Patent Description:
In general, organic light emitting phenomenon refers to a phenomenon that converts electric energy into light energy by 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 interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is often composed of a multi-layered structure composed of different materials, and for example, may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an 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 depending on its function.

And the light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and into a fluorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons depending on the light emitting mechanism. Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color.

Meanwhile, 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 drops, or the efficiency of the device decreases due to the light emission attenuation effect, therefore a host / dopant system can be used as a light emitting material in order to increase luminous efficiency through increase of color purity and energy transfer. When the small amount of dopant having a smaller energy band gap than the host forming the emitting layer is mixed on the emitting layer, the excitons generated in the 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, light of a desired wavelength can be obtained depending on the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

Efficiency, life span, driving voltage and the like are related to each other. As the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage drops, the crystallization of the organic material due to joule heating generated during driving is reduced, and as a result, the life span tends to increase. However, simply improving the organic material layer cannot maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time. Therefore, it is necessary to develop a light emitting material having a high thermal stability and achieving a charge balance in the emitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electric element, a material for forming an organic material layer in an element such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an emitting-auxiliary layer material, and the like should be supported by stable and efficient materials. However, such a stable and efficient organic material layer material for an organic electric element has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and especially development of host materials for the emitting layer is urgently required.

Otherwise, in the case of a polycyclic compound including a heteroatom, the difference in properties according to the material structure is so large that it is applied to various layers as OLED material. In particular, it has characteristics of different band gaps (HOMO, LUMO), electrical characteristics, chemical properties, and physical properties depending on the number of rings, fused positions and the type and arrangement of heteroatoms, therefore application development for various OLED layers using the same has been progressed. Recently, development of OLED material for heteroatom type, number and position of pentacyclic compounds has been actively developed.

As a precedent reference, <CIT> is referred to.

<CIT> and <CIT> describe organic electronic elements comprising an auxiliary layer and various polycyclic compounds to be used in the auxiliary layer. Documents <CIT>, <CIT> and <CIT> describe further organic electronic elements.

Using the characteristics of the polycyclic compound, the present invention provides a compound capable of maximizing the effect of improving luminous efficiency and long life, while maintaining or slightly reducing the driving voltage of the device, and an organic electric element using the same and an electronic device thereof.

The aspects of the invention are as recited in the appended set of claims. Irrespective of any statement made in the remainder of the description, the embodiments of the invention are solely as detailed in the appended set of claims.

The present invention provides compounds represented by Formula (<NUM>), organic electric elements comprising the same and electronic devices thereof.

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 element, and can greatly improve the color purity and lifetime of the element.

<FIG> illustrates an example of an organic electric element according to the present invention.

Hereinafter, some embodiments of the present invention will be described in detail. Further, 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 addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. It should be noted that if a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected ", " coupled" or "connected" between each component.

As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term "halo" or "halogen" , as used herein, includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term "alkyl" or "alkyl group" , as used herein, has a single bond of <NUM> to <NUM> carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.

Unless otherwise stated, the term "haloalkyl" or "halogen alkyl" , as used herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term "heteroalkyl" , as used herein, means alkyl substituted one or more of carbon atoms consisting of an alkyl with heteroatom.

Unless otherwise stated, the term "alkenyl" or "alkynyl" , as used herein, has double or triple bonds of <NUM> to <NUM> carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term "cycloalkyl" , as used herein, means alkyl forming a ring having <NUM> to <NUM> carbon atoms, but is not limited thereto.

Unless otherwise stated, the term "alkoxyl group" , "alkoxy group" or "alkyloxy group" , as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has <NUM> to <NUM> carbon atoms.

Unless otherwise stated, the term "alkenoxyl group" , "alkenoxy group" , "alkenyloxyl group" or "alkenyloxy group" , as used herein, means an oxygen radical attached to an alkenyl group, but is not limited thereto, and has <NUM> to <NUM> carbon atoms.

Unless otherwise stated, the term "aryloxyl group" or "aryloxy group" , as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has <NUM> to <NUM> carbon atoms.

Unless otherwise stated, the term "aryl group" or "arylene group" , as used herein, has <NUM> to <NUM> carbon atoms, but is not limited thereto. Herein, the aryl group or arylene group means a monocyclic and polycyclic aromatic group, and may also be formed in conjunction with an adjacent group. Examples of "aryl group" may include a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalkenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.

Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term "heteroalkyl" , as used herein, means alkyl including one or more of heteroatoms. Unless otherwise stated, the term "heteroaryl group" or "heteroarylene group" , as used herein, means a C2 to C60 aryl including one or more of heteroatoms or arylene group, but is not limited thereto, and includes at least one of monocyclic and polycyclic rings, and may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term "heterocyclic group" , as used herein, contains one or more heteroatoms, but is not limited thereto, has <NUM> to <NUM> carbon atoms, includes any one of monocyclic and polycyclic rings, and may include heteroaliphatic ring and/or heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term "heteroatom" , as used herein, represents at least one of N, O, S, P, or Si.

