KR101937996B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel triazine-based 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 triazine-based 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 triazine-based 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 to X ₅ are each independently N or CR ₄ , at least one of X ₁ to X ₅ is N,

L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted O, N, C _1-60 heteroaryl containing 1 or more heteroatoms selected from the group consisting of Si and S arylene,

n is 1 or 2,

Ar is substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted N, O, and C _1-60 heteroaryl comprising 1 to 3 heteroatoms selected from the group consisting of S aryl,

m is an integer of 0 to 2,

R ₁ to R ₄ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; 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 _1-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,

a1 is an integer of 0 to 5,

a2 is an integer of 0 to 7,

a3 is an integer of 0 to 4,

m + a1 and n + a3 are each 5 or less.

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.

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

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

Means a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L. [

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 heterocyclic 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 1 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.

를 A로 표시하는 경우, On the other hand, in the above formula (1)

Is represented by A,

The formula 1 may be represented by the following formulas 1-1 to 1-9 according to the bonding position of A:

In the above formulas 1-1 to 1-9, A ₁ and A ₂ each independently represent the same as or different from each other with reference to the description of A.

For example, A ₁ and A ₂ may be the same as each other.

According to one embodiment,

X ₁ is N, X ₂ , X ₃ , X ₄ and X ₅ are CR ₄ ,

X ₂ is N, X ₁ , X ₃ , X ₄ and X ₅ are CR ₄ , or

X ₃ is N, and X ₁ , X ₂ , X _4, and X ₅ may be CR ₄ .

E.g,

X ₁ is N, X ₂ , X ₃ , X ₄ and X ₅ are CH,

X ₂ is N, X ₁ , X ₃ , X ₄ and X ₅ are CH, or

X ₃ is N, and X ₁ , X ₂ , X _4, and X ₅ may be CH.

According to one embodiment, L is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted Anthracenylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted fluorenylene , Or substituted or unsubstituted spiro-fluorenylene.

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

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

According to one embodiment, n may be 1 or 2. In this case, n represents the number of substituent A, and when n is 2 or more, 2 or more A's may be the same or different from each other.

According to one embodiment, Ar may be substituted or unsubstituted C _6-20 aryl.

For example, Ar is substituted or unsubstituted phenyl; Substituted or unsubstituted biphenyl; Substituted or unsubstituted terphenyl; Substituted or unsubstituted naphthyl; Substituted or unsubstituted fluorenyl; Substituted or unsubstituted phenanthrenyl; Substituted or unsubstituted anthracenyl; Substituted or unsubstituted fluoranthenyl; Substituted or unsubstituted triphenylenyl; Substituted or unsubstituted pyrenyl; Substituted or unsubstituted chlorenyl; Substituted or unsubstituted fluorenyl; Substituted or unsubstituted spiro-fluorenyl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted benzocarbazolyl; Substituted or unsubstituted dibenzofuranyl; Or substituted or unsubstituted dibenzothiophenyl.

Specifically, for example, Ar may be phenyl.

According to one embodiment, m can be 0, 1, or 2. For example, m may be 0 or 1. In this case, n represents the number of the substituent Ar, and when m is 2 or more, two or more Ar may be the same or different from each other.

According to one embodiment, R ₁ to R ₄ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; C _1-20 alkyl; Or C _6-20 aryl.

For example, R ₁ to R ₄ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; methyl; Or phenyl, and a1 to a3 may each independently be 0 or 1.

Specifically, for example, R ₁ to R ₄ may be hydrogen.

In this case, a1 is shown as the number of R1, it is possible to case a1 is 2 or more, two or more of R ₁ are the same or different from each other. a2 and a3 can be understood with reference to the description of a1 and the structure of the formula (1).

On the other hand, the compound may be represented by one of the following formulas (2) to (5):

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

X ₁₁ to X ₁₆ are each independently N or CH,

One of X ₁₁ to X ₁₃ and one of X ₁₄ to X ₁₆ is N,

Ar is substituted or unsubstituted C _6-20 aryl,

m is 0 or 1,

L ₁ and L ₂ refer to the description of L in the above formula (1).

Specifically,

Ar is phenyl,

L ₁ and L ₂ each independently may be a single bond or phenylene.

For example, the compound may be any one selected from the group consisting of the following compounds 1 to 34:

The compound represented by the formula (1) has a structure in which a phenyl group, a dibenzofuranyl group and a 6-membered heteroarylphenyl group containing at least one N atom are connected to the triazine core, and the organic light emitting device using the same has a high efficiency, Voltage, high brightness and long life.

The compound represented by the formula (1) can be prepared by the following reaction scheme (1). The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

The reaction is a step of reacting the compound represented by the formula (1-a) with the compound represented by the formula (1-b) to prepare the compound represented by the formula (1). 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. In the above Reaction Scheme 1, the definitions other than X 'are as defined above, and X' is halogen, preferably chloro or bromo. The above production method can be more specific in the production example to be described later.

