KR101956789B1 - New compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a compound of formula (1) and an organic light emitting device comprising the same.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel compound and an organic light-

TECHNICAL FIELD The present invention relates to a novel compound and an organic light emitting device including the same.

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. 10-2013-165394

The present specification aims to provide a compound having excellent brightness and color purity and long lifetime.

The present invention also provides an organic light emitting device comprising the compound.

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

[Chemical Formula 1]

In Formula 1,

X is O; S; Or a C (CH _{3) 2,}

R1 is a substituted or unsubstituted aryl group or a group represented by any one of the following formulas (2) to (4)

R2 to R9 each independently represent any one of the following formulas (2) to (4); heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O, S, Si and Se atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted ring Can,

At least one of R 1 to R 9 is represented by any one of the following formulas (2) to (4)

When at least one of R2 to R9 is represented by any one of the following formulas (2) to (4), R1 is a substituted or unsubstituted aryl group,

(2)

(3)

[Chemical Formula 4]

L1 and L2 are each independently a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

A is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O, S, Si and Se atoms.

In addition, one embodiment of the present disclosure includes 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 one embodiment of the present invention. Can be provided.

The compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device, thereby improving the efficiency of the organic light emitting device, and improving the driving voltage and lifetime.

In addition, the compound according to one embodiment of the present invention can be used as a hole injecting, hole transporting, hole injecting and hole transporting, light emitting, electron transporting, or electron injecting material.

1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment of the present invention.

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

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

Also. When one or more of R1 to R9 in the formula (1) is represented by any one of the following formulas (2) to (4) and at least one of R2 to R9 is represented by any one of the following formulas Lt; / RTI > is a substituted or unsubstituted aryl group.

(2)

(3)

[Chemical Formula 4]

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylamine group; An aralkylamine group; An arylamine group; And an arylphosphine group, or a substituted or unsubstituted one in which at least two of the substituents exemplified above are connected to each other. 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, and may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term " adjacent " means that the substituent is 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 . 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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched and may include a cycloalkyl group. 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 isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

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, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group may be included in the alkyl group and is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 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, examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.

In the present specification, the aryl group may include a fluorenyl group, and is not particularly limited, but may have a carbon number of 6 to 60, 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 phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

, 및

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

,

,

, And

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, S, Si and Se, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazyl group And dibenzofuranyl groups, but are not limited thereto.

In the present specification, the explanation on the aryl group described above can be applied except that the aromatic hydrocarbon ring is a divalent group.

In the present specification, the explanation on the above-mentioned heterocyclic group can be applied except that the heterocycle is divalent.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the alkylaryl group, the aralkylamine group, the aralkenyl group, Can be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the alkylaryl group, the aralkylamine group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group in the heteroaryl group and the heteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, the description of the aryl group described above can be applied except that arylene and alkylarylene are divalent.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

According to one embodiment of the present invention, when at least one of R2 to R9 is represented by any one of the formulas 2 to 4, R1 is a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present invention, when at least one of R 2 to R 9 is represented by any one of formulas 2 to 4, R 1 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, L1 and L2 are each independently a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group.

According to an embodiment of the present invention, each of L 1 and L 2 is independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present invention, each of L 1 and L 2 is independently a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an embodiment of the present invention, each of L 1 and L 2 is independently a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms or a phenylene group.

According to one embodiment of the present invention, the above-mentioned formulas (2) to (4) can provide a compound represented by the following formula (5) or (6)

[Chemical Formula 5]

[Chemical Formula 6]

A and L < 1 > are as defined above.

According to one embodiment of the present invention, the formula (1) may be represented by the following formulas (7) to (12).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the general formulas (7) to (12), R 1 to R 9 are as defined above.

According to one embodiment of the present invention, the formula (1) is represented by the following formulas (13) to (18).

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

X and A are as defined above.

According to one embodiment of the present invention, A is a substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O, S, Si and Se atoms.

According to an embodiment of the present invention, A is a substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O, S, Si and Se atoms.

According to an embodiment of the present invention, A is a substituted or unsubstituted aryl group; Or substituted or unsubstituted triazine.

According to an embodiment of the present invention, when A is an aryl group, A may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present invention, in the case where A is an aryl group, A is a group having 6 to 6 carbon atoms substituted with a heterocyclic group having 3 to 30 carbon atoms and containing at least one of N, O, S, Si and Se atoms To 30 aryl groups.

