KR20150004099A - An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescence device including a light efficiency enhancing layer and an electronic device thereof. The organic electroluminescence device according to an embodiment of the present invention includes: a first electrode; a second electrode; one or more organic compound layers formed between the first and second electrodes; and a light efficiency enhancing layer which is formed on the one side of the first or second electrode facing the organic compound layer. The organic electroluminescence device can enhance the luminous efficiency and be used for an extended period of time.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an organic electroluminescent device including an optical efficiency improving layer and an electronic device including the same.

The present invention relates to an organic electronic device including a light-efficiency-improvement layer and an electronic 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 electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In organic electroluminescent devices, the most problematic is the lifetime and the efficiency. As the display becomes larger, such efficiency and life time problems must be solved. The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase.

However, it is impossible to maximize the efficiency by merely improving the organic material layer. The energy level and T1 value of each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) It can achieve long life and high efficiency at the same time. Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently. That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Particularly, development of materials for a light emitting layer is urgently required.

On the other hand, the diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, is delayed, and stable characteristics such as joule heating generated during driving the device, It is necessary to develop a hole injection layer material having a temperature. It is also reported that the low glass transition temperature of the hole transporting layer material significantly affects the lifetime of the device depending on the characteristics of the uniformity of the thin film surface collapsing during device operation. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a long time, that is, a material having high heat resistance characteristics, is required.

In recent years, not only research to improve the device characteristics by changing the performance of each material, but also to improve the color purity by the optical thickness optimized between the anode and the cathode in the top element of the resonance structure, It is one of the important factors to improve. Compared with the bottom element structure of the non-resonance structure, the top element structure has a large optical energy loss due to SPP (surface plasmon polariton) because the formed light is reflected by the anode which is a reflection film and emits light toward the cathode.

Therefore, one of the important methods for enhancing the shape and efficiency of the EL Spectral is to use a light efficiency improvement layer in a p-cathode. In general, the electron emission of SPP is mainly composed of four metals such as Al, Pt, Ag and Au, and surface plasmon is generated on the surface of the metal electrode. For example, when the cathode is made of Ag, the light emitted by the Ag of the cathode is quenching (loss of light energy due to Ag) by the SPP, and the efficiency is reduced.

On the other hand, when the light-efficiency-enhancement layer is used, SPP is generated at the interface between the MgAg electrode and the high-refractive-index organic material, and the TE polarized light is extinguished in the vertical direction by the evanescent wave, The transverse magnetic (TM) polarized light moving along the cathode and the light efficiency improvement layer is amplified by surface plasma resonance, thereby increasing the intensity of the peak, Efficiency and effective color purity control becomes possible.

It is an object of the present invention to provide an organic electronic device including an optical efficiency improving layer having a high refractive index capable of improving the device's high luminous efficiency, low driving voltage, color purity, and service life, and an electronic device including the same.

In one aspect, the present invention provides an organic electroluminescent device including a compound represented by the following formula in a light-efficiency-improvement layer and an electronic device therefor.

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

1 and 2 are schematic block diagrams of an organic electroluminescent device according to an embodiment of the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference numerals whenever possible, even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

The term " halo "or" halogen ", as used herein, unless otherwise indicated, is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group "," alkoxy group ", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, the arylalkyl group is an alkyl group substituted with an aryl group, the arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the present specification.

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. For example, the arylalkoxy group means an alkoxy group substituted with an aryl group, the alkoxycarbonyl group means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, an alkenyl group substituted with an arylcarbonyl group means Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings and includes a heteroaliphatic ring and hetero Aromatic rings. Adjacent functional groups may be combined and formed.

As used herein, the term "heteroatom " refers to N, O, S, P or Si unless otherwise stated.

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms and an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise indicated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or hetero ring having 6 to 60 carbon atoms.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group of 1-20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, a substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring. When a is an integer of 2 or 3, Wherein R ¹ may be the same or different and is bonded to the carbon of the benzene ring in a similar manner when a is an integer from 4 to 6 and the indication of hydrogen bonded to the carbon forming the benzene ring is omitted do.

1 and 2 are views illustrating an organic electroluminescent device according to an embodiment of the present invention.

1 and 2, an organic electroluminescent device according to the present invention includes first electrodes 102 and 202 formed on substrates 101 and 201, an organic material layer, second electrodes 108 and 208, and a light- The light efficiency improvement layers 109 and 209 may be formed on the first electrode lower part (BOTTOM EMISSION method) and / or the second electrode upper part (TOP EMISSION method).

In the case of the top emission type, light emitted from the light emitting layer is emitted toward the cathode. The light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed of an organic material having a relatively high refractive index, do.

Even in the case of the bottom emission method, the light efficiency of the organic electroluminescent device is improved by interposing the light-efficiency-improvement layer according to the present invention by the same principle.

