KR101917857B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

[0001] The present invention relates to novel heterocyclic compounds and organic light emitting devices using the same. More particularly,

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

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

[Chemical Formula 1]

In Formula 1,

A is a benzene ring fused to adjacent pentagonal rings and pyrrole rings,

Ar is substituted C _6-60 aryl, including one or more cyano groups; Or substituted C _1-60 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S, with the exception of phenyl groups substituted with at least two cyano groups,

R ₁ to R ₃ , R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _1-6 haloalkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; 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 and a3 are each independently an integer of 0 to 4,

a2 is an integer of 0 to 2;

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

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

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

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

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

는 다른 치환기에 연결되는 결합을 의미한다.In the present specification,

Quot; means a bond connected to another substituent.

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 . That is, the term "substituent group to which two or more substituents are connected" means that the substituent group may be substituted with one or more of the substituents described above. Thus, the term "substituted or unsubstituted" as used herein refers to a cyanoalkyl group; A cyano cycloalkyl group; A cyanoalkenyl group; A cyano group, and the like. Further, for example, "the substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

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

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

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

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

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

In Formula 1, A is a benzene ring fused with two adjacent pyrrol rings, and may be represented by any one of the following Formulas 1-1 to 1-6, depending on the fused position.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas 1-1 to 1-6,

Ar, R ₁ to R ₃ , R ₁₁ , R ₁₂ and a ₁ to a ₃ are as defined in the above formula (1).

The term " Ar includes one or more cyano groups, wherein one or more cyano groups are included "means that Ar is substituted with one or more cyano groups, or Ar is substituted with one or more cyano groups Substituted "

According to one embodiment, Ar may be any one selected from the group consisting of:

In the above formulas,

X ₁ and X ₂ are each independently N or CZ ₄ ,

n1 is 1, n2 to n5 are each independently an integer of 0 to 3,

n2 + n3 and n4 + n5 are each independently 1 or more,

Z ₁ To Z < ₄ > are each independently hydrogen; heavy hydrogen; halogen; Nitro; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,

c1 is an integer of 0 to 4,

c2 is an integer of 0 to 3;

Specifically,

X ₁ and X ₂ are CH;

X < ₁ > is N and X < ₂ > is CH;

X < ₁ > is CH and X < ₂ > is N; or

X ₁ and X ₂ may be N.

N2 + n3 and n4 + n5 may each independently be 1, 2, 3, or 4;

For example, Ar may comprise one or two cyano groups. Therefore, in the above formula, n2 + n3 and n4 + n5 may each independently be 1 or 2. [ Herein, n1 to n5 each represent the number of cyano groups, n1 is 1; n2 is 1 or 2; n3 is 0 or 1; n4 is 1; n5 may be one.

Also, Z ₁ to Z ₃ may be hydrogen, and c 1 and c 2 may be 0.

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

According to one embodiment, R ₁ to R ₃ , R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Nitro; Amino; C _1-20 alkyl; Or C _6-20 aryl.

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

In addition, R ₁₁ and R ₁₂ may be methyl.

Here, a1 represents the number of R ₁ , and when a ₁ is 2 or more, two or more R _{1 s} may be the same or different from each other. a2 and a3 can be understood with reference to the description of a1 and the structure of the formula (1).

Also, c1 is indicated as the number of Z _1, the case c1 is 2 or more, two or more of Z ₁ may be the same or different from each other. The description of c2 can be understood with reference to the description of c1 and the structure of the above formula.

On the other hand, the compound may be any one selected from compounds represented by the following formulas 1-1-1 to 1-6-1:

[Formula 1-1-1]

[Formula 1-2-1]

[Formula 1-3-1]

[Formula 1-4-1]

[Formula 1-5-1]

[Chemical Formula 1-6-1]

In the above formulas 1-1-1 to 1-6-1,

The definition of Ar is the same as defined in claim 1.

For example, the compound may be selected from the group consisting of the following compounds:

The compound represented by Formula 1 is an N substituent of an indolofluorene core and contains Ar having two or more cyano groups. The organic light emitting device using the compound has high efficiency, low driving voltage, high brightness and long life have.

The compounds represented by the formulas 1-1-1 to 1-4-1 may be prepared, for example, according to the following reaction schemes 1 to 3, respectively. The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

In the above Reaction Schemes 1 to 3, the description of Ar is as defined in claim 1, "X" means halogen, and "t-Bu" means tert-butyl.

