KR20160090058A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound and an organic light-emitting device comprising the same. The compound is represented by chemical formula 1. According to an embodiment of the present invention, the organic light-emitting device can have the low driving voltage, the high light-emitting efficiency, and/or the long lifespan.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic light-

The present invention relates to a 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.

And to provide an organic light emitting device including the compound of the present application.

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

[Chemical Formula 1]

In formula (1)

X is -O- or -NR-, R is - (L2) _m- Ar2,

L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

n and m are the same as or different from each other, each independently 1 or 2,

When n is 2, the two L1s are the same or different from each other,

when m is 2, two L < 2 > s are the same or different from each other,

Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; An ester group; A carbonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p and s are integers of from 0 to 4,

q and r are integers of 0 to 2,

When p, q, r, and s are each an integer of 2 or more, a plurality of R1, R2, R3, and R4 are the same or different from each other.

The present application also 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 described above.

An organic light emitting device using a compound according to one embodiment of the present application is capable of low driving voltage, high luminous efficiency and / or long life.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated.
2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated FIG.

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

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

According to one embodiment of the present application, the compound represented by Formula 1 has a core structure as described above, and thus has an advantage of being able to control triplet energy and exhibits long life and high efficiency characteristics.

Examples of substituents herein are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, the "substituent group to which two or more 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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

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. 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

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

,

,

And

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

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group 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, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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, the adjacent groups bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above , Monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

According to one embodiment of the present application, the compound represented by the formula (1) is represented by any one of the following formulas (2) to (7).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,

X, L 1, n, Ar 1, R 1 to R 4, p, q, r and s are as defined in formula (1).

According to one embodiment of the present application, the compound represented by Formula 1 is represented by any one of Formulas 2 to 5.

According to one embodiment of the present application, the compound represented by the formula (1) is represented by the formula (2).

According to one embodiment of the present application, the compound represented by the formula (1) is represented by the formula (3).

According to one embodiment of the present application, the compound represented by the formula (1) is represented by the formula (4).

According to one embodiment of the present application, the compound represented by the formula (1) is represented by the formula (5).

According to one embodiment of the present application, X is -NR- and R may be - (L2) _m- Ar2.

According to one embodiment of the present application, the formula (1) is represented by any one of the following formulas (2-1) to (5-1).

[Formula 2-1]

[Formula 3-1]

[Formula 4-1]

[Formula 5-1]

In the formulas (2-1) to (5-1)

R1, R2, R3, R4, p, q, r and s are the same as defined in formula (1).

According to one embodiment of the present application, X may be -O-.

According to one embodiment of the present application, the formula (1) is represented by any one of the following formulas (2-2) to (5-2).

[Formula 2-2]

[Formula 3-2]

[Formula 4-2]

[Formula 5-2]

In the above Formulas (2-2) to (5-2)

L1, n, Ar1, R1 to R4, p, q, r and s are as defined in formula (1).

In one embodiment of the present application, L 1 and L 2 are the same or different and are each independently a direct bond; A substituted or unsubstituted monocyclic or bicyclic arylene group; Or a substituted or unsubstituted monocyclic or bicyclic divalent heterocyclic group.

According to one embodiment of the present application, the monocyclic or bicyclic bivalent heterocyclic group may contain N as a hetero atom.

According to one embodiment of the present application, L1 and L2 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted monocyclic or bicyclic N-containing bivalent heterocyclic group.

And L < 2 > are the same or different and are each independently a direct bond; Or represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above Formulas A and B, Y1 to Y7 are N or CR 'and R' is hydrogen; heavy hydrogen; A substituted or unsubstituted C ₁ to C ₄₀ alkyl group; A substituted or unsubstituted C ₆ to C ₄₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heterocyclic group.

According to one embodiment of the present application, Y1 is N.

According to one embodiment of the present application, Y2 is N.

According to one embodiment of the present application, Y1 and Y2 are N.

According to one embodiment of the present application, Y1 and Y3 are N.

According to one embodiment of the present application, Y2 and Y3 are N.

According to one embodiment of the present application, Y4 is N.

According to one embodiment of the present application, Y4 and Y5 are N.

According to one embodiment of the present application, Y4 and Y6 are N.

According to one embodiment of the present application, Y5 and Y7 are N.

According to one embodiment of the present application, Y4, Y6 and Y7 are N.

According to one embodiment of the present application, R 'is hydrogen; heavy hydrogen; methyl; Phenyl; Or biphenyl.

According to one embodiment of the present application, R 'is hydrogen.

According to one embodiment of the present application, X is NR, R is - (L2) _m -Ar2, and at least one of L1 and L2 may be a group represented by the above formula (A).

According to one embodiment of the present application, in Formula 1, X is O, and L 1 may be a group represented by Formula B.

According to one embodiment of the present application, L1 and L2 are the same or different and are each independently a direct bond; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidylene group; A substituted or unsubstituted pyridazinyl group; A substituted or unsubstituted pyrazylene group; A substituted or unsubstituted thiazylene group; A substituted or unsubstituted quinolinylene group; A substituted or unsubstituted isoquinolinylene group; A substituted or unsubstituted quinazolinylene group; Or a substituted or unsubstituted quinoxalinylene group.

According to one embodiment of the present application, L1 and L2 are the same or different and are each independently a direct bond; A substituted or unsubstituted thiazylene group; Substituted or unsubstituted quinazolinylene group.

According to one embodiment of the present application, Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group.

According to one embodiment of the present application, Ar 1 and Ar 2 are the same or different and are a substituted or unsubstituted C ₆ to C ₂₀ aryl group.