Also, the term "heterocyclic group" may include a ring including SO<NUM> instead of carbon consisting of cycle. For example, "heterocyclic group" includes compound below.

Unless otherwise stated, the term "aliphatic" , as used herein, means an aliphatic hydrocarbon having <NUM> to <NUM> carbon atoms, and the term "aliphatic ring" , as used herein, means an aliphatic hydrocarbon ring having <NUM> to <NUM> carbon atoms.

Unless otherwise stated, the term "ring" , as used herein, means an aliphatic ring having <NUM> to <NUM> carbon atoms, or an aromatic ring having <NUM> to <NUM> carbon atoms, or a hetero ring having <NUM> to <NUM> carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

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

Unless otherwise stated, the term "carbonyl" , as used herein, is represented by -COR' , wherein R' may be hydrogen, an alkyl having <NUM> to <NUM> carbon atoms, an aryl having <NUM> to <NUM> carbon atoms, a cycloalkyl having <NUM> to <NUM> carbon atoms, an alkenyl having <NUM> to <NUM> carbon atoms, an alkynyl having <NUM> to <NUM> carbon atoms, or the combination of these.

Unless otherwise stated, the term "ether" , as used herein, is represented by -R-O-R' , wherein R or R' may be independently hydrogen, an alkyl having <NUM> to <NUM> carbon atoms, an aryl having <NUM> to <NUM> carbon atoms, a cycloalkyl having <NUM> to <NUM> carbon atoms, an alkenyl having <NUM> to <NUM> carbon atoms, an alkynyl having <NUM> to <NUM> carbon atoms, or the combination of these.

Unless otherwise stated, the term "substituted or unsubstituted" , as used herein, means that substitution is substituted by at least one substituent selected from the group consisting of, but is not limited thereto, deuterium, halogen, an amino group, a nitrile group, a nitro group, a C<NUM>-C<NUM> alkyl group, a C<NUM>-C<NUM> alkoxyl group, a C<NUM>-C<NUM> alkylamine group, a C<NUM>-C<NUM> alkylthiophene group, a C<NUM>-C<NUM> arylthiophene group, a C<NUM>-C<NUM> alkenyl group, a C<NUM>-C<NUM> alkynyl group, a C<NUM>-C<NUM> cycloalkyl group, a C<NUM>-C<NUM> aryl group, a C<NUM>-C<NUM> aryl group substituted by deuterium, a C<NUM>-C<NUM> arylalkenyl group, a silane group, a boron group, a germanium group, and a C<NUM>-C<NUM> heterocyclic group.

Unless otherwise expressly stated, the Formula used in the present invention, as used herein, is applied in the same manner as the substituent definition according to the definition of the exponent of the following Formula.

Wherein, when a is an integer of zero, it means the substituent R<NUM> is absent. That is, when a is <NUM>, it means that all the carbons forming the benzene ring are bonded to hydrogen. In this case, the sign of the hydrogen bonded to the carbon may be omitted and the formula or compound may be described. When a is an integer of <NUM>, the sole substituent R<NUM> is linked to any one of the carbon constituting the benzene ring, when a is an integer of <NUM> or <NUM>, they are respectively bonded as follows, in which R<NUM> may be the same as or different from each other, and when a is an integer of <NUM> to <NUM>, and it is bonded to the carbon of the benzene ring in a similar manner, whereas the indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present invention and an organic electric element comprising the same will be described.

In an embodiment not in accordance with the present invention, there is provided a compound represented by Formula (<NUM>).

In a specific aspect, the compound represented by Formula (<NUM>) comprises a compound represented by any of Formulas (<NUM>) to (<NUM>) below. <CHM>
<CHM>.

In Formulas (<NUM>) to (<NUM>);
Ar<NUM>, Ar<NUM>, Ar<NUM>, l, m, n, a, b, c, d, e, R<NUM>, R<NUM>, R<NUM>, R<NUM> and R<NUM> are the same as defined above.

Preferably, at least one of Ar<NUM>, Ar<NUM>, and R<NUM> in Formula (<NUM>) comprises a C<NUM>~C<NUM> aryl group, more preferably, Ar<NUM> or Ar<NUM> in Formula (<NUM>) comprises a C<NUM>~C<NUM> aryl group.

Also, R<NUM> in Formula (<NUM>) is a C<NUM>~C<NUM> aryl group.

Also, Formula (<NUM>) comprises a compound represented by any of the following Formulas (<NUM>) to (<NUM>)
<CHM>.

In Formulas (<NUM>) to (<NUM>),
Ar<NUM>, Ar<NUM>, Ar<NUM>, l, m, n, a, b, c, d, e, R<NUM>, R<NUM>, R<NUM>, R<NUM> and R<NUM> are the same as defined above.

Also, the compound represented by Formula (<NUM>) comprises compounds represented by Formula (<NUM>)
<CHM>.