Also, the present invention provides an organic light emitting device including 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 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 and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transport layer is a layer that transports electrons from the electron injection layer to the electron transport layer and transports electrons from the electron injection layer. The electron transport 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 with a low work function followed by an aluminum layer or 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 the 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.

Production Example A-1: Preparation of Intermediates A and B

1) Preparation of intermediate A1

(50.0 g, 0.25 mol) and (2- (2-hydroxypropan-2-yl) phenyl) boronic acid (49.1 g, 0.27 mol) were dissolved in 500 mL of dioxane in a nitrogen atmosphere. After dissolving, K ₃ PO ₄ (131.5 g, 0.62 mol) was added, and bis (tri-tert-butylphosphine) palladium (1.2 g, 2.5 mmol) was added and the mixture was heated with stirring for 8 hours. (60.8 g, yield 81%, MS: [M + H] +) was prepared by reducing the temperature to room temperature, separating the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, recrystallization using ethyl acetate, H] < ⁺ > = 302).

2) Preparation of intermediates A and B

In a nitrogen atmosphere, Intermediate A1 (75.2 g, 0.20 mol) and 390 mL of acetic acid were added, 1.4 mL of H ₂ SO ₄ was slowly added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. This was purified by column chromatography to separate intermediate A and intermediate B.

Production Example A-2: Preparation of Intermediate C

1) Preparation of intermediate C1

Intermediate C1 was prepared in the same manner as Intermediate A1 except for using 3-chloro-9H-carbazole (45.0 g, 0.22 mol) instead of 2-chloro-9H-carbazole (55.2 g, yield 82 %, MS: [M + H] < ⁺ > = 302).

2) Preparation of intermediate C

In a nitrogen atmosphere, Intermediate C1 (55.2 g, 0.18 mol) and 300 mL of acetic acid were added, and 1.1 mL of H ₂ SO ₄ was slowly added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. Intermediate C was obtained (44.7 g, yield 88%, MS: [M + H] ⁺ = 284) using ethyl acetate.

Production Example A-3: Preparation of Intermediate D

1) Preparation of intermediate D1

(60.0 g, 0.29 mol) was dissolved in CHCl _{3 (} 500 mL), NBS (46.8 g, 0.29 mol) was added in 5 portions at 0 ° C, and the mixture was stirred at room temperature And stirred for 1 hour. Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water, and then the organic layer was separated and reduced in pressure to remove any solvent. This was subjected to column chromatography to obtain intermediate D1 (67.1 g, yield 81%, MS: [M + H] ⁺ = 288).

2) Preparation of intermediate D2

After dissolving Intermediate D1 (67.1 g, 0.23 mol) and (2-chlorophenyl) boronic acid (31.2 g, 0.26 mol) in 660 mL of tetrahydrofuran, a 1.5 M aqueous potassium carbonate solution (200 mL) (Tert-butylphosphine) palladium (1.2 g, 2.3 mmol) were added thereto, followed by heating and stirring for 2 hours. (56.4 g, yield 76%, MS: [M + H] < + >, M < + > H). The mixture was stirred at room temperature for 2 hours, ] ⁺ = 320).

3) Preparation of intermediate D

(56.4 g, 0.18 mol) and K ₂ CO ₃ (48.7 g, 0.35 mol) were dissolved in 550 mL of dimethylacetamide, and Pd (OAc) ₂ (4.0 g, 17.6 mmol) Lt; / RTI > The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. Recrystallization with ethyl acetate gave 42.4 g (85% yield, MS: [M + H] < ⁺ > = 284).

Production Example A-4: Preparation of Intermediate E

1) Preparation of intermediate E1

Intermediate E1 was prepared in the same manner as Intermediate A1 except that 1-chloro-9H-carbazole (50.0 g, 0.25 mol) was used instead of 2-chloro-9H-carbazole (61.2 g, yield 82 %, MS: [M + H] < ⁺ > = 302).

2) Preparation of intermediate E

Intermediate E was prepared in the same manner as Intermediate C except for using Intermediate E1 instead of Intermediate C1.

Production Example A-5: Preparation of Intermediate G

1) Preparation of intermediate G1

Intermediate G1 was prepared in the same manner as Intermediate Al except that 4-chloro-9H-carbazole was used instead of 2-chloro-9H-carbazole.