Of course, the light-efficiency-improvement layer can not be formed only at such a position. In FIGS. 1 and 2, the light efficiency improvement layer is formed on both the second electrode and the first electrode. However, in FIG. 1, the light efficiency improvement layer may be formed not only on the second electrode but also on the first electrode.

1 and 2 illustrate examples of the organic material layer in which the hole injection layers 103 and 203, the hole transporting layers 104 and 204, the light emitting layers 105 and 205, the electron transporting layers 106 and 206, , 207, but at least one of these layers may be omitted.

Although not shown, the organic electroluminescent device includes a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for blocking the movement of electrons, a light emitting auxiliary layer for assisting or assisting light emission, May be located further. In the case of the protective layer, it may be formed to protect the organic layer at the uppermost layer or to protect the cathode.

In addition, the compound of the present invention may be contained in at least one of the light-efficiency-improvement layer as well as the organic material layer including the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic electroluminescent device according to another embodiment of the present invention may be formed by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, An anode is formed by depositing an alloy thereof, an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon . At this time, the light-efficiency-improvement layer according to the present invention may be formed on the lower portion of the anode or on the upper portion of the cathode.

In addition to such a method, the organic material may be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, but is not limited thereto and may have a single layer structure.

In addition, the organic layer and the light-efficiency-improvement layer may be formed by using a variety of polymer materials, not a vapor deposition method, a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, It is possible to fabricate a smaller number of layers by a process, a doctor blading process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

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

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, an organic electroluminescent device according to one aspect of the present invention is provided.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; At least one organic layer formed between the first electrode and the second electrode; And a light-efficiency-improvement layer formed on at least one side of the one side of the first electrode and the second electrode opposite to the organic layer, wherein the light-efficiency-improvement layer comprises a compound represented by the formula (1) And an organic electroluminescent device.

(1)

In the above formula (1)

m is an integer of 0 to 4,

n is an integer of 0 to 3,

L ¹ is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A _divalent heterocyclic group of C ₂ to C ₆₀ containing at least one hetero atom selected from O, N, S, Si and P or SO ₂ ; A fluorenylene group; O, N, S, Si and P of the at least one heteroatom or a divalent SO ₂ C ₂ ~ C ₆₀ heterocyclic group and C ₆ ~ C ₆₀ aryl group is a divalent functional group comprising a combination of; And two of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring group; is selected from the group consisting of,

R ¹ and R ² are the same or different from each other when m and n are two or more, and i) independently of one another, deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ² -N (R ^a ) (R ^b ), wherein L ² is a single bond, a C ₆ to C ₆₀ arylene group, a fluorenedylene group, a C ₃ to C ₆₀ 2 is a fused ring group of the aromatic ring of an aliphatic ring and C ₆ ~ C _60; a; and O, N, S, Si and P, at least one heteroatom divalent C ₂ ~ C ₆₀ heterocyclic ring containing a group And R ^a and R ^b are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group, a fluorenyl group, a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring group And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, or ii) a plurality of R ¹ groups or a plurality of R ² Groups are taken together to form an aromatic ring with the carbon to which they are attached, wherein the group not forming a ring is as defined in i)

Ar ¹ to Ar ³ independently represent a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And ^{-L 3 -N (R c) (} R d); selected from the group consisting of: or (wherein L ^3, R ^c and R ^d are as defined in the above L ^2, R ^a and R ^b, respectively), Or ii) Ar < ^{2 >} and Ar < ³ > are bonded to each other to form a ring together with N to which they are bonded,

The aryl group may be substituted with at least one substituent selected from the group consisting of an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, , a germanium group, a cyano group, a nitro ^{group, -L 4 -N (R e)} (R f) ( wherein L as defined in ^4, R ^e and R ^f are the L ^2, R ^a and R ^b, respectively) , C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C of ₂₀ of the aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, fluorene group, O, N, S, a heterocyclic of Si and C ₂ ~ containing at least one hetero atom in the P C ₂₀ group, from the group consisting of aryl alkenyl group of C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ aryl group and a C ₈ ~ C ₂₀ of the with one or more substituents selected can be further substituted.

In another embodiment of the present invention, L ¹ in the above formula (1) is ^one of the following formulas.

In the above formulas,

X ¹ is C (R ³ ) or N,

X ² is C (R ⁴ ) (R ⁵ ), N (R ⁶ ), S, SO ₂ or O,

R ³ , Ar ⁴ And Ar < ⁵ > are, independently of each other, hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxy group; And a fluorenyl group;

R ⁴ to R ⁶ are independently selected from: i) a C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxy group; And a fluorenyl group; or ii) R ⁴ and R ⁵ combine with each other to form a spiro compound.

