Compound for organic electronic element, organic electronic element using the compound, and electronic device thereof

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and service life of a device, an organic electronic element using the compound and an electronic device thereof.

Description

Technical Field

[0001] The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device thereof. Background Art

[0002] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic electronic element using the organic light emitting phenomenon generally 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 generally composed of a multilayer structure composed of different materials and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

[0003] Materials used as organic material layers in organic electronic elements can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. In addition, light-emitting materials can be classified into high molecular weight types and low molecular weight types according to molecular weight, and can be divided into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons according to the light-emitting mechanism. In addition, light-emitting materials can be classified into blue-emitting materials, green-emitting materials, and red-emitting materials according to emission colors, as well as yellow-emitting materials and orange-emitting materials necessary to achieve more natural colors.

[0004] However, when only one material is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and there is a problem of reducing color purity or reducing device efficiency due to the emission attenuation effect. Therefore, in order to increase color purity and increase luminous efficiency through energy transfer, a host / dopant system can be used as a light-emitting material. The principle is that when a small amount of a dopant having a smaller band gap than the band gap of the host forming the light-emitting layer is mixed in the light-emitting layer, the excitons generated in the light-emitting layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light with a desired wavelength can be obtained according to the type of dopant used.

[0005] Currently, the portable display market is large displays, and their size is increasing day by day, therefore, more power consumption is required than that required by existing portable displays. Therefore, for portable displays with limited power supply such as batteries, power consumption becomes a very important factor, and the issues of efficiency and service life must also be addressed.

[0006] Efficiency, service life and driving voltage are related to each other, and when efficiency increases, the driving voltage is relatively reduced, and as the driving voltage decreases, the crystallization of organic materials caused by Joule heating generated during driving decreases, so the service life tends to increase. However, efficiency cannot be maximized simply by improving the organic material layer. This is because when the energy level and T1 value between each organic material layer and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined, long service life and high efficiency can be achieved at the same time.

[0007] Therefore, while delaying the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the reasons for shortening the service life of organic electronic components, it should have stable characteristics against Joule heating generated during device driving, and OLED devices are mainly formed by a deposition method, and it is necessary to develop materials that can withstand long-term deposition, that is, materials with strong heat resistance.

[0008] In other words, in order to fully demonstrate the excellent characteristics of organic electronic components, priority should be given to materials that are competent for forming the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. However, the development of stable and effective organic material layer materials for organic electronic devices has not been fully realized. Therefore, there is a continuous need to develop new materials, and in particular, there is an urgent need to develop host materials for the light-emitting layer. Summary of the invention

[0009] In order to solve the above-mentioned problems of the background art, the present invention discloses a compound having a novel structure, and when the compound is applied to an organic electronic element, it has been found that the luminous efficiency, stability and service life of the device can be significantly improved.

[0010] Therefore, an object of the present invention is to provide a novel compound, an organic electronic element using the compound, and an electronic device thereof.

[0011] [Technical solution]

[0012] The present invention provides a compound represented by Formula 1-1.

[0013] Formula 1-1

[0014]

[0015] In another aspect, the present invention provides an organic electronic element including the compound represented by Formula 1-1 and an electronic device thereof.

[0016] [Effects of the invention]

[0017] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of a device can be achieved, and the color purity and service life of the device can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention. DETAILED DESCRIPTION

[0019] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when a detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0020] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. 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 the components.

[0021] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0022] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0023] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0024] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0025] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0026] Unless otherwise specified, the term “alkoxy group,” “alkoxy group,” or “alkyloxy group” as used herein means an oxy group attached to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0027] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means that an oxy group is connected to an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0028] Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, but are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by connecting or reacting adjacent substituents.

[0029] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0030] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0031] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0032] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any of a monocyclic and polycyclic ring, and may include a heteroaliphatic ring and a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0033] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0034] In addition, the term "heterocyclic group" may include a ring containing SO2 instead of carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0035]

[0036] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0037]

[0038] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to the number of spiro atoms in the compound.