2) Preparation of intermediate G

Intermediate G was prepared in the same manner as Intermediate C except for using Intermediate G1 instead of Intermediate C1.

Production Example A-6: Preparation of intermediate b

3-bromobenzonitrile (a, 30.0 g, 0.16 mol) and 4-chlorophenylboronic acid (28.4 g, 0.16 mol) were dissolved in 300 mL of tetrahydrofuran in a nitrogen atmosphere, and a 1.5 M aqueous potassium carbonate solution (100 mL) And tetrakis- (triphenylphosphine) palladium (3.8 g, 3.30 mmol) was added thereto, followed by heating with stirring for 5 hours. (30.7 g, yield 87%, MS: [M + H] +) was prepared by reducing the temperature to room temperature, separating the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, recrystallization using chloroform and ethanol, H] < ⁺ > = 214).

Production Example A-7: Preparation of intermediate d

Intermediate d was prepared in the same manner as Intermediate b except for using 4-bromobenzonitrile (c) instead of Intermediate a.

Production Example A-8: Preparation of intermediate e

Intermediate e was prepared in the same manner as Intermediate b except that 3-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid.

Production Example A-9: Preparation of intermediate f

Intermediate f was prepared in the same manner as Intermediate b except that Intermediate a and Intermediate b and 3-chlorophenylboronic acid were used instead of 4-chlorophenylboronic acid.

Production Example A-10: Preparation of Intermediate h

Intermediate h was prepared in the same manner as Intermediate b except that 2-bromobenzonitrile was used instead of Intermediate a.

Production Example A-11: Preparation of intermediate i

Intermediate i was prepared in the same manner as Intermediate b except that 2-bromobenzonitrile and 3-chlorophenylboronic acid were used instead of Intermediate a and 4-chlorophenylboronic acid.

Production Example A-12: Preparation of intermediate j

Intermediate j was prepared in the same manner as Intermediate b except that 5-bromoisophthalonitrile was used instead of Intermediate a.

Production Example A-13: Preparation of intermediate k

Intermediate k was prepared in the same manner as Intermediate b except that 5-bromoisophthalonitrile and 3-chlorophenylboronic acid were used instead of Intermediate a and 4-chlorophenylboronic acid.

Production Example A-14: Preparation of Intermediate l

An intermediate was prepared in the same manner as in the preparation of intermediate b except for using 3-bromo-5-chlorobenzonitrile and (4-cyanophenyl) boronic acid instead of intermediate a and 4-chlorophenylboronic acid.

Production Example A-15: Preparation of intermediate m

Intermediate m was prepared in the same manner as Intermediate b except that 3-bromo-5-chlorobenzonitrile and (3-cyanophenyl) boronic acid were used instead of Intermediate a and 4-chlorophenylboronic acid.

Production Example A-16: Preparation of Intermediate n

(25.0 g, 0.17 mol) and 1,3-dibromo-5-chlorobenzene (23.0 g, 0.08 mol) were dissolved in 290 mL of tetrahydrofuran, and a 1.5 M aqueous potassium carbonate solution (90 mL) And tetrakis- (triphenylphosphine) palladium (3.94 g, 0.34 mmol) was added thereto, followed by heating with stirring for 13 hours. (44.7 g, yield 83%, MS: [M + H] +) was prepared by reducing the temperature to room temperature, separating the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, recrystallization using chloroform and ethanol, H] < ⁺ > = 315).

Production Example A-17: Preparation of intermediate o

Intermediate o was prepared in the same manner as Intermediate b except that (4-cyanophenyl) boronic acid and 4-bromo-6-chloropicolinonitrile were used instead of Intermediate a and 4-chlorophenylboronic acid.

Production Example A-18: Preparation of intermediate p

Intermediate p was prepared in the same manner as Intermediate b except that (3-cyanophenyl) boronic acid and 4-bromo-6-chloropicolinonitrile were used instead of Intermediate a and 4-chlorophenylboronic acid.

Production Example A-19: Preparation of intermediate q

Intermediate q was prepared in the same manner as Intermediate b except that (6-cyanopyridin-3-yl) boronic acid and 4-bromo-6-chloropicolinonitrile were used instead of Intermediate a and 4-chlorophenylboronic acid. Respectively.

