KR102066437B1 - 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 electric device including a light efficiency improving layer and an electronic device including the same.

Description

Organic electroluminescent device including light efficiency improving layer and electronic device comprising same {AN ORGANIC ELECTRONIC ELEMENT COMPRISING A LAYER FOR IMPROVING LIGHT EFFICIENCY, AND AN ELECTRONIC DEVICE COMPRISING THE SAME}

The present invention relates to an organic electric device including a light efficiency improving layer and an electronic device including the same.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

The biggest problem for organic electroluminescent devices is life and efficiency. As the display becomes larger, these efficiency and life problems must be solved. Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage is relatively decreased, and as the result, the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases. It shows a tendency to increase the life.

However, simply improving the organic material layer does not maximize the efficiency, and the energy level and T1 value of each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of the organic material layer are optimal combinations. When achieved, long life and high efficiency can be achieved simultaneously. Therefore, there is a need for development of a light emitting material having high thermal stability and efficiently achieving a charge balance in the light emitting layer. That is, in order to fully exhibit the excellent characteristics of the organic electric device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and the development of the material of the light emitting layer is particularly urgently required.

On the other hand, it delays the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, and stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

In recent years, not only studies that improve the device characteristics by changing the performance of each material, but also improve the color purity and efficiency by the optical thickness optimized between the anode and the cathode in the top device of the resonant structure Is one of the important factors to improve. Compared to the bottom device structure of the non-resonant structure, the TOP device structure has a large optical energy loss due to the surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflecting film, and the light is emitted toward the cathode.

Therefore, one of the important methods for improving the shape and efficiency of the EL spectral is to use a light efficiency improving layer for the p-cathode. In general, the electron emission of SPP is mainly used four metals, Al, Pt, Ag, Au, surface plasmon is generated on the surface of the metal electrode. For example, when the cathode is used as Ag, the light emitted by the Ag of the cathode is quenched by the SPP (light energy loss due to Ag), thereby reducing efficiency.

On the other hand, in the case of using the light efficiency improving layer, SPP is generated at the interface between the MgAg electrode and the high refractive organic material, among which the TE (transverse electric) polarized light is dissipated in the light efficiency improving layer in the vertical direction by the evanescent wave. Transverse magnetic polarized light traveling along the cathode and the light efficiency enhancement layer causes wavelength amplification by surface plasma resonance, resulting in increased peak intensity and eventually high Efficiency and effective color purity can be adjusted.

An object of the present invention is to provide an organic electric device including a high refractive index light efficiency improving layer capable of improving high luminous efficiency, low driving voltage, color purity and lifetime of the device, and an electronic device including the same.

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

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.

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

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, if it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows:

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

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

As used herein, the term "alkenyl group" or "alkynyl group", unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.

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

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto. In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

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

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

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

As used herein, the term “heterocyclic group” includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

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

"Heterocyclic groups" may also include rings comprising SO ₂ in place of the carbon forming the ring. For example, a "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 the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

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

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Unless otherwise stated, the term "carbonyl" used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C 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 Group, germanium group, and C ₂ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

Also, unless otherwise stated, the formulas used in the present invention apply equally to the definitions of substituents based on the exponential definition of the following formulas.

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

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

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

In the case of the top emission method, light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improving layer (CPL) formed of organic material having a relatively high refractive index, thereby amplifying the wavelength of light and thus increasing the light efficiency. do.

In the case of a bottom emission method, the light efficiency of the organic electronic device is improved by interposing the light efficiency improving layer according to the present invention.

Of course, the light efficiency improving layer may not be formed only at this position. 1 and 2 illustrate an example in which an optical efficiency improvement layer is formed on an upper portion of the second electrode and a lower portion of the first electrode, respectively, but in FIG. 1, an optical efficiency improvement layer may be formed on the lower portion of the first electrode as well as the upper portion of the second electrode.

1 and 2, examples of the organic material layer include hole injection layers 103 and 203, hole transport layers 104 and 204, light emitting layers 105 and 205, electron transport layers 106 and 206, and electron injection layers 107. , 207, but at least one of these layers may be omitted.