In another embodiment of the present invention, the formula (1) may be one of the following formulas (2) to (13).

In the above formulas (2) to (13)

^{L 1, Ar 1, Ar 2} , Ar 3, R 1, R 2, m and n are each represented by the above formula ^{(1) L 1, Ar 1} , Ar 2, Ar 3, R 1, R 2, m and n Is the same as the definition of

In another embodiment of the present invention, the compound represented by the formula (1) may be one of the following compounds.

In another embodiment of the present invention, the first electrode is an anode formed of ITO containing Ag, the second electrode is a cathode containing Mg-Ag, and the light- And the organic compound layer is formed on one side of the organic compound layer opposite to the organic compound layer.

In another embodiment of the present invention, the second electrode is a light-transmitting cathode electrode, and the light-efficiency-improvement layer is formed on one side of the one side of the second electrode opposite to the organic material layer. Thereby providing an electric element.

In another embodiment of the present invention, the organic layer is patterned for each of R, G, and B pixels, and the light-efficiency-improvement layer is formed as a common layer for the R, G, and B pixels. Device.

In another embodiment of the present invention, the organic compound layer is patterned for each of R, G, and B pixels, and the light efficiency improvement layer is formed in a region corresponding to R pixels with respect to R, G, and B pixels of the organic compound layer And a light efficiency improvement layer (G) formed in a region corresponding to the G pixel and a light efficiency improvement layer (B) formed in an area corresponding to the B pixel, the light efficiency improvement layer And an organic electroluminescent device.

In another embodiment of the present invention, the organic material layer is at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer.

In another embodiment of the present invention, the present invention provides a display device comprising the organic electroluminescent device according to the first aspect of the present invention; And a control unit for driving the display device.

The organic electroluminescent device according to an embodiment of the present invention may be at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Hereinafter, the synthesis examples of the formulas according to the present invention and the production examples of the organic electric devices will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

The final compounds according to the present invention are prepared by reacting Sub 2 or Sub 3 with Sub 1 as shown in Reaction Schemes 1-1 and 1-2.

<Reaction Scheme 1-1>

<Reaction formula 1-2>

One. Sub  Synthesis of 1

Sub 1 of Scheme 1 can be synthesized by the reaction path of Scheme 2 below.

<Reaction Scheme 2>

(Hal ¹ = I or Br; Hal ² = Br or Cl)

Hereinafter, the synthesis of Sub 1 will be described in detail.

(One) Sub  1-11 Synthetic example

<Reaction Scheme 3>

Intermediate Sub  1-I-11 synthesis

The starting material, 3-bromo-9 H -carbazole ( 33.51 g, 136.2 mmol) was dissolved in nitrobenzene to a round bottom flask, iodobenzene (41.67 g, 204.2 mmol ), Na 2 SO 4 (19.34 g, 136.2 mmol), K 2 CO 3 (18.82 g, 136.2 mmol) and Cu (2.6 g, 40.8 mmol) were added and stirred at 200 &lt; 0 &gt; C. When the reaction was complete, nitrobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 32.03 g (yield: 73%) of the product.

Intermediate Sub  One- II -11 synthesis

After the Sub 1-I-11 (32.03 g, 99.4 mmol) obtained in the above synthesis in a round bottom flask was dissolved in DMF, Bis (pinacolato) diboron ( 27.77 g, 109.4 mmol), Pd (dppf) Cl 2 (2.44 g, 3 mmol), KOAc (29.27 g, 298.2 mmol) was added and stirred at 90 &lt; 0 &gt; C. When the reaction was complete, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 30.83 g (yield: 84%) of the product.

Sub  1-11 Synthesis

4-bromo-4'-iodo-1,1'-biphenyl (15.43 g, 43 mmol) was dissolved in THF in a round bottom flask. Sub 1-II-11 (10.58 g, 28.7 mmol) Pd (PPh ₃ ) ₄ (1.66 g, 1.4 mmol), K ₂ CO ₃ (11.88 g, 86 mmol) and water were added and stirred at 80 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 9.65 g of the product (yield: 71%).

(2) Sub  1-17 Synthetic example

<Reaction Scheme 4>

Intermediate Sub  1-I-17 synthesis

2-iodonaphthalene (19.23 g, 75.7 mmol), Na ₂ SO ₄ (50 mL) was added to the starting material, 2-bromo-9 H- (7.17 g, 50.5 mmol), K 2 CO 3 (6.98 g, 50.5 mmol), Cu (0.96 g, 15.1 mmol), and nitrobenzene were obtained using the Sub 1-I-11 synthesis method described above to give 13.15 g (yield: 70%) of the product.