[0039] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0040] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0041] In addition to the above mentioned hetero compounds, other hetero compounds or hetero groups contain but are not limited to one or more hetero atoms.

[0042] In addition, unless otherwise specified, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterated C6-C 20 Aryl group, C8-C 20 Arylene groups, silane groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but are not limited to these substituents.

[0043] In addition, unless otherwise specifically explained, the formulae used in the present invention are the same as the definitions of substituents by the following exponent definitions of the formulae.

[0044]

[0045] Here, when a is an integer of 0, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 Connected to any one of the carbon atoms constituting the benzene ring, when a is an integer of 2 or 3, each is combined as follows, wherein R 1 may be the same as or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, but indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

[0046]

[0047] Hereinafter, a compound according to aspects of the present invention and an organic electronic element including the compound will be described.

[0048] The present invention provides a compound represented by Formula 1-1.

[0049] Formula 1-1

[0050]

[0051] In formula 1-1, each symbol can be defined as follows.

[0052] 1) L 1 is a substituent represented by any one of Formula L-1 to Formula L-4,

[0053]

[0054] 2) L 2 is a single bond; or C6-C 60 arylene groups;

[0055] 3) Ar is C6-C 60 Aryl groups are preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0056] 4) Ring A is a substituent represented by formula a or formula b;

[0057]

[0058] 5) R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as or different from each other and are each independently hydrogen or deuterium;

[0059] 6) R 7 Selected from hydrogen; deuterium; C6-C 60Aryl group; and deuterated C6-C 60 Aryl groups;

[0060] 7) a and d are independently integers from 0 to 5,

[0061] b and f are independently integers from 0 to 6,

[0062] c, e, g and h are each independently an integer from 0 to 4,

[0063] i is an integer from 0 to 7,

[0064] 8) * means the position to be bonded,

[0065] 9) Here, the aryl group and the arylene group may be further substituted by one or more substituents, respectively, selected from deuterium; C6-C 20 Aryl group; and deuterated C6-C 20 Aryl group.

[0066] L 2 It can be represented by any one of Formulas a-1 to a-20.

[0067]

[0068] In Formula a-1 to Formula a-20, each symbol can be defined as follows.

[0069] 1) R 101 and R 102 are the same or different and are independently hydrogen; deuterium; C6-C 20 Aryl group; or C6-C substituted by deuterium 20 Aryl groups;

[0070] If R 101 and R 102 are aryl groups, which may be phenylene, biphenyl, naphthalene, terphenyl, etc.;

[0071] 2) aa, ab and ac are each independently an integer from 0 to 4, ad is an integer from 0 to 6, and ae is an integer from 0 to 8,

[0072] 3) * means the position where triazine or Ar is bonded.

[0073] Ar can be represented by any one of Formula b-1 to Formula b-8.

[0074]

[0075] In Formula b-1 to Formula b-8, each symbol can be defined as follows.

[0076] 1) R103 It is hydrogen; deuterium; C6-C 20 Aryl group; or C6-C substituted by deuterium 20 Aryl groups;

[0077] If R 103 is an aryl group, which can be phenylene, biphenyl, naphthalene, terphenyl, etc.;

[0078] 2) ba is an integer from 0 to 5, bb is an integer from 0 to 7, bc is an integer from 0 to 9,

[0079] 3) It means the position bonded to L.

[0080] Formula L-1 may be preferably represented by any one of Formula L-1-1 to Formula L-1-3.

[0081]

[0082] {In Formula L-1-1 to Formula L-1-3, R 5 , e and * are as defined above.}

[0083] Formula L-2 may be preferably represented by any one of Formula L-2-1 to Formula L-2-4.

[0084]

[0085]

[0086] {In formula L-2-1 to formula L-2-4, R 5 , f and * are as defined above.}

[0087] Formula L-3 may be preferably represented by any one of Formula L-3-1 to Formula L-3-8.