In addition, although not shown, the organic electroluminescent device may include a hole blocking layer (HBL) that prevents the movement of holes, an electron blocking layer (EBL) that prevents the movement of electrons, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. This may be located further. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In addition, the compound of the present invention may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer as well as the light efficiency improving layer.

The organic electroluminescent device according to another embodiment of the present invention is a metal oxide having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation These alloys are deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material usable as a cathode is deposited thereon. Can be. At this time, the light efficiency improving layer according to the present invention can be formed on the lower or upper anode.

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer 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 material layer and the light efficiency improving layer may use a variety of polymer materials, but not a deposition process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll It can be produced in fewer layers by a process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage that can be manufactured using the color filter technology of the existing LCD while being easy to realize high resolution and excellent processability. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green) and B (Blue) light emitting parts are mutually planarized, and a stacking method in which 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 therefrom. May also be applied to these WOLEDs.

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

Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, 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 electric device according to an aspect of the present invention is provided.

The present invention is a first electrode; Second electrode; One or more organic material layers formed between the first electrode and the second electrode; And an optical efficiency improving layer formed on at least one side of the first electrode and the second electrode opposite to the organic material layer, wherein the optical efficiency improving layer includes a compound represented by Chemical Formula (1). An organic electric device is provided.

Formula (1)

In the above formula (1),

m is an integer from 0 to 4,

n is an integer from 0 to 3,

L ¹ is a single bond; C ₆ ~ C ₆₀ arylene group; C ₂ -C ₆₀ divalent heterocyclic group including at least one heteroatom of O, N, S, Si and P or SO ₂ ; Fluorenylene groups; A divalent functional group in which a C ₂ to C ₆₀ divalent heterocyclic ring containing at least one heteroatom of O, N, S, Si, and P or SO ₂ is combined with an C ₆ to C ₆₀ aryl group; 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 as or different from each other when m and n are each 2 or more, and i) are each independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L ² -N (R ^a ) (R ^b ); (wherein L ² is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and an aromatic ring of C ₆ to C ₆₀ , and a C ₂ to C ₆₀ divalent hetero ring group including at least one hetero atom of O, N, S, Si, and P; R ^a and R ^b are each independently selected from the group consisting of C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group And a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P); or ii) a plurality of R ¹ groups or a plurality of R ^2; Each group is bonded to each other to form an aromatic ring with the carbon to which they are attached, wherein the groups that do not form a ring are as defined in i),

Ar ¹ to Ar ³ are independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L ³ -N (R ^c ) (R ^d ); wherein L ³ , R ^c and R ^d are the same as defined for L ² , R ^a and R ^b , respectively, Or ii) Ar ² and Ar ³ combine with each other to form a ring together with N to which they are attached,

The aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group is deuterium, halogen, silane group, siloxane group, boron group , Germanium group, cyano group, nitro group, -L ⁴ -N (R ^e ) (R ^f ), where L ⁴ , R ^e and R ^f are the same as the definitions of 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, It may be further substituted with one or more substituents selected from the group consisting of C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group.

In another embodiment of the present invention, L ¹ of Formula (1) is one of those represented by the following formula.

In the above 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 ⁵ are, independently from each other, hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And fluorenyl group; selected from the group consisting of,

R ⁴ to R ⁶ are i) independently of each other, an C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ 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, Formula (1) may be one of those represented by the following formula (2) to formula (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 Same as the definition of

In another embodiment of the present invention, the compound represented by 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, the light efficiency improving layer is the second electrode One side of the provides an organic electric device, characterized in that formed on one side opposite to the organic material layer.

In another embodiment of the present invention, the present invention is characterized in that the second electrode is a light transmitting cathode electrode, the light efficiency improving layer is formed on one side of the side opposite to the organic material layer of the second electrode Provides an electrical device.

In another embodiment of the present invention, the organic layer is characterized in that the organic material layer is patterned for each of the R, G, B pixels, the light efficiency improvement layer is formed as a common layer for the R, G, B pixels Provided is an element.

