KR101977935B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

TECHNICAL FIELD [0001] The present invention relates to novel compounds and organic light emitting devices using the same,

The present invention relates to a novel compound and an organic light emitting device comprising 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. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multilayer structure composed of different materials. For example, the organic material layer 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.

There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

X < ₁ > is O or S,

; 또는 적어도 하나의

로 치환된, C_6-60 아릴, 또는 N, O 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 내지 3개 포함하는 C_2-60 헤테로아릴이고,A is

; Or at least one

And a, C _6-60 aryl, or C _2-60 heteroaryl group containing one to three heteroatoms selected from the group consisting of N, O, and S substituted with,

Y ₁ to Y ₃ are each independently N or CR ₃ , at least one of Y ₁ to Y ₃ is N,

L ₁ is a bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,

a1 and a2 are each independently an integer of 0 to 3,

n and m are each independently 1 or 2;

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 .

The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

는 다른 치환기에 연결되는 결합을 의미하고, 단일 결합은 L1으로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In the present specification,

Refers to a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L < 1 >.

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; 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; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents 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, or may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an 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, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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 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- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

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

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl 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 pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, an isoxazolyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. 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 description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.

The present invention also provides a compound represented by the above formula (1).

; 또는 1개 또는 2개의

로 치환된, C_6-20 아릴일 수 있다.In the above formula (1), A represents

; Or one or two

, &_{Lt; /} RTI >

For example, A may be any one selected from the group consisting of:

In the above,

n is independently 1 or 2;

Specifically, for example, A may be any one selected from the group consisting of:

Y ₁ and Y ₂ are N, Y ₃ is CR ₃ ,

Y ₁ and Y ₃ are N, Y ₂ is CR ₃ , or

Y ₁ , Y _2, and Y ₃ may be N.

For example, Y ₁ , Y _2, and Y ₃ may be N.

In addition, L < ₁ > may be bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

For example, L < ₁ > may be a bond, or any one selected from the group consisting of:

.

.

Specifically, for example, L < ₁ > may be a bond, or any one selected from the group consisting of:

.

.

Ar ₁ and Ar ₂ each independently may be any one selected from the group consisting of:

In the above,

Z ₁ to Z ₄ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,

c1 to c3 each independently represent an integer of 0 to 3;

Wherein Z ₁ to Z ₄ are each independently hydrogen, methyl or phenyl, and c 1 to c 3 each independently may be 0 or 1.

For example, Ar ₁ and Ar ₂ may each independently be selected from the group consisting of:

Each of R ₁ to R ₃ independently represents hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl.

For example, R ₁ to R ₃ may be hydrogen.

Here, a1 represents the number of R ₁ , and when a ₁ is 2 or more, two or more R _{1 s} may be the same or different from each other. a2 and c1 to c3 can be understood with reference to the description of a1 and the structure of the above formula.

Further, the compound may be represented by the following general formula (1-1) or (1-2):

[Formula 1-1]

[Formula 1-2]

In the above formulas 1-1 and 1-2,

X ₁ , Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ and A are the same as defined in the above formula (1).

In addition, the compound may be any one selected from the group consisting of the following compounds:

The compound represented by the formula (1) can be prepared, for example, according to the following reaction scheme 1 or 2.

[Reaction Scheme 1]

[Reaction Scheme 2]

In the above Reaction Schemes 1 and 2, the definitions other than X are as defined above, and X is halogen, more preferably chloro or bromo.

The reaction is preferably carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The above production method can be more specific in the production example to be described later.

The compound represented by Formula 1 has a structure in which a 6-membered heterocyclic group containing at least one N atom and a substituent group A as described above are linked to a specific position of dibenzofuran or dibenzothiophene core, The organic light emitting device used can have high efficiency, low driving voltage, high brightness and long life.

Meanwhile, the present invention provides an organic light emitting device comprising the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 .

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting 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.

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes. The hole injecting layer, the hole transporting layer, And the like.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

The electron transport layer, the electron injection layer, or the layer which simultaneously transports electrons and electrons may include a layer that simultaneously performs the electron transport layer, the electron injection layer, or the electron transport and electron injection. ≪ / RTI >

The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1).

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, in the organic light emitting device of the present invention, in addition to the light emitting layer as the organic material layer, a hole injecting layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the second electrode are further included . ≪ / RTI > However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.

The organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which an anode, one or more organic compound layers and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1. [ In addition, 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.

