KR101978453B1 - Novel hetero-cyclic 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 heterocyclic 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,

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 and L ₂ are each independently 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,

Ar ₃ is substituted or unsubstituted C _6-60 aryl, except for substituted or unsubstituted fluorenyl,

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, a2, b1 and b2 each independently represent an integer of 0 to 3;

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 L₁ 및 L₂로 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 ₁ and L ₂ .

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 furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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).

In Formula 1,

X < ₁ >

Also,

Y ₁ is N, Y ₂ and Y ₃ are CR ₅ ,

Y ₂ is N, Y ₁ and Y ₃ are CR ₅ ,

Y ₁ and Y ₂ are N, Y ₃ is CR ₅ ,

Y ₁ and Y ₃ are N, Y ₂ is CR ₅ , or

Y ₁ , Y _2, and Y ₃ may be N.

E.g,

Y ₁ is N, Y ₂ and Y ₃ are CH,

Y ₂ is N, Y ₁ and Y ₃ are CH,

Y ₁ and Y ₂ are N, Y ₃ is CH,

Y ₁ and Y ₃ are N, Y ₂ is CH, or

Y ₁ , Y ₂ and Y ₃ may be N.

Further, L ₁ and L ₂ each independently may be bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene. Here, a1 and a2 may each independently be 0 or 1.

For example, L ₁ and L ₂ can each independently be a bond,

.

.

For example, L < _{1 >} and L < ₂ > may be a bond.

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; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,

c1 and c2 are each independently an integer of 0 to 3;

Wherein Z ₁ and Z ₂ are each independently selected from the group consisting of hydrogen; heavy hydrogen; Cyano; Phenyl; Biphenyl; Pyridinyl; Or pyridinylphenyl, and Z ₃ and Z ₄ may be methyl.

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

Ar ₃ may be any one selected from the group consisting of:

In the above,

Z ₁₁ to Z ₁₃ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Si (Q ₁ ) (Q ₂ ) (Q ₃ ); C (Q ₄ ) (Q ₅ ) (Q ₆ ) and C _6-60 aryl,

Here, Q ₁ - Each Q < ₆ > is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; methyl; Or phenyl,

c11 to c13 are each independently an integer of 0 to 3;

More specifically, in the above, Z ₁₁ to Z ₁₃ each independently represent hydrogen; heavy hydrogen; Si (phenyl) ₃ ; C (phenyl) ₃ ; Phenyl; Biphenyl; Naphthyl; Phenylnaphthyl; Or triphenylenyl.

For example, Ar < ₃ > may be any one selected from the group consisting of:

Each of R ₁ to R ₃ independently represents hydrogen; heavy hydrogen; halogen; Cyano; Amino; methyl; Or b1 and b2 each independently may be 0 or 1. [

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

In this case, a1 represents the number of L ₁ , and when a ₁ is 2 or more, L 2 of 2 or more may be the same or different from each other. a2, b1, b2, c1, c2 and c11 to c13 can be understood with reference to the description of a1 and the structure of the above formula.

In addition, the compound may be represented by the following general formula (1-1)

[Formula 1-1]

In Formula 1-1,

X ₁ , Y ₁ to Y _3, and Ar ₁ to Ar ₃ are the same as defined in Formula 1 above.

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

The compound represented by Formula 1 has a structure in which a 6-membered heterocyclic group containing at least one N atom and a structure in which the above-mentioned Ar ₃ substituent group is connected to a specific position of dibenzofuran or dibenzothiophene core, The organic light emitting device can have high efficiency, low driving voltage, high brightness and long life.

The compound represented by Formula 1-1 may be prepared, for example, according to the following Scheme 1. The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

In the above Reaction Scheme 1, X ₁ , Y ₁ to Y _3, and Ar ₁ to Ar ₃ are as defined in Formula 1, and each X independently represents a halogen.

The compound represented by the formula (1) can be prepared by appropriately substituting the starting material in accordance with the structure of the compound to be prepared with reference to Reaction Scheme 1.

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).

In addition to the organic layer, the organic light emitting diode may further include an electron blocking layer (EBL) disposed between the hole transport layer and the light emitting layer and / or a hole blocking layer between the emission layer and the electron transport layer, layer: HBL). In such a structure, the compound represented by Formula 1 may be included in at least one of the electron blocking layer and the hole blocking layer. The electron blocking layer and the hole blocking layer may be organic layers adjacent to the light emitting layer, respectively.