Production Example B-1: Preparation of Compound 1

Intermediate A (10.0 g, 35.3 mmol) , intermediate k (8.4 g, 35.3mmol), and _{Cs 2 CO 3 (23.0 g,} 70.6 mmol) was dissolved in the xylene, _{150 mL, Pd (dba) 2} (0.6 g, 1.1 mmol) and xantphos (0.6 g, 1.1 mmol) were added, and the mixture was refluxed and stirred. After 10 hours, the temperature was lowered to room temperature, and the filter was washed with water to remove the base. Compound 1 was prepared (10.3 g, yield 58%, MS: [M + H] ⁺ = 486) by recrystallization using N-methyl-2-pyrrolidone.

Production Example B-2: Preparation of Compound 2

Compound 2 was prepared in the same manner as Compound 1 except that Intermediate n was used instead of Intermediate k. MS: [M + H] < ⁺ > = 562

Production Example B-3: Preparation of Compound 3

Compound 3 was prepared in the same manner as Compound 1 except that Intermediate a was used instead of Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-4: Preparation of Compound 4

Compound 4 was prepared in the same manner as Compound 1 except that Intermediate d was used instead of Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-5: Preparation of Compound 5

Compound 5 was prepared in the same manner as Compound 1 except that Intermediate l was used instead of Intermediate k. MS: [M + H] < ⁺ > = 486

Production Example B-6: Preparation of Compound 6

Compound 6 was prepared in the same manner as Compound 1 except that Intermediate q was used instead of Intermediate k. MS: [M + H] < ⁺ > = 487

Production Example B-7: Preparation of Compound 7

Compound 7 was prepared in the same manner as Compound 1 except that Intermediate h was used instead of Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-8: Preparation of Compound 8

Compound 8 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate b were used instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-9: Preparation of Compound 9

Compound 9 was prepared in the same manner as Compound 1 except for using Intermediate B and Intermediate c in place of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-10: Preparation of Compound 10

Compound 10 was prepared in the same manner as Compound 1 except for using Intermediate B and Intermediate e instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-11: Preparation of Compound 11

Compound 11 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate j were used instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 486

Production Example B-12: Preparation of Compound 12

Compound 12 was prepared in the same manner as Compound 1 except for using Intermediate B and Intermediate o instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 487

Production Example B-13: Preparation of Compound 13

Compound 13 was prepared in the same manner as Compound 1 except for using Intermediate C and Intermediate a in place of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-14: Preparation of Compound 14

Compound 14 was prepared in the same manner as Compound 1 except for using Intermediate C and Intermediate d instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-15: Preparation of Compound 15

Compound 15 was prepared in the same manner as Compound 1 except for using Intermediate C and Intermediate f in place of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-16: Preparation of Compound 16

Compound 16 was prepared in the same manner as Compound 1 except that Intermediate C and Intermediate m were used instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 486

Production Example B-17: Preparation of Compound 17

Compound 17 was prepared in the same manner as Compound 1 except that Intermediate A and Intermediate k were used instead of Intermediate D and Intermediate b. MS: [M + H] < ⁺ > = 461

Production Example B-18: Preparation of Compound 18

Compound 18 was prepared in the same manner as Compound 1 except for using Intermediate D and Intermediate c in place of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-19: Preparation of Compound 19

Compound 19 was prepared in the same manner as Compound 1 except for using Intermediate D and Intermediate e instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-20: Preparation of Compound 20

Compound 20 was prepared in the same manner as Compound 1 except for using Intermediate D and Intermediate i instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-21: Preparation of Compound 21

Compound 21 was prepared in the same manner as Compound 1 except that Intermediate A and Intermediate k were used instead of Intermediate D and Intermediate j. MS: [M + H] < ⁺ > = 486

Production Example B-22: Preparation of Compound 22

Compound 22 was prepared in the same manner as Compound 1 except that Intermediate A and Intermediate k were used instead of Intermediate D and Intermediate l. MS: [M + H] < ⁺ > = 486

Production Example B-23: Preparation of Compound 23

Compound 23 was prepared in the same manner as Compound 1 except that Intermediate A and Intermediate k were used instead of Intermediate D and Intermediate p. MS: [M + H] < ⁺ > = 487

Production Example B-24: Preparation of Compound 24

Compound 24 was prepared in the same manner as compound 1 except that Intermediate A and Intermediate b were used instead of Intermediate k and Intermediate k. MS: [M + H] < ⁺ > = 461