In Formula (<NUM>),
Ar<NUM>, Ar<NUM>, Ar<NUM>, l, m, n, a, b, c, d, e, R<NUM>, R<NUM>, R<NUM>, R<NUM> and R<NUM> are the same as defined above.

Specifically, the compound represented by Formula (<NUM>) includes the following compounds P-<NUM> to P-<NUM>. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

In another aspect, there is provided an organic electric element comprising a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and including a compound included in Formula (<NUM>).

Wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting auxiliary layer, an emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one of the hole injection layer, the hole transport layer, the emitting auxiliary layer, the emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer comprises one compound or <NUM> or more compounds of Formula (<NUM>). Preferably, the compound is included in the emitting layer.

More specifically, the aspect provides an organic electronic element further comprising a compound represented by Formula (<NUM>) in the emitting layer.

Formula (<NUM>) comprises a compound represented by any of the following Formulas (<NUM>) to (<NUM>). <CHM>
<CHM>.

In Formulas (<NUM>) to (<NUM>),
Ar<NUM>, Ar<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, L<NUM>, R' , R" are the same as defined above.

Preferably, both Ar<NUM> and Ar<NUM> of Formula (<NUM>) comprise a compound represented by a C<NUM>-C<NUM> aryl group.

Also, the compound represented by Formula (<NUM>) comprises a compound represented by Formula(<NUM>):
<CHM>.

In Formula(<NUM>),
Ar<NUM>, Ar<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, Z<NUM>, and L<NUM> are the same as defined above.

Specifically, the compound represented by Formula (<NUM>) comprises the following compounds <NUM>-<NUM> to <NUM>-<NUM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

As another example, there is provided an organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode; wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer formed between the emitting layer and the hole transport layer; wherein the hole transport layer or the emitting auxiliary layer comprises a compound represented by Formula(<NUM>), and the emitting layer comprises a compound represented by Formula(<NUM>).

In a further aspect there is provided an organic electronic element including at least one compound represented by Formula (<NUM>) in the emitting layer.

Also, the hole transport layer comprises a compound represented by Formula(<NUM>) or Formula(<NUM>), and the emitting auxiliary layer comprises a compound represented by Formula(<NUM>) or Formula(<NUM>):
<CHM>.

Specifically, the compound represented by Formula (<NUM>) comprises the following compounds <NUM>-<NUM> to <NUM>-<NUM> and compounds <NUM>-<NUM> to <NUM>-<NUM>. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

As another example, there is provided an organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode; wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer or an electron blocking layer(EBL)formed between the emitting layer and the hole transport layer; wherein the emitting auxiliary layer or the electron blocking layer comprises a compound represented by Formula(<NUM>).

In present invention the compound represented by Formula (<NUM>) is represented by Formulas(<NUM>) and (<NUM>) to (<NUM>). Formula(<NUM>) and Formulas(<NUM>) to (<NUM>) are not forming part of the claimed invention. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

In Formulas(<NUM>) to (<NUM>),
R<NUM> , R<NUM>, R<NUM>, R<NUM>, R<NUM>, R<NUM>, L<NUM>, L<NUM>, Ar<NUM> and X<NUM>, u, v, w, x, y and z are the same as defined above.

The compound represented by Formula(<NUM>) comprises the following compounds. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

Referring to <FIG>, the organic electric element(<NUM>) according to the present invention includes a first electrode(<NUM>) formed on a substrate(<NUM>), a second electrode(<NUM>), and an organic material layer including the compound represented by Formula (<NUM>) between the first electrode(<NUM>) and the second electrode(<NUM>). Here, the first electrode(<NUM>) may be an anode (positive electrode), and the second electrode(<NUM>) may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer(<NUM>), a hole transport layer(<NUM>), an emitting layer(<NUM>), an emitting auxiliary layer(<NUM>), an electron transport layer(<NUM>), and an electron injection layer(<NUM>) formed in sequence on the first electrode(<NUM>). Here, the remaining layers except the emitting layer(<NUM>) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer(<NUM>), an electron transport auxiliary layer, a buffer layer(<NUM>), etc., and the electron transport layer(<NUM>) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to the present invention may further include a protective layer formed on at least one side of the first and second electrodes, which is a side opposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electrical characteristics, the interface characteristics, and the like may vary depending on which substituent is bonded at which position, therefore the choice of core and the combination of sub-substituents associated therewith is also very important, and in particular, when the optimal combination of energy levels and T1 values and unique properties of materials(mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long life span and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a cathode, and the organic material layer including the hole injection layer(<NUM>), the hole transport layer(<NUM>), the emitting layer(<NUM>), the electron transport layer(<NUM>), and the electron injection layer(<NUM>) is formed thereon, and then depositing a material usable as a cathode thereon can manufacture an organic electroluminescent device according to an embodiment of the present invention. In addition, an emission auxiliary layer(<NUM>) comprising the compound of Formula (<NUM>) is further formed between the hole transport layer(<NUM>) and the emitting layer(<NUM>), and an electron transport auxiliary layer may be further formed between the emitting layer(<NUM>) and the electron transport layer (<NUM>).