According to an embodiment of the present invention, when A is an aryl group, A may be an aryl group having 6 to 30 carbon atoms substituted with pyridine, pyrimidine or triazine.

According to one embodiment of the present invention, when A is a heterocyclic group, it may be a substituted or unsubstituted heterocyclic group containing at least one of N, O, S, Si and Se atoms.

According to one embodiment of the present invention, when A is a heterocyclic group, it may be a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.

According to an embodiment of the present invention, when A is a heterocyclic group, it may be a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms including at least one of N, O and S atoms.

According to one embodiment of the present invention, when A is a heterocyclic group, it is a heterocyclic group having 3 to 30 carbon atoms and substituted with an aryl group having 6 to 30 carbon atoms and containing at least one of N, O and S atoms .

According to one embodiment of the present invention, when A is a heterocyclic group, a heterocyclic group having 3 to 30 carbon atoms substituted with a phenyl group, a biphenyl group, or a terphenyl group and containing at least one of N, O and S atoms .

According to an embodiment of the present invention, when A is a heterocyclic group, it may be substituted or unsubstituted pyridine, pyrimidine or triazine.

According to one embodiment of the present disclosure, when A is a heterocyclic group, it may be substituted or unsubstituted triazine.

According to an embodiment of the present invention, when A is a heterocyclic group, it may be triazine substituted with an aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, when A is a heterocyclic group, it may be a phenyl group, a biphenyl group, or a triazine substituted with a terphenyl group.

Also, according to one embodiment of the present disclosure, A may be any one selected from the following formulas.

According to one embodiment of the present invention, R 1 in the above formulas (7) to (9) is represented by any one of formulas (2) to (4)

(2) to (4) are selected from the following Tables 1 to 2.

Table 1

Table 2

According to one embodiment of the present invention, any one of R2 to R9 in the above Chemical Formulas 10 to 12 is represented by any one of Chemical Formulas 2 to 4, and Chemical Formulas 2 to 4 are selected from the above Tables 1 to 2.

FIG. 1 illustrates an organic light emitting device according to an embodiment of the present invention. Referring to FIG. 1, one embodiment of the present disclosure includes a first electrode 101; A second electrode 301 facing the first electrode 101; And at least one organic layer (201) provided between the first electrode (101) and the second electrode (301), wherein at least one of the organic layers (201) And an organic light emitting layer.

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 in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, an electron restraining layer, and an electron transporting supporting 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.

According to one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1). ≪ / RTI >

According to another embodiment of the present invention, the organic layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.

According to one embodiment of the present invention, the organic material layer may include the electron transporting layer or the electron transporting supporting layer.

According to one embodiment of the present disclosure, the organic layer may include an electron inhibiting layer, and the electron inhibiting layer may include the compound of the above formula (1).

According to one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and electron injecting may include the compound of the above formula (1).

According to another embodiment, the organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include the compound of the above formula (1).

According to another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.

 According to another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

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

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

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

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

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

According to one embodiment of the present disclosure, the first electrode may be an anode and the second electrode may be a cathode.

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

The anode material may be a material having a large work function such that holes can be normally injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be 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 porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material 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 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.

The light emitting layer may include a host material and a dopant material. The host material is 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.

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.

Specifically, an iridium complex used as a phosphorescent dopant can be represented as follows. However, the present invention is not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto. And more specifically, Ir (ppy) ₃ , which is a dopant compound having a green color, and the like.

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

In one embodiment of the present invention, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The embodiments described herein are illustrated by way of example. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Scheme 1

1) Synthesis of intermediate A-1

After 50.0 g (1 eq) of 9,9-dimethyl-9H-fluoren-2-amine was dissolved in 500 ml of CHCl 3, 46.8 g (1.1 eq) of NBS was added at 5 ° C at 0 ° C, and the mixture was stirred at room temperature for 1 hour . Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water with water, the organic layer was separated, and the solvent was removed by decompression. This was subjected to column chromatography to obtain 56.1 g (81% yield) of Intermediate A-1. [M + H] = 288

