (335 g, yield 86%).

¹ H-NMR: δ 1.24 (s, 12H), 7.38 (m, 2H), 7.41 (m, 1H), 7.52 (m, 4H), 7.79 (d, 2H), 7.81 (d, 4H), 7.85 ( d, 2H)

Preparation Example 4 Synthesis of Core-4

Step 1 Synthesis of 4- (5-Bromo- [1,1'-biphenyl] -3-yl) dibenzo [b, d] furan

Dibenzo [b, d] furan-4-ylboronic acid (212 g, 1,000 mmol) with 3-bromo-5-iodo-1,1'-biphenyl (359 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol) and NaOH (120 g, 3,000 mmol) were added to 5,000 ml THF and 2,000 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer, where the water was removed, and then purified by column chromatography, to obtain 4- (5-Bromo- [1,1'-biphenyl] -3-yl) dibenzo [b, d] furan (350 g, yield 88%). )

¹ H-NMR: δ 7.32 (m, 2H), 7.38 (t, 1H), 7.42 (m, 3H), 7.52 (m, 4H), 7.64 (s, 1H), 7.66 (d, 1H), 7.81 ( d, 1H), 7.85 (d, 1H), 7.89 (d, 1H)

<Step 2> Synthesis of Core-4

4- (5-Bromo- [1,1'-biphenyl] -3-yl) dibenzo [b, d] furan (350 g, 877 mmol) and Pd (dppf) Cl ₂ (25.7 g, 35 mmol), Pinacol diboron (244 g, 964 mmol) and KOAc (258 g, 2,629 mmol) were added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-4 (328 g, yield 83%).

¹ H-NMR: δ 1.24 (s, 12H), 7.32 (t, 1H), 7.38 (m, 2H), 7.42 (m, 1H), 7.52 (m, 4H), 7.62 (s, 2H), 7.66 ( d, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.89 (m, 2H)

Preparation Example 5 Synthesis of Core-5

<Step 1> Synthesis of 4- (5-Bromo- [1,1'-biphenyl] -3-yl) -6-phenyldibenzo [b, d] furan

(6-Phenyldibenzo [b, d] furan-4-yl) boronic acid (288 g, 1,000 mmol) with 3-bromo-5-iodo-1,1'-biphenyl (359 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol) and NaOH (120 g, 3,000 mmol) were added to 5,000 ml THF and 2,000 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (5-Bromo- [1,1'-biphenyl] -3-yl) -6-phenyldibenzo [b, d] furan (410 g, Yield 86%).

¹ H-NMR: δ 7.32 (m, 2H), 7.38 (t, 1H), 7.42 (m, 4H), 7.52 (m, 8H), 7.64 (s, 1H), 7.66 (d, 1H), 7.81 ( d, 1H), 7.85 (d, 1H), 7.89 (d, 1H)

<Step 2> Synthesis of Core-5

4- (5-Bromo- [1,1'-biphenyl] -3-yl) -6-phenyldibenzo [b, d] furan (410 g, 862 mmol) and Pd (dppf) Cl ₂ (25.2 g, 34 mmol ), Pinacol diboron (240 g, 949 mmol) and KOAc (254 g, 2,587 mmol) were added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-5 (380 g, 84% yield).

¹ H-NMR: δ 1.24 (s, 12H), 7.32 (t, 1H), 7.38 (m, 2H), 7.42 (m, 2H), 7.52 (m, 8H), 7.62 (s, 2H), 7.66 ( d, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.89 (m, 2H)

Preparation Example 6 Synthesis of Core-6

<Step 1> Synthesis of 4- (6-Bromodibenzo [b, d] furan-4-yl) benzonitrile

4,6-Dibromodibenzo [b, d] furan (326 g, 1,000 mmol) with (4-cyanophenyl) boronic acid (147 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ (46 g, 40 mmol), NaOH ( 120 g, 3,000 mmol) was added to 5,000 ml THF and 2,000 ml H ₂ O, and the mixture was stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (6-Bromodibenzo [b, d] furan-4-yl) benzonitrile (210 g, yield 60%).

¹ H-NMR: δ 7.21 (t, 1H), 7.36 (d, 1H), 7.38 (t, 1H), 7.84 (m, 7H)

<Step 2> Synthesis of 4- (6- (3-Chlorophenyl) dibenzo [b, d] furan-4-yl) benzonitrile

4- (6-Bromodibenzo [b, d] furan-4-yl) benzonitrile (210 g, 603 mmol) and (3-chlorophenyl) boronic acid (94 g, 603 mmol) and Pd (PPh ₃ ) ₄ (28 g , 24 mmol) and NaOH (72 g, 1,809 mmol) were added to 3,000 ml THF and 1,500 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain 4- (6- (3-Chlorophenyl) dibenzo [b, d] furan-4-yl) benzonitrile (180 g, 79% yield).