As another specific example, the present invention provides an organic electric element wherein the emitting layer in the organic material layer is a phosphorescent light emitting layer.

The compounds represented by Formula (<NUM>) and (<NUM>) are mixed in a ratio of any one of <NUM>: <NUM> to <NUM>: <NUM> to be included in the emitting layer of the organic material layer, wherein the compound represented by Formula (<NUM>) is further mixed to be included in the emitting layer.

The present invention may further include a light efficiency enhancing layer formed on at least one of the opposite side to the organic material layer among one side of the first electrode, or one of the opposite side to the organic material layer among one side of the second electrode.

As another example, the present invention provides an organic electronic device wherein the compound represented by Formula (<NUM>) is used in an emitting auxiliary layer or an electron blocking layer and is preferably included in a green emitting auxiliary layer. More specifically, the compound represented by Formula (<NUM>) or Formula (<NUM>) is included in the green emitting auxiliary layer.

Also, the present invention provides the organic electric element wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and 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 method of forming the organic material layer.

The organic electric element according to an embodiment of the present invention may be a front 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 excellent fairness, and can be manufactured using conventional LCD color filter technology. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Representatively, there are side-by-side arrangement of the radiation part of the R(red), G(green) and B(blue), a stacking method in which R, G, and B emitting layers are laminated on top and bottom, electroluminescence by the blue (B) organic emitting layer and, by using the light from this, a color conversion material (CCM) method using a photo-luminescence of an inorganic phosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising a display device including the organic electric element; and a control unit for driving the display device.

According to another aspect, the present invention provides an display device wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor(organic TFT) and an element for monochromic or white illumination. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant(PDA), an electronic dictionary, a point-to-multipoint(PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula (<NUM>) and (<NUM>) and preparation examples of the organic electric element will be described in detail by way of example, but are not limited to the following examples.

Final product1 represented by Formula(<NUM>) (not forming part of the claimed invention) is prepared by reacting Core and Sub as shown in Reaction Scheme <NUM> below, but is not limited thereto.

The Core of the Reaction Scheme <NUM> can be synthesized by the reaction path of the following Reaction Schemes <NUM>, but is not limited thereto.

In a round bottom flask, <NUM>,<NUM>,<NUM>-trichloro-<NUM>,<NUM>,<NUM>-triazine (<NUM>, <NUM> mmol), phenylboronic acid (<NUM>, <NUM> mmol), Pd(PPh<NUM>)<NUM> (<NUM>, <NUM> mmol), K<NUM>CO<NUM> (<NUM>, <NUM>. 2mol), THF (<NUM>) and water(<NUM>) were added and stirred at <NUM> ° C. When the reaction was complete, the reaction mixture was extracted with CH<NUM>Cl<NUM> and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of Inter <NUM>.

In a round bottom flask, Inter-<NUM> (<NUM>, <NUM> mmol), dibenzo[b,d]furan-<NUM>-ylboronic acid(<NUM>, <NUM> mmol), Pd(PPh<NUM>)<NUM> (<NUM>, <NUM> mmol), K<NUM>CO<NUM> (<NUM>, <NUM> mmol), THF (<NUM>), and water(<NUM>) were added and stirred at <NUM> ° C. When the reaction was complete, the reaction mixture was extracted with CH<NUM>Cl<NUM> and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of Core <NUM>.

Examples of the Core are as follows, but are not limited thereto. In addition, [Table <NUM>] shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Core. <CHM>
<CHM>
<CHM>
<CHM>.

Examples of Sub are as follows, but are not limited thereto. In addition, Table <NUM> shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub. <CHM>
<CHM>
<CHM>
<CHM>.

In a round bottom flask, Core <NUM> (<NUM>, <NUM> mmol), Sub <NUM> (<NUM>, <NUM> mmol), Pd(PPh<NUM>)<NUM>(<NUM>, <NUM> mmol), K<NUM>CO<NUM> (<NUM>, <NUM> mmol), THF and water were added and stirred at <NUM> ° C. When the reaction was complete, the reaction mixture was extracted with CH<NUM>Cl<NUM> and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of P-<NUM>.

Table <NUM> shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Product.

The compounds (final products <NUM>) represented by Formula (<NUM>) (not forming part of the claimed invention) can be prepared by reacting Sub <NUM>-<NUM> and Sub <NUM>-<NUM> as shown in the following Reaction Scheme <NUM>, but are not limited thereto.

<NUM>-bromo-<NUM>-phenyl-<NUM>-carbazole (<NUM>, <NUM> mmol) was dissolved in THF, and (<NUM>-(<NUM>,<NUM>-diphenyl-<NUM>,<NUM>,<NUM>-triazin-<NUM>-yl)-<NUM>-carbazol-<NUM>-yl)boronic acid (<NUM>, <NUM> mmol), Pd(PPh<NUM>)<NUM> (<NUM> eq. ), K2CO3(<NUM> eq. ) and water were added and refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting organic material was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of the product.