According to an exemplary embodiment of the present application, wherein Ar1 and Ar2 are the same or different from each other, and each independently C ₆ to C ₂₀ aryl group and a C ₂ to a heterocyclic group with at least one substituted or unsubstituted selected from the group consisting of C ₂₀ C ₆ to C ₂₀ aryl groups; Or C ₆ to C ₂₀ is a heterocyclic group of the aryl group and the C ₂ to C ₂₀ heterocyclic group is selected from substituted or unsubstituted with at least one C ₂ to C ₂₀ a.

According to one embodiment of the present application, Ar 1 and Ar 2 are the same or different and are C ₆ to C ₂₀ substituted or unsubstituted C ₆ to C ₂₀ heterocyclic groups selected from an aryl group and a C ₂ to C ₂₀ heterocyclic group, To C < ₂₀ >

According to one embodiment of the present application, Ar1 and Ar2 are the same or different and are each independently substituted or unsubstituted phenyl; Substituted or unsubstituted biphenyl; Or substituted or unsubstituted naphthyl.

According to one embodiment of the present application, the - (L 1) _n -Ar 1 and - (L 2) _m -Ar 2 are the same or different and are each independently a substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted thiazinyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted isoquinolinyl group; A substituted or unsubstituted quinazolinyl group; Or a substituted or unsubstituted quinoxalinyl group.

According to one embodiment of the present application, the - (L 1) _n -Ar 1 and - (L 2) _m -Ar 2 are the same or different and are each independently substituted or at least substituted with at least one selected from phenyl, biphenyl and naphthyl A substituted pyridyl group; A pyrimidyl group substituted or unsubstituted with at least one selected from phenyl, biphenyl and naphthyl; A triazinyl group substituted or unsubstituted with at least one member selected from phenyl, biphenyl and naphthyl; A quinolinyl group substituted or unsubstituted with at least one selected from phenyl, biphenyl and naphthyl; An isoquinolinyl group substituted or unsubstituted with at least one selected from phenyl, biphenyl and naphthyl; A quinazolinyl group substituted or unsubstituted with at least one selected from phenyl, biphenyl and naphthyl; Or a quinoxalinyl group substituted or unsubstituted with at least one selected from phenyl, biphenyl and naphthyl.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₁ to C ₂₀ alkyl group; A substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₁ to C ₂₀ alkyl group; Or a substituted or unsubstituted C ₆ to C ₂₀ aryl group.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; methyl; Phenyl; Biphenyl; Or naphthyl.

According to one embodiment of the present application, R1 is hydrogen, deuterium, methyl or phenyl.

According to one embodiment of the present application, R2 is hydrogen, deuterium, methyl or phenyl.

According to one embodiment of the present application, R3 is hydrogen, deuterium, methyl or phenyl.

According to one embodiment of the present application, R4 is hydrogen, deuterium, methyl or phenyl.

According to one embodiment of the present application, R1 to R4 are hydrogen.

According to one embodiment of the present application, the compound represented by Formula 1 is represented by any one of the following structural formulas.

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

In one embodiment of the present disclosure, the 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.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

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.

In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In one embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present application, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

In one embodiment of the present application, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the above compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In the embodiment of the present application, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

In one embodiment of the present invention, the organic layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group, in addition to the organic compound layer containing the compound.

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

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

1 shows a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated Structure is illustrated. In such a structure, the compound may be contained in at least one of the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, and the electron transporting layer 7.

In such a structure, the compound 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 of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound.

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 one or more of the organic layers include the compound, i.e., the compound represented by the above 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.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, 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 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 heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, 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 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, perylene tetracarboxylic 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 hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (15)

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

In formula (1)
X is -O- or -NR-, R is - (L2) _m- Ar2,
L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
n and m are the same as or different from each other, each independently 1 or 2,
When n is 2, the two L1s are the same or different from each other,
when m is 2, two L < 2 > s are the same or different from each other,
Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; An ester group; A carbonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
p and s are integers of from 0 to 4,
q and r are integers of 0 to 2,
When p, q, r, and s are each an integer of 2 or more, a plurality of R1, R2, R3, and R4 are the same or different from each other. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (2) to (7):
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In formulas (2) to (7)
X, L 1, n, Ar 1, R 1 to R 4, p, q, r and s are as defined in formula (1). 2. The compound according to claim 1, wherein X is -NR- and R is - (L2) _m- Ar2. 2. The compound according to claim 1, wherein X is -O-. The method according to claim 1,
L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or bicyclic arylene group; Or a substituted or unsubstituted monocyclic or bicyclic divalent heterocyclic group. 6. The compound according to claim 5, wherein the monocyclic or bicyclic divalent heterocyclic group contains N as a hetero atom. The compound according to claim 1, wherein Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group. The method according to claim 1,
Wherein Ar1 and Ar2 are the same or different from each other, and each independently C ₆ to C ₂₀ aryl group and an aryl group of C ₂ to C ₂₀ selected from the heterocyclic group of at least one substituted or unsubstituted C ₆ to C ₂₀ of ; Or C ₆ to C ₂₀ aryl group and C ₂ to the heterocyclic group to a compound of C ₂₀ is selected from a heterocyclic group substituted or unsubstituted with at least one C ₂ to C ₂₀ of the. The method of claim 1,
R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₁ to C ₂₀ alkyl group; A substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by any one of 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 compound layers comprises the compound according to any one of claims 1 to 10. The organic light- Light emitting element. The method of claim 11,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound. The method of claim 11,
Wherein the organic material layer includes a hole injection layer or a hole transport layer,
Wherein the hole injection layer or the hole transport layer comprises the compound. The method of claim 11,
Wherein the organic material layer includes an electron transport layer or an electron injection layer,
Wherein the electron transport layer or the electron injection layer comprises the compound. The method of claim 11,
The organic light emitting device includes a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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