Intermediate Sub  One- II -17 synthesis

Bis (pinacolato) diboron (9.87 g, 38.9 mmol), Pd (dppf) Cl ₂ (0.87 g, 1.1 mmol), KOAc (10.4 g, 106 mmol) and DMF were obtained 11.7 g (Yield: 79%) of the product using the Sub 1-II-11 synthesis method described above.

Sub  1-17 Synthesis

4-bromo-4'-iodo-1,1'-biphenyl (15.03 g, 41.9 mmol) and Pd (PPh ₃ ) ₄ (1.61 g, 27.9 mmol) were added to Sub 1-II- , 1.4 mmol), K ₂ CO ₃ (11.57 g, 83.7 mmol), THF and water were used to obtain 10.68 g (Yield: 73%) of the product using Sub 1-11 synthesis method.

 (3) Sub  1-24 Synthetic example

<Reaction Scheme 5>

Sub  1-24 synthesis

3,7-dibromodibenzo [ b , d ] thiophene (27.87 g, 81.5 mmol) and Pd (PPh ₃ ) ₄ (3.14 g, 2.7 mmol) were added to Sub 1-II-11 (20.06 g, 54.3 mmol) , K ₂ CO ₃ (22.52 g, 163 mmol), THF, and water were used to obtain 18.91 g (yield: 69%) of the product using the Sub 1-11 synthesis method described above.

(4) Sub  1-44 Synthetic example

<Reaction Scheme 6>

Intermediate Sub  1-I-44 synthesis

The starting material, 8-bromo-11 H -benzo [ a] carbazole (27.93 g, 94.3 mmol) in iodobenzene (28.86 g, 141.5 mmol) , Na 2 SO 4 (13.4 g, 94.3 mmol), K 2 CO 3 (13.03 g, 94.3 mmol), Cu (1.8 g, 28.3 mmol) and nitrobenzene were obtained using the Sub 1-I-11 synthesis method as described above to give 25.98 g of the product (yield: 74%).

Intermediate Sub  One- II -44 synthesis

Bis (pinacolato) diboron (19.49 g, 76.8 mmol), Pd (dppf) Cl ₂ (1.71 g, 2.1 mmol) and KOAc (20.55 g, 209.4 mmol) and DMF were obtained 23.41 g (yield: 80%) of the product using the Sub 1-II-11 synthesis method described above.

Sub  1-44 Synthesis

9- H -carbazole (33.59 g, 83.7 mmol), Pd (PPh ₃ ) ₄ (3.23 g, 83.7 mmol) was added to Sub 1-II-44 (23.41 g, 55.8 mmol) 2.98 mmol), K ₂ CO ₃ (23.15 g, 167.5 mmol), THF and water were used to obtain 23.98 g (Yield: 70%) of the product using the Sub 1-11 synthesis method described above.

 (5) Sub  1-57 Synthetic example

<Reaction Scheme 7>

Intermediate Sub  1-I-57 Synthesis

The starting material, 5-bromo-7 H -benzo [ c] carbazole (13.49 g, 45.5 mmol) in iodobenzene (13.94 g, 68.3 mmol) , Na 2 SO 4 (6.47 g, 45.5 mmol), K 2 CO 3 12.21 g (yield: 72%) of the product was obtained by using Sub 1-I-11 synthesis method described above (6.3 g, 45.5 mmol), Cu (0.87 g, 13.7 mmol) and nitrobenzene.

Intermediate Sub  One- II -57 synthesis

Bis (pinacolato) diboron (9.16 g, 36.1 mmol), Pd (dppf) Cl ₂ (0.8 g, 1 mmol), KOAc (9.66 g, 98.4 mmol) and DMF were obtained 10.59 g (Yield: 77%) of the product using the Sub 1-II-11 synthesis method described above.

Sub  1-57 Synthesis

The Sub 1-II-57 (10.59 g, 25.3 mmol) obtained in the above Synthesis 2,7-dibromo-9-phenyl- 9 H -carbazole (15.19 g, 37.9 mmol), Pd (PPh 3) 4 (1.46 g, 1.3 mmol), K ₂ CO ₃ (10.47 g, 75.8 mmol), THF and water were used to obtain 10.54 g (Yield: 68%) of the product using the Sub 1-11 synthetic method.

Examples of Sub 1 include, but are not limited to, the following, and their FD-MSs are shown in Table 1 below.

2. Sub  Synthesis of 2

Sub 2 of Scheme 1 can be synthesized by the reaction path of Scheme 8 below.

<Reaction Scheme 8>

(One) Sub  2-1 Synthetic example

<Reaction Scheme 9>

After the the bromobenzene (10.02 g, 63.8 mmol) starting material is dissolved in toluene in a round bottom flask, aniline (11.89 g, 127.6 mmol ), Pd 2 (dba) 3 (1.75 g, 1.9 mmol), 50% P (t - Bu) ₃ (2.5 ml, 5.1 mmol), NaO t- Bu (18.4 g, 191.5 mmol) was added and stirred at 40 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 8.64 g (yield: 80%) of the product.