Production Example B-25: Preparation of Compound 25

Compound 25 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate c instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-26: Preparation of Compound 26

Compound 26 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate n instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 562

Production Example B-27: Preparation of Compound 27

Compound 27 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate j instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 486

Production Example B-28: Preparation of Compound 28

Compound 28 was prepared in the same manner as compound 1 except that Intermediate A and Intermediate k were used instead of Intermediate G and Intermediate f. MS: [M + H] < ⁺ > = 461

Production Example B-29: Preparation of Compound 29

Compound 29 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate g instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 385

Production Example B-30: Preparation of Compound 30

Compound 30 was prepared in the same manner as Compound 1 except that Intermediate G and Intermediate k were used instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 486

Production Example B-31: Preparation of Compound 31

Compound 31 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate o instead of Intermediate A and Intermediate k. MS: [M + H] < ⁺ > = 486

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. An HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 Å to form an electron blocking layer. Subsequently, Compound 1 prepared above and the following DP compound were co-deposited on the HT-2 deposited film at a weight ratio of 12% to form a 400 Å thick light emitting layer. The following ET-1 compound was vacuum-deposited on the light-emitting layer to a thickness of 250 ANGSTROM, and the following ET-2 compound was co-deposited with Li at a weight ratio of 2% to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

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

Examples 2 to 16

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

Comparative Examples 1 to 3

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound described in the following Table 1 was used instead of the compound 1 in Example 1. In the following Table 1, C1 to C3 mean the following compounds, respectively.

The driving voltage, the efficiency, the luminescent color, and the lifetime were measured by applying a current to the organic light-emitting device manufactured in the above-described Examples and Comparative Examples, and the results are shown in Table 1 below. In this case, the lifetime (T ₉₅ ) is defined as the time required for the luminance to decrease to 95% when the initial luminance is 100%, and is measured at a current density of 20 mA / cm ² .

compound Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color T ₉₅
(@ 20 mA / cm ² ) Example 1 One 3.30 77.5 green 44 Example 2 2 3.25 72.7 green 48 Example 3 3 3.31 76.5 green 51 Example 4 6 3.37 75.6 green 45 Example 5 7 3.35 73.1 green 50 Example 6 8 3.34 73.3 green 54 Example 7 11 3.32 76.8 green 49 Example 8 13 3.33 73.0 green 52 Example 9 14 3.36 72.9 green 53 Example 10 18 3.35 73.4 green 55 Example 11 19 3.30 73.2 green 51 Example 12 21 3.32 78.1 green 47 Example 13 22 3.33 77.9 green 48 Example 14 23 3.38 77.7 green 46 Example 15 26 3.34 77.4 green 47 Example 16 30 3.33 77.2 green 45 Comparative Example 1 C1 3.01 60.0 green 40 Comparative Example 2 C2 3.86 57.1 green 27 Comparative Example 3 C3 3.90 55.9 green 33

As shown in Table 1 above, it was confirmed that the compound of the present invention is a host material having high-efficiency characteristics compared to Compound C1 which is a conventional green luminescent host material. In addition, compared with the comparative examples C2 and C3, the efficiency is increased by about 30 to 40%, and it is confirmed that the voltage characteristics are relatively low.

While the present invention has been described with reference to the preferred embodiments thereof (the light emitting layer), the present invention is not limited thereto and can be variously modified and embodied within the scope of the claims and the detailed description of the invention, .

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,
A is a benzene ring fused to adjacent pentagonal rings and pyrrole rings,
R ₁ to R ₃ are hydrogen,
R ₁₁ and R ₁₂ are methyl,
a1 and a3 are integers of 4,
a2 is an integer of 2,
Ar is any one selected from the group consisting of:

delete delete delete delete delete The method according to claim 1,
The compound is any one selected from compounds represented by the following formulas (1-1-1) to (1-6-1)
[Formula 1-1-1]

[Formula 1-2-1]

[Formula 1-3-1]

[Formula 1-4-1]

[Formula 1-5-1]

[Chemical Formula 1-6-1]

In the above formulas 1-1-1 to 1-6-1,
The definition of Ar is 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 compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers is formed by a method according to any one of claims 1, 7, and 8 ≪ / RTI >
10. The method of claim 9,
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.
10. The method of claim 9,
Wherein the organic compound layer containing the compound is a light emitting layer.

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