In another embodiment of the present invention, the organic material layer is patterned for each of the R, G, B pixels, the light efficiency improvement layer, in the region corresponding to the R pixel for the R, G, B pixels of the organic material layer. And at least one of the formed light efficiency improving layer R, the light efficiency improving layer G formed in the region corresponding to the G pixel, and the light efficiency improving layer B formed in the region corresponding to the B pixel. It provides an organic electric device.

In another embodiment of the present invention, the organic material layer provides an organic electric element, characterized in that at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer.

In another embodiment of the present invention, the present invention is a display device comprising the organic electroluminescent element of claim 1; And a controller 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 device for monochrome or white illumination.

Hereinafter, the synthesis examples of the chemical formulas according to the present invention and the production examples of the organic electric element will be described in detail by way of examples, but the present invention is not limited to the following examples.

Synthesis Example

Final products according to the present invention (final products) are prepared by reacting Sub 2 or Sub 3 to Sub 1, as shown in Schemes 1-1 and 1-2.

<Scheme 1-1>

<Scheme 1-2>

One. Sub  1, Synthesis

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.

<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 Synthesis Example

<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 in 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), Cu (2.6 g, 40.8 mmol) was added and stirred at 200 ° C. After the reaction was completed, nitrobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated and the resulting compound was silicagel column and recrystallized to give the product 32.03 g (yield: 73%).

Intermediate Sub  One- II -11 synthetic

Sub 1-I-11 (32.03 g, 99.4 mmol) obtained in the above synthesis was dissolved in DMF in a round bottom flask, followed by 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 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was purified by silicagel column and recrystallized to give 30.83 g (yield: 84%) of the product.

Sub  1-11 Synthesis

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

(2) Sub  1-17 Synthesis Example

<Scheme 4>

Intermediate Sub  1-I-17 Synthesis

2-iodonaphthalene (19.23 g, 75.7 mmol) in 2-bromo-9 H -carbazole (12.42 g, 50.5 mmol), Na ₂ SO ₄ (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 to obtain 13.15 g (yield: 70%) of the product.

Intermediate Sub  One- II -17 synthetic

To Sub 1-I-17 (13.15 g, 35.5 mmol) obtained in the above 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 using the Sub 1-II-11 synthesis described above to give 11.7 g (yield: 79%) of product.

Sub  1-17 synthesis

To Sub 1-II-17 (11.7 g, 27.9 mmol) obtained in the above synthesis 4-bromo-4'-iodo-1,1'-biphenyl (15.03 g, 41.9 mmol), Pd (PPh ₃ ) ₄ (1.61 g , 1.4 mmol), K ₂ CO ₃ (11.57 g, 83.7 mmol), THF, and water were obtained using the Sub 1-11 synthesis method to obtain 10.68 g (yield: 73%) of the product.

 (3) Sub  1-24 Synthesis Example

Scheme 5

Sub  1-24 synthesis

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

(4) Sub  1-44 Synthesis Example

<Scheme 6>

Intermediate Sub  1-I-44 Synthesis

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 to obtain 25.98 g (yield: 74%) of the product.

Intermediate Sub  One- II -44 synthetic

To Sub 1-I-44 (25.98 g, 69.8 mmol) obtained in the above synthesis, Bis (pinacolato) diboron (19.49 g, 76.8 mmol), Pd (dppf) Cl ₂ (1.71 g, 2.1 mmol), KOAc (20.55 g, 209.4 mmol) and DMF were obtained using the Sub 1-II-11 synthesis method to obtain 23.41 g (yield: 80%) of product.

Sub  1-44 Synthesis

To Sub 1-II-44 (23.41 g, 55.8 mmol) obtained in the above synthesis, 2,7-dibromo-9-phenyl-9 H -carbazole (33.59 g, 83.7 mmol), Pd (PPh ₃ ) ₄ (3.23 g, 2.8 mmol), K ₂ CO ₃ (23.15 g, 167.5 mmol), THF, and water were obtained using the Sub 1-11 synthesis, to obtain 23.98 g (yield: 70%) of the product.