<NUM>-bromo-<NUM>-(pyridin-<NUM>-yl)-<NUM>-benzo[c]carbazole (<NUM>, <NUM> mmol), dibenzo[b,d]furan-<NUM>-ylboronic acid (<NUM>, <NUM> mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

<NUM>-([<NUM>,<NUM>'-biphenyl]-<NUM>-yl)-<NUM>-bromo-<NUM>-carbazole (<NUM>, <NUM> mmol), (<NUM>-(naphthalen-<NUM>-yl)-<NUM>-carbazol-<NUM>-yl)boronic acid (<NUM>, <NUM> mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

<NUM>'-bromo-<NUM>-phenyl-<NUM>-<NUM>,<NUM>'-bicarbazole (<NUM>, <NUM> mmol), (<NUM>-phenyl-<NUM>-carbazol-<NUM>-yl)boronic acid (<NUM>, <NUM> mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

<NUM>-bromo-<NUM>-(dibenzo[b,d]furan-<NUM>-yl)-<NUM>-carbazole (<NUM>, <NUM> mmol), (<NUM>-([<NUM>,<NUM>':<NUM>',<NUM>"-terphenyl]-<NUM>-yl)-<NUM>-benzo[<NUM>,<NUM>]thieno[<NUM>,<NUM>-a]carbazol-<NUM>-yl)boronic acid (<NUM>, <NUM> mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

<NUM>-bromo-<NUM>-phenyl-<NUM>-carbazole (<NUM>, 20mmol), (<NUM>-(dibenzo[b,d]thiophen-<NUM>-yl)phenyl)boronic acid (<NUM>, 20mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

<NUM>-bromo-<NUM>-phenyl-<NUM>-carbazole (<NUM>, <NUM> mmol), <NUM>(<NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-yl)boronic acid (<NUM>, <NUM> mmol) were carried out in the same manner as <NUM>-<NUM> to obtain <NUM> of the product (yield: <NUM>%).

Final products represented by Formula (<NUM>) (not forming part of the claimed invention) can be prepared by reacting as follows, but are not limited thereto. Synthesis Example of <NUM>-<NUM>
<CHM>.

<NUM>-(<NUM>'-bromo-[<NUM>,<NUM>'-biphenyl]-<NUM>-yl)-<NUM>-carbazole(<NUM>, 24mmol) was dissolved in toluene, and di([<NUM>,<NUM>'-biphenyl]-<NUM>-yl)amine(<NUM>, 20mmol), Pd<NUM>(dba)<NUM> (<NUM> eq. ), PPh<NUM>(<NUM> eq. ), NaOt-Bu (<NUM> eq. ) were added and refluxed with stirring at <NUM> ° C at <NUM> hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting organic material was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of the product.

<NUM>-(<NUM>-bromophenyl)-<NUM>-phenyl-<NUM>-carbazole (<NUM>, 24mmol) was dissolved in toluene, and N-([<NUM>,<NUM>'-biphenyl]-<NUM>-yl)-<NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-amine(<NUM>, 20mmol), Pd<NUM>(dba)<NUM> (<NUM> eq. ), PPh<NUM>(<NUM> eq. ), NaOt-Bu (<NUM> eq. ) were added and refluxed with stirring at <NUM> ° C at <NUM> hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting organic material was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of the product.

In a round bottom flask, Sub <NUM>(<NUM>) (<NUM>, 20mmol), Sub <NUM>(<NUM>) (<NUM>, 20mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM>. 6mmol), P(t-Bu)<NUM> (<NUM>, 2mmol), t-BuONa (<NUM>, 60mmol), toluene (<NUM>) were added and were carried out at <NUM> ° C. When the reaction was complete, the reaction mixture was extracted with CH<NUM>Cl<NUM> and water. The organic layer was dried over MgSO<NUM> and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallization to obtain <NUM> (yield: <NUM>%) of <NUM>-<NUM>.

In a round bottom flask, Sub <NUM>(<NUM>) (<NUM>, 20mmol), Sub <NUM>(<NUM>) (<NUM>, 20mmol), , Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

In a round bottom flask, Sub <NUM>(<NUM>) (<NUM>, <NUM> mmol), Sub <NUM>(<NUM>) (<NUM>, 20mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

In a round bottom flask, N-([<NUM>,<NUM>'-biphenyl]-<NUM>-yl)-<NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-amine(<NUM>, <NUM> mmol), <NUM>-(<NUM>-bromophenyl)-<NUM>,<NUM>-diphenyl-<NUM>-fluorene (<NUM>, <NUM> mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

In a round bottom flask, N-(<NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-yl)dibenzo[b,d]furan-<NUM>-amine(<NUM>, <NUM> mmol), N-(<NUM>-bromophenyl)-N-(<NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-yl)dibenzo[b,d]furan-<NUM>-amine(<NUM>, <NUM> mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

Final products represented by Formula (<NUM>) can be prepared by reacting Sub <NUM> and Sub <NUM> as shown in Reaction Scheme <NUM> below, but are not limited thereto. Only compound <NUM>-<NUM> forms part of the claimed invention.