[0088]

[0089] {In formula L-3-1 to formula L-3-8, R 5 , f and * are as defined above.}

[0090] Formula L-4 may be preferably represented by any one of Formula L-4-1 to Formula L-4-6.

[0091]

[0092] {In formula L-4-1 to formula L-4-6, R 5 , R 6 , g, h and * are as defined above.}

[0093] In addition, Formula 1-1 is represented by Formula 1-1-a or Formula 1-1-b.

[0094]

[0095] {In Formula 1-1-a or Formula 1-1-b, R 1 , R 2 , R 3 , R 4 , R 7 , L 1 , L 2 , Ar, a, b, c, d and i are the same as defined above.}

[0096] In addition, Formula 1-1 is represented by any one of Formulas 1-1-1 to 1-1-5.

[0097]

[0098] {In Formula 1-1-1 to Formula 1-1-5, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, c, d, e, f, g, h and i are the same as defined above.}

[0099] In addition, Formula 1-1 is represented by any one of Formula 1-1-1-a to Formula 1-1-1-c.

[0100]

[0101] {In Formula 1-1-1-a to Formula 1-1-1-c, R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and e are the same as defined above.}

[0102] In addition, Formula 1-1 is represented by any one of Formulas 1-1-2-a to 1-1-2-c.

[0103]

[0104] {In Formula 1-1-2-a to Formula 1-1-2-c, R 1 , R 2 , R 3 , R 4 , R 5 , L2 , Ar, a, b, c, d and f are the same as defined above.}

[0105] In addition, Formula 1-1 is represented by Formula 1-1-3-a or Formula 1-1-3-b.

[0106]

[0107] {In Formula 1-1-3-a or Formula 1-1-3-b, R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and f are the same as defined above.}

[0108] In addition, Formula 1-1 is represented by Formula 1-1-4-a.

[0109]

[0110] {In formula 1-1-4-a, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are as defined above.}

[0111] In addition, Formula 1-1 is represented by Formula 1-1-4-b or Formula 1-1-4-c.

[0112]

[0113] {In Formula 1-1-4-b or Formula 1-1-4-c, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are the same as defined above.}

[0114] In addition, Formula 1-1 is represented by any one of Formulas 1-1-5-a to 1-1-5-c.

[0115]

[0116] {In Formula 1-1-5-a to Formula 1-1-5-c, R 1 , R 2 , R 3 , R5 , R 7 , L 2 , Ar, a, b, c, e and i are the same as defined above.}

[0117] Furthermore, the compound represented by Formula 1-1 is represented by any one of the following Compound P-1 to Compound P-44.

[0118]

[0119]

[0120]

[0121] refer to Figure 1 , the organic electronic element (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer containing a single compound or two or more compounds represented by Formula 1 between the first electrode (110) and the second electrode (170). In this case, the first electrode (110) may be an anode, and the second electrode (170) may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0122] The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110) in sequence. In this case, the remaining layers except the light emitting layer (140) may not be formed. A hole blocking layer, an electron blocking layer, a light emitting auxiliary layer (220), a buffer layer (210), etc. may also be included, and the electron transport layer (150) etc. may be used as a hole blocking layer. (See Figure 2 )

[0123] In addition, the organic electronic element according to the embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer may be formed on one of the two surfaces of the first electrode that is not in contact with the organic material layer, or on one of the two surfaces of the second electrode that is not in contact with the organic material layer. The compound according to the embodiment of the present invention suitable for the organic material layer may be used as a hole injection layer (120), a hole transport layer (130), a light-emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150) and an electron injection layer (160), a host or dopant of a light-emitting layer (140), or as a material for a hole blocking layer or a light efficiency enhancement layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a material for a light-emitting layer.

[0124] The organic material layer may include two or more stacks, the stack including a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode, and the organic material layer further including a charge generation layer formed between the two or more stacks (see Figure 3 ).