For example, the organic light emitting device according to 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, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the organic material layer, and then depositing a material usable as a cathode on the organic material layer. 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.

The compound represented by Formula 1 may be formed into an organic 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 can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the positive electrode material 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 layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting 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 as described above. The host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound in addition to the compound represented by the formula (1). 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.

The electron transporting layer 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. 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 nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, 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.

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

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[ Manufacturing example ]

Manufacturing example  1: Preparation of Compound A-1

Chloro-2-methoxyphenylboronic acid (62.2 g, 333.5 mmol) was dissolved in tetrahydrofuran (800 mL). Here sodium 2 M solution (500 mL), tetrakis (triphenylphosphine) palladium _{(0) [Pd (PPh 3} ) 4] (7.7 g, 6.7 mmol) insert was refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated and dried with magnesium sulfate. The filtrate was distilled under reduced pressure. The resulting mixture was recrystallized three times using chloroform and ethanol to obtain Compound A-1 (53.7 g, yield 51%; MS: [M + ⁺ = 314).

Manufacturing example  2: Preparation of Compound A-2

Compound A-1 (50.0 g, 158.5 mmol) was dissolved in dichloromethane (600 mL) and then cooled to 0 占 폚. Boron tribromide (15.8 mL, 166.4 mmol) was slowly added dropwise and stirred for 12 hours. After the reaction was completed, the reaction mixture was washed with water three times, dried over magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain Compound A-2 (47.4 g, yield 99%; MS: [M ⁺ = 300).

Manufacturing example  3: Preparation of Compound A-3

Compound A-2 (40.0 g, 132.7 mmol) was dissolved in distilled dimethylformamide (400 mL). This was cooled to 0 < 0 > C and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. The mixture was stirred for 20 minutes and then at 100 ° C for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature, and ethanol (100 mL) was slowly added thereto. The mixture was vacuum distilled, and the resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound A-3 (30.3 g, yield 81%; MS: [M + H] ⁺ = 280).

Manufacturing example  4: Preparation of Compound A-4

Compound A-3 (30.0 g, 106.6 mmol) was dissolved in tetrahydrofuran (300 mL), the temperature was lowered to -78 ° C and 1.7 M tert-butyllithium (62.7 mL, 106.6 mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropylborate (28.3 mL, 213.1 mmol) was added, and the mixture was stirred at room temperature for 3 hours while gradually warming to room temperature. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (200 mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and vacuum dried. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered and dried to obtain Compound A-4 (24.4 g, yield 93%; MS: [M + H] ⁺ = 247).

Manufacturing example  5: Preparation of Compound A-5

After dispersing Compound A-4 (20.0 g, 81.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (21.8 g, 81.2 mmol) in tetrahydrofuran , it was added a 2M aqueous potassium carbonate solution (33.6 mL, 243.5 mmol) and tetrakistriphenylphosphine palladium was pinot _{[Pd (PPh 3) 4]} (1.9 g, 2 mol%) was stirred for 4 hours and then put under reflux. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to give Compound A-5 (32.4 g, yield 92%; MS: [M + H] ⁺ = 434).

Manufacturing example  6: Preparation of Compound A-6

Compound A-5 (30 g, 69.2 mmol) Bis (pinacolato) diboron (19.3 g, 76.1 mmol), potassium acetate (20.4 g, 207.5 mmol), tetrakistriphenylphosphinopalladium (0) [Pd PPh ₃ ) ₄ ] (1.6 g, 2 mol%) were placed in tetrahydrofuran (300 mL) and refluxed for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated and dried over magnesium sulfate. Compound A-6 (34.5 g, yield 95%; MS: [M + H] ⁺ = 526) was prepared by distillation under reduced pressure.

Manufacturing example  7: Preparation of compound B-1

Except that 2-methoxyphenyl) boronic acid (50.7 g, 333.5 mmol) was used in place of 5-chloro-2-methoxyphenylboronic acid (62.2 g, 333.5 mmol) B-1 (81.6 g, yield 87%; MS: [M + H] < ⁺ > = 280).

Manufacturing example  8: Preparation of compound B-2

Compound B-2 (71.2 g, yield 99%; MS (yield: 99%) was obtained in the same manner as in the preparation of Compound A-2 except that Compound B-1 (75.7 g, 269.4 mmol) : [M + H] < ⁺ > = 266).