2) Intermediate A- 2 of  Compound synthesis

56.1 g (1.0 eq) of Intermediate A-1 and 33.5 g (1.1 eq) of (2-chlorophenyl) boronic acid (1a) were dissolved in 500 ml of tetrahydrofuran under a nitrogen atmosphere and then a 1.5 M aqueous potassium carbonate solution And 1.99 g (0.02 eq) of bis (tri-tert-butylphosphine) palladium (0) were added thereto, followed by heating and stirring for 1.5 hours. The temperature was lowered to room temperature, and the water layer was separated and removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from hexane, and dried to obtain 46.8 g (yield: 76%) of Intermediate A-2. [M + H] < + > = 320

3) Intermediate A1's  Compound synthesis

46.8 g (1.0 eq) of Intermediate A-2 and 40.4 g (2.0 eq) of K2CO3 were dissolved in 550 ml of dimethylacetamide under nitrogen atmosphere, and 3.3 g (0.1 eq) of Pd (OAc) 2 was added thereto and the mixture was heated and stirred for 17 hours. The temperature is lowered to room temperature and the precipitated solid is filtered and washed with water. The filter cake is dissolved in 1L of chloroform, washed with water, and then the organic layer is separated to remove the solvent. Recrystallization was performed using ethyl acetate to obtain 35.2 g (yield: 85%) of the intermediate A1. [M + H] < + > = 284

Scheme 2

One) Intermediate A- 3 of  Compound synthesis

After dissolving 15.0 g (1.0 eq) of formula A1, 9.1 g (1.1 eq) of bromobenzene (2a) and 6.6 g (1.3 eq) of NaO t- Bu in 150 ml of xylene, a solution of bis (tri- tert -butylphosphine) palladium 0) (0.83 g, 0.03 eq), and the mixture was refluxed and stirred. After 10.5 hours, lower the temperature to room temperature, filter and wash with water to remove the base. 17.3 g (yield 91%) of Intermediate A-3 was obtained using chloroform and ethyl acetate. [M + H] < + > = 360

2) Intermediate A2  synthesis

After dissolving 17.3 g (1 eq) of Intermediate A-3 in 200 ml of DMF, 8.9 g (1.05 eq) of NBS was added in three portions at 0 ° C, followed by stirring at room temperature for 2 hours. Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water with water, the organic layer was separated, and the solvent was removed by decompression. This was recrystallized using chloroform and ethyl acetate to obtain 18.0 g (yield: 85%) of intermediate A2. [M + H] < + > = 438

Scheme 3

1) Synthesis of intermediate B-1

Compound B-1 was prepared in the same manner as Intermediate A-1 except that 9H-carbazol-2-ol was used instead of 9,9-dimethyl-9H-fluoren-2-amine.

2) Synthesis of intermediate B-2

Compound B-2 was prepared in the same manner as Intermediate A-2 except that Intermediate B-1 and (4-chloro-2-fluorophenyl) boronic acid were used instead of Intermediate A-1 and Intermediate 1a.

3) Intermediate B- 3 of  synthesis

30.9 g (1.0 eq) of Intermediate B-2 and 27.4 g (2.0 eq) of calcium carbonate were dissolved in 170 ml of N-methyl-2-pyrrolidone in a 500 ml round bottom flask and the mixture was heated with stirring for 2 hours. The temperature is lowered to room temperature and the solution is reprecipitated in water. The residue was completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain 23.9 g (yield: 83%) of Intermediate B-3. [M + H] < / RTI > = 292

4) Intermediate B1  synthesis

Compound B1 was prepared in the same manner as Intermediate A-3 except that Intermediate B-3 was used instead of Intermediate A-1.

Scheme 4

1) Synthesis of intermediate B-4

4 was prepared in the same manner as Intermediate A-2 except for using Intermediate B-1 and (2-fluorophenyl) boronic acid (3b) instead of Intermediate A-1 and Intermediate 1a.

2) Intermediate B2  synthesis

Compound B2 was prepared in the same manner as Intermediate B-3 except that Intermediate B-4 was used instead of Intermediate B-2.