[0125] In addition, even in the case of the same core, the band gap, electrical properties, interface properties, etc. may vary depending on the position where the substituent is bonded, so the selection of the combination of the core and the substituents bonded thereto is also very important, and in particular, when the optimal combination of the energy level and T1 value of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) is achieved, long service life and high efficiency can be achieved at the same time.

[0126] The organic electroluminescent device according to the embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or an alloy thereof is deposited on a substrate to form an anode, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150) and an electron injection layer (160) is formed thereon, and then it can be prepared by depositing a material that can be used as a cathode thereon.

[0127] Furthermore, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element containing the compound as an electron transport material.

[0128] As another specific example, the same or different compounds among the compounds represented by formula (1) are mixed and used in the organic material layer.

[0129] Furthermore, the present invention provides a composition for a light-emitting layer comprising the compound represented by formula (1), and provides an organic electronic element including the light-emitting layer.

[0130] Furthermore, the present invention provides an electronic device including a display device including an organic electronic element; and a control unit for driving the display device.

[0131] On the other hand, the organic electronic element is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a device for monochrome or white lighting. At this time, the electronic device can be a current or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals such as mobile phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various TVs, and various computers.

[0132] Hereinafter, a synthesis example of the compound represented by Formula 1 of the present invention and a manufacturing example of the organic electronic element of the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

[0133] [Synthesis example 1]

[0134] The compound represented by Formula 1-1 according to the present invention (final product) is synthesized as shown in Reaction Scheme 1, but is not limited thereto.

[0135] <Reaction Scheme 1>

[0136]

[0137] I. Synthesis of Sub1

[0138] The compound belonging to Sub1 may be the following compounds, but is not limited thereto, and the following Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compound belonging to Sub1.

[0139]

[0140]

[0141] [Table 1]

[0142] Compound FD-MS Compound FD-MS Sub1-1 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=280.16(C <h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 21 <h2 style=";text-align:left;direction:ltr"> BO2 = 280.17<h2 style=";text-align:left;direction:ltr"> Sub1-2 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=280.16(C <h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 21 <h2 style=";text-align:left;direction:ltr"> BO2 = 280.17<h2 style=";text-align:left;direction:ltr"> Sub1-3 <![CDATA[m / z=285.19(C 18 H 16 D5BO2=285.2)]]> Sub1-4 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=280.16(C <h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 21 <h2 style=";text-align:left;direction:ltr"> BO2 = 280.17<h2 style=";text-align:left;direction:ltr"> Sub1-5 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-6 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-7 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-8 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-9 <![CDATA[m / z=335.21(C 22 H 18 D5BO2=335.26)]]> Sub1-10 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-11 <![CDATA[m / z=335.21(C 22 H 18 D5BO2=335.26)]]> Sub1-12 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=356.19(C <h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> BO2 = 356.27<h2 style=";text-align:left;direction:ltr"> Sub1-13 <![CDATA[m / z=360.22(C 24 H 21 D4BO2=360.3)]]> Sub1-14 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=356.19(C <h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> BO2 = 356.27<h2 style=";text-align:left;direction:ltr"> Sub1-15 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-16 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-17 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=330.18(C <h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> BO2 = 330.23<h2 style=";text-align:left;direction:ltr"> Sub1-18 <![CDATA[m / z=334.2(C 22 H 19 D4BO2=334.26)]]> Sub1-19 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=406.21(C <h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2 = 406.33<h2 style=";text-align:left;direction:ltr"> Sub1-20 <![CDATA[m / z=410.24(C 28 H 23 D4BO2=410.36)]]> Sub1-21 <![CDATA[m / z=410.24(C 28 H 23 D4BO2=410.36)]]> Sub1-22 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=406.21(C <h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2 = 406.33<h2 style=";text-align:left;direction:ltr"> Sub1-23 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=409.23(C <h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> D3BO2 = 409.35<h2 style=";text-align:left;direction:ltr"> Sub1-24 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=406.21(C <h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2 = 406.33<h2 style=";text-align:left;direction:ltr"> Sub1-25 <![CDATA[m / z=410.24(C 28 H 23 D4BO2=410.36)]]>