(2) Sub  2-5 Synthetic example

<Reaction formula 10>

Aniline (3.74 g, 40.2 mmol), Pd ₂ (dba) ₃ (0.55 g, 0.6 mmol) and 50% P ( t- Bu) ₃ (0.8 ml, 1.6 mmol), NaO t- Bu (5.79 g, 60.3 mmol), and toluene. 3.57 g (Yield: 81%) of the product was obtained using the Sub 2-1 synthesis method described above.

(3) Sub  2-24 Synthetic example

<Reaction Scheme 11>

(6.41 g, 44.8 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.7 mmol) and 50% P ( t- Bu) _{3 were added to the} starting material, 2-bromothiophene (3.65 g, 22.4 mmol) (Yield: 74%) of the product was obtained by using the Sub 2-1 synthesis method described above (0.9 ml, 1.8 mmol), NaO t- Bu (6.45 g, 67.2 mmol) and toluene.

Meanwhile, examples of Sub 2 are as follows but are not limited thereto, and their FD-MS are shown in Table 2 below.

3. Sub  Synthesis of 3

Sub 3 of Scheme 1 can be synthesized by the reaction path of Scheme 12 below.

<Reaction Scheme 12>

(One) Sub  3-1 Synthetic example

<Reaction Scheme 13>

Sub 2-3 (9.47 g, 38.2 mmol) obtained in the above synthesis was dissolved in N , N- dimethylacetamide in a round bottom flask and then Pd (OAc) ₂ (0.26 g, 1.1 mmol) and PCy ₃ .HCF ₄ , 2.3 mmol) and K ₂ CO ₃ (10.55 g, 76.3 mmol) were added and stirred at 130 ° C. When the reaction was complete, N , N- dimethylacetamide was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 5.68 g (yield: 89%) of the product.

Meanwhile, examples of Sub 3 are as follows, but the present invention is not limited thereto, and their FD-MSs are shown in Table 3 below.

4. Final product ( Final Products ) Synthesis of

Sub 1 (1.1 eq.), Pd ₂ (dba) ₃ (0.03 eq.), P (t-Bu) ₃ (0.08 eq.), NaO t- Bu (3 eq) was added and stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain final products.

(1) P-9 Synthetic example

<Reaction Scheme 14>

Sub 1-12 (7.67 g, 16.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) were dissolved in toluene in a round bottom flask with Sub 2-24 (3.31 g, , 50% P ( t- Bu) ₃ (0.6 ml, 1.2 mmol) and NaO t- Bu (4.24 g, 44.1 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The concentrated product was purified by silicagel column and recrystallized to obtain 6.82 g (yield: 75%) of the product.

(2) P-13 Synthetic example

<Reaction Scheme 15>

Sub 2-24 (8.46 g, 16.8 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.5 mmol) and 50% P ( t- Bu) were added to Sub 2-1 (2.58 g, 15.2 mmol) ₃ (0.6 ml, 1.2 mmol), NaO t- Bu (4.4 g, 45.7 mmol) and toluene were used to obtain 7.14 g of the product (yield: 79%).

(3) P-35 Synthetic example

<Reaction Scheme 16>

Sub-1-17 (7.23 g, 13.8 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.4 mmol) and 50% P ( t- Bu) were added to Sub 2-1 (2.12 g, ₃ (0.5 ml, 1 mmol), NaO t- Bu (3.61 g, 37.6 mmol) and toluene were obtained 6.37 g (yield: 83%) of the product using the above P-9 synthesis method.

(4) P-49 Synthetic example

<Reaction Scheme 17>

Sub-44 (9.33 g, 15.2 mmol), Pd ₂ (dba) ₃ (0.38 g, 0.4 mmol) and 50% P ( t- Bu) were added to Sub 2-1 (2.34 g, ₃ (0.5 ml, 1.1 mmol), NaO t- Bu (3.99 g, 41.5 mmol) and toluene were obtained 7.76 g (Yield: 80%) of the product using the above P-9 synthesis method.

(5) P-57 Synthetic example

<Reaction Scheme 18>

Sub-1-57 (8.89 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.36 g, 0.4 mmol) and 50% P ( t- Bu) were added to Sub 2-5 (2.89 g, 13.2 mmol) ₃ (0.5 ml, 1.1 mmol), NaO t- Bu (3.8 g, 39.5 mmol) and toluene were used to obtain 7.63 g (Yield: 77%) of the product using the above P-9 synthesis method.