Manufacturing example  9: Preparation of compound B-3

Compound B-3 (62.3 g, yield 95%; MS (yield: 95%) was obtained in the same manner as Compound A-2 except that Compound B-2 (70.9 g, 265.3 mmol) : [M + H] < ⁺ > = 246).

Manufacturing example  10: Preparation of compound B-4

Compound B-3 (40 g, 161.9 mmol) was dissolved in acetic acid (200 mL). Iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol) and sulfuric acid (10 mL) were added thereto, followed by stirring at 65 ° C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and water was added thereto. The resulting solid was filtered, washed with water, and then recrystallized from toluene and ethyl acetate to obtain Compound B-4 (50.1 g, yield 83%; MS: [M + H] ⁺ = 372).

Manufacturing example  11: Preparation of compound B-5

(18.0 g, 80.7 mmol) was added to a solution of the compound B-4 (30 g, 80.7 mmol) and (2'-thiano- [1,1'- biphenyl] -4- yl) boronic acid ). Here sodium 2 M solution (121 mL), put the tetrakis (triphenylphosphine) palladium _{(0) [Pd (PPh 3} ) 4] (1.9 g, 2 mol%) was refluxed for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated and dried over magnesium sulfate, and the filtrate was distilled under reduced pressure. The resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound B-5 (25 g, yield 74%; MS: [M + H ] ⁺ = 424).

Manufacturing example  12: Preparation of compound B-6

(25 g, 59.1 mmol) and bis (pinacolato) diboron (22.1 g, 76.8 mmol), potassium acetate (18.4 g, 187.4 mmol), tetrakistriphenylphosphinopalladium (0) [Pd _{(PPh 3) 4] (1.4} g, 2 mol%) is put into a tetrahydrofuran (300 mL) was refluxed for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated and dried over magnesium sulfate. This was subjected to vacuum distillation to obtain Compound B-6 (25.0 g, yield 90%; MS: [M + H] ⁺ = 472).

Manufacturing example  13: Preparation of Compound C-1

Except that 4-chloro-2-methoxyphenylboronic acid (62.2 g, 333.5 mmol) was used instead of 5-chloro-2-methoxyphenylboronic acid (62.2 g, 333.5 mmol) (65.3 g, yield 62%; MS: [M + H] < ⁺ > = 315).

Manufacturing example  14: Preparation of compound C-2

Compound C-2 (43.0 g, yield 90%; MS (yield: 90%) was obtained in the same manner as Compound A-2 except that Compound C-1 (50.0 g, 158.5 mmol) : [M + H] < ⁺ > = 300).

Manufacturing example  15: Preparation of Compound C-3

Compound C-3 (30.6 g, yield 82%; MS (M + H)) was obtained in the same manner as Compound A-3 except that Compound C-2 (40.0 g, 132.7 mmol) : [M + H] < ⁺ > = 280).

Manufacturing example  16: Preparation of compound C-4

Compound C-4 (25.0 g, yield 95%; MS (yield: 95%) was obtained in the same manner as Compound A-3 except that Compound C-3 (30.0 g, 106.6 mmol) : [M + H] < ⁺ > = 247).

Manufacturing example  17: Preparation of compound C-5

Compound C-5 (31.7 g, yield 90%; MS (yield: 90%) was obtained in the same manner as Compound A-5 except that Compound C-4 (20.0 g, 81.2 mmol) : [M + H] < ⁺ > = 434).

Manufacturing example  18: Preparation of compound D-2

Compound D-2 (39.7 g, yield 83%; MS (M + H) +) was obtained in the same manner as in the preparation of Compound A-2 except that Compound D-1 (50.0 g, 158.5 mmol) : [M + H] < ⁺ > = 300).

Manufacturing example  19: Preparation of compound D-3

Compound D-3 (31.4 g, yield 84%; MS (M + H) +) was obtained in the same manner as in the preparation of Compound A-3 except that Compound D-2 (40.0 g, 132.7 mmol) : [M + H] < ⁺ > = 280).

Manufacturing example  20: Preparation of compound D-4

Compound D-4 (25.5 g, yield 97%; MS (M + H) +) was obtained in the same manner as in the preparation of Compound A-4 except that Compound D-3 (30.0 g, 106.6 mmol) : [M + H] < ⁺ > = 247).

Manufacturing example  21: Preparation of compound D-5

Compound D-5 (32.4 g, yield 92%; MS (yield: 92%) was obtained in the same manner as Compound A-5 except that Compound D-4 (20.0 g, 81.2 mmol) : [M + H] < ⁺ > = 434).

