KR101951378B1 - Amine-based compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides an amine compound and an organic light emitting device comprising the same.

Description

(AMINE-BASED COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME)

TECHNICAL FIELD The present invention relates to an amine-based compound and an organic light-emitting device including the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Publication No. 10-2011-0107681

The present invention provides a compound having excellent brightness and color purity and long life.

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

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

[Chemical Formula 1]

In Formula 1,

R 1 to R 6 are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; And a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

R7 and R8 are each independently selected from the group consisting of hydrogen; heavy hydrogen; And a substituted or unsubstituted aryl group,

Each of a, b, c, d, e and f is independently an integer of 0 to 4;

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 have.

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

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

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

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

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

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

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

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

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

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

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

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

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

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

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

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

In the present specification, examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.

In the present specification, the aryl group 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.

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

,

,

, 및

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

,

,

, And

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

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. 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 benzimidazole group, a benzothiazole group, a benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazyl group And dibenzofuranyl groups, but are not limited thereto.

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

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

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group and the arylamine group can be applied to the description of the aryl group described above.

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

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

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

In the present specification, the description of the aryl group described above can be applied except that arylene 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 term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

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

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

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

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

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

According to one embodiment of the present invention, R 1 to R 6 in Formula 1 may be represented by Formula 2 below.

(2)

In Formula 2, L represents a direct bond; Or a substituted or unsubstituted aryl group.

According to an embodiment of the present invention, L is a direct bond; Or a substituted or unsubstituted monocyclic to tricyclic arylene group.

According to an embodiment of the present invention, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; A substituted or unsubstituted naphthylenyl group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted fluorenylene group; And a substituted or unsubstituted phenanthrenylene group.

According to an embodiment of the present invention, L is a direct bond; A phenylene group; Biphenylene group; A terphenylene group; A quaterphenylene group; A naphthylenyl group; Anthracenylene group; Triphenylene group; Pyrenyl; A fluorenylene group; And a phenanthrenylene group.

According to an embodiment of the present invention, L may be any one selected from the following structures.

The structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylamine group; An aralkylamine group; An arylamine group; And an arylphosphine group, which may be substituted or unsubstituted.

According to one embodiment of the present invention, Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present invention, Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present invention, Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted 1 to 5-membered aralkenyl group; A substituted or unsubstituted 1 to 5-aralkylamine group; A substituted or unsubstituted 1 to 5-membered arylamine group; A substituted or unsubstituted 1 to 5-membered aryl group; A substituted or unsubstituted 1 to 5-membered heteroarylamine group; And a substituted or unsubstituted 1 to 5-membered heterocyclic group.

According to an embodiment of the present invention, Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted 1 to 5-membered heteroarylamine group; And a substituted or unsubstituted 1 to 5-membered heterocyclic group.

According to an embodiment of the present invention, Ar is hydrogen; heavy hydrogen; A phenylene group; Biphenylene group; A terphenylene group; A quaterphenylene group; A naphthylenyl group; Anthracenylene group; A fluorenylene group; Phenanthrenylene group; A substituted or unsubstituted 1 to 5-membered heteroarylamine group; And a substituted or unsubstituted 1 to 5-membered heterocyclic group.

According to one embodiment of the present invention, Ar may be any one selected from the following structures.

Further, according to one embodiment of the present invention, R 2 and R 5 are a substituted or unsubstituted aryl group or a substituted or unsubstituted amine group.

According to an embodiment of the present invention, each of R7 and R8 in Formula 1 is independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R7 and R8 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted 1 to 4-membered aryl group; Or a substituted or unsubstituted 1 to 4 heteroaryl group.

According to one embodiment of the present invention, when R7 or R8 is an aryl group, the aryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, and a substituted or unsubstituted chrysenyl group .

According to one embodiment of the present invention, when R7 and R8 are aryl groups, the aryl group may be substituted with at least one of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, And a triphenylene group.

According to one embodiment of the present invention, when R7 and R8 are a heteroaryl group, the heteroaryl group may be substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted benzocarbazole group.

According to one embodiment of the present disclosure, when R7 and R8 are a heteroaryl group, the heteroaryl group may be a dibenzothiophene group; A dibenzofuranyl group; Carbazole group; And a benzocarbazole group.

According to one embodiment of the present invention, the compound of Formula 1 may be any one selected from the following formulas.

According to one embodiment of the present disclosure, there is provided 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 the compound of Formula 1 have.

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 injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, an electron blocking layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

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

According to an embodiment of the present invention, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound of the formula (1).