Scheme 5

1) Synthesis of intermediate C-1

 After dissolving 30.0 g (1.0 eq) of propan-2-one in 300 ml of tetrahydrofuran under nitrogen atmosphere, 3.0 g of (4-chlorophenyl) magnesium bromide (3.0 eq) was slowly added dropwise at 0 and stirred for about 1 hour at room temperature. . After quenched with NH4Cl aqueous solution, the organic layer was separated by dissolving in ethyl acetate, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. This was purified by column chromatography to obtain 69.1 g (yield 78%) of Intermediate C-1. [M + H] < + > = 171

2) Intermediate C- 2 of  synthesis

Dissolve 69.1 g (1.7 eq) of Intermediate C-1 in 650 ml of acetonitrile, dissolve 92.2 g (1.5 eq) of calcium carbonate in 400 ml of water, add 80.0 ml (1.1 eq) of nonafluorobutanesulfonyl fluoride slowly at 0 . Thereafter, the mixture was stirred at room temperature for 3.5 hours. After the reaction was completed, the solution was completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain 135.2 g (yield: 74%) of Intermediate C-2. [M + H] < + > = 452

2) Intermediate C1  synthesis

40.0 g (1.1 eq) of Pd (dppf) Cl _2, 1.0 g (0.1 mol%) of 4,4,5,5-tetramethyl- [1,3,2] ) And 42.1 g (3.0 eq) of KOAc were placed in 600 mL of dioxane and stirred at reflux for 12 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl3, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 36.1 g (90% yield) of intermediate C1 was obtained. MS: [M + H] < ⁺ > = 281

Scheme 6

Compound C2 was prepared in the same manner as Intermediate C1 except for using (3-chlorophenyl) magnesium bromide (3c) instead of Intermediate 1c.

Scheme 7

2.47 g (0.02 eq) of Pd (PPh3) 4 and 0.02 eq. Of K2CO3 dissolved in water were added to 20.0 g (1.0 eq) of intermediate C1 and 28.6 g (1.0 eq) of 2-chloro-4,6- g (2.0 eq) was added to 250 ml of THF, and the mixture was refluxed and stirred. After 2 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl 3 and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure, and recrystallized from chloroform and ethanol to obtain 35.2 g (yield: 85%) of intermediate C3 as a white solid. [M + H] < + > = 386

Scheme 8

Compound C4 was prepared in the same manner as Intermediate C3 except that Intermediate C2 was used instead of Intermediate C1.

Scheme 9

4-yl) -6-chloro-1,3,5-triazin-2-yl) benzene-1-ylium (4c) was used instead of Intermediate 4c The above compound C5 was prepared in the same manner as in the preparation of intermediate C3.

Scheme 10

Intermediate C3 was obtained except that Intermediate C2 and 2,4-di ([1,1'-biphenyl] -4-yl) -6-chloro-1,3,5-triazine (6c) The compound C6 was prepared in the same manner as the preparation method.

Scheme 11

The same procedure as for the preparation of intermediate C3 was repeated except that 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (7c) The above compound C7 was prepared.

Scheme 12

1) Synthesis of intermediate D-1

Compound D-1 was prepared in the same manner as Intermediate C3 except that Intermediate A2 was used instead of Intermediate 4c.

2) Intermediate D1's  synthesis

18.1 g (1.2 eq) of Bis (pinacolato) diboron, 1.0 g (0.03 eq) of Pd (dba) 2, 0.99 g (0.06 eq) of PCy3 and 17.5 g (3.0 eq) of KOAc were added to 30.4 g (1.0 eq) Was put into 310 mL of dioxane, refluxed, and stirred for 7 hours. After completion of the reaction was confirmed by TLC, the base was removed by filtration, and the solution was concentrated under reduced pressure. This was dissolved in CHCl 3 and completely washed with water. The solution in which the product was dissolved was concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain 31.5 g (yield: 88%) of Intermediate D1. [M + H] = 604

Scheme 13

Compound D2 was prepared in the same manner as in Scheme 12, except that Intermediate C2 was used instead of Intermediate C1.

Scheme 14

Compound D3 was prepared in the same manner as in Scheme 12, except that Intermediate B1 was used instead of Intermediate A2.

Scheme 15

Compound D4 was prepared in the same manner as in Scheme 13, except that Intermediate B1 was used instead of Intermediate A2.

Subsequently, the compounds of the present invention were further synthesized by using Buchwald-Hartwig coupling reaction or Suzuki coupling reaction with intermediates A1, A2, B1 B2, C1 to C7 and D1 to D4.