[ Example ]

Example  1: Preparation of compound 1

Compound A-6 (20 g, 38.1 mmol) and 4-bromobenzonitrile (7.6 g, 41.9 mmol) of tetrahydrofuran which, 2M potassium carbonate aqueous solution and then dispersed in (200 mL) (aq. K 2 CO 3 ) (57.2 mL, 114.3 mmol) was added and tetrakistriphenylphosphine palladium pinot [Pd (PPh _{3) 4]} was placed a (1.3 g, 3 mol%) was stirred and refluxed for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to give Compound 1 (12.4 g, yield 65%; MS: [M + H] ⁺ = 501).

Example  2: Preparation of compound 2

Except that 4'-bromo- [1,1'-biphenyl] -4-carbonitrile (10.8 g, 41.9 mmol) was used in place of 4-bromobenzonitrile. 15.4 g, yield 70%; MS: [M + H] < ⁺ > = 577).

Example  3: Preparation of compound 3

Except that 4'-bromo- [1,1'-biphenyl] -3-carbonitrile (10.8 g, 41.9 mmol) was used in place of 4-bromobenzonitrile. 13.4 g, yield: 61%; MS: [M + H] < ⁺ > = 577).

Example  4: Preparation of compound 4

Except that 4'-bromo- [1,1'-biphenyl] -2-carbonitrile (10.8 g, 41.9 mmol) was used in place of 4-bromobenzonitrile. 16.0 g, yield 73%; MS: [M + H] < ⁺ > = 577).

Example  5: Preparation of compound 5

Except that 3'-bromo- [1,1'-biphenyl] -4-carbonitrile (10.8 g, 41.9 mmol) was used in place of 4-bromobenzonitrile. 12.5 g, yield 57%; MS: [M + H] < ⁺ > = 577).

Example  6: Preparation of Compound 6

Except that 2'-bromo- [1,1'-biphenyl] -4-carbonitrile (10.8 g, 41.9 mmol) was used in place of 4-bromobenzonitrile. 8.3 g, yield 38%; MS: [M + H] < ⁺ > = 577).

Example  7: Preparation of Compound 7

Except that 4'-bromo- [1,1'-biphenyl] -3,5-dicarbonitrile (11.8 g, 41.9 mmol) was used instead of 4-bromobenzonitrile Compound 7 (17.9 g, yield 78%; MS: [M + H] ⁺ = 602) was prepared.

Example  8: Preparation of compound 8

(11.8 g, 41.9 mmol) was used instead of 4-bromobenzonitrile in place of 4-bromobenzonitrile (15.6 g, yield 68%; MS: [M + H] < ⁺ > = 602) was prepared in the same manner as in the preparation of Compound 1.

Example  9: Preparation of compound 9

Compound B-6 (20.0 g, 42.4 mmol) and 2 - ([1,1'-biphenyl] -4-chloro- 42.4 mmol) of was dispersed in tetrahydrofuran (300 mL), 2M potassium carbonate aqueous solution _{(aq. K 2 CO 3)} (64 mL, was added 127 mmol) and tetrakis triphenyl phosphino palladium [Pd (PPh ₃ ) ₄ ] (1.5 g, 2 mol%) was added thereto, followed by stirring and refluxing for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from chloroform and ethyl acetate, filtered and dried to obtain Compound 9 (19.4 g, yield 70%; MS: [M + H] ⁺ = 653).

Example  10: Preparation of compound 10

Chloro-4- (dibenzo [b, d] pyridin-2-yl) (19.5 g, yield 69%; MS: < 1 > H) in the same manner as in the preparation of Compound 9, [M + H] < ⁺ > = 642).

Example  11: Preparation of compound 11

Chloro-2- (dibenzo [b, d] pyridin-2-yl) (15.5 g, yield 55%; MS: < RTI ID = 0.0 > mmol) < / RTI & [M + H] < ⁺ > = 642).

Example  12: Preparation of compound 12

The compound C-5 (20.0 g, 46.2 mmol) and (2'-cyano- [1,1'- biphenyl] -4- yl) boronic acid (9.2 g, 46.2 mmol) were dissolved in dioxane (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 mmol) were added to a solution of bis (dibenzylidineacetone) palladium (aq. K ₃ PO ₄ ) mg, 2.8 mmol) were added thereto, followed by stirring and refluxing for 12 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from chloroform and ethyl acetate, filtered and dried to give Compound 12 (18.1 g, yield 68%; MS: [M + H] ⁺ = 577).