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

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

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

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

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

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

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

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

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

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

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

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

The anode material may be a material having a large work function such that holes can be normally injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

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

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

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

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

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

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

PREPARATION EXAMPLE 1 Synthesis of A1 to A2

 [Synthesis of A1]

(20 g, 61.68 mmol) was dissolved in THF (250 ml), the temperature was lowered to -78 ° C, 2.5 M n-BuLi (34.5 ml) was added dropwise, and after 30 minutes, 2- Bromoanthracene-9,10-dione (17.7 g, 61.68 mmol) was added thereto, and the mixture was stirred at RT for 1 hour. Add 1N HCl (300 ml) and filter. Washed with ethyl acetate, and then recrystallized from chloroform and ethyl acetate

The obtained solid was dissolved in acetic acid (250 ml), 2 ml of sulfuric acid was added dropwise, and the mixture was refluxed with stirring. The temperature was lowered to room temperature and neutralized with water. The filtered solid was recrystallized from ethyl acetate to give Compound A1 (38.9 g, 85%).

MS [M + H] < ⁺ > = 742.73

[Synthesis of A2]

Compound A2 was synthesized in the same manner as in the synthesis of A1 except that 2,6-dibromoanthracene-9,10-dione was used instead of 2-bromoanthracene-9,10-dione

MS [M + H] < ⁺ > = 821.63

PREPARATION EXAMPLE 2 Preparation of Compound 1 to 8

[Synthesis of compound 1]

(3.5 g, 20.82 mmol) and sodium-t-butoxide (2.73 g, 28.32 mmol) were added to xylene and the mixture was heated under stirring, refluxed, and [bis (triphenylphosphine) -Butylphosphine)] palladium (206 mg, 2 mmol%). After the temperature was lowered to room temperature and the reaction was terminated, compound 1 was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] < ⁺ > = 831.05

[Synthesis of Compound 2]

Compound 1 was synthesized in the same manner as Compound 1 except that N-phenyl- (1,1'-biphenyl) -4-amine was used instead of diphenylamine to prepare Compound 2

MS [M + H] < ⁺ > = 907.15

[Synthesis of Compound 3]

Compound 3 was prepared by the same method except for using 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of diphenylamine in the synthesis of Compound 1

MS [M + H] < ⁺ > = 947.21

[Synthesis of Compound 4]

Compound 4 was prepared by the same method except for using N-phenylnaphthalen-1 -amine instead of diphenylamine in the synthesis of Compound 1

MS [M + H] < ⁺ > = 881.11

[Synthesis of compound 5]

Compound 5 was prepared by the same method except that N-phenylnaphthalene-2-amine was used instead of diphenylamine in the synthesis of Compound 1

MS [M + H] < ⁺ > = 881.11

[Synthesis of Compound 6]

Compound 6 was prepared by the same method as Compound 1 except that N-phenyldibenzo [b, d] furan-4-amine was used instead of diphenylamine

MS [M + H] < ⁺ > = 921.13

[Synthesis of Compound 7]

Dibenzo [b, d] furan-1-amine was used in place of N-phenyldibenzo [b, d] furan-4-amine in the synthesis of Compound 7, 8 was prepared

MS [M + H] < ⁺ > = 1178.42

< Example  1>

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

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. Compound 3 (900 Å) synthesized in the above Production Example 2, which is a hole transport material, was vacuum deposited on the hole transport layer, and then HT2 was vacuum deposited on the hole transport layer to a film thickness of 100 Å to form a hole control layer. A host H1 and a dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 Å as a compound light emitting layer. Then, an E1 compound (300 ANGSTROM) was sequentially vacuum-deposited by electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

[Hexanitrile hexaazatriphenylgylene] [HT1]

      [H1] [HT2]

   [E1] [D1]

< Example  2>

The same experiment was conducted as in Example 1 except that Compound 4 was used instead of Compound 3 synthesized in Production Example 2 as the hole transport layer.

< Example  3>

The same experiment was conducted as in Example 1 except that Compound 5 was used instead of Compound 3 synthesized in Preparation Example 2 as a hole transport layer.

< Example  4>

The same experiment was conducted as in Example 1 except that Compound 6 was used instead of Compound 3 synthesized in Production Example 2 as a hole transport layer.

< Comparative Example  1>

In the same manner as Example 1 except that HT1 was used instead of Compound 1 synthesized in Production Example 3 as a hole transport layer.

Table 1 shows the results of the organic light emitting device manufactured by using each compound as a hole transporting layer material as in Examples 1 to 4 and Comparative Example 1.