Synthetic example  1. Compound 1

Formula A1 7.0 g (1.0 eq) and intermediate C3 10.0 g (1.05 eq), and NaO t -Bu 3.1 g (1.3 eq ) a, Bis (tri- tert -butylphosphine) was dissolved in xylene and 80 ml palladium (0) 0.38 g (0.03 eq) was added thereto, and the mixture was refluxed and stirred. After 11 hours, the temperature is lowered to room temperature, filtered, and washed with water to remove the base. 11.3 g (yield 72%) of the compound 1 was obtained using tetrahydrofuran and ethyl acetate. [M + H] < + > = 633

Synthetic example  2. Compound 2

9.2 g (yield 69%) of the compound was prepared in the same manner as the compound 1 except that Intermediate C4 was used instead of Intermediate C3. [M + H] < + > = 633

Synthetic example  3. Compound 3

10.1 g (71% yield) of the compound was prepared in the same manner as the compound 3 except that Intermediate C7 was used instead of Intermediate C3. [M + H] < + > = 723

Synthetic example  4. Compound 4

9.0 g (Yield 65%) of Compound 4 was prepared in the same manner as in the preparation of Compound 4, except that Intermediate B2 and Intermediate C4 were used instead of Intermediates A1 and Intermediate C3. [M + H] < + > = 607

Synthetic example  5. Compound 5

9.0 g (Yield 65%) of Compound 5 was prepared in the same manner as in the preparation of Compound 5, except that Intermediate B2 and Intermediate C5 were used instead of Intermediates A1 and Intermediate C3. [M + H] < + > = 683

Synthetic example  6. Compound 6

9.7 g (Yield 69%) of Compound 6 was prepared in the same manner as in the preparation of Compound 6, except that Intermediate B2 and Intermediate C6 were used instead of Intermediate Al and Intermediate C3. [M + H] = 759

Synthetic example  7. Compound 7

Intermediate D1 8.0 g (1.0 eq) Intermediate 4c 3.5 g (1.0 eq), Pd (PPh 3) ₄ in 0.31 g (0.02 eq) of K ₂ CO ₃ dissolved in water (3.7 g, 2.0 eq) was added to 100 mL of THF, and the mixture was refluxed and stirred. After 5 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and recrystallized using THF and ethyl acetate to obtain 8.1 g (yield 86%) of Compound 7. [M + H] = 709

Synthetic example  8. Compound 8

10.3 g (84% yield) of Compound 8 was prepared in the same manner as Compound 7, except that Intermediate D4 was used instead of Intermediate D1. [M + H] < + > = 683

Synthetic example  9. Compound 9

8.0 g (yield 75%) of Compound 9 was prepared in the same manner as in the preparation of Compound 7, except that Intermediate D2 and Intermediate 6c were used instead of Intermediate D1 and Intermediate 4c. [M + H] = 861

Synthetic example  10. Compound 10

Except that Intermediate D3 and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine were used in place of Intermediate D1 and Intermediate 4c. 11.3 g (84% yield) of Compound 10 was prepared in the same manner as in the method of Example 1, [M + H] = 773

Synthetic example  11. Compound 11

1) Synthesis of intermediate E-1

Compound E-1 was prepared in the same manner as Intermediate D1, except that Intermediate A2 was used instead of Intermediate D-1.

1) Preparation of compound of formula 11

7.6 g (1.1 eq) of intermediate C5, 0.23 g (0.03 eq) of Pd (t-Bu3P) 2 and 8.0 g (2.5 eq) of K3PO4 dissolved in water were added to 90 mL of Dioxnae to 7.3 g And the mixture was refluxed and stirred. After 10 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This is dissolved in CHCl3 and rinsed thoroughly with water to remove the base. Tetrahydrofuran and ethyl acetate were recrystallized using a mixed solution to obtain 9.2 g (yield 78%) of Compound 11. [M + H] = 785

Synthetic example  12. Compound 12

9.1 g (Yield 79%) of Compound 12 was prepared in the same manner as Compound 11, except that Intermediate B1 and Intermediate C4 were used instead of Intermediate A2 and Intermediate C5. [M + H] < + > = 683

<Experimental Example 1>

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer.

The HT-1 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposition layer to a thickness of 50 Å to form an electron blocking layer.

Compound 1 and a phosphorescent dopant Dp-25 were co-deposited on the HT-2 deposited film at a weight ratio of 12% to form a light emitting layer having a thickness of 400 Å. At this time, The light emitting layer comprises at least one host material and a dopant, and may be a mixture of two or more kinds of host materials.