 (5) Sub  1-57 Synthesis Example

Scheme 7

Intermediate Sub  1-I-57 Synthesis

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

Intermediate Sub  One- II -57 synthetic

To Sub 1-I-57 (12.21 g, 32.8 mmol) obtained in the above 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 using the Sub 1-II-11 synthesis method to obtain 10.59 g (yield: 77%) of product.

Sub  1-57 Synthesis

To 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 obtained using the Sub 1-11 synthesis method to obtain 10.54 g (yield: 68%) of the product.

Meanwhile, examples of Sub 1 are as follows, but are not limited thereto, and their FD-MSs are shown in Table 1 below.

2. Sub  2, synthesis

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 8 below.

Scheme 8

(One) Sub  2-1 Synthesis Example

Scheme 9

After starting bromobenzene (10.02 g, 63.8 mmol) was 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 mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 8.64 g (yield: 80%).

(2) Sub  2-5 Synthesis Example

Scheme 10

To the starting material 1-bromonaphthalene (4.16 g, 20.1 mmol) aniline (3.74 g, 40.2 mmol), Pd ₂ (dba) ₃ (0.55 g, 0.6 mmol), 50% P ( t -Bu) ₃ (0.8ml, 1.6 mmol), NaO t -Bu (5.79 g, 60.3 mmol) and toluene were obtained using the Sub 2-1 synthesis method to obtain 3.57 g (yield: 81%) of the product.

(3) Sub  2-24 Synthesis Example

Scheme 11

In the starting material 2-bromothiophene (3.65 g, 22.4 mmol) naphthalen-1-amine (6.41 g, 44.8 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.7 mmol), 50% P ( t -Bu) ₃ (0.9ml, 1.8 mmol), NaO t -Bu (6.45 g, 67.2 mmol) and toluene were obtained using the Sub 2-1 synthesis method to yield 3.73 g (yield: 74%) of the product.

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

3. Sub  3, synthesis

Sub 3 of Scheme 1 may be synthesized by the reaction pathway of Scheme 12.

Scheme 12

(One) Sub  3-1 Synthesis Example

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, followed by Pd (OAc) ₂ (0.26 g, 1.1 mmol) and PCy ₃ · HCF ₄ (0.84 g , 2.3 mmol), K ₂ CO ₃ (10.55 g, 76.3 mmol) were added and stirred at 130 ° C. After the reaction was completed, N , N -dimethylacetamide was removed by distillation, and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated and the resulting compound was silicagel column and recrystallized to give the product 5.68 g (yield: 89%).

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

4. End product ( Final Products ) Synthesis

Sub 2 or Sub 3 (1 equiv) is dissolved in toluene in a round bottom flask, then Sub 1 (1.1 equiv), Pd ₂ (dba) ₃ (0.03 equiv), P (t-Bu) ₃ (0.08 equiv), NaO t- Bu (3 equiv) was added and stirred at 100 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a final product (Final Products).

(1) P-9 Synthesis Example

Scheme 14

Sub 2-24 (3.31 g, 14.7 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, and then Sub 1-11 (7.67 g, 16.2 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) , 50% P ( t -Bu) ₃ (0.6 ml, 1.2 mmol), NaO t -Bu (4.24 g, 44.1 mmol) was added and stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ , and the concentrated compound was recrystallized from a silicagel column to obtain 6.82 g (yield: 75%) of the product.

(2) P-13 Synthesis Example

Scheme 15

Sub 2-1 (2.58 g, 15.2 mmol) obtained in the above synthesis to Sub 1-24 (8.46 g, 16.8 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.5 mmol), 50% P ( t -Bu) ₃ (0.6 ml, 1.2 mmol), NaO t -Bu (4.4 g, 45.7 mmol) and toluene were obtained using the P-9 synthesis method to yield 7.14 g (yield: 79%) of the product.

(3) P-35 Synthesis Example

Scheme 16

Sub 2-1 (2.12 g, 12.5 mmol) obtained in the above synthesis to Sub 1-17 (7.23 g, 13.8 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.4 mmol), 50% P ( t -Bu) ₃ (0.5 ml, 1 mmol), NaO t -Bu (3.61 g, 37.6 mmol) and toluene were obtained using the P-9 synthesis method to give 6.37 g (yield: 83%) of product.