At this time, the compound represented by Formula 1 may be included in the light emitting layer, the electron transporting layer, or the hole blocking layer.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, 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 invention will be described in more detail in the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Manufacturing Example]

Preparation Example 1: Synthesis of Intermediates Al to A4

(1) Preparation of intermediate A1

Iodobenzene-1,3-diol (100 g, 0.42 mol) and (3-chloro-2-fluorophenyl) boronic acid (81.3 g, 0.47 mol) were added to a 2000 mL round bottom flask in a nitrogen atmosphere, (Tri- tert -butylphosphine) palladium (0) (2.17 g, 4.23 mmol) dissolved in 500 ml of water was added to the mixture, and the mixture was stirred for 1 hour Lt; / RTI > (80.2 g, yield: 79%, MS: [M + H] < + > ] ⁺ = 239).

(2) Preparation of intermediate A2

Intermediate A1 (80.2 g, 0.33 mol) and potassium carbonate (139 g, 1.01 mol) were dissolved in 400 mL of N-methyl-2-pyrrolidone and the mixture was heated with stirring for 1 hour. The temperature is lowered to room temperature and the solution is reprecipitated in water. (53.2 g, yield 72%, MS: [M + H] < ⁺ >) was obtained by completely dissolving in dichloromethane, washing with water, drying with anhydrous magnesium sulfate, concentration under reduced pressure, recrystallization using ethanol, 219).

(3) Preparation of intermediate A3

To a solution of Intermediate A2 (53.2 g, 0.23 mol) in 75 mL of acetonitrile was added calcium carbonate (47.3 g, 0.34 mol) dissolved in 100 mL of water, followed by addition of nonafluorobutanesulfonyl fluoride (45.2 mL, 0.25 mol) is slowly added dropwise over 25 minutes. Thereafter, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered and completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol and dried to obtain the intermediate A3 (83.3 g, yield: 73% M + H] < ⁺ > = 501).

(4) Preparation of intermediate A4

Intermediate A3 (83.3 g, 0.17 mol) , 4,4,5,5- tetramethyl- [1, 3, 2-dioxaborolan (42.2 g, 0.17 mol), Pd (dba) 2 (2.87 g, 4.99 mmol), PCy ₃ (2.80 g, 9.98 mmol) and KOAc (48.9 g, 0.50 mol) were placed in dioxane (900 mL) and stirred at reflux for 7 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. Intermediate A4 was obtained (50.3 g, 92% yield, MS: [M + H] ⁺ = 329).

Production Example 2: Synthesis of Compound of Intermediate 1-2

(1) Preparation of intermediate 1-1

Intermediate A4 (20.0 g, 0.06 mol) and 4-bromobiphenyl (14.2 g, 0.06 mmol) were dissolved in 200 mL of tetrahydrofuran, potassium carbonate (25.2 g, 0.18 mol) dissolved in 60 mL of water was added, Tetrakis- (triphenylphosphine) palladium (2.1 g, 1.83 mmol) was added thereto, followed by heating with stirring for 7 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 using a mixed solvent of chloroform and ethyl acetate and dried to obtain Intermediate 1-1 (17.8 g, yield 82 %, MS: [M + H] < ⁺ > = 355).

(2) Preparation of intermediate 1-2

A mixture of intermediate 1-1 (17.8 g, 0.05 mol), 4,4,5,5-tetramethyl- [1,3,2] -dioxaborolane (12.7 g, 0.05 mol), Pd (dba) ₂ , 1.51 mmol), PCy ₃ (0.84 g, 3.00 mmol) and KOAc (14.7 g, 0.15 mol) were placed in dioxane (180 mL) and stirred at reflux for 8 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. Intermediate 1-2 was obtained (15.0 g, yield 91%, MS: [M + H] < ⁺ > = 447).

Preparation Example 3: Synthesis of Compound of Intermediate 2-2

Intermediate 2-2 was prepared in the same manner as Intermediate 1-2, except that 3-bromobiphenyl was used instead of 4-bromobiphenyl.

Production Example 4: Synthesis of Compound of Intermediate 3-2

Intermediate 3-2 was prepared in the same manner as Intermediate 1-2, except that 4-bromobuthenyl was used instead of 4-bromobiphenyl.