In a round bottom flask, <NUM>-(<NUM>-phenyl-<NUM>-fluoren-<NUM>-yl)aniline (<NUM>, 20mmol), <NUM>-bromo-<NUM>,<NUM>-dimethyl-<NUM>-fluorene (<NUM>, 20mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give Sub <NUM>(<NUM>). (<NUM>, <NUM> %).

Examples of Sub <NUM> are as follows, but are not limited thereto. <CHM>
<CHM>
<CHM>.

In a round bottom flask, N-(<NUM>-(<NUM>-phenyl-<NUM>-fluoren-<NUM>-yl)phenyl)dibenzo[b,d]furan-<NUM>-amine (<NUM>, 20mmol), <NUM>-bromo-<NUM>,<NUM>-dimethyl-<NUM>-fluorene (<NUM>, <NUM> mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene (<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

In a round bottom flask, Sub <NUM>(<NUM>) (<NUM>, <NUM> mmol), Sub <NUM>-<NUM> (<NUM>, <NUM> mmol), Pd<NUM>(dba)<NUM> (<NUM>, <NUM> mmol), P(t-Bu)<NUM> (<NUM>, <NUM> mmol), t-BuONa (<NUM>, <NUM> mmol) and toluene(<NUM>) were carried out in the same manner as in <NUM>-<NUM> to give <NUM>-<NUM>. (<NUM>, <NUM> %).

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenyl benzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>, and on the layer, <NUM>,<NUM>-bis [N-(<NUM>-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as hole transport compounds to form a hole transport layer with a thickness of <NUM>. Subsequently, the compound represented by Formula (<NUM>) was used as a host, and an emitting layer with a thickness of <NUM> was deposited as a dopant on the hole transport layer by doping Ir(ppy)<NUM>[tris(<NUM>-phenylpyridine)-iridium] with a weight of <NUM>:<NUM>. (<NUM>,<NUM>' - bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of <NUM>. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent(EL) properties were measured using PR-<NUM> of Photoresearch Co. , and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of <NUM> cd/m<NUM>. In the following table, the manufacture of a device and the results of evaluation are shown.

An OLED was prepared in the same manner as in Example <NUM>, except that Comparative Compound A, Comparative Compound B, Comparative Compound C and Comparative Compound D were used as a host.

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenyl benzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>, and on the layer, <NUM>,<NUM>-bis [N-(<NUM>-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as hole transport compounds to form a hole transport layer with a thickness of <NUM>. Subsequently, a mixture of the compound represented by Formula (<NUM>) and the compound represented by Formula (<NUM>) in a ratio of <NUM>: <NUM> was used as a host, and as a dopant, an emitting layer with a thickness of <NUM> was deposited on the hole transport layer by doping Ir(ppy)<NUM>[tris(<NUM>-phenylpyridine)-iridium] with a weight of <NUM>:<NUM>. (<NUM>,<NUM>' - bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of <NUM>. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

An OLED was prepared in the same manner as in Example <NUM>, except that Comparative Compound A, Comparative Compound B, Comparative Compound C, and Comparative Compound D were used as a host instead of the compound represented by Formula (<NUM>).

An OLED was prepared in the same manner as in Example <NUM>, except for using the comparative compound E instead of the compound represented by Formula (<NUM>) as a host,
<CHM>.

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenylbenzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>. Subsequently, on the layer, <NUM>,<NUM>-bis[N-(<NUM>-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as an hole transport compound to a thickness of <NUM> to form a hole transport layer. Subsequently, the compound represented by Formula (<NUM>) was vacuum-deposited as an emitting auxiliary layer material to a thickness of <NUM> to form an emitting auxiliary layer. After forming the emitting auxiliary layer, a mixture of the compound represented by Formula (<NUM>) and the compound represented by Formula (<NUM>) in a ratio of <NUM>: <NUM> was used on the emitting auxiliary layer, and as a dopant, an emitting layer with a thickness of <NUM> was deposited by doping Ir(ppy)<NUM>[tris(<NUM>-phenylpyridine)-iridium] with a weight of <NUM>:<NUM>. (<NUM>,<NUM>' - bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of <NUM>. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

An OLED was prepared in the same manner as in Example <NUM>, except that the comparative compound A to E are each used instead of the compound represented by Formula (<NUM>) as a host,.