An ET-1 material was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM and an ET-2 material was co-deposited with a 2% weight ratio Li to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

<Experimental Example 2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 3>

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

<Experimental Example 4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 6>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 10 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 11 was used instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound H-1 was used instead of Compound 1 in Experimental Example 1

<Experimental Example 9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 2 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 4 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Experimental Example 11 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 5 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 12>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 8 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 13>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 9 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 11 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

<Experimental Example 15>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 12 and H-1 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound H-1 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

The results of the above experiment are shown in Table 3 below.

compound Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color T95
(@ 20 mA / cm ² ) Experimental Example 1 One 2.74 65.5 green 59 Experimental Example 2 3 2.79 71.0 green 63. Experimental Example 3 4 2.75 69.5 green 61 Experimental Example 4 6 2.80 67.3 green 59 Experimental Example 5 7 2.78 65.4 green 57 Experimental Example 6 8 2.73 69.1 green 56 Experimental Example 7 10 2.76 63.9 green 59 Experimental Example 8 11 2.81 67.8 green 62 Experimental Example 9 2, H-2 3.22 74.9 green 169 Experimental Example 10 4, H-2 3.23 75.0 green 163 Experimental Example 11 5, H-2 3.25 73.1 green 174 Experimental Example 12 8, H-2 3.30 75.0 green 160 Experimental Example 13 9, H-2 3.24 75.1 green 164 Experimental Example 14 11, H-2 3.29 74.7 green 170 Experimental Example 15 12, H-1 3.30 76.1 green 159 Comparative Example 1 H-1 3.01 60 green 40 Comparative Example 2 H-1, H-2 3.52 67 green 140

The results of Table 3 show that the compound of the present invention has the advantage of low voltage and high efficiency and has a lifetime of about 40 to 60% more than compound H-1 which is a conventional green luminescent host material. In addition, the use of a two-component host shows better performance in terms of efficiency and lifetime.

While the present invention has been described in connection with the preferred embodiments thereof with reference to the accompanying drawings, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, .

101: first electrode
201: organic layer
301: second electrode

Claims (16)

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

In Formula 1,
X is O; S; Or a C (CH _{3) 2,}
R1 is an aryl group or a group represented by the following formula (5) or (6)
R2 to R5 are each independently represented by the following formula (5) or (6): hydrogen; Or deuterium,
R6 to R9 are each independently hydrogen; Or deuterium,
At least one of R 1 to R 5 is represented by the following general formula (5) or (6)
When at least one of R2 to R5 is represented by the following formula 5 or 6, R1 is an aryl group,
[Chemical Formula 5]

[Chemical Formula 6]

L1 is an alkylene group,
A is a heterocyclic group containing at least one N, which is substituted or unsubstituted with at least one selected from the group consisting of an aryl group and a heterocyclic group. delete The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (7) to (12):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the above formulas (7) to (12)
Gt; to R &lt; 9 &gt; are as defined in claim 1. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (13), (14) and (16)
[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 16]

In the above formulas (13), (14) and (16)
X and A are as defined in claim 1. delete The method according to claim 1,
Wherein A is triazine substituted or unsubstituted with at least one member selected from the group consisting of an aryl group and a heterocyclic group. The method according to claim 1,
Wherein A is any one selected from the following structural formulas:

. The method of claim 3,
R1 in the above formulas (7) to (9) is represented by the above formula (5) or (6)
(5) or (6) are selected from the following Tables 1 to 2:
Table 1

Table 2

. The method of claim 3,
Any one of R2 to R5 of the above formulas (10) to (12) is represented by the above formula (5) or (6)
(5) or (6) are selected from the following Tables 1 to 2:
Table 1

Table 2

. 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 layers comprises a compound according to any one of claims 1, 3, 4 and 6 to 9. 11. The organic light emitting device according to claim 10, wherein the organic material layer includes a hole transporting layer, and the hole transporting layer comprises the compound. 11. The organic light emitting device according to claim 10, wherein the organic layer includes a hole injection layer, and the hole injection layer comprises the compound. 11. The organic light emitting device according to claim 10, wherein the organic layer includes an electron suppressing layer, and the electron suppressing layer comprises the compound. [Claim 11] The organic light emitting device according to claim 10, wherein the organic layer includes a layer that simultaneously injects holes and transports holes, and the layer that simultaneously injects holes and transports the compound. 11. The organic light emitting device according to claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer. 11. The organic light emitting device according to claim 10, wherein the organic compound layer contains the compound as a host and contains another organic compound, metal or metal compound as a dopant.

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