(4) P-49 Synthesis Example

Scheme 17

Sub 2-1 (2.34 g, 13.8 mmol) obtained in the above synthesis in Sub 1-44 (9.33 g, 15.2 mmol), Pd ₂ (dba) ₃ (0.38 g, 0.4 mmol), 50% P ( t -Bu) ₃ (0.5 ml, 1.1 mmol), NaO t -Bu (3.99 g, 41.5 mmol) and toluene were obtained using the P-9 synthesis method and yielding 7.76 g (yield: 80%) of the product.

(5) P-57 Synthesis Example

Scheme 18

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

(6) P-63 Synthesis Example

Scheme 18

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

(7) P-66 Synthesis Example

Scheme 19

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

On the other hand, FD-MS values of the compounds P-1 ~ P-80 of the present invention prepared according to the synthesis examples as described above are shown in Table 4.

On the other hand, in the above described an exemplary synthesis example of the present invention represented by the formula (1), these all 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 reactions, even if other substituents (R ₁ , R ₂ , L ₁ , Ar ₁ to Ar ₃ ) defined in Formula 1 are bound, in addition to the substituents specified in the specific synthesis examples. It will be readily understood by one skilled in the art that this proceeds. For example, the starting material-> Sub 1-I reaction in Scheme 2 is based on the Ullmann reaction, the Sub 1-I-> Sub 1-II reaction in Scheme 2 is based on the Miyaura boration reaction, and the Sub 1-II reaction in Scheme 2 The Sub 1 reaction is based on the Suzuki cross-coupling reaction. Sub 2-> Sub 3 reaction in Scheme 12 is based on direct intramolecular arylation reaction, starting material-> Sub 2 reaction in Scheme 8, product synthesis scheme (Scheme 14-19) is based on Buchwald-Hartwig cross coupling reaction As such, the reactions will proceed even if substituents not specifically specified in them are attached.

Manufacturing Evaluation of Organic Electrical Device

Mg: Ag of a device including a pair of electrodes of a first electrode (anode) and a second electrode (cathode) An optical efficiency improving layer (capping layer) formed on the second electrode (cathode), including the compound of the present invention A manufacturing example for the organic electroluminescent device is described.

[ Experimental Example  I] Red organic electroluminescent device

Prepared with a reflective ITO substrate containing Ag on a 10 mm x 10 mm x 1 mm glass substrate, and abbreviated as 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter 2-TNATA) ) Was vacuum deposited to form a hole injection layer having a thickness of 60 nm, and then 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter, referred to as a hole transport compound on the hole injection layer). Abbreviated as NPD) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Next, CBP [4,4'- N, N'-dicarbazole-biphenyl] is used as a host material on the hole transport layer and (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) as a dopant material. ) acetylacetonate] in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30nm. Subsequently, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm on the light emitting layer. A blocking layer was formed, and an electron transport layer was formed by vacuum depositing tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) to a thickness of 40 nm as an electron transport compound on the hole blocking layer. Subsequently, LiF, an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al is deposited to a thickness of 150 nm to form a cathode. An organic electroluminescent device was manufactured by depositing a compound corresponding to one of 80) to a thickness of 60 nm to form a capping layer.

[ Comparative example  One]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example I], except that no light efficiency improving layer was used.

[ Comparative example  2]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example I], except that Alq ₃ was used instead of the compound of the present invention as the light efficiency improving layer material.

[Experimental Example I] (Experimental Example (1) to Experimental Example (72)), Comparative Example 1, and Comparative Example 2 prepared as described above were applied to the organic electroluminescent device by applying a forward bias DC voltage to PR-photoresearch (PR). The electroluminescence (EL) characteristics were measured at 650, and the T95 life was measured using a life-time measuring instrument manufactured by McScience Inc. at a luminance of 2500 cd / m ² .