(6) P-63 Synthetic example

<Reaction Scheme 18>

Sub 2-24 (8.36 g, 16.6 mmol), Pd ₂ (dba) ₃ (0.41 g, 0.5 mmol) and 50% P ( t- Bu) were added to Sub 3-1 (2.52 g, 15.1 mmol) ₃ (0.6 ml, 1.2 mmol), NaO t- Bu (4.35 g, 45.2 mmol) and toluene were obtained 6.32 g (Yield: 71%) of the product using the above P-9 synthesis method.

(7) P-66 Synthetic example

<Reaction Scheme 19>

Sub-44 (10.37 g, 16.9 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.5 mmol) and 50% P ( t- Bu) were added to Sub 3-1 (2.57 g, 15.4 mmol) ₃ (0.6 ml, 1.2 mmol), NaO t- Bu (4.43 g, 46.1 mmol) and toluene were obtained 7.31 g (yield: 68%) of the product using the above P-9 synthesis method.

Meanwhile, the FD-MS values of the compounds P-1 to P-80 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

On the other hand, the above has been described in an illustrative synthesis of the present invention represented by the general formula (1), all of which Ullmann reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Direct intramolecular arylation reaction (J. Am. Chem. Soc. , 2006 , 128 , 581), and Buchwald-Hartwig cross coupling reaction. Even if other substituents (R ₁ , R ₂ , L ₁ , Ar ₁ to Ar ₃ ) defined in Chemical Formula 1 are bonded in addition to the substituent It will be readily understood by those skilled in the art. For example, in Scheme 2, the starting material -> Sub 1-I reaction is based on the Ullmann reaction, and the Sub 1-I -> Sub 1-II reaction in Scheme 2 is based on the Miyaura boration reaction, -> Sub 1 reaction is based on Suzuki cross-coupling reaction. Sub 2 -> Sub 3 reactions in Scheme 12 are based on Direct intramolecular arylation reactions and starting materials -> Sub 2 reactions and Product synthesis reactions (Scheme 14 to Scheme 19) in Scheme 8 are based on the Buchwald-Hartwig cross coupling reaction , And the reactions will proceed even if substituents not specifically mentioned therein are bonded.

Evaluation of manufacturing of organic electric device

A capping layer formed on a Mg: Ag second electrode (cathode) of a device including a pair of electrodes of a first electrode (anode) and a second electrode (cathode) includes the compound of the present invention A production example of an organic electroluminescent device is described.

[ Experimental Example  I] Red organic electroluminescent device

An ITO substrate containing Ag was prepared on a 10 mm x 10 mm x 1 mm glass substrate and 4,4 ', 4''- Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) ) Was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Then, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Next, CBP (4,4'- N, N'-dicarbazole-biphenyl) was used as a host material on the hole transport layer and (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium ) acetylacetonate] was doped at a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) as an electron transporting compound was vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transporting layer. Subsequently, LiF as a halogenated alkali metal was deposited to a thickness of 0.2 nm to form an electron injecting layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Then, the compound of the present invention (P-1 to P- 80) was deposited to a thickness of 60 nm to form a light-efficiency improvement layer (capping layer), thereby preparing an organic electroluminescent device.

[ Comparative Example  One]

An organic electroluminescence device was fabricated in the same manner as in [Experiment I], except that a capping layer was not used.

[ Comparative Example  2]

An organic EL device was prepared in the same manner as in [Experimental Example I] except that Alq ₃ was used instead of the compound of the present invention as a light-emitting efficiency improving layer material.

Comparative Example 1 and Comparative Example 2, which were prepared in this manner, were prepared by applying a forward bias DC voltage to the organic electroluminescent device and measuring the PR- 650, and the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a reference luminance of 2500 cd / m ² .

Table 5 shows the device fabrication and evaluation results for [Experimental Example I] (Experimental Examples (1) to (72)) and Comparative Example 1 and Comparative Example 2 to which the compound according to the present invention was applied.

[ Experimental Example II ] Green organic electroluminescent device

2-TNATA was vacuum-deposited thereon to form a hole injection layer having a thickness of 60 nm on the glass substrate having a size of 10 mm x 10 mm x 1 mm. Then, a hole injection layer was formed on the hole injection layer using NPD Was vacuum-deposited to a thickness of 60 nm to form a hole transporting layer. Next, the CBP [4,4'- N, N '-dicarbazole -biphenyl] as a host material on the hole transport _{layer, Ir (ppy) 3 [tris} (2-phenylpyridine) -iridium] as a dopant material 90: 10 And the light emitting layer was deposited to a thickness of 30 nm by doping. Followed by forming the electron transporting layer was vacuum-deposited Alq ₃ in 40 nm thick as an electron transport material forming the hole blocking layer by vacuum depositing BAlq on the light emitting layer 10 nm in thickness, and on the hole blocking layer. Subsequently, LiF as a halogenated alkali metal was deposited to a thickness of 0.2 nm to form an electron injecting layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Then, the compound of the present invention (P-1 to P- 80) was deposited to a thickness of 60 nm to form a light-efficiency improvement layer (capping layer), thereby preparing an organic electroluminescent device.