Preparation Example 5: Synthesis of Compound of Intermediate 4-2

Intermediate 4-2 was prepared in the same manner as in the preparation of intermediate 1-2, except that 5'-bromo-1,1 ': 3', 1 "-terphenyl was used instead of 4-bromobiphenyl Respectively.

Preparation Example 6: Synthesis of Intermediate 5-2 Compound

4-bromo-5'-phenyl-1,1 ': 3', 1 "-terphenyl was used in place of 4-bromobiphenyl, Intermediate 5 -2.

Preparation Example 7: Synthesis of Compound of Intermediate 6-2

Intermediate 6-2 was prepared in the same manner as Intermediate 1-2, except that 2-bromophenanthrene was used instead of 4-bromobiphenyl.

Production Example 8: Synthesis of Compound of Intermediate 7-2

Intermediate 7-2 was prepared in the same manner as Intermediate 1-2, except that 9-bromophenanthrene was used instead of 4-bromobiphenyl.

Production Example 9: Synthesis of Compound of Intermediate 8-2

Intermediate 8-2 was prepared in the same manner as Intermediate 1-2, except that 2-bromotriphenylene was used instead of 4-bromobiphenyl.

Preparation Example 10: Synthesis of Compound 9-2

Intermediate 9-2 was prepared in the same manner as Intermediate 1-2, except that 3-bromofluoranthene was used instead of 4-bromobiphenyl.

[Example]

Example 1: Synthesis of Compound 1

Intermediate 1-2 (8.0 g, 0.018 mol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.80 g, 0.018 mol) were dissolved in 100 mL of tetrahydrofuran in a nitrogen atmosphere Potassium carbonate (7.43 g, 0.053 mol) dissolved in 70 ml of water was added, and tetrakis- (triphenylphosphine) palladium (0.62 g, 0.54 mmol) was added thereto, followed by heating and stirring for 10 hours. The temperature was lowered to room temperature and filtered. After dissolving in chloroform and washing with water, water is removed with MgSO ₄ and the solvent is removed. Subsequently, recrystallization was performed using a mixed solution of tetrahydrofuran and ethyl acetate to prepare Compound 1 as a white solid. (7.8 g, yield 79%, MS: [M + H] < ⁺ > = 552)

Example 2: Synthesis of Compound 2

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl- Compound 2 as a white solid was prepared in the same manner as Compound 1 was prepared. (Yield: 82%, MS: [M + H] < ⁺ > = 628)

Example 3: Synthesis of Compound 3

Compound 3 as a white solid was prepared in the same manner as in the preparation of Compound 1, except that Intermediate 2-2 was used instead of Intermediate 1-2. (Yield: 74%, MS: [M + H] < ⁺ > = 552)

Example 4: Synthesis of Compound 4

Intermediate 2-2 and 2- (4-chloro-6-phenyl-l, 3,5-triazine-l, 2-yl) -9-phenyl-9H-carbazole was used, Compound 4 was prepared in the same manner as Compound 1 was prepared. (Yield: 82%, MS: [M + H] < ⁺ > = 717)

Example 5: Synthesis of Compound 5

Compound 5 as a white solid was prepared in the same manner as Compound 1 except that Intermediate 3-2 was used instead of Intermediate 1-2. (Yield: 79%, MS: [M + H] < ⁺ > = 628)

Example 6: Synthesis of Compound 6

Intermediate 3-2 and 2 - ([1,1'-biphenyl] -3-yl) -4-tert- Compound 6 was prepared in the same manner as Compound 1 except that chloro-6-phenyl-1,3,5-triazine was used. (Yield: 71%, MS: [M + H] < ⁺ > = 704)

Example 7: Synthesis of Compound 7

Synthesis of Intermediate 4-2 and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine, the compound 7 was prepared in the same manner as the compound 1 was prepared. (Yield: 77%, MS: [M + H] < ⁺ > = 718)

Example 8: Synthesis of Compound 8

Synthesis of Intermediate 4-2 and 2 - ([1,1'-biphenyl] -4-yl) -4- (2-chloro-4,6- Compound 8 was prepared in the same manner as Compound 1 except for using chloro-6-phenyl-1,3,5-triazine. (Yield: 84%, MS: [M + H] < ⁺ > = 704)