[0143] II. Synthesis of Sub2

[0144] Sub2 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0145] <Reaction Scheme 2>

[0146]

[0147] 1. Synthesis example of Sub2-1

[0148]

[0149] After Sub2b-1 (13.9 g, 61.5 mmol) was dissolved in THF (tetrahydrofuran) (310 mL) in a round-bottom flask, Sub2a-1 (25.0 g, 61.5 mmol), NaOH (7.4 g, 184.6 mmol), Pd(PPh3)4 (4.27 g, 3.69 mmol) and water (155 mL) were added and stirred at 80°C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The obtained compound was recrystallized by a silica gel column to obtain 21.5 g (yield 74.5%) of the product.

[0150] 2. Synthesis example of Sub2-2

[0151]

[0152] (1) Synthesis example of Sub2a-2

[0153] After dissolving Sub2d-2 (22.9 g, 69.4 mmol) in THF (350 mL) in a round-bottom flask, Sub2c-2 (20.0 g, 69.4 mmol), NaOH (8.3 g, 208.2 mmol), Pd(PPh3)4 (4.81 g, 4.16 mmol) and water (175 mL) were added, and 20.4 g (yield 71.4%) of the product was obtained by using the synthesis method of Sub2-1.

[0154] (2) Synthesis example of Sub2-2

[0155] After dissolving Sub2b-1 (11.2 g, 49.5 mmol) in THF (250 mL) in a round-bottom flask, Sub2a-2 (20.4 g, 49.5 mmol), NaOH (5.9 g, 148.6 mmol), Pd(PPh3)4 (3.44 g, 2.97 mmol) and water (125 mL) were added, and 16.9 g (yield 71.7%) of the product was obtained by using the synthesis method of Sub2-1.

[0156] 3. Synthesis example of Sub2-9

[0157]

[0158] After dissolving Sub2b-9 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh3)4 (2.56 g, 2.21 mmol) and water (92 mL) were added, and 16.1 g (yield 73.3%) of the product was obtained by using the synthesis method of Sub2-1.

[0159] 4. Synthesis example of Sub2-13

[0160]

[0161] After dissolving Sub2b-13 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh3)4 (2.56 g, 2.21 mmol) and water (92 mL) were added, and 16.0 g (yield 72.7%) of the product was obtained by using the synthesis method of Sub2-1.

[0162] The compounds belonging to Sub2 may be the following compounds, but are not limited thereto. The following Table 2 shows the FD-MS (field desorption-mass spectrometry) values ​​of some compounds belonging to Sub2.

[0163]

[0164] [Table 2]

[0165] Compound FD-MS Compound FD-MS Sub2-1 <![CDATA[m / z=469.13(C 31 A 20 ClN3=469.97)]]> Sub2-2 <![CDATA[m / z=474.17(C 31 H 15 D5ClN3=475.00)]]> Sub2-3 <![CDATA[m / z=472.15(C 31 H 17 D3ClN3=472.99)]]> Sub2-4 <![CDATA[m / z=474.17(C 31 H 15 D5ClN3=475.00)]]> Sub2-5 <![CDATA[m / z=545.17(C 37 A 24 ClN3=546.07)]]> Sub2-6 <![CDATA[m / z=545.17(C 37 A 24 ClN3=546.07)]]> Sub2-7 <![CDATA[m / z=545.17(C 37 A 24 ClN3=546.07)]]> Sub2-8 <![CDATA[m / z=621.20(C 43 A 28 ClN3=622.17)]]> Sub2-9 <![CDATA[m / z=595.18(C 41 A 26 ClN3=596.13)]]> Sub2-10 <![CDATA[m / z=595.18(C 41 A 26 ClN3=596.13)]]> Sub2-11 <![CDATA[m / z=645.20(C 45 A 28 ClN3=646.19)]]> Sub2-12 <![CDATA[m / z=519.15(C 35 A 22 ClN3=520.03)]]> Sub2-13 <![CDATA[m / z=595.18(C 41 A 26 ClN3=596.13)]]> Sub2-14 <![CDATA[m / z=519.15(C 35 A 22 ClN3=520.03)]]> Sub2-15 <![CDATA[m / z=595.18(C 41 A 26 ClN3=596.13)]]> Sub2-16 <![CDATA[m / z=595.18(C 41 A 26 ClN3=596.13)]]> Sub2-17 <![CDATA[m / z=695.21(C 49 A 30 ClN3=696.25)]]> Sub2-18 <![CDATA[m / z=569.17(C 39 A 24 ClN3=570.09)]]> Sub2-19 <![CDATA[m / z=569.17(C 39 A 24 ClN3=570.09)]]>