[ Comparative Example  3]

An organic electroluminescent device was fabricated in the same manner as in [Experimental Example II], except that a capping layer was not used.

[ Comparative Example  4]

An organic EL device was prepared in the same manner as in [Experimental Example II], except that Alq ₃ was used instead of the compound of the present invention as a light-emitting efficiency improving layer material.

Comparative Example 3 and Comparative Example 4 were prepared in the same manner as in Experimental Example II (Experimental Example 73 to Experimental Example 115), Comparative Example 3 and Comparative Example 4, except that a forward bias DC voltage was applied to the organic electroluminescent device, 650, and the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 5000 cd / m ² .

Table 6 below shows device fabrication and evaluation results for [Experimental Example II] (Experimental Examples (73) to (115)), Comparative Example 3 and Comparative Example 4 to which the compound according to the present invention was applied.

[ Experimental Example III ] Blue organic electroluminescent device

2-TNATA was vacuum-deposited thereon to form a hole injection layer having a thickness of 60 nm on the glass substrate having a size of 10 mm x 10 mm x 1 mm. Then, a hole injection layer was formed on the hole injection layer using NPD Was vacuum-deposited to a thickness of 60 nm to form a hole transporting layer. Next, a luminescent layer was deposited to a thickness of 30 nm by doping 9,10-di (naphthalen-2-yl) anthracene as a host material and BD-052X (Idemitsu kosan) as a dopant in a 93: 7 weight ratio on a hole transport layer . Followed by forming the electron transporting layer was vacuum-deposited Alq ₃ in 40 nm thick as an electron transport material forming the hole blocking layer by vacuum depositing BAlq on the light emitting layer 10 nm in thickness, and on the hole blocking layer. Subsequently, LiF as a halogenated alkali metal was deposited to a thickness of 0.2 nm to form an electron injecting layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Then, the compound of the present invention (P-1 to P- 80) was deposited to a thickness of 60 nm to form a light-efficiency improvement layer (capping layer), thereby preparing an organic electroluminescent device.

[ Comparative Example  5]

An organic electroluminescent device was fabricated in the same manner as in [Experimental Example III], except that a capping layer was not used.

[ Comparative Example  6]

An organic EL device was prepared in the same manner as in [Experimental Example III] except that Alq ₃ was used instead of the compound of the present invention as a light-emitting efficiency improving layer material.

In the Experimental Example III (Experimental Examples (116) to (140)) and Comparative Example 5 and Comparative Example 6 prepared as described above, a forward bias DC voltage was applied to the organic electroluminescent device and photoresist PR- 650, and the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a reference luminance of 500 cd / m ² .

Table 7 below shows device fabrication and evaluation results for [Experimental Example III] (Experimental Examples (116) to (140)) and Comparative Example 5 and Comparative Example 6 to which the compound according to the present invention was applied.

As can be seen from the results of Tables 5 to 7, the organic electroluminescence device comprising the compound of the present invention as a capping layer can remarkably improve the color purity and luminous efficiency.

Also, comparing the results of the device without the device in the light-efficiency-improvement layer can be confirmed that this may enhance the color purity and efficiency in the light-efficiency-improvement layer, a light-efficiency-improvement layer was used the compound of the present invention than when Alq ₃ il The efficiency is remarkably improved.

In the case of using the light-efficiency-improvement layer, surface plasmon polaritons (SPPs) are generated at the interface between the Mg: Ag electrode and the high-refractive-index organic material. Among them, TE (transverse electric) polarized light is vertically propagated by an evanescent wave The transverse magnetic (TM) polarized light moving along the cathode and the light efficiency improvement layer is amplified by the surface plasma resonance, and the intensity of the peak is generated by the surface plasmon resonance. And thus, it is possible to control the color purity with high efficiency and effective efficiency.

As described above, the compound of the present invention has a high refractive index of 1.8 to 2.1 in the visible light wavelength range (range of 380 nm to 780 nm), and thus the light generated in the organic layer is extracted to the outside of the organic light emitting device As the efficiency is increased, it contributes greatly to the improvement of the light efficiency of the organic light emitting device.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention by those skilled in the art. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

101, 201: substrate 102, 202: first electrode
103, 203: Hole injection layer 104, 204: Hole transport layer
105, 205: light emitting layer 106, 206: electron transporting layer
107, 207: electron injection layer 108, 208: second electrode
109, 209: Light efficiency improvement layer

Claims (11)