Example 9: Synthesis of Compound 9

Compound 9 was prepared in the same manner as Compound 1 except for using Intermediate 5-2 instead of Intermediate 1-2. (Yield 81%, MS: [M + H] < ⁺ > = 704)

Example 10: Synthesis of Compound 10

Compound 1 was prepared in the same manner as Intermediate 1 except that Intermediate 2-2 and 2-chloro-4,6-diphenylpyrimidine were used instead of Intermediate 1-2 and 2-chloro-4,6-diphenyl-1,3,5- Compound 10 was prepared in the same manner as the preparation method. (Yield: 78%, MS: [M + H] < ⁺ > = 703)

Example 11: Synthesis of Compound 11

Compound 11 was prepared in the same manner as compound 1 except that Intermediate 6-2 was used instead of Intermediate 1-2. (Yield: 74%, MS: [M + H] < ⁺ > = 576)

Example 12: Synthesis of Compound 12

Intermediate 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used instead of intermediate 6-2 and 2- (3-bromophenyl) , 5-triazine was used instead of 5-thiophene, compound 12 was prepared in the same manner as compound 1 was prepared. (Yield: 72%, MS: [M + H] < ⁺ > = 651)

Example 13: Synthesis of Compound 13

Compound 1 was prepared in a similar manner to Intermediate 1-2 except that Intermediate 7-2 and 4-chloro-2,6-diphenylpyrimidine were used instead of Intermediate 1-2 and 2-chloro-4,6-diphenyl-1,3,5- Compound 13 was prepared in the same manner as the preparation method. (Yield: 70%, MS: [M + H] < ⁺ > = 575)

Example 14: Synthesis of Compound 14

Compound 14 was prepared in the same manner as Compound 1 except that Intermediate 8-2 was used instead of Intermediate 1-2. (Yield 76%, MS: [M + H] < ⁺ > = 626)

Example 15: Synthesis of compound 15

Synthesis of Intermediate 8-2 and 2 - ([1,1'-biphenyl] -3-yl) -4-tert- Compound 15 was prepared in the same manner as Compound 1 except that chloro-6-phenyl-1,3,5-triazine was used. (Yield: 71%, MS: [M + H] < ⁺ > = 702)

Example 16: Synthesis of Compound 16

Synthesis of Intermediate 9-2 and 2 - ([1,1'-biphenyl] -3-yl) -4- (2-chloro-4,6- Compound 16 was prepared in the same manner as Compound 1 except that chloro-6-phenyl-1,3,5-triazine was used. (Yield 79%, MS: [M + H] < ⁺ > = 676)

[Experimental Example]

Experimental Example 1

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited to a thickness of 250 Å on the hole injection layer to form a hole transport layer, and the HT-2 compound was vacuum deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer.

Subsequently, compound 1 and the following phosphorescent dopant (DP) were co-deposited on the electron blocking layer to form a light emitting layer having a thickness of 400 Å. At this time, the content of the phosphorescent dopant was controlled to 12 wt% with respect to 100 wt% of the total light emitting layer.

On the light emitting layer, the following ET-1 compound was vacuum deposited to a thickness of 250 ANGSTROM to form an electron transporting layer. On the electron transporting layer, the following ET-2 compound and Li were co-deposited to a thickness of 100 ANGSTROM to form an electron injecting layer. At this time, the Li content was controlled to 2 wt% with respect to 100 wt% of the total electron injecting layer. Thereafter, aluminum was deposited on the electron injection layer to a thickness of 1000 Å to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 < ^-8 > torr.

Experimental Examples 2 to 9

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compounds described in the following Table 1 were used in place of Compound 1 as a host in forming the light emitting layer. In this case, when a mixture of two kinds of compounds is used as a host, the parentheses indicate the weight ratio of the host. In the following Table 1, the H2 compound is as follows.

Comparative Experimental Examples 1 to 4

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compounds described in the following Table 1 were used in place of Compound 1 as a host in forming the light emitting layer. In this case, when a mixture of two kinds of compounds is used as a host, parentheses mean the weight ratio between hosts. In the following Table 1, the C1 to C3 compounds are as follows.