Experimental Example
50 mA / cm 2 Hole transport layer Voltage (V) Current efficiency (cd / A) Comparative Example 1 HT1 4.12 5.35 Example 1 Compound 3 3.67 5.70 Example 2 Compound 4 3.56 5.75 Example 3 Compound 5 3.59 5.88 Example 4 Compound 6 3.66 5.56

The compounds used in Examples 1 to 4, as shown in Table 1,

It was used as a hole transporting layer in the present invention, and exhibits characteristics of low voltage and high efficiency as compared with Comparative Example 1 which is a benzidine type material.

< Example  5>

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the ITO transparent electrode prepared in the same manner as in Example 1 to a thickness of 500 Å to form a hole injection layer. HT1 (900 Å), which is a material for transporting holes, was vacuum deposited on the hole transport layer, followed by vacuum deposition on the hole transport layer at a film thickness of 100 Å of the compound 1 synthesized in Preparation Example 2 to form a hole control layer. A host H1 and a dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 Å as a compound light emitting layer. Then, an E1 compound (300 ANGSTROM) was sequentially vacuum-deposited by electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

< Example  6>

The same experiment was conducted as in Example 5 except that Compound 2 was used instead of Compound 1 synthesized in Production Example 2 as the hole control layer.

< Comparative Example  2>

The same experiment was conducted as in Example 5 except that HT2 was used instead of Compound 1 synthesized in Preparation Example 2 as the hole control layer.

Table 2 shows the results of experiments of the organic light emitting devices manufactured using the respective compounds as the hole transporting layer materials as in Examples 5 to 6 and Comparative Example 2.

Experimental Example
50 mA / cm 2 The hole- Voltage (V) Current efficiency (cd / A) Comparative Example 2 HT2 4.02 5.11 Example 5 Compound 1 3.78 5.45 Example 6 Compound 2 3.77 5..55

As shown in Table 2, the compounds used in Examples 5 to 6 were used as the hole-controlling layer in the organic light-emitting device, and exhibited lower voltage and higher efficiency than the carbazole type HT2 used in Comparative Example 2. [

The spiro-structured material of this patent has a relatively higher triplet energy and thus shows a tendency to improve the device performance and also acts as a hole-regulating layer.

The compound represented by the chemical formula according to the present invention can function as a hole transporting and hole controlling in an organic electronic device including an organic light emitting device, and the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and stability.

< Example  7>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Subsequently, the following compound N - ([1,1'-bisphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4 benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (100A)

[EB1]

Subsequently, the following BH and compound 7 were vacuum deposited on the hole-adjusting layer at a weight ratio of 25: 1 at a thickness of 300 ANGSTROM to form a light emitting layer.

[BH]

 [ET1]

[LiQ]

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

< Example 8 >

The same experiment was conducted as in Example 7 except that Compound 8 was used instead of Compound 7 synthesized in Preparation Example 2.

< Comparative Example 3 >

[BD]

The same experiment was conducted except that BD was used instead of the compound 7 synthesized in Preparation Example 2 in Example 7.

Table 3 shows the results of the organic light emitting device manufactured using the respective compounds as dopant materials as in Examples 7 to 8 and Comparative Example 3. [

Experimental Example
50 mA / cm 2 Dopant Voltage (V) Current efficiency (cd / A) Comparative Example 3 BD 4.02 5.11 Example 7 Compound 7 4.05 5.12 Example 8 Compound 8 4.08 5.15

As shown in Table 3, the compounds used in Examples 7 to 8 were used as dopants in an organic light emitting device and exhibited characteristics equal to or higher than those of pyrene type BD used in Comparative Example 3. [

The compound represented by the chemical formula according to the present invention can also serve as a dopant in an organic electronic device including an organic light emitting device. The device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

Claims (10)

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

In Formula 1,
R ₂ and R ₅ is represented by the following general formula (2), and the other is hydrogen, deuterium or a group represented by the following general formula (2)
R ₁ , R ₃ , R ₄ and R ₆ are hydrogen or deuterium,
R ₇ and R ₈ are each independently an aryl group,
a, b, c, d, e and f are each independently an integer of 0 to 4,
(2)

In Formula 2,
L is a direct bond,
Ar represents an arylamine group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroarylamine group substituted or unsubstituted with an aryl group. delete delete 2. The compound according to claim 1, wherein Ar is any one selected from the following structures:

. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following structural formulas:

. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode,
Wherein at least one of the organic layers includes a compound according to any one of claims 1, 4, and 5. The organic light emitting diode according to claim 6, wherein the organic material layer is a hole injection layer or a hole transport layer. 7. The organic light emitting device according to claim 6, wherein the organic material layer is an electron suppressing layer. The organic light emitting device according to claim 6, wherein the organic material layer is a layer simultaneously injecting holes and transporting holes. The organic light emitting device according to claim 6, wherein the organic material layer is a light emitting layer.