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 1-1

4-Bromodibenzofuran (Compound A-1, 10 g, 40 mmol) was added to 500 mL of anhydrous tetrahydrofuran and cooled to -78 ° C. Then, n-butyllithium (18 mL, 45 mmol) was slowly added dropwise over 30 minutes while stirring, followed by reaction for 1 hour. Then, dimethylcarbamyl chloride (5 g, 49 mmol) was added thereto, slowly warmed to room temperature, and reacted for 4 hours. After the reaction was terminated by pouring water, the water layer and the organic layer were separated, and the organic layer was subjected to distillation under reduced pressure to obtain Compound A-2 (5.3 g, 55%). (Z) -N'-cyanobenzimidamide (4 g, 27 mmol) was added thereto while stirring, and the mixture was refluxed with 3 mL of phosphorus oxychloride and 200 mL of acetonitrile. The resulting solid was filtered and the filtrate was again dissolved in chloroform, neutralized and extracted with water saturated with calcium carbonate, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethanol. The resulting solid was filtered and dried to give Compound 1-1 (6 g, 71%).

MS: [M + H] < ⁺ > = 358

Manufacturing example  2: Preparation of Compound 1-2

Compound 1-2 was prepared in the same manner as in Preparation Example 1-1 except that 3-bromodibenzofuran was used instead of 4-bromodibenzofurane.

MS: [M + H] < ⁺ > = 344

Manufacturing example  3: Preparation of compound 1-3

Compound 1-3 was prepared in the same manner as in Production Example 1-1 except that 2-bromodibenzofuran was used instead of 4-bromodibenzofurane.

MS: [M + H] < ⁺ > = 344

Manufacturing example  4: Preparation of compounds 1-4

Compound 1-4 was prepared in the same manner as in Production Example 1-1, except that 1-bromodibenzofuran was used instead of 4-bromodibenzofurane.

MS: [M + H] < ⁺ > = 344

Manufacturing example  5: Preparation of Compound 3-1

1) Preparation of Compound 2-1

Compound 10 (10 g, 27.9 mmol) and (3-chlorophenyl) boronic acid (4.4 g, 27.9 mmol) were dissolved in 130 mL of tetrahydrofuran in a nitrogen atmosphere, followed by the addition of a 1.5 M aqueous potassium carbonate solution And tetrakis- (triphenylphosphine) palladium (0.65 g, 0.56 mmol) was added thereto, followed by heating and stirring for 4 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 chloroform and ethanol, and dried to obtain Compound 2-1 (10.4 g, yield 86%).

MS: [M + H] < ⁺ > = 434

2) Preparation of compound 3-1

Bis (pinacolato) diboron (6.70 g, 26.4 mmol) and KOAc (7.1 g, 71.9 mmol) were added to 150 mL of dioxane, and Pd (dba) ₂ 0.41 g, 0.72 mmol) and PCy ₃ (0.4 g, 0.72 mmol) were placed in a 500 ml round-bottomed flask, refluxed and stirred for 10 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 by concentration under reduced pressure, and recrystallized using ethyl acetate. The product was dried to obtain Compound 3-1 (10.8 g, yield 86%).

MS: [M + H] < ⁺ > = 526

Manufacturing example  6: Preparation of compound 3-2

Compound 2-2 and then Compound 3-2 were prepared in the same manner as in Production Example 5, except that Compound 1-3 was used instead of Compound 1-1.

MS: [M + H] < ⁺ > = 526

Manufacturing example  7: Preparation of compound 3-3

Compound 2-3 was obtained in the same manner as in Production Example 5, except that Compound 1-1 and Compound (1-2) and (3,5-dichlorophenyl) boronic acid were used in place of (3-chlorophenyl) Compound 3-3 was then prepared.

MS: [M + H] < ⁺ > = 652

Manufacturing example  8: Preparation of compound 3-4

Compound 2-4 and then Compound 3-4 were prepared in the same manner as in Production Example 5, except that (2,4-dichlorophenyl) boronic acid was used instead of (3-chlorophenyl) boronic acid.

MS: [M + H] < ⁺ > = 652

Manufacturing example  9: Preparation of compound 3-5

Compound 2-5 was obtained in the same manner as in Production Example 5, except that Compound 1-1 and Compound (1-3) and (2,5-dichlorophenyl) boronic acid were used in place of (3-chlorophenyl) Compound 3-5 was then prepared.

MS: [M + H] < ⁺ > = 652

[ Example ]

Example  1: Preparation of compound 1

(10.8 g, 20.6 mmol) and 3- (4-bromophenyl) pyridine (4.81 g, 20.6 mmol) were dissolved in 110 mL of tetrahydrofuran in a nitrogen atmosphere. Potassium carbonate (8.5 g, 61.7 mmol) Was dissolved in 25 mL of water, and tetrakis- (triphenylphosphine) palladium (0.71 g, 0.62 mmol) was added thereto, followed by heating and stirring for 9 hours. The temperature was lowered to room temperature and the water layer was separated and removed. The filtrate was dissolved in chloroform, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Recrystallization was carried out using a mixed solution of tetrahydrofuran and ethyl acetate to obtain Compound 1 (8.5 g, yield 75%).