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

[ Experimental Example II Green Organic Light Emitting Diode

After preparing a reflective ITO substrate containing Ag on a 10 mm x 10 mm x 1 mm glass substrate, 2-TNATA was vacuum-deposited thereon to form a hole injection layer having a thickness of 60 nm, and then NPD as a hole transport compound on the hole injection layer. Was vacuum deposited to a thickness of 60 nm to form a hole transport 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 Doped at a weight ratio to deposit a light emitting layer to a thickness of 30nm. Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer as an electron transport compound to 40 nm in thickness to form an electron transport layer. Subsequently, LiF, an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al is deposited to a thickness of 150 nm to form a cathode. An organic electroluminescent device was manufactured by depositing a compound corresponding to one of 80) to a thickness of 60 nm to form a capping layer.

[ Comparative example  3]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example II], except that no light efficiency improving layer was used.

[ Comparative example  4]

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

[Experimental Example II] (Experimental Example (73) to Experimental Example (115)), Comparative Example 3, and Comparative Example 4 prepared as described above were applied to the organic electroluminescent device by applying a forward bias DC voltage to PR-photoresearch (PR). Electroluminescence (EL) characteristics were measured at 650, and the T95 life was measured using a life-time measuring instrument manufactured by McScience Inc. at a luminance of 5000 cd / m ² .

Table 6 below shows the device fabrication and evaluation results of [Experimental Example II] (Experimental Example (73) to Experimental Example (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

After preparing a reflective ITO substrate containing Ag on a 10 mm x 10 mm x 1 mm glass substrate, 2-TNATA was vacuum-deposited thereon to form a hole injection layer having a thickness of 60 nm, and then NPD as a hole transport compound on the hole injection layer. Was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Next, 9,10-di (naphthalen-2-yl) anthracene as a host material and BD-052X (Idemitsu kosan) as a dopant material were doped in a weight ratio of 93: 7 on the hole transport layer to deposit a light emitting layer having a thickness of 30 nm. . Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer as an electron transport compound to 40 nm in thickness to form an electron transport layer. Subsequently, LiF, an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al is deposited to a thickness of 150 nm to form a cathode. The organic electroluminescent device was manufactured by depositing a compound corresponding to one of 80) to a thickness of 60 nm to form a capping layer.

[ Comparative example  5]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example III], except that no light efficiency improving layer was used.

[ Comparative example  6]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example III], except that Alq ₃ was used instead of the compound of the present invention as the light efficiency improving layer material.

[Experimental Example III] (Experimental Example (116) to Experimental Example 140), Comparative Example 5 and Comparative Example 6 prepared as described above were applied to the organic electroluminescent device by applying a forward bias DC voltage to PR- Photoresearch Co. Electroluminescence (EL) characteristics were measured at 650, and the T95 lifetime was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 500 cd / m ² .

Table 7 below shows the device fabrication and evaluation results of [Experimental Example III] (Experimental Example (116) to Experimental Example (140)), 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 electroluminescent device comprising the compound of the present invention as a light efficiency improving layer (capping layer) can significantly improve the high color purity and luminous efficiency.

In addition, when comparing the results of the device with and without the light efficiency improving layer it can be seen that the color purity and efficiency can be increased to the light efficiency improving layer, the compound of the present invention was used when the light efficiency improving layer is Alq ₃ It can be seen that the efficiency is remarkably improved at the time.

When the light efficiency improving layer is used, SPPs (surface plasmon polaritons) are generated at the interface between the Mg: Ag electrode and the highly refractive organic material. Transverse magnetic (TM) polarized light, which disappears from the CPL plane and moves along the cathode and the light efficiency improving layer, has an amplification of the wavelength due to surface plasma resonance, resulting in peak intensity. It is believed that this is due to the increased efficiency and effective color purity control.