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenylbenzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>. Subsequently, on the layer, the compound represented by Formula(<NUM>) was vacuum-deposited to a thickness of <NUM> to form a hole transport layer. Subsequently, the compound represented by Formula(<NUM>) was vacuum-deposited as an emitting auxiliary material to a thickness of <NUM> to form an emitting auxiliary layer. After forming the emitting auxiliary layer, a mixture of the compound represented by Formula (<NUM>) and the compound represented by Formula (<NUM>) in a ratio of <NUM>: <NUM> was used as a host, and as a dopant, an emitting layer with a thickness of <NUM> was deposited by doping Ir(ppy)<NUM>[tris(<NUM>-phenylpyridine)-iridium] with a weight of <NUM>:<NUM>. (<NUM>,<NUM>' -bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of <NUM> as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

As can be seen from the results of Table <NUM> to <NUM>, the organic electronic element using the organic electronic device material of the present invention as a phosphorescent host can remarkably improve the high luminous efficiency, the low driving voltage and the lifetime.

Table <NUM> shows the superiority of the compounds of the invention compared to the comparative compounds when the inventive compound represented by Formula (<NUM>) was used as a single host. In the results of Comparative Compound A and Comparative Compound C, when the <NUM>-dibenzofuran was substituted, the performance was improved in all aspects of driving voltage, efficiency and lifetime, compared with <NUM>-dibenzofuran. In the results of Comparative Compound A and Comparative Compound B, or Comparative Compound C and Comparative Compound D, it can be confirmed that the performance of the triazine substituted with two dibenzothiophene or dibenzofuran moiety is improved compared with the triazine substituted with one dibenzothiophene or dibenzofuran moiety. Thus, it can be finally confirmed that the inventive compound, in which triazine is substituted with <NUM>-dibenzofuran and is linked by a linker with <NUM>-dibenzothiophen to the other side, exhibits an improved result which is significantly different from the comparative compounds A to D. It is suggested that the energy level (HOMO, LUMO, T1, etc.) of the compound may vary significantly depending on the kind of the substituent or the substitution position, and the differences in the physical properties of compounds may act as key factors(ex. energy balance) in improving device performance during device deposition, resulting in different device results.

Table <NUM> shows that when the compound represented by Formula (<NUM>) and the compound of Formula (<NUM>) are mixed, they are significantly better than other comparison combinations. This result is also supported the explanations in the case of a single host, and when bonded to Formula (<NUM>), the driving and efficiency can be improved by about <NUM>% and the lifetime can be improved by about <NUM>% compared with a single host. When two hosts are premixed, the aging rate is very important to deposit at a certain rate, and the compound of the present examples was superior in the aging rate compared with other materials, and particularly, the compound that at least one of Ar<NUM>, Ar<NUM> and R<NUM> is a C<NUM>-C<NUM> aryl group has the best results in the aging test.

Table <NUM> is the examples using the mixed compound of Formula (<NUM>) and Formula (<NUM>) as the emitting layer host and using the compound represented by Formula (<NUM>) in the emitting auxiliary layer, and shows that the efficiency is improved by about <NUM>% and the lifetime is improved by about <NUM>% compared with Table <NUM>. Here, using the compound represented by Formula (<NUM>) as the hole transport compound also yielded slightly improved results in terms of driving voltage, efficiency, and lifetime in comparison with the results in Table <NUM>.

That is, the compound of the present examples exhibits improved results compared with the known compounds even when used as a single host, but when used in combination with the compound represented by Formula (<NUM>), or when the compound represented by Formula (<NUM>) was used for the emitting auxiliary layer or the hole transport layer, remarkable results were obtained.

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenylbenzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>. Subsequently, and on the layer, <NUM>,<NUM>-bis[N-(<NUM>-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited to a thickness of <NUM> to form a hole transport layer. Subsequently, the inventive compound was vacuum-deposited as an emitting auxiliary layer material to a thickness of <NUM> to form an emitting auxiliary layer. After forming the emitting auxiliary layer, on the emitting auxiliary layer, <NUM>,<NUM>-di(naphthalen-<NUM>-yl)anthracene is used as a host, and BD-052X(Idemitsu kosan) is used as dopant in a ratio of <NUM> : <NUM>, therefore an emitting layer with a thickness of <NUM> was deposited on the emitting auxiliary layer. (<NUM>,<NUM>' -bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of <NUM> as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent(EL) properties were measured using PR-<NUM> of Photoresearch Co. , and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of <NUM> cd/m<NUM>. In the following table, the manufacture of a device and the results of evaluation are shown. Examples (<NUM>)-(<NUM>) and (<NUM>)-(<NUM>) are not forming part of the claimed invention.

An OLED was prepared in the same manner as in Comparative Example <NUM> except that the emitting auxiliary layer was not used and Comparative Compound F, Comparative Compound G and Invention Compound <NUM>-<NUM> were used as the hole transport layer material.

An OLED was prepared in the same manner as in Comparative Example <NUM> except that the emitting auxiliary layer was not used.

An OLED was prepared in the same manner as in Comparative Example <NUM> except that the Comparative Compound F or Comparative Compound G were used as the emitting auxiliary layer material.