A first electrode; A second electrode; At least one organic layer formed between the first electrode and the second electrode; And a light efficiency improvement layer formed on at least one side of one side of the first electrode and the second electrode opposite to the organic material layer,
Wherein the light-efficiency-improvement layer comprises a compound represented by Formula (1).
(1)

[In the above formula (1)
m is an integer of 0 to 4,
n is an integer of 0 to 3,
L ¹ is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A _divalent heterocyclic group of C ₂ to C ₆₀ containing at least one hetero atom selected from O, N, S, Si and P or SO ₂ ; A fluorenylene group; O, N, S, Si and P of the at least one heteroatom or a divalent SO ₂ C ₂ ~ C ₆₀ heterocyclic group and C ₆ ~ C ₆₀ aryl group is a divalent functional group comprising a combination of; And two of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring group; is selected from the group consisting of,
R ¹ and R ² are the same or different from each other when m and n are two or more, and i) independently of one another, deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ² -N (R ^a ) (R ^b ), wherein L ² is a single bond, a C ₆ to C ₆₀ arylene group, a fluorenedylene group, a C ₃ to C ₆₀ 2 is a fused ring group of the aromatic ring of an aliphatic ring and C ₆ ~ C _60; a; and O, N, S, Si and P, at least one heteroatom divalent C ₂ ~ C ₆₀ heterocyclic ring containing a group And R ^a and R ^b are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group, a fluorenyl group, a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring group And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, or ii) a plurality of R ¹ groups or a plurality of R ² Groups are taken together to form an aromatic ring with the carbon to which they are attached, wherein the group not forming a ring is as defined in i)
Ar ¹ to Ar ³ independently represent a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And ^{-L 3 -N (R c) (} R d); selected from the group consisting of: or (wherein L ^3, R ^c and R ^d are as defined in the above L ^2, R ^a and R ^b, respectively), Or ii) Ar &lt; ^{2 &gt;} and Ar &lt; ³ &gt; are bonded to each other to form a ring together with N to which they are bonded,
The aryl group may be substituted with at least one substituent selected from the group consisting of an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, , a germanium group, a cyano group, a nitro ^{group, -L 4 -N (R e)} (R f) ( wherein L as defined in ^4, R ^e and R ^f are the L ^2, R ^a and R ^b, respectively) , C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C of ₂₀ of the aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, fluorene group, O, N, S, a heterocyclic of Si and C ₂ ~ containing at least one hetero atom in the P C ₂₀ group, Which may further be substituted with at least one substituent selected from the group consisting of a C ₃ to C ₂₀ cycloalkyl group, a C ₇ to C ₂₀ arylalkyl group and a C ₈ to C ₂₀ arylalkenyl group, The method according to claim 1,
Wherein L ¹ in the formula (1) is ^one of the following formulas:

[In the formula,
X ¹ is C (R ³ ) or N,
X ² is C (R ⁴ ) (R ⁵ ), N (R ⁶ ), S, SO ₂ or O,
R ³ , Ar ⁴ And Ar &lt; ⁵ &gt; are, independently of each other, hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxy group; And a fluorenyl group;
R ⁴ to R ⁶ are independently selected from: i) a C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxy group; And a fluorenyl group; or ii) R ⁴ and R ⁵ combine with each other to form a spiro compound. The method according to claim 1,
Wherein the formula (1) is one of the following formulas (2) to (13).

[In the above formulas (2) to (13)
^{L 1, Ar 1, Ar 2} , Ar 3, R 1, R 2, m and n are each represented by the above formula ^{(1) L 1, Ar 1} , Ar 2, Ar 3, R 1, R 2, m and n Lt; / RTI &gt; The method according to claim 1,
Wherein the compound represented by the formula (1) is one of the following compounds.

The method according to claim 1,
Wherein the first electrode is an anode formed of ITO containing Ag, the second electrode is a cathode containing Mg-Ag,
Wherein the light-efficiency-improvement layer is formed on one side of the one side of the second electrode opposite to the organic material layer. 6. The method of claim 5,
Wherein the second electrode is a light-transmitting cathode electrode, and the light-efficiency-improvement layer is formed on one side of the second electrode opposite to the organic material layer. The method according to claim 1,
Wherein the organic layer is patterned for R, G, and B pixels, and the light-efficiency-improvement layer is formed as a common layer for the R, G, and B pixels. The method according to claim 1,
The organic layer is patterned for R, G, and B pixels,
The light-efficiency-improvement layer includes a light-efficiency-improvement layer (R) formed in a region corresponding to an R pixel with respect to R, G, and B pixels of the organic material layer, a light- And a light-efficiency-improvement layer (B) formed in a region corresponding to the B pixel. The method according to claim 1,
Wherein the organic material layer is at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. A display device including the organic electroluminescent device of claim 1; And
And a control unit for driving the display device. 11. The method of claim 10,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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