[0166] III. Synthesis of the final product

[0167] 1. Synthesis Example of P-1

[0168]

[0169] After Sub2-1 (5.0 g, 10.7 mmol) was dissolved in THF (tetrahydrofuran) (54 mL) in a round-bottom flask, Sub1-1 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) and water (27 mL) were added and stirred at 80°C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The obtained compound was recrystallized by a silica gel column to obtain 4.8 g (yield 77%) of the product.

[0170] 2. Synthesis Example of P-8

[0171]

[0172] After dissolving Sub2-1 (4.9 g, 10.5 mmol) in THF (tetrahydrofuran) (53 mL) in a round-bottom flask, Sub1-3 (3.0 g, 10.5 mmol), NaOH (1.3 g, 31.6 mmol), Pd(PPh3)4 (0.73 g, 0.63 mmol) and water (26 mL) were added, and 4.6 g (yield 74%) of the product was obtained using the above synthesis method of P-1.

[0173] 3. Synthesis Example of P-9

[0174]

[0175] After dissolving Sub2-1 (5.0 g, 10.7 mmol) in THF (tetrahydrofuran) (54 mL) in a round-bottom flask, Sub1-4 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) and water (27 mL) were added, and 4.5 g (yield 71%) of the product was obtained using the above synthesis method of P-1.

[0176] 4. Synthesis Example of P-16

[0177]

[0178] After dissolving Sub2-10 (5.4 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-5 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 5.0 g (yield 72%) of the product was obtained using the above P-1 synthesis method.

[0179] 5. Synthesis Example of P-19

[0180]

[0181] After dissolving Sub2-1 (4.3 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-7 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.3 g (yield 75%) of the product was obtained using the above P-1 synthesis method.

[0182] 6. Synthesis Example of P-22

[0183]

[0184] After dissolving Sub2-1 (4.2 g, 8.9 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-9 (3.0 g, 8.9 mmol), NaOH (1.1 g, 26.8 mmol), Pd(PPh3)4 (0.62 g, 0.54 mmol) and water (22 mL) were added, and 4.2 g (yield 73%) of the product was obtained using the above synthesis method of P-1.

[0185] 7. Synthesis Example of P-25

[0186]

[0187] After dissolving Sub2-1 (4.3 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-10 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.5 g (yield 77%) of the product was obtained using the above synthesis method of P-1.

[0188] 8. Synthesis Example of P-30

[0189]

[0190] After dissolving Sub2-1 (4.0 g, 8.4 mmol) in THF (tetrahydrofuran) (42 mL) in a round-bottom flask, Sub1-12 (3.0 g, 8.4 mmol), NaOH (1.0 g, 25.3 mmol), Pd(PPh3)4 (0.58 g, 0.51 mmol) and water (21 mL) were added, and 4.1 g (yield 74%) of the product was obtained using the above synthesis method of P-1.

[0191] 9. Synthesis Example of P-34

[0192]

[0193] After dissolving Sub2-2 (4.3 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-15 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.6 g (yield 78%) of the product was obtained using the above P-1 synthesis method.

[0194] 10. Synthesis Example of P-40

[0195]

[0196] After dissolving Sub2-6 (5.0 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-16 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 5.0 g (yield 77%) of the product was obtained using the above P-1 synthesis method.