¹ H-NMR: δ 7.21 (t, 1H), 7.36 (d, 1H), 7.38 (t, 1H), 7.40 (d, 1H), 7.45 (t, 2H), 7.84 (m, 7H), 8.01 ( s, 1 H)

<Step 3> Synthesis of Core-6

4- (6- (3-Chlorophenyl) dibenzo [b, d] furan-4-yl) benzonitrile (180 g, 474 mmol) and Pd (dppf) Cl ₂ (13.9 g, 19 mmol), Pinacol diboron (132 g , 521 mmol) and KOAc (140 g, 1,422 mmol) were added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-6 (190 g, yield 73%).

¹ H-NMR: δ 1.24 (s, 12H), 7.21 (t, 1H), 7.36 (d, 1H), 7.38 (t, 1H), 7.52 (m, 2H), 7.66 (s, 1H), 7.71 ( d, 1H), 7.84 (m, 7H)

Preparation Example 7 Synthesis of Core-7

<Step 1> Synthesis of 3- (3-bromo-5- (6-phenyldibenzo [b, d] furan-4-yl) phenyl) pyridine

(6-Phenyldibenzo [b, d] furan-4-yl) boronic acid (288 g, 1,000 mmol) and 3- (3,5-dibromophenyl) pyridine (313 g, 1,000 mmol) and Pd (PPh ₃ ) ₄ ( 46 g, 40 mmol) and NaOH (120 g, 3,000 mmol) were added to 5,000 ml THF and 2,000 ml H ₂ O, followed by stirring at 75 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with Ethyl acetate and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography. 3- (3-bromo-5- (6-phenyldibenzo [b, d] furan-4-yl) phenyl) pyridine (410 g, yield 87% )

¹ H-NMR: δ 7.38 (t, 2H), 7.42 (m, 3H), 7.52 (m, 4H), 7.57 (t, 1H), 7.64 (s, 1H), 7.81 (d, 2H), 7.85 ( d, 2H), 8.42 (d, 1H), 8.70 (d, 1H), 9.24 (s, 1H)

<Step 2> Synthesis of Core-7

3- (3-bromo-5- (6-phenyldibenzo [b, d] furan-4-yl) phenyl) pyridine (410 g, 861 mmol) and Pd (dppf) Cl ₂ (25.2 g, 34 mmol), Pinacol diboron (240 g, 949 mmol) and KOAc (254 g, 2,587 mmol) were added to 2,000 ml DMF and stirred at 110 ° C. for 8 hours. After completion of the reaction, H ₂ O was added, and extracted with Ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain Core-7 (370 g, yield 82%).

¹ H-NMR: δ 1.24 (s, 12H), 7.38 (t, 2H), 7.42 (m, 1H), 7.52 (m, 4H), 7.57 (t, 1H), 7.62 (s, 2H), 7.81 ( d, 2H), 7.85 (d, 2H), 7.88 (s, 1H), 8.42 (d, 1H), 8.70 (d, 1H), 9.24 (s, 1H)

Synthesis Example 1 Synthesis of P-1

Core-1 (37 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine (37 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-1 (44 g, yield 75%).

[LCMS]: 581

Synthesis Example 2 Synthesis of P-11

Core-2 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine (37 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-11 (44 g, yield 67%).

[LCMS]: 657

Synthesis Example 3 Synthesis of P-29

Core-3 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine (37 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-29 (31 g, yield 47%).

[LCMS]: 657

Synthesis Example 4 Synthesis of P-37

Core-4 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6- d5 -phenyl-1,3,5-triazine (38 g, 100 mmol ) And Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-37 (42 g, yield 64%).

[LCMS]: 662

Synthesis Example 5 Synthesis of P-39

Core-4 (45 g, 100 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6- (dibenzo [b, d] thiophen-3-yl) -1, 3,5-triazine (45 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O at 75 ° C. Stir for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized from toluene to obtain P-39 (62 g, yield 85%).

[LCMS]: 733

Synthesis Example 6 Synthesis of P-41

Core-2 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (37 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-41 (58 g, yield 88%).