The voltage and efficiency were measured by applying a current of 10 mA / cm ² to the organic light emitting device manufactured in Experimental Examples 1 to 9 and Comparative Experimental Examples 1 to 4, and the lifetime was measured by applying a current of 20 mA / cm ² . The results are shown in Table 1 below. In the following Table 1, T95 represents the time required for the luminance to be reduced to 95% from the initial luminance.

Host Voltage
(V, @ 10 mA / cm ² ) efficiency
(cd / A, @ 10 mA / cm ² ) Color coordinates
(x, y) life span
(T95, h,
@ 20 mA / cm ² ) Experimental Example 1 Compound 1 3.2 70 0.44, 0.54 48 Experimental Example 2 Compound 3 3.1 72 0.44, 0.54 46 Experimental Example 3 Compound 5 3.1 73 0.43, 0.54 47 Experimental Example 4 Compound 10 3.0 70 0.45, 0.54 49 Experimental Example 5 Compound 12 3.1 75 0.45, 0.53 48 Experimental Example 6 Compound 15 3.1 72 0.44, 0.53 49 Experimental Example 7 Compound 1: H2
(50:50) 3.6 79 0.45, 0.54 165 Experimental Example 8 Compound 5: H2
(50:50) 3.5 79 0.43, 0.53 161 Experimental Example 9 Compound 9: H2
(50:50) 3.6 81 0.43, 0.53 164 Comparative Experimental Example 1 C1: H2
(50:50) 3.5 67 0.45, 0.54 140 Comparative Experimental Example 2 C1 3.0 60 0.46, 0.53 40 Comparative Experimental Example 3 C2 2.9  62.2 0.48, 0.50 41 Comparative Experimental Example 4 C3 3.1 58 0.45, 0.54 33

As shown in Table 1, when the compound of the present invention was used as a host, it was confirmed that the compound exhibited excellent characteristics in terms of efficiency and lifetime in comparison with the comparative experiment using Compound C1.

In addition, when the compound of the present invention was used as a host, it was confirmed that the efficiency was increased by 20% or more as compared with Comparative Example using Compound C2. It was confirmed that the efficiency characteristics were influenced by the substitution position of dibenzofurane. Specifically, in terms of the balance of holes and electrons from the adjacent layers of the device, it is interpreted that the substituent is located at positions 1 and 6 rather than positions 4 and 6 of the structure dibenzofuran, I could.

Further, Comparative Experiment 4 using Compound C3 substituted with dimethylfluorenyl group exhibited a lower life than Examples 1 and 5 using a compound in which a biphenyl group and a phenanthrenyl group were respectively substituted, It can be interpreted that it is caused by generation of impurities generated by radical formation by dimethylfluorenyl at the time of driving.

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 (14)

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

In Formula 1,
X < ₁ > is O or S,
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 and L ₂ are each independently a bond; Or C _6-60 arylene,
Ar ₁ and Ar ₂ are each independently a C _6-60 aryl substituted or unsubstituted with cyano; 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 each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-60 alkyl; C _1-60 haloalkyl; C _1-60 alkoxy; C _1-60 haloalkoxy; C _3-60 cycloalkyl; C _2-60 alkenyl; C _6-60 aryl; C _6-60 aryloxy; Or a C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,
a1, a2, b1 and b2 each independently represents an integer of 0 to 3,
Ar ₃ is any one selected from the group consisting of

The method according to claim 1,
Y ₁ is N, Y ₂ and Y ₃ are CH,
Y ₂ is N, Y ₁ and Y ₃ are CH,
Y ₁ and Y ₂ are N, Y ₃ is CH,
Y ₁ and Y ₃ are N, Y ₂ is CH, or
Y ₁ , Y ₂ and Y ₃ are N, compound.
The method according to claim 1,
L ₁ and L ₂ are each independently selected from the group consisting of a bond or a group consisting of:

.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently 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; C _6-20 aryl; Or a C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,
c1 and c2 are each independently an integer of 0 to 3;
5. The method of claim 4,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

delete delete The method according to claim 1,
Wherein R ₁ to R ₃ are hydrogen.
The method according to claim 1,
Wherein the compound is represented by the following formula 1-1:
[Formula 1-1]

In Formula 1-1,
X ₁ , Y ₁ to Y ₃ and Ar ₁ to Ar ₃ 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:

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 5 and 8 to 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 a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes.
12. The method of claim 11,
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.
12. The method of claim 11,
Wherein the organic compound layer containing the compound is a light emitting layer.

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