MS: [M + H] < ⁺ > = 553

Example  2: Preparation of compound 5

Compound 5 was prepared in the same manner as in Example 1, except that Compound 3-2 was used instead of Compound 3-1.

MS: [M + H] < ⁺ > = 553

Example  3: Preparation of compound 12

The compound 3-3 (9.8 g, 18.7 mmol) and 3- (4-bromophenyl) pyridine (8.7 g, 37.3 mmol) were dissolved in 100 mL of tetrahydrofuran in a nitrogen atmosphere, potassium carbonate (7.7 g, 56.0 mmol) (0.65 g, 0.56 mmol) was added to the solution, and the mixture was heated and stirred for 17 hours. The temperature was lowered to room temperature and the water layer was separated and removed. The filtrate was then dissolved in chloroform, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Recrystallization was carried out using a mixed solution of tetrahydrofuran and ethyl acetate to obtain Compound 12 (7.9 g, yield 76%).

MS: [M + H] < ⁺ > = 706

Example  4: Preparation of compound 15

Compound 15 was prepared in the same manner as in Example 3, except that Compound 3-4 was used instead of Compound 3-3.

MS: [M + H] < ⁺ > = 706

Example  5: Preparation of Compound 21

Compound 21 was prepared in the same manner as in Example 3, except that Compound 3-5 was used instead of Compound 3-3.

MS: [M + H] < ⁺ > = 706

[ Experimental Example ]

Experimental Example  One

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water, which was secondly 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 HAT 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. Subsequently, the following BH compound and BD compound were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 to a film thickness of 300 ANGSTROM to form a light emitting layer. The following ET-A compound was vacuum-deposited on the light emitting layer to a thickness of 50 Å to form an a-electron transporting layer. Compound 1 prepared above and the following LiQ compound (Lithium Quinolate) were vacuum deposited on the a-electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and lithium aluminum fluoride (LiF) to a thickness of 2,000 Å 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 the lithium fluoride of the cathode was 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 < ^-6 > torr to manufacture an organic light emitting device.

Experimental Example  2 to Experimental Example  5

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound described in Table 1 was used instead of Compound 1 in forming the electron transport layer.

Comparative Experimental Example  1 to 3

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound shown in Table 1 was used. In the following Table 1, the C1, C2 and C3 compounds are as follows.

The voltage and efficiency were measured by applying current to the organic light emitting device manufactured in the Experimental Examples and Comparative Experimental Examples. 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) Experimental Example 1 Compound 1 3.80 7.31 0.132, 0.133 Experimental Example 2 Compound 5 3.76 7.29 0.133, 0.132 Experimental Example 3 Compound 12 3.77 7.27 0.134, 0.132 Experimental Example 4 Compound 15 3.77 7.30 0.133, 0.135 Experimental Example 5 Compound 21 3.60 7.32 0.134, 0.134 Comparative Experimental Example 1 Compound C1 3.95 4.07 0.131, 0.133 Comparative Experimental Example 2 Compound C2 3.80 5.80 0.133, 0.134 Comparative Experimental Example 3 Compound C3 3.90 7.01 0.134, 0.133

As shown in Table 1, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound of the present invention exhibited excellent efficiency in comparison with the compounds of Comparative Examples 1 to 3.

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 (11)

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

In Formula 1,
X ₁ to X ₅ are each independently N or CR ₄ ,
X ₁ is N, X ₂ , X ₃ , X ₄ and X ₅ are CR ₄ ,
X ₂ is N, X ₁ , X ₃ , X ₄ and X ₅ are CR ₄ , or
X ₃ is N, X ₁ , X ₂ , X ₄ and X ₅ are CR ₄ ,
L is a single bond; Or C _6-60 arylene,
n is 1 or 2,
Ar is C _6-60 aryl,
m is an integer of 0 to 2,
R ₁ to R ₄ are hydrogen,
a1 is 0,
a2 is 0,
a3 is zero.
delete The method according to claim 1,
L is a single bond, or any one selected from the group consisting of:

.
The method according to claim 1,
Ar is phenyl.
The method according to claim 1,
and m is 0 or 1.
delete The method according to claim 1,
Wherein said compound is represented by any one of the following Chemical Formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
X ₁₁ to X ₁₆ are each independently N or CH,
One of X ₁₁ to X ₁₃ and one of X ₁₄ to X ₁₆ is N,
Ar is C _6-20 aryl,
m is 0 or 1,
L ₁ and L ₂ refer to the description of L in the first paragraph.
8. The method of claim 7,
Ar is phenyl,
L ₁ and L ₂ are, each independently, a single bond or phenylene.
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of the following compounds 1 to 34:

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 the organic material layer according to any one of claims 1, 3, 4, 5, And a compound according to any one of claims 1 to 9.
11. The method of claim 10,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously.

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