[0197] 11. Synthesis Example of P-42

[0198]

[0199] After dissolving Sub2-6 (5.0 g, 9.1 mmol) in THF (tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-17 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.5 g (yield 70%) of the product was obtained using the above P-1 synthesis method.

[0200] Meanwhile, Table 3 shows the FD-MS values ​​of Compound P-1 to Compound P-44 of the present invention prepared according to the above Synthesis Examples.

[0201] [Table 3]

[0202]

[0203]

[0204] Fabrication and evaluation of organic electronic components

[0205] [Example 1] Red organic light-emitting diode (phosphorescent host)

[0206] An organic electroluminescent device is manufactured according to a conventional method using a compound obtained by synthesis as a luminescent host material of a luminescent layer. First, on an ITO layer (anode) formed on a glass substrate, a N1-(naphthalene-2-yl)-N4,N4-bis(4-(naphthalene-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) film is vacuum deposited to form a thickness of 60nm as a hole injection layer. On the hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, NPD) as a hole transport compound is vacuum deposited to a thickness of 50nm to form a hole transport layer.

[0207] The light-emitting auxiliary layer is formed by vacuum depositing tris(4-(9H-carbazole-9-yl)phenyl)amine (hereinafter, TCTA) as a light-emitting auxiliary layer material on the hole transport layer to a thickness of 10nm. After the light-emitting auxiliary layer is formed, on the light-emitting auxiliary layer, the compound P-1 of the present invention represented by Formula 1-1 and the compound C-1 are used as the main body in a weight ratio of (5:5), and the light-emitting layer is deposited to a thickness of 30nm by doping (piq)2Ir(acac) as a doping material at a weight ratio of 95:5. Then, (1,1'-biphenyl)-4-root)bis(2-methyl-8-quinolinyl)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinyl)beryllium (hereinafter abbreviated as Alq3) is deposited to a thickness of 25nm as an electron transport layer. Then, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby preparing an organic electroluminescent device.

[0208] [Example 2] to [Example 22]

[0209] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 4 were used as host materials of the light-emitting layer instead of Compound P-1 and Compound C-1 of the present invention.

[0210] [Comparative Example 1] to [Comparative Example 3]

[0211] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 4 were used instead of the compound P-1 of the present invention as a host material of the light-emitting layer.

[0212]

[0213] <Comparative Compound C>

[0214]

[0215]

[0216] By applying a forward bias DC voltage to the organic electronic elements of Examples 1 to 22 and Comparative Examples 1 to 3 prepared in this manner, electroluminescence (EL) characteristics were measured with PR-650 from Photoresearch, and as a result of the measurement, a lifetime measurement device manufactured by McScience was used at 2500 cd / m 2 The T95 service life was measured under standard brightness. Table 4 shows the device fabrication and evaluation results.

[0217] [Table 4]

[0218]

[0219] According to the results in Table 4, when the compound of the present invention is used as a host material of the light-emitting layer, it can be seen that the device performance is greatly improved compared with Comparative Examples 1 to 3.

[0220] When the compound of the present invention represented by Formula 1-1 is compared with Comparative Compounds A to C, the type of substituent bonded to triazine is different, and the mobility varies depending on the type of substituent. In other words, the drive, efficiency, and service life are determined by the ease of hole and electron injection into the dopant, so when the hole and electron ratio (charge balance) is properly maintained, the efficiency and service life are judged to be significantly increased, which is expected to affect the charge balance according to the respective mobility levels of the first compound and the second compound.

[0221] For the overall characteristics, in the case of the compound of the present invention represented by Formula 1-1, the electronic stability is high, and therefore the electrical stability is high compared to the comparative compound, and therefore has a long service life characteristic. Comparing the compounds of the present invention, it can be seen that the device performance is determined according to the composition of the compound. In terms of driving voltage, it is highly dependent on the total EOD and HOD, and it can be seen that the mobility is determined by the type of substituents possessed by the compound, and the efficiency is determined by the electron-hole balance of the heterogeneous compound. As a result, the performance of the device is greatly affected depending on the type and bonding position of the substituents substituted in the same main chain.