[LCMS]: 657

Synthesis Example 7 Synthesis of P-96

Core-4 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (36 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-96 (56 g, yield 87%).

[LCMS]: 641

Synthesis Example 8 Synthesis of P-115

Core-5 (52 g, 100 mmol), 2-chloro-4-phenyl-6- (6-phenyldibenzo [b, d] furan-4-yl) -1,3,5-triazine (43 g, 100 mmol ) And Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-115 (61 g, yield 77%).

[LCMS]: 793

Synthesis Example 9 Synthesis of P-131

Core-2 (45 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (36 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-131 (50 g, yield 78%).

 [LCMS]: 641

Synthesis Example 10 Synthesis of P-134

Core-2 (45 g, 100 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6- (dibenzo [b, d] furan-3-yl) -1, 3,5-triazine (43 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O at 75 ° C. Stir for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized from toluene to obtain P-134 (61 g, yield 85%).

[LCMS]: 717

Synthesis Example 11 Synthesis of P-182

Core-6 (47 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (37 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-182 (38 g, yield 56%).

[LCMS]: 682

Synthesis Example 12 Synthesis of P-185

Core-7 (52 g, 100 mmol), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (36 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 ° C. for 8 hours. After completion of the reaction, the produced solid was dissolved in Toluene after the filter and filtered through Silica. Toluene was concentrated and recrystallized with toluene to obtain P-185 (47 g, yield 65%).

[LCMS]: 718

[Examples 1 to 12] Fabrication of Green Organic EL Devices

Compounds P-1 to P-185 synthesized in Synthesis Examples 1 to 12 were each subjected to high purity sublimation purification by a commonly known method, and then green organic EL devices were manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / P-1 to P-185 each compound + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) / Alq on the thus prepared ITO transparent electrode _An organic EL device was fabricated by stacking ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, BCP, 1 and 2 are as follows.

[Comparative Examples 1 to 3] Fabrication of Green Organic EL Device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP, 1, and 2 were used instead of the compound P-1 as the light emitting host material when the emission layer was formed.

[Evaluation Example 1]

For each of the green organic EL devices fabricated in Examples 1 to 12 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. It was.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 P-1 4.81 516 45.5 Example 2 P-11 4.73 516 46.5 Example 3 P-29 4.55 516 48.1 Example 4 P-37 4.51 516 46.0 Example 5 P-39 4.77 516 51.2 Example 6 P-41 4.51 516 53.1 Example 7 P-96 4.41 516 48.2 Example 8 P-115 4.58 516 49.2 Example 9 P-131 4.55 516 55.5 Example 10 P-134 4.76 516 48.1 Example 11 P-182 4.54 516 58.0 Example 12 P-185 4.78 516 58.7 Comparative Example 1 CBP 6.93 516 30.2 Comparative Example 2 One 5.92 516 31.5 Comparative Example 3 2 5.90 516 32.5

As shown in Table 1, the green organic EL devices of Examples 1 to 12, which use the compounds P-1 to P-185 according to the present invention as the light emitting layer of the green organic EL device, are conventionally referred to as CBP, compounds 1 and 2 When compared with the green organic electroluminescent element of Comparative Examples 1-3 which were used, it turned out that it shows more excellent performance in terms of efficiency and a drive voltage.

Meanwhile, the P-1 compound and the P-11 compound of the present application used in Examples 1 and 2 differ in the presence or absence of an aryl group introduced at position 6, the active site of dibenzofuran, and have the same chemical structure. Has In fact, Example 2, which includes a P-11 compound having an aryl group introduced at position 6 of dibenzofuran, has better performance in terms of driving voltage and current efficiency than Example 1, which includes P-1 having no aryl group introduced therein. Indicates. This is because the position 6 of the active position of dibenzofuran is blocked by a substitution, and thus, the structural stability is significantly increased, and it may be determined that the physical properties are better through the largest steric hindrance.

Examples 13 to 24 Fabrication of Blue Organic Electroluminescent Devices

Compounds P-1 to P-185 synthesized in the above synthesis example were subjected to high purity sublimation purification by a commonly known method, and then blue organic electroluminescent devices were manufactured as follows.

First, the glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then washed the substrate using UV for 5 minutes. The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / electron transport layer material of Table 2 below (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.

Comparative Example 4 Fabrication of Blue Organic Electroluminescent Device

A blue organic EL device was manufactured in the same manner as in Example 13, except that Alq 3 was used instead of compound P-1 as the electron transporting layer material.

Comparative Example 5 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound T-1, instead of Compound P-1, was used as the electron transporting layer material.