Example  13: Preparation of compound 13

(16.0 g, yield 60%; MS: [M + H] < ⁺ > = 577) in the same manner as in the preparation of Compound 11, except that Compound D-5 (20.0 g, 46.2 mmol) .

Example  14: Preparation of compound 14

Instead of 2- (4-bromophenyl) -4,6-dihydro-2-phenyl-1,3,5- Compound 14 (19.4 g, yield 70%; MS: [M + H] ⁺ = 653 (M + H) ⁺ ) was prepared in the same manner as in the preparation of Compound 6, except that diphenyl-1,3,5- ).

Example  15: Preparation of compound 15

Instead of 2- (4-bromophenyl) -4,6-dihydro-2-phenyl-1,3,5- Compound 16 (16.6 g, yield 60%; MS: [M + H] ⁺ = 653 (M + H) ⁺ ) was prepared in the same manner as in the preparation of Compound 6, except that diphenyl- ).

[ Experimental Example ]

Experimental Example  1-1

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 following HT-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer, and HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 Å to form an electron blocking layer. Compound 1 prepared in Example 1, the following YGH1 compound, and phosphorescent dopant YGD-1 were co-deposited as a light emitting layer on the HT-2 deposited film at a weight ratio of 44:44:12 to form a 400Å thick light emitting layer. The following ET-1 compound was vacuum-deposited on the light-emitting layer to a thickness of 250 ANGSTROM, and the following ET-2 compound was co-deposited with Li at a weight ratio of 2% 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  1-2 to 1-15

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

compare Experimental Example  1-1 and 1-2

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the compound described in the following Table 1 was used instead of the Compound 1 of Example 1 in Experimental Example 1. The compounds of CE1 and CE2 in the following Table 1 are as follows.

The experimental examples and comparative experimental examples were measured drive voltage and luminous efficiency of the organic light emitting devices at a current density of 10 mA / cm ² at, 50 mA / cm ² the time of 95% compared to the initial luminance at a current density (LT ₉₅ ) Were measured. The results are shown in Table 1 below.

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Life span (h)
LT ₉₅ at 50mA / cm ² Experimental Example 1-1 Compound 1 4.1 73 0.46, 0.54 110 Experimental Example 1-2 Compound 2 3.9 75 0.46, 0.54 130 Experimental Example 1-3 Compound 3 3.8 80 0.46, 0.53 150 Experimental Examples 1-4 Compound 4 3.7 74 0.46, 0.53 320 Experimental Examples 1-5 Compound 5 3.9 60 0.46, 0.52 200 Experimental Example 1-6 Compound 6 3.9 74 0.46, 0.54 290 Experimental Example 1-7 Compound 7 4.0 70 0.46, 0.53 300 Experimental Examples 1-8 Compound 8 4.0 72 0.46, 0.52 310 Experimental Examples 1-9 Compound 9 3.8 72 0.46, 0.53 330 Experimental Example 1-10 Compound 10 3.7 73 0.46, 0.54 342 Experimental Example 1-11 Compound 11 3.7 66 0.46, 0.53 351 Experimental Example 1-12 Compound 12 3.9 78 0.46, 0.54 220 Experimental Example 1-13 Compound 13 3.9 74 0.46, 0.54 180 Experimental Example 1-14 Compound 14 3.8 77 0.46, 0.53 150 Experimental Example 1-15 Compound 15 3.7 80 0.46, 0.53 175 Comparative Experimental Example 1-1 CE1 4.0 70 0.46, 0.53 90 Comparative Experimental Example 1-2 CE2 4.5 60 0.44, 0.55 15

As shown in Table 1, when the compound of the present invention was used as a light emitting layer material, it was confirmed that the compound exhibited better efficiency and longer lifetime than the comparative example.

Experimental Example  2-1

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

The following HI-1 compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. The following HT-1 compound was vacuum-deposited on the hole injection layer to a thickness of 400 Å to form a hole transport layer, and a host H1 and a dopant D1 compound were vacuum-deposited to a thickness of 300 Å at a weight ratio of 97.5: 2.5. The following compound ET-A was vacuum deposited on the light emitting layer to a thickness of 50 Å to form an electron transporting layer. Compound 1 prepared in Example 1 and LiQ (Lithium Quinolate) were vacuum deposited on the electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- 7} to 5 x 10 < ^-6 > torr to manufacture an organic light emitting device.