As described above, in the visible light wavelength range (380 nm to 780 nm), the compound of the present invention has a high refractive index of 1.8 to 2.1. Accordingly, light generated in the organic layer is extracted outside the organic light emitting device by the principle of constructive interference. Increasing the efficiency greatly contributes to improving the light efficiency of the organic light emitting device.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted 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 transport layer
107 and 207 electron injection layer 108 and 208 second electrode
109, 209: light efficiency improving layer

Claims (11)

A first electrode; Second electrode; One or more organic material layers formed between the first electrode and the second electrode; And an optical efficiency improving layer formed on at least one side of the first electrode and the second electrode opposite to the organic material layer.
The optical efficiency improving layer is an organic electroluminescent device comprising a compound represented by Formula 1:
<Formula 1>

In Chemical Formula 1,
R ¹ and R ² independently of each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L ² -N (R ^a ) (R ^b ; selected from the group consisting of at least one pair of neighboring R ¹ combine with each other to form an aromatic ring, or adjacent R ¹ or adjacent R ² Can combine to form an aromatic ring,
m is an integer of 0 to 4, n is an integer of 0 to 3, each of R ¹ is the same or different when m is an integer of 2 or more, each of R ² is the same or different when n is an integer of 2 or more,
L ¹ is a single bond; C ₆ ~ C ₆₀ arylene group; C ₂ -C ₆₀ divalent heterocyclic group including at least one heteroatom of O, N, S, Si and P or SO ₂ ; Fluorenylene groups; A divalent functional group in which a C ₂ to C ₆₀ divalent heterocyclic ring containing at least one heteroatom of O, N, S, Si, and P or SO ₂ is combined with an C ₆ to C ₆₀ aryl group; 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,
Ar ¹ to Ar ³ are independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L ³ -N (R ^c ) (R ^d ); Ar ² and Ar ³ are bonded to each other to form a heterocycle with N to which they are bonded,
However, the Ar ² and Ar ^3, and if a heterocyclic group containing N, the heterocyclic group of Ar ² and Ar ³ C ₂ ~ C ₉ heterocyclic group,
R ^a , R ^b , R ^c and R ^d are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and
L ² and L ³ are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; Divalent fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And a C ₂ ~ C _{60 divalent} heterocyclic group including at least one heteroatom of O, N, S, Si, and P;
The aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, respectively, deuterium, halogen, silane group, siloxane group, cyan group, a nitro group, C ₁ ~ C ₂₀ coming of the alkylthio, C ₁ ~ C ₂₀ alkynyl of the alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the group, a C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, fluorene group, O, N, S, C ₂ ~ containing at least one hetero atom of Si and P C ₉ It may be further substituted with one or more substituents selected from the group consisting of a heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group. The method of claim 1,
L ¹ is an organic electric device characterized in that one of the formula:

In the above 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 ⁵ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And fluorenyl group; selected from the group consisting of,
R ⁴ to R ⁶ are each independently C ₆ ~ C ₆₀ An aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And fluorenyl group; selected from the group consisting of, R ⁴ and R ⁵ may be bonded to each other to form a spiro compound. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by one of the following formula (2):

In Formulas 2 to 8, L ¹ , Ar ¹ , Ar ² , Ar ³ , R ¹ , R ² , m and n are the same as defined in claim 1. The method of claim 1,
The compound represented by Chemical Formula 1 is one of the following compounds:

. The method of claim 1,
The first electrode is an anode formed of ITO containing Ag, the second electrode is a cathode containing Mg-Ag,
The optical efficiency improving layer is formed on one side of the second electrode opposite to the organic material layer, characterized in that the organic electric element. The method of claim 5,
And the second electrode is a light transmissive cathode electrode, and the light efficiency improving layer is formed on one side of the second electrode opposite to the organic material layer. The method of claim 1,
The organic material layer is patterned for each of R, G, and B pixels, and the light efficiency improving layer is formed as a common layer for the R, G, and B pixels. The method of claim 1,
The organic layer is patterned for each of R, G, and B pixels,
The light efficiency improving layer may include a light efficiency improving layer R formed in a region corresponding to an R pixel for the R, G, and B pixels of the organic material layer, a light efficiency improving layer G formed in a region corresponding to the G pixel, And at least one of a light efficiency improving layer (B) formed in a region corresponding to the B pixel. The method of claim 1,
The organic material layer is at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer. A display device comprising the organic electroluminescent element of claim 1; And
And a controller for driving the display device. The method of claim 10,
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 monochrome or white illumination device.

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