Comparative Example 6 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound T-2, instead of Compound P-1, was used as the electron transporting layer material.

The structures of NPB, AND, Alq 3, T-1, and T-2 used in Examples 13 to 24 and Comparative Examples 4 to 6 are as follows.

[Evaluation Example 2]

For each of the blue organic EL devices manufactured in Examples 13 to 24 and Comparative Examples 4 to 6, a driving voltage, a current efficiency, and a light emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below. Shown in

Sample Electron transport layer material Driving voltage
(V) Luminous Peak
(nm) Current efficiency
(cd / A) Example 13 P-1 3.9 454 8.0 Example 14 P-11 3.5 456 8.9 Example 15 P-29 3.8 457 8.3 Example 16 P-37 3.7 452 8.6 Example 17 P-39 4.3 455 8.5 Example 18 P-41 3.7 452 8.3 Example 19 P-96 3.8 453 7.7 Example 20 P-115 3.9 454 7.8 Example 21 P-131 4.0 455 7.9 Example 22 P-134 4.2 456 6.0 Example 23 P-182 3.7 456 8.8 Example 24 P-185 3.6 456 9.0 Comparative Example 4 Alq ₃ 5.4 458 5.5 Comparative Example 5 T-1 5.1 459 5.1 Comparative Example 6 T-2 5.3 458 5.0

As shown in Table 1, the blue organic electroluminescent device of Examples 13 to 24 using the compounds P-1 to P-185 synthesized in the above Synthesis Example in the electron transporting layer, Comparative Example 4 using the conventional Alq3 in the electron transporting layer Compared with the blue organic EL device, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.

In addition, the blue organic electroluminescent devices of Examples 13 to 24 using the compounds P-1 to P-185 synthesized in the above Synthesis Example have a meta-meta (m, m-) bond in the molecular structure, Compared with the blue organic electroluminescent devices of Comparative Examples 5 and 6, in which a compound having p, p-biphenylene or m, p-biphenylene is used for the electron transport layer, it has excellent performance in terms of driving voltage, emission peak, and current efficiency. It could be seen that.

Claims (10)

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

In Chemical Formula 1,
X is O or S,
l is an integer of 1 to 3,
R ₁ to R ₅ are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ ˜C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ aryl of C ₆₀ boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or they form a contiguous group fused ring You can,
Ar ₁ to Ar ₃ are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ ˜C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ doedoe C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ selected from the group consisting of an arylamine C in _60,
Provided that at least one of Ar ₁ to Ar ₃ is an aryl group of C ₆ to C ₆₀ ,
The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups and arylsilyls of Ar ₁ to Ar ₃ and R ₁ to R ₅ A group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl amine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ In If selected, and may be substituted with one or more substituents, wherein the substituents have the plurality, they may be the same or different from each other. The method of claim 1,
Ar ₁ to Ar ₃ are each selected from the following structural formulas.

The method of claim 1,
The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2 to 9.
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Chemical Formulas 2 to 9,
X, R ₁ to R ₅ , Ar ₁ to Ar ₃ are each as defined in claim 1. The method of claim 1,
The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 10 to 13.
[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In Chemical Formulas 10 to 13,
X, R ₁ to R ₅ , Ar ₁ to Ar ₃ , and l are each as defined in claim 1. The method of claim 1,
In Formula 1, for the triazine ring including Ar ₂ , the ring containing X and the ring containing R ₃ are bonded to each other in a meta position,
With respect to the ring containing R ₃ , the triazine ring containing Ar ₂ and the ring containing Ar ₁ are bonded to each other in a meta position. The method of claim 1,
Compound represented by Formula 1 is a compound represented by the following formula (14).
[Formula 14]

In Chemical Formulas 10 to 13,
X, R ₁ to R ₅ , Ar ₁ to Ar ₃ , and l are each as defined in claim 1. The method of claim 1,
R ₃ is a C ₆ ~ C ₃₀ aryl group or a heteroaryl group of 5 to 30 nuclear atoms,
Aryl and heteroaryl groups of said R _3, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, may be substituted by one substituent at least one selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl amine of the C ₆₀ of, Wherein when the substituents are plural, they are the same or different from each other. An organic material comprising an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises the compound according to any one of claims 1 to 7. EL device. The method of claim 8,
The organic material layer comprising the compound is selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer. The method of claim 8,
The light emitting layer includes a host and a dopant,
The host is an organic electroluminescent device comprising the compound of Formula 1.