[0222] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be understood by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims, and should be interpreted as all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0223] [reference numerals]

[0224] 100, 200, 300: organic electronic element 110: first electrode

[0225] 120: hole injection layer 130: hole transport layer

[0226] 140: Light-emitting layer 150: Electron transport layer

[0227] 160: electron injection layer 170: second electrode

[0228] 180: Light efficiency enhancement layer 210: Buffer layer

[0229] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0230] 330: first hole transport layer 340: first light emitting layer

[0231] 350: first electron transport layer 360: first charge generation layer

[0232] 361: second charge generation layer 420: second hole injection layer

[0233] 430: second hole transport layer 440: second light emitting layer

[0234] 450: Second electron transport layer CGL: Charge generation layer

[0235] ST1: first stack ST2: second stack

Claims

1. An organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises an electron blocking layer and contains a single compound or two or more compounds represented by Formula 1-1: <Formula 1-1> in: 1) L 1 is a substituent represented by any one of Formula L-1 to Formula L-4, 2) L 2 is a single bond; or C6-C 60 arylene groups; 3) Ar is C6-C 60 Aryl groups, 4) Ring A is a substituent represented by formula a or formula b; 5) R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as or different from each other and are each independently hydrogen or deuterium; 6) R 7 Selected from hydrogen; deuterium; C6-C 60 Aryl group; and deuterated C6-C 60 Aryl groups; 7) a and d are independently integers from 0 to 5, b and f are independently integers from 0 to 6, c, e, g and h are each independently an integer from 0 to 4, i is an integer from 0 to 7, 8) * means the position to be bonded, 9) Here, the aryl group and the arylene group may be further substituted by one or more substituents, respectively, selected from deuterium; C6-C 20 Aryl group; and deuterated C6-C 20 Aryl group.

2. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-a or Formula 1-1-b: Where R 1 , R 2 , R 3 , R 4 , R 7 , L 1 , L 2 , Ar, a, b, c, d and i are the same as defined in claim 1.

3. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by any one of Formula 1-1-1 to Formula 1-1-5: Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, c, d, e, f, g, h and i are the same as defined in claim 1.

4. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by any one of Formula 1-1-1-a to Formula 1-1-1-c: Where R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and e are the same as defined in claim 1.

5. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by any one of Formula 1-1-2-a to Formula 1-1-2-c: Where R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and f are the same as defined in claim 1.

6. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-3-a or Formula 1-1-3-b: Where R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and f are the same as defined in claim 1.

7. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-4-a: Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are as defined in claim 1.

8. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-4-b or Formula 1-1-4-c: Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are the same as defined in claim 1.

9. The organic electronic device according to claim 1, wherein Formula 1-1 is represented by any one of Formula 1-1-5-a to Formula 1-1-5-c: Where R 1 , R 2 , R 3 , R 5 , R 7 , L 2 , Ar, a, b, c, e and i are the same as defined in claim 1.

10. The organic electronic element according to claim 1, wherein the compound represented by Formula 1-1 is represented by any one of the following compounds P-1 to P-44: 11 . The organic electronic element of claim 1 , wherein the organic material layer further comprises at least one of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. 12 . The organic electronic device according to claim 1 , wherein the organic material layer further comprises a light emitting layer. 13 . The organic electronic element according to claim 12 , wherein the light emitting layer comprises a single compound or two or more compounds represented by Formula 1-1. 14 . The organic electronic element of claim 1 , further comprising a light efficiency enhancing layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer. 15 . The organic electronic element according to claim 1 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode. 16 . The organic electronic element according to claim 15 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies.

17. Electronic devices, including: A display device comprising the organic electronic element according to any one of claims 1 to 16; and a control unit for driving the display device. 18 . The electronic device according to claim 17 , wherein the organic electronic element is any one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white lighting.

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