First, on an ITO layer(anode) formed on a glass substrate, N<NUM>-(naphthalen-<NUM>-yl)-N<NUM>,N<NUM>-bis(<NUM>-(naphthalen-<NUM>-yl(phenyl)amino)phenyl)-N<NUM>-phenylbenzene-<NUM>,<NUM>-diamine(hereinafter will be abbreviated as <NUM>-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of <NUM>. Subsequently, and on the layer, <NUM>,<NUM>-bis[N-(<NUM>-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as a hole transport compound to a thickness of <NUM> to form a hole transport layer. Subsequently, the compound represented by Formula(<NUM>) was vacuum-deposited as an emitting auxiliary layer material to a thickness of <NUM> to form an emitting auxiliary layer. After forming the emitting auxiliary layer, on the emitting auxiliary layer, <NUM>,<NUM>'-di(<NUM>-carbazol-<NUM>-yl)-<NUM>,<NUM>'-biphenyl is used as a host, and Ir(ppy)<NUM>[tris(<NUM>-phenylpyridine)-iridium] is used as dopant in a ratio of <NUM> : <NUM>, and an emitting layer with a thickness of <NUM> was deposited. (<NUM>,<NUM>' - bisphenyl)-<NUM>-olato)bis(<NUM>-methyl-<NUM>-quinolinolato)aluminum(hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of <NUM>, and Tris(<NUM>-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of <NUM> as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of <NUM>, and Al was deposited to a thickness of <NUM> to form a cathode to manufacture an OLED.

An OLED was prepared in the same manner as in Comparative Example <NUM> except that Comparative Compound F or Comparative Compound G were used as the emitting auxiliary layer material.

As can be seen from the results of Table <NUM> to <NUM>, when OLED was manufactured by using the material for an organic electroluminescence device of the present invention as an emitting auxiliary layer material, the driving voltage of the organic electroluminescent device can be lowered and the luminous efficiency and lifetime can be remarkably improved as compared with the comparative example not using the material for the emitting auxiliary layer or using the comparative compound F or the comparative compound G.

Table <NUM> shows the results of the production of a blue organic light emitting device. It can be confirmed that excellent results are obtained when the compound of the present invention is used as an emitting auxiliary layer. The results of Comparative Example <NUM> or Comparative Example <NUM> and Examples <NUM> to <NUM> show that compounds of the present invention substituted with specific substituents such as DBT, DBF, Cz, and Fluorene are remarkably superior to the comparative compounds substituted with the general aryl group even though the mother compound is similar. That is, when specific substituents such as DBT, DBF, Cz, and Fluorene are introduced, the refractive index, the Tg, and the energy level of the compound (HOMO, LUMO, T1, etc.) become significantly different, and this difference in physical properties is a major factor in improving the device performance during device deposition(for example, such as an energy balance), such that different device results can be derived.

Table <NUM> shows the results of the production of a green organic light emitting device. When the compound of the present examples was used as an emitting auxiliary layer, the results were significantly superior to the comparative compounds. This is also the effect of certain substituents such as DBT, DBF, Cz, and Fluorene, and a specific feature is that the superiority of the green auxiliary layer is significantly improved than the blue auxiliary layer. Further, in the case of the blue auxiliary layer, DBT and DBF substituted compounds showed the most excellent properties, but the results of the green auxiliary layer showed the best results with the Fluorene substituted compounds. This suggests that even if the emitting auxiliary layer compound is the same, the properties required depending on the color of the emitting layer are different, so that a result which cannot be deduced by those skilled in the art can be obtained.

Claim 1:
An organic electronic element (<NUM>) comprising an anode (<NUM>); a cathode (<NUM>); an organic material layer formed between the anode and the cathode, wherein the organic material layer includes an emitting layer (<NUM>), a hole transport layer (<NUM>) formed between the anode (<NUM>) and the emitting layer (<NUM>); and an emitting auxiliary layer (<NUM>) or an electron blocking layer(EBL) formed between the emitting layer (<NUM>) and the hole transport layer (<NUM>); characterized in that the emitting auxiliary layer (<NUM>) or the electron blocking layer comprises a compound represented by Formula (<NUM>):
<CHM>
wherein in Formula (<NUM>):
R<NUM> is selected from the group consisting of hydrogen; deuterium; a C<NUM>-C<NUM> aryl group;
R<NUM>, R<NUM>, R<NUM>, and R<NUM> are each independently selected from the group consisting of hydrogen, and deuterium;
R<NUM>, is selected from the group consisting of hydrogen, deuterium, and a C<NUM>-C<NUM> alkyl group;
v is an integer of <NUM> to <NUM>,
u, w, x and y are each independently an integer of <NUM> to <NUM>,
Z is an integer of <NUM> to <NUM>,
L<NUM> is a single bond;
L<NUM> is a single bond, or a C<NUM>-C<NUM> arylene group;
Ar<NUM> is an unsubstituted C<NUM>-C<NUM> aryl group;
X<NUM> is CR'R", wherein R' and R" are each independently selected from the group consisting of a C<NUM>-C<NUM> alkyl group.