Experimental Example  2-2 to 2-15

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound described in the following Table 2 was used instead of the compound 1 of Example 1 in Experimental Example 2-1.

compare Experimental Example  2-1 and 2-2

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound described in the following Table 2 was used instead of the compound 1 of Example 1 in Experimental Example 2-1. The compounds of CE3 and CE4 in the following Table 2 are as follows.

The experimental examples and comparative experimental examples were measured drive voltage and luminous efficiency of the organic light emitting devices at a current density of 10 mA / cm ² at, 50 mA / cm ² the time of 95% compared to the initial luminance at a current density (LT ₉₅ ) Were measured. The results are shown in Table 2 below.

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (Cd / A)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Life span (h)
LT ₉₅ at 50mA / cm ² Experimental Example 2-1 Compound 1 4.1 6.9 0.134, 0.133 90 EXPERIMENTAL EXAMPLE 2-2 Compound 2 4.1 6.0 0.133, 0.133 180 Experimental Example 2-3 Compound 3 3.9 6.2 0.134, 0.132 220 Experimental Example 2-4 Compound 4 3.6 7.1 0.134, 0.132 265 Experimental Example 2-5 Compound 5 3.6 7.2 0.134, 0.132 170 Experimental Examples 2-6 Compound 6 3.7 6.9 0.134, 0.133 170 Experimental Example 2-7 Compound 7 3.7 6.8 0.133, 0.133 160 Experimental Examples 2-8 Compound 8 3.8 7.1 0.134, 0.132 140 Experimental Examples 2-9 Compound 9 3.8 6.7 0.134, 0.132 277 Experimental Example 2-10 Compound 10 3.7 7.2 0.134, 0.132 290 Experimental Example 2-11 Compound 11 3.7 7.0 0.134, 0.133 220 Experimental Examples 2-12 Compound 12 3.7 7.0 0.132, 0.134 115 Experimental Example 2-13 Compound 13 3.6 6.8 0.133, 0.135 160 Experimental Example 2-14 Compound 14 3.6 7.7 0.134, 0.133 175 Experimental Example 2-15 Compound 15 3.7 7.9 0.134, 0.133 90 Comparative Experimental Example 2-1 CE3 3.9 5.8 0.133, 0.133 60 Comparative Experimental Example 2-2 CE4 4.1 6.6 0.134, 0.132 40

As shown in Table 2, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound exhibited excellent efficiency and lifetime as compared with Comparative Experimental Example.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: light emitting layer 8: electron transporting layer

Claims (13)

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

In Formula 1,
X < ₁ > is O or S,
A is

; Or at least one

_Lt; RTI ID = 0.0 > C6- < / RTI >
Y ₁ to Y ₃ are each independently N or CR ₃ , at least one of Y ₁ to Y ₃ is N,
L ₁ is a bond; Or C _6-60 arylene,
Ar ₁ and Ar ₂ are each independently a C _6-60 aryl; Or C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,
R ₁ to R ₃ are hydrogen,
a1 and a2 are each independently an integer of 0 to 3,
n is 1 or 2,
m is one.
The method according to claim 1,
A is any one selected from the group consisting of:
compound:

In the above,
n is independently 1 or 2;
3. The method of claim 2,
A is any one selected from the group consisting of:
compound:

The method according to claim 1,
Y ₁ , Y ₂ and Y ₃ are N,
compound.
The method according to claim 1,
L < ₁ > is a bond, or any one selected from the group consisting of:
compound:

.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

In the above,
Z ₁ to Z ₄ are hydrogen,
c1 to c3 each independently represent an integer of 0 to 3;
The method according to claim 6,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

delete The method according to claim 1,
The compound is represented by the following general formula (1-1) or (1-2)
compound:
[Formula 1-1]

[Formula 1-2]

In the above formulas 1-1 and 1-2,
X ₁ , Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ and A are the same as defined in claim 1.
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of the following compounds:
compound:

A first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is formed of a material selected from the group consisting of any one of items 1 to 7, 9 and 10 And a compound according to one of the claims.
12. The method of claim 11,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or a layer which simultaneously performs electron injection and electron transport,
Organic light emitting device.
12. The method of claim 11,
The organic compound layer containing the compound is a light-
